March 26, 2026

Last week we laid out the four categories of redlines.

Must-haves. Judgment calls. Template collisions. Cosmetic noise.

If you saved that post, you probably already recognized the pattern in your own work. A lot of you told me as much.

But here's the thing about frameworks: they're easy to nod along with and hard to actually apply.

So this week, I want to focus on the category that does the most damage in practice.

Not Category 1. Those are rare and obvious.

Not Category 4. Annoying, sure. But marginal. Just friggin’ behave yourself.

Let’s dive into Category 3.

The template collision.

This is where most negotiation drag actually lives.

Twenty Ways to Say the Same Thing

Here's something nobody in legal wants to admit out loud.

I can write the same clause twenty different ways.

Different structure. Different phrasing. Different clause architecture. Different length. All of them substantively identical.

You could put all twenty in front of a judge and get the same result.

But they don't look the same. And in contract negotiation, appearance often drives behavior.

When your version of a clause meets my version, something happens almost reflexively. The receiving lawyer sees unfamiliar language and flags it. Not because the substance is wrong. Because the content is different.

And once it's flagged, it gets redlined.

Another round. Another review cycle. Another week.

Nobody's risk position moved. But the deal just got slower.

This is Category 3 in its purest form. Two templates colliding. Two sets of perfectly reasonable language fighting for the same paragraph. Neither wrong. Both generating friction.

A Flashback Worth Revisiting

Way back in Entry 1.1 of the Redliner’s Diaries, I shared an email from a procurement professional that perfectly captured how far we've drifted from common sense. It's worth revisiting through the lens of what we now know about Category 3.

The key line: "My review process involves a thorough, section-by-section and word-by-word analysis, during which I will integrate our own form terms."

Read that again.

"Integrate our own form terms."

Section by section. Word by word. Fourteen to thirty days to process. Go back and look at the email in 1.1… I can’t make that shit up.

That's not risk analysis. That's not a judgment call about where the incoming contract falls short.

That's a template replacement exercise described, in writing, as a professional methodology.

Every clause in the incoming draft gets measured against their form. Not against what the clause actually does. Not against the risk it creates or fails to address. Against their preferred language.

Where the language matches, it survives. Where it doesn't, it gets overwritten. Regardless of whether the substance changes.

That is Category 3 operating at industrial scale.

And the most telling part? The email closed with a suggestion that it might be faster to just use their form agreement as the base document instead.

Not because our terms were deficient. Because their process requires their language. Full stop.

Fourteen to thirty days to steer us toward "no." Not because anyone was trying to kill the deal. Because the process had become the point.

When I first shared that email, I framed it as an example of redline theater. Now, many entries later, I think it illustrates something more specific: what happens when template application replaces legal judgment. When "review" means "replace with ours" and nobody stops to ask whether the original version already accomplished the same thing.

The Lazy Move vs. the Disciplined Move

When a lawyer encounters a clause that's written differently from their template, there are two possible responses.

The lazy move: swap in your version.

It's faster. It's easier. It doesn't require you to actually read and analyze what the other side wrote. You already have your clause library open. It’s been “approved.” You copy, you paste, you move on.

And you just manufactured a redline that didn't need to exist.

The disciplined move is harder. You read their version. You compare it to your position... not your language, your position. You ask: does this clause accomplish the same thing mine does? Is the delta between their version and mine substantive or preferential?

If it's preferential, you leave it alone. You move on. You save everyone a round.

That second move requires three things most people either don't have or don't exercise.

First, enough experience to distinguish preference from substance. You have to actually understand what the clause does... not just what it looks like.

Second, enough confidence to leave someone else's language in the document. This is harder than it sounds. Lawyers are trained to improve. Leaving a clause untouched when you could "make it better" feels like you're not doing your job.

Third, enough discipline to resist the instinct to perform. This ties directly back to what we talked about in the early entries... the ego problem. The compulsion to mark something up just to prove you were here.

When all three are present, Category 3 edits get caught before they become redlines.

When any one of them is missing, the template collision happens. And it happens over and over and over.

Who's Holding the Pen?

Here's where it gets structural.

The people most likely to make the lazy move are the ones least equipped to make the judgment call.

A junior lawyer sees unfamiliar language and defaults to what they know: the template. They don't yet have the experience to read a clause and recognize it as functionally equivalent to their own. So they swap. Every time.

A procurement team with a mandate to apply their standard form does exactly that. Clause by clause. Regardless of whether the incoming language already achieves the same outcome. We saw that email. That's the process working as designed.

And then there's AI.

Let's be fair. The current generation of contract review tools isn't just doing blind template matching. Many of them have real analytical capability. They can parse a clause, assess risk levels, flag genuine gaps. That's progress, and it's worth acknowledging.

But here's what they still don’t do well: context.

They don't know this is a $15,000 deal that needs to close by month-end. They don't know the customer is a strategic account you've been cultivating for two years. They don't know that your CEO promised the board six new logos this quarter and this is number five.

Without that context, the tool does what it's built to do. It finds differences. It flags them. It suggests changes. And because it can do this at scale, effortlessly, the volume of suggested edits goes up. Way up.

In my experience, we're seeing more redlines on more minor issues than ever before. Not because the tools are wrong, exactly. Because it's so easy. The cost of auto-generating a markup has dropped significantly. But the cost of responding to one hasn't changed to match it.

Every AI-suggested edit still requires the other side to review it, evaluate it, and decide whether to accept, reject, or counter. That process takes time. And effort. And money.

The tools will get better. They're getting better. But until they can weigh a preferential variation against deal economics, urgency, and relationship dynamics... they're accelerating the wrong part of the process.

Why the System Rewards the Wrong Behavior

You might read all of this and think: the fix is better training. Teach lawyers to recognize "close enough." Teach them when to leave a clause alone.

And sure, that helps. In the same way that telling people to eat better helps with public health. Technically true. Practically limited.

Because the system as it's built rewards the wrong behavior.

Law firms bill hours. More redlines means more hours. The incentive doesn't point toward restraint.

In-house teams measure thoroughness. A markup that comes back untouched raises eyebrows. "Did you actually review this?"

AI tools are built to find differences. They're getting better at assessing whether differences matter. But the default output is still a markup, and markups create rounds.

Template libraries exist to standardize language. So when language doesn't match, the library becomes the weapon.

Every piece of the infrastructure pushes toward more edits. The discipline to not edit... that's purely personal. And personal discipline doesn't scale.

The Cost Nobody's Tracking

We've talked about velocity. Rounds. Time. Money.

But here's what Category 3 actually costs that doesn't show up on any ledger.

The relationship.

Every unnecessary template swap sends a signal the sender doesn't intend. When you overwrite a clause that was functionally fine, the other side doesn't hear "preferential improvement." They hear: "Your language isn't good enough." Or worse: "I don't trust your drafting."

One swap, maybe that's just thoroughness. Five swaps across ten clauses and the tone shifts. The other side starts reading defensively. Shoulders tighten. Responses get sharper. What should have been a collaborative process starts feeling adversarial.

And it compounds.

By the time you've exchanged three rounds of Category 3 edits, both sides have spent weeks signaling distrust over provisions that say the same thing. The relationship hasn't even started yet and it's already strained.

I've seen deals close after this kind of process. They close tired. The business teams are exhausted. The goodwill that should have been the foundation of a working partnership got ground down in the markup. And nine months later, when something goes sideways and the parties need to work together to solve it, that residual friction shows up. People don't forget how the negotiation felt.

Category 3 isn't just drag. It's corrosive.

And here's the thing about AI in this context that I think gets missed. The tools can get smarter. They can get better at distinguishing preference from substance. They can learn to weigh deal economics and flag only what genuinely matters.

But they'll still be operating inside the same paradigm.

Closed hand of poker. Your draft versus mine. Redlines exchanged across the table like opposing briefs.

No matter how intelligent the tool becomes, if the structure of the interaction is adversarial, the relationship cost remains. You're still firing markups at each other. You're still signaling positions through edits instead of conversations. You're still playing the same game... it’s just the cards get shuffled and dealt faster.

What changes the relationship isn't a smarter tool inside the old process. It's a different process entirely. One where both sides can look at the same structure together. Where the opening move isn't "here's my redline" but "let's look at this together and decide where we actually disagree."

That's a fundamentally different signal. And it's one that no amount of AI sophistication inside the traditional redline exchange can replicate.

What Actually Needs to Change

The instinct to standardize is right. Having a playbook, having positions, knowing what your company cares about and where it flexes... that's essential.

But standardization focused on language will always collide with someone else's equally valid standardization of language.

Twenty versions of the same clause. All correct. All different. All generating friction when they meet.

The real leverage comes from standardizing on positions, not prose.

If you know where you stand on an issue... what you require, what you prefer, and where you're flexible... the specific words matter a lot less.

Because now you're reading the other side's clause and asking the right question.

Not: "Does this match my template?"

But: "Does this achieve my position?"

That's the shift. And it's the difference between a negotiation that generates twelve rounds and one that generates two.

Wrapping It Up

Category 3 is where deals quietly bleed time and trust.

Not through bad faith. Not through incompetence. Through the accumulated friction of two sets of reasonable language colliding on every clause, in every deal, generating redlines that move no one's risk position but erode everyone's goodwill.

The fix isn't better templates. It's better judgment about when to leave the other side's template alone. And beyond that, it's a structure that doesn't force both parties into an adversarial exchange in the first place.

That judgment is rare. It's hard to teach. And the current system actively discourages it.

Which means for most deals, the template collision will keep happening. Same fight. Different logos.

Until someone changes the game.

Join the discussion on LinkedIn.

March 19, 2026

A couple of weeks ago, we ran the math.

Fourteen rounds on a mid-six-figure SaaS deal.

Outside counsel fees on their side pushing well into five figures. Internal legal time on ours that nobody actually tracks.

Sales momentum slowed. The relationship strained. Everyone involved convinced they were simply doing their job.

But after walking through that example, a fair question naturally follows:

How does this actually happen?

Because most lawyers involved in those negotiations weren’t reckless.

They were being careful. Thoughtful. Professional.

Yet the process still produced enormous friction.

After about thirty years of practicing law, I’ve come to believe the explanation is surprisingly simple.

Contract negotiations rarely distinguish between the redlines that matter… and the ones that simply create motion.

A comma tweak travels through the same process as a liability clause. A stylistic preference consumes the same oxygen as a regulatory requirement.

Signal and noise move through the same pipe.

So at some point, I started doing something simple during my own reviews.

Before I change anything in a contract, I mentally sort the issue into one of four categories.

This isn’t a formal doctrine. Just a filter developed after a few thousand negotiations.

More importantly, it’s a way I police my own instincts when reviewing agreements.

Because lawyers are very good at improving documents.

Sometimes a little too good.

Category 1 — The Must-Have

These are non-negotiable.

Not because a lawyer prefers them.

Because something with authority behind them requires them.

Sometimes that authority is law.

If a company handles protected health information, HIPAA obligations must appear somewhere in the agreement.

If customer data crosses European borders, GDPR responsibilities have to be addressed.

Those aren’t drafting preferences.

They’re regulatory requirements.

Sometimes the authority is how the product actually works.

Take a commercial SaaS agreement.

If the license clause doesn’t properly grant the customer the right to use the software, the contract isn’t actually doing its job.

The agreement has to describe what the customer is allowed to do.

Otherwise, the entire structure collapses.

And sometimes the authority comes from inside the company.

Boards may approve risk tolerance. Management may set policies.

A company may refuse unlimited liability because of its size. Or decline to indemnify a customer for the customer’s own misuse of the product.

Those positions aren’t meant to be improvised mid-negotiation.

Category One redlines enforce those boundaries.

They deserve oxygen.

And fortunately, there aren’t many of them.

Or at least there shouldn’t be.

Category 2 — Where Legal Actually Adds Value

This is the work experienced counsel are supposed to do.

Not rewriting the contract for sport.

Modifying it where it matters.

Category Two issues require judgment… and, typically, experience.

A clause might technically work but expose the company to more risk than the deal justifies.

A sentence might technically say something but do so in a way that creates ambiguity if a dispute ever lands in court.

Sometimes language simply doesn’t align with the company’s broader strategy.

That’s where experience shows up.

In commercial deals, that might mean adjusting liability caps to match the economics of the deal.

Clarifying language that could produce competing interpretations later.

Expanding a clause that’s written too vaguely to guide real behavior.

There are also provisions that tend to be modified deal-to-deal because of real negotiation leverage… indemnities, liability caps, service levels.

Seasoned lawyers know these areas are commonly negotiated and understand where the market usually lands.

When I’m looking at issues in this category, I try to ask myself a simple question:

If I make this change, is it worth my time (and my client’s money) to do so?

Could I explain to the client why the issue matters?

Could I justify the legal spend required to push it?

Because every redline carries a cost.

Another round. Another review. Another conversation.

Category Two edits are the ones where that cost is justified.

This is where legal actually adds value.

Category 3 — The Template Collision

This is where negotiations usually start drifting.

Category Three edits often happen when two templates or playbooks collide.

One party has its preferred form, clauses, or positions. The other party has theirs.

And suddenly large portions of the document get rewritten… not because the meaning is wrong, but because the wording is different.

A party changes language because their template phrases it another way.

A newer attorney redlines provisions that rarely move in real deals but doesn’t yet have the experience to know that.

Someone applies a playbook without considering the commercial and economic context of the agreement.

In many cases, if a dispute ever reached a courtroom, the original clause and the revised clause would likely be interpreted the same way.

Or the potential increase in liability—one way or the other—would be minuscule.

But the markup process doesn’t care.

Once the redline appears, it demands a response.

And another round begins.

Momentum slows.

Not because anyone is protecting the company.

Because playbooks and templates are colliding.

Category 4 — The Pure Oxygen Burn

Then there’s the final category.

The one that quietly drives everyone insane.

Pure cosmetic edits.

“Shall” becomes “will.” “Promptly” becomes “without undue delay.” Paragraphs get reorganized.

Someone insists on removing the Oxford comma. Someone else insists on keeping it.

For the record, I’m vehemently pro-Oxford-comma.

But even I know that’s not the hill to die on in a contract negotiation.

These changes don’t affect how a judge would interpret the agreement. They don’t affect how the parties behave.

But they still trigger a full markup cycle.

Automation tools frequently amplify this problem (they do this in Category 3, too).

Run an agreement through a contract review system and suddenly half the document gets rewritten in the name of “consistency.”

And none of the changes are economically or legally meaningful.

Category Four edits consume oxygen without improving the deal.

Where Momentum Starts Disappearing

If negotiations contained only Category One and Category Two edits, most deals would move quickly.

Real issues would surface. Real decisions would get made.

But Categories Three and Four introduce something different.

Drag.

They create additional rounds that don’t meaningfully change the outcome.

Sales cycles stretch.
Internal teams spend time reviewing edits that don’t alter risk.
Relationships between the parties start to fray.

And everyone involved believes they’re simply doing thorough work.

The Discipline I Try to Apply

Over time, I’ve tried to discipline my own reviews using this framework.

Category One gets immediate attention.

Category Two gets thoughtful negotiation.

Categories Three and Four require restraint.

Just because I can improve a sentence doesn’t mean I should.

Just because a clause differs from my template or clause book doesn’t mean it needs rewriting.

And just because something I do is technically better drafting doesn’t mean the deal benefits from another round of markup.

Contracts exist to support transactions.

Not to become writing competitions.

Wrapping It Up

Redlines aren’t the problem.

Unfiltered redlines are.

Some protect the company. Some improve the agreement.

Many simply burn oxygen.

After thirty years of watching deals slow down for reasons nobody could quite explain, this four-category filter has become the simplest way I know to keep negotiations moving.

Next week I’ll focus on the structural side of the problem.

Because templates aren’t laziness.

They’re discipline.

And companies that standardize intelligently tend to close deals much faster than the ones that treat every agreement like a blank page.

Comment on LinkedIn.

March 3, 2026

Last week we talked high-level about the costs associated with redlining… and why economics should inform every negotiation decision.

This week, the altitude drops. Let’s do some math nobody wants to do.

An old deal has been resurfacing in my mind as we begin pressure-testing structural filtering with an early cohort. It’s the exact pathology we’re trying to eliminate.

A few years back, a $150,000 SaaS deal crossed my desk. I was vendor-side. It was the kind of transaction that should have closed in a couple weeks, max.

It took eight weeks and fourteen version exchanges. They send a redline. We respond. They respond to our response. Fourteen times.

Let’s put real numbers on what that actually cost… not abstractly. Two separate ledgers. Theirs and ours.

Their Ledger: The Cost of Acquisition

Their outside counsel was excellent. Senior partner. Large, global firm. Highly trained and very experienced... this customer was a large company and probably one of his key clients. By my estimate, roughly 50 hours invested across the life of the deal.

At $1,000 an hour, that's $50,000 in outside counsel fees.

On a $150,000 contract.

Thirty-three cents of every dollar they spent acquiring the right to use my client's software went to lawyers negotiating the right to acquire it.

Nobody ran that number. It showed up on an invoice, got approved, and got absorbed as "how deals work." Or maybe there was some sticker shock... I'll never know.

Our Ledger: The Cost of Delivery

Our side had three people in the deal: an AE, a founder/CEO, and me as kind of an "outside in-house" fixed-fee guy.

Start with gross margin. SaaS at 85% on a $150K contract leaves $127,500 before you account for what it cost to close it.

Then the costs nobody tracks:

The AE earned a $15,000 commission on close. That number showed up. What didn't show up is the recurring productivity tax of fourteen version exchanges over eight weeks. Every new version pulled him back in... re-read, re-brief, re-engage. He was still working his pipeline. But not without interruption. That cost doesn't have a clean number. It never does. It just shows up as other deals that moved slower than they should have or that couldn’t be handled at all. Pencil in $10,000 in lost revenue opportunity. It's a placeholder, not a precision instrument. But it's closer to the truth than zero.

My time: roughly the same 50 hours as the other side's attorney. I had a unique billing arrangement with this client, so for the sake of this exercise let's use a market outside counsel rate of $500/hour... a number that reflects experienced commercial counsel outside a major firm environment... not a big city rate... maybe with a discount for early-stage company work. Call it conservative. That's $25,000 on this deal. Half what they spent for the same hours and comparable experience.

Total quantified drag on our side: $50,000. With a CEO's time still unaccounted for.

Net-net on a $150,000 deal: $77,500. Fifty-two cents on the dollar.

Now do the math differently. The AE commission is fixed... you close the deal, you pay the commission. But the $35,000 in legal fees and lost revenue opportunity? That's process drag, not deal drag. With a process that actually works, those same costs drop to a tenth, if not less. $35,000 becomes $3,500. The commission doesn't change. The deal doesn't change. The process does.

That's $31,500 in recovered margin. Twenty-one points. On one deal. Because the process stopped being the problem.

And that's before you count what it costs when the founder has to stop building a company to unstick a contract negotiation.

The Costs Nobody Tracks

The $50,000 invoice on their side was at least visible. Ours was worse because it was invisible.

My hours didn't hit a matter management system. The productivity tax on the AE didn't show up on a dashboard. The CEO's time certainly didn't get logged against the deal.

It just... happened. And got absorbed. As "how deals work."

There's also what the calendar cost beyond the ledger.

Eight weeks of pipeline limbo. A deal that should have closed in weeks bled into month three. Forecasts shifted. Conversations got awkward.

By version eight, nobody on either side was enjoying this. The executives who eventually stepped in didn't do so because they wanted to. They did it because the deal had become a hostage situation. That's not a great foundation for a working relationship.

What Actually Drove the 14 Version Exchanges

It wasn't complexity. The issues weren't that hard.

It was a meaningful volume of Category 3 edits... preference... treated with the same gravity as genuine exposure items. Every clause got scrutiny, whether it warranted it or not.

The senior partner's mandate, as near as I could tell, was thoroughness over velocity. Thoroughness is admirable. Thoroughness without triage is how you spend $50,000 acquiring a $150,000 contract.

The Question You Should Be Asking

Before any redline goes out, someone should be asking: what does one unnecessary version exchange actually cost?

Not abstractly. Concretely.

If both sides are using outside counsel at $500/hour and a full exchange takes 1.5 hours per side, that's $750 per exchange. Three unnecessary exchanges on a $50,000 deal is $2,250... 4.5% of contract value for each side walking out the door before a single deliverable.

Every unnecessary exchange extends a sales cycle, burns legal hours, and pulls someone out of more important work. None of it tracked. All of it real.

Most teams never run this number. They just absorb the cost as "how deals work."

What This Tells Us About the System

The $50,000 invoice on their side didn't reflect $50,000 in value delivered. It reflected $50,000 in friction generated by a process that doesn't distinguish between what matters and what doesn't.

On our side, $50,000 in quantified costs quietly eroded a deal that looked like $150,000 into one that netted $77,500. With a CEO's time still unaccounted for.

That's not an indictment of the lawyers or the AE or the founder. Everyone was doing their job as the system defined it.

It's an indictment of the system.

When legal effort isn't calibrated to economic value, waste is the default. Not the exception. And it shows up on both sides of the table... one side on an invoice, one side as margin that quietly disappears.

The fix isn't to lawyer less. It's to lawyer smarter. To know, before the first redline appears, which categories of edits deserve oxygen and which ones don't.

That's what discipline looks like.

And discipline, in this context, is a revenue strategy.

This is why we’re pressure-testing structural filtering before the first redline ever appears. Because margin shouldn’t disappear quietly.

If 20+ points of recovered economics matters to you, you know where to find us.

Comment on LinkedIn.

February 24, 2025

A small deal crossed my desk recently.

Low value. Routine subscription. The kind of transaction that should glide from quote to signature without anyone breaking a sweat.

Our sales folks sent the order form that incorporated our standard platform terms. Commercial terms in one place. Legal stuff in another. Clean. Intentional. Boring in the best possible way.

It came back… heavily redlined.

Not a few targeted changes. Pages.

And not just tweaks to pricing or scope.

Edits to the uniform terms.

The kind of edits that quietly convert a scalable structure into a bespoke legal science project.

And of course they had converted a pdf into Word so everything was gorked beyond belief.

The internal question was predictable: “Do we even engage?”

The answer was also predictable (to me). No.

Not because the other side was outrageous. Not because I’m allergic to negotiation. Not because I enjoy saying no.

Because the legal oxygen required to unwind and debate those edits exceeded the economic value of the deal.

That’s not ego.

That’s capital allocation.

Legal Attention Is Capital

Most organizations treat redlining like a performance sport. The more edits, the more serious you must be. The more clauses moved around, the more “protected” the company supposedly is.

That’s comforting.

It’s also wrong.

Every redline costs something.

Time. Internal attention. Sales momentum. Reputation. Another email thread that nobody asked for. Another calendar slot that didn’t need to exist.

Legal attention is not infinite. It is capital. And capital should be deployed proportionally.

An $11,000 deal does not justify the same legal bandwidth as a $1.1 million deal. Pretending otherwise isn’t rigor. It’s rebuilding the bike frame when the chain just needed oil.

Reading a contract includes reading the room

Over time, I’ve found most requested changes fall into four buckets.

First, the rare ones: things you simply cannot agree to. Structural exposure. Risk you will not carry. These are few... very few. They matter.

Second, the defensible ones: changes that genuinely need adjustment based on deal value, solution type, or exposure profile. You can explain these to your business team and defend the time (and their money) spent. Leverage likely plays a role here.

Third, preference edits. You want it written differently. You have a clause book. You have your forms. You prefer your version of a clause because it “flows better.” These are common. Comfortable.

Fourth, cosmetic noise. Formatting. Language flourishes. Commas bravely repositioned in the name of justice.

Categories three and four are where momentum goes to die.

They look like diligence. They feel thorough. They function like drag.

In this case, what stood out wasn’t hostility. It was structural confusion.

Uniform platform terms were treated as if they were a fully negotiable, bespoke agreement. The proposed changes were of a nature that I’d (grudgingly) expect on a major, global deal with lots of zeroes.

That’s not malicious. It’s just undisciplined. The room… not read.

Not every document needs to be re-engineered on every deal. When you destabilize those without economic justification, you’re not being careful.

You’re burning oxygen.

And when legal burns oxygen on small deals, the business feels it instantly. Sales doesn’t experience this as diligence. They experience it as friction.

Momentum stalls. Credibility wobbles. The deal that should have been easy... suddenly feels heavy.

Legal discipline isn’t about being inflexible. It’s about having a rationale that outweighs the drag you’re about to create.

Before you redline anything, I implore you to ask two simple questions:

Is this a “cannot agree”… or am I just imposing preference? And does this deal justify the oxygen required to fight about it?

If you can’t tie the edit to exposure and economics, you may not be protecting the business… you may just be performing diligence for the sake of looking diligent.

We’re beginning to pressure-test what happens when this filtering happens before the first redline ever appears. When signal is separated from noise structurally… not emotionally.

Because discipline shouldn’t start after the redline.

Small group. Live deals. Real momentum on the line.

Apply for Beta here

Want to talk through it first?

Request a Call

Join the discussion on LinkedIn.

Stardate: February 12, 2026
Location: Final Approach

We’ve named the chaos. We’ve exposed the repetition. We’ve seen how the same human patterns show up inside the clauses.

Now here’s the real question: what changes when the deal doesn’t start with suspicion?

Because that’s the part we’ve all quietly accepted as normal. And that’s a friggin’ shame.

In the traditional world, the very first thing one side does is send “their paper.” It’s typically a draft that feels like a position disguised as a document. And the other side’s job is to defend themselves.

Trust doesn’t erode during redlines.

It erodes the moment that first draft lands in your inbox.

Shoulders tighten. Tone shifts. People start reading for traps, not understanding.

Because the structure of the process assumes we’re opponents.

Your paper. My paper. Hidden leverage. Strategic ambiguity.

That’s the starting gun.

Now imagine a different opening move

Imagine this: instead of sending “our paper,” you invite the other side to review a structured agreement built on a shared playbook—one that makes the decision zones visible. The flex areas surfaced. The common paths clear.

You’re not hiding your position inside paragraphs.

You’re showing your cards in the structure of the draft itself.

Before anyone reviews it. Before any edits start. Before a single redline exists.

The draft isn’t a move in a chess match.

It’s a signal.

A signal that says: we’re not trying to win by obscurity. We’re here to make decisions in the open.

Before a single edit happens, the tone is different.

The other side doesn’t feel like they’ve been handed a weapon. They feel like they’ve been handed a map.

What actually changes

Legal doesn’t enter the process as the brake pedal. Sales doesn’t lose credibility the moment “the contract” shows up. Business teams don’t throw deals over the wall and wait in the dark.

You don’t spend energy proving you’re tough.

You spend it deciding what matters.

The friction moves from syntax to substance. From ego to economics. From performance to problem-solving.

You still negotiate. Hard. If you have leverage and want to use it, go for it.

But you’re negotiating on the same terrain.

And that changes behavior.

People concede faster when they understand the landscape. Trust builds when motivations are visible. Momentum survives.

I'll admit, some people like the old dance.

They like obscurity. They like leverage through complexity. They like being the only one who “really understands the paper.”

I know this. I’ve met with them. And I hate to admit it... at times, I've been them.

Guess what? We’re not building for them.

Because those deals don’t age well. They crack under stress. They turn into disputes nobody wanted. And that's not what we're about at Transactency.

Fin

I’ve spent this series saying out loud what most people only complain about privately.

Now comes the part that matters.

Over the next few weeks, this stops being a thought experiment.

Real people. Real negotiations. Inside a structure designed to start with alignment instead of suspicion.

We’re about to see what happens when the dance floor changes.

If you’ve ever walked away from a deal thinking, “That was way harder than it needed to be…”

This is where the experiment begins.

Redliner’s Log… signing off. For now.

Ready to #TrustQuickly? Come on in. The water’s warm. We’re inviting a small group to pressure-test this in live deals and you can get in line here.

/M

P.S. - join the discussion on LinkedIn!

Stardate: February 3, 2026
Location: Clause Lab in Outer Nebula

We’ve been talking about repetition. About how the same fights keep showing up in different contracts.

So let’s zoom in.

Not on a deal. On a single clause. Limitation of Liability.

Of course.

Almost every commercial agreement has it. Every lawyer rewrites it. Every negotiation slows down when this one comes up.

But here’s what’s actually happening…

This clause isn’t just allocating risk.

It’s revealing how each side sees the world.

What This Clause Is Supposed to Do

On paper, it’s simple: if things go sideways, how much can each side lose?

Cap the dollars. Exclude certain damages. Carve out special scenarios.

Clean. Logical. Contained.

In theory.

What This Clause Reveals

In practice? It turns into a diagnostic tool.

Because there are really only a handful of structural positions that are typically taken by the parties:

Low cap, tight (or no) exclusions;
Moderate cap, perhaps with specials, with targeted carveouts;
Higher cap with broader exceptions; and
Very high or effectively uncapped in certain areas.

Same menu. Different wording.

But the way someone pushes on this clause tells you everything about how they operate.

The Over-Protector

This negotiator wants the lowest cap possible. No exclusions. Minimal carveouts.

Not because they’ve modeled the risk in detail.

Because their job, in their mind, is to eliminate downside at all costs. Even if the deal becomes commercially strained.

They are not negotiating the deal. They are negotiating their own exposure to blame.

The Deal-Momentum Optimizer

This one pushes for something reasonable, early.

Not because they don’t care about risk.

Because they understand delay has a cost. Lost momentum is a cost. Relationship friction is a cost. Sales matter.

They’re managing the whole equation, not just the legal variable.

Their question isn’t just “What’s the exposure?” It’s “What’s the exposure versus the value of getting this done?”

The Scale Player

Large, well-capitalized companies often push for higher caps and broader carveouts. From the other side, this can feel disconnected from the economics of the deal.

But the driver isn’t posturing.

It’s scale.

Risk doesn’t grow in a straight line for big companies. It compounds.

More customers. More data. More regulators. More publicity. More class-action exposure.

So when something breaks—a data breach, service failure, system outage—the downstream consequences multiply. The same incident that might be manageable for a small company can cascade into a multi-million-dollar problem at enterprise scale.

From their perspective, a cap tied to contract value often misses the point.

Contract value ≠ exposure.

The vendor is looking at the value of the deal. The enterprise is looking at the size of the blast radius.

Same clause. Two different risk models.

The Leverage Compensator

Weak commercial leverage. Strong legal posture.

They know they can’t win on price, scope, or commercial terms… so the fight moves to the contract.

The clause becomes a place to claw back control.

If they can’t shape the business deal, they shape the risk envelope.

What This Tells Us

Same clause. Same few structural options.

Wildly different motivations.

Most of the friction isn’t about the clause.

It’s about what the clause represents.

Risk tolerance. Internal accountability. Deal urgency. Organizational scale. Power dynamics.

But because the clause is buried in prose… we argue language instead of naming what’s actually happening.

We fight commas while the real variables stay invisible. And invisible problems turn into emotional fights.

A real playbook makes the landscape visible. It acknowledges that one size doesn’t fit all.

It surfaces the typical structural positions. It informs what each one protects. It advises when each usually makes sense. And it divulges what operational or economic reality usually drives it.

Suddenly, the conversation shifts from “Your language is unacceptable” to “We’re comfortable with X risk, not Y. Where can we meet?”

And once you see this pattern in one clause, you start seeing it everywhere.

Indemnities. Reps and warranties. Termination rights.

Same menu. Same drivers. Same dance.

But the real shift doesn’t happen inside the clause.

It happens before the negotiation even starts.

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,

Stardate: January 27, 2026
Location: Negotiation Groundhog Day

Let me describe a fairly typical commercial negotiation.

There’s a debate about liability caps. Someone pushes for broader indemnity. Reps and warranties come up. Termination rights get tweaked. Someone insists, “This isn’t standard.”

Now here’s the question: was I describing your last deal… or the one before it?

This is the part nobody says out loud.

We keep having the same fights. With different logos on the letterhead.

Different company. Different economics. Different explanation for why “this one is unique.”

Same arguments.

We act like each contract is a snowflake. But the negotiations run on a loop. The same clauses light up. The same concerns surface. The same fallback positions magically appear once “business urgency” enters the room.

And yet every time, we behave like this is groundbreaking legal terrain.

Why?

Because the system forces us to rediscover what we already know.

The knowledge lives in people, not in the structure. So every deal becomes a reenactment. Same script. New cast. Endless improvisation around the same plot points.

It’s exhausting.

And the worst part is how quietly that exhaustion spreads.

Sales teams start hedging earlier. Founders brace themselves before looping Legal in. Lawyers get pulled in later than they should… and blamed when timelines slip anyway.

Nobody says it out loud, but everyone feels it:

“This is where the deal slows to a crawl.”

So people adapt.

They avoid pushing back on business terms because they know the contract fight is coming. They rush early alignment because they’re saving energy for legal review. They start negotiating around the agreement instead of through it.

Not because they’re careless.

Because they’re conserving momentum.

That’s what repetition does.

It doesn’t just slow deals down. It trains smart people to adapt. Negatively.

They stop optimizing for good decisions and start optimizing for survival.

Once that happens, the contract stops being a tool for alignment. It becomes something you endure to get the deal done.

Yet we continue pretending the predictable parts are unpredictable.

So every deal starts from scratch. Every familiar issue gets re-negotiated. Every known outcome has to be rediscovered.

We redline. We posture. We signal diligence. We repeat the dance.

And nobody steps back to ask:

“Why are we still negotiating this like it’s 1997?”

The real cost isn’t legal risk. It’s momentum decay.

Deals slow down. Trust thins. Energy drops. The process starts feeling heavier than the decision it’s supposed to support.

Not because the deal is wrong.

Because the structure is. It’s rinse and repeat in the worst possible way.

I challenge you to disagree...

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Stardate: January 20, 2026
Location: Above the Fog. Visibility Improving.

I've spent the past few entries naming the chaos.

I've talked about the markup theater, the flex zones, the lack of alignment, the emotional toll of legal ambiguity, and the illusion of “winning” the redline.

Now it’s time to talk about the cure.

The Dirty Little Secret: We All Know the Playbook

Let’s start with some brutal honesty:

Most of us who’ve been doing this for a while? We know the playbook. Hell, we’ve written it.

We’ve sat on both sides of the deal table. We’ve represented vendors, buyers, founders, investors, employees, employers. We’ve argued every clause from every angle. We know where the real tension lives... and how it usually gets resolved.

Let’s not kid ourselves: there’s no grand mystery here.

There are only so many ways to handle a limitation of liability clause. Only so many indemnity configurations that actually make sense. Only so many paths through an IP ownership debate, or a termination provision, or a payment term dispute.

The reality is this:

We’re not negotiating new legal principles. We’re negotiating preference. And leverage.

So why are we still pretending each contract is a snowflake?

Why are we still dragging each other through the same performative markup dance… every… single… time?

What If We Didn’t?

What if we admitted what we all know?

That the majority of each contract is typically the same from deal to deal... and that it’s the minority that’s negotiable? It’s not chaos. It’s a pattern. A set of recurring decision points. A choose-your-own-adventure of dealmaking.

What if we stopped acting like every markup is a masterclass in bespoke risk negotiation…

…and just showed our cards up front?

Introducing: The Shared Playbook

Transactency isn’t a template. It isn’t a form. And it damn sure isn’t a “market standard” contract designed to lock you into someone else’s definition of fair.

We didn’t build a form. We built a framework.

The Shared Playbook is a transparent system for showing both sides the same map, up front.

It lays out:

• What kind of contract this is
• What the standard building blocks are
• Where the flex zones live
• What the common positions are within each flex zone
• Which positions tend to align with which business needs or leverage dynamics

Think of it like this:

A traditional form is a prescription. The Shared Playbook is a menu.

You don’t have to take the most neutral option. You can pick something stronger if you’ve got the leverage. You can accept something softer if you’re in sales mode. You’re not limited... you’re empowered.

The difference is that everyone sees the same choices.

No traps. No gotchas. No backloaded tricks hidden in clause 13.7(b)(ii).

Just structured visibility, and clarity about what’s really being agreed to... and why.

Optionality ≠ Weakness

Let’s pause on this, because it’s vitally important.

Some folks hear “multiple options” and get nervous. They think it means giving up control. Or inviting chaos.

Nope.

Offering choices isn’t weak. It’s stronger alignment because it invites real conversation.

You want the one-sided indemnity clause because you’re a regulated financial institution? Fine. Say that.

You want shorter payment terms because cash flow matters more than vendor sentiment? Cool. Put it on the table.

The Shared Playbook doesn’t tell you what to choose. It just shows the field you’re playing on... and removes the theater.

Because the theater isn’t helping anyone.

It’s Not Just for Legal

One of the biggest mistakes companies make?

They act like contracts are “legal’s job.”

They’re not. Contracts are business architecture. They’re a reflection of strategy, trust, and execution risk.

And yet, most founders, execs, and operators are locked out of the negotiation process.

Not because they lack opinions. Because they lack a translator. So they either punt to (or are held out by) those that speak the language (legal).

What the Shared Playbook does is give the whole team—legal, sales, finance, procurement, founders—a common language.

So everyone knows what matters, what’s flexible, what’s risky, and what’s normal.

This is where things get powerful.

Because now?

The redline isn’t just a legal artifact. It’s a collaborative workspace.

This Is How We Make Fewer Markup Cycles Possible

Remember earlier when we said the problem wasn’t the speed of redlines... it was the number of them?

The Shared Playbook solves that.

Because instead of reacting to surprises, we’re aligning on options.

Instead of rewriting boilerplate, we’re focusing on decisions.

Instead of playing “guess what they really want,” we’re working from a shared map.

This is how we cut out the noise and zero in on the signal.

It’s how we stop treating every deal like a game of Battleship.

This Isn’t a Fantasy. It’s Already Happening.

Some of the best legal teams in the world already do this, albeit in piecemeal fashion.

They have internal playbooks. They’ve memorized fallback positions. They’ve built clause libraries and redline battle plans.

But all of that knowledge?

It lives in inboxes. In brains. In disconnected templates and tribal wisdom.

Transactency just makes it visible. Sharable. Actionable.

And it opens that visibility to both sides, not just the folks with the biggest legal budgets.

Transparency + Understanding = Better Deals

Let’s revisit something from earlier:

Successful deals almost always share two ingredients:

1. The parties were transparent with each other. They stopped posturing and actually shared what they cared about.
2. The parties understood the contract. Not just what it said, but what it meant. What it required. Where the obligations were.

When those two elements are in place?

Deals don’t just close. They succeed. They last. And they don’t end in lawsuits or angry Slack threads nine months later.

Transactency is the only contracting platform designed to make both transparency and understanding the default.

Not just for lawyers. For everyone at the table.

Let’s Be Honest: The Old Way Isn’t Noble. It’s Expensive.

Pretending every deal is bespoke?

That might feel noble. It might stroke your ego. But it’s not a badge of honor. It’s a tax.

A tax on time. A tax on trust. A tax on your team's limited mental energy.

And here’s the thing: bespoke used to be the only option.

A hundred years ago, if you wanted a suit, you went to a tailor. Everything was custom… because it had to be. No off-the-rack. No sizing charts. No “close enough.”

Then we learned something important. Most of the time, we don’t need couture. We need something that fits well, looks good, and gets us out the door.

So we standardized many of the elements. Sleeves, seams, silhouettes, fabrics. We kept tailoring where it actually mattered… length, waist, shoulders. The result wasn’t worse clothing. It was better clothing at scale. Customization didn’t disappear; it got focused.

Contracts haven’t had that reckoning yet. We’re still treating every agreement like it’s headed for a Paris runway… when most of them are just trying to get to the office on time.

It's time to call it what it is: wasteful.

We’re not asking you to abandon nuance. We’re just asking you to stop reinventing it from scratch.

Let’s memorialize what we’ve already learned. Let’s codify what works. Let’s stop pretending every deal is art.

Let’s put down the red pen... and pick up the map.

Weigh in

If you were starting your last deal from scratch, which terms would you actually want to debate again?

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Stardate: January 13, 2026
Location: Flashback Subroutine Engaged. Pre-cloud, Pre-GenAI. Ancient WordPerfect Airspace.

So, we’re almost there. But before we change gears, let me tell you a story.

I was a young associate at a large, international law firm, still trying to find my rhythm, when I got staffed on a big deal. High stakes. Lots of zeroes. Lots of eyes. One of those “don’t screw this up” assignments.

Leading the charge was a senior partner—super well-known in the circles. Brilliant guy. Deep experience. Giant book of business. Total (and I mean total) command of the contract. Also? Loved to fight.

His approach was simple: if the other side didn’t cave on the majority of our markup—and we were going to modify every deal to match our gigantic, leveraged master form—we’d “lost.” We were to take the hard line. Move the other side’s position. Argue. Then argue some more. It was about control. About dominance. About making the paper reflect his superior intellect.

I took a swing at responding to the agreement we’d been provided. Back then, we were printing things out, scribbling in our notes and changes, and having our admins incorporate the changes into the Word doc. I worked the document, had multiple back-and-forths with the partner, and finally created a turn of the agreement to send to the other side. But first, it had to go to our client for their input and approval.

The markup looked like a crime scene. Red ink everywhere. Entire clauses DOA. Numbering and formatting reengineered because, quote, “it wasn’t proper structure.”

The client agreed with the changes. In so doing, they told us something I found (and still find, after all these years) amazing. The business folks on the other side had made an offer.

When they had learned that this partner was representing our client, they offered our client a huge discount if our client would agree to use literally anyone else as their lawyer.

They didn’t care who. Just not him.

Why? Because they’d dealt with him before on other deals. They knew he was going to make this as inefficient a process as could be imagined. They’d seen him crater transactions and over-leverage contracts because “he could.” It was worth cold, hard cash to them to avoid the waste of time, effort, and energy they foresaw coming.

The partner thought it was a compliment. He actually smiled.

I wanted to scream.

Unfortunately, our client thought it was great, too. Somehow, it stroked their ego as well. Then, after grinding out a deal over the course of several months that should have been measured in weeks, they got the bill. And they didn’t get much of a kick out of that. He hadn’t killed the deal—this time. But he did kill the budget.

The Fallacy of “Winning” the Redline

There’s a certain breed of deal lawyer (and we’ve all seen them) who thinks negotiation is a zero-sum game. That every deleted word is a victory. That their job is to “win” the markup.

Let me say this plainly: There’s no trophy for the most redlines. No leaderboard. No bonus points.

Clients don’t throw parades for lawyers who “dominate” the other side. They just want the deal done... on reasonable terms, without unnecessary carnage.

A contract is a partnership—it’s two parties trying to do business… together.

A scorched-earth markup doesn’t make you look smart. It makes you look insecure. Or worse: replaceable.

Redlines Are a Tool, Not a Scorecard

The purpose of the markup is to move the deal forward. To align on expectations. To create mutual clarity and trust.

If your redline is designed to show off, slow down, or sneak in traps? You’re not helping. You’re flexing.

And eventually, people notice.

Your client notices. The other side definitely notices. And the deal—if it closes at all —drags along a trail of resentment and wasted time.

This Is the Culture We’re Trying to Undo

The legal world is filled with these ghosts. People who think the game is about “winning the redline” rather than getting to “yes.”

Unfortunately, the current solutions out there (including GenAI) don’t fix this. They may make things move faster. But there are also folks who argue that they arm people like the partner in my anecdote to do even more damage.

Either way, we still face this problem.

At Transactency, we’re not here to shame the past. Hell… some of us were the past.
But we are here to build a different culture. One where negotiations are measured by usefulness, not volume. Where the goal isn’t to “win the redline”… it’s to close the deal with clarity, speed, and trust intact.

Back soon with Entry 3.1, where we start unpacking how a shared playbook can stop the madness before it starts.

Until then, may your markups be light… and your lawyers self-aware.

Weigh in

What’s the most ridiculous “redline win” you’ve ever seen… that ultimately cost the deal (or the budget)?

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Stardate: January 6, 2026
Location: Mid-flight over Negotiation Airspace. Debris fields from last markup pass still visible.

We like to think we’re being “strategic.” We say things like “let’s be thoughtful,” “let’s not rush,” “we want to be fair.” But when you peel back the layers, what most teams are doing during contract negotiations isn’t strategy. It’s improvisation.

We’re all flying blind—legal, business, founders, outside counsel—making it up as we go along and hoping to land in the same zip code. But when you don’t have structure, you don’t get alignment. And when you don’t have alignment, you don’t get deals.

Let’s talk about why.

The Myth of the “Smart Negotiator”

You’ve probably worked with one. Hell, maybe you are one. The person who can “read” the other side. Who claims to “feel out” a deal. Who talks about negotiation like it’s jazz... unstructured brilliance, solo improvisation, ego-driven artistry.

The truth? That might work once. Maybe twice. But it doesn’t scale. It doesn’t teach. And it doesn’t build trust.

Because what happens when the Smart Negotiator is out of office? Or too burned out to care? Or buried in seven other contracts?

The team flails. Deals stall. And your company bleeds credibility with every disjointed round trip of contract revisions.

Unstructured Collaboration Is Just Another Word for Chaos

Here’s what it looks like when structure is missing:

• Legal says one thing. Sales says another. Finance adds a last-minute condition.
• Outside counsel is redlining based on a doc they haven’t seen since last quarter.
• The business owner jumps in and rewrites half the agreement in plain English—which somehow contradicts the indemnity clause.
• The counterparty flags a “change” that was already in the template, and now everyone’s confused about who’s doing what.
• Version 4 turned into “Rob 22.23.25 Changes_1” turned into “Compare Rob to version 4.2” and no one knows which friggin' version is the current one.
• And of course, the “redlines on redlines” are starting to pile up, and you’re trying to figure out if that word is stricken, inserted, or both?

It’s not a negotiation. It’s a group project gone rogue.

Everyone’s working with different assumptions, different definitions of risk, and different visions of “acceptable.” And nobody’s wrong. They’re just not aligned.

The Real Cost of Chaos

This isn’t just a workflow problem. It’s an emotional and reputational one.

For the solo in-house lawyer: You’re already underwater. But now you’re fighting fires that shouldn’t exist, arguing over positions that should’ve been pre-aligned, clarifying things that should’ve been obvious.

For the SMB owner without in-house counsel: You’re bleeding hours and legal fees trying to figure out if the markup matters or not, all while your deal momentum slows and your budget takes a hit.

For both sides: Chaos breeds paranoia. And paranoia kills trust.

Every unexplained change, every unexplained delay... it doesn’t just slow down the deal. It casts doubt on the relationship.

Negotiation Needs Structure. Period.

Let’s define what I mean by structure.

I'm not talking about locking people into rigid scripts. I'm talking about building a shared framework that answers:

• What kind of contract is this?
• What are the standard components?
• Where do we usually see negotiation?
• What does “market” look like for each flex zone?
• What positions are acceptable vs. what’s a dealbreaker?

This isn’t theoretical. It’s how top legal teams already operate, but in their heads, in their inboxes, or in ad hoc templates.

I'm just saying: let’s make that system visible. Let’s codify it. Let’s stop making every team reinvent the wheel.

Structure Creates Speed.

When everyone knows where the real work is (and where it isn’t), they move faster.

No more arguing over formatting. No more wasted cycles on boilerplate. No more panicked calls about whether “industry standard” actually means anything.

It’s not that we avoid friction. It’s that we target it... to the places that matter. We get sharper. Smarter. More intentional.

And when that happens, deals don’t just move faster. They move with less pain.

There’s a saying in the U.S. Special Forces: “Slow is smooth. Smooth is fast.” Structure is kinda like that.

Structure Creates Safety.

Here’s a dirty little secret: most people in the deal process are afraid.

• Afraid of missing something.
• Afraid of getting blamed.
• Afraid of being the one who says “yes” to a clause that later blows up.

Structure changes that.

When your team knows what the fallback is… when the business owner knows what matters and what doesn’t… when your counterparty sees the same map you do… guess what?

You create psychological safety.

Not because risk disappears. Because expectations are aligned.

Structure Creates Trust.

If speed is the reward and safety is the protection, trust is the outcome.

Trust is what turns a redline into a collaboration. Trust is what gets your deal signed this week instead of next quarter. Trust is what gets the other side to tell you what they really need, not posture until the last minute.

And that kind of trust? It doesn’t come from charisma. It comes from clarity.

But here’s the part most teams miss: it’s not just about getting to signature. It’s about what happens after.

Because if you look at deals that actually work—the ones that don’t blow up six months later (or, as those of us of a certain vintage might say, those that stay in the desk drawer)—you’ll almost always find two things:

1. The parties were transparent. They had honest conversations. They skipped the posturing and got real about what mattered.

2. They understood the contract. Not just the general vibe, but the actual terms, the risks, the obligations, the edge cases.

That’s what sustains trust after the ink is dry. And that’s exactly what Transactency is built to deliver.

We don’t just help you negotiate. We help you understand what you’re agreeing to—and help your counterparty do the same. So you both walk away with eyes open, not crossed fingers.

This Is Why Transactency Exists

We didn’t build a legal tech platform to eliminate lawyers. We built it because even good lawyers are trapped in bad systems.

Our goal is simple: make structure the default. So founders, counsel, and counterparties walk in with the same map and get to “yes” without getting lost.

I’ll be back next week with Entry 2.5—a flashback to the kind of legal “strategy” that loses the deal before it starts. Because sometimes the problem isn’t the system; it’s the person who thinks they’ve already mastered it.

And from there, I'll start putting some shape around what actually works... the patterns, the playbooks, and the guardrails that make alignment possible.

Weigh in

What's your take on this? I'd love to hear your thoughts.
Join the discussion on LinkedIn

And check us out at Transactency for more info and to join our beta!

Stardate: December 16, 2025
Location: Low-orbit above Clause Cluster Delta. Multiple heat signatures around Section 9.

We need to talk about the battlefield.

Because let’s face it... redlines often feel like legal warfare. A barrage of comments, deletions, insertions, and passive-aggressive margin notes. Pages stained with “???” and “Unacceptable” like the modern-day equivalent of trench warfare.

But here’s the thing: most redlines aren’t actually about war. They’re about pattern recognition.

Every contract type—whether you’re negotiating a Master Services Agreement, a prenup, an equity investment, or a lease—has its predictable zones of friction. And once you’ve seen enough of them, you start to realize:

•  Redlines aren’t personal. They’re patterned.
• Only a few zones tend to get messy and matter. The rest is generally (annoying) noise.
• If you know where the tension lives, you can design for it.

Let’s unpack that.

It Only Looks Like Total Chaos

When you get your first redline back—or your 500th—it can feel overwhelming. Especially if you’re the founder who outsourced the template to a lawyer on Upwork, or the solo in-house looped in too late with a 24-hour deadline.

The markup looks like a massacre.

But most of it? Probably doesn’t matter. If only the other side could figure that out.

The other party added some defined terms that are used once. Changed “shall” to “will.” Replaced your header stylings with theirs. Fine. Annoying, sure. But not where the real risk lives.

Most of the time, there are select number of sections—or even sub-sections—that contain the real decisions. The pressure points. The forks in the road that determine how this deal actually balances risk and reward.

We’ve called those the flex zones.

Flex Zones Are Everywhere — But They Change with the Contract Type

Here’s where we’re going to depart from the usual “Top 5 MSA Clauses That Cause Pain” blog post. (No disrespect to those blogs… I’ve done that presentation too.)

The mistake most people make is assuming there’s one universal list of red flag clauses. But that’s only true within a contract category. Each contract type has its own playbook... and its own battlegrounds.

In other words:

• A commercial deal might center around indemnity, liability caps, and IP ownership.
• A prenup might hinge on division of assets, alimony triggers, or disclosure standards.
• An employment agreement might focus on non-competes, equity treatment, and termination for cause.
• An equity financing might get stuck on liquidation preferences, protective provisions, or voting thresholds.

So yes, every contract has flex zones, but they’re contextual. The art is knowing what kind of deal you’re in and which areas should be negotiable.

That’s the stuff that moves the needle. Everything else? Noise in a red font.

Why Redlines Get So Ugly Anyway

Even when both parties mean well, redlines can spiral.

Here’s why:

1. The system doesn’t differentiate substance from surface. Microsoft Word gives a markup for every comma, whether it affects risk or not.
2. People don’t know what matters, so they mark everything. Junior counsel marks things to look thorough. Founders overcorrect because they’re scared. Lawyers on auto-pilot redline by muscle memory.
3. There’s no shared expectation. If you’ve got no idea what the “norm” is for a particular clause in a particular contract type, everything feels up for debate.
4. One person’s best practice is another person’s nuclear red flag. Especially when companies borrow templates from other industries or pull out-of-context clauses from past deals.

Result? The redline becomes a battleground. Not because the two sides fundamentally disagree, but because they’re working without a map.

It’s Not About the Clause—It’s About the Context

Let’s be clear: no clause is inherently “bad” or “market” on its own. It depends on:

• The type of deal
• The risk exposure
• The economics
• The relationship between parties
• The power dynamic

A liability cap that’s outrageous in a $10K services contract might be standard in a $5M licensing deal. A non-compete that’s unenforceable in one state might be expected in another. A board observer right in a SAFE round might be eyebrow-raising—or totally routine.

Which is why generic guidance doesn’t help. You need:

• Context-specific defaults
• Pattern recognition
• A shared language for pushback

What Seasoned Practitioners Are Actually Doing

Whether they realize it or not, experienced negotiators follow a quiet internal system when they open a markup. It goes like this:

1. Identify the contract type. “This is an MSA / prenup / term sheet / employment offer…”
2. Scan for flex zones. “Here are the 3–5 places that usually move the deal… I give a shit about these.”
3. Compare the markup to the fairway. “Is this ask aggressive, conservative, or par for the course?”
4. Decide whether and how to respond to the important stuff. “Is this an actual risk, or just preference? Are we going to fight this, concede it, or propose a fallback? What’s my leverage? How badly do we need this deal?”
5. Scan the remaining changes. “I know these don’t really matter, but need to make sure the idiot making all of these extra revisions isn’t unwittingly blowing something up.”
6. Move the deal forward. “Let’s not die on a hill we don’t have to climb.”

This mental process is why experienced legal teams move faster—not because they’re better negotiators, but because they know where to look, how to prioritize, and how to process efficiently.

But Right Now, Everyone’s Flying Blind

The sad part? None of this is embedded in the system.

Inexperienced lawyers and general practitioners don’t know where the flex zones are. Some experienced lawyers “pretend” they don’t (and those, my friends, are the ones that trigger all the damn lawyer jokes…).

Founders negotiating deals themselves have no idea if the pushback they’re seeing is normal or nuclear.

And the redline itself? It gives no clue as to what’s important and what’s fluff. It’s just a soup of markup with no prioritization.

This is why deals stall. Not because people are bad actors (though they’re certainly out there). But because the contract lacks structure. The conversation lacks clarity.

And we’re all guessing our way toward “no.”

This Is Why Playbooks Matter

When we talk about building a shared playbook, we’re not saying every deal should follow a script. Far from it.

We’re saying: let’s agree on the map.

Let’s make it clear:

• What type of deal this is
• Where the expected pressure points are
• What the typical fallbacks looks like
• And where you might be entering outlier territory

That’s not dumbing down negotiation. That’s empowering smarter ones.

It removes the guesswork. It protects relationships. It speeds up time-to-deal.

And yes... it cuts down on unnecessary redlines.

Redlines Aren’t the Problem. Misalignment Is.

So here’s the real insight:

• The redline isn’t evil. It’s just the signal that something’s unclear (or, perhaps, misunderstood).
• If we can name the zones of tension, we can navigate them intentionally.
• If we systematize that navigation, we get better deals—faster.

It’s not about taking lawyers out of the room. It’s about giving everyone—lawyers, founders, and business teams—a shared framework to work from.

Because it’s a hell of a lot easier to get to “yes” when we all know what matters.

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Stardate: December 9, 2025
Location: Entering the Contracting Gameboard. Expect delays at Indemnity Junction and Limitation Loop.

You’ve seen it. A sales team swears the deal is done... “we just needs legal sign-off.” A business owner forwards a PDF at midnight with a hopeful, “Can you just bless this real quick?” Or the in-house attorney is handed a fully baked agreement… after the price is already locked, timelines committed, and half the deliverables promised.

And then things slow to a crawl. Redlines. Confusion. Frustration. “What’s legal’s problem?” And before you know it, that “done deal” becomes another ghost in the pipeline.

Why? Because nobody understands the gameboard.

Contracting Isn’t a Blank Page. It’s a Gameboard

Contrary to how it feels, contracting isn’t improvisational jazz. It’s a board game—with recurring players, predictable moves, and well-worn traps.

But most people (especially business folks without legal backgrounds) don’t realize this. They think every contract is a new battle. A fresh negotiation. A bespoke performance.

It’s not.

Whether it’s an MSA, an executive employment agreement, or a prenup, the underlying structure is familiar. We’re just not naming it. Which is why most people wander in unarmed.

Let’s Break Down the Players

The Solo In-House Counsel
Overworked. Under-resourced. Often looped in way too late. They’re expected to be deal doctor, risk sponge, and PR scapegoat... all while moving fast and saying yes. They know the hotspots. But without structure, they’re stuck arguing the same points over and over… or forced to roll over just to keep things moving.

The SMB Owner or Operator
No legal team. Outside counsel is $500/hour—and that’s for the junior associate. They either:

• Avoid legal altogether and hope nothing blows up;
• Google/ChatGPT their way through a redline; or
• Hire help too late—usually once a dispute or bottleneck shows up

In both cases, the result is the same: nobody’s playing the game strategically.

Because nobody knows where the pieces are.

Where We Actually Get Stuck

Despite all the posturing, most contracts don’t fall apart because of major disagreements. They fall apart because people are solving the wrong problems. Or solving the right problems in the wrong order.

Let’s map the terrain of some common clauses you might see, for example, in a commercial agreement:

• Limitation of Liability: “You break it, you buy it.” But how much? And for how long? Or is there even a limit at all?
• Indemnification: The contractual version of “you screwed up and you’re going to make me whole.”
• Termination Rights: What happens when the honeymoon ends?
• IP Ownership: “Who owns the work product?” should not take four rounds to figure out.
• Payment Terms: Cash flow matters. So do penalties, withholdings, and invoicing cycles.

These zones come up again and again in commercial contracts. Very, very frequently.

They’re some of the flex zones in commercial deals from our chili analogy in Entry 1.4. They’re not random; they’re inevitable. And if you’re not ready for them, you lose time, leverage, and momentum.

The Real Problem Isn’t the Clause. It’s the Misalignment.

Let’s take a typical example: a sales rep promises a 30-day implementation. The agreement, once reviewed, has a 90-day payment holdback clause. Legal redlines the hell out of it, because the implementation risk is too high.

Now Sales is frustrated, Legal feels like the bad guy, and the customer is stuck waiting while the internal teams bicker.

This isn’t a drafting issue. It’s a failure of shared visibility and shared assumptions.

And the Tools We Have? Not Helping.

Contract platforms aren’t built to teach contracting. They’re built to store documents, track versions, or (maybe) automate templates.

They don’t show:

• What the typical fallbacks are;
• Why Legal flagged a term; or
• Where the deal risks actually lie

So everyone keeps doing the same thing: marking up, emailing around, making assumptions, and hoping for the best.

That’s not negotiation. That’s Groundhog Day... with redlines.

Teaching Point: Contracting Is a System. But We’re Acting Like It’s Ad Hoc.

Everyone is operating off gut feel and tribal knowledge. There’s no shared playbook. No visual gameboard.

But that doesn’t mean the game doesn’t exist. It just means most of us are losing it without realizing why.

Here’s What Needs to Change

1. Acknowledge the Gameboard. Most deals get stuck in the same places. Map those places out. Expect them.
2. Loop in Legal Early. Not just to flag problems, but to avoid them before they start.
3. Give SMBs Tools, Not Just Templates. Most SMBs aren’t trying to avoid risk, they’re trying to avoid cost. Give them structure and process, not boilerplate.
4. Align Before You Redline. Contracts shouldn’t be the first place you discover a misalignment with the other party on scope, ownership, or risk.

Wrapping it up

The chaos isn’t random. And when you know where the fire starts, you can stop fanning the flames.

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Stardate: December 2, 2025
Location: Outer Rim. Legal out of comms range. Business decisions being made without cover fire.

Let’s talk about what happens when legal isn’t there.

Sometimes it’s because the team’s stretched too thin. Sometimes it’s because leadership thinks the lawyers will just slow things down. Sometimes it’s because there isn’t a lawyer at all—just a business owner with a red pen and a prayer.

No matter the reason, the result is almost always the same:

• Contracts get signed without a clear understanding of the risks.
• Issues that could’ve been resolved in minutes metastasize into weeks of back-and-forth.
• And the deal gets way dumber, slower, and riskier than it needed to.

And here’s the kicker: most people think they’re being efficient by leaving legal out.

The In-House Solo: Drowning in Redlines, Missing the Meeting

If you’re the lone in-house counsel, you already know the feeling.

You want to be strategic. You want to be proactive. But instead, you’re buried in inbound:

• Another one-off vendor NDA.
• Another 20-page redline from a partner’s “legal guy.”
• Another request to review a contract that starts with, “I know we need this signed today, but can you take a quick look?”

You miss the kickoff meeting. You miss the pricing call. You miss the moment where business terms shift—and suddenly the risk profile of the whole deal changes.

So when the contract finally hits your desk, it’s full of landmines you didn’t plant and can’t easily defuse. And guess who gets blamed for the delay?

The SMB Owner: Avoiding Legal (and Paying for It Anyway)

Now flip it. You’re a founder or small business owner.

Legal is expensive. You don’t have in-house counsel. You’ve got a law firm on speed dial, but every six-minute increment costs you dinner.

So you try to go it alone.

• You borrow a template from a friend.
• You copy terms from a past deal.
• You cross your fingers that indemnification means what you think it means.

And sometimes, it works.

But when it doesn’t? You don’t find out until it’s too late:

• That exclusivity clause you skimmed? Now you’re locked out of a new opportunity.
• That “termination for convenience” right you didn’t notice? They just used it—3 months into a 36-month deal.
• That unlimited liability you didn’t cap? It’s now a line item on your P&L.

And what’s wild is this: you’re not reckless. You’re just trying to get shit done without burning $750/hour every time someone sneezes on a contract.

The Common Thread: Legal Becomes a Reaction, Not a Strategy

Whether you’re solo in-house or flying without a net, the root problem is the same: Legal is being looped in reactively, not strategically.

And that delay? It causes friction.

• Because risks aren’t flagged early.
• Because terms don’t align with internal policies.
• Because the business makes commitments legal wouldn’t have signed off on and now it’s a mess to unwind.

This isn’t about ego. It’s about order of operations.

When legal starts on the back foot, the whole team ends up tripping over itself.

The Myth of “We’ll Just Clean It Up Later”

This one’s especially common in founder-led deals: “Let’s just get the deal done. Legal can true it up after.”

No. No, it can’t.

Because by the time the deal’s done:

• The leverage is gone.
• The urgency is gone.
• The willingness to renegotiate is very gone.

And if you think fixing bad terms later is cheaper than preventing them now? I’ve got a bridge, an arbitration clause, and a six-figure dispute resolution budget to sell you.

What We’re Really Talking About Is Systemic Support

Here’s the truth: legal doesn’t need to be in every meeting. But its perspective does need to be baked in from the start.

That means:

• Shared playbooks that reflect known risk tolerances.
• Tools that surface the common “flex zones” before anyone starts editing.
• A structured way for business users to flag, escalate, and understand legal redlines... without always needing to escalate to legal.

Because when you can see the issues early, you can solve them early. And early fixes are fast fixes.

No One Wants to Be the Bottleneck

Let’s be real: that “single-person legal department” doesn’t want to hold things up.

And business owners don’t want to take on unneeded risk.

They’re both doing what they think is best, but with limited resources and limited visibility.

The fix isn’t to push legal out. It’s to bring legal in earlier—through smarter tools, shared frameworks, and better defaults.

That’s not just more efficient. It’s more human.

Because nothing builds trust like clarity. And nothing kills trust like last-minute surprises.

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Redliner’s Log – Entry 1.4

Stardate: November 25, 2025
Location: Entering Sector 7: Clause Nebula. Instruments picking up mild turbulence around Limitation on Liability.

Let’s talk chili. Because I love me some good chili. I know, I know—turkey is coming in a couple of days... but work with me here.

Hopefully, you’ve seen some cooking shows (Iron Chef could easily merit an entire diary entry of its own here 😁). Having watched them, you’d know that, among other things, they usually contain some type of massive, stainless-steel, dream pantry filled with every spice, protein, and obscure root vegetable known to man.

We’re talking freaking ridiculous. In a great, great way. And the pans... don't get me going on all of the pans they get to use....

Focus, Denker. Focus...

So let’s say you want to make chili. Cool—go grab your ingredients from our awesome pantry.

That pantry? That’s the universe of clauses that can be assembled into any kind of contract.

The chili? That’s your agreement... for example, a Master Services Agreement (MSA). It’s comprised of ingredients—of clauses.

A contract, at its core, is just a deliberate mix of clauses drawn from a massive pantry, selected for purpose, context, and flavor.

Change the core ingredients? You’re no longer making chili—now you’ve got beef bourguignon, or maybe a fettuccini alfredo. Same goes for contracts: change the mix of clauses and suddenly your MSA turns into a prenup or an asset purchase deal.

This is the first big insight seasoned practitioners carry in their heads (whether consciously or not):

Contracts aren’t magic. They’re recipes. Different deals call for different dishes. But every dish starts with a basic structure. It has a list of ingredients.

The Flex Zones

Now, here’s the twist.

While every chili has a common foundation (maybe tomatoes, onion, garlic, chili spices) there’s always a zone for experimentation. Beans or no beans (don’t get the Texans going). Spicy or mild. Ground beef or turkey.

Same thing happens in contracts.

Certain sections in certain agreements are almost always tweaked or negotiated. In an MSA, for example, you might find that there are different stances frequently taken on:

• Limitation on Liability
• Indemnification
• Warranties
• Payment terms
• Termination and renewal
• IP rights

In a prenup, they will be different areas. And in an employment agreement, other areas as well. These are your flex zones—the places where two parties typically may have some differences and have to align expectations, assign risk, and make tradeoffs.

They’re not random. They’re predictable. And, for the sake of discussion, let’s say they typically make up 30% or less of the agreement.

The rest? The 70% base layer? If you’ve done a bunch of deals, you know that it rarely changes. Sure, folks might use different synonyms or have their own particular writing idiosyncrasies, but the substance of this base layer is typically the same deal-to-deal.

It’s not that this base layer is unimportant—it’s just not where the energy belongs. But that’s not how most deals play out.

Instead, we get the scattershot markup, the full-document bloodbath, the 30-comment response to a three-page NDA.

Because the system doesn’t distinguish between base and flex. It treats everything as a potential battleground.

Here’s what that costs:

• Time: Every roundtrip over a “typically agreeable” term delays the deal.
• Trust: Excessive edits signal suspicion or posturing, not partnership.
• Momentum: When everything looks like a hill to die on, nothing gets prioritized.

And that’s the second big insight:

Most contracts have a finite list of “real” negotiable areas—and it’s smaller than you think. But we treat every clause like it’s equally negotiable.

What’s in the Fairway?

Every chili competition has judges—hell, even if you’re over at the neighbor’s grabbing a bowl, you’re going to be unconsciously determining whether the chili is “good”.

Even if preferences vary, there’s still a norm—a range of flavor, spice, and consistency that says, “Yeah, this belongs.”

Contracting’s the same. In every negotiation, practitioners are silently comparing the markup to an invisible standard:

• “Is this limitation of liability market?”
• “Are these indemnities aggressive?”
• “Do we usually see this much termination notice?”

The problem is, most of that comparison is subjective. But we have to do it if we’re judging risk in a contract.

We rely on anecdotal memory, gut feel, and war stories from prior deals. There’s no central scoreboard. No framework that says, “Here’s where 80% of deals land. Here’s the outlier territory.”

Which means:

• Some teams negotiate from outdated or outlier norms.
• Others shoot for “market” without knowing where the market actually is.
• Both sides lose time rediscovering what experienced practitioners already know.
• And you’re sure as hell not going to be agreeing out of the gate.

But that’s changing.

The future isn’t about less negotiation. It’s about anchoring that negotiation in objectivity.

That’s the third big insight:

There’s a “fairway” for most terms. We just haven’t made it visible. And it’s guiding your judgment whether you know it or not.

The Way Contracts Actually Get Reviewed

As the second installment of Wicked is dropping, let me give you a little peek behind the curtain, so-to-speak. Here’s what seasoned professionals are doing (whether they realize it or not) when they are either drafting an agreement or reviewing a markup:

1. We make sure the pieces are in place (this is kind of a given... but we make sure this MSA is "actually" an MSA). Are the requisite clauses needed for an MSA present here? Is it structured like something I’ve seen before?
2. We identify the flex zones. Where are the areas where I find myself negotiating time and time again? What are the areas where deals may differ based upon underlying factors such as price, size, etc.? What is typically negotiated (versus what is generally the same deal-to-deal)?
3. We check or establish the flavors. How are these flex zones to be handled? Aggressively? Conservatively? How do they compare to what I typically see? How do they affect my risk? Do the economics justify the position? Does something else?
4. We negotiate with intent. Focus on the areas that matter—the flex zones. If I push back, why? Is it preference, policy, or precedent?

This process isn’t mystical. It’s not about being a genius deal-whisperer. It’s pattern recognition. Experience. Muscle memory.

In fact, some folks get smart and document this process—you’ll find their output commonly referred to as a “playbook”. Identify the areas you care about. Consider your alternatives. Act accordingly.

For too long, we’ve left this knowledge locked in individuals rather than embedded in systems.

Which means:

• New lawyers fly blind.
• Small companies overcorrect.
• Big deals slow down while people reinvent the wheel.

That’s a huge part of the dysfunction.

The Role of Tools

Let’s be clear: tech isn’t going to negotiate the deal for you (though some proponents of GenAI may argue with that, and that’s a whole different discussion).

But what it can do—what it should do—is help surface these insights before you start editing:

• What kind of contract is this, really? Does it have the requisite components?
• What and where are the known “zones of negotiation” for this type?
• Where does this version fall with respect to the positions taken in these flexible areas? What are other positions on these areas that I can reasonably take?

That’s the power of structure. That’s the promise of transparency.

Not to dictate terms... but to clarify the terrain.

So both sides can walk in with eyes open and energy focused.

Wrapping it up

This diary isn’t about turning lawyers into line cooks. It’s about naming the process that already exists… and making it visible to everyone.

The best practitioners aren’t smarter. They’re just more intentional.

They know what to look for. They know where to focus. And they know how to separate seasoning from substance.

What if we gave everyone that ability—before they’ve logged a decade in the trenches? What if we turned experience into a system?

Hmmmmmm....

And to all of my US-based friends, have a safe and happy Thanksgiving!

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Stardate: November 18, 2025
Location: Orbiting Risk Aversion Station. Shields up, progress down.

We say it’s about being safe. We say it’s about protecting the company. We say it’s just how deals get done.

But deep down? We know something’s off.

I’ve watched more deals get slowed down by misdirected caution than by real, material risk. I’ve seen teams burn cycles marking up language that wouldn’t hurt them while leaving the stuff that could untouched. I’ve seen trust erode not because anyone was hostile… but because the system nudged them to act like adversaries from the start.

And I’ve come to a frustrating conclusion.

We’re not too careful. We’re just careful at the wrong times and in the wrong places.

The Illusion of Safety

Let’s be honest: most legal departments aren’t rewarded for helping the business move forward. They’re rewarded for avoiding blame.

So the incentive becomes over-indexing on edge cases. Pad the protections. Mark up anything that might be misinterpreted.

But here’s the thing. Every extra layer of protection adds a layer of friction... and not all friction is worth it.

A clause that’s “standard” for one party feels aggressive to another. A markup that feels “typical” in isolation creates tension when viewed in context.

The result? Deals stall not because the risk is high… but because the system is misaligned.

Legal Caution Isn’t the Problem; Misdirected Energy Is

I’m not anti-legal. Hell, I am legal.

I’ve spent decades doing the work:

• Reading every clause.
• Thinking through downsides.
• Figuring out alternatives.
• Contemplating negative outcomes.
• Protecting the company.

This isn’t about being less careful. It’s about being smarter about where we aim our scrutiny.

Because what I see now is this: we’re applying deep legal rigor… to the wrong areas of the contract.

Meanwhile, the things that truly move the needle—the business terms that make or break the deal, the real liability exposure, and the issues seasoned lawyers actually care about—end up buried in the flotsam and jetsam.

We’re not under-lawyering. We’re over-lawyering the noise—and under-serving the signal.

“We Just Want to Be Thorough”

This is the line I hear over and over. And on its face, it’s reasonable.

But the real meaning is often: “We’re not sure where the landmines are, so we’re going to treat everything like a minefield.”

So the redlines pile up. The “suggestions” become demands. The clause-by-clause tug-of-war begins... even if the parties would’ve agreed on 90% of it from the outset if they’d just seen each other’s cards.

It’s not malicious. It’s the system.

When Playbooks Don’t Align, the Gloves Come Off

Here’s the root issue.

Both sides come to the table with their own playbook (whether actual or in their heads).

They’re not evil. They’re just different:

• One values flexibility, the other certainty.
• One has a strict indemnity policy, the other doesn’t even use the term.
• One has 10 lawyers. The other is a founder reading contracts at midnight.

And because those playbooks live in silos (and because our current tools don’t help bridge them), we start negotiating in the dark.

We don’t explain where we’re coming from. We don’t show our reasoning. We just start slashing and commenting.

It’s no wonder the other side reacts defensively. They think we’re being aggressive when we’re really just playing out our defaults.

The tragedy? We probably weren’t that far apart.

Legal PTSD Is Real—But It’s Not the Whole Story

Yes, some of this comes from past scars.

We’ve all had that clause come back to haunt us. We’ve all seen what happens when ambiguity bites back. We’ve all been second-guessed by someone with hindsight and a louder voice.

So we react. We “protect” more. We redline earlier. We strive to make things airtight for our side. And airtight becomes airtight and adversarial.

But not every contract is a landmine. And not every deal partner is out to exploit ambiguity.

The system assumes the worst and trains us to act accordingly.

What If We Started With Transparency?

Here’s the shift that changed how I think:

The problem isn’t too many redlines. It’s that no one agrees where the redlines should go.

What if both sides walked in with the same structural understanding?

• What’s standard.
• What’s often negotiated.
• What the options are for those terms that are negotiated.

Not hiding positions. And not pretending there’s only one “right” answer. Just putting the shape of the deal on the table... clearly.

Suddenly, negotiation becomes faster. Not because we care less. But because we’re clearer on where to care more.

That’s not reckless. That’s efficient. And respectful. And way more likely to lead to “yes.”

This Isn’t About Blame. It’s About Better.

The adversarial instinct didn’t come out of nowhere.

We built it over decades of misaligned incentives, performance-based lawyering, and fear of getting burned.

But it’s costing us.

Time. Trust. Talent. The emotional tax of going ten rounds over language no one actually enforces.

And the fix? It’s not magic. It’s structural transparency.

Start both sides on the same page... literally. Clarify where alignment usually happens. Show the tradeoffs in the places that differ.

Still negotiate. Still advocate. Still protect.

But do it from a place of understanding, not suspicion.

Wrapping it up

This diary isn’t about throwing legal under the bus. It’s about helping legal and business work better together.

We’re not asking for fewer lawyers. We’re asking for fewer redlines that don’t serve a purpose.

I’m still a lawyer. I still defend positions. I still care deeply about getting the contract right.

But now? I care even more about making sure we’re fighting over the right things... and are aligned on what “right” even means.

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Let’s keep going.

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Stardate: November 11, 2025
Location: Still stuck in orbit around Legal Review Planet. No signs of intelligent markup.

We talk a lot about risk in contracts. Risk mitigation. Risk allocation. Risk transfer.

But let’s be honest: half the time, it’s not about risk. It’s about reputation.

“If I don’t redline this, they’ll think I missed it.” “If I push back, I’ll look smart.” “If I don’t, I’ll look soft.”

And so the pen gets picked up. Not to clarify. Not to protect. But to perform.

We’ve all seen it—the hyperactive markup from the junior associate trying to impress a partner. The overly aggressive in-house counsel trying to “earn their seat at the table.” The vendor-side lawyer who knows this clause won’t survive, but marks it anyway to keep the power dynamic in check.

I’ve been that person. And I’ve worked with dozens of them.

It’s ego. With a law degree. And a red pen.

You Redline, Therefore You Are

In some corners of the legal world, if you’re not redlining, you’re not adding value.

Silence is risky. Acceptance is weak. So we perform.

Even if the clause is fine. Even if the risk is theoretical. Even if the change slows the deal to a crawl.

I once had a co-counsel who wouldn’t let anything go untouched. If a clause had the word "expeditiously," he'd change it to "without undue delay." If it said “shall,” he’d make it “must.” He was, in his words, “maintaining leverage.” In mine? He was bleeding momentum.

Okay, I'm exaggerating a bit here, but you get the point.

It didn’t matter what side he was on. Buyer, seller, licensor, licensee… didn’t matter. He needed to be seen doing something. To justify the retainer. To "win" the internal meeting. To “protect the company.”

But in reality? He was protecting his image.

The Hidden Cost of Legal Theater

Here’s the part that rarely gets discussed: redlining for ego isn’t just annoying; it’s destructive.

It erodes trust before a relationship even begins. It creates adversarial energy in deals that should be collaborative. It wastes time, burns budget, and often forces the businesspeople to clean up the mess.

I’ve watched what should’ve been a one-week contract turn into a four-week slog because a single attorney refused to back off on some issues that didn’t even apply to the deal at hand.

The irony? He didn’t even understand the business model. He just didn’t want to look like he’d “missed something.”

So we circled. And postured. And eventually closed… weeks late and emotionally drained.

When the Playing Field Tilts

Sometimes, uneven power dynamics aren’t about size. They’re about experience.

Years ago, I worked on an M&A deal where the opposing counsel wasn’t an M&A lawyer. He was a generalist—solid guy, smart guy—but his background was mostly residential real estate closings. This wasn’t his terrain.

Now, here’s the kicker: we knew each other. Well. He’d actually coached my soccer team when I was a kid. Small world.

But that familiarity didn’t help. In fact, it probably made it worse.

He didn’t want to look like he was in over his head in front of his client—particularly to a "kid he used to coach."

So he postured. Hard. Redlined aggressively. Took stances that didn’t make sense. Dug in where there was no need.

I don’t think he meant to derail the deal. But the result? A slow, frustrating, ego-fueled slog. Every step was harder than it needed to be… not because of substance, but because of perception.

That’s the danger of the uneven playing field. Not just imbalance, but insecurity masquerading as strength.

Legal as Proxy Warrior

Sometimes, this redline dance isn’t just about ego; it’s about businesspeople outsourcing confrontation.

Rather than say, “We’re not comfortable with this,” they hand it to legal.

“You be the bad guy.” “You make them sweat.” “You send the message.”

And legal obliges.

They fire off dense markups, sprinkle in a few “non-standard” notes, and the relationship shifts.

Now it’s not two teams trying to do a deal. It’s two firms fighting over turf. In Microsoft Word.

When legal becomes the weapon, the deal stops being the goal. Winning does.

And Still… We Keep Doing It

Even now, with all the tech, templates, and shared forms in the world, we’re still stuck in the theater.

Because it’s not a tooling problem. It’s a culture problem.

We’re still rewarding the performative lawyer. Still valuing the “strong markup” more than the clean close. Still confusing caution with competence.

It’s no wonder contracts have become slower, costlier, and more painful to negotiate. We’ve prioritized posture over progress.

Wrapping it up

This diary isn’t about blaming lawyers. It’s about naming a behavior we’ve all witnessed… and, if we’re honest, participated in.

The legal world isn’t full of bad actors. But it is full of incentives that make smart people do counterproductive things.

I’ve done them. I’ve watched them. And now I’m ready to stop.

We don’t need less legal. We need less performance.

Weigh in

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Stardate: November 4, 2025

Location: Still stuck in orbit around Legal Review Planet. No signs of intelligent markup.

The Theater of the Redline

A revised contract lands in your inbox. It’s bloody with redlines.

The other side rewrites the definition of “trade secrets” even though it’s already defined by federal law. They tweak terms that don’t need tweaking. A comment pops up: “Can we clarify this?” Another adds, “This isn’t standard.” Then come edits that subtly reshape your entire business model.

Track changes on. Curtains up.

It’s not risk mitigation. It’s not diligence. It’s posturing.

We call it “negotiation.” But half the time, it’s theater.

And most of us are stuck acting out scenes we never auditioned for.

A Real Example (Because You Can’t Make This Up)

Several weeks ago, I received an email from a member of a procurement team that perfectly captures how far we’ve drifted from common sense:

(Redacted for confidentiality)

Thank you Mike for providing the [draft agreement]. I have added it to my to-do list for review and redlining. Once I have completed my review, I will forward it to the [redacted] legal team for their assessment. After they have finished their review and returned it to me, I will send it back to you.

Please note that my review process involves a thorough, section-by-section and word-by-word analysis, during which I will integrate our own [form agreement] terms (which span over 60 pages). This step typically takes about 7–10 days. The legal review can take an additional 7–21 days, so the total turnaround time is generally 14–30+ days.

If you believe it would be faster for me to send you our [form agreement] for you to incorporate your [draft agreement], please let me know. I am comfortable with either approach, but traditionally, negotiations tend to move more quickly when using our standard agreement.

Have a wonderful weekend and we’ll talk next week.

That’s 14–30+ days to steer us toward “no.”

Not because anyone’s trying to kill the deal. But because we’ve let the process become more important than the outcome.

The Emotional Cost No One Talks About

We obsess over legal risk. But we ignore the real risk:

• The deals that die in limbo.
• The momentum that quietly vanishes.
• The trust that evaporates with every delay.

I’ve seen founders give up out of fatigue. I’ve watched promising partnerships dissolve in silence. I’ve been the one sitting on a call, trying to salvage goodwill after yet another “legal loop.”

Every unnecessary markup introduces friction. Every comment sends a signal: we’re not aligned. Every delay makes everyone a little more exhausted.

This is the hidden cost of redline theater. And we almost never call it out.

Why It Still Happens

If you’ve ever asked yourself, “Why are we still doing it this way?”, you’re not alone.

But the reason it persists is pretty simple: nobody wants to be the one who didn’t “do their part.”

We’ve trained whole teams to believe that marking things up is synonymous with adding value. That if you don’t comment, you didn’t contribute. That if you accept a draft too quickly, you weren’t “thorough enough.”

So people reach for the red pen—even when they have nothing to say. Just to prove they were here. Just to signal diligence. And the cycle continues.

What Finally Broke Me

I’ve been on every side of this mess.

As counsel, I’ve redlined to “show value.” As a founder, I’ve watched deals rot in inboxes. As a COO, I’ve seen business teams wait on legal like they were stuck in line at the DMV.

For years, I thought this was just how it worked. Then I realized: this isn’t a cost of doing business. This is the cost... and it’s far too high.

We don’t need another AI tool to redline faster. We need fewer redlines in the first place. We need a shared structure. A common playbook. A way to say: “Here’s how we do it. Tell us where you disagree.”

That’s how trust is built. That’s how deals close. And that’s why I started building Transactency.

But this post isn’t a product pitch. It’s (hopefully) the beginning of a discourse.

Me putting my thoughts down on (digital) paper—as whacky and blunt as they may be—capturing 30 years in the game, offering maybe a little hard-won wisdom. Or at least some thoughts worth thinking. And you? Providing your input. Righting me where I’m wrong. Calling me out when needed.

What This Is

This diary is for the ones who know the system's broken but have kept playing their part. For the people who’ve sent comments they didn’t believe in. For the ones who’ve watched a deal stall and thought, “There has to be a better way.”

I’ve been there too. I’ve carried the frustration. I’ve done the dance.

Now I’m ready to change it.

This is Entry 1.1. And where we’re going will be equal parts confession, cry for help, and exploration of where we might go next to solve this mess. We’ll spend a good chunk of time going through the problem; later, we'll discuss how we might solve it together.

What's your take on this? I'd love to hear your thoughts. Join the discussion on LinkedIn: https://www.linkedin.com/feed/update/urn:li:activity:7391501392387108864/

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