You sold them on the culture. Then you sent the contract.
Most companies have values. They’re on the website, in the employee handbook, sometimes on the wall. Transparency. Integrity. People AI first. We mean it, and we want you to know we mean it.
And then we hand you a contract drafted by a lawyer whose job is to protect us from you.
Nobody notices the dissonance. Or rather, everyone notices it and nobody names it. The contract is the first real artifact of the relationship. Before the first meeting, before the first deliverable, before anyone has proven anything to anyone, there’s the contract. And if it’s written to protect one party, it doesn’t matter what the values poster says. Most of us sign it anyway, because we need the job, and the doubt is just the tax we pay to get in the door.
It’s not malicious. It’s just what happens when you outsource your first cultural touchpoint to someone whose brief is to protect the organization. The lawyer does their job, and the values take the hit.
I decided I wanted the contract to be where the values show up first, not where they get quietly contradicted.
What I ask my lawyers to do differently
I’m not a lawyer. My lawyers shake their heads at my draft contracts. The drafts are plain, sometimes imprecise, occasionally missing things a trained eye would catch immediately. That’s what the legal review is for.
But here’s the instruction I give: understand the intent behind what I’ve written and turn it into legal protection for both parties.
That’s a different brief from the standard one. Most lawyers are engaged to protect the organization, and they do that job well. I’m asking mine to legalize a document that was already written to be balanced, not to rebalance a document written to be one-sided. The goal isn’t to find legal language that gives us more than we need. It’s to find legal language that means exactly what we said we meant.
Plain English notes are how I make that intent legible to the other party, to my lawyers, and to myself.
The moment I stopped doing contracts the normal way
I was sitting across from a contractor — smart, experienced, someone I genuinely wanted to work with — watching her scan a twelve-page legal document for the first time. I could see her processing it, not really reading it but processing it, looking for the thing that was going to hurt her. Her body language was cautious in a way that had nothing to do with me, and everything to do with every document she’d signed before mine that turned out to mean something other than what she thought.
That’s the moment the problem became concrete. The values were real, and the relationship I wanted to build was real, but the document in her hands was doing the opposite of what I intended. It was making her cautious, not confident.
So, I started doing something different.
What a Plain English note actually is
Every legal clause in my agreements is followed by a second version, and I don’t mean a summary or a tooltip or a glossary at the back. I mean a note, right there under the formal text, that says what the clause actually means in practice.
Here’s a real example, from an independent contractor agreement I just finished:
The formal clause: “All work product, software, designs, documentation, analyses, and other materials created by the Contractor in performing services for Larkwin on or after the Start Date are and will remain the property of Larkwin Group Limited. The Contractor hereby assigns to Larkwin all right, title, and interest in and to all Work Product, including all intellectual property rights therein.”
The Plain English note: “Anything you make for Larkwin, from your first day, belongs to Larkwin. By signing this agreement, that assignment is done — no extra paperwork needed. Your own tools and prior work stay yours, and you’re free to keep using them anywhere else.”
It’s the same content, but it’s a completely different experience to read.
And notice what the Plain English note does that the clause doesn’t: it anticipates the worry. The lawyer’s version establishes what Larkwin owns. The Plain English version also says what Larkwin doesn’t own: your own tools, your background IP, your portfolio. Because that’s what the other person is actually wondering when they read that clause.
Why I think this matters more than people realize
There’s a legal reason and a human reason.
The legal reason: you can’t claim you didn’t understand something when the document itself explains it in plain language right below the formal text, so it actually protects both parties. I also include a line in every agreement that says if the Plain English note ever seems to conflict with the numbered text, the numbered text governs. That’s deliberate, because the note is a translation, not a substitute.
The human reason is harder to articulate but more important. When someone signs a contract they don’t fully understand, the relationship starts with an information asymmetry. The drafter knows what the document says, and the signer is just hoping. That gap doesn’t usually cause problems when everything goes well, but it does when something unexpected happens and the two parties discover they had different mental models of what they’d agreed to.
Plain English notes close that gap at the beginning, when it costs nothing, instead of at the end, when it costs everything.
What writing them has taught me about my own contracts
Everyone should try this.
When you force yourself to translate a legal clause into plain language, you find out whether you know what it means. I’ve caught drafting errors this way: moments where the formal clause said something slightly different from what I intended, and I only noticed because I tried to explain it and couldn’t. The Plain English note became a consistency check on the legal text.
I’ve also caught gaps. There’s a difference between a clause that’s technically correct and a clause that covers the situation. Writing the plain-language version forces you to think about the situation, not just the language. “What does this mean on a Tuesday afternoon when something goes sideways?” is a different question from “does this clause hold up legally?”
The answer to the second question is your lawyer’s job. The answer to the first one is yours.
What AI did with this
I use Claude to draft my contracts, and I’ll be transparent about how that goes.
What I’ve found: AI is genuinely good at the same things traditional legal drafting is good at. It’s technically sound, comprehensive, cautious. What AI needs pushing on is the human register. The Plain English notes are where I work hardest with Claude. I push for clarity over completeness, specificity over hedging, a second-person voice that talks to the person instead of about them.
But the notes are doing something else too. The contract itself becomes proof of the culture. When I send a draft and say — I’m not a lawyer, our lawyer will review this, but I’ve made a start, take a look, ask questions, push back, let’s go back and forth until we’re both comfortable — I’m not just drafting a contract, I’m demonstrating how we work before they’ve had a single meeting. They learn something true about Larkwin before day one.
Here’s the slightly absurd part: I’m using AI to make contracts sound less like they were written by a machine.
It works, though. When I share a draft, the Plain English notes are almost always where the other party responds with “can you clarify...”. And those back-and-forth emails start off very coy, tentative, apologetic even, and end with me knowing them a little better and them believing in me and our company. By the time they sign, they already know who they’re working with.
A note on what this isn’t
Plain English notes don’t make a contract friendlier in the sense of making the terms less strict. My IP assignment clause is full IP assignment, my confidentiality clause is perpetual for trade secrets, and my termination provisions have teeth.
And I want to be clear about something. I would love contracts that just say we will be fair to you and you will be fair to us, and I really do mean that, but I’ve been on both sides of “fair” when things went sideways, as the employer and as the employee, and I can tell you that fair is an extraordinarily subjective word when there’s money, or a relationship, or a reputation on the line.
The teeth are there because I’ve seen what happens without them. The Plain English notes are there because I believe the person across the table deserves to understand exactly what those teeth are.
One of our values at Larkwin is Clear is kind. The idea is simple: withholding clarity isn’t diplomacy, it’s just a delayed problem. A contract written in language designed to be signed rather than read isn’t protecting the relationship. It’s just postponing the moment when someone realizes what they actually agreed to.
And a contract that walks your values from the first page? That’s not just good drafting. That’s culture.