Before You Call the Lawyer
Founders call me before they call the firm — and more often than not, what looks like a legal problem is a conversation they've been avoiding.
Field note · 8 December 2025 · 4 min read
She called me four times over four months. Each time she described it as an HR issue.
First call: performance documentation. Second: what she could and couldn't say in a recorded meeting. Third: formal process timelines. By the fourth call, we'd spent close to eight hours on legal scaffolding for something that, when you pushed on it, came down to one conversation she hadn't had with her co-founder.
She had that conversation. The HR issues dissolved.
That's what I hear most often, from where I sit. Not a legal problem. A conversation being avoided, routed through the only professional who feels safe to call. The legal question — am I exposed? can I do this? — is almost always the secondary question. The primary one is: what's the conversation I've been building paperwork around?
Here's what the three most common versions look like from this side of the phone.
The document exists because the conversation hasn't
A founder wants to manage someone out without getting sued. They've built a document — six pages, sometimes ten. Performance concerns, specific dates, impact on the team. Weeks of work.
Push on it for five minutes and the same thing surfaces: the person doesn't know they're in trouble. Not really. The feedback they've received has been indirect — the word "growth" has appeared a lot, when what should have been said, directly and specifically, is that the role isn't working.
In seven years across Google and Meta's people operations, I watched hundreds of formal processes unfold. The majority that went badly — that ended in disputes, legal claims, or just expensive drawn-out misery — shared one feature: the first time the person understood the true shape of the problem was when they received a formal document. Not a conversation. A piece of paper.
That's not a legal exposure problem. It's a management failure, and it's preventable.
The first step before any formal process is one direct conversation. Not an HR meeting. A conversation between two people, where you say the thing plainly:
"I want to be direct with you about something I should have been clearer on earlier. The role isn't landing the way either of us needed it to. Here's what's not working: [specific behaviours, not adjectives]. Here's what has to be different in the next sixty days. I want to give you a real shot at that, and I want you to have the full picture so you can make an informed decision."
That conversation takes a fraction of the time. The alternative — process, documentation, a potential dispute — takes months and typically costs five figures. The conversation is not the risk.
Avoiding it is.
What you actually want is permission to have the conversation
Co-founder disputes are the hardest version of this. Something has shifted — equity feels wrong, one person is pulling less, the original vision has split. They want to know their legal position.
What they actually want, almost without exception, is permission to address the thing that's been sitting between them.
The legal frame makes it feel safer — more procedural, less personal. But it doesn't solve anything, and once you're in formal dispute — positions staked, the adversarial frame in place — everyone defends what they've claimed. That's not a criticism of lawyers. Mediation and negotiated settlement preserve more than most founders expect. What adversarial litigation rarely does is restore the relationship itself.
The conversation that needs to happen before anyone books counsel:
"I need to talk about something that's been building for me. Not because I want to blow this up — because I don't want to lose what we've built. Here's what I'm experiencing: [specific, not accusatory]. I want to know what you're experiencing. And then I want to figure out if there's a version of this that still works."
That conversation either surfaces something workable or confirms you've reached an impasse. Either way, you've earned that information before you've paid for it.
If you're going to lawyers without having that conversation, you're not protecting yourself. You're paying to defer the thing you should have done first.
Three questions before you make the call
The version I get most often: "We've decided to let someone go. When do we involve the lawyers?"
Sometimes immediately — there's real legal complexity, the situation has unusual features, you need counsel early. But a lot of the time, what founders actually want is reassurance. The decision is made. They're second-guessing the execution. They want confirmation they can proceed.
That's not a legal question. Before you pick up the phone, three things worth sitting with:
- Has this person received clear, direct feedback — not softened, not indirect — about what wasn't working? Not a document. A real conversation.
- Is there anything they could reasonably claim they didn't see coming? If you have to think hard about this, the answer is probably yes.
- Have you thought through the human conversation — not the legal one? What you're going to say. How it's going to land. What you owe them as a straight account of what happened.
When the answers are yes, it goes better. Not always well — there's no version of this that's easy — but better. The legal layer protects you after the conversation. It can't replace it.
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The paper trail is real, and often necessary. But the thing it's usually substituting for is older and simpler: saying the hard thing directly to the person it concerns.
A lawyer can protect you once you've had the conversation. They cannot have it for you.
So: what's the conversation you've been building a document around?
