Everyone was being careful. Nobody was being clear.
Ray spent five months building a strategy around one man.
Frank had been at the firm since before Ray got there. Everybody in the place had worked with him for decades. Ray described him to me once as a second father — older than his own dad.
The firm was in merger conversations. And the entire plan was shaped around one assumption nobody had tested: Frank would never leave.
What Working Around Someone Actually Costs
It isn’t one decision. It’s every decision.
Which structure they proposed. Which timeline they could live with. Which offices moved and which stayed. Who they could talk to and who they had to keep in the dark, and for how long. What they could say in a partner meeting and what had to wait for a hallway.
Every one of those got shaped by the assumption. And Ray was clear-eyed about it. He told me flat out it wasn’t a rational business mindset. He knew. He just said it would feel terrible to do that to Frank.
He’d spent his whole career with this man and didn’t want to be the one who pushed him out the door. Most people reading this would feel the same.
But notice what it produced. Five months of complicated, expensive strategy, built to protect someone from a conversation.
Why Nobody Asks
It isn’t cowardice.
The question feels like the decision.
Ray believed that asking Frank whether he’d ever leave was itself the act of pushing him out. That the question would land as a verdict. You’d be telling a man who’d given his life to the place that people were discussing whether he fit.
So the question doesn’t get asked. And because it doesn’t get asked, the assumption hardens into fact. Nobody ever wrote it down or agreed to it. It just became the shape of the thing.
Ray had also thought through what it would look like from outside — the market, the clients, the other lawyers in town. If the firm split in different directions, he said, it looks like a divorce and you’re fighting over the children.
So now the assumption isn’t just protecting Frank. It’s protecting everyone’s reputation. It’s load-bearing.
Then He Asked
Not a soft version. Not a hypothetical floated at the end of a call about something else.
He said: Frank, is there any number, is there any set of facts, where you would go — if that’s what we decided we wanted to do?
And Frank said he liked working with these guys. He wanted to keep the team together. If they wanted to go, he’d go.
Ray’s reaction, in his own words: oh shit.
The Part That Should Bother You
Ray told me something else about that week.
After the conversation, he hadn’t heard his other partner sound that relieved in five months.
Do the arithmetic. Two partners had been carrying this the entire time. Neither one had said out loud how much it was weighing on them. Each was managing it privately, on behalf of a man who had never been asked what he wanted.
Three people, all being thoughtful. All being careful with each other. And the result was five months of strain that a ten-minute conversation dissolved.
Everyone was being careful. Nobody was being clear.
The Version of This In Your Firm
You almost certainly have one. Most firms do.
Someone you’ve decided wouldn’t be interested. A partner you’ve concluded would never agree. A conversation you’ve been routing around for so long that the routing is now just how things work, and nobody remembers it started as a guess.
It’s usually not the person you’d expect. It’s the one you like. Protecting someone you’re indifferent to is easy — you’d just ask. The elaborate workarounds get built for the people you care about most.
And the tell is when you catch yourself designing around a position they’ve never actually stated.
Two things worth knowing about how these usually go.
The first is that the answer is frequently not what you assumed. Not always. But frequently enough that the assumption is a bad thing to build five months on.
The second is that even when the answer is what you expected, you get something you didn’t have before: it’s now a fact instead of a guess, and everyone can stop managing around it privately.
How to Ask
Ray’s phrasing is worth stealing.
Is there any set of facts where you would go, if that’s what we decided we wanted to do?
Three things are doing work in that sentence. It’s conditional — if that’s what we decided — so it isn’t an announcement. It asks about his conditions rather than his willingness, which gives him somewhere to stand other than yes or no. And it’s specific enough that a vague answer would be obviously vague.
What it doesn’t do is soften. He didn’t wrap it in reassurance or bury it at the end of a call about something else. Softening is what makes these conversations go badly, because the other person can tell you’re managing them.
One Question
What’s the conversation you’ve been building around instead of having?
You know the name. People always do.