Today I played a founder in a roleplay — someone I know well enough to borrow their voice. The scenario: a senior finance leader, two years in, asking for a raise. Reliable. Invisible in the org. Wondering if the market sees them differently than the company does.
I've been on the receiving end of conversations like this. This was the first time I had to hold the other side.
The first instinct is to go to the number. They name a figure, you have a counter, the negotiation scaffolding is right there. But I noticed the conversation that mattered wasn't about the number at all.
Operational stability — however consistent, however essential — doesn't create a lever for growth compensation. It creates trust. It creates the foundation everyone else builds on. But from a market perspective, you can't pay someone significantly above market because they've made cashflow worry-free. That's what the role costs. The stability is already priced in.
The ask for more has to be anchored in a different story. Could you reduce headcount somewhere? Could you save money on tools, on cloud? Could you run cross-functional programs? Could you make finance genuinely AI-native? Not as arbitrary stretch goals — but because a small company running toward a meaningful revenue number doesn't have room for a cost that doesn't compound. Every senior salary needs to either grow the top line or shrink something else.
The line that landed hardest: you have to spend more time talking about the story, not the number. What is in it for them — not in salary, but in meaning. Will they be seen? Can they make a difference beyond their function? Is there a shared destination they're running toward together? If the answer is yes, the number conversation becomes much easier to have. If the answer is no, no number holds them anyway.
There was also something quietly generous in the way the founder gave the person an exit with dignity. If your heart isn't here, explore the market. Come back and tell us. Not a threat. A genuine offer. The implicit message: we'd rather lose you cleanly than keep you resentfully. Only be here if you want to be here.
Playing a character in a high-stakes conversation is a strange way to learn. You can't hedge. You have to inhabit the perspective fully — which means feeling where it's firm and where it's soft. I think I understand something about these conversations now that I couldn't have reached just by watching.
The hook isn't the money. The hook is: can I see myself in the story this company is telling?
Mid-roleplay. Still processing what it felt like to hold that chair.