What do you owe someone in the thirty seconds after you've just ended their career?
When David Cancel did his first layoffs at Drift, the business math was easy. The hard part was looking at people he'd personally convinced to leave stable jobs and telling them it was over. That distinction frames everything founders get wrong. They prepare the spreadsheet, rehearse the legal script, and forget they're about to sit across from someone whose identity just got revoked.
Your job is part of who you are. Not metaphorically. When someone asks what you do at a party, they're asking who you are. When that identity gets taken away, the grief response mirrors losing a relationship. The person getting laid off experiences a death. The person delivering the news often doesn't understand that.
This creates the worst possible opening line: "This is really hard on me." Never say that. They don't care. You're keeping your job. They're not. Your discomfort is irrelevant to someone whose week just collapsed.
Founders delay layoffs because they believe they can turn things around. Three more weeks. One more deal. Here's the calculus: if you can only offer four weeks of severance, it's time to pull the trigger. Waiting longer means offering less. And cut deep enough the first time. Thin cuts that require a second round six months later devastate morale more than one decisive restructuring.
Stoicism kills you in the actual conversation. Coldness is cruelty. You can show that it's hard without making it about you. You can say "this is my fault" and get choked up. What you can't do is sob, because then you're stepping on their feelings. The grief belongs to them.
Know the person across from you. Some need time to process. Others want to solve the problem immediately. The employees who came back grateful said the same thing: transparency and honesty delivered before the final conversation so the news wasn't a complete surprise.
You have to be in the room. Not HR. Not a VP. The person who convinced them to take this job. Explain the facts, commit to helping them land, then follow through. One company facilitated a job fair for people being laid off. Another founder made calls before the conversation, lining up potential spots. That's the bar.
The remaining team conversation happens immediately after, not the next day. Acknowledge what happened. Leave space for them to respond. The right energy: this sucks, and the opportunity we have is figuring out how a smaller team turns things around. Collaborative, not directive.
This is the job you signed up for. Layoffs might be the second-worst day of your career, right after shutting down entirely. The founders who do this well treat it as leadership, not administration. They show up. They tell the truth. They help people land.
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