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Most people start a senior search by protecting a number. The comp they're on, the level they've reached — those become the floor, and the search turns into a hunt for roles that clear it. Reasonable. Also backwards. When the level is the target, you aim at the label. You filter for the title, screen for the band, and end up interviewing for roles you can technically do at a company you'll technically tolerate. You clear the bar. And six months in, you're running the same sea

"I think I could go the Director route at another big company. But there's a VP role at a startup that's got my attention. And honestly, part of me just wants something smaller where I'm building again." Same person. One breath. Three directions. I hear a version of this almost every week right now, and it never sounds like confusion. It sounds like someone with too many good answers. Every option is real. Every one is genuinely them. So they keep all three alive — a little n

Someone I talked to last week keeps reaching the final round and losing. Every loop, the same feedback: they loved him, they went with someone else. He's clearly capable — that's not the problem. The problem is he's spent a whole career being capable at everything. For years he was the person you handed the messy, cross-functional, no-clear-owner thing to. He'd take it and land it. A mentor once told him a jack of all trades beats a master of one, and he built his career on e

"I keep getting to hiring managers and stalling out." I hear some version of that every week. And on its own, it tells me almost nothing. Here's why. Say your direction's settled — you know the role, you know the industry. That same role still shows up in the market wearing wildly different shapes. A 25-person seed startup and Stripe might both be hiring the exact title you're going for, in the exact space you've picked. They are not the same conversation. Stage, size, who yo

You've known since winter. You updated the resume, had a few conversations, told yourself you'd really get going once the launch shipped, the reorg settled, or some other milestone outside your control arrived. It's June. You haven't really started. I don't think that's procrastination, and I don't think it's fear of rejection. Most senior people I talk to are avoiding something more specific: the length. A senior search runs six to nine months on a good day — no deadline, no

A lot of the people on my calendar right now aren't looking yet. They're "getting ready." The real search starts in September — once summer's done, the holidays are out of the way, and they've had time to sort themselves out. I get the instinct. September feels like the proper starting line. New quarter, everyone back at their desks, roles opening up. But here's what usually happens between now and then. "Getting ready" turns into tinkering. A new resume bullet in July. A few