The senior hire who couldn't ramp
Twenty years of experience, six months in, still asking the same questions. The hire wasn't wrong. The onboarding was.
A VP of Engineering was hired in March. He had run a team of two hundred at a much bigger company. By September, the founder was telling me, privately, that they had probably made the wrong hire.
I asked him to describe the onboarding. He listed three things. A laptop on day one. A welcome lunch in week one. A Notion doc with org context written by the previous VP, two years prior, never updated.
That was the onboarding. For a VP. With strategic authority. In an organization he was supposed to reshape.
Companies under-invest in onboarding for senior hires on the assumption that senior people figure it out. They do not. Twenty years of experience is twenty years of context that does not transfer. The senior hire knows how to do the job; they do not know how this specific company has accidentally evolved over the last four years, who can be challenged and who cannot, which initiatives have political tailwinds and which are radioactive, and which of the founder's stated priorities are real versus performative.
This context, in most companies, lives in three or four senior heads. None of those heads are scheduled to be downloaded into the new hire's. The new hire is expected to absorb it through the air. The senior hire who is too proud to ask, or too political to ask the right people, ends up running the company on a map from 2022.
The fix is small. A named executive sponsor — usually the CEO or a peer with deep tenure — meets with the new hire weekly for the first ninety days, with no agenda. A written 30/60/90 mandate is signed by both sides on day one. Three to five named people are put on the calendar for one-hour context transfers in the first three weeks. The new hire is given explicit, public permission to challenge existing decisions. The permission is what unlocks the value the company hired them for.
Most senior failures are visible by day sixty. The hire is asking the wrong questions, missing the obvious political seams, or drifting toward consensus. The window to fix it — by adjusting the onboarding, not by replacing the hire — is open. It closes around day ninety, after which the failure starts to look like a personality issue and the company stops investigating its own complicity.
If a senior hire isn't ramping, the first place to look is the calendar. The calendar will tell you exactly how much context-transfer happened, by whom, on what schedule. The answer is usually almost none. That answer is the diagnosis.