A founder I spoke with last year, Nicholas, runs a 30-person services firm. Three rounds of growth in eighteen months, the kind of stretch where the founder stops sleeping properly and the leadership team starts to thin. Nicholas made what looked like the obvious move. He hired a Head of Operations. Twenty years’ experience, references that checked out, calm under pressure, the kind of CV that makes a recruiter relax for the first time in months.
Six months in, Nicholas was telling people privately the hire was not working out. The hire was telling people privately that Nicholas seemed impossible to please. Both were working hard. Both were operating in good faith. When I sat with each of them separately, the disconnect was clean. Nicholas wanted someone to wake up worrying about cash, hiring, and which clients to fire, the same way he did. The hire had taken on a senior operations role at a high-growth services firm and was performing it competently. Different jobs, same title. That is the pattern this post is about.
What goes wrong when you hire a senior person at the ten-to-fifty stage
The pattern is structural, not a talent failure. The founder hires a senior person into a role that on paper looks like a normal Head of Function. Six months later both sides are quietly disappointed, and neither has named the actual gap. The hire is delivering on the role they accepted; the founder is measuring them against a different role nobody put in writing.
Dover’s research on scaling from ten to fifty employees flags this band as the inflection where many promising firms hit the wall. The first hires were probably people the founder knew, generalists wearing several hats. By thirty staff the firm needs specialists who can run a function. But the firm has not yet built the systems, decision rights, or stable strategy a true Head role assumes. The role looks delegable on paper. It is not delegable in the way the founder needs it to be, and the founder rarely realises that until the hire is six months in.
The four expectations founders carry but never say
There are four unspoken expectations that sit underneath the role and almost never reach the job description. Each is real. Each is reasonable on its own terms. Together they describe a different job from the one the candidate signed for. The Coffeespace research on early-hire misalignment names them clearly, and they hold up against what I keep seeing in firms in this band.
The first is personal ownership of firm-level outcomes, not just functional outputs. The founder expects the hire to feel responsible for cash, growth, and the survival of the business, not only for their team’s metrics. The second is adaptability over playbook. The hire is meant to drop the way they did things at a larger firm when speed matters more than process. The third is emotional resilience inside chaos. The hire is meant to absorb the founder’s stress, not escalate it back. The fourth is active belief in the strategy when the data is ambiguous, the willingness to back the firm’s direction when caution would feel safer.
Why neither side names the gap
Founders rarely say these expectations out loud because they sound unreasonable when written down, and because they emerged from the founder’s own lived experience and feel like what good simply looks like rather than a personal preference. Saying them out loud would deter half the candidate pool, which feels like a problem in a tight hiring market and is actually the point.
Candidates rarely ask either, partly because they have not experienced founder-mode work and do not know what they do not know, partly because the offer is attractive and the founder is impressive, and partly because the language used in interviews (“ownership”, “scrappy”, “we move fast”) sounds reasonable from the outside without meaning what the founder means by it. Russell Reynolds’ research on senior-hire transitions describes this as believing you are doing a bigger job when you have actually accepted a different job. The data on senior-hire failure is consistent across the major firms, with thirty to fifty per cent of executive hires derailing within eighteen to twenty-four months. A meaningful share of those failures sit on this exact mismatch.
The conversation that fixes it, before the offer
The fix is mechanical, and it costs nothing. Said cleanly before the offer, the honest version of the role takes ninety seconds to deliver and saves a six-figure hiring mistake. The point is to give the candidate enough to self-select honestly into the version of the job you want filled. The exact wording matters less than whether the bit nobody wanted to say lands in the room.
The honest version sounds like this. “In this role, I expect you to behave more like a co-founder of your function than like a senior leader at a larger firm. That means feeling personal responsibility for the firm’s growth. Backing the strategy when the data is ambiguous. Absorbing emotional weight rather than escalating it. Some people thrive in that role and some find it exhausting. I would rather we both find out before you sign.”
The version that lands in writing is cheaper still. The job description includes the line “this role builds the function from scratch, the systems and decision frameworks do not yet exist, you will set them up while delivering the work”. The offer letter references a structured first-ninety-days plan with explicit ownership of decisions, what the hire decides alone, what comes to the founder, what good looks like at thirty, sixty, and ninety days. The Andreessen Horowitz playbook on executive hiring is firm on the point that the CEO leads the conversation, not the recruiter, because no one else can communicate the role that actually needs filling. By the end of the first thirty days the unspoken expectations are spoken expectations, in writing, jointly. New senior hires should not be left to read the room.
The honesty test that comes before the brief
There is a quieter question underneath all this, and it is for the founder, not the candidate. Do you actually want a mini-founder, or do you want a competent professional running a function while you keep holding the strategic weight? Both are legitimate answers. The mistake is briefing for one role and privately expecting the other.
Most of the time the brief reads like senior employee and the inner expectation is mini-founder, and the hiring outcomes reflect that gap. The work is to decide which you want before you brief the recruiter, then write the role honestly so the candidate pool can self-select. If you want a mini-founder, say so out loud, and accept that the pool gets smaller and the candidates who remain are the ones you actually wanted in the first place. If you want a competent function lead, brief for that, hold the strategic weight yourself, and stop measuring the hire against a different role they never accepted.
If you would like a second pair of eyes on a senior hire that is not landing the way you expected, or on a brief you are about to send to a recruiter, book a conversation.
