Where this usually shows up.
Hiring trouble at the 5-to-50-person scale rarely looks like a recruiting problem. It looks like a quiet, recurring frustration — the role you keep rewriting, the manager you promoted who is now somehow doing less, the candidate you really like who you can’t quite say yes to. When owners come to us, it’s almost always one of these:
- The first ops hire — the one you’ve been putting off for a year.
- A manager you promoted who is now somehow doing less, not more.
- A role you’ve rewritten three times and still can’t fill.
- The person you can’t afford to lose and haven’t told that to.
If two of those are true, the issue is usually further upstream than the job ad. Companies pick the wrong candidate for manager-level roles eighty-two percent of the time, according to Gallup — and most of that miss happens before the first interview, in how the role was scoped.
Before the job ad: write the problem.
Most hiring trouble we see at the owner-operator scale starts in the same place. The owner sits down to write a job ad. They list responsibilities — oversee operations, manage vendors, lead team — and post it. Resumes arrive. Someone delightful is interviewed. The offer is extended on chemistry, and four months later, the owner is still doing the work the role was supposed to take off their plate.
That isn’t a hiring problem. That’s a description problem.
The first move in hiring well is writing down what the role is for, not what the role does. The decisions it removes from your plate. The two outcomes you’d measure in ninety days. The ways the role can fail. Job ads are downstream of all of that — and they almost write themselves once the problem is on paper.
How we work on it.
Most hiring engagements run four to six sessions over six to twelve weeks — front-loaded, because the work is in scoping the role, not in interviewing the candidates. Priya Mehta leads this pillar. She spent a decade as COO across three owner-operated firms — a specialty manufacturer, a design studio, and a regional logistics company — before coaching full time, and now works mostly with founders making their first ops hire and managers stepping into their first manager-of-managers role.
A typical engagement looks like this:
- First two sessions. Write the problem the role is solving. Draft the one-page scorecard. Name the anti-pattern — what this role is emphatically not.
- Middle stretch. Sketch a 30-60-90 measured against owner-time-reclaimed, not hire ramp. Build a candidate screen that interviews for outcomes rather than personality.
- Closing sessions. Run the offer with the scorecard attached. Set the day-30 and day-60 check-ins on the calendar before the start date.
The deliverable is a one-page scorecard, a 30-60-90, and a calendar that puts the hard conversations on the books before anyone needs them.
A 24-person creative agency in New York came to us after the founder had rewritten the COO job ad three times and stopped before posting each version. The agency was profitable, the founder was working sixty-hour weeks, and the role kept slipping out of focus.
We rewrote the role from the problem outward — three decisions it would remove from the founder's plate, two ninety-day outcomes, one anti-pattern. The hire cleared the day-60 mark cleanly, and the founder reclaimed Tuesdays for client strategy work for the first time in two years.
"I'd been trying to hire a person. Priya had me describe a role. The hire was almost easy after that." — Tomás A., founder
Is this for you?
Most of our hiring work has been with service businesses, agencies, and small manufacturers — places where the first ops hire or the first manager hire shapes the next two years of the company. If you’re hiring at the executive-search end of things — a public-company CFO, a tenured CRO — the work changes shape, and a search firm is usually the better fit. We’ll say so on the call.
The work scales between five and fifty people, but the urgency does not. At five, the first ops hire is often the most consequential decision a founder makes that year. At fifty, it’s the manager handoff that decides whether the company can keep growing or has to wait for the founder to free up. Tell us where you are.
We work mostly on the role definition and the 30-60-90 — not on candidate sourcing or running the interview process directly. If you need someone to run the search itself, that’s a recruiter’s job, and we’ll point you at one if that’s the right move.
On price: coaching isn’t free, and engagements vary by size and scope. We share specifics on the intro call, once we understand the shape of the work — usually within the first ten minutes.