A Great Hire in a Broken Structure Produces a Great Resignation Letter.
He slid two resignation letters across the table. The second was four months newer than the first and used the same phrase: “I appreciate the opportunity, but the role didn’t end up being what we discussed.” Two COOs. Same sentence. Same season.
By the time he called me, he’d spent close to half a million dollars on those two hires in eighteen months. He had his diagnosis ready: “We keep hiring the wrong people.”
I told him I wanted to see three things before I agreed. The job description. Whatever document explained what the COO could decide without him. And the last six months of his calendar.
He couldn’t find the second document because it didn’t exist.
The Hire Was the Symptom
“We keep hiring the wrong people” locates the problem in the candidate. The candidates were fine — experienced operators, screened by reputable firms, taking the job in good faith. They left for the same reason both left: the seat they’d been hired into wasn’t a job. It was a contradiction.
A senior role lives inside a system of decision rights, reporting relationships, behavioral commitments from the CEO, and a shared definition of success. When the system is broken, the seat is unfillable. Even by a great candidate. Especially by a great candidate, because a great candidate notices faster.
In his case there were five things broken at once.
Decision rights were undefined. He’d told both COOs to “run the business,” then weighed in on every operational decision he cared about. The COO and CEO collided on roughly half of everything. Both COOs eventually stopped initiating.
Outcomes were never specified. When I asked what a great year would look like, the answer took six minutes and arrived in three different versions. None of them was a metric.
The role contained a behavioral contradiction. He’d said out loud he wanted someone to run the business. He’d also approved every major operational decision personally for eight years and didn’t notice he was still doing it. The COO was hired against the first statement and managed against the second.
The reporting line was ambiguous. The board told both COOs they could come directly. The CEO told both COOs everything went through him first. Both were sincere. Both were incompatible.
“Culture fit” was a stand-in for loyalty. Both COOs had been brought in to challenge his thinking, then judged a bad fit for doing it.
Any one of these would have made the role hard. All five together made it impossible.
What Actually Changed for the Third Hire
We spent four hours mapping the role before writing anything down. The job description was the last document we wrote, not the first.
First was a decision rights document. Six pages. The COO owned capacity planning, manufacturing throughput, vendor management, the field service P&L, and hiring inside operations. The CEO owned strategy, capital over $250K, customer relationships above a defined threshold, and board management. Joint decisions had a short defined list. Escalations had triggers, not feelings.
Second was a year-one outcome statement. One sentence: by month twelve, throughput is up 30% with no degradation in quality, the field service P&L moves from breakeven to 12% operating margin, and the CEO is spending less than 15% of his week on operational decisions.
Third was a CEO behavioral contract — the three things he would stop doing the day the COO arrived. Approving operational hires under VP. Sitting in on the weekly ops meeting unless invited. Responding to escalations from inside the ops org before they’d been worked through the COO. He didn’t want to sign it. I told him the COO he was about to hire would either watch him violate it or watch him keep it, and which one happened was the most important hiring variable in the building.
Fourth was a reporting clarity statement, sent to the board before the search opened. The COO reports to the CEO. Full stop. Two board members pushed back. The CEO held the line.
Then we wrote the description. About forty minutes. Roughly half the length of the previous one.
The third COO was hired in the same salary band as the previous two. Roughly the same experience. Same search process. The variable that changed wasn’t the person. That COO is still there three years later. The company has grown from $28M to $61M in those three years. The CEO is spending 60% of his time on strategy and the board — the work he’d wanted to be doing for the previous decade.
The Math of an Eighteen-Month Structural Absence
Two retained-search engagements: $100K–$160K. Comp consumed across two partial-year engagements at $280K base plus bonus: $300K–$450K. Severance for both: $150K–$250K. Visible costs run $550K–$850K.
The invisible cost is bigger. While both COOs were failing and during the empty months between them, the CEO was effectively running operations. The strategic work he was hired by his board to do didn’t get done. The deals didn’t get pursued, the operational improvements didn’t get installed, the strategic moves got deferred. In that eighteen months, the company grew roughly 4% against a category growth rate of 14%. The structural absence cost him probably $4M–$6M in revenue trajectory alone.
That is the actual price of running the same broken search twice.
Warning Signs
“We’ve had trouble with this role before.” The clearest signal and the most easily dismissed. Once is a candidate problem. Twice is structural until proven otherwise.
New hires underperform within six months, consistently. Six months is when reality settles in. Multiple hires hitting that wall in the same role means the role is hitting them.
The description is vague about authority. “Works closely with the CEO,” “partners with the leadership team,” “drives alignment” — none of those describe a decision. A clean description names what the role owns outright, what’s shared, and what escalates.
You’d struggle to define “great” in one sentence. Try it now. If you can’t, the candidate can’t either.
The Pattern
A great hire in a broken structure produces a great resignation letter. When you’ve had the same role fail twice, the variable you control isn’t the search firm, the comp band, or the screening process. It’s the operating environment.
The Three Documents That Have to Exist First
A decision rights document. Two columns plus a short third for what’s shared. If you and the role’s direct manager can’t agree on what’s in each column, the document isn’t done and the search isn’t ready.
A year-one outcome statement. One sentence. Twenty-five words or fewer. What does this role have produced, measurably, twelve months from start date?
A CEO behavioral contract — the three things you will stop doing the day this person arrives. This is the document most CEOs skip and the one that most often determines whether the hire succeeds.
When all three exist, the description writes itself.
Where This Lands
The CEO who keeps hiring “the wrong people” for the same role is almost always running a structural problem dressed up as a recruiting problem. That’s good news, even when it doesn’t feel like it. The structural fix is something you control.
If you’ve lost the same role twice, or you’re about to open a search for one you’ve struggled to fill before, that’s the right week to look at the structure first. The candidates will look better when the seat is real.
If you want a thought partner to work through what the role actually owns, what the CEO has to stop doing, and what twelve months of success looks like before the search opens, reach out at jane@janegentry.com.