The six-month trap for CEOs
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I had been in that elevator 100 times before.
The doors opened and 50 team members started cheering. A red carpet rolled out in front of me across the office floor. I walked along it with no idea what was happening until someone near the back said, "That’s not him."
The cheering stopped.
The most senior leader in the room came over and apologised, then explained what I had walked into. The carpet, the crowd, and the cheering were the first 30 seconds of a new employee welcome. The person it was built for was still downstairs. What followed for them was a tour of the office, a lavish lunch with her team, and the afternoon off. Quite a first day.
I have thought about that morning many times since, usually when a client tells me about a senior hire who might not be ‘the right fit’.
Most senior leaders arrive to a different kind of first day. They come out of a long recruitment process, sometimes an exhausting one, carrying a 90-day plan, a document that sounds more complete than it often is. It’s a structured collection of thoughts, cobbled together from desk research and intelligence gathered throughout the process and assembled to convince the recruiter and their client of their strategic thinking and commercial nous they’ll bring to the role. It was written to win the job, never to run the business.
Then they are let loose into the organisation to meet their teams, get a lay of the land, and start delivering value.
Invisible puzzle pieces
A CEO I coach appointed a sales and operations leader with nearly two decades behind her, and my client was excited for three reasons.
The first was capability. The appointment closed a sales leadership gap that had been open for a while, and the new leader was confident she could build a competitive, fit-for-purpose revenue engine.
The second was succession. My client could picture handing over the business she had built to this person when the time came, and that thought let her relax for the first time in a long while.
The third was rapport. She said, ‘We almost finish each other’s sentences.’
It was the third point that made my spider senses tingle.
Likeness is a strong asset in a working relationship. It also opens a door to ‘I thought what you meant was’, because two people who are that comfortable together tend to stop spelling things out.
My client had not closed the loop on three critical elements with her recruit. She didn’t feel she needed to because after all, they thought they understood each other.
The honeymoon period ended around the six-month mark and by then the new leader had backed a position without knowing whose support she needed to carry it forward and had waited on decisions she could have made herself. She spent the second 90 days rebuilding credibility she had lost in the first.
She had spent six months operating inside a business whose decision rights and sponsorship dynamics hadn’t been explained to her and interpreted the consequences as a verdict on her fit.
I disagreed with that assessment.
Because while the CEO is a capable leader, she had left three critical elements undefined and her new hire had paid for it.
Design problem or judgement error
A hire you privately doubt is more often a design problem than a judgement error, and the two send you looking in different directions.
A judgement error sends you back to the interview process. You look harder at the next resume, add another round of references and tighten the questions.
A design problem sends you back to week one, which is usually where an important solution lives.
The three critical elements missing from the new hire’s first week are the same three I look for whenever a CEO tells me a new senior appointment might not be ‘the right fit’.
The first is decision rights, and this is the one you can close in a single conversation this week. Take a minute to think of the last question your newest senior hire brought to you.
Most CEOs leave decision rights implicit on the assumption that seniority signals authority. That’s only sometimes true. Nearly two decades of experience told my client’s new leader how to run a revenue function. It could not tell her whether approving spend in this business was a $10,000 decision or a $100,000 one, or whether she could restructure her own team inside her first six months without taking it to the board.
That question you just thought of, the last one that your new senior hire asked, was a gap you could have closed.
Take Action: Write down the five decisions this person will likely make most often in their first six months. Against each one add a label: theirs alone, theirs with your input, or yours with their input.
The list takes about 20 minutes. Hand it over in week one rather than in week ten, after they have made the wrong decision twice in front of people who noticed.
The second is sponsorship.
Every function has two or three people whose support determines whether a new leader’s ideas move, regardless of what the organisational chart says. Sometimes it is a long-serving finance director who owns the numbers everyone trusts. Sometimes it’s a founder-era engineer that nobody reports to but everyone defers to.
You know who these people are without having to think about it, because you built the business alongside them. My client could have drawn that map on the back of a napkin over coffee. It didn’t occur to her that it was invisible from the outside.
Take Action: Naming three or four of them, and saying why each one matters, takes about 30 minutes and avoids the consequence of your new leader backing an idea without the right sponsorship.
The third is a definition of momentum.
Aim for measures rather than ‘settled in’ and ‘hit the ground running’ which give neither of you any evidence to point at in six months. Aim for objectives like ‘the new pricing model is live, and the sales team is using it across all new business’ or ‘the finance function has closed a month inside five working days without a late night’.
The goal is to have two or three of those, said out loud, in person, that are specific enough that at day 180 you and your new leader could stand in the same room and largely agree on whether it happened.
Take Action: Say them again a few weeks later, in front of one other person who matters to this hire’s success. A target that lives in two heads erodes over a busy quarter, because nobody else in the room is holding it up.
Back to your most recent recruit
Think about the most recent senior leader you hired.
If you asked them this afternoon what winning looks like in six months, would their answer match the one in your head?
Then the harder version. Have you ever said it to them out loud, in words you chose, with someone else in the room?
If nothing specific comes to mind, your new leader is already forming a verdict on themselves. They will decide whether they belong here long before you decide whether they are working out, and they will use whatever you gave them in week one to reach it.
Close the loop this week. You might find you were right about this person all along and had never told them what good looked like.
See you next Wednesday.
Phil Hayes-St Clair
CEO Coach
PS If this essay helped, Episode 242: Three insights every new executive needs to be successful in the first 90 days from my podcast is worth a listen. Tune in on Apple Podcasts, Spotify or wherever you get your podcasts.
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