You can like the person, believe in their values, and still never tell them what the job actually demands.
I’ve walked out of interviews pretty sure we had found the right person.
Smart and easy to talk to. Someone I could picture sitting across from a client, representing Sanctuary well.
The rest of the team liked them too. That mattered to me. Culture has always been the first thing we test for.
A number of years ago, while we were growing quickly, we hired people into strategist roles who passed every one of those tests. They were quick on their feet through multiple interviews. They had experience and knew the industry. I liked them personally.
They did not succeed in the seat.
The easy lesson would be that we should have hired for values. We did. Values were what we tested hardest, and they held up. What we never did was define what the seat demanded, then ask anyone to show us they could do it.
I’m going to stay with that one role for this piece. The strategist seat is critical to how we serve clients, and it’s the one that taught me this lesson.
The seat is a mindset, not a task list.
On paper, a strategist’s job is easy to describe. Understand the client’s business, recommend a plan, and explain it in a way an owner can act on.
The real job sits underneath that.
A client has a goal, a budget, and several possible ways forward. The information is incomplete. People at the table hold strong opinions, some of them in conflict, and more than one of them may have merit. There is no definitive answer. The strategist still has to recommend a path, then decide what to measure and where to check progress, so we find out we’re wrong before we’re too far in.
It also means seeing alternate futures. This path leads one place, that one leads somewhere else, and a third goes somewhere else again. Where do they converge? Where do they split? It’s a little like playing 3D or 4D chess, and living in those worlds can drive you a bit insane.
Now put five stakeholders at the table. Three agree. Two don’t. The strategist has to stay calm, keep what’s right in the pushback, and still bring the room to a clear direction without folding every time someone disagrees.
Conviction matters. So does the ability to reconsider.
None of that shows up on a job description. All of it decides whether the person succeeds.
What an undefined seat looks like…
The people we hired had the fundamentals. What they didn’t have was a way of working that we had written down, because we didn’t have one.
Nobody had told them what questions to ask themselves when a client’s problem had no obvious answer. How to explore the options. When to escalate. How to test an idea with someone more experienced before it went in front of a client. The people who had done the job for years did those things by instinct. We had never said them out loud.
So a new strategist walked into client situations full of unarticulated ambiguity, carrying the title and none of the playbook.
You could see it in the work. Recommendations took longer than they should have. And the strategist could feel it. They didn’t feel strong in the role, and they had nothing to fall back on.
We weren’t careless about it. We had backup. Experienced people reviewed and refined the strategy, and nobody was turned completely loose on an account. But that meant we were managing the result to the finish line instead of preparing someone to get there. It introduced delays and uncertainty that clients could feel.
A few times it went further. We had real conflicts with clients where the quality wasn’t what it should have been. We resolved them. I also know what it could have cost us if we hadn’t been able to.
One undefined seat created two kinds of risk. An employee who didn’t feel capable in their own job, and clients who weren’t getting the full version of what they hired us for.
That part is on us.
I don’t feel right about how that played out, as a person, let alone as an owner. We liked these people. We wanted them to succeed, and we wanted them to stay. When someone you hired is struggling because nobody told them what the job really required, that is a failure on our part as much as anything.
They didn’t know our expectations for a strategist because we couldn’t articulate them yet.
Jim Collins talks about getting the right people in the right seats. I understood that idea for years. This experience is what made the seat half of it specific.
The interview never asked the hard question.
We asked a lot about culture. We had multiple conversations. But I knew early that I wanted to hire them, and every interview reinforced the picture I already had.
We never put an ambiguous problem in front of them and asked them to walk us through a decision. There was no exercise where a definitive answer was unavailable and a recommendation was still required.
The thing most likely to make or break them went untested.
A good conversation feels like evidence. And it is evidence, for part of the job. The mistake is letting it answer questions you never actually asked.
What changed, and what hasn’t yet.
Our process is more structured now. Initial vetting happens against the job description before candidates reach the hiring manager. A pre-established scoring template rates everyone on the same categories: knowledge, industry understanding, experience, and criteria specific to the position. That gets us apples-to-apples instead of a vibe about who felt qualified.
Candidates also spend time with the team without the manager in the room. The team picks up things I miss, and candidates ask the questions they won’t ask me.
But I have to be careful about calling the problem solved.
The people we hired had experience, understood the industry, and interviewed well. A scorecard that gives those things most of the weight could grade them highly and lead us to the same decision.
Today I walk into a strategist interview with sharper questions.
Can this person deal with ambiguity? Can they hold two paths at once without getting married to either? Can they make a recommendation and tell me what would make them change it?
Too much of that still lives in my head.
The next step is a practical exercise.
It should carry the mechanics of the work without being real client work: incomplete information, competing priorities, a decision to make. Then we introduce feedback and see how they respond.
They can fail at that and still get hired.
I mean it. A weak first recommendation followed by good questions and a thoughtful revision tells me more than a polished answer would. We’ve named the need. We haven’t built the exercise yet, and until we do, we aren’t consistently testing the thing that actually broke.
People who didn’t work out in that seat have gone on to real success elsewhere, and I’m glad they did. A role that was wrong for them here doesn’t define what they can do somewhere else. They were making a bet on us too, and they deserved a clearer picture of what they were signing up for.
Define the seat before you hire for it.
For me, that means being able to name the hardest judgment the person will need to make, and having a way to watch them make it before either of us commits.