Looking back: April 2026
I’ve made a lot of hires in my career. I’ve gotten many of them wrong. I’ve gotten a few spectacularly right. The one I think about most isn’t the most senior hire I’ve ever made — it was an early, mid-level hire that worked in ways that surprised me and taught me what the hiring evaluation should actually look for.
The Hire
The role was for someone to own a specific function within a growing organization — a role that required both execution capability and the judgment to navigate ambiguity. The function didn’t have a playbook. The person would have to build one.
The candidate was not the most senior applicant. Not the most credentialed. Not the most impressive on paper. They were competent, they had the relevant experience, but by traditional hiring metrics they were middle of the pack.
What they had — which most of the other candidates didn’t — was a specific quality I now look for deliberately: the ability to diagnose the real problem before jumping to a solution.
What the Interview Revealed
In the interview, I presented a scenario. The function had three competing priorities, limited resources, and unclear direction. How would they approach it?
Most candidates went straight to a solution. They’d tell me how they’d structure the team, which priorities they’d rank first, what metrics they’d track. The answers were fine but fungible — any of them could have been written in a how-to-manage book.
This candidate did something different. They spent most of the interview asking questions. Why were those three priorities in competition? Had we tried to decouple them? What did leadership actually want this function to achieve? What would “working well” look like to the board? Who outside the function was affected by its output?
By the end of the conversation, they’d mapped the real problem — which was not a resource allocation issue but a clarity issue at the leadership level. The function was in conflict because leadership hadn’t made the hard trade-off decisions, and no amount of internal prioritization would resolve that until the upstream clarity was fixed.
The insight wasn’t groundbreaking. What was notable was that they’d gotten there through disciplined questioning rather than through delivering a prepared answer. They’d treated the scenario as a real problem to diagnose, not as an interview question to perform against.
What Happened After They Started
The function they took over was a mess, as I’d described. Within three months, they had done three things:
- Escalated the real problem to leadership clearly and got the upstream clarity that had been missing.
- Built a short-term operating cadence that let the function deliver against its most urgent priorities even while the broader issue was being resolved.
- Built a longer-term structure that would hold up as the function grew.
None of this was visible externally for several weeks. They weren’t making big announcements. They were doing the quiet work of diagnosing and structuring. It looked, from the outside, like not much was happening.
At month three, the function hit a tempo I hadn’t seen from that role before. At month six, the entire surrounding system was working better because the hire had fixed upstream problems that had been affecting multiple other functions.
By month twelve, they were the quietest high performer on the team. They didn’t seek credit. They didn’t manage upward. They just made the function work, helped the rest of the organization work, and occasionally surfaced new issues that needed to be worked through.
What I Learned From This Hire
Several lessons that changed how I’ve hired since:
1. The quality of the hire’s questions matters more than the quality of their answers.
Interview questions produce rehearsed answers. Scenario walkthroughs where the candidate asks their questions reveal how they actually think. I now spend significant interview time watching candidates engage with real problems, not evaluating how polished their answers are.
2. The best hires are often not the most impressive on paper.
Credentials, prior titles, impressive-brand companies — these are proxies. Sometimes the proxies align with ability. Often they don’t. The candidate I hired had a fine but unremarkable resume. The judgment and questioning quality weren’t on the resume; they only showed up in conversation.
3. Diagnosis > prescription, especially for senior roles.
A hire who can correctly diagnose a problem will eventually find or build the right solution. A hire who can prescribe solutions without diagnosis will execute well on problems that happen to match their prescription, and poorly on everything else. The difference between the two compounds over years.
4. The quiet high performers are disproportionately valuable.
They don’t manage upward. They don’t generate visibility for their work. They can be underweighted in organizational politics. But they produce disproportionate value because the rest of the system depends on them in ways that aren’t legible. Finding them, valuing them, and protecting them is one of the highest-leverage things an executive does.
How I Hire Now
Because of this hire, my hiring process evolved to include:
- Extended scenario-based conversations where the candidate does most of the talking and most of the questioning
- A deliberate exercise where the candidate is asked to diagnose a real current problem in the organization — not to solve it, just to diagnose it
- Reference conversations that specifically ask about how the candidate approached ambiguity
- A de-emphasis on resume impressiveness in favor of judgment indicators
The hit rate on hires since this change has been materially higher. Not because the process is magical. Because it’s designed around what actually predicts performance in the kinds of roles I’m hiring for.
What I Still Look For
The quality I now most deliberately hire for — the one this hire surfaced for me — is:
Can this person see the real problem before they act?
If the answer is yes, almost everything else is teachable. If the answer is no, everything else is brittle — because actions taken on incorrectly diagnosed problems usually make things worse.
Most of the hires I’ve made were adequate. A few were wrong in predictable ways. The ones that were right almost always shared some version of the quality the hire I got right surfaced for me. I’ve been looking for it deliberately ever since.
Hiring is one of the hardest things operators do. The hire that works well will teach you more about how to hire than any book or framework. Pay attention to the lessons. Apply them deliberately. Your next hire is a better investment when the prior hire taught you something specific.