The "Problem"
You're making your first hiring decision as a manager. Two candidates, both qualified, both likeable. One has more experience but lacks the technical skills (maybe AI) the role needs. The other is less experienced but technically sharp. Your brain says they're equal. Your gut says you're missing something. What do you do?
The Real Problem
Here's what no one tells first-time managers: you're not hiring someone to do work. You're hiring someone to train you how to manage.
Everyone talks about "hiring for culture fit" or "finding the right person for the team." That's consultant speak and means nothing. Your first hire isn't about your team. It's about you. It's about exposing your blind spots, showing you what good hiring looks like, and teaching you how to make the next four hires without screwing them up.
The tech expert versus the seasoned pro? That's a distraction. The real question is: who will make you a better manager faster?
Why This Happens
Many first time managers get stuck on exactly this problem, not because they're bad managers but because they only see the process from the outside before actually going through it themselves.
When you look at the hiring process as an external observer, even if you participate in it in some way, you're not seeing what goes on inside the hiring manager's mind. Truthfully, maybe that person is doing it wrong anyway and you SHOULDN'T be seeing what goes on. Either way, you don't have the full context to understand why that decision is being made.
What happens instead is that you default to what you've seen, and what you THINK should be the process because you've observed it time and time again:
- Review resumes
- Interview the best resumes
- Hire the person with the best resume and best interview
So you optimize for skills. For experience. For someone who can "hit the ground running." And you completely miss the point: your first hire will teach you more about management than they'll contribute to your team in year one.
What To Do Instead
Stop asking "who's the best candidate?", and start asking "who will expose my management gaps the fastest?"
Here's your new screening process:
Red flags before anything
Trust your gut. Does something feel off? Are they inflating their experience? Do their answers get more vague the more you probe? The best predictor of future behaviour is exactly what you're seeing in real time when they're trying to impress you.
Ask the wrong questions on purpose
Give them an ambiguous scenario with no right answer. Something like "our stakeholders want to use AI for a problem. Early results are promising but inconsistent. What would you do?". Then, watch what happens.
- Do they lie their way through by making up confident nonsense?
- Do they ask clarifying questions?
- Do they admit their knowledge gaps honestly or lie and pretend they know everything?
A person who asks better questions will teach you more about asking better questions. That's the skill you need to develop.
The six month struggle test
Imagine it's six months in and they're struggling.
- Which person would the team actually want to help?
- Which person's struggle will teach you something about your onboarding process, your delegation ability, your communication skills?
- Which person will force you to get better at difficult conversations, performance management, and coaching?
If the technical person struggles, you'll learn how to manage technically sharp people who lack organizational awareness. If the senior professional struggles, you'll learn how to manage people who are more set in their ways and unfamiliar with new tools.
Both teach you something - it's up to you to pick the lesson you need to learn.
The political reality check
Here's the uncomfortable truth: there are also political considerations to your decision. Think about it this way:
The less experienced person struggles -> you're criticized for not hiring a more senior person
The more experienced person struggles -> people are empathetic because you went with the safer bet
Ignoring the reality of how others in your organization will perceive things is naive. Learning to manage others' perceptions of you is just as important as actually delivering good work. Factor that in to your decision making and daily operation.
What Most People Get Wrong
- They optimize for people who can hit the ground running -> they miss who can teach them the most about management
- They hire for skills on the job description -> they miss hiring for judgement that can't be articulated in bullet points
- They pretend politics don't matter -> they get blindsided and harm their careers when their hire struggles and suddenly everyone has opinions
- They think it's about the team -> they miss that this is training themselves for hires 2+
The Bottom Line
Your first hire will teach you more about management than they're likely to contribute in the first year. That's the reality.
Don't agonize over skills or best practices. Stop trying to find the "perfect" or "best" candidate. Pick the person who will:
- Expose your management blind spots the fastest
- Teach you what good hiring actually looks like, not what you think it looks like
- Show you where your team has gaps you didn't know existed
Pick your teacher, not your top performer.