Explain it.
What problem did you choose to solve? Why does it matter?
For founders / People & leadership
7 Lessons I’ve
Learned About
Hiring.
Lessons I’ve learned about hiring, judgment and giving people room to do good work.
By Matt Hogan20+ years building businesses & teams · 7 min read
THE RÉSUMÉTitles.
Logos.
Credentials.
Logos.
Credentials.
LOOK DEEPERJudgment.Perspective.Ownership.
What will this person make possible?
I’ve built teams, led departments and worked across growth, ecommerce, operations and commercial strategy. I’ve also sat on the other side of the interview table. Both experiences have shaped how I think about hiring.
The question I keep coming back to is simple: what will this person help the business do better? That question changes the role you write, the people you consider, the interview you run and the way you lead after the offer is signed.
Start with the business
The job title
comes later.
“We need a marketing person” can mean a dozen different things. Someone to set direction. Someone to make content. Someone to run a channel. Someone to connect all of it to revenue.
My work with founders includes building hiring plans alongside priorities and accountability. Those belong in the same conversation. Before you write a job description, get specific about the work that is stuck and the decisions that have no clear owner.
A capable person can still be the wrong hire for an undefined job. Be honest about whether you need a specialist, a leader who connects functions, or someone who can build a function while doing the work.
BEFORE YOU POST THE ROLE
“Ninety days after this person starts, what should be meaningfully different?”
Read for substance
A career is
bigger than
a title.
My own career has crossed categories, channels and functions. That breadth has taught me how much a title can leave out: the scope someone carried, the decisions they owned and the problems they learned to solve.
For a founder, the person who connects marketing, operations and customer experience may be more useful than someone whose last title perfectly matches your posting. For a specialist role, depth may be exactly what you need. The point is to understand the work before choosing the filter.
Ask what the candidate actually owned. What changed because they were there? What did they inherit, build or repair? Where did they have to learn quickly?
ASK FOR THE REAL SCOPE
“What were you accountable for that your title didn’t capture?”
A lesson from my writing on AI & hiring
A polished assignment
is the beginning
of the interview.
If AI can do most of a candidate’s interview assignment, the assignment probably isn’t measuring the right thing.
AI can help organize thinking and communicate a recommendation. I use it that way myself. But the candidate still needs to own the thinking: the assumptions, the tradeoffs and the decision.
Defend it.
What did you rule out? Which tradeoff was hardest?
Adapt it.
The budget changes. A key assumption fails. What do you do now?
For senior hires especially, I want to understand how someone makes decisions with incomplete information. A live discussion about their work can reveal far more than another round of slide polishing.
Try this in your next interview
Use a small, fictional business scenario. Ask for a recommendation, then change one constraint during the conversation. Listen for the questions they ask, the assumptions they revisit and whether they can change their mind. Keep the exercise proportionate to the role and the candidate’s time.
Build a wider view
Familiarity
is a weak
hiring strategy.
In my writing about diversity and hiring, I’ve pushed back on the habit of looking for the same schools, companies and career paths over and over.
Different backgrounds bring different questions. Someone who has worked on a shop floor may notice a customer problem that a team looking only at a dashboard misses. A career changer may challenge an assumption everyone else accepts.
That doesn’t mean lowering the bar. It means being clearer about the bar: relevant capability, judgment, learning and contribution. A familiar résumé is not evidence of all four.
Customer
realityCommercial
judgmentOperating
experienceMore ways to see the problem.
realityCommercial
judgmentOperating
experienceMore ways to see the problem.
CHALLENGE YOUR FILTER
“Are we rejecting a capability gap, or just an unfamiliar path?”
A lesson from a mail route
Hire for
ownership.
Then give it.
Right out of school, I worked as a casual letter carrier for the USPS. There was good pay, plenty of overtime, a chihuahua bite and more than a few sunburns. It also gave me an early way to think about work: a route, a clear outcome and responsibility for getting it done.
Years later, that idea showed up in my writing about autonomy. People need to understand what they own. If every decision comes back to the founder, the job can become an approval queue.
When you hire someone for their judgment, make room for them to use it. Define the outcome, the boundaries and when to escalate. Then agree on a useful check-in rhythm.
Clear outcome+Decision room+AccountabilityOwnership that works.
THE FOUNDER’S QUESTION
“Which decisions am I actually prepared to let this person make?”
A hard lesson about people & performance
Big numbers don’t excuse
damaging behavior.
The cost of one toxic employee rarely stays inside their own job description.
I’ve seen how a damaging working relationship can consume a team’s attention. People start managing around one person: rehearsing conversations, avoiding collaboration, fixing preventable problems and spending energy on self-protection.
In my writing on this, I’ve made a point of calling out office politics. Tenure, relationships with senior leadership or strong individual results can make someone feel untouchable. Everyone else still has to work with them.
WHAT’S EASY TO SEEIndividual
results.
results.
WHAT ALSO COUNTS
- Trust lost across the team
- Time spent managing conflict
- Decisions delayed or avoided
- Good people disengaging or leaving
That is why I want a fuller definition of performance. How someone gets results matters. So does what happens to the people working beside them. A strong individual number can coexist with a weaker team.
This is also different from healthy disagreement. A person who challenges your thinking is not automatically toxic. Look at specific behavior: undermining colleagues, withholding information, disrespect or repeatedly refusing accountability. Make the expectations clear and follow through consistently, including with your biggest producers.
For founders, the lesson reaches beyond the hiring decision. If the team brings you a recurring problem, take it seriously. Giving a manager accountability without backing them on behavior standards leaves everyone stuck.
ASK BEFORE YOU MAKE AN EXCEPTION
“What is keeping this person costing the rest of the team?”
Finish the job
The offer
isn’t the
finish line.
Hiring plans, priorities and operating rhythm are connected. A new employee needs access to the context behind the job: the customers, the economics, the people and the constraints.
I care about clear outcomes and team ownership. That means making the first stretch of work concrete. What should the person learn? What will they own first? Who can remove a blocker? How will we know the work is improving?
Before deciding someone isn’t working out, look at the conditions around them. Were the priorities clear? Did they have the authority, information and support to deliver? Accountability goes both ways.
MAKE SUCCESS VISIBLE
“What do they need from me to do the job I hired them to do?”
Put it to work
Before your
next hire.
Seven questions worth answering before you open the search. Check each one when you can answer it clearly.
0 of 7 clarified
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