Skill is relatively easy to assess. You can look at a track record, check results, and ask technical questions. Character is harder. Most senior candidates are polished, prepared, and good at saying the right things. The trick is to get past the prepared answer and into what happened.
Here are the questions I find most useful, organized around the five values I listen for: calling, integrity, servant leadership, care for people and stewardship. For each one, I've included what to listen for.
A note on method
Ask about specific past situations, not hypotheticals. What would you do tells you what someone thinks you want to hear. What did you do tells you who they are. When you get an answer, keep going. Ask what happened next, who else was involved, what they would do differently, and how it ended. The third follow-up is usually where the real story lives.
Calling
Tell me about the work you've found most meaningful. What made it more than a job?
Why this company, and why now? What would make it worth your best years?
Listen for whether the person has thought about what their work is for. Leaders with a sense of calling talk about the people they served and the mission they believed in. Be cautious if every answer comes back to title and pay.
Integrity
Tell me about a time you made a mistake that no one else would have caught. What did you do?
Tell me about a time your boss or owner asked you to do something you were not comfortable with.
Listen for whether the person disclosed the mistake on their own, and whether the story has a cost. Integrity that never costs anything isn't being tested. Be cautious of answers where the candidate is always the hero.
Servant leadership
Tell me about a time you put the needs of your team or a customer ahead of your own goals.
Who is someone you helped develop who went on to do something great? What was your part?
Listen for specifics about other people. Leaders who serve tend to remember names, details, and outcomes for the people around them. Leaders who don't tend to drift back to their own accomplishments.
Care for people
Tell me about the hardest conversation you have had with someone on your team.
Tell me about someone you had to let go. How did you handle it, and how did they feel about it afterward?
Listen for both care and courage. Leaders who care for people don't avoid hard conversations. They have them early, clearly, and with respect. If someone has never let anyone go, or speaks about it with no emotion at all, ask more.
Stewardship
Tell me about a goal you missed. Walk me through what happened.
Tell me about a problem that wasn't yours that you decided to fix anyway.
Tell me about a decision you made that was better for the long term even though it hurt in the short term.
How have you handled company money or resources that were under your control?
Listen for the word I in the hard parts of the story and the word we in the successes. Stewards take responsibility for misses, give away credit for wins, and can explain the tradeoffs they made with other people's money. Be wary of a long list of reasons why it was someone else's fault.
Questions that cut across everything
A few questions reveal a lot regardless of the value you're testing:
What would your last three direct reports say about working for you? What would they say you need to work on?
Why are you open to leaving your current role? What would make you stay?
What kind of owner or CEO do you work best with, and what kind do you struggle with?
The last question is especially useful for Integrator and #2 roles. The fit between a Visionary and an Integrator is personal, and both sides should be honest about it early.
What not to ask
Never ask about religion, family plans, age, health, national origin, or any other protected characteristic, even casually over lunch. It isn't relevant to values, it exposes you to legal risk, and it signals the wrong things to good candidates. Values show up in behavior. Ask about behavior.
Pair the interview with references
Use the same questions with references. Ask a former direct report to describe how the candidate handled a hard conversation. Ask a former peer about a time the candidate took ownership of a problem. When the reference stories line up with the interview stories, you can trust what you heard.
Scoring what you heard
After each interview, take ten minutes alone before you talk with anyone else. For each of the five values, write down the specific story the candidate told and what it showed you. If you can't point to a story, you don't have evidence yet. Mark it as unknown, not as a pass. Then compare notes with the rest of your team. This keeps a charismatic candidate from winning on presence alone, and it keeps a quieter candidate from being overlooked.
Do this with your own judgment and your team. Don't hand it to software that scores people. Character is read in context, by people who know the company and the role.
Why this matters
A leader whose character fits your company makes everyone around them better. A leader whose character doesn't fit will eventually cost you more than any skill they bring. The extra effort in the interview is small compared to the cost of getting it wrong.
Where introductions help
Good interviews matter, but so does starting with the right people. If you're an owner of a Maryland growth-stage company looking for a senior leader, a short conversation is a good place to begin.