Questions to Ask a Leader About Leadership
Twenty questions for a one-to-one conversation with an experienced leader about how they actually lead. Written for anyone about to take on their first team, or already running one and looking for a straight answer from someone further along.
The questions
Open any question for the note
Who was the first person you were ever responsible for, and how did that go?
Why ask it
First-management stories predate a person's current self-presentation, so they come out unpolished. You usually get the specific mistake, promoting a friend, avoiding one conversation for six months, and that is worth more than any framework they might offer later.
What did you get wrong in your first year of leading people?
Why ask it
Anyone who cannot name something is either very new or not being candid. The common answers, doing the work themselves, softening feedback into uselessness, mistaking being liked for being trusted, are also the mistakes most likely waiting for you.
What habit did you have to give up when you started leading?
Why ask it
The step into leadership is mostly a subtraction problem, and nobody warns you about it. Listen for what they gave up: hands-on work they were good at, being the fastest person in the room, knowing every detail. The loss is usually the hardest part.
How do you find out your team is struggling before someone tells you?
Why ask it
Bad news travels upward slowly and gets sanded down on the way. A leader with a real answer will name a specific signal they watch, meetings going quiet, work slipping without explanation, and a leader without one is probably being managed by their own team.
What is the last decision you made where you genuinely did not know the right answer?
Why ask it
This replaces a generic question about decision-making with a live example. You learn what they do without enough information: who they call, how long they wait, and whether they tell the team it was a close call or present it as obvious.
When the team's interests and the company's interests pull apart, how do you decide?
Why ask it
Most leadership advice pretends this tension resolves neatly. It does not, and the answer tells you whether they have thought about where they draw the line, or whether they will discover it in the moment while people are watching.
What do you do in the first ten minutes after you get bad news?
Why ask it
The first ten minutes set the tone for everything after, and leaders who have been through a few crises usually have a deliberate routine: say nothing, gather facts, tell one person. Someone who describes reacting immediately is telling you how their team learned to hide problems.
How do you tell someone their work is not good enough?
Why ask it
Ask about feedback in general and you get the sandwich. Ask about this specific conversation and you learn whether they name the gap plainly, whether the person hears it the first time, and how long they usually wait before saying anything at all.
Who tells you when you are wrong, and how did you arrange that?
Why ask it
The higher someone rises, the less disagreement reaches them by default, so this has to be built on purpose. A named person is a good sign. A vague claim about having an open door usually means nobody walks through it.
What separates the people you promote from the people you do not?
Why ask it
This gets at the real criteria, which are rarely the ones in the competency framework. Answers tend to reveal whether they reward output, judgment, or the ability to make their own life easier, and the third is worth noticing.
How much of your week goes to work only you can do?
Why ask it
The honest number is often small, and the gap between that number and their calendar is the most useful thing in this conversation. Listen for what fills the rest: meetings they were invited to out of habit, approvals nobody needs from them.
What have you handed off that you are still tempted to take back?
Why ask it
Delegation fails at the point of temptation, not the point of handover. Naming the specific thing they still itch to grab shows how they hold the line, and whether they have ever quietly reclaimed something without telling the person they took it from.
Which part of your job would surprise the people who report to you?
Why ask it
Teams build a picture of their manager's day that is usually wrong in one direction or another. The answer often exposes work that is invisible from below, defending headcount, absorbing pressure, or conversely how little control the leader really has.
How do you handle a strong performer who is hard to work with?
Why ask it
This is the test every leadership philosophy eventually fails. Watch for whether they have actually moved on someone talented, tolerated the behavior for years, or are currently living with it and describing the situation in the present tense.
What have you changed your mind about in the last two years?
Why ask it
Leaders repeat their views for a living, which makes revision rare and worth hearing. A concrete reversal, on remote work, on hiring senior, on how much structure a team needs, shows they are still processing evidence rather than defending a position.
When did you last lose someone you did not want to lose?
Why ask it
Resignations are the clearest feedback a leader gets, and how they narrate one tells you a lot. Blaming the market or the offer is a different answer from naming the point where they missed something, and both are informative.
How do you keep repeating the same message without sounding like a recording?
Why ask it
Nobody warns new leaders how much of the job is repetition, or how quickly it starts to feel hollow. Experienced ones have found a way to say the same thing in different registers, and that technique is directly borrowable.
What parts of the job drain you, and what do you do about them?
Why ask it
Every leader has a task they quietly avoid, and the avoidance costs the team something. The answer shows whether they have built a way around it, delegated it, or are still letting it pile up while telling themselves they will get to it.
What has this job cost you that you did not expect?
Why ask it
Ask about challenges and you get workload. Ask about cost and you get the real ledger: friendships that changed when they were promoted, information they can no longer share, decisions they carry alone. Worth hearing before you take the same trade.
What would you tell someone stepping into their first leadership role next month?
Why ask it
Placed last, after twenty minutes of specifics, this question gets a different answer than it would have got first. By now they are drawing on the examples they just described rather than reaching for advice they have given a dozen times.
Getting a straight answer about leadership
Practical guidance for the conversation itself
Before the conversation
Say what you are deciding
A leader will give you a speech if you ask a general question and a real answer if you tell them your situation. Open with the specific thing in front of you: a team you are inheriting, a person you cannot reach, a promotion you are unsure about.
Ask about incidents, not principles
Principles are rehearsed; incidents are not. Every question in this set can be sharpened by adding the words when did you last, and that small change moves the conversation from philosophy to evidence.
Pick five, follow the thread
Working through a list produces a survey. Choosing a few and asking what happened next produces something you can use. The second and third follow-up is usually where the useful detail sits.
What the answers tell you
- Watch the tense. Problems described in the past tense have been resolved; problems described in the present tense are still happening, whatever the framing suggests.
- Note whether people appear in the stories by name and role or as an anonymous the team. Leaders who think about individuals talk about individuals.
- Someone whose examples are all successes has either forgotten the failures or is not going to tell you about them. Neither makes them a useful source on hard cases.
- Advice that arrives as a slogan usually has no experience behind it. Ask for the specific time the slogan was tested.
- Their answers describe what worked in their context: a team of four is not a team of forty, and a startup is not a hospital. Ask what they think would be different in yours.
Where these conversations go wrong
Opening with a definition question
Asking what leadership means invites a set piece the leader has delivered before, and once they are in that register it is hard to get them out of it. Start with something concrete instead and let the philosophy emerge.
Asking about people they still work with
A leader cannot discuss a current report's performance with you, and putting them in that position ends the candor. Keep questions about difficult people at the level of pattern rather than person.
Nodding through advice you disagree with
The conversation gets more useful when you say your team is younger, or the pressure is different, or that approach failed for you. Pushing back politely is how you find out whether the advice holds outside their situation.
Leaving without a next step
One conversation rarely changes behavior. Before you finish, name the single thing you are going to try, and ask whether that sounds right to them. That is also what makes them willing to talk to you again.