Unique Questions to Ask Leaders
Twenty questions for a skip level, a panel, a podcast or a conversation at a conference, written to get past the answers a leader has given a hundred times and onto how they actually operate.
The questions
Open any question for the note
What does your calendar say about your priorities that you wouldn't say out loud?
Why ask it
Time is the only allocation a leader cannot fake, so this gets you their real priorities rather than their stated ones. Most people laugh and then answer honestly, often about how much of the week goes to one relationship or one problem.
Which meeting would you cancel permanently if there were no consequences?
Why ask it
A light question with a serious answer underneath about what they consider theatre. If they name a meeting they themselves run, you are talking to someone unusually candid, and the rest of the conversation will go well.
What decision are you sitting on right now?
Why ask it
Live and unresolved, which means there is no prepared version. You will not always get the substance, and even the shape of it tells you what they find hard: choices about people, about money, or about admitting a direction was wrong.
How do you find out when something's going badly, and how fast?
Why ask it
Asks about the mechanism rather than the value, so it cannot be answered with a line about open doors. Look for named channels and named people, and for whether the bad news reaches them in days or in quarters.
Who on your team would tell you that you're wrong, and how did they earn that?
Why ask it
A leader who cannot produce a name has an answer whether they realise it or not. The second half is the better half, because how someone earned the right to disagree describes exactly what this leader rewards.
What's the part of this job you're worst at?
Why ask it
Distinct from asking about weaknesses, which has a rehearsed answer, because it is about the job's specific demands. Honest answers tend to be about firing people, public speaking, or reading a room they are not in often enough.
What have you changed your mind about in the last year, and what changed it?
Why ask it
The second clause is the test. A leader who can name the evidence, the person, or the failed project that moved them is describing a real process; one who only names the new belief is describing a preference.
What did you have to stop doing to do this job?
Why ask it
Every step up is a trade, usually of the work they were good at for work they are not yet good at. The answer tells you whether they still grieve the old job, which explains a great deal about where they interfere.
When you disagree with a decision you have to carry out, what do you do?
Why ask it
Gets at the part of leadership nobody puts in a talk: how they represent a decision upward and downward when they lost the argument. Watch whether they distance themselves from it in front of their team, which they may admit to.
What's something you believe about this work that most people in your field would argue with?
Why ask it
Asks for a position with a cost attached, not a contrarian slogan. If the answer is something everyone in the industry already says, they are managing the conversation rather than having it, and you can ask what it costs them to hold that view.
When you promote someone, what are you actually looking at?
Why ask it
The single most useful question here if you work for them, because the honest answer often differs from the published criteria. Ask for the last person they promoted and what tipped it, which converts a policy answer into a real one.
How do you tell the difference between someone struggling and someone in the wrong role?
Why ask it
A genuinely hard judgment that separates experienced managers from confident ones. Good answers describe a period of time, specific support offered, and what they looked for afterwards; weak answers describe an instinct.
What's a decision that looked wrong for a long time before it looked right?
Why ask it
Better than asking about failure, which every leader has a polished story for. This asks them to describe holding a position under sustained doubt, and whether they can say how close they came to reversing it.
What's the last thing you got wrong in public, and what did you say about it?
Why ask it
The second half is what matters, because how a mistake was communicated is the part their team actually experienced. An answer with no public acknowledgment in it tells you how safe it is to be wrong around them.
What do you tolerate now that would have bothered you ten years ago?
Why ask it
Reveals whether experience produced patience or resignation, and the two sound alike until you ask for an example. Some leaders will admit this is the thing they like least about themselves now.
What advice do you give that you don't follow yourself?
Why ask it
Almost everyone has one, usually about hours, boundaries or delegation, and admitting it takes more candour than a story about failure. A denial here usually means the conversation has stayed on the surface.
What do you spend your own time on that nobody would notice if you stopped?
Why ask it
Asks them to audit their own work honestly, and the answer is often a report, a forum or a ritual that persists because they started it. How willingly they examine this predicts how they treat other people's low value work.
Who taught you the most, and what did they do differently?
Why ask it
Ask for the behaviour, not the person, or you will get a name and a compliment. The specific thing they describe, whether it was how someone gave feedback or how they held a room, is usually what this leader is still trying to imitate.
What would you want the team to say about you after you've moved on?
Why ask it
A better closing question than asking about legacy, because it is about the people who worked for them rather than about their record. Compare the answer with what you have observed, and the gap is the most useful thing you will take away.
What should I have asked you that I didn't?
Why ask it
Hands them the floor and often produces the most direct thing said in the whole conversation, because they choose the subject. It also works as a graceful ending when you are out of time.
Getting a Real Conversation With a Leader
Practical guidance for the conversation itself
How to Ask
Ask about mechanisms, not values
Any question about what they believe has a prepared answer. Questions about how something happens, who tells them, how often and what they did last time do not, because the specifics were never rehearsed.
Ask for the most recent example, not the best one
Every leader has one polished failure story kept ready. Asking for the last time rather than the biggest time gets you the unpolished version, and the difference between the two is where the useful material is.
Two follow ups, then move on
The first answer is the summary, the second is the actual thing, and the third begins to feel like cross examination. When and who tipped it are the two follow ups that work on almost anything here.
One question, and let the silence sit
Stacking two questions together lets them answer the easier one, which is the most common way these conversations go flat. Ask, then wait.
Be specific about what you have seen
If you work for them, naming one concrete thing you observed gets a far better answer than a general question. It also shows you are not fishing.
Choose the Setting Deliberately
One to one or skip level
The only place the promotion question and the disagreement question get honest answers. Ask two, not ten, and say at the start that you are curious rather than raising a problem.
In front of a group
Expect the public version of every answer, because the audience is part of the answer. Choose the questions that are fine to answer publicly, like the meeting they would cancel or the advice they do not follow.
On a recording
Say up front what is being published. Leaders are far more forthcoming when they know which parts are on the record, and the offer to check a quote costs you nothing.
At a conference or in passing
You have one question, so pick the one you most want answered rather than an opener. The calendar question and the what should I have asked question both work cold.
What Makes a Leader Close Up
- Questions that are really performances. A long question with your own achievements embedded in it is transparent, and they hear several a week.
- Asking about people rather than about decisions. Anything that requires them to evaluate a named colleague will be declined, and it costs you the rest of the conversation.
- Asking about confidential matters in a group. Even a willing leader cannot answer, and putting them in that position is remembered.
- Treating an honest answer as an admission. If they name something they are bad at and you follow up as though you have found a flaw, you will get the polished version for everything after.
- Doing nothing with the answer. If you ask what they are looking at when they promote someone and then act exactly as before, you have spent the credit for nothing.