Leadership Questions to Ask
Twenty questions to put to someone who leads people, in a mentoring chat, a panel or a skip-level. They cover deciding without enough information, conflict between colleagues, telling someone their work is not good enough, delegation, announcing unpopular changes, and who develops the leader.
The questions
Open any question for the note
When you strip the title away, what is the job actually?
Why ask it
A good opener because it cannot be answered from a template. Some describe removing obstacles, some describe deciding, some describe recruiting. Whatever they name is what they will be judged on internally, and it frames every later answer.
How do you decide when to decide? What tells you that waiting for more information has stopped paying?
Why ask it
Look for a trigger they can state: a date, a cost of delay, a point where the team stalls. Leaders without one tend to decide when the pressure becomes unbearable, which their teams experience as lurching.
Tell me about a decision you made with less than half the facts.
Why ask it
Forces a story instead of a philosophy of decision-making. The useful detail is what they did to limit the downside: a pilot, a reversible step, a date to revisit. If the story ends at 'it worked out', ask what they would have done if it had not.
How do you get people to say what they actually think while you are in the room?
Why ask it
Specific mechanisms beat statements about openness: asking the most junior person first, writing before discussing, leaving the meeting. If the answer is that their door is always open, ask when someone last disagreed with them out loud.
What do you do first when two of your people are in conflict?
Why ask it
The first move tells you their model. Separate conversations, a joint meeting, or waiting to see if it resolves each carry a different cost. Ask how long they let it run before intervening, since that is where most managers get it wrong.
How do you tell someone their work is not good enough without losing them?
Why ask it
Ask for the actual wording. Leaders who have done this well can usually quote themselves. Vague answers about being direct but kind often mean the message was softened until the person never understood there was a problem.
What does accountability look like on your team when something is missed?
Why ask it
You are listening for whether it lands on a person or on a process, and whether the leader takes any of it publicly. A team where mistakes are only ever systemic has no accountability, and one where they are only ever personal has no learning.
What do you do when someone is a strong performer and a poor colleague?
Why ask it
This is the case that reveals what a leader really rewards. Watch for whether they have ever acted on it, and how long the behavior ran before they did. Most people have a story here and most stories involve waiting too long.
How do you know when it is time to let someone go, and when have you given up too early?
Why ask it
The second half is the part that gets an honest answer, because almost every experienced manager has one they wish they had backed for longer. What they say they were missing at the time is the transferable lesson.
How do you decide what to delegate and what stays with you?
Why ask it
Look for a rule rather than a case-by-case instinct: anything reversible, anything they have done twice, anything not requiring their authority. Leaders who keep whatever they enjoy tend to have teams who feel underused.
What do you do when delegated work is going wrong but has not failed yet?
Why ask it
The hardest moment in delegation, and the answer separates coaching from taking over. Ask what they said, whether they set a checkpoint, and what they would have let happen if the person had not course-corrected.
How do you build trust with someone who wanted the job you were given?
Why ask it
A concrete situation rather than a general question about trust. Good answers involve naming it early and giving the person real scope. If they say they simply focused on the work, ask where that person is now.
What do you do with a team that did not trust the manager before you?
Why ask it
You learn how they handle inherited damage: what they promised, how small they started, how long it took. Leaders who describe arriving with a plan and a new structure usually made it worse first, and it is worth asking whether they did.
How do you announce a change people will not like?
Why ask it
Listen for sequence and honesty: who is told first, whether the reasoning is given, whether they admit the parts they disagree with. A leader who claims everyone came round quickly is either fortunate or not being told what people think.
What do you do when your team is right and your own manager is not?
Why ask it
Tests whether they carry disagreement upward. Ask what they took up, in what form, and what happened. Leaders who only ever relay decisions downward lose the team's belief in everything else they say.
How do you handle knowing something you cannot yet share?
Why ask it
Reorganizations, departures and deals all create this. The workable answer is saying that there is something they cannot discuss and when they expect to be able to. Leaders who bluff instead get caught, and then nothing they say is trusted.
The last time something failed, what did you say to the team?
Why ask it
The words at that moment set whether people bring the next problem early or hide it. Look for whether they took responsibility in front of the group, and whether anyone was named. Compare their answer with how quickly bad news reaches them now.
Who is worth developing, how do you spot them, and what do you actually invest?
Why ask it
The third part is where claims about growing people meet reality: hours, projects handed over, introductions made. If the investment is all encouragement and no scope, the development is not happening.
How do you keep long-term work alive under short-term pressure?
Why ask it
Look for a mechanism: protected capacity, a named owner, a proportion of each cycle. Intentions do not survive a bad quarter, so ask what they gave up last time the pressure came, since something always gives.
How do you avoid becoming the bottleneck, and who tells you when you are?
Why ask it
Ends the conversation on their own limits. The interesting answers name a specific person or signal, such as decisions queuing while they are on holiday. If nothing comes to mind, they are probably the bottleneck now.
Adapting these to the setting
Practical guidance for the conversation itself
Where you are asking
A panel or all-hands
Public settings reward questions about craft rather than about people. Ask about deciding without full information, or announcing unpopular changes. Anything about firing, conflict or their own manager will get a careful non-answer with an audience present.
A mentoring conversation
Here you can ask for the cases: the person they let go too late, the delegation that went wrong. Bring a live situation of your own so their answer can be aimed at something real.
A skip-level with your manager's manager
Stick to how decisions are made, how they hear bad news, and what they expect from teams like yours. Avoid anything that reads as a complaint about your own manager, since you will not control where the answer travels.
Getting past the polished version
- 1Ask for one instance, not a pattern. 'The last time' and 'tell me about a case' cut through practised answers.
- 2Request the words. 'What did you actually say?' is the single most useful follow-up in this list.
- 3Ask about the counterfactual. 'What would you have done if it had not worked?' finds out whether it was judgment or luck.
- 4Ask who disagreed. Every real decision had an objector, and how they describe that person tells you a great deal.
- 5Accept the discretion. If they decline to discuss a named person, that is the correct answer and you should move on.
Turning the answers into something you use
- Collect wording, not principles. Phrasings for hard conversations transfer between organizations. Values statements do not.
- Ask several leaders the same two questions. Where their answers diverge is where the real choices in leadership sit.
- Watch for advice that only works with their authority. Some approaches need seniority you do not have yet, and applying them early reads as arrogance.
- Test one thing within a fortnight, while you still remember why it sounded right, then write down what happened.
- Notice the advice you resist. It is usually pointing at the part of the job you have been avoiding.
Common mistakes
Asking what their public talks answer
If it is in a conference session or an internal blog post, read that first and ask what has changed since. Repeating a question they have answered publicly wastes your slot.
Turning it into a debate
Challenging their approach in the first conversation gets you a defence rather than an explanation. Ask what conditions their approach depends on instead.
Collecting advice you never apply
Notes from six leaders and no change in your own practice is the usual outcome. Leave every conversation with one concrete thing to try.
Taking every answer at face value
Self-reports about openness, trust and feedback are the least reliable part of any leader's account. Where you can, compare with how their team describes the same thing.