Leadership Questions to Ask Leaders
Twenty questions for a sit-down with an experienced leader, built to get stories rather than principles: what they got wrong early on, where their week goes, how they handle someone who is not performing, who tells them they are wrong, and how they judge their own work.
The questions
Open any question for the note
What did you get wrong in your first year of managing people?
Why ask it
Opens with a mistake, which sets the register for the rest of the conversation. Leaders who cannot name one either had an unusually easy first year or have polished it out, and both tell you how candid the next hour will be.
What part of this job did nobody warn you about?
Why ask it
The answers are rarely about strategy: they are about carrying other people's anxiety, or the loneliness of knowing things you cannot repeat. Whatever they name is the part you should be preparing for and probably are not.
Walk me through last week. Where did the time actually go?
Why ask it
Asking about a real week defeats the idealized answer. Compare the hours they describe with the priorities they claim, and you learn how much of a leader's calendar is genuinely chosen rather than inherited.
What do you delegate now that you would not have handed over five years ago?
Why ask it
This traces how their judgment about risk changed. If nothing has moved, they may be a capable individual contributor with a team attached, which is worth knowing before you take their advice on scaling anything.
How do you decide when to step in and when to let someone struggle?
Why ask it
Look for a threshold rather than an instinct: a deadline, a customer, a cost they will not let the team pay. Leaders without a stated line tend to intervene by mood, which their teams experience as inconsistency.
What do you watch in a new hire's first month that tells you how it will go?
Why ask it
You get their real hiring model, which is usually narrower and more specific than any competency framework: how someone asks for help, or what they do with a vague brief. Useful whether you are being hired or hiring.
How do you know someone is ready to lead before they have ever done it?
Why ask it
The honest answer usually includes a wrong call they made. Listen for whether their signals are about performance or about how people behave when the person is in the room, since those predict very different things.
When someone is not performing, how long do you give it, and what does the first conversation sound like?
Why ask it
Ask for the words. A leader who can recount the opening line of that conversation has had it often and takes it seriously. Vagueness here often means the problem gets managed by reassignment or by waiting for the person to leave.
How did you learn to deliver bad news, and who taught you?
Why ask it
Most people learned by doing it badly once. The story tells you what they now avoid, and naming who taught them shows whether they were developed deliberately or left to work it out, which shapes how they treat their own people.
Tell me about a time you had to carry a decision you disagreed with. What did you say to your team?
Why ask it
The specific wording is the lesson. Watch for whether they distanced themselves from the decision, which is the easy move and the one that quietly costs a team its trust in everything else they announce.
What do you do when a priority from above makes no sense to your team?
Why ask it
You are testing whether they translate, push back, or simply relay. Ask what they took upstairs and how it was received, since that is the difference between a leader with standing and one who is passing things through.
Where do you get honest information about how your team is actually doing?
Why ask it
Named channels are the good answer: one skip-level, a peer, a departing employee's exit conversation. A leader who says people always feel able to come to them is describing an intention, and it is usually not what their team reports.
Who tells you when you are wrong, and how did you make that possible?
Why ask it
The second half matters. If nobody has ever challenged them, that is the answer. If someone has, ask what they did the first time it happened, because that reaction is why it continued.
What is the last thing you changed your mind about because someone junior pushed back?
Why ask it
Requires a recent, concrete example, which is why it separates leaders who invite disagreement from those who only say they do. A story from years ago is worth noticing as much as no story at all.
Which decision still bothers you, and what would you do differently?
Why ask it
Usually a layoff, a hire kept too long, or someone they failed to defend. The regret they choose reveals what they value, and the corrective they name is the most usable advice in this conversation.
What do you do in the first two days when something has gone badly wrong?
Why ask it
Look for sequence: who they tell, what they stop, when they communicate before knowing everything. Leaders who have been through it describe a process. Those who have not describe a feeling.
How do you protect your team's attention when priorities above you keep moving?
Why ask it
Concrete mechanisms are the interesting part: a frozen sprint, a single point of contact, a rule about what gets committed each quarter. Without one, the churn passes straight through to the team, whatever the leader intends.
How do you tell whether you are doing this job well? What do you actually look at?
Why ask it
Watch whether their measures are about output only or include retention, whether people are being promoted, and how many decisions get made without them. The absence of any personal measure is common and worth asking about.
What has this job cost you outside work, and would you make the same trade again?
Why ask it
A serious question that most people answer honestly if you ask it plainly and late in the conversation. The trade they describe is the one you are considering, and it is rarely discussed at the point when you can still choose.
If I wanted a role like yours in five years, what should I be doing now that I probably am not?
Why ask it
Better than asking for career advice in general because it forces a specific gap. Push for one thing rather than a list, and ask what would show them, in six months, that you had done it.
Getting a real conversation with a senior leader
Practical guidance for the conversation itself
Setting it up
Ask for a narrow slot
Thirty minutes with two or three questions gets accepted more often than an open request to pick someone's brain. Say in the invitation what you want to talk about, so they can arrive with an example in mind.
Do not ask what they answer in public
Skip anything they have covered in a town hall, a podcast or a conference talk. Reference it instead: 'you mentioned that layoff decision at the all-hands, what would you do differently now?'
State your situation in three sentences, once
Give enough context that their answer can be specific, then stop. Long preambles turn a conversation with a busy leader into a monologue about you.
How to ask
- 1Ask for a story, not a philosophy. 'Tell me about a time' and 'what did you say' produce material you can use.
- 2Follow with 'what happened next'. Most leaders stop at the decision. The consequences are the useful half.
- 3Ask for the words in hard conversations. Wording is transferable in a way that principles are not.
- 4When you hear a platitude, ask for the exception: 'when has that not worked?'
- 5Leave the personal questions, cost, regret, until the last ten minutes, once they can see you are not collecting quotes.
- 6Finish on time. Ending early is what gets you a second conversation.
Reading the answers
- Recency. Examples from the past year mean the reflex is current. Examples from a decade ago may be describing a person they no longer are.
- Specific people, specific numbers, specific dates. Detail is the best available proxy for whether they were actually there.
- Whether the team appears in the answers. Leaders who narrate their own decisions with no one else in them tend to manage that way too.
- How they describe failure. 'We were unlucky' and 'I moved too slowly' are different diagnoses, and only one of them is teachable.
- What they refuse to answer. A leader who declines to discuss a personnel matter is showing you appropriate discretion, not evasiveness.
Afterwards
- Write it up the same day, in their words where you can. Advice loses its specifics fast.
- Pick one thing to change and say so in your thank-you note. It is the difference between a pleasant chat and the start of a mentoring relationship.
- Report back in a couple of months with what happened when you tried it. Almost nobody does this, and it is why almost nobody gets a standing invitation.
- Do not repeat anything they told you about a named person, even in general terms. One breach ends this kind of access permanently.