Fun Questions to Ask Female Leaders
Twenty questions for a mentorship coffee or a panel: the advice that sounded wrong until it worked, the skill they wish they had picked up earlier, what a failure taught them, and the leadership myth they would retire.
The questions
Open any question for the note
What did you think this job would be, before you had it?
Why ask it
An easy opener that avoids the career-ladder recap they have given a hundred times. Most leaders expected more deciding and got more explaining, and the gap between the two is where the useful conversation starts.
What's the best advice you've been given that sounded wrong at the time?
Why ask it
The qualifier matters. Asking for the best advice gets a poster quote; asking for advice she initially rejected gets the story of what changed her mind, which is the part anyone can actually learn from.
What's the most ridiculous thing you've done in the name of productivity?
Why ask it
A deliberate deflation of the leadership-profile tone, and most people have a spreadsheet, an app or a 4am experiment they now find funny. It also tends to reveal what she was anxious about at that point in her career.
What's a skill you use constantly that nobody trained you in?
Why ask it
Aims at the invisible parts of the job: chairing a room, writing a hard email, reading a budget, handling a supplier. Answers show which gaps her organization expected people to fill on their own time.
What's one skill you wish you'd picked up earlier?
Why ask it
Better than asking for regrets, because the answer is actionable for whoever is listening. Watch for whether it is technical or interpersonal, since the answer often reflects what her sector rewarded early on.
What's the funniest thing that's gone wrong in an important meeting?
Why ask it
A story rather than a lesson, which is a relief mid-conversation. Broken video calls, a wrong deck, a fire alarm at the worst moment. It also shows how she recovers in front of people, which is a real leadership signal.
What's a leadership myth you'd happily retire?
Why ask it
Invites a strong opinion, and the myth she picks is usually one she was personally measured against. Notice whether she attacks the myth or the people who repeat it, because those are different kinds of leader.
What do you do when you don't know the answer in front of your team?
Why ask it
Practical, and the honest answers are specific: saying so plainly, naming who will find out, or buying a day. Anyone who claims never to be in that position is describing an ideal rather than a Tuesday.
What's your actual approach when you feel out of your depth?
Why ask it
Phrased to ask for method rather than feelings, which gets past the standard imposter syndrome answer. Expect something concrete: preparing twice as hard, calling one trusted person, writing the thing down before saying it.
What's the best small purchase you've made for your working life?
Why ask it
Genuinely useful and easy to answer, and the answers are often unglamorous: a second monitor, a better bag, noise-cancelling headphones, a cleaner calendar. It also breaks up a run of heavier questions.
What did you learn from a failure that you couldn't have learned any other way?
Why ask it
The final clause is the important part. It blocks the tidy answer about resilience and asks what specifically was only visible from inside the wreckage. Expect something about warning signs she can now spot early.
Who did you copy, and what exactly did you take from them?
Why ask it
Sharper than asking about role models, because it asks for a behavior rather than a name. How someone ran a one-to-one, how they closed a meeting, how they said no. The specific borrowed habit is the transferable part.
Whose career would you swap into for a week?
Why ask it
Reveals curiosity, and in the reasoning, what she is tired of. Some pick a field they admire, some pick one they imagine is quieter, and the difference tells you something about her current load.
What have you learned about building a team that isn't all like you?
Why ask it
Asks about practice rather than principle, so the answer is about hiring processes, meeting formats and who gets heard, not about values. Vague answers here usually mean it has not actually been worked on.
How do you decide what not to do?
Why ask it
Most leadership advice is about doing more. This asks for the subtraction method, and the good answers are systematic: a standing rule, a person who screens, a question she asks before agreeing to anything.
What's a decision you defended that you'd reverse now?
Why ask it
Harder than admitting a mistake, because it involves having argued for it publicly. Placed late for that reason. It is the clearest test of whether she can update in front of an audience.
How do you recover after a bad week, and does it actually work?
Why ask it
The second half stops the polite answer about balance. Some methods are real, some are aspirational, and a leader saying honestly that her recovery plan gets eaten every month is more useful to hear than a routine nobody can copy.
What's your guilty pleasure show, book or playlist?
Why ask it
A deliberately light question after two serious ones, and it works because it needs no thought. It also tends to be the answer people in the room remember and mention afterwards.
How do you celebrate a win with your team, and what have you noticed people actually value?
Why ask it
The second half is where the useful detail is. Answers usually reveal that the expensive gesture landed less well than a specific piece of public credit, or an afternoon off.
What question do you wish people asked you instead of the ones they do?
Why ask it
Closes by handing over the agenda, which is fair after twenty minutes of yours. The answer is often a request to be asked about the work rather than about being a woman in the work, and it is worth acting on.
Running a Mentorship Coffee or a Panel Well
Practical guidance for the conversation itself
Set It Up Properly
Ask about the work first
If the first three questions are about being a woman in leadership, the whole conversation becomes about that, whether or not she wanted it to. Start on decisions, craft and the job itself, and let her raise gender when and if it is relevant to her answer.
Send two questions in advance
The failure question and the reversed-decision question both improve enormously with a day's notice, because the honest version needs recalling rather than inventing. It also lets her decline one privately instead of on stage.
Say how long you need, and stick to it
Thirty minutes with four good questions gets you more than an hour that runs over. Ending early is a courtesy that gets you invited back.
On a panel, do not ask everyone the same question
Four people answering the same question produces three agreements and a repetition. Assign different questions from this page to different panellists, and tell them which is theirs beforehand.
What to Leave Out
- Whether she can have it all, how she balances it, or who looks after her children. None of these get asked of men in the same chair.
- Questions about her appearance, clothes, voice or how she is perceived in a room.
- Asking her to speak for all women in her industry, or to explain a statistic about them.
- Asking her to describe discrimination she has experienced, especially on a stage or in front of colleagues. If she raises it, follow her lead.
- Whether she considers herself a role model, which forces a no-win answer.
- Salary, equity and whether she was paid less than a predecessor.
- Comparisons to the one other well-known woman in her field.
Getting Past the Prepared Answer
Ask for the instance, not the principle
Any answer about culture, feedback or hiring becomes useful the moment you ask when that last happened. The specific meeting, the specific hire. Principles are interchangeable; instances are not.
Ask who else was in the room
Leadership stories are told in the first person even when a team did the work. Asking who else was involved brings in the people she relies on, and often produces the more interesting half of the story.
Let the silence run after the hard ones
The questions about a reversed decision and a failure both need a pause. Filling it with a follow-up gets you the safe answer instead of the real one.
Close with something she can decline
Ending on what she wishes people asked gives her control of the last word. Do not follow it with a request for a mentorship commitment in front of an audience. Ask that privately, in writing, with a specific and small ask.