Fun Questions to Ask Senior Leaders
Twenty questions for an all-hands Q and A, a skip-level or a fireside chat with senior leadership. They stay light enough to ask in front of a room while still getting at career turns, advice that stuck, and what the person is like away from work.
The questions
Open any question for the note
What's the funniest thing that's happened to you at work?
Why ask it
A safe opener that lets a leader be a person for ninety seconds, which is usually what a room wants first. Anyone who reaches for a story where they come out looking impressive has told you they are still in presentation mode.
What's something you're surprisingly bad at?
Why ask it
Executives are heavily coached on how to answer weakness questions, so the tell is specificity. Spreadsheets, names, parallel parking: a concrete answer relaxes a room, and a strategic non-answer about caring too much does the opposite.
What job did you have before this that has nothing to do with what you do now?
Why ask it
Kitchens, call centres, farms, the army. This gets the part of a career that never appears on a slide, and it tends to explain more about how someone runs a team than their last three roles do.
Which part of your job would surprise people most?
Why ask it
Most people have no accurate picture of how a senior leader spends a day, and the honest answer is usually duller and more repetitive than anyone expects. That is exactly why it is worth hearing.
What did your first day here look like?
Why ask it
Everyone has a first day, so this puts the leader and the newest hire in the room on the same footing for a moment. Long tenured leaders often have not been asked in years and enjoy it more than the strategy questions.
What's the most interesting place work has sent you?
Why ask it
Ask for interesting rather than favourite and you get the strange trip rather than the nice hotel. It is also an easy question for a leader to answer while thinking about a harder one coming next.
What reliably makes you laugh?
Why ask it
The answers that land are specific: a comedian, a group chat, a particular colleague. Someone who cannot name anything is either guarding hard or genuinely does not switch off, and both are worth noticing.
How do you actually switch off after a bad day?
Why ask it
Junior staff read a leader's habits as permission, so a plain answer here carries weight. Watch for the answer that is really about working more, which tells a room the opposite of what the wellbeing slide said.
What's something outside work you're into right now?
Why ask it
Right now keeps this from becoming a rehearsed line about family and golf. Whatever they have picked up recently is usually where their curiosity currently sits, and it makes them easier to approach afterwards.
What's on your calendar that you'd cancel tomorrow if you could?
Why ask it
Light enough to laugh at and pointed enough to be useful, because leaders sit in the meetings they created. If they name a recurring meeting, half the room is sitting in one just like it.
Which meeting would you protect if everything else got cut?
Why ask it
The inverse question, and the more revealing of the pair. What a leader defends shows where they think the real decisions get made, which is not always where the org chart suggests.
How do you know when you've had a good week?
Why ask it
Some leaders answer with numbers, some with conversations, some admit they cannot tell. The answer predicts what they will notice about your work far better than any stated set of priorities.
What skill did this job force you to learn that you never expected?
Why ask it
Usually something unglamorous: reading a balance sheet, chairing a meeting, saying no in writing. It tells people earlier in their careers what the next rung actually requires rather than what the job description says.
What's the most interesting mistake you've made in your career?
Why ask it
Interesting rather than biggest gives them room to be candid without confessing. The good answers name a decision and what it cost; the weak ones describe a mistake that turned out well, which is not a mistake.
What's the best advice you were given, and did you actually take it at the time?
Why ask it
The second clause is what saves this from being a quotable platitude. Most people ignored the good advice for years, and hearing that is more use to the room than the advice itself.
What's the last thing you changed your mind about?
Why ask it
This is the question that separates leaders who genuinely revise their views from those who restate strategy. A specific, recent, slightly awkward answer is the good one; a vague answer about learning is not an answer.
What's a decision you made that looked wrong for a long time?
Why ask it
It surfaces how a leader sits with pressure and public doubt, which is the part of the job nobody sees. Expect a slower answer than usual, since these are rarely told as stories internally.
How do you find out how things are actually going, beyond the reports?
Why ask it
You learn who they listen to, and whether that group is broader than their direct reports. It also politely surfaces the gap every senior leader knows exists between the dashboard and the day.
If you weren't doing this job, what would you be doing instead?
Why ask it
The alternate life people describe usually names what their current role is short on: making things, teaching, being outdoors. It is a friendly question that lands closer to the bone than it looks.
What would you tell yourself on your first day in a leadership role?
Why ask it
Anchoring it to the first day of leading, not the start of the career, keeps the advice usable for anyone in the room who is a year in. Generic answers here are a sign the question needs a follow up about what specifically went wrong that year.
Asking these well in a real setting
Practical guidance for the conversation itself
It depends on the format
All-hands or panel with an audience
Pick the lighter questions from the top of the list and expect a polished answer. In front of a hundred people, a leader is managing risk, not reflecting. Ask one question, listen, and let someone else follow up; a two part question from the floor will only get its first half answered.
Skip-level, one to one
This is where the questions about mistakes, changed minds and how they know a week went well belong. Send the one question you most want answered a day ahead. Senior people give far better answers when they have had a walk to think, and it also signals you are not there to ambush them.
Fireside chat where you are the host
Order matters more than the list does. Two easy questions to warm up, the substantial ones in the middle while attention holds, and something human to close on. Write your follow ups in advance for the two answers most likely to be evasive.
Follow-ups that get past the prepared answer
- "What did that cost?" after a story about a mistake. It moves the answer from anecdote to consequence.
- "Who told you?" after any claim about how things are going on the ground. Names are more informative than the claim.
- "When did you realise?" after a changed mind. The timing usually reveals what actually changed it.
- Silence. Four seconds after an answer ends is the single most effective follow up available, and in a room it feels much longer than it is.
Reading the room and the risk
- Do not aim a light question at a heavy week. During a restructure or after bad results, a fun question in an all-hands reads as tone deaf, and the leader has to manage that for you.
- Anything touching layoffs, pay, an individual's performance or a live legal matter cannot be answered honestly in public. Asking it in that setting wastes the slot; take it to a one to one.
- Do not ask a question you have already published your own answer to. Leaders can tell when they are being set up, and the room usually can too.
- If they deflect, let it go the first time. One graceful retreat buys you a real answer later; pressing in front of an audience does not.