Questions to Ask a Guest Speaker About Leadership
Questions for the Q and A after a leadership talk, whether at a company session, a class or a conference. Written to get specifics and stories out of a speaker rather than the points they already made from the stage.
The questions
Open any question for the note
What is a decision you got wrong, and how long did it take you to notice?
Why ask it
The delay is the interesting part. Speakers tell failure stories readily, but the time between the mistake and seeing it is what shows how they get feedback.
What is something you believed about leadership ten years ago that you no longer believe?
Why ask it
Asks for a revision rather than a principle. A speaker who cannot name one has either stopped learning or is giving you the keynote instead of an answer.
When you took over a team that did not want you, what did you do in the first month?
Why ask it
Requests a sequence of actions, not a philosophy. Watch for whether they started by listening or by announcing changes, and what that cost them.
Who told you something you did not want to hear, and what happened to them afterwards?
Why ask it
Every leader claims to want dissent. What happened to the person who provided it is the only evidence that matters.
What is the last thing you changed your mind about because of someone junior to you?
Why ask it
A specific instance is hard to invent. If the example is trivial, such as a wording change, that tells you how far the openness actually extends.
How do you tell the difference between a team that is quiet and a team that agrees with you?
Why ask it
Most leaders discover the difference too late. The practical signals they describe are the most portable thing in the whole talk.
What did you say to your team on the worst day you have had as a leader?
Why ask it
Asking for the actual words, rather than the approach, gets you something usable. Vague answers about transparency usually mean they said very little at the time.
How did you decide who to let go when you had to make cuts?
Why ask it
A hard question asked plainly, and speakers who have done it will usually answer honestly. The criteria reveal what they truly value in people.
What conversation did you put off for too long?
Why ask it
Delay in giving hard feedback is close to universal, and hearing a senior person admit it is more useful to an audience than advice about courage.
How do you give someone difficult feedback without them going home wrecked?
Why ask it
Asks for the craft rather than the principle. Listen for whether they mention what they say afterwards, which is the part most people skip.
What did you delegate that you found hardest to let go of?
Why ask it
The specific task, usually the one they were promoted for being good at, is more revealing than any general account of trusting the team.
How do you find out what is going on that nobody is telling you?
Why ask it
Practical methods differ widely, from walking the floor to skip-level meetings to reading support tickets. Any concrete habit is worth stealing.
When you had to carry out a decision you disagreed with, what did you tell your team?
Why ask it
This is the most common leadership bind and almost never covered from the stage. The answer shows whether they distance themselves or take ownership.
How did you know one of your people was ready for a bigger job?
Why ask it
Asks for the signals they look for, which is directly usable by anyone in the room who wants to be spotted.
What do you do when someone talented is damaging the team around them?
Why ask it
How long they tolerated it, and what finally forced their hand, tells you more about their standards than any statement about culture.
How do you manage a team you rarely see in person?
Why ask it
Worth asking for specifics, since the honest answers involve fewer meetings and more written updates than most leaders like to admit.
What do you do in the week after a project fails publicly?
Why ask it
The sequence, who they speak to first and what they say about blame, is the part audiences remember and rarely hear described.
How do you handle influencing someone more senior than you when you have no authority?
Why ask it
Managing upward is the skill most of the room needs and least often gets taught. Ask for a specific case rather than a technique.
What part of your job would you happily never do again?
Why ask it
Loosens the tone and gets an honest answer about the unglamorous parts of leadership, which is useful to anyone deciding whether they want the job.
What question do people in my position usually not think to ask you?
Why ask it
Hands the framing back to them at the end of a session. Speakers often use it to raise the thing they most wanted to say and were not asked.
Getting a good answer in a Q and A
Practical guidance for the conversation itself
How to ask
Ask for one instance, not a policy
How do you handle conflict produces a paragraph everyone has heard. Tell us about a time you handled conflict badly produces a story. Nearly every question above works better with a when or a what did you say attached.
Reference something they said
Tying your question to a specific point from the talk tells the speaker you were listening and lets them go a level deeper rather than repeating themselves.
Keep it to one sentence
Long preambles eat the time and usually contain the asker's own opinion. The shorter the question, the more room the answer has.
Follow up once if you can
The second question, what happened next, or how did the team react, is where the useful detail lives. First answers tend to be the polished version.
What not to do
Asking what is already in their bio
Career history and how they got started are usually published. Spending a limited Q and A on it wastes the only access the room has.
Making it about your own situation
A short version of your problem can work, but a detailed account turns the session into private consulting and loses the audience.
Asking two questions at once
Speakers answer the easier half and move on. Pick the half you actually care about.
Fishing for agreement
Questions built to confirm a view you already hold get a polite yes and no new information. Ask about the case where their approach did not work.