Good Questions to Ask Guest Speakers
For a careers day, a class visit or an assembly where the speaker came to talk about their job rather than an argument. These stay on the working life: how they got in, what an ordinary week holds, what it cost, and what they would do differently. If the talk was about a subject rather than a career, the set on Questions to Ask a Guest Speaker goes at the material instead.
The questions
Open any question for the note
How did you end up in this line of work?
Why ask it
A gentle opener that produces a story rather than a summary. Listen for whether the path was planned or accidental, because most speakers admit to at least one sideways step, and that is more useful than a tidy narrative.
What did your last week actually look like, hour to hour?
Why ask it
A talk describes the interesting five percent of a job. This pulls the rest into view: the meetings, the paperwork, the waiting on other people. If they cannot answer concretely, they may be further from the daily work than the talk suggested.
What part of your job would surprise the people in this room?
Why ask it
Invites them to name the gap between how the work looks and how it feels. Answers tend to land on tedium, internal politics, or how little of the day goes to the thing they are known for.
Was there a point where you nearly did something else instead?
Why ask it
Near-misses are where the real decisions sit. You hear what they weighed and what they gave up, which travels better than a list of achievements.
What did you have to learn on the job that no course prepared you for?
Why ask it
Names the actual skill gap for students in the room. Common answers are writing clearly, running a meeting, and delivering bad news, none of which appear on a syllabus.
Which of your early assumptions turned out to be wrong?
Why ask it
Forces a specific error rather than a gesture at growth. A speaker who cannot name one has either not reflected much or is managing their image carefully.
What is a decision you would make differently now?
Why ask it
Gets a concrete counterfactual instead of general advice. Notice whether they blame circumstances or own the call, which tells you how they think about responsibility.
When a project of yours failed, what happened next?
Why ask it
The aftermath is the interesting part: who told them, what it cost, whether anyone lost a job. A vague answer here usually means the failure is being filed under somebody else's name.
How do you tell useful criticism from noise?
Why ask it
Harder to deflect than asking how they handle criticism, because it demands a filter rather than a platitude. Strong answers name a particular person whose view they weight heavily, and say why.
What are you reading or following to keep up?
Why ask it
Gives the audience something to use the moment the talk ends. It also shows whether they are still learning or coasting on what they knew a decade ago.
What is a skill people in your field consistently undervalue?
Why ask it
Points at where an outsider could gain ground cheaply. Answers are usually unglamorous: taking notes, following up, being reachable when something breaks.
What does the entry-level version of your job look like day to day?
Why ask it
Students hear about the job the speaker has now, which is twenty years away. Asking about the first rung gets the version anyone in the room could actually walk into, and how long people usually stay on it.
Now that people ask you for things, how do you decide what to say yes to?
Why ask it
Reveals current priorities more honestly than a question about goals. It also quietly tells you whether an email from someone in this room would get opened.
What does a bad day in your job look like?
Why ask it
Balances a talk that has almost certainly led with the highlights. A concrete answer helps anyone weighing this career decide whether the bad days are ones they could live with.
Where do you think people in your field are getting something wrong right now?
Why ask it
Asks for a position rather than a survey. Watch whether they can disagree with their own profession in public, because that separates a practitioner from a spokesperson.
What has changed in your work in the last couple of years?
Why ask it
More answerable than a question about the future, and less prone to vague forecasting. The changes they name are the ones already affecting hiring and daily practice.
If you were starting today, what would you do differently?
Why ask it
Better than asking for advice in general, because it makes them account for how the entry route has changed. Be sceptical of answers that simply recommend their own path.
What kind of person does well in this field, and who tends to burn out?
Why ask it
The second half is the part nobody volunteers. Answers often describe the same trait doing both jobs, which is worth knowing before you commit years to it.
What is a piece of your work you are proud of that nobody talks about?
Why ask it
Lets them step off the standard story. What they pick shows their real standards, which frequently differ from whatever earned them the invitation to speak.
What would you want someone here to email you about?
Why ask it
Turns the Q&A into a possible contact rather than a dead end. A specific answer tells you what kind of message gets a reply, and a polite deflection is also a clear answer.
Asking well in a Q&A
Practical guidance for the conversation itself
In the room
Say the question, not your background
Most Q&A time is lost to people explaining who they are before arriving at a question. One sentence of context, then the question. Write it down while the speaker is still talking so you are not composing it under pressure.
Ask about the specific, not the field
Asking what trends they see produces something close to a press release. Asking what changed in their work in the last two years produces an answer. Quote a line from the talk and build from there.
One question, no stacking
Two questions joined by an and means they answer the easier half and the room moves on. Decide which half you actually want and ask only that.
Leave room for the answer
Do not fill the pause. Speakers often add their most candid sentence a few seconds after they seem to have finished.
If the room is quiet or the speaker is guarded
- Ask about last week rather than their career. A fixed timeframe breaks the habit of answering in generalities.
- Ask what they cut from the talk. It gives them permission to go off the script they rehearsed.
- Ask about a decision rather than a lesson. Lessons arrive pre-packaged; decisions have to be reconstructed.
- If they dodge, accept the dodge and move on. Pressing twice in public makes everyone else in the room stop raising their hand.
- If an answer is genuinely good, say so briefly and hand the microphone back rather than mining the same question a third time.
Questions to skip
- Anything already on their first slide or their public biography.
- Asking for advice for young people, which produces the same answer at every event they have ever spoken at.
- Your own opinion delivered with a question mark at the end. The room notices, and so does the speaker.
- Requests to comment on a named competitor or former colleague. You will get a non-answer and cost yourself the goodwill.
- Asking for a job, an internship, or feedback on your work in front of a full room. Ask what to email them about, then email within a day and reference something specific they said.