Questions to Ask Your Hero
Twenty questions for the conversation you get with someone you have admired from a distance: a mentor, a figure in your field, a person whose work changed how you work. Written for short, one-off conversations where the usual questions produce a rehearsed answer.
The questions
Open any question for the note
What were you doing just before the thing people know you for?
Why ask it
Almost nobody asks this, so it rarely gets the polished version. The years immediately before the visible success usually contain the actual method, and they are frequently unglamorous: a bad job, a long stretch of nothing working.
What did the earliest version of your work look like?
Why ask it
Asking to see the bad first draft is flattering rather than rude, and the answer recalibrates your own expectations. If they claim the first attempt was already good, treat that as a story rather than a fact.
Who taught you the part of this you couldn't have worked out on your own?
Why ask it
Separates real influences from the ones they cite in public. It also usually surfaces a name you have never heard, which is often more useful to you than anything they say about themselves.
What does an ordinary Tuesday actually look like for you?
Why ask it
The unromantic question that produces the most transferable answer: hours, order of tasks, what they refuse to do before lunch. Compare it against what they recommend, because the two rarely match.
What did you have to give up for this?
Why ask it
Every version of this life has a bill attached, usually in health, money, family time or a place they left. Hearing the cost stated plainly is how you decide whether you actually want their career or just their reputation.
Who told you no, and what did you do about it?
Why ask it
Rejection stories are usually specific and well remembered, which makes them the most concrete answers you will get. Listen for whether they went around the no, waited it out, or changed the work in response.
What decision looked reckless at the time and turned out right?
Why ask it
Watch for survivorship. Ask how many people they know who made the same call and did not land well, since that single follow-up separates useful advice from a story about luck.
What decision looked sensible and turned out badly?
Why ask it
The harder half of the pair, and the reason to ask both. People who can describe a cautious mistake are usually reliable about the rest, since it is the one kind of failure nobody tells for effect.
What do people thank you for that you'd forgotten doing?
Why ask it
Often the most affecting question you can ask someone whose work has mattered to strangers. The answer tends to be small, a letter, a phone call, five minutes, which is quietly instructive about where influence comes from.
Who else deserves credit for this that nobody mentions?
Why ask it
Generous people answer this immediately and at length. Reluctance or a change of subject is worth noting too. Either way you get the names of collaborators who are usually far more approachable than they are.
What part of your reputation is wrong?
Why ask it
Most admired people are slightly miscast in public and know exactly how. It is a relief to be asked, and correcting the record is more interesting to them than repeating it.
What did the hardest stretch cost you outside of work?
Why ask it
Keeps the conversation from becoming a career interview. A vague answer here is fine and should be left alone. A specific one is a real confidence and should not be repeated afterwards.
What would you do differently if you were starting now?
Why ask it
Better than asking for general advice, because it forces them to account for how much has changed since their route existed. Discount any answer that describes a path only available in their era.
What did you believe at twenty-five that you'd argue with now?
Why ask it
You are asking for a change of mind rather than a lesson, which is harder to fake. Someone who cannot name one has either stopped revising or is giving you the public version.
What advice do people ask you for that you no longer believe in?
Why ask it
An unusually candid question that experienced people tend to enjoy. It also protects you: whatever they name is probably advice you have already been given by three other people.
Who do you go to when you're out of your depth?
Why ask it
Establishes that they still get out of their depth, which is worth hearing said aloud. The structure of their answer, one friend, a group, a paid advisor, nobody, is a model you can copy at your own scale.
Is there something in your work you're still nervous about?
Why ask it
Ask it gently and be ready for a deflection. If they answer, you learn that competence and nerves coexist permanently, which is more useful than any technique they could describe.
If you were at my stage, what would you spend the next two years on?
Why ask it
Give them your actual situation in two sentences first, or you will get generic advice. Specific circumstances produce specific answers, and this is the question most likely to change what you do next week.
What do you wish people asked you instead of the usual questions?
Why ask it
Hands them the conversation, which after fifteen questions is a courtesy. It also tends to produce the part they most want to talk about, and therefore the best material of the whole exchange.
Is there anything I can do for you?
Why ask it
Almost nobody offers, which is why it is remembered. Keep it genuine and small, since the answer may well be no, and a real offer to help is the closest thing there is to a reason for them to reply next time.
Making the most of a short conversation
Practical guidance for the conversation itself
Getting the conversation at all
- Ask for something small and specific. Twenty minutes about one topic gets accepted far more often than a request for mentorship.
- Say what you have already done with their work. It distinguishes you from the many people who admire them in general terms.
- Offer to come to them, fit their schedule, and name a date. Vague requests to meet sometime quietly expire.
- If there is no route to a private conversation, use the public one. Conferences, Q&A sessions and signings all leave gaps that most people fill with compliments rather than questions.
If you only get a minute
- Choose one question in advance and ask only that. Two questions in sixty seconds gets neither answered properly.
- Skip the biography. They know their own story, and time spent proving you have read up is time not spent hearing something new.
- Ask something answerable in a couple of sentences. "What were you doing just before this?" works. "What is your philosophy of life?" does not.
- Say thank you and stop. Ending early is remembered better than being the person who had to be extracted.
Questions that go down badly
- Anything about money or numbers. Even when the figure is public, asking for it changes the tone of the room.
- Requests disguised as questions: reading your manuscript, an introduction, a job. Ask for those separately and directly, if at all.
- Comparisons with a rival in their field. It puts them in the position of being diplomatic, which is dull for both of you.
- "What's your secret?" It concedes there is one and invites a slogan back.
During the conversation
- Take notes openly and say you are doing it. Most people find it flattering, and you will otherwise forget the specifics within a day.
- Ask permission before recording, and accept a refusal without negotiating.
- Follow up on what they said rather than moving to your next prepared question. The second answer on a topic is nearly always better than the first.
- Let silences sit. People reaching for an honest answer pause first, and filling the gap costs you the answer.
- Resist explaining your own work at length. You can send it later; the time in front of them is worth more spent listening.
Afterwards
- Send a short note within a day, naming one specific thing you are going to do differently. Concrete beats grateful.
- Do the thing, then report back a few months later with the result. That single follow-up is what turns a conversation into a relationship.
- Credit them accurately if you write about it, and do not repeat anything that was clearly said in confidence.
- Pass on what you learned to someone a stage behind you. It is the only form of repayment most people in this position actually want.