Questions to Ask Your Role Model
These are questions to ask someone you admire when you finally get the coffee, the mentoring call or the school interview: a teacher, a coach, a relative, or a person in your field you look up to from a distance. The 57 questions run in the order a good talk goes, from how they started and what their days are really like, through hard choices and the values behind them, to what they have changed their mind about and the advice they would give you. They are written to get past the tidy version of the story to the trade offs, the luck and the things they quit.
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The questions
Each question, and why to ask it
Starting out
What were you doing at my age, and how much of it looked like a plan at the time?
Why ask it
Almost nobody's path was legible while they were on it. Hearing the uncertainty at the equivalent stage is more reassuring, and more accurate, than a story told backwards from where they ended up.
Who did you look up to when you were starting out?
Why ask it
People who are looked up to nearly always had someone of their own, and they tend to enjoy being asked. Follow with what they borrowed from that person and what they chose not to copy, because the second half is where their own style began.
What first made you think you could do this?
Why ask it
The answer is often small: a teacher's passing remark, a first paying customer, a result nobody expected. It tells you what counted as evidence for them at the stage where you may still be waiting for permission.
Who helped you early on, and what did they actually do?
Why ask it
Push for the specific act: an introduction, a piece of blunt feedback, a name passed to someone hiring. The general answer about great mentors is not usable, the specific one tells you what help looks like when you go asking for it.
What did you find hardest in your first year?
Why ask it
First-year trouble is often less about ability than about loneliness, money, not knowing who to ask or being the least experienced person in the room. Compare whichever they name with what you are finding hard now.
What did you want to be before this?
Why ask it
A dropped ambition makes the route look less like destiny. Ask what carried over from the earlier plan, since skills from the abandoned thing often turn up in the work they are known for.
What did the people at home think of the path you chose?
Why ask it
Support and doubt at home shape early choices more than most life stories admit. Leave room for a short reply, since for some people this is a sore subject, and move on if they keep it brief.
Was there a point where you nearly went a different way?
Why ask it
Nearly every route has a fork that was close: a job offer, a move, a course they almost took. What tipped it shows you what they were weighing before they knew how things would turn out.
What did you get lucky with?
Why ask it
People who can name their luck quickly, whether it was timing, a family situation or someone who took a chance on them, know which parts of the story were not their doing, and their advice is easier to trust for it. If they say none, ask what would have happened had one early break gone the other way.
Day to day
What does a normal week look like for you?
Why ask it
The gap between the admired version of a job and the daily reality of it is usually large. Anyone considering the same route needs to know how much of it is meetings, admin and waiting.
What part of what you do would surprise someone who only sees the results?
Why ask it
From outside you see the finished thing: the lesson, the match, the book, the well-run shop. This asks for the preparation and repetition behind it, which is the part you would be signing up for.
What part of your work do you still look forward to?
Why ask it
Admiration tends to fix on the achievement, and this asks about the enjoyment. If the part they love is one you would dread, such as the travel, the performing or the long hours alone, it is better to learn that before you copy the route.
Is there a skill you built on purpose that paid off more than you expected?
Why ask it
You are asking for something you could start this month. Answers tend to be unglamorous: writing clearly, reading numbers, speaking to a room. Plain skills like those keep paying because nearly every later job uses them.
What do you still practice, even now?
Why ask it
Someone you admire can look finished from a distance. Hearing that they still drill a basic, rehearse a talk out loud or ask a colleague to check their work makes your own practice feel less like a sign of being behind.
What are you not good at, and how do you work around it?
Why ask it
The workaround is the interesting part: a partner who covers it, a system, a rule about never doing a particular task. Weakness without a workaround is a complaint, weakness with one is a method.
How do you know when you are out of your depth?
Why ask it
The question is about self awareness, not confidence. The signals people describe are often ones you can recognize in yourself: avoiding a document, talking faster, going quiet in meetings.
Whose opinion of your work do you actually care about?
Why ask it
The list is usually very short, and hearing it shrinks the imagined audience you may be performing for. Why those people and not others is the follow-up worth having ready.
What do people in your line of work say that you think is wrong?
Why ask it
It invites them to disagree with their own field's received wisdom, and that is where independent thinking shows up. Someone who cannot name anything may be repeating the consensus without having tested it.
What do you do on a bad week?
Why ask it
The question is mundane on purpose, and the answer is often the most useful one of the conversation. What someone reaches for when the work is going badly is a habit you can repeat, which is not true of their talent.
Which habit would you keep if you had to drop all the others?
Why ask it
Asking for one forces a ranking, and the winner is usually plain: sleep, a morning hour with no phone, writing things down. One habit is also about as much as anyone carries away from a single conversation.
Hard choices
What is a decision of yours that looked reckless at the time?
Why ask it
This gets at their real relationship with risk, including how it felt while the outcome was still unknown. Ask what they had in reserve, because most bold moves turn out to have had a floor underneath them.
What did you give up to get here?
Why ask it
Cost is the part usually edited out of the story. A frank answer about years, health, relationships or another ambition lets you decide whether you want this particular life, not just this particular result.
When were you closest to giving up, and what kept you going?
Why ask it
Pay attention to whether it was a person, a deadline, a bill to pay or plain stubbornness. Honest answers here are often less noble than the public story, and that makes them easier to use.
Which failure still bothers you?
Why ask it
Asking what they learned from failure invites a rehearsed answer, and this does not. Something that still stings has not been turned into a lesson yet, and that is where the honest detail lives.
What criticism was hard to hear and turned out to be fair?
Why ask it
You learn how they take being wrong, and that is worth copying more than any technique. Who said it, and how long it took them to admit it had a point, are the two details to listen for.
What is a mistake you made with a person rather than with the work?
Why ask it
Work mistakes get retold as lessons, while the ones involving a colleague, a friend or a family member usually go unmentioned. If they answer, thank them and do not dig: it is a generous thing to tell someone younger.
How do you decide when to quit something?
Why ask it
Persistence gets discussed endlessly and quitting almost never, yet the second is the harder skill. Listen for an actual test, such as a deadline, a number or a feeling they have learned to trust, in place of a slogan about grit.
What do you say no to now that you would have said yes to ten years ago?
Why ask it
The answer traces how their judgment changed as options increased. It also gives you a practical filter to borrow, since most people's difficulty is not finding opportunities but declining the wrong ones.
What did you do when people you respected thought you were making a mistake?
Why ask it
Sooner or later you will make a choice that someone whose judgment you trust dislikes. Find out whether they went ahead quietly, argued it out or waited, and whether the relationship survived the disagreement.
Values
What do you refuse to do, even when it would be easier?
Why ask it
A line somebody holds is clearer than a value they can name. Ask when it was last tested, because a rule that has never cost anything has not really been a rule yet.
When has doing the right thing cost you something?
Why ask it
This is the question that separates the person you admire from their results. If they can name the price, whether a lost client, a friendship that cooled or a promotion that went elsewhere, you know what their principles are worth to them.
Who taught you how to treat people?
Why ask it
Mostly it comes down to a parent, a first boss or a coach, and often a single scene they still remember. If the way they treat people is part of why you look up to them, say so here: it is a compliment few people ever hear.
How do you decide what to do when nobody is going to check?
Why ask it
Most of what makes someone worth admiring happens unobserved. They may describe a test they run on themselves, such as whether they would be comfortable explaining the choice to one particular person.
What do you do after you have let someone down?
Why ask it
Everyone does it, including the people on your pedestal. How soon they own up, what they say and what they do to put it right add up to a script you can borrow the next time it is your turn.
How do you keep praise from going to your head?
Why ask it
Being admired is its own pressure, and you are part of it. Some keep an old friend who is not impressed, some keep doing a humbling task themselves, and either is a workable defense once people start praising you.
What do you want the people closest to you to say about you?
Why ask it
The reply is almost never about achievements. Compare it with what the wider world praises them for, and notice which of the two they sound like they are working harder on.
How do you feel about being someone's role model?
Why ask it
Say it plainly first: you are one of mine. Many people are uneasy with the idea, and what they say next, usually a list of their own flaws, is a useful correction to the picture you have built of them.
What about the way you live or work should I not copy?
Why ask it
A person you look up to is a package, and some of it you should leave out: the hours, the temper, the years with no holiday. Only they can tell you which parts they would not wish on you.
Then and now
What have you changed your mind about in the last few years?
Why ask it
It is hard to answer with a script, which makes it a good test of whether someone is still learning. Note whether the change concerns their field, their ambitions or how they treat people.
What did you believe about success at twenty five that turned out to be wrong?
Why ask it
Anchoring it to an age makes the answer concrete rather than philosophical. It often lands on assumptions about recognition, money or how much any single achievement changes daily life.
What took you the longest to learn?
Why ask it
Slow lessons are usually about people or about themselves, not about the craft. Ask what finally made it land, since the trigger is often a single bad day you might be able to learn from secondhand.
What mattered a great deal to you once that you have stopped caring about?
Why ask it
Titles, being liked by everyone, winning arguments: whatever they dropped is a candidate for something you are spending energy on right now. What took its place is the second half of the answer.
What do you understand about your own parents or teachers now that you did not then?
Why ask it
It turns the conversation toward the people who shaped them, and the tone often softens. It suits a role model who is a relative, a teacher or a coach especially well, because they have now stood on both sides.
Looking back, what are you proudest of that most people never saw?
Why ask it
You could look up the public achievements before you arrive. The private answer is often a person they helped, a problem fixed quietly or a hard year they got through, and it is a better guide to what they count as success.
What are you still trying to work out?
Why ask it
An unfinished question shows the person behind the reputation. It can be practical, like how to hand work over, or personal, like how to slow down, and either way it puts the two of you a little closer to level.
What do you want to be doing in ten years that you are not doing now?
Why ask it
The answer reminds you that they are still in the middle of it, which undoes some of the pedestal effect. Now and then it also surfaces something they need help with, and that is how these relationships become mutual.
Advice
What is the best advice anyone gave you, and did you take it at the time?
Why ask it
The second half is the real question. Good advice often sits unused for years, and hearing how long it took them makes it easier to forgive yourself for the advice you are not ready for yet.
If I wanted to end up somewhere like this, what would you tell me to ignore?
Why ask it
This gets you further than asking what to do, because the standard advice is easy to find and the noise is what wastes years. Expect specific answers about credentials, networking rituals or particular platforms.
What mistake do you see people my age making most often?
Why ask it
They watch people at your stage from an angle you cannot get. Take the answer as a pattern to check yourself against and not as a verdict, and ask what the ones who avoid it do instead.
From what you know of me, what am I not seeing about myself?
Why ask it
Only worth asking a role model who has watched you work, study or play. Stay quiet after you ask and do not defend yourself, because the first honest observation is usually followed by a more useful second one.
What is one thing I could start this week that you wish you had started sooner?
Why ask it
A deadline of this week keeps the advice small enough to do. Write down the exact thing they say, then tell them you will report back, which gives you a reason to get in touch again.
What is worth being patient about, and what should I stop waiting for?
Why ask it
Younger people tend to rush what takes years and delay what could be done on Monday. Their sorting of the two will be particular to their field, so ask for an example of each from their own life.
What makes you want to help someone who asks for your time?
Why ask it
You are asking for the rules of the game from the other side of the table. The reply, usually preparation, a specific request and proof that earlier advice was used, tells you how to approach the next person you admire.
Is there someone you think I should meet or learn from?
Why ask it
A name costs them very little and can change your year. If they offer an introduction, make it easy by sending two lines they can forward, and let them know afterwards how the meeting went.
Is there a book or a talk that shaped how you think and that I could find for myself?
Why ask it
It gives you something to start the same evening and a reason to write again once you have finished it. Find out what they took from it before you begin, since two readers rarely take the same thing from one book.
Is there something you wish people asked you about?
Why ask it
It works as a closing question because it hands over control: admired people tend to be asked the same few things again and again. What they choose often turns out to be the most candid part of the conversation.
Would it be all right if I told you how it goes?
Why ask it
It turns a single conversation into the start of one, without asking for a commitment as large as mentoring. It is an easy thing to agree to, and the update a few weeks later is what they will remember you by.
Getting a Real Conversation, Not an Interview
Practical guidance for the conversation itself
Setting It Up
Ask for something small and specific
Twenty minutes about one topic is far easier to grant than a general request for mentorship. Name the topic in the request, and say why you are asking this person rather than anyone with a similar job.
Do the homework they can tell you did
Read or watch the obvious things first and reference one of them in your first two minutes. It proves you are not asking them to repeat what is already public, and it changes the level the conversation starts at.
Pick your three questions in advance
A twenty minute conversation holds about three real questions, and the list above is meant to be chosen from rather than worked through. Take them from different groups, and decide which three matter most for the decision you are actually facing.
Which Groups Suit Which Role Model
Someone you know well: a parent, a teacher, a coach
You already have the access, so the risk is that the talk stays at its usual level. Say that you want to ask some proper questions, then choose from Values and Then and now, the two groups that people who see you every week rarely get asked about. Leave Advice to the end: they have probably been giving you that for years.
Someone in your field you have never met
Open with one question from Starting out that shows you know their story, spend the middle on Day to day and Hard choices, and keep the last five minutes for Advice. Hold Values back for a second meeting unless they open that door themselves.
A school or college assignment to interview someone you admire
Starting out and Hard choices give you the story, and one answer from Values gives the write-up its point. Ask before you record, tell them who will read or hear the piece, and check any quote with them before you hand it in.
Two minutes after a talk or at an event
Take one question, chosen before you reach the front, and make it something they did not cover on stage. The practice question from Day to day and the one in Advice about what to ignore both fit in a breath and still get a real reply.
During the Conversation
- Ask for an example every time you get a principle. What happened is where the useful detail sits.
- After a hard question, count to three before you say anything. A role model who is thinking will often add the half of the answer they were going to leave out.
- Do not ask them to solve your specific situation. Ask how they would think about it, then do the deciding yourself.
- Resist arguing when the advice does not fit your circumstances. Note it, ask what has changed since, and move on.
- Finish early rather than late. Ending at eighteen minutes is how you get a second conversation.
Afterwards
- Send a short note within a day naming the one thing you are going to act on. Vague thanks are forgotten, a specific commitment is not.
- Actually do that thing, then report back in a month with what happened. This is the whole basis of an ongoing relationship.
- Write down what surprised you while it is fresh, particularly anything that contradicted what you assumed.
- Treat their route as one data point rather than a template. What worked in their industry a decade ago may not transfer.
- Never quote them publicly without asking, especially the candid parts.