Questions to Ask a Mentor: 50 Examples, Grouped by Goal

The best questions to ask a mentor are specific to a decision you're facing and to the mentor's own experience. Bring three to five questions and one artifact to each session, and end by agreeing on one next step. Good starters:

• What would you do in my position this quarter?
• What did you wish you knew at my stage?
• What's the biggest gap you see in this [resume, portfolio, plan]?
• Which skill should I build next for [target role]?
• How did you handle [setback] when it happened to you?
• What should I do before we talk again?

This list is for anyone with a mentor call coming up, whether it's part of a formal program at work, a one-off session with someone you found online, or a coffee chat with a former manager. The questions are grouped by goal, so start with the section that matches where you are.

What is a career mentor?

A career mentor is an experienced professional, usually a few steps ahead in your field, who gives you advice, feedback and perspective on your career decisions. Unlike a manager, they don't evaluate you. Unlike a coach, they usually draw on their own path rather than a method.

Career mentorship is the relationship around that advice. It can be a formal program, a few calls a year, or a single conversation about one problem. It usually covers the practical moments of a career: running a job search, going for a promotion, switching fields, or closing a skill gap before it holds you back.

A mentor is also different from a sponsor. A mentor advises you; a sponsor uses their influence on your behalf, for example by putting your name forward for a promotion or a big project. Many people start with a mentor and earn a sponsor later. We cover that difference in our guide to career advancement strategies, and why career mentorship matters and what to look for in a mentor if you're still deciding whether it's worth it.

Questions to ask a mentor in your first meeting

A first meeting is mostly about context. You want to understand how your mentor got where they are and how they like to work, and they want to understand what you're trying to do.

Leave a little room for small talk. It's how rapport starts, and it makes the harder questions later feel less formal.

• How did you get to where you are today?
• What first drew you to this field, and what keeps you in it?
• What does a typical week look like in your role?
• What part of your job excites you most right now?
• What do you wish you had known before your first job in this field?
• What goal are you working toward at the moment?
• Why did you decide to become a mentor?
• How do you prefer to stay in touch between sessions?

Questions about their career path and setbacks

Every career has a few bad stretches: a rejection, a project that failed, a manager who wasn't a fit. Hearing how your mentor handled theirs gives you a plan before you need one, and it's often where the most useful advice comes from.

Ask for specifics: what happened, what they tried, and what they'd do differently now.

• How did you land your first job in this field, and what would you change about how you searched?
• Was there a time you made a mistake you thought might sink you? How did you recover?
• What's the most important lesson you learned early in your career?
• Which career decision are you most glad you made, and which one would you undo?
• Have you ever been passed over for a role or a promotion? What did you do next?
• When did you last feel stuck, and what got you moving again?
• Which setback ended up teaching you the most?
• How did you decide when to stay in a hard job and when to leave?

Questions about resources and skills

Your mentor's habits are often more useful than their job title. Find out what they read, who they learn from, and how they practice.

The point isn't to copy their routine. It's to find two or three sources you wouldn't have found on your own.

• How do you keep up with changes in your field?
• What are your favorite resources for getting better at your craft?
• Who do you follow or learn from, online or in person?
• Is there a course, certificate or community you'd recommend at my level?
• Can you recommend a book that will help me build [skill]?
• Which skill took you the longest to learn, and how did you practice it?
• What tools do you use every day that I should get comfortable with?
• If you were starting over today, what would you learn first?

Questions that get you honest feedback

Feedback is the part most people skip, because it's uncomfortable to ask for. It's also where a mentor helps most, since friends and colleagues tend to soften what they say.

Bring something concrete to react to, such as a resume, a portfolio, a plan or a recent piece of work, and ask what to fix first.

• What's the first thing you'd change in my resume or portfolio?
• How would you approach [a presentation, an interview, a salary negotiation] in my position?
• What new skills do I need to move ahead if I want to reach [goal]?
• From what you've seen so far, what are my strengths?
• Where do you think I'm underselling myself?
• If my application landed on your desk, what would make you hesitate?
• What blind spots have you noticed in how I talk about my work?
• What would this piece of work look like if someone one level above me had done it?

Questions to check your career goals and next steps

Every few sessions, or before a mentorship winds down, share your plan and ask your mentor to poke holes in it. They can't predict the future, and they're still adapting to changes in your field too, but they've seen enough careers to know which plans hold up.

This is also the place to agree how the two of you will work together.

• I'm planning to take [course or certificate] next year. Is it still worth the time?
• As a beginner in [skill], which tool would you start with?
• Will my current plan get me where I want to be in five years? What's missing?
• If you were me, what would you focus on for the next six months?
• Do you prefer short-term or long-term mentoring?
• How often can we meet?
• How can I better prepare for our next meeting?
• Can we review the goals for this mentorship together?

Questions to ask a mentor at work

A mentor inside your company knows things an outside mentor can't: how decisions really get made, who to talk to, and what the promotion process rewards in practice. Use that inside knowledge. A work mentor may also sit close to your manager, so agree early on what stays between the two of you.

• How are decisions actually made on this team, and who should I talk to before I propose something?
• What does the next level look like here in practice, beyond what the job ladder says?
• How can I make my work more visible to leaders outside my team?
• Which teams should I get to know, and could you introduce me to someone there?
• If I wanted to move to another team someday, how have other people here done it?

Questions to ask a mentor about career development

Career development questions are about your next two or three moves, not just your next task. They work best once you've named a target role, even a rough one, so your mentor can tell you what stands between you and it and how long that usually takes.

• What role would make sense for me next, and what's the gap between where I am and that role?
• Which skill gap would hold me back most over the next year?
• Would a lateral move help me right now, or should I aim for the next level where I am?
• How long did it take you to move from my level to the next one, and what sped it up?
• What should I start doing now to prepare for a role two steps ahead?

How to prepare (and what not to ask)

A little prep turns a pleasant chat into a useful one. A day or two before, send your mentor a short note with your goal, where you're stuck, and one artifact, such as your resume, a portfolio link or a plan. Pick three to five questions, put the most important one first, and write down the answers as you go. Before you hang up, agree on one next step.

Some questions use up the time without giving you much back. Here's how to turn them into better ones:

• Anything a search engine can answer. Instead of "What does a product manager do?", ask "What surprised you most about the job once you started?"
• "Will you be my mentor?" It asks for a big, vague commitment up front. Ask for one conversation about one problem and let the relationship grow from there. Our guide on how to find a mentor and ask for a session covers the wording.
• "Can you get me a job?" It puts your mentor in an awkward spot. Ask "What would make me a strong candidate for a team like yours?" instead. If they want to refer you, they'll offer.

A worksheet for your first meeting

The original version of this list drew on questions shared by mentor Janus Tiu, now a Senior Experience Designer at Electronic Arts. His worksheet, Preparing for your first meeting with your mentor, walks you through five steps: identify your purpose, research the person you're meeting, give them context, set goals and an agenda, and write your questions.

For the mentor's side of the table, read The Most Common Questions During My Mentorship Sessions by Seva Kurdiukov.