The most useful questions to ask a mentor pass two tests. They’re specific enough to answer in a few minutes, and big enough to change what you do next week. “Any advice?” fails both. So below are 30 questions grouped by stage and goal, with notes on when to use them. That way you can walk into your next session with a plan instead of a blank page.
Looking for a mentor to ask? Kradoz matches you with people who chose mentoring as their goal, and a chat opens only when both people say yes. Free, Android for now.
How to use these questions to ask a mentor
Don’t bring all 30. Instead, pick two or three per session and send them a day ahead, so your mentor has time to think. Also add one short paragraph of context: where you are, what you’ve tried, and where you’re stuck. Good context gets you a specific answer rather than a general one.
During the call, write the answers down. Then, at the start of your next session, report what you did with them. That small habit tells your mentor their time made a difference, and that feeling is a big part of why people keep mentoring.
Questions to ask a mentor in your first meeting
The first meeting is about fit and expectations, so keep these light:
- What do you wish someone had told you when you were at my stage?
- How did you decide to make the biggest move in your career?
- What does a good mentoring relationship look like from your side?
- Would you prefer short email updates between calls, or should I save everything for our sessions?
- From what I’ve told you, where am I underestimating the work ahead?
Question 5 is the one people skip, but it’s often the most valuable. It invites honest pushback early, before you’ve built habits around a wrong assumption.
Questions to ask a mentor about career development
Once you know each other, move to questions that shape your next six to twelve months:
- Which skills made the biggest difference to your career, and how did you build them?
- If you were in my role, what would you focus on for the next six months?
- How do you decide which opportunities to turn down?
- Who else should I learn from, and would you be comfortable introducing me?
- What mistake do you see people at my level make most often?
Question 9 can open doors, so ask it only after a few sessions. By then your mentor knows your work well enough to vouch for it.
Questions to ask a mentor at work
An internal mentor knows your company’s unwritten rules, so use that inside knowledge:
- What do people who get promoted here do that others miss?
- Which projects get noticed by leadership, and which ones quietly disappear?
- How should I raise a disagreement with my manager without hurting the relationship?
- Who outside my team would be worth getting to know this quarter?
- When you look at my work, what would you change first?
Keep these questions to ask a mentor at work inside your sessions, not in public channels. They work because your mentor can speak frankly in private.
Questions to ask a mentor about leadership
These suit new managers, team leads and anyone stepping up:
- How did you handle your first difficult conversation as a manager?
- What makes feedback land, in your experience?
- When your team disagrees with a decision you’ve made, what do you do?
- How do you protect time for focused work?
- Did your leadership style change as your team grew, and if so, how?
Ask for stories rather than rules. “Tell me about a time” questions usually reveal more than “What’s your approach?”
Questions for founders and startup mentors
The questions to ask a mentor change once you’re building a company. Here, your mentor’s past mistakes are worth more than their wins:
- Which early warning signs would make you stop or change direction?
- How did you find your first ten customers?
- When did you know it was time to raise money, and when did you wait?
- If you started again, what would you look for in a co-founder?
- Which part of my plan would an investor question first?
For question 24, it helps to read our guide on finding a technical co-founder first, so you can compare notes.
Questions for research and academic mentors
Researchers, PhD students and postdocs face a different set of trade-offs:
- Which journals or conferences should my work aim for, and why?
- How do you choose collaborators outside your own institution?
- What makes a grant proposal stand out?
- How do you balance teaching, research and service?
- Looking at my publication plan, what would you change for the next two years?
Collaboration across borders is common in research, so a mentor’s contacts matter here. If you’re looking beyond your own lab, Kradoz also works as a research collaboration platform. For conferences and cold emails, see our guide on how to network in academia.
How to ask the harder questions
Some topics feel awkward, such as pay, failure or office politics. Still, a good mentor expects them. A few ways to make them easier:
- Ask for ranges, not numbers. “What pay range would you expect for this role in Amsterdam?” is easier to answer than “What do you earn?”
- Ask permission first. “Can I ask you something a bit personal about how you handled being laid off?”
- Ask about patterns. “How do people usually get promoted here?” works better than asking about one named colleague.
If your mentor works in another country, ask about local norms too. Hiring, raising money and even how fast people reply to email can differ a lot between, say, Riyadh and Manchester. Our guide to cultural differences in networking covers the basics.
After the session: close the loop
Within a day, send a short thank-you note with one action you’ll take. Then, before the next call, share what happened when you tried it. That turns a single good conversation into a relationship.
For the other side of the table, Anthony Tjan’s Harvard Business Review article, What the Best Mentors Do, is worth reading before your next session.
Frequently asked questions
What questions should I ask a mentor in the first meeting?
Start with fit and expectations. For example, ask what they wish they’d known at your stage, how they like to stay in touch, and where they think you’re underestimating the work.
How many questions should I bring to a mentor meeting?
Two or three is enough for a 30-minute call. More than that, and you’ll rush the answers that matter.
What should you not ask a mentor?
Avoid anything a quick search could answer. Also, don’t ask them to find you a job outright. Instead, ask what would make you a stronger candidate.
How often should you meet with a mentor?
Once a month suits most people. If you’re in the middle of a big change, such as a new role or a fundraise, every two weeks can work for a short while.
Bring better questions, get better answers
The right questions to ask a mentor turn a polite chat into advice you can use. Pick three from this list, send them ahead, and report back afterward. Haven’t asked anyone yet? Start with our guide on how to ask someone to be your mentor. If you’re still looking for someone to ask, you can find a mentor for free using our guide, or get Kradoz on Google Play and set mentorship as your goal.
