MoneyINC Logo
Years of

10 Questions You Should be Asking a Mentor

speaking to a mentor

No matter how much we know (or how much we think we know), there comes a point when we could all do with a little extra guidance in our careers. That's where a mentor steps in. How you find your mentor isn't important. They could work within the same company as you, or they could be in a completely different business. It doesn't even need to be a formal mentor/mentee relationship. All that matters is that you're able to benefit from their experience and wisdom, something that will only happen if you know the right questions to ask to build an authentic, productive relationship. But remember - this is an ongoing relationship. Even if the first conversation goes with a bang, things can easily become repetitive if you run out of fresh material to talk about. Whether you're embarking on a new relationship or looking to reinvigorate an existing one, keep things interesting with these 10 questions to ask a mentor.

1. Was there a time you felt like you'd failed? How did you bounce back?

As Forbes recommends, to break the ice, ask your mentor a question that will lead to a story about their own career. No one can resist talking about themselves, and if you pose the right question, you might get a valuable insight into how to tackle similar situations in your own career. Failure is an inevitable part of everyone's journey, and while it's difficult, it's how you bounce back from the failure, rather than the failure itself, that defines you. Asking them about how they manage failure in their own life and career will not only tell you more about them, but could serve as a useful lesson in how to manage your own setbacks.

2. How do you spend your time?

Asking for advice from your mentor is one thing, but to truly make the most of the relationship, it needs to be a two-way street. Questions that help build an authentic connection are crucial. Asking them how they spend their time will tell you about their family, their hobbies, and about them as a person. Refer back to what they tell you in the future - remember, the more you give, the more you get in return. If they answer the question by focusing more on how they manage their time from a work perspective, do as recommends and use it as an opportunity to learn more about how they prioritize their time. Ask them for any tips and tricks they have to stay focused that you can then apply to your own routine.

3. What used to be your biggest weakness?

Self-awareness is crucial in a good mentor. How they answer a question like this will tell you a lot about whether they're a good match for you or not. It may even help you realize some of your own weaknesses, and learn more about how to tackle them. Without self-awareness, we'll never be able to recognize what may have led to mistakes and failings in the past, or put the tools in place to guard against the same happening in the future.

4. What would you do if you were me?

Your conversations with your mentor aren't a job interview. Don't waste your time or theirs by trying to impress them with how clever and capable you are. Tell them about specific challenges you're facing and ask for their advice on how to tackle them. There's only so much you can learn from books and courses: having a mentor means you get to ask for real-time advice about real situations, so make sure to take advantage of the opportunity.

5. How do you set goals?

Everyone does things slightly differently, but that's one of the key benefits of having a mentor: learning a new approach. There's no guarantee their approach to setting goals will work for you in the same way it does for them, but you could wind up picking up some hints and tips to incorporate into your own strategy.

6. How do other people see me?

True self-awareness is a tricky business that can take years to master. Mentors can provide a shortcut by holding up a mirror and letting you see yourself as others do. By providing a truthful account of your strengths and weaknesses, your mentor can help you take the first step in enhancing the former and overcoming the latter. It's not always easy to listen to an honest appraisal, but just remember that your mentor has your best interests at heart - if you can listen to their answer with an open mind, you'll be one step closer to improving your skills and your reputation.

7. Can I reach out to you with follow-up questions?

As says, never leave a mentor meeting without the promise of a future encounter. By asking them if you can contact them with follow-up questions, you're keeping the chain of communication open. That said, it's important to set boundaries and not to become burdensome. Let them know you'll only reach out with relevant, specific questions - most mentors will feel comfortable enough with that to agree.

8. How do you unwind?

Burnout is real. Regardless of their job or industry, everyone needs to find a way to unplug. Ask your mentor how they unwind after work. You might pick up some tips that could help you develop more positive relaxation habits.

9. What programs or organizations are you involved with?

Your mentor is likely to be involved in a variety of professional organizations and programs that may be of benefit to you. Your mentor will help you evaluate what organizations are likely to be most beneficial, and could even help get you an invite to an exclusive invite-only group.

10. Could I shadow you?

As writes, spending time with your mentor in their environment can teach you a lot. Theory can only take you so far, whereas shadowing is an excellent way to learn the ins and outs of the business in a practical way. Even if your mentor works in a different industry, it will still provide a valuable opportunity to gain an insight into how someone with more experience organizes and plans their workload, communicates, presents themselves, and tackles problems. Watch out for any tips and techniques you could apply to your own work. Most of all, enjoy the experience - learning new things is the way to stay ahead of the curve, but this is also an opportunity to bond with your mentor.

Lily Wordsmith

Written by Lily Wordsmith

Lily Wordsmith is a freelance writer who has had a love affair with the written word for decades. You can find her writing blog posts and articles while sitting under a tree at the local park watching her kids play, or typing away on her tablet in line at the DMV. In addition to her freelance career, she is pursuing ebook writing with an ever-growing repertoire of witty ebooks to her name. Her diversity is boundless, and she has written about everything from astrobotany to zookeepers. Her real passions are her family, baking desserts and all things luxe.

Read more posts by Lily Wordsmith

Related Articles

Stay ahead of the curve with our most recent guides and articles on , freshly curated by our diligent editorial team for your immediate perusal.
As featured on:

Wealth Insight!
Subscribe to our Exclusive Newsletter

Dive into the world of wealth and extravagance with Money Inc! Discover stock tips, businesses, luxury items, and travel experiences curated for the affluent observer.
linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram