Questions to Ask a Mentor: How to Nail Your Next Mentor Meeting

Let’s say you’ve finally landed a mentor. You think the hard part is over? Think again. If he/she is willing to spend time with you, you now have to make sure you make the most of your time together. 

When it’s time to meet for a coffee for the first time you have to know that you’re going to have about an hour or so to do your magic. Their time is, after all, quite limited and you must navigate it efficiently and productively. What are good questions to ask a mentor? What do you say? How to prepare before your next mentor meeting? You will find the answer to these questions and more in the following paragraphs.

How to prepare for a meeting with your mentor?

You have to keep in mind that the main purpose of the mentoring relationship is to help with the progress of the mentee, meaning you. This means that in this newly-founded mentor/mentee relationship, you have to be the pro-active one. Don’t assume that just because your mentor is probably senior to you, they have to be in charge of shaping the agenda and deciding on what topics should get discussed. You have to take initiative. Think of your mentor as an available resource you have to utilize in a way to guide you to your final career destination. After all, they already had their career journey and became successful in their respective field. It’s your time now.

Create an agenda

As mentioned above, you are the one who will be shaping the conversation with your mentor. The more prepared you are, the better the meeting will go. Think of the topic areas you want to cover and what you’re going to need their help with. Think of why you’ve reached out to them in the first place. How do you think they might be able to  help you? Write down all of the discussion points and try your best to stick to them. Of course, in the course of the meeting, a dozen other things might come to your mind and the conversation can easily drift in another direction. Once the hour and the coffee is over, though, you can’t go back to your original agenda as time is, after all, precious. You might end up having to schedule another meeting and you will go home with unanswered questions. Therefore, as intriguing as it is to find out as much as you can in one hour, do your best to follow the meeting outline you’ve prepared.

Think of it as a business meeting

It’s not just a simple cup of coffee with your senior, it’s also a business meeting. It’s good to be friendly and casual but you have to also remember who stands in front of you. Let’s say your mentor is a CEO of a successful company who was kind enough to dedicate time to hear you out and answer your questions. Don’t make them figure out by themselves what to talk about. You don’t want to leave a bad impression by looking unprepared and unprofessional. If you don’t showcase preparation and leadership skills, they will be less inclined to advocate for you.

Be clear and straightforward

Start the meeting strong and avoid too much “chit chat”. Get down to business and lay out your agenda for the meeting. Set the tone of the meeting by saying the following:

  • I’d appreciate it if you can give me advice on ….
  • I wanted to update you with how things went after I took your suggestion and advice you gave me last time… 

Ultimately, you should aim at providing the essence and tell your story in a straightforward and direct manner. You are looking for their help on specific issues after all. You can’t go wrong if you build a reputation for being a concise communicator with problem-solving abilities 

⚫ Have realistic expectations

Unrealistic expectations or assumptions can easily derail your relationship with your mentor. To leave out disappointing results, have a straightforward discussion on what your expectations are of each other and the relationship. For instance, talk about how often you’ll meet or what specific areas you will work on. Of course, what you’ve agreed upon early on in the relationship will definitely change later. However, you should keep having conversations that discuss expectations. 

⚫ Think of your reputation

It’s been established that you’re the one responsible for leading the mentor meeting. With that being said, you have to make sure you manage your time and discussions well. You want to be seen by your mentor as a natural-born leader with organizational and communication skills. Make sure you end on time and come prepared. If possible, try to finish the meeting as early as you can. This will definitely leave a good impression as you’re actually giving them some time back. 

having a meeting with a mentor and asking questions to your mentor

How often should I meet with my mentor? 

Ultimately, you can’t have a mentoring relationship without a schedule. You and your mentor should create a particular time to talk, discuss, evaluate and more. The amount of time you will meet with your mentor depends entirely on them and the type of mentoring you’re going for. If it’s more informal, you can do it based on personal schedule and informal arrangements. If it’s a formal mentoring, you would have to wait for the organization to determine that. 

A weekly meeting is usually perfectly acceptable. If, however, your mentor is a CEO or runs dozens of businesses, you have to understand that scheduling a mentor meeting once or twice per month would be more than generous.

What are some good questions to ask a mentor?

❓How do you spend your time on a daily basis? 

The goal of asking this question is to set a positive tone of the meeting by digging a little bit into their personal and professional life. Ask them how they manage to balance their work and personal lives with so many things happening to them professionally. Moreover, you can also add a question about how they manage to run so many projects or a company on a daily basis. This set of questions will prove that you have a genuine interest in this person, their success story and what does a regular day look like for such an accomplished person. 

❓What would you do if you had to deal with these challenges? (What would you do if you were me?)

Don’t waste your time trying to impress your mentor by listing all of the great things you did and how you found a solution to every problem you had. Tell them about specific issues you are currently dealing with. Ask for their recommendations. After all, you  want advice, not a stage.

❓Are you associated with any professional organizations and in what ways?

Your mentor got where they are now by going to the right conferences and trade associations. A good mentor will recommend the right conferences and professional associations you can join. If you are lucky enough, they can get you access to “invite only” events and groups. 

❓Would you please tell me who else would you recommend I connect with? 

Sometimes, one mentor won’t be able to answer all of your questions or give you a thorough explanation or answer to a challenge you’re dealing with. Therefore, they might refer you to a colleague or another senior mentor they’ve worked with. Ultimately, this would be a great chance to expand your network. 

❓Are there any books or literature that you would suggest I read? 

This question shows that you’re ready to do your homework and want to know as much as possible about the issue at stake. In addition to asking about books, you can also ask about great websites, online learning centers, webinars, youtube channels, etc. 

❓Did you fulfil all of your professional dreams? 

Your mentor might laugh or at least smile when you ask this question but it’s a great way to fill in any silent gaps that might occur during the course of your conversation. The way they got to their current career level is always an interesting story to hear. They might share some of the mistakes they’ve made or things you can definitely learn from. 

❓Can I do anything for you at this moment?

This is a great opportunity to catch the mentors off guard or simply demonstrate that you’re not just there to take but to also give. A win-win relationship with your mentor is something to aim for. Maybe they would want to extend this relationship into a potential internship or a part-time assistant position or even more. Who knows where a coffee and a conversation with a mentor might lead you, right?

❓What is your biggest strength or weakness in the field?

The goal of this question is to discover whether your mentor has one really important quality – self-awareness. Asking them about their weak points might sound too intense, indeed. If you feel like they might get offended, good substitute questions to ask a mentor might be “What skills are you most proud of?” or “Did you learn any interesting skill that helped you run your company smoother in the last six months?”

❓How do you find inspiration?

This is one of the best questions to ask a mentor because it gives you an opportunity to learn more about their way of thinking and values. It also gives you a chance to picture yourself in their position years from now. It might also provide you with a different perspective on things and you might end up changing your way of thinking for the better. 

❓If more questions come up to mind, can I follow up with you?

If you are looking for questions to ask a mentor at the end of the meeting, this is the one you should go for. The question is especially good for leaving the first meeting with your mentor as it promises a future encounter. You are also saying that you will only reach out to them if you have a specific question or a relevant issue you need help with. Most mentors will definitely agree to that. 

❓Ask yourself, “What did I learn from the meeting?” 

When you’re back home, rewind the meeting in your head or go back to your notes if you took some and think about the things you learned. How can you apply the knowledge you obtained from your mentor? Do you wish to be in his/her place one day? 

Having a meeting with your mentor and asking questions

What you have to remember from this article is the following:

  • Preparation is a must before you meet with your mentor.
  • Have realistic expectations about the relationship.
  • Their time is precious. Make the most of it by asking straightforward questions related to what you’re struggling with.
  • Prepare a good set of questions to ask your mentor. 
  • Don’t forget to end the meeting with a promise for a follow-up if you have more questions.
  • Send a follow-up email after the meeting, expressing gratitude for their advice and words of wisdom. 

Meeting with your mentor can skyrocket your career. If you manage to handle the meeting well and find the right questions to ask a mentor, you will end up with an impressed mentor ready to vouch for you and further help you progress with your career goals. Remember to demonstrate leadership and run the meeting as efficient as you can. Be in charge of the content and showcase your strong communication skills not just at the beginning of the meeting but throughout the entire time. 

Good luck!

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Hi, everyone! I'm a passionate content writer with keen interest in social media, technology, innovation and business solutions. I am part of the team of Momibt - a revolutionary meeting management software designed to help businesses boost the productivity and efficiency of their meetings! Cheers!

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