Top 10 Mentor Conversation Starters

There is no doubt that good mentors play a vital role in your career path. Most fortune 500 companies have formal mentor programs to develop mentorship relationships. However, mentorship is a scarce resource, and not everyone has access to it, which is why you need to make the most out of the opportunity when it presents itself. Asking engaging questions that provide value to you and to your potential mentor can start your relationship off on the right foot, and help you explore immediately if you’re a good fit.

One of the most prominent mistakes entrepreneurs, employees, or students make is to develop a one-sided me, me, my relationship, which makes things boring for your mentor. Bored mentors equal generic answers. Do the research about your potential mentor before you meet with them. As NF said, “You don’t have to know the album names or all my music, But at least try to find out who you in the room with”. It’s impressive to be able to relate to someone based on their interests right away, but what’s more impressive is that you actually cared enough to find a starting point for your relationship.

Here are some of the questions you should ask to kick-start the conversation and form a valuable relationship with your mentor:

“We’re here for a reason. I believe a bit of the reason is to throw little torches out to lead people through the dark.”

 – Whoopi Goldberg

1) What’s your mission statement, and how did you figure it out?

Asking a mentor’s mission statement is the most critical question. Since your mentors have already gone through the path of entrepreneurship, they can guide you through your shortcomings. Their mission statements will be the “little torch” to guide you through the dark.

“I strongly believe in rewarding people for their accomplishments, and, allowing them to make mistakes. That’s the best way to learn — in an environment safe enough to make mistakes.”

 — Niroop Srivatsa

2) What are the most memorable mistakes you have made?

Celebrating mistakes is as vital as celebrating victories. Asking your mentor about their mistakes and how they tackled them and made the best of them will teach you to take risks and overcome disappointment. You will learn to master improvisation and change your strategies to suit the situation.

3) What’s a day in the life of your mentor? AKA How do they spend their time?

Routine plays a massive role in shaping your life. It helps you in sticking to your plan on what goals you need to achieve while maintaining a successful lifestyle. However, many factors determine how productive you are and how you can optimize your time spent at work.

Asking your mentor about their routine and what they use to empower it can help you plan out yours. Being on a schedule can help you prioritize the critical tasks in your life and eliminate overwhelm around ones that don’t matter.

“It’s the things you fight for and struggle with before earning that have the greatest worth.”

― Sarah Dessen, Along for the Ride

4) What do you struggle with or excel at?

Realizing the strengths and struggles of your mentor will pave way for you to polish yours. It will provide inspiration, and help you understand the skill you have and the one you need to succeed.

“To seek truth requires one to ask the right questions.”

― Suzy Kassem, Rise and Salute the Sun: The Writings of Suzy Kassem

5) What questions did you ask in the beginning?

Perhaps you may have missed it in your list, or that question no longer holds relevance, but it is a great conversation started to ask your mentor about their initial journey. Knowing about the questions they asked, or wished they’d asked when they got started can help you create a master list of mentorship support conversation starters. This way, no matter where you are and who you’re with, you can ask encouraging and pertinent questions that draw out the very best information about who you’re with.

“Time is a running factor; once it goes, it cannot be reclaimed.”

― Sunday Adelaja

6) How did you learn to map your time? Or How did you learn to answer the “where will you be in 3-5 years” question?

Asking your mentors how they manage heavy schedules and keep track of their outcomes is the easiest way for you to create processes for yourself. Time is most valuable asset a person has today, so get help in learning how to plan your future 3-5 year goals, finding the right tools to maximize your time, and in being more direct in your conversations to cut the small talk and get to what matters.

7) What was the most significant obstacle in your working career?

Limitations are obstacles than can be overcome and turned into an opportunity. Entrepreneurs struggle with all kinds of restrictions, including new pandemic rules and societal demands we don’t even understand yet. Knowing what boundaries your mentor broke can inspire you to take (measured) risks as well. Being unafraid to take risks is the most important quality of an entrepreneur, and learning how your mentor jumped into cold water challenges head-first throughout their career can help you time your own cannonball into the deep end.

8) What was the biggest win of your working career? How did you get there?

The biggest win of a career is the most memorable and motivating experience you’ve got. It says a lot about a person to know what gets them excited. Ask your mentors about their greatest achievement and how they got there.

9) What are the top 3 things you consider when planning for the future? How do you find them?

A person evolves with time. Their goals and standards change. They learn from their mistakes and the time lost. Someone who has achieved success understands the importance of being able to pivot before the market demands you to.

Ask about the top 3 things to consider while planning your business launch or rebrand so you can understand why they care about what they care about. It will also help you make better decisions and could potentially help you relate to partners or clients later on.

10) What can I do better?

Mentors are your guides; they are there to help become better at your job and at life. Asking them the difficult questions like ‘How can I improve?’ and ‘What can I do better?’ will get you on the straight path. Criticism from your mentors is something to be celebrated, even if you do not appreciate it from others. This criticism, based on their expert evaluation of you, will give you tips that will help you succeed where they have succeeded. These people care enough about your future to tell you the truth about it. Listen.

Interested in setting up a mentorship program for Your business or association? Fiore3 Consulting can help.