Finding a Mentor: 5 Questions to Ask

I was working in my home office when our family’s former babysitter, Lauren, texted. She was in her junior year of undergraduate classes, studying Elementary Education, and she was requesting to meet with me next time she came home. Lauren had become part of our family in the time we’d known her and I was happy to oblige.

When Lauren was in town next, we met for lunch and we caught up on all she’d been doing while at school. She explained that while she had been dealing with the stresses of her coursework and leadership responsibilities at her university, she’d started a jewelry business. At first the business was just created as an avenue to relieve stress, but it had started doing quite well; she was now learning how to balance the responsibilities of being a full-time student and a part-time entrepreneur.

During our time together, Lauren said to me, “I know what you’ve been able to do with your business and I highly respect you. I was wondering if you’d consider being my mentor.” Before she could finish her request, I excitedly agreed and asked her what that relationship would look like. We carved out a plan to meet when she was in town and that I’d be available for any questions, should the need arise. I was honored to know she thought so highly of me and would ask me to help her navigate her path.   

Importance of Mentoring:

Although mentorship wasn’t ingrained in previous generations, it is a key factor in the advancement of women in leadership ranks. In 2012, LinkedIn conducted a survey which 52% of female respondents reported they never had a mentor because they hadn’t encountered anyone they felt appropriate. Unfortunately, my own research has affirmed the finding that all too often women don’t support other women.

The most memorable conversation of my research came when I was speaking to a woman who was a hospital CEO. She’d come from a nursing background and told me how difficult her career journey had been, stating the cutthroat environment of hospitals was almost too much to handle at times. In our discussion, I asked her, “can you tell me about any of your female mentors?” to which she replied, “Mentors?! I didn’t have mentors. I had TORMENTORS”!

I firmly believe that women are going to have to begin supporting one another if we are to ever make advancements in closing the workplace gender gap—in both pay and leadership. One of the best ways to show that support is by engaging in a mentorship relationship. However, because not just anybody with a pulse will do, there are specific questions that should be asked to see if the person you’re considering to be your mentor is a right fit. When finding a mentor here are five questions to ask to help you determine if the person is a match.

Finding a Mentor: 5 Questions to Ask

1. What has been your biggest set-back or learning opportunity and how did you navigate through it?

I don’t care how successful someone is, they’ve had to have experienced some level of setback or failure to be able to relate to you. Let’s be real, if someone hasn’t eaten dirt at some point in their career climb, how honest are they being, really? We’ve all experienced times of disappointment, and those have been the times where we’ve grown, as leaders and as human beings. You want to know what your potential mentor has experienced and how they dealt with their setback. By asking this question, you’re interested in how they would advise you to handle the challenges your career will inevitably throw your way.

Secondly, you’re not looking for perfection in a mentor—you’re looking for honesty. You’re looking for someone who can be compassionate, understanding, and someone who will also tell you the hard stuff even when you don’t want to hear it. If they won’t tell you what they’ve been through then how can you be expected to open up and confide in them when times get tough? Mentorship is a mutual relationship where you should have trust and confidentiality (and honor their private information, as well).    

2. What are your personal core values?

Personal core values are similar to business core values, but they define what is most important to the person. Personal core values are a set of 3-5 qualities that the person holds as highly esteemed virtues for themselves. These values serve to guide their choices, behaviors, and actions (everyone has them and it would be beneficial to define yours, too, before you ask this).

The importance of asking this question, though, is twofold. First, asking them to define their core values will help you determine if there is alignment between what you hold in high regard and what your potential mentor deems important. If, for example, you value integrity and your potential mentor values success at all cost, there may or may not be alignment between the two of you personally. They may be able to help you succeed in your business goals, but will you be happy if the way they suggest moving forward violates your integrity?

The second aspect of this question, however, is to consider if there is alignment between what the person deems as their core value and how they behave. For instance, if a person states that family is one of their core values but you see behaviors that demonstrate otherwise, you would want to weigh that in your consideration. It goes back to the old adage “actions speak louder than words.”

3. How have you supported other women on their career journeys? Have you ever experienced a female tormentor?

You want a cheerleader, advocate, coach, and friend in your corner as a mentor; the last thing you want is someone you confide in to betray your confidentiality and trust. You want a mentor who is confident enough in their own skin to be supportive of your journey and who isn’t jealous, or worse, someone who would sabotage your advancement.

When asking how your potential mentor has supported other women on their journeys, ask them for stories of how they’ve been able to help others, or if there were times they showed support for someone else even though it may have meant they lost the opportunity as a result.

Also, ask them to share any stories where they were on the receiving end of being tormented. Find out how they handled the situation and what they learned from it. Knowing how people deal with interpersonal difficulties shows a lot about how they’ll advise you to handle similar situations.

4. What one thing do you still struggle with?

It’s important for your mentor to be vulnerable with you. After all, they’re in your life to help show you how to be your best and that will mean you will be opening up and sharing what you’re struggling with to them. We all struggle with something and to ask them to share their inner struggles is not out of line.

For your potential mentor to open up and let you in on their personal journey will shed light on their humanness. It will show you that no matter what stage of life we’re in, no one has everything perfectly together—despite outward appearance. You want someone to be able to be real, raw, and genuine with you because that’s what you’re going to be with them.

5. How can I support you?

Surprisingly, a positive mentoring relationship shouldn’t be solely focused on you and your needs; it should be a two-way street. If you’re searching for the best mentor for you, find someone whom you can benefit by being in their life as well. There may be specific skills, connections, or ideas you have that would be a perfect way to make their life a little easier.

If your mentor gives you suggestions on ways to support them, ensure that you complete their request with excellence. For example, if they communicate that they need help with a project then show up 10 minutes early with their favorite drink in hand and a smile on your face. Above all, be a source of joy in their life. 

When you have the right connection, mentoring relationships create a unique, incredibly valuable bond. Your mentor should be knowledgeable and have an understanding of how to uncover potential and foster growth in you and your career. The right mentor will help you navigate turns by helping you look for blind spots and pitfalls you may otherwise not even know exist. Your potential mentor should also assist you in developing strong leadership skills as you begin to take on more responsibility.

Strong mentors can be advantageous at any career stage, but especially helpful to those wanting to advance into leadership roles. But finding the perfect mentor for you can be a bit tricky though, because not just anyone will do. Hopefully when finding a mentor, having these five questions to ask will help you identify someone who will be the best match for your personality as well as business goals.