For CEOs

4 Easy Ways for Any CEO to Choose a Mentor

As a first-time CEO, you might be wondering about the right way to pair yourself with a mentor who can guide you in your business journey. People commingle the words mentor and coach and consultant - and that’s okay! But I thought it would be good to go back to basics and just share, generally, what the role of a mentor is and how to frame your thinking about choosing a mentor whether it’s for business or personal reasons.

At Bolster, I run Bolster Prime, a new programmatic mentoring program. We partner a “been there, done that” CEO or operator with a startup CEO, add foundational content and access to the Bolster Talent Marketplace to help startup CEOs scale themselves, their teams and their companies. The first part of the engagement includes a mentor matching process - finding the right Bolster Prime Mentor to partner with each startup CEO or Bolster Prime Client.

A mentor is a person who partners with you to share their experiences, hopes and dreams in order for you to benefit from them and grow as a result. It’s a bidirectional relationship - through mutual sharing, you both grow and learn from each other. My favorite part about a mentoring relationship is that you grow both wide and deep - and in unexpected ways.

Mentors are not typically someone who is chosen for you - there are suggestions and introductions that people can make to you but a mentoring relationship isn’t going to work out unless both mentor and mentee mutually agree that it’s a match. So, it can take time to find a mentor. In some cases, you may pick a mentor and it’s not intentional and transparent - it’s someone who you look up to, seek input and advice from and ascribe to their mission and ethos and grow as a result. I’ve had mentors and been a mentor with and for many who were unaware of the relationship - and that, too, is fine!

There are no hard and fast rules of mentoring and mentorship. I do like to think that there are some basic constructs that will set each party up for mutual success!

  1. Be open and honest - transparency is best. Even if it feels awkward, if you are engaging with someone in an unspoken mentor-mentee relationship, you are only getting half the value. If you know who you want your mentor to be, find some time to sit down and have a conversation with them to make sure that there is mutual interest. It’s good to set expectations and think about things like:

    • Will this be informal, where you set meetings and connections on an ad hoc basis?
    • Or will this be more structured, where you set a cadence of meetings?
    • Do you have specific issues that you need mentoring on?
    • Or, are you looking for general mentoring and want to figure out what the specific focus areas could be?

    You get the idea. It’s good to set the stage so that both mentor and mentee are able to get the most out of the relationship.

  2. Decide if you want to AMPLIFY your skills or FILL GAPS. It’s pretty much a given that you are looking to grow from a mentor relationship. There are many ways to do this - but I like to think that they all come from a place of either doubling down and amplifying a current superpower that you already have and growing vertically or finding someone who fills in knowledge gaps in deep and wide ways so that you are growing horizontally. When I started my first company I created an advisory board - and had 1:1 mentoring from each member. My advisory board included someone with a broad background as a startup CEO as well as people with deep vertical backgrounds. For me, I needed to learn how to grow wide and deep. There’s no right answer here - and you may find that you want both kinds of mentors - so that you can grow both horizontally and vertically.

  3. Mentoring is not coaching. Mentoring is the art of learning from someone else’s experience so that you can leverage that experience and have more time to spend on exploring new frontiers. Your mentor is likely to use words like “in my experience” and “this is how you do this,” so don’t expect them to help you on all of the tactical and behavioral changes you might be looking to make. You should start with any mentoring relationship by baselining where you are at - making sure that both you and your mentor understand the starting point - and create an action plan for where you want to get to. Coaching is much less directed and more helping you learn the signals and build the muscle to achieve a goal or overcome a fear or obstacle and is a little bit more like therapy - your coach will ask you more exploratory questions as you learn more about what you need to draw conclusions toward a desired outcome.

  4. Mentoring isn’t transactional - but it’s best when there is incentive alignment. In order for a mentoring relationship to not be a transaction, there needs to be mutual incentive alignment. A mentor will be most beneficial to you when there’s some benefit beyond the mutual act of engaging with each other. If it’s a personal mentor-mentee relationship, it would not be wrong for a mentor to share and pay for a meal with the mentee. In a business mentoring relationship, providing some form of payment that aligns the mentor with you will result in a much deeper, focused and intentional engagement. Or, if money is short, trading services, making introductions to your network, or using equity versus cash also work. I like to keep the concept of a balanced account, generally, when it comes to mentoring. Leading with #givefirst is great - giving without the expectation of what you might get in return - but with structured mentoring I like to make sure that there’s strong incentive alignment to drive the highest potential of outcomes and accountability. The very nature of mentoring tends to be very giving - most mentors are available as needed in between mentoring meetings and the best relationships are one where the engagement is continuous versus just at the times when you meet.

Like I said when I started … there’s no one way to be mentored. The best mentors are ones that give their time openly and through the act of sharing their experiences, also learn and grow from that same experience of sharing. I can’t think of a time when I didn’t grow from a mentoring session and it feels like mentoring is best when both mentor and mentee have the capacity to mutually learn and grow from each other. The act of sharing your experiences with someone and asking them to share theirs requires trust and vulnerability. I love when I walk away from a mentoring session with someone having learned a new concept, a different approach to a common problem or finding validation for something that I already had as an experience.

Not unlike friendships, mentorships have ebbs and flows and, over time, the relationship may no longer have the same impact. I’m still friends with almost all the people I have chosen as mentors in the past - but many of them are now friends as a result of my experience base changing as a result of their mentorship. I still consider them mentors - and I go back to tap that mentor brick from time to time. Being a mentor and being mentored is a lifelong skill - if you are truly seeking to grow you’ll find that you will have many mentoring relationships over time. When you find that you know as many of the answers that your mentor is offering to you - it’s probably time to seek out someone who can share more of the unknown than the known. A bittersweet moment but also a celebration of your growth and success.

-Jenny Lawton, March 28, 2022.