How to mentor right

Find a mentor

Do you have mentor envy? I always do when I hear about co-workers or friends talking about meeting their mentors for coffee or bouncing an idea off their mentors. Where are all these mentors and why don’t I have one anymore?

One of the greatest things to do for your own personal development is to find a mentor. This is fact. Having the guiding hand and, more importantly, ear of someone who has experienced things beyond you is one of the fastest and best ways to level up at life. I also think being a mentor is of great value to help grow and learn as a person as well. Finding a match is the hard part — it’s not just as easy as meeting someone you admire and want to learn from, there needs to be a common feeling of “for the greater good” to make it really work.

The clear focus of a mentor/mentee relationship is to pull in different thinking through different experiences. It’s always preferable as you problem solve to look at something from all angles and we tend to stick to what we know. It can be uncomfortable to extend beyond the box we live in and mentors have that ability. We are born into this world with a pair of mentors in our parents and perhaps siblings. We then gravitate to our chosen social structure based on the school you attend, your close family friends and then work or community connections. By the time we are of age where we would like to assert ourselves we’ve created our very own knowledge construct and it all depends on your upbringing. Your thinking could be expansive or contracted simply based on who your circle of influence is.

The unknown unknowns

This is where we can fall into a trap of unknowns. If you don’t venture out of your comfort zone you often miss the other side of the story. We spend so much time building our own view of things in business and life that when challenged about a different viewpoint or approach it is human nature to retreat to the stuff and places we already understand. Ignoring other options and sticking to your tight thinking is not growing. Think of this as the ignorant stage. I went through it as a 20-something year old entrepreneur trying to make the transition to a 20-something year old leader. Learning to see other peoples perspectives is a skill that a mentor smooths over. Discover the unknowns that a mentor has already figured out and you move very quickly from ignorant to accepting.

The known unknowns

Having a mentor is like taking the red pill and being exposed to options. Being contained in your own head with your own purview and decision making frameworks means you will make the same decisions each time even as you expect outcomes to be different. Being exposed to other thinking, other frameworks and other styles helps to identify the areas of improvements in your life and how you interact with those around you.

The known knowns

By working with a mentor you start to bring their approach and thinking into how your decisions get made. It may not alter the outcome but taking into consideration a different process means that you are looking at whatever you are trying to achieve from a different set of eyes. The key is to consider alternative approaches, to see things from more than one vantage point and to take the appropriate path for the challenge. A mentor is not a person that tells you what to do they simply help you light up the corners that you weren’t exploring so decisions aren’t made in the vacuum of your upbringing.

My mentor journey

I’ve tried a few avenues of mentorship. My first was more of a peer group of CEOs going through relatively the same challenges that I was going through at the time. This was a great way to understand multiple approaches and opinions of challenges — some were similar to mine, others were completely different but they all helped contribute to the way I thought things through. This peer group was a facilitated peer group and it was tremendously valuable as a way to start to find other perspectives.

I then set out to find a true mentor for 1:1 acceleration and it took some time to find the right one. There was a local CEO and community leader that I knew on the periphery who I thought would be able to help me on my journey. I was at a small breakfast roundtable and he was the speaker and his approach and demeanor was exactly what I thought I needed. He eventually did become my mentor and friend for 3 years as I learned the ropes of being a CEO of a growing software company in my twenties.

The approach he took before discussing being my mentor was elaborate. He interviewed me and did his research on me before accepting a meeting for coffee to really connect for the first time. He talked to my peers to understand who I was in order for him to feel comfortable about the relationship. It’s hard to simply pair people together and there be a bond. It takes both sides to completely commit to each other and that takes continuous effort to get right. You have to like each other, respect each other and have a completely open and honest relationship with each other and that cannot change throughout. Before we agreed to work with each other, my mentor handed me a code of conduct that laid out his rules for this partnership and that’s when I knew he was the right person for me at that time.

We worked together for 3 years and they were the toughest and most rewarding years I had experienced professionally. We worked through every imaginable challenge you could dream up and then some. HR challenges, hiring challenges, product challenges, motivational challenges, productivity challenges, investor challenges, banking challenges, economic challenges, partner challenges and even family challenges. His was a voice and guiding hand that helped when despair would have certainly taken hold and crushed me.

There was many a time when the company I was running was at a crossroads and during one of these instances his calmness and experience allowed me to make the right but hard decision to move forward. I had asked my mentor to sit with us during our yearly corporate offsite to observe and help decipher some of our challenges. After a long day of hard discussions there was little consensus among the leadership team on a direction and my frustration was at a peak.

My mentor, who had been with us the entire time taking notes but not saying anything, suggested we take a break. He then took me for a walk around the grounds of the Inn we were staying at. I’ll never forget the silence that seemed to envelop us as we walked.

He didn’t speak, I didn’t speak. We just walked.

I was frustrated at how the day had gone and he knew it. Everyone did. We just walked and eventually he prodded by asking what the core issue was at hand. He kept asking until I got to it. His was a guiding hand, helping me to see where the real problem was. He wasn’t there to solve it for me, he was helping me solve it for myself. To see it. And I did.

In a 15 minute walk at the end of a long frustrating day, my mentor helped me set the direction for my company by only being present and asking me the same question over and over — each in a different way — until the answer was right there. The team returned to our room, my demeanor was completely different and we agreed on the path forward because I was reminded of what we were trying to do.

This is the power of a mentor. Someone that understands you as a human, your eccentricities, your leadership style, your drive and your passion. A mentor is not a business arrangement, it is a partnership at the deepest of levels and that’s why it is so hard to find the right one that will make a difference.

It’s hard but, in the end, the greatest thing you can do for yourself.

Image by Jaroslav Šmahel from Pixabay