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Cognition

Maximizing Mentorship

At an Owner Camp a few years back Wil Reynolds, founder of SEER Interactive, mentioned he collected a personal board of directors who provide advice and mentorship across a spectrum of areas of his life, personal, professional, etc. Inspired by that idea I’ve made it a priority to cultivate a similar professional mentorship network.

These advisors provide more value than they realize, and I rely on their insight and perspectives in a variety of ways. Cultivating this network wasn’t easy, but over time I’ve developed a few strategies that seem to work successfully.

Confidentiality is critical. These conversations happen in a “Tree of Trust.” If I’m going to share openly the confidentiality of what I share has to be defended fiercely.

A mentor can’t be someone I’m actively working with. I need that separation of church and state to ensure the conversations I’m having are uninfluenced by my day-to-day work life.

At the same time, I need to have a deeper personal connection with each of my mentors. If I’m going to willingly spend time with someone, even just a few hours a month on the phone, I need to genuinely like that person. Life is short, I need to fill it with people I enjoy spending time with.

Last, and perhaps most importantly, I’ve discovered that pacing the cadence of these conversations in different ways, and establishing different relationships and expectations with these mentors, makes engaging with a bigger group more manageable and valuable. Some conversations move faster, others slower. This provides valuable options and a welcome variety to these conversations.

Master and apprentice

The first wave of mentors I established were people who exemplify my potential career path ahead. This felt like a familiar, traditional mentorship model. It was easy to describe the value and expectations around these relationships to the people I approached, and we were up and running in short order.

These more traditional mentors are professionals who represent where I think my career could track over the next 5–10 years. These are folks I’ve worked with previously or gradually gotten to know through events and conferences. Talking with them is a little like talking with a potential future version of myself. They’re a little further down the road and have helpful visibility into the obstacles that litter the path ahead.

Meeting with these folks typically occurs quarterly, sometimes monthly, often over a 1-2 hour phone call. They have a familiarity with some of the details of my work, but a broader overall understanding. Their advice is less wed to specifics. Our conversations center around longer term career goals vs tactical advice.

A wartime consigliere

Next I opened a personal Slack channel and populated it with a handful of folks whose advice or support I tend to need more readily on-demand. It may be that I have a pressing concern and need instant insight or advice. It may be that I’m grappling with something and need an ear to bend or moral support. They’re more immediately available and respond readily.

I communicate with these folks roughly monthly, but intentionally less rigidly scheduled. The more frequent pace of our interaction allows for a deeper context threading from conversation to conversation. I can share something I’m struggling with, collect their advice, and later update them on how things turned out. In general it feels like this group is “always on,” and generally has my back.

Peer mentoring

I became aware of peer mentoring when two agency owners mentioned to me that they scheduled periodic check-ins with each other to provide ongoing support at a peer level. This felt like a more eye-to-eye approach than a typical mentoring relationship, and it felt more accountable and invested than the loosely structured support my Slack channel denizens provide.

This was easily the hardest piece to click into place because it truly takes two to tango while peer mentoring. You have to relate enough to one another for your advice to have meaning, but you have to be distinct enough to provide a unique perspective. You have to both perceive the value of the peer mentorship relationship, respect the structure and adhere to a schedule of some kind, and maybe most importantly, you have to really invest in this relationship.

I was fortunate enough to meet someone who was experiencing many of the same challenges and opportunities I was facing, who had a very different professional background, but many of the same personal interests, who seemed to have similar values to mine, and who was equally invested in the idea of peer mentoring. This was pure luck. I don’t have any advice on how to find folks who can meet these criteria, except to say keep your eyes and you mind open.

Our weekly check-ins have been a valuable resource. Like my traditional mentors, this relationship provides some direction into longer term goals because we’re focused on many of the same career questions. Like my Slack channel support group there is a frequency to the conversation that provides more opportunities for granular advice, or suggestions driven by deeper context. In general though this conversation is more comprehensive and personal.

Mentoring forward

It’s sometimes a challenge to stay on schedule or connected with the various mentorship channels I’ve developed. Sometimes a quarterly check-in gets pushed back, or time passes and I haven’t connected with one of the members of my Slack channel. The value they provide is incalculable though, so it’s an investment I work to protect and take seriously. Like any valuable relationship, you have to make time available to maintain it.

Logistical challenges aside, my goal is to invest deeper in mentorship over the next year, not reign it in. I’d like to try to add someone to my small group of traditional mentors who is completely outside my industry and professional swim lane. I’d like to identify a mentor whose home-life is as much of a model for me as my work mentors’ careers are models. I’d also like to focus on giving back more, both to those I’m already connected to, and to someone I feel I can genuinely help and mentor. In this way I hope to pay forward the time my mentors have so generously invested in me.

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