Build Your Own Mentor Council This Year

I was nine when Luke Skywalker meet Ben Kenobi. At 12, I stared as Luke trained with Yoda. I loved those movies but they gave me the wrong idea about mentors, how to work with them, and how they work on you.

The young, impressionable person full of potential meeting the older, wiser warrior to train in isolation is not actually how most mentorship works. Instead, we work with lots of people, learn from lots of people, and are influenced as much from how we receive wisdom as how teachers transmit it.

As I wrapped up my time at American Express and started thinking about what’s next, I reconnected with a wide range of people from my career. Building on those calls and an idea from Clear Thinking, I built a Mentor Council.

Here’s how I did it, and how you can too.

Step One: Mine Your LinkedIn Network.

My first step was to go through my LinkedIn network and identify the 85 folks who I've fallen out of touch with and still passed the airport test.

I only accept LinkedIn connections from people I have met in person and who I trust. But I’ve been working in software for thirty plus years (!), so I have over 2,200 connections. This step took several hours.

But revisiting my network was great. It was sweet to look over old colleagues’ progress, posts and photos. I pruned some connections but ended this stage with great feelings for the people I’ve worked with over the decades.

Step Two: Send a Personalized Email.

Do not spam your friends! Take at least a couple of minutes per email to customize a template. Some people I’d lost touch with still asked if this was a bot, but most realized that a personalized template was the only way to re-start relationships at scale.

Here’s the email template that most everyone got:

Subject: Advice for Matthew’s Next Steps?

Body:

Dear [first name],

[personal note and transition]

…I’m wrapping up 18 months at American Express, which began when they bought my third startup. I’ve now started, grown and sold media, SaaS and fintech companies.

Before I dive headfirst into another project, I would appreciate a conversation with you. You are one of my favorite collaborators over a ~30 year career. So I’d love to catch up, discuss the future, and talk through various opportunities.

For more background, here are my?LinkedIn?and?personal?webpages.

If you are open to it, please let me know some convenient times for a Zoom call or a meeting in the Boston area. For convenience,?you can pick a time on my calendar, or just let me know what’s best for you.

Thanks in advance for helping me think through next steps. I hope we have a chance to catch up soon.

Matthew

Step Three: Record Your Results.

You don’t actually have to do this step. Maybe I’m too results oriented. Still, I found it interesting to see how many people signed up for calls or wrote back with times to meet. Even better, I loved seeing how fast people responded. In general, the wealthiest people I know responded fastest.

Of the 85 emails sent, I scheduled 37 calls. Within eight hours of sending, I had already booked twenty of them. The timing of rest was very much distributed along a power curve. But, as you all know, signing up for a meeting does not mean that the person actually wants to meet. So I didn’t consider someone a candidate for my Mentor Council unless we actually had the meeting and it felt mutually enjoyable.

Does all this sound transactional? I think of it more as scalable. Once you’ve efficiently found out which of your old collaborators still want to talk with you, you can focus your attention on them without distraction.

Step Four: Have the Calls.

This is the most fun part. I took notes on every call. Some were thirty minutes long wedged into a mentor’s busy day. Some calls stretched over an hour and a half and across a dozen time zones. Once we got to this part, and both parties wanted to reconnect, catch up and talk, it was just pure pleasure.

Well, not exactly. Some friends had had difficult events, years, periods. One friend “did one startup too many” and went through a messy divorce. Several friends expressed anger and frustration with anti-semitism rearing its head again. Many had gone through tough professional times.

But all the calls were real. I had an outline for each call - walk the colleague through the things I knew about the next step in my career and the limits of my certainty - but I tried to let the conversation drive itself.

As with customer discovery or gathering 360 feedback, after ten calls, patterns start to emerge. After a month and roughly 35 calls, I was ready to send out my first Mentor Council email.

Step Five: Alert Your Mentors. Let them Opt-Out.

On December 15, I bcc’d everyone I had met with on an email like this:

Subject: You are a Mentor for me - if you want to be

Body:

Dear Matthew’s Mentor Council,

Your first question is probably something like “Um, what is this now?”

Let me explain - Over the last month you got an email from me, met with me for thirty minutes or more, and helped me think through my next career steps. Thank you for that.

I’ve always wanted to have mentors for my career and my life. Although I’ve had influencers, an amazing coach, and episodic guides, I’ve never had a group of mentors that I looked up to and measured my progress with.

So I’ve appointed you to my Mentor Council. If you don’t want to be on this board, I completely understand - just email me back with an “unsubscribe” or similar message and I will take zero offense. You’ve already helped me a ton.

If you do want to serve as a mentor for me, all you have to do is receive an email from me every three months. You don’t have to read the emails or do anything else. Of course, if you do read the email and something resonates, let’s discuss. But there’s no obligation for you to do anything.

With that context, I’ll dive into my very first Mentor Council Report:

Since leaving American Express on November 15 and moving into my new office at?Industrious in Harvard Square, I’ve been talking with some wonderful people (you all) and thinking through your feedback.

I started many of the conversations by expressing what I felt clear about:

1. I don’t want to retire. I want to do something else professionally.
2. I want to do something meaningful - something with impact.

We then launched into what opportunities could fit those criteria.

Thanks to you all, I’ve crossed some opportunities off the list already:

• [name], thanks for your impassioned description of the academic path and the opportunities in teaching Mindfulness and Entrepreneurship. After reflecting on what you said and where I’m at, I’m not ready to teach full time. I still want to test my ideas on the topic at scale and in more environments. Let’s continue the conversation around a way to test the waters on this idea.
• [names], it was fun to talk about buying a business. After contemplating that path, it’s just too much of a departure from my software startup career. The search process for finding a good company to buy seems long, difficult and too new. I’ve read many stories of entrepreneurs raising search funds, looking for years and then ultimately returning the remaining money to investors. I’m not up for that.
• [names], thanks for talking through the coaching path. I’ve realized that I’m just not ready to (in the words of my wife) “Step out of the spotlight” at the moment. Hopefully I will mature enough, relax enough, and learn enough over the next decade that I can do so someday.

The three categories of “What’s Next” I’m currently contemplating are:

1. Starting a new company from scratch
2. Joining an existing company that needs a CEO
3. Joining a seed-stage VC

Thanks to all of you for your thoughts on these options. I need to dig deeper into each of them over the next couple of months.

The other major theme I heard from many of you is “What are you even doing with these meetings? You need to?chill out.” You shared some scary stories about the physical and emotional toll that pushing too hard for too long can take.

So I’m going to take your advice. Starting this afternoon, I’ll be offline until January 8. From then through March I’ll be around but splitting my time between family, skiing, work-next-steps, and teaching a?meditation retreat.

Once again, if you don’t want to get quarterly updates from me, please just let me know. Either way, I appreciate your time, energy and care in speaking with me over the last month.

Thank you! I hope you all have a joyful holiday season and a great start to 2024.

Matthew

I got one opt-out from this email from a friend saying “Let’s just hang out every once in a while.” No problem! But now I’ve got a group of people I care for and respect whose support I need to live up to.

Conclusion: You Can Too

After our initial call, all my Mentor Council has to do is receive an email from me every three months. The magic (if I follow through) is in living and working in a way that I’ll have something interesting to report to them.

My Mentor Council is a forcing function helping me make the most of my limited time on earth. If any of them read my email, great. If one or two of them make a connection or get inspired, so much the better. But the magic is in knowing that there’s a group of people out there that I respect, and that I owe them an update.

After I first sent out the email above, a number of mentors encouraged me to share this approach with others. Thus this post. Whether or not you believe that we are the average of the five people we spend the most time with, there’s no doubt that “Our identities are formed by the values lent to us by the groups we call our own.”

So be mindful of the people you spend time with, seek advice from, and work with. Mine your network to resurface meaningful, motivational relationships.

It was deeply rewarding to reconnect with colleagues and friends at the end of last year. I believe it will also prove meaningful for 2024 and beyond. I hope this method or something like it will help you for many years to come.