Scaling Mentorship – Scott Hanselman

Dev Tips


You may have had a mentor in the past. Often these are more senior/elder people who are further along in their career. The presumption usually is that if they are “ahead” of you that they likely have something profound to offer you in the areas of advice or strategy.

This is a classic mentor/mentee situation and while I think it has value, it has a few problems that are worth pointing out. Does it scale? Is a senior person the right mentor for you? Is just one mentor the right number? Does that person’s time support mentoring you?

I’ve been blessed to have several mentors over the years and I’ve been fortunate to be a mentor myself. But there’s only so much time in the day. Even if I could truly mentor 4 people a week, and meet with them a few times a month, that could fill up many days. Plus, I have to ask my self – am I giving them what they need? Personal advice? Career advice? Technical advice? Getting promoted advice? Life advice?

Create a Board of Directors for Your Life

I’ve been experimenting with a few other models for mentorship. Five years ago I set up a Board of Directors for my life. You can learn more at

Companies have mission statements and a Board of Directors. Your life is pretty important. Why not create a Life Board of Directors to help you through it? Pick 2 to 5 of your friends. Not necessarily your closest friends, but friends that are close enough where you can really confide but not so close that they can’t see the big picture. Email them one a month, once a quarter or “once a crisis.” Ask them for advice, lean on them, trust them and help them as well.

Assemble “Team You” and use your team to brainstorm directions and implementations of big decisions like moving to New York, or changing your business’s direction, starting a new venture, or getting fit.

Use your personal Board of Directors as one of the compasses in your life. You’ve got family, friends, perhaps faith, hobbies, values, etc. Add your Team to this list of personal compasses.

It might sound like a silly mind game, but that’s common with many hacks. Hacks feel insignificant but can have huge effects. The trick is to remember that it is a hack – you’re hacking yourself. The idea of life’s board of directors is a relationship hack meant to remind you in difficult times that you can agree on something fundamental and you have a team to support you in your endeavors. Set a direction and head in that direction with the confidence you’ve got a supportive group behind you.

Go assemble your Life’s Board today.

Host Mentorship Meals

Over the last several months I’ve been quietly hosting “Dinner for people on the come up.” These are dinners where everything is FrieNDA and we talk frankly about our jobs, our levels, our work situations, and most importantly – we find new mentors and people with whom to brainstorm. It’s a mentorship multiplier. We encourage folks to pull from the pool of potential peer mentors.

Tonight we had one with almost 20 people. These were 20 mostly young people, many women and people of color who were all trying to find their way in tech. I have some life experiences to offer this group, but most of all what I can lend is my privilege. I can use my standing within the company and the industry to invite folks together and let them take over and mentor each other.

I host the mean, kick it off, sometimes invite guests to speak, and the attendees often break off into small groups, meet up separately and network. Peer mentorship is just as important as “elder/senior” mentorship.

It also helps mentor people in the the fullness of their personalities. Where I might help with speaking at conferences or technical issues, someone else can better speak to issues of harassment, or how to get a promotion, or how to be better seen and heard in meetings. I can also learn from younger people – and I do – every day.

The goal of mentorship isn’t to lecture and preach, it’s to guide and counsel, inspire and motivate. Most of all, to listen. Once you’ve truly heard your mentee, then you can help them think strategically and better plan their career, no matter what their challenges and strengths.

What do you recommend as positive ways to Scale Mentorship?

* Stock photo from The Jopwell Collection

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