How do you connect and ask your "personal board of directors" to help you?

Short answer: Nurture a loose connection into an ongoing relationship.

“Gib, will you be my mentor?” 

I get this question once a week. If pressed for a response, I say, “No.”

Nonetheless, I’ve mentored dozens of product leaders. These individuals found more effective ways to initiate the relationship with me.

For those who haven’t read my “Hacking Your Product Leader Career” essay, one of my hacks is to build a “personal board of directors.” I engage 5-10 individuals twice a year to compare notes on my job and career. (The board is symbolic —we don’t actually get together each quarter, and some don’t even know they are on my board.)

I perpetually re-build my board as my job changes, and I have two types of board members:

  1. Peers have similar roles and experience levels as I.

  2. Mentors have large networks, great judgment, and rare insight that helps me “see around corners” in my career.

How do I approach peers and mentors to join my personal board of directors?

Recruiting peers: Maintain relationships with past colleagues

This is the easy part.  I keep up with former colleagues via LinkedIn and reach out to a few key peers with very specific questions.  Today, my questions are, “What are your rates for online workshops?” Or, “Does it make sense to turn my Medium articles into a book?” I make it easy for peers to be helpful and they inevitably share more about their experiences with me.

Recruiting mentors: Nurture loose connections into real relationships

This is the hard part.

First, you’re better off building mentor relationships when things are going well, as it’s awkward to reach out when you sound desperate.

Here are the steps I navigate, although the order is rarely linear:

  1. Take advantage of loose connections. I reach out to potential mentors who are college or business school alumni, who live in my town, have kids on the same soccer team, or who love to ski, bike, or backpack. Some potential mentors are friends of friends.

  2. Ask a trusted reference for a two-sided introduction.  This means by the time I am introduced, the person has already agreed to help me.

  3. Be clear about what you seek.  Over the last five years, I have filled my board with fellow teachers, speakers, writers, and workshop hosts.  I have also compared notes about both advisor and board roles. Lately, I have been reaching out to enterprise software CEOs to learn more about product leadership in this context. It’s clear to each person why I want them on my board.

  4. Get to know the person via public resources.  I read the potential mentor’s writing, as well as press interviews and videos. If possible, I dissect their company’s quarterly earnings reports, or for startups, I spend lots of time with their product and website.

  5. Figure out how to create value for the mentor.  Sometimes it’s by referring candidates for roles they seek to fill. Often I give feedback on their talks, writing, or product.

  6. Pass their “tests.” Potential mentors are time-starved, so they subtly test your patience and persistence. I usually send 3-5 emails before I get a response. A typical response: “Set up a meeting in two months.” This is a test to see if I can navigate their calendar.

  7. Nurture the relationship. Once I engage the person, I do tiny updates on my progress or a longer update when I navigate critical career decisions. The point is to reinforce that I value this person’s judgment. I am also good about follow-up, reinforcing how their insight changed my thinking.

  8. Discover what type of communication works best.  Some folks like asynchronous communication (email), others like texting, while others appreciate Zoom meetings or a COVID-friendly “walk and talk.”    

  9. Be helpful. Some of my mentors have gotten back to me immediately.  One CFO responded instantly, explaining, “You may not remember, but you helped my son to find his first job.” There are many instances where the mentor felt like I had already done something helpful for him/her. You can’t plan for this, but it’s good to be generally helpful with as many folks as you have time for.

Everybody has an informal “operating manual.” Over time, you can learn how to develop a real relationship with any potential mentor.  (Reid Hoffman articulates his operating manual here.) The key to creating mentor relationships is recognizing they are human — don’t put them on a pedestal — and to find the best way to approach/nurture the relationship over time.

My operating manual

Here’s the type of help I seek, along with how to best communicate with me during a pandemic: 

Help I need:

  • Complete my surveys at the end of every one of my talks and articles. You can submit your name at the end, and I notice who it is!

  • Help me stay in touch/stay relevant. (An example: “Gib, don’t use “www”-- it makes you look old!”)

  • Find other ways to give me feedback—highlight typos in my writing, etc.

  • Help me connect and recruit Black/Latinx/Women product leaders for upcoming ProductLeaderSummit events or as panelists on my workshops/exec events.

  • Help me host free events for large, worldwide audiences.

  • Be an online helper, managing Zoom events, or moderating Zoom breakout room discussions.

  • Ask and upvote questions at talks and for this “Ask Gib” column. (You can ask and upvote questions here.)

  • Sign up for my “Friends of Gib” email newsletter to attend one of my test drive events and give me feedback.

How to communicate with me:

  • I value my flexibility a lot, so I don’t like to schedule too many meetings.

  • Sometimes I prefer a slow back and forth conversation via email.

  • Occasionally I ask folks if they want to talk “in the next hour or so.” (These ad hoc calls mean I am likely on a long drive, and I’m a little bored.)

  • My favorite meeting is on a chair lift. (I love to ski.)

With a little bit of time, you can figure out the operating manual for any potential mentor on your list. (Hunter Walk published his operating manual and so did Josh Elman.)

Build your personal board of directors

The best way to build your board is to start today— I have purposely made the first step easy:

  1. Create a list of potential peers and mentors.

  2. For the peers, send a quick email or LinkedIn message and let them know what you are up to and that you would like to compare notes.

  3. For the mentors, do your homework, so you can begin to test drive different approaches to create an initial connection, then build a relationship, over time.

  4. Carve out a little time, each month, to reach out to peers/mentors. Loosely update them on what you are up to on an ongoing basis.

My last note: You don’t get what you don’t ask for. You likely need to initiate ten “asks” to establish the one long-term mentor relationship that can make all the difference in your career.

I hope this answer was helpful.



Gibson Biddle

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