Hard Thing #4: The 10x Mentor
"Our greatness has always come from people who expect nothing and take nothing for granted -- folks who work hard for what they have then reach back and help others after them." - Michelle Obama
“I want to be you when I grow up…” I said, clarity unexpectedly dawning on me (a few years ago, at an age at which I fully expected to have been “grown up”).
I was having coffee with a mentor of mine: the first female partner of a white shoe private equity firm who went on to launch a successful credit fund and then “retire” into becoming the most popular professor and a dean at one of the top business schools in the country.
She’s a badass, yes, but my realization didn’t come from wanting to be a power broker on Wall Street (I had already quit that profession!) nor my desire to get back to teaching1… it was a recognition of how grateful I was for the personal impact this woman had on me (and so many others) and my desire to be able to have that kind of profound impact on others.
With that realization over coffee, I’ve wrestled with the how behind it for several years…
The 10x (or 100x) Mentor
Silicon Valley likes to talk about the “10x Engineer.” These are exceptional developers who can do the work of 10 other average software engineers and are often credited with a startup’s success in those tenuous early days.
This concept applies to most things and it certainly applies to mentors. One of the most famous 10x Mentors was a guy named Bill Campbell who famously helped Steve Jobs, Larry / Sergei, Eric Schmidt, John Doerr, and many other tech titans build their empires - they even wrote a good book about him: Trillion Dollar Coach. What’s more, some of those people (e.g. Sheryl Sandberg) went on to become 10x Mentors themselves.
I had the opportunity to witness one of my 10x Mentors in action yesterday when I attended an event with MA Governor Maura Healy.2 My mentor was part of the retinue standing behind the Governor as she did her thing, thanking all the various people who helped with the initiative, a smattering of polite applause sounding between each name. But then Governor Healy mentioned my mentor’s name and instead of polite applause, the crowd got as close to rowdy as a group of stodgy Boston academics and businesspeople can get, a few “WOOO!”s even escaped, one from yours truly. While I have to admit feeling a passing twinge of jealousy — she’s MINE, all mine! — it was quickly replaced with a deepening admiration for the breadth of her impact. This woman has been the single most impactful person in my life not related to me by blood or marriage… and it turns out I’m not the only person for whom that is true!!
How is she able to scale that depth of impact? How on earth could she invest so much time in so many people that she changes their lives? I think I’ve finally figured it out (at least, partially).
Advocacy vs. Mentorship
A great mentor will give you advice, will help you figure out how the game is played, will be a sounding board or sparring partner for important decisions, will share their own vulnerabilities in an attempt to make you feel less insecure about yours. The woman I mentioned is an amazing mentor, a 10x Mentor.
We used to work together and when I was quite pregnant in the depth of a Boston winter, she would insist upon driving me to work whenever she was in town so I wouldn’t risk slipping on ice when I walked to the subway.3 During those car rides, we talked about the meaning of life and work, the ways to balance the two (can’t say we really solved that one, unfortunately…), we debated business strategies, she helped me prepare for difficult conversations, and she forced me to think deeply about what I cared about and why. Again, an amazing mentor and a lighthouse in any storm.
But several years later, I saw her real superpowers emerge. At this point, she had gone off to be a senior executive of a successful startup. I reached out to her for advice as I was thinking about leaving the world of private equity investing to go into an operational role. She could have given me a bunch of great advice about networking, good recruiting firms, how to tell my story or amp up my resume… she could have been a great mentor. And that would have been really valuable.
But she went about 10 steps further: she became an advocate. In that first conversation, she pulled up her mental Rolodex of every interesting company that she knew was building out their executive teams, listed them all, and asked me who I wanted to meet. When I accepted an offer for an introduction, she made it glowing, friendly, and the person on the other side was always up for the conversation. In that pivotal moment, she made three critical introductions: two of which turned into job offers (one of which became the next chapter of my career) and the third sparked a whole bevy of additional relationships and connections that I maintain to this day.
She used the most powerful assets at her disposal - her reputation and relationships - to help lift me up and open doors that had previously been in another room and shut tight.
In the moment, being an advocate costs something. Being a mentor takes some time, sure, but being an advocate means taking a stand, having a perspective, or even putting your reputation on the line to vouch for someone else. Being an advocate is what supercharges change. It’s the difference between just being appreciated and being impactful. And being an effective advocate also requires some power - we can scream into the void until we’re blue in the face, but it won’t accomplish anything unless we’ve given people a reason to listen (more on this in the last section) - we have to earn the right to be advocates.
I worry that we’ve slipped into a bit of a trap by over-emphasizing mentorship. When we tell leaders to be mentors, but don’t explain the importance of, or insist on, their advocacy, a real dark side can emerge. How do promotions happen? How are hiring decisions made? How do fundraises come together? Through a clear and unbiased checklist in which the best man won? No f’ing way. All these things (and many more) happen because someone in the room pounds the table and makes a compelling case to take action. Inertia is a powerful force and overcoming it requires active engagement. I can’t tell you the number of large financial institutions full of brilliant minds that are flummoxed because their amazing mentorship and DEI programs haven’t yielded any material changes to the promotion or retention rates of underrepresented groups… it’s because mentorship does not equal advocacy and advocacy by the people currently in power is what makes things happen. Mentorship might even be counterproductive if it creates a false sense of complacency or yields a “pass” on advocacy.
Bees vs. Aphids
Now there’s a flip side to this that’s less comfortable to talk about: earning advocacy (you may be thinking: doesn’t everyone deserve help?!). I’m not exactly sure what I did to earn the initial advocacy of the incredible human being I described above, but I do know that once I got it, I tried really hard not to screw it up!
I have the immense privilege of getting to work with lots of companies, leaders, and students in my advisory and teaching work. Through that lens, it’s easy to spot patterns in how they leverage the resources available to them. At some point, I’d love to do a larger study on this phenomenon and how well it tracks to broader success,4 but for now, I’ll describe the three categories I see:
The Optimizers (“Bees”): some people and companies know how to optimally leverage the skills and expertise around them and transform them into results. I call these folks “bees” because it evokes the way bees collect pollen, pollinating the many flowers around them in the process, and turn that pollen into honey. They’re fun to work with/for, they make people feel engaged and useful, they demonstrate every day that they can execute on what’s in front of them. Working with these types of people / companies makes you want to go out of your way to be helpful, it’s easy to be excited about their potential. They are exciting to work with and they are easy to invest in. It creates a flywheel of execution and help: these folks are not only better at getting things done, but they ALSO get more help because people want to help them. It might sound unfair (the rich getting richer and all that), but it’s human nature and I’ve generally found that’s a hard thing to change.
The Idlers (“Dragonflies”): some folks fly around looking pretty but not doing much of anything. Every now and then you see them, but they don’t really engage, drifting through life without optimizing the resources around them. There’s nothing wrong with these folks, per se, but eventually people start to wonder: “what am I doing here?” This type of behavior doesn’t inspire action or evangelism and these folks risk stagnation.
The Time Suckers (“Aphids”): While I’m sure no one intends this, some relationships feel energy sapping. These are the managers who use a lot of time on relatively low-impact work, checking all the boxes rather than focusing on results or outcomes: the Dilbert universe. Every email or meeting request you get induces a sudden onset of procrastination. Here’s the thing about aphids… if my time is not being used well, I assume that other resources are also not being used well…. That’s not always fair (maybe it’s just a bad day), but it’s something to watch!
Bees invite nurturing, aphids have you scrambling for the insecticide. There is nothing more rewarding than seeing someone take a small nugget of advice or an open crack in a door and make something magical out of it. Be a bee.
Unfortunately, I think we often give young people advice that encourages them to be more like aphids (or at best, dragonflies). We tell them “mentors are important, go find a mentor” but we don’t teach them how to earn mentorship and advocacy organically or what to do with those emerging relationships. We make them feel entitled to mentorship without teaching them how to be bees, how to make honey. Instead, too often, they think the task ends with “Would you be willing to have a mentorship chat with me?” and then fail make good use of that time, assuming the mentor will magically understand their needs and desires and make them come true. Perhaps the most effective mentoring we can do is to help more people become bees, to teach them how to turn on the flywheel of further advocacy…
Power and Privilege
I’ve long struggled with the concepts of fairness and privilege (I wrote a whole post about it!). It always felt selfish and self-centered to ask for things that I wanted, and certainly to advocate for or even desire the things that felt zero-sum (money, promotions, awards, etc. - if I was getting it, I always assumed it meant someone else wasn’t).
But this concept of advocacy has begun to serve as a counterweight. The reality is that great advocates are effective because they have power. They use that power to open doors, pound on tables, and drive change. Without power, advocates can’t open doors as effectively, aren’t listened to when they pound on tables, and drive change much more slowly than they’d like, if at all. Bill and Melinda Gates are a lot more effective at saving children through their leadership of massive philanthropic endeavors than clipboard-wielding Save The Children reps - they can throw the weight of their power around to move resources at scale and inspire others to action. It looks more like screaming into a void than pounding on a table if you’re not even in the room.
I think it looks something like this:
It’s easy to tap out too early (“I’ve made enough”), before you really have enough power to easily lift up the folks coming alongside or behind you, before you have the multiplicative impact you might desire. AND, it’s easy to tap out too late (see Chapter 3, “Addicted to Success” in From Strength to Strength), never stepping off the treadmill to look around and think about how you can build and share wisdom. What’s magical about that peak period is that helping other people becomes easy - a 5 minute email or phone call can save someone else weeks or months of time - THAT is leverage, it’s rewarding, and it’s a major cheat code on life! There is not a linear relationship between the amount of time and the amount of impact and reaching the point where impact » time is really fun.
As many of us enter our peak career stage, I hope we choose to be more than mentors, to be advocates who lift up the people around us, who are generous with our relationships and our superpowers. It sounds saccharine and trite, I know (I’m cringing a bit as I write it)… But the surprise and gratitude that results from a genuine act of support or kindness is a function of how rare those acts are, of how cynical many of us have become.
I hope we become the kind of people that a room can’t help but cheer for…not because of our own accomplishments, but because the ecosystems we have nurtured have come alive and are extending our impact far beyond our personal reach. Thank you to those people who set an example for us all, you know who you are.
P.S. I have been fortunate to have many people in my life that I consider mentors and advocates (and many more than are listed here). I thank you (in no particular order!):
YH: For demonstrating that it is possible to succeed while being authentic and for your tireless advocacy of me and so many others.
PM: For teaching me that even after all you’ve accomplished, even YOU still struggle with feelings of “enoughness.” AND for helping me figure out how to handle my first “real” salary negotiation in an authentic way even though asking for more money felt gross and selfish.
TG: For pounding the table to get me hired (I assume!) and being a wonderful mentor to me in the early years of my career, including sending me the best pregnancy guide ever (a tradition I’ve carried forward!).
JK: For opening countless doors and pushing me to build new muscles.
TB: For helping me listen to my heart, by pointing out that my voice “sounded different” when I was talking about something I was passionate about.
BC: For pounding the table to ensure I got maternity leave when HR kind of forgot to talk to me about it and I was too scared to ask for it myself.
KM: For all you have done to advocate for women and teach them how the game is played, myself included.
You have all inspired me to be a better version of myself and to pay your kindness forward. For that, I thank you so much.
Though I did and now help teach a class on failure at HBS - blog post on failure coming up soon!
…during which she announced a major investment into AI infrastructure in the state, go #teamMA!
Back in the days when Boston had ice in winter!
And then I’d like to figure out how to most quickly measure this so I could develop an investing strategy around it…. I have some ideas :)