Mentorship Matters

For so long they cheered you with the purity of a pre-teen at a Taylor Swift concert. They celebrated even your tiniest accomplishments. They wanted you to be successful. They sometimes even believed you were capable of things you yourself doubted. And then, at some point, it all stopped. The purity was replaced by jealousy, and the words of encouragement were shifted to lesser folks. We love seeing people do well … just as long as they don’t surpass our own status. And once they do, He really needs a measly compliment with a title like THAT?! Probably had to know somebody to get the job anyway. LOL to those who think he got there with “merit.” And don’t get me started on wealth inequality. Tell me what he actually does to earn 20x more than that earnest janitor. I’m not seeing it!

But of course the same human needs for acceptance and appreciation don’t disappear once one owns an ungodly # of VTI shares. So here I am cheering and celebrating you. Here I am thanking you for the past two months of working together, which were my favorite at xxxxxxxxx. You said something this summer about me “thinking too much of you,” and I’m convinced you were/are obviously incorrect. Aside from my parents, I truly don’t think there’s a single elder I’ve learned more from than you. Here’s a little list of learnings that may well read like a fanboy writing T Swift:

  1. You can’t do everything yourself. You are often not making the company better by doing people’s jobs for them. You are, in fact, feeding your own ego by grabbing accomplishment in areas that are simple (for you) instead of focusing on the hard stuff only you can do. What hollow “wins” are you accumulating as a diversion from the stuff you don’t want to do? A worthwhile question for all of life.
  2. If the users weren’t involved in the decision-making, they will often reject the solution. They may do this to the point of self-sabotage. They may do this in spite of you having built something incredible. Overcommunicate. People want to be in the know.
  3. Related to #2 is playing down your own intelligence to let others express the ideas you already hold. They will feel more ownership if it’s “their idea” as opposed to being told what to do.
  4. Try not being immediately identified as the thing you most like being identified as. If your identity is true – you like being seen as smart and you are indeed smart – it will be revealed in time. By getting there RIGHT NOW, you (a) close off the possibility of being other things and (b) pay less attention to your surroundings.
  5. Offer firmish suggestions with smiles and self-deprecation. Yes, go ahead and point out the absurdity of a meeting, a plan, a whatever, but make sure you cushion it with things like, “I know I’m probably being annoying.” This same concept of cushioning is similarly important when suggesting a go-forward plan. You may be quite confident in your own correctness, but speaking with the certainty of a prophet can lead to resentment (see #2). Then again, you also still kinda need to sound like a prophet, for most people require leading and will procrastinate if left to their own devices. Good luck!

I remember a meeting early in your tenure regarding xxxxxxxxx where you probably identified the crowd as strongly pro. You thought the product was lackluster. At the outset, you said, “Call me xxxxxxxxx.” After mentioning that you needed more evidence to justify a purchase, someone (xxxxxxxxx?) called you xxxxxxxxx. “Oh, so now I’m doctor that I’ve said something wrong.” This little line of levity prevented the meeting from spiraling into defensiveness and taciturnity.

As you are well aware, substantively integrating oneself with strangers is both challenging and vital to success. To ease the challenge, people will drop the substance part, nod their heads along with anything, be extra genial, take forever to decide (lest someone feels a tiny bit uncomfortable), admire their “well-liked” reputation, and call it all a “smooth integration.” But no. This is how a class of “leaders” who can’t lead festers. You, better than anyone I know, deftly pull off the high-wire act of quickly demonstrating that you are about getting things done while also not totally disrupting the preexisting order and engendering quiet disdain. The xxxxxxxxx team was filled with all sorts of people, and yet they all reached a similar conclusion: I love those meetings with xxxxxxxxx!

  1. Set the standard early that we aren’t going to waste time in meetings. Once the culture of 20-person meetings takes hold, good luck reversing it.
  2. You can say real things and be in a position of power. God, nobody trusts institutions anymore! It’s terrible! Where did all the trust go! Well, when failures are easier to find and highlight due to unprecedented transparency (thanks to the Internet and digitalization), the say-pretty-words-while-saying-absolutely-nothing-PR-thing rightfully loses effectiveness. Society probably isn’t failing any more than usual, and obtaining ideal outcomes remains as hard as ever, so the low-hanging-fruit is to simply stop treating audiences like children. Yes, there will always be bad faith and you’ll never please everyone and there are some things only insiders can know, but if you actually flex a bit and show you aren’t some empty suit who’s merely titled an “expert” as opposed to, you know, being an actual expert, trust will rise.
  3. Organizational dysfunction stems from people hiring others to do things and then never really probing if they are, in fact, doing those things well. Part of this is a lack of curiosity. Part of this is not wanting to look stupid interrogating something foreign. Part of this is a simple lack of time. While delegation is a must (see #1), blind handoffs won’t cut it; no matter how great your hiring practices, ongoing verification is necessary.
  4. People will tell you what they think you want to hear, so push for proofs, however tiny. “Oh yes, I got this.” Ask another question. Can they repeat what you just said? Can they correctly summarize the steps?

Lessons aside, these 2x weekly meetings have just been so damn enjoyable. Thanks for all the time and candor. I have confidence that if there is a way to right the xxxxxxxxx ship, you’ll be instrumental in finding it. Which is to say that as long as you remain in your current role, I won’t puke these xxxxxxxxx shares to buy another xxxxxxxxx.