As people were coming back from the holidays, I had the chance to catch up with two friends earlier this week on two different occasions. One who built a company hundreds strong. The other is someone who’s seen the rise and fall of civilization again and again.
The former told me, “The greatest litmus test of a leader is their ability to train another leader.”
The latter told me something they had learned from a successful founder. “I lift as I climb.”
Both equally as profound. But to take it one at a time…
To train another
I’ve mentioned on this blog before that A-players hire A-players. And that B-players hire C-players. C’s hire D-players. And so on. A-players can tolerate working with B’s, but not C’s and D’s. So at the end of the day, the A’s leave, and all you’re left with are B’s and below.
While that statement makes sense in broad strokes, the truth is from an investor’s perspective — hell, just an outsider’s perspective — no one knows if you’re an A-player or not at first glance. Or at least it’s really hard to tell. Maybe there are people who are smarter than me out there who can tell at a glance. At the end of the day, seeing others execute is a great way to tell, but that takes more than one meeting usually.
And sometimes the easiest way to see is in doing reference checks. Seeing who else is on the team that they hired and trained. Seeing who they hired in previous roles. And if those other folks they’ve trained have gone to do amazing things, that’s usually a good sign that the person in question knows what an A-player looks like. And if it’s consistent enough, knows how to mint stellar leaders.
I lift as I climb
One of the greatest red flags I often see are founders hiring experienced (often expensive and brand-name) executives, sales reps, and product managers super-early in the startup lifecycle. Especially before product market fit. And often the biggest expectation for these early hires is to do:
- What they themselves couldn’t do
- And/or what they themselves don’t want to do
Both happen to be cardinal sins at the early stage. Why does the above matter?
Because if you’ve never done the job yourself, specifically building/managing the product and getting to your first customers:
- You don’t know how to set realistic targets and benchmarks for that role
- Given how crucial early customer feedback is to the product and the company, you’ll miss out on key customer insights if you’re not in the trenches yourself.
The goal of the afore-mentioned early hires is to refine your playbook, not build the playbook from scratch. And if that doesn’t appeal to you as the founder, then you might not be ready to be one.
And this is the exact reason I love the line “I lift as I climb.” For every time you figure something out, an inflection point for the company, a key customer discovery/insight, a sales script that closes twice as well as the last one, your rising tide raises all boats. But you cannot lift if you don’t climb first.
In closing
For those of you tuning in from the video and audio universes, you know I’ve been thinking a lot about succession planning as of late. Largely motivated by my conversations with Ben from Next Legacy.
And Courtney from Recast.
So naturally, when I was catching up with both of my friends, their words found refuge in the questions I was seeking answers to.
And when all’s said and done, what I look for in a founder who’ll create a multi-generational company is the same in what I look for in an emerging manager who’s planning to build a multi-fund firm. And in a way, what a young professional might look at when betting their career on a startup.
Photo by Vincent Chin on Unsplash
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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.