You must be able to do the math
Welcome founders, VCs, leaders, entrepreneurs. I'm so glad you're here.
I really enjoyed hearing from so many of you after last week's issue around the value of enmeshing your identity with your company's. I read every reply to this email list, so please keep the feedback coming.
As a coach and experienced scale-up founder, I'm often asked for my advice on how to handle situations. With some exceptions, I mostly elect to respond to such questions with questions, or some other response that asks the client to work for the answer.
I recognize that this might be irritating if you just want the answer, but as you might suspect, there's a reason for it.
Such is the topic of this week's story.
“I know it’s all situational, but what would you do?” he asked me, again.
My first couple sessions working with the founder had been spent unpacking his goal to “level up his leadership to prepare for his Series B raise,” and we’d run into this dynamic before. He asked me what to do in a specific situation, and instead of telling him my opinion, I responded with another question. He was polite about it, but I could see him getting frustrated.
“Given your experience scaling companies, you should have some experience here that I can learn from.”
I sat for a moment, letting the urge to share my opinion rise up in me, crest, and subside. In fact, I had been in similar situations in the past and had a strong sense of the optimal route for him to take. But we’d been clear when we began our relationship that our shared commitment was to develop him as a leader, not simply give him a bunch of techniques to blindly execute.
“Are you a math guy?” I asked.
He nodded. “I majored in statistics at University.”
“Awesome,” I said. “I’m not. My degrees are in liberal arts. I did, however, take all the general math classes in college. I even did ok. They had me get one of those $150 calculators that can basically do anything for you, and I just figured out how to use the calculator. I got through basic math and even passed algebra. I just memorized which buttons did what, and in what order to press them, and got a B.”
He looked uncertain as to where I was going. “Calculus, though, that was a whole different beast. Once I got to calc, the calculator stopped helping. I knew the answers were in there, but try as I might, I couldn’t figure out what to even ask the calculator. What sort of function or sign or cosign or whatever the hell would help me answer the question.”
“So what happened?” he asked.
“I failed calc and studied creative writing.”
He laughed. “Fair enough. The math only gets harder after that.”
“It’s like that growing a startup, too.” He cocked his head in surprise. “You can go a long way by Googling for best practices on installing OKRs, or reading books on management or growth. You can find all sorts of tactics that have worked for others, in other contexts. Most won’t work in yours because your company is different, but you’ll find some that do work. Just glom this technique onto your company and reap the rewards. Like memorizing the keys on a graphing calculator, it’s a great technique for a while. Until your company grows in complexity to the point at which you’re not sure which off the shelf techniques to look for. Which buttons to push.”
“Yeah,” he said, picking up the thread. “And then you reach calculus and you’re screwed.”
“That was my experience,” I said. “Or you raise your series B. Same thing.”
–
Like a math major, your company will increase in complexity over time. In the early days, leadership may be as simple as finding the right best practices to integrate. But Frankensteining together a bunch of disjointed best practices is a great way to build a company you don’t understand and can’t manage.
Like getting a math degree, growing a company requires that you become a person that can generate their own answers, reliably and in complex and uncertain situations.
It’s a harder route, to be sure. But if you’ve made it to the point at which you’re hiring an executive coach, you’ve already proven that you can do hard things.
Things I read this week
One: How are you lying to yourself (Shane Mac via Twitter)
As professional decision makers, startup founders are particularly vulnerable to blind spots. The most insidious of those blind spots are the ones we create because we're too scared to look.
LINK >>
Two: Your management training sucks, here's how to fix (FirstRound)
Some of my most painful lessons scaling previous companies were learned because of poor management (yes, this started with me). This article is a gem that frames common management problems and their solutions in a startup context (which as a context is rarer than it ought to be).
LINK >>
Three: The use cases of Web3 (Yohei Nakajima via Twitter)
Web3 is no longer the free for all it was six months ago, but that's a good thing. Here's a measured examination of the long term use case for the technology, for those still curious and unconvinced.
LINK >>
Four: Termination Shock (Neal Stephenson)
Neal Stephenson is one of my favorite near-term sci-fi novelists working today, and his latest, about, loosely, climate change and global politics, is really really good. I won't spoil it but there's this real thing called the "Line of actual control" that is an amazing setting for a story.
LINK >>
Five: Remote, Hybrid or In-Person (AVC)
A useful birds-eye perspective on how some fast growing companies are balancing the individual happiness of remote work with the team happiness of in-person, without mandating one way or the other. Useful data for those making similar calls.
Want to dive deeper?
If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.
Here are a few of my favorites:
Executive Coaching for Entrepreneurs
There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.
I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency supporting founders to rapidly scale themselves as leaders, so they can thrive professionally and personally as their company changes the world. Leveraging 15-years as a founder/CEO, along with deep training in mindfulness, psychology, Neurolinguistic Programming, psychedelic integration and more, I have helped leaders from some of the fastest growing companies and VC funds in the world design a more conscious life and make key changes to improve their performance and satisfaction.
I coach leaders how I want to be coached:
Focused on the person, not the role.
Focused on results, without the fluff.
To learn more about working with me, click here.