I recently came across this tweet by Scott Belsky and it got me thinking about some things.
The way I see it, at the core of this is a skewed perception of senior people. That they’re somehow different, carrying a certain aura, the stakes of talking to them higher. Part cultural, part upbringing (or a mix of both), this can be deeply ingrained in our psyche and conditions our actions and perceptions.
Let me tell you a quick story.
Within the span of 4 years, I happened to go from a mid-level backend developer role to leading a 50-strong Engineering org in a Series C startup. Through the different stages — from figuring out buggy payment system integrations, to wading through thorny organizational issues inside a senior management team — here’s the single most important thing I learned:
Everyone is trying to figure it out. Everyone puts their pants on one leg at a time.
This may sound obvious. But I don’t think that, in general, we act like it is. I remember in one of my previous companies flying to NYC for the first time, and finding myself in meetings with senior management. Half of the time I was trying not to choke on my anxiety, the other half trying not to appear stupid.
Once I became part of a senior management team myself, it was like a broken spell. No matter how high up in the hierarchy you go, there’s no supermen or superwomen. Sure, there’s more veneer and keeping appearances, but it’s all messy. Everyone is trying to keep it together. This building companies thing is hard and it gets harder as you go up the ladder. It doesn’t matter if you came from Twitter, Instagram, Facebook, or the mom-and-pop store around the corner. Still human, still flesh and bone, one brain, two hands.
I’m not thinking and writing about this only for the pep talk. It’s actually because I find this “deference to power” both unnecessary and dangerous to business success. It’s a competitive disadvantage. After all, what’s the point of hiring a ton of talented people if the environment is such that only a handful of HIPPOs get to call the shots? Sounds like a terrible waste to me.
Resolution can’t be one-sided. Leaders have the responsibility of creating an environment where psychological safety actually exists. Having a “flat org” is not about shallow HR org charts that end up in a gigantic mess of ambiguity. Instead, it’s about how we all relate to each other, daily, regardless of seniority, rank, experience or job title. If the junior frontend developer doesn’t feel heard by senior folks, or not even comfortable enough to voice their thoughts, something’s already amiss and won’t sort itself out.
The reality is that all good leaders not only welcome this input, they need it. They understand that it’s impossible to have all the answers and that only by bringing their teams along can the best decisions be found and made. As a VP Engineering, I can tell you I prized nothing more than those engineers who would speak up and contribute. I can also tell you I had to learn that titles can intimidate folks, and that my words tend to carry more weight than I think. It’s crazy to me, but it’s something I need to constantly keep in mind.
So, remember: everyone puts their pants on one leg at a time. Act accordingly, no matter which side of the table you happen to be on.
3 Articles
✍️ To lead, you have to follow.
Ever heard of the curse of expertise? Or the power paradox? All of these are huge leadership pitfalls, and we ignore them at our own peril. This blog post by the always insightful Will Larson shares a hard-earned lesson that may sound as counter-intuitive as it is critical to great leadership.
✍️ What does a VP of Engineering do?
Dan DeMeyere gives an excellent bird's eye view of what a VP Engineering must obsess about: leveraging their time, generating as much cascading context as possible for them, while keeping them loosely coupled yet highly aligned. This advice would have come in handy to me a couple of years ago.
✍️ Becoming a Magician
We often get stuck on local optima and end up missing the game changer. This applies to business and product development, and just as much to personal growth. I can't figure out who wrote this piece, but it's a beautiful take from the perspective of... bodypainting, of all things.
2 Videos
📺 How Etsy Grew their Number of Female Engineers by 500% in One Year
Increase the number of women engineers falls into that category of “everybody says they want to do it, but few actually do it”. In fairness, it is hard. I've done it in my last organization with moderate success and a long way to go. In this short talk, Kellan Elliott-McCrea describes how Etsy did it quite successfully a few years ago. As it turns out, everyone can (and, frankly, should) take similar initiatives.
📺 Chamath Palihapitiya - how we put Facebook on the path to 1 billion users
If you know Chamath, you probably know he's one of the cheekiest guys in the Valley. He's also one of the most interesting to me. In this talk, he walks through how he led the original growth team at Facebook to achieve massive scale. The funny thing is... it's nothing to do with "growth hacks" but rather some good old-fashioned product development -- enabling a framework and creating discipline. Simple, but not easy.
1 Book 📚
Have you ever…
Felt like your career might be approaching some sort of dead end?
Felt the urge to write or do something online — only to convince yourself that everything has already been said and that you can’t possibly add anything original to the conversation?
Felt that your company isn’t doing anything for you and your personal growth?
I won’t judge. In fact, I can’t even if I wanted to, because I have gone through all of those myself.
If you are (or have been) on this boat, then Jeff Gothelf’s brand new book Forever Employable is probably a good investment of your time.
Under 100 pages, this is one of those I consider “all killer, no filler”. It’s full of tactical advice on how to develop yourself and your personal brand — whether you’re pursuing a solo career or just looking to improve your stance where you currently are. What was particularly refreshing to me was how candid, and vulnerable, Gothelf is in telling his own story, effectively squashing the myth of “overnight success”.
As with so many good books, while there’s nothing particularly groundbreaking about it, it’s the combination of solid truths enveloped in a consistent framework that makes it immensely relevant. The backbone of Forever Employable is actually the scientific method applied to career development: formulate your hypothesis, experiment, draw your conclusions and iterate (Gothelf is, after all, the “Lean UX guy” as he himself puts it). But the proper application of this simple framework forces you to think through a number of simple (but hard) questions about yourself and what you really want. That clarity is where real leaps start to form.
I’d be remiss if I didn’t quote one paragraph towards the very end of the book, which I believe imparts a critical message to temper everything that comes before it:
Remember: You’ll never look back wishing you had done just one more project, lost one more hour of sleep, or made one more euro or dollar. What you will look back wishing you had done was watch your daughter play one more game of football or your son catch one more fish, or look into the eyes of your significant other over a romantic dinner and glass of wine. The work will always be there — the time you spend with loved ones won’t.
It’s easy to get caught up in the thrill (or trap) of work. In doing so, we mistake it for our identity and end up all confused. I have been guilty of this myself many times, and it’s a constant threat.
With that caveat, Forever Employable is an excellent quick guide to help us believe and invest more in ourselves. It’s like kryptonite for inertia, and perhaps inspiration for you to make that move you have been working so hard at convincing yourself it’s not worth making.
🙌🏽 Thank you for reading! I hope you enjoyed it, and until next week.
👉 You can follow me on Twitter @prla