Over the last few weeks, I have been talking to a number of companies while looking for my next role. This has led me to think more deeply about how to navigate this and make decisions.
There are of course many variables to look at, from the personal, professional and financial standpoints. I definitely don’t pretend to give a glib, one-size-fits-all framework for this. But I have come to believe there are three key factors highly correlated with good places to work for in the long run.
The Changeability Factor
The best software is malleable and easy to extend or modify. Codebases and architectures that are not designed for change tend to ossify. The same is true with people. The best founders and leaders tend to have strong opinions, weakly held. They are able to fundamentally change their mind. And the more they know, the more they realize what they don’t know.
This is critical because each stage of a startup’s lifecycle requires constant self-reinvention, and often a totally different toolbox and mindset. Leaders who think they have arrived, that they’re the experts while everybody else doesn’t get it, are exponentially more likely to fail — and, tragically, don’t even realize it. I try to steer clear from these folks by inquiring, for example, into how they dealt with challenges in the past, what they have learned, and what they wished they were better at.
The “Next-Next” Factor
In the VC world, raising the next funding round is about financing what needs to be done to get to the next next funding round. That’s how many investors and founders look at it — what will you do with this money now, in order to get to the next raise?
Similarly, when looking for my next company, I find it helpful to think in terms of my “next-next” company: what will I wish to have in my resumé then that will make me learn and become more knowledgeable and interesting? This can be exposure to some interesting or emerging technology, working on an important but yet unsolved business problem, or simply a company with great reputation. YMMV.
The Gut Feeling Factor
Gut feeling gets a bad rep when it’s used as a basis for knee-jerk reactions. But reasoning about whether a company is a fit for me should not be that. Instead, I try to assess how I feel about it as the days pass: am I getting more excited about it as time goes by? Or less? Am I grasping for reasons to continue? Or just can’t wait for the next step? If your excitement doesn’t grow, the odds are this will not be a good place to join. Better look elsewhere.
It’s important to remember that it’s not only about me, or only about the company. It really is about the fit between the two. No use trying to fit a square peg in a round hole. Many great people are incompatible with many great companies, and that’s OK.
At the end of the day, hiring is a game of probabilities because you (and the company) can only preview so much. Avoid analysis paralysis. There will always be a leap of faith. And that’s also OK.
What about you? How do you think about these decisions yourself? Let me know in the comments! 👇
3 Articles
✍️ How to Run Engineering Team Meetings (and not waste anyone’s time)
There's a reason why meetings get such a bad rep: they're too often thoughtlessly scheduled and run. Catherine Miller, VP Engineering at Flatiron Health, gives some solid advice here on getting back to basics and making them suck less.
✍️ How I Survived Insane Hypergrowth at Airbnb
Being successful in these fast growing startups really is about staying as much in control of yourself as possible, bringing out your empathy for others. In that sense, these 5 lessons from Jonathan Golden's time at Airbnb are... golden (put totally intended).
✍️ Persistent Models vs. Point-In-Time Goals
Too often I've seen companies trying to implement OKRs in a vacuum. Without clear understanding of what the long-term company strategy is, teams can hardly be expected to do a good job in coming up with their shorter-term objectives. That's exactly the point made in this post by John Cutler.
2 Videos
📺 Most Leaders Don't Even Know the Game They're In
Simon Sinek's talks inspire me without fail and this one is no exception. I think that's because I completely share his perspective on the responsibilities of leadership. Here he makes the point that leadership hinges on empathy and perspective. And in his own words, "our job is not to be in charge, but to take care of those in our charge."
📺 Kelsey Hightower fireside chat at DevRelCon San Francisco
It's easy to get lost in the tech, but we should never forget that technology exists to enable humans to do good things. Kelsey Hightower is well known for being a Kubernetes expert, but if that's all you know about him, I strongly recommend this video. You may come out with an even better appreciation for empathy and for the power of learning.
1 Book 📚
When I uprooted my life and moved to Berlin in the early hours of 2015, I was alone, lugging one big, fat suitcase and having no idea what I was getting into. In hindsight, I feel blessed for all I got, but I won’t say it’s been an easy journey. Those first few months, adjusting to a much broader new reality, were particularly tough.
Coming to grips with my challenges was largely done over long walks listening to podcasts and thinking. It was thanks to the Tim Ferriss Show, and guests like Ryan Holiday and Naval Ravikant that I first discovered Stoicism. This was a turning point in my life.
Last year, a product manager I worked with was burying himself deep in the hole of overworking and under the weight of perceived expectations. Through 1:1s, breakfasts and lunches, I did my best to help him gain perspective, and slowly work through the challenges. In doing that, I turned to the same practical philosophy that I so often used as a tool to help myself — Stoicism.
A few days ago, after a few months of not seeing each other, we reconnected for a nice breakfast. It was fantastic to see him much happier, sporting his radiant smile, telling me how well he’s doing at work, and crediting Stoicism for much of this progress. As I was preparing to write this text, I pulled my copy of this week’s book from the shelf, flipped the cover open and noticed this forgotten post-it from when I lent it to him:
We all have challenges. Often, these are rooted in very old problems that humans have been grappling with for centuries. Someone wise once said that old problems have old solutions — and that the best books are old books that withstood the test of time.
Having been released in 2014, Ryan Holiday’s The Obstacle Is The Way is not exactly an old book, but the heart of it dates back to the 3rd century BC in Greece. Think of it as a modern and accessible introduction to Stoicism, illuminating the application of its principles through a number of historical portraits.
The writing is simple and fluid. The stories are inspirational and lend themselves to multiple reads. At its core, Stoicism really is about acceptance of what is, and an extreme ownership of our role in it. The Obstacle Is The Way is hence divided in three main parts:
Perception: Our attitude towards the problem
Action: Breaking problems down and turning them into opportunities
Will: Cultivating perseverance that can overcome difficulty
In other words:
See things for what they are.
Do what we can.
Endure and bear what we must.
Philosophy has a reputation of being impenetrable and impractical. But Stoicism is the most practical thing you can imagine.
If all of the above resonated with you, it’s very likely you’ll thoroughly enjoy this book. And, who knows, maybe you even find in it some keys to help you unlock a challenge you’re going through.
🙌🏽 Thank you for reading! Enjoyed this week’s edition? Have feedback on how I can make this more valuable to you? I’d love to hear it — my DMs are open on Twitter or just write me a comment below.
✍️ I write some more about tech and org stuff over at The Evolutionary Manager.
👉 You can also follow me on Twitter @prla