An Unreasonable Investment is another excellent leadership essay by Michael Lopp. Here’s something to take with us into our jobs every day:
You want some free leadership advice? You build yourself by building… by helping others. The selfless act of helping humans will teach you more about being a credible leader than any book.
Your career is not your job. It’s the humans you help along the way.
Molly Graham has a fantastic essay on how to figure out if a job is the right fit for you. The post focuses on senior roles, but there are some great tips for everyone here:
What I look for, truly, is the intersection in the two sides of the equation: does what we NEED match what this person WANTS to do? As I said, most companies and most interviews focus more on the question: can this person do what we need? But if you’re trying to recruit the best talent in the world, it needs to start with them. Who are they? What do they love doing? What are their ambitions? How does their past shape what they want for their future? What are they insecure about? What do they want to prove? My interview style is really about mapping that.
I love JJ Skolnik’s essay Love + Work for Flaming Hydra (paywalled but well worth it—this newsletter is great). JJ used to work at Bandcamp and reflects on “loving your work” when it doesn’t love you back. And he has some wonderful reflections on the meaning of music too:
Underground music is vital because it is an experience that cannot be replicated in capitalist language. No matter how much one tries to distill it down to a matter of commodity exchange—there is nothing that can capture the joy of a bunch of freaks making the music they want to make and sharing that in community with one another. This is true no matter how much money is poured into it. Money isn’t what makes it grow.
This is another fantastic post on career development from Johnathan and Melissa Nightingale. This bit really resonated with me:
I want to feel like I’m making progress. And to feel like the various work experiences I’ve had are all building toward a thing. I want to be able to talk about work, not as a string of jobs I’ve done, but as a career.
We already know that actions > words but this is still really interesting research:
Daughters of dads who talked a good talk about gender equality—but who nevertheless didn’t do as much as their partners in terms of domestic labor—had lower career aspirations than daughters of dads who pulled their weight around the house.
This is a great hiring post on “reverse interviews”—or how to make interviews less one-sided and make sure you get the information you need to make a decision about a company. I like this question in particular:
Ask your direct manager for examples of promotions and attritions they have managed. Request stories about individuals they’ve managed in the past who have gone on to achieve significant success. Ask about the frequency of their meetings with direct reports, their perspective on their role in your work, their preferred communication styles, and their approach to staying informed. Also, clarify who makes which types of decisions.
I wholeheartedly endorse the RawSignal team’s take on performance reviews:
A great performance review is not an evaluation conversation, it’s an alignment conversation. It shouldn’t be a conversation about which things happened, it should be a conversation about which things matter. It’s an opportunity for you and your person to get onto the same page about where you’re seeing the work differently, because that is informative in terms of how the next year is going to feel.
I came across a couple of really helpful articles recently about how to start a new job well. 30 Tips for New Startup Employees is a long and super useful read—and not just relevant for startups:
Align yourself with the risks of the company. If you’re an engineer but the company is not acquiring customers fast enough, spend your time in marketing. Have range, and don’t try to be too narrow in your focus in the early days. Gain knowledge in a few different areas of the business so you can reduce the overall risks of the company.
Learn How The System Breaks is more relevant to technical roles, but I think “failure streams” can be expanded to other areas of the business as well:
Failure streams are a short circuit to understanding the system, because failures are where the system is interesting and nuanced. Failures are where the heart of complexity, entropy, and flux in the system are. Everything that doesn’t fail behaves like the architecture diagram. Failures show where the architecture isn’t working as intended. By focusing on failures, engineers can onboard quickly into the most important part of the system - the part with problems.
These are all great tips. The one I would add as most important for me personally is related to the concept of Chesterton’s fence:
In the matter of reforming things, as distinct from deforming them, there is one plain and simple principle; a principle which will probably be called a paradox. There exists in such a case a certain institution or law; let us say, for the sake of simplicity, a fence or gate erected across a road. The more modern type of reformer goes gaily up to it and says, ‘I don’t see the use of this; let us clear it away.’ To which the more intelligent type of reformer will do well to answer: ‘If you don’t see the use of it, I certainly won’t let you clear it away. Go away and think. Then, when you can come back and tell me that you do see the use of it, I may allow you to destroy it.’
Or to put it in terms of systems thinking:
Before you disturb the system in any way, watch how it behaves. If it’s a piece of music or a whitewater rapid or a fluctuation in a commodity price, study its beat. If it’s a social system, watch it work. Learn its history. Ask people who’ve been around a long time to tell you what has happened. If possible, find or make a time graph of actual data from the system. Peoples’ memories are not always reliable when it comes to timing.
When you join a new organization you’re probably going to see a lot of random “fences across roads.” Instead of saying “let’s tear this thing down,” first ask “why is this fence here?” There is always a reason, and it’s very likely that there is value in the reasoning. First understand, then make change.
Some good tips here from Kax Uson on How to receive feedback—especially when you don’t agree with it:
Validate the feedback with other people. There will be times when we don’t really trust the feedback we receive, or in some cases, the people who gave them to us. This is normal. When this happens, it’s worth cross-checking the feedback with the people we trust. I like to think of it as getting a 2nd opinion vs immediately dismissing the feedback or overthinking it.
This is great post by Will Larson on the difference between personal (and organizational) “brand” vs. “prestige”—and why focusing on building the latter is way more important for your career than the former.
First, this reminder:
The majority of successful executives I’ve worked with don’t write online. They won’t post on Twitter or Mastodon. They haven’t written a book. They don’t speak at conferences. In your engineering leadership career, you will at times be immersed in the message that you need to be creating content to be successful, but there’s abundant evidence to the contrary. You absolutely don’t have to do this sort of thing.
And then, this definition of what he means by “prestige”:
Prestige is the passive-awareness counterpart to brand. Rather than being what someone actively knows about you, it’s what someone can easily discover about you if they look for it. Many interviewers won’t know anything about me, but a few minutes of research will find my writing, conference talks, and work history.
I agree with this. Make sure that if someone Googles you, they find your site where you can tell your story and showcase your work.