I’ve come up with a simple way to encapsulate the benefits of LLMs we refer to as AI: momentarily useful. To explain, let me first present my good use cases for LLMs. Then, I’ll contrast that with what they are disastrously bad at doing, and why “momentarily useful” explains the gap.
There are only two types of folks in business: Buyable or not. Founders often try to find the latter by emphasizing “mission-driven” cultures. Over the last decade, I’ve slowly realized my intuition has carved out a middle path between money and mission that defines how I hire.
I remember the moment I realized we were doomed. An executive demanding change based on their feelings never goes well for anyone.
A meditation on learning to let go without giving up, decades in the making.
I no longer believe experience causes you to innovate less. Rather, it lessens willingness to harm because it deepens your understanding of it.
Many leaders don’t understand what makes a team operate efficiently, but I have a simple system: You evaluate team efficiency by how much you can remove.
I recently heard about a company that underwent layoffs and then awarded bonuses as normal anyway. I dig into the structural reinforcements that enable what appears to be unhinged behavior.
There are fundamentally two types of power in any community: hierarchical & social. I reflect on what I’ve learned in the past year and how I think about the future of Icrontic.
11 years ago, Mark Rosewater coined “lenticular design” as a term of art in game design. Here, I adapt his introduction to the concept to demonstrate its relevance to software product development.
If you find yourself arguing for something “on principle” and laying out complex reasoning, you probably stumbled at the outset and already lost.
I’ve been reflecting a lot on my inability to develop habits and unpacking what’s underlying that. It’s never too late for a new strategy!
I had exactly four months between gigs, so I’ve recounted how I invested that time off of anyone’s payroll.
Friends know I’m a bit of an album fanatic, with 70s-era Pink Floyd responsible for the initial push. These are 50 of my favorite albums, without repeating artists.
As autumn deepens into winter with the first snow of the season here in Detroit, these are recent articles that have deepened my understanding of the world at the intersection of community, the open web, polity, & learning.
Generalists solve many early business problems, but you can summarize most of that list as “effects of inexperienced management.” By building a team of stakeholders instead, you create opportunities that might just save your organization one day.
Web 2.0 enabled collaboration on a scale the world has never seen, but it only granted us collaborative labor, not collaborative authority… except for Wikipedia.
I’ve been thinking about Web-based community software for most of my life and have refined five beliefs for what must come next.
I find many senior software and IT folks don’t know how to talk about the value of tools. I frequently get asked by peers, inside my company and outside it, why I can successfully get tool expenses approved when theirs get rejected. Here’s my simple framework.
A brief recounting of the power of the written word across my life and career. Leadership isn’t in a title, it’s in your words, and you should beware anyone suggesting you outsource them in the name of efficiency.
What is debugging, really? I’ve thought about it for most of my life and never really come up with a satisfactory answer until today.
Several executives over my career have sat me down, looked me in the eye, and implied I was a naive fool for trusting my employees. Fuck ’em.
My annual “spring is here” post, wherein I connect a 6-year old task I finally completed to our country’s history, my home, and the work ahead of us.
It was quite a roller coaster of a week. Remembering what a privilege certain moments are can help even out the ride.
I don’t understand career goals. Is my career a list of job titles, start dates, or projects I delivered? I don’t think so.
It’s going to be especially important where your time, attention, and money goes over the next four years. These are a few areas I’m prioritizing.
I’ve semantically overloaded the word “leadership” to the point that I occasionally forget how far removed my definition is from the popular lexicon.
This is a reflection on my first resignation in late 2006, nearly 18 years ago, that I found today while looking for a document in my attic.
A hallmark of a healthy company is keeping incentives aligned with ownership. The only way to scale this is to focus on alignment, not control.
Working relationships between humans are far more durable & valuable than those between people and a legal entity. What’s a company, anyway?
In a small & fast engineering team, it’s challenging to quantify work being done. There’s so much to do, and it’s difficult to categorize. How can you determine your capacity for addressing your strategic roadmap when stakeholders ask about it?
If you start your career debasing yourself in drudgery for someone else’s profit, you won’t acquire the leadership & critical thinking skills you need and you’ll suffer for it.
It’s very difficult to talk about violence even among close friends over drinks, let alone on social media or other online venues. We need to anyway.
Patrick O’Keefe of the long-running show Community Signal asked me to join him in a discussion that ranged from private equity buying community software, community data ownership, and the stakeholder challenges of community software roadmaps.
Building on the Web these days often feels like a game where you see how much weight you can put in a boat before it sinks, but you get $1 for every pound you add instead of how many days it stays afloat.
Psychological safety is the most powerful productivity multiplier. Without it, no one can take ownership of their piece of the company and make it better.
Software building is a team activity, and QA is an indispensable stakeholder on a well-functioning team.
Have you ever noticed nearly all Web software is feudalistic? I share three important pieces from academics that capture the issue.
I’m thinking about how easy it is to get locked into a path. We tell ourselves lies about who we are every day and make choices based on those lies.
We usually ignore transition time. If your focus needs to transition, make space for that.
What would you say is the single best predictor for success for an engineering leader? They prioritize listening to the voices with more direct context and they are actively building their understanding of the problem set.
How does an executive bully operate in the workplace? Knowing the signs can help clarify your decisions and make the experience less traumatic.
Leadership skills are the water I swim in and it took a couple years in the corporate wilderness to remember that.
Before Kyle died, I didn’t understand what anxiety was.
Moments worthy of victory laps come from stories which have a beginning, middle, and end. If you’re not actively communicating these stories to a team, eventually startup-era victory laps fade into memory.
A catalog of media I consumed in 2021, with a sentence or two about each.
I’m the kind of person that waits to see what the third person decides before I open up on the first attacker. I’m being physically assaulted and I still try to deflect or defer, to see where things go, before I hit the gas.
A few months ago, an old friend called me the “least evil person” they know. I keep thinking about it.
The most egregious error I see leaders make frequently is to assume they have more context than the folks doing the work.
When I was in middle school, I fell in love with a boy. I’m pretty sure he liked me back. It’s a simple narrative, but it took me most of my life to understand it.
10% of all commits on the decade-old project are now mine from this past month. So, things are moving briskly.
