The personal site of Dan Webb aka @danwrong.
I've been reading a load of articles about the rise of the player-coach and, unless you're running a ten person startup, they're wrong. As Flavor Flav wisely said, don't believe the hype. The setup is always the same. LeadDev's 2026 numbers show hands-on work among engineering managers jumping from 20% to 35% in a year. AI has flattened the cost of turning an idea into software, so the manager who…
As an advisor, this is familiar story: CEOs and CTOs are confused about why their engineering team has got slower as they've added engineers. "We've doubled the team but we're shipping less than we did with five people." The assumption is always that it's a people problem - wrong hires, bad process, too many meetings. It's not about tech debt, it's not about whether you've got a monorepo or…
Alright, everyone - I'm normally a hype train avoider and as such have avoided a) talking about AI and b) breathy enthusiasm on this blog. Well, that's about to change - this stuff has me hyped. Brace yourselves... Recently, I've thinking lots about how AI will revolutionize the workflow of cross-functional product development teams. But most of the examples of products being developed so far are…
I first became an engineering manager while at Twitter. Like most new managers, I knew nothing about the role. Fortunately, Dick Costolo, CEO at the time, personally ran a class for new managers - and my god, I needed it. One part that burned itself into my mind is regarding something that every manager dreads - delivering difficult messages. Whether it's a layoff, some difficult feedback, a…
Most managers and tech leads consider an important part of their role is being the "shit umbrella" — standing in the storm, catching all the crap from the wider org so your team can “just focus.” It sounds noble but it's a huge mistake that's going to prevent your team from really excelling and growing in their careers. That “shit” you’re shielding them from? It’s not always clean, coherent…
The other day I found myself confronted with that image of Elon Musk walking into Twitter HQ carrying a sink, with the caption "let that sink in." It was a moment of peak tech CEO dickheadery which I really didn't want to be reminded of, but it got me thinking about a common mistake many of us make when joining a new company: bringing in the kitchen sink from our previous jobs. The problem with…
If you’ve even been glancing at the startup/tech community you will not have missed Paul Graham's recent essay, Founder Mode , and the enormous amounts of surrounding commentary. It makes some sharp observations about the challenges founders face as their companies grow. It’s a great read and, of course, the problems are real but I fear the message to founders reads too much like: you are the…
While digging around in my notes app I found this old essay from my time at Meta Reality Labs that was originally posted internally. We were right in the middle of a team wide planning cycle and, as always, things were getting tense. At the time, we were using the very popular P0, 1, 2, 3, 4 system for prioritisation and, in a way that's probably very familiar to you all, everything was P0...…
One thing that isn't spoken about enough is that being an engineer at a startup is it's own unique discipline - it's almost completely unrelated to the kind of role you'd have in a company like Google or Meta. Before you accept a role at a seed or series A startup, it's worth knowing what you are in for and what it takes to really excell at it. Having been round this particular merry-go-round more…
So, you’ve just got a new job as an engineering leader. Starting any new role can be massively nerve wracking but throw in the fact that you are going to be a bunch of these people’s manager and the stakes get really high. How do you turn up on the first day being the biggest noob in the company but somehow gain some credibility with your team, your peer leaders and everyone else in the company?…