There’s a certain magic that happens in the right team, at the right time. I’ve seen it a few times in my career... whether it was a small crew at a fintech startup building trade settlement systems with a clear goal and almost no overhead, a tight team building profitable web and mobile app experiences for health, or being the only engineer building Xamarin’s docs infrastructure and shipping something that eventually scaled up to power all of Microsoft’s .NET API reference. These moments stick with me because they felt different. We were fast, focused, and just effective ... and then things changed.
Over time I’ve realized that effectiveness isn’t a fixed point. It lives on a spectrum. Or more accurately, on a bunch of overlapping spectrums. Every team, every company, even every individual contributor lives somewhere along these gradients... and what works beautifully at one point in time can start to break down if you shift too far or too fast without understanding why. Not only that, but there will always be friction in moving in any direction on those spectrums that, without planning for them, can wreak havoc on a team’s previously-proven effectiveness.
This is something I’ve wanted to write about for quite some time, so this post is gonna be the start of a series. Over the coming posts, I’ll dig into each of these areas of growth for a company/org/team:
Team Size
From tiny startups and teams that move fast and talk constantly to larger organizations that need structure, planning, and coordination layers to function. The benefits and tradeoffs change dramatically as headcount grows.Generalists vs Specialists
In a scrappy early team, everyone wears five hats and learns fast. As a company matures, deeper expertise becomes more valuable... but sometimes at the cost of speed and cross-functional awareness.Freeform Discussion vs Structured Reporting
Some teams thrive on fluid, ongoing conversations. Others need clear rhythms of status updates, tickets, and plans. Each style can work... but mixing them without clarity can grind progress to a halt.Design Process vs Just Ship It
A thoughtful, iterative design process with research and prototyping can lead to great outcomes... but so can throwing a prototype into the world and learning from real users. The trick is knowing when each is appropriate.On-Call Systems vs Cowboy Coders
I’ve seen engineers who thrive in chaos, jumping into production to fix fires or launch unplanned experiments. That can create momentum, but it also burns people out... and doesn’t scale. A well-run on-call system can be boring, but it’s sustainable.Move Fast and Break Things vs Root Cause Culture
Pushing code fast creates energy and excitement. But when problems start piling up, you need people who dig deep to understand what’s actually broken... and how to prevent it next time.Minimal Rules vs Heavy Compliance
Startups often pride themselves on speed and flexibility. But legal, privacy, and security demands grow with scale, and ignoring them can sink a product. The challenge is introducing structure without stifling progress.
None of these spectrums have a “right” answer. What matters is recognizing where your team is, where it needs to be, and whether the way you’re operating is actually serving your goals... or just serving inertia.
That’s what I want to unpack in this series. Not just what makes teams effective, but how to stay effective as you grow, shift, and face new constraints. Because moving along these gradients isn’t free; it comes with friction. And if you’re not intentional, you might find yourself fighting that friction for no reason, or missing out on gains you could’ve had by making a shift earlier.