Having spent over a decade building tech startups, I’ve come across my fair share of tech debt: The gnarly Ember.js code no one wants to touch, the bespoke cloud infrastructure maintained entirely by hand, or the solitary Elixir service …

3 February 2023 | by Todd Wenning, CFA

I’ve stopped wearing merino base layers. The change wasn’t deliberate, sudden, or driven by a deep concern for the wellbeing of rare sheep. Instead, it happened naturally over time, because the latest generation of synthetic next-to-skins …

For the last handful of years I’ve been too busy to do a lot of things. Too

I like to be immersed in useful information, and often dreamed of ways to have it literally floating above me so that I could glance up and see something new and interesting.

I spoke with someone recently who didn’t know where to start with their first hire in Developer Relations. As folks who know me appreciate, I think of the Developer Relations organization as the following distinct functional areas:

Teams naturally start to incur management debt as they grow and become more complex, just as codebases incur tech debt. The combined weight of past decisions creates a web of precedents and exceptions that can cause problems of varying size …

We’ve all been through reorgs before. When you’re an individual contributor, they tend to be mysterious, often frustrating management exercises. Your boss changes suddenly, or your team is dissolved into other teams, or you’re moved into an …

I’ve been writing about how to use systems thinking in software engineering management. I want to continue addressing a practical point: how to make change happen as an Engineering Manager (EM).

Too many companies bet on having a cut-throat, high-pressure, take-no-prisoners culture to drive their financial success.

Over the last few months I’ve worked with teams to help them adapt Shape Up to their specific context. Talking to a wider variety of teams has been eye-opening. It’s helped me discover many hidden factors that were present at Basecamp when …

Last week I was on a panel addressing the topic of burnout. It’s a topic that pops up with some frequency, yet the misconception that burnout is a personal problem seems to persist.

Strategic leadership can often sound abstract and hard to put into words. Not only that, the majority of the CTOs, VPs and engineering leaders I work with are so busy running from meeting to meeting, handling team issues or trying to scale, …

Pros of working directly for CEO:

“The very business of getting an organisation made up of individuals, no matter how disciplined, to pursue a collective goal produces friction just as surely as applying the brakes of a car.”

The concept of “healthy teams” is something I stole from the Engineering Org at Pluralsight before the Vista acquisition. Most people attribute healthy teams to buzzwords like “collaboration” or “psychological safety.” The people who had …

Guiding principle in effective product development culture.

When work is coming at you from all directions, it’s easy to push even the simplest tasks aside. You may find yourself repeatedly looking at the same paperwork or email and promising to get to it later.

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Hiring folks in leadership roles is very challenging. One difficulty is that almost every candidate who gets to that level is generally good at communication, charismatic in their demeanor, and well trained to say the right things to get …

Picture this: you just landed the Product Management (PM) job of your dreams. On day one, you meet your partner-in-crime Engineering Manager (EM) at your new gig. Before you know it, you’ve been assigned your first problem to solve. Now, …

We’ve seen sharp focus pulled onto the growth of plugins on WordPress.org in the last couple of weeks. For many years, it’s been possible to see a plugin’s active install growth rate on the Plugin Repository.

Every developer knows the satisfaction that comes from building a software system. Type in a stream of characters and somehow you’ve built something that appears magical to others. This is the Builder’s dream. The thrill about learning …

Career advice as a genre is almost fatally flawed. With 160 million American workers across thousands of occupations in hundreds of industries, saying anything that is of use to all of them is practically impossible. The most common counsel …

The Connectivity Standards Alliance has certified and released the first version of the Matter smart home interoperability protocol Tuesday and I couldn’t be happier. This means that member companies can now put their devices through the …

How to plan? How hard could it be? 4k words on sunny October afternoon for people in tech observing the Season’s Traditional Annual Planning Process, inspired by a recent interview question (and 25 years of variously painful planning …

Crowded Boat II, Robert Goodnough

The Dirty Work Theory: The lamentable work that many people avoid are great places to look for high impact, low hanging fruit.