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Irrational Exuberance

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Roadmap decisions rather than dates.

One thing that bothered me about Imprint’s product after joining was our lack of passkey support. Passkey support is a rare opportunity to increase resiliency to phishing attacks while simultaneously reducing login friction. If it’s good for our members, our partners, and our product, it felt like something we should have already shipped. Nonetheless, it was hard to get it onto the…

Middle management roles are also a trap.

Six years ago, I wrote Tech Lead Management roles are a trap . My argument then was that TLM roles present themselves as easier than moving into a full management role, but the tension between doing the software engineering and engineering management aspects of the role made being a TLM a much harder first management role than a pure engineering management role. I still agree with that post, and I…

Generated and suppressed demand.

Eight years ago, I wrote about my theory of restoring struggling teams , which came down to four steps: A team is falling behind if each week their backlog is longer than the week before. Solve by hiring more. A team is treading water if they’re able to get their critical work done, but are not able to start paying down technical debt or start major new projects. Solve by reducing…

Make no assumptions.

I’ve recently been thinking a lot about the concept of “soil horizons”, which is the idea that there are many distinct layers of soil, from topsoil all the way down to bedrock, which all combine into a soil horizon. Translating this idea into software, the ideal codebase would have a single uniform “code layer”, but a surprisingly large percentage of production…

Revised rules of engineering leadership.

From early 2014 through late 2020, I was working in hypergrowth environments, which are challenging, but also educational. The most valuable feature of hypergrowth is that your mistakes reveal themselves next month rather than next year, because things go wrong very loudly when you’re moving fast. I’ve been thinking a lot about hypergrowth recently, because Imprint’s business is…

Early and late-stage hypergrowth.

Last week, a colleague asked why I’d hired an additional new leader onto an important area rather than expanding an existing leader’s scope to incorporate that area as well. The existing leader was a known quantity and doing well, so why not keep expanding them? It’s a good question, and depending on the circumstances I might have done either, but explaining why I specifically…

Agents as scaffolding for recurring tasks.

One of my gifts/curses is an endless fixation with how processes can be optimized. For a brief moment early in my career, that was focused on improving how humans collaborate, but that quickly switched to figuring out how we can minimize human involvement, and eliminate human-to-human handoffs as much as possible. Lately, every time I perform a recurring task–or see someone else perform…

The agentic passive voice.

At some point, you will have learned about the passive voice, where the actor in a sentence is unclear. For example, my software didn’t compile. That’s a good example of the passive voice. However, you might not know the full set of rules, because here are some sentences in the passive voice that you might not recognize: Claude made an error in my writeup. ChatGPT messed up the…

Judgment and creativity are all you need.

When I joined Imprint a little less than a year ago, our deploys were manual, requiring close human attention to complete. Our database migrations were run manually, too. Developing good software is very possible in those circumstances, but it takes a remarkable attention to detail to do it. It was also possible to develop good software using Subversion and developing by ssh’ing into a…

Refactoring internal documentation in Notion

In our latest developer productivity survey, our documentation was the area with the second most comments. This is a writeup of the concrete steps I took to see how much progress one person could make on improving the organization’s documentation while holding myself to a high standard for making changes that actually worked instead of optically sounding impressive. Diagnosis There were a…