Notes on engineering leadership
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The Omniscience Expectation and the Mardenfeld
For many leaders the hardest job they have is getting comfortable with not knowing. It is natural to feel like you have to understand everything about the area that you lead. And that’s a feeling that often cascades down through hierarchies. My boss expects me to be able to answer an arbitrary question on the spot, in order to accomplish that I need to be an expert on an increasingly large number of topics. I accomplish this by asking for more and more detailed information from my team, perpetuating this omniscience expectation.
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Briefly: Anonymous Questions
As leadership, Q+A serves several important functions.
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Push and Pull
A model I return to a lot when talking about engineering processes is Push and Pull. Often when we design a new process or system we struggle to get buy-in. That lack of buy-in can often be traced to having forgotten the Push, the Pull, or both.
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Catch me on First Round's In Depth Podcast
I recently sat down with Brett Berson for a wide ranging conversation about engineering leadership for First Round’s In Depth podcast.
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Briefly: The Value of Meetings, and Some Alternatives
Shopify continues to attract attention for it’s ridiculously reductionist takes on productivity, from meeting armageddon to more recently a meeting cost calculator.
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Software and its Discontents: Parts 1,2,3
Last year, after I left Dropbox, I spent some of my break interviewing people in industry about the state of software development. I started a blog series based on those notes. I had always planned to finish publishing it over on the personal blog, and then clean it up and bring it here to the “work” blog. But that plan has lapsed because I got busy, and because I’ve held off on publishing the 4th part in the series looking at labor relations given what a difficult year it’s been for tech.
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How to plan?
How to plan? How hard could it be? 4k words scribbled down on a 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 processes).
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Building Layoffs on a Healthy Foundation
It appears that the pace of layoffs in our industry, after growing throughout much of 2022 to peak in June, is slowing (at least according to layoffs.fyi). Now seems as good a time write down some quick notes on layoffs without seeming like I’m sub-blogging (is that a word?) any company in particular. This is not a complete guide to doing layoffs. I think there is room and need for someone to write a definitive guide to doing layoffs well, but this is not that. This post is just some things I think about when I’m not in the middle of a layoff that I’ve found reduce the negative impacts when I do find myself in the middle of a layoff.
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Interview Question: Why do leaders keep disempowering their teams?
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Briefly: 4 Reasons Writing About Software is Hard
There was a recent poll on Twitter about whether you should discount the engineering leadership advice from leaders whose in the field performance is perhaps less than ideal. Got me thinking about why writing about engineering leadership is hard. I came up with at least 4 reasons.
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Quick note: Dropbox
Hey all,
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Briefly: Friday wins and a case study in ritual design
Culture is what you celebrate. Rituals are the tools you use to shape culture.
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The 5 Whys of Organizational Design.
Recently I wrote about sizing engineering organizations, and how you can think about it as an exercise in managing concurrency. In understanding org size I talk about the mental exercise of thinking about how the number of concurrent work streams you’re taking on as a team applies upward pressure on the needs of your organization (e.g. you need more managers, who need more directors, who need a more senior CTO, etc) The inverse exercise is also useful.
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Questions for a new technology.
Given that coordination and communication swamp all other costs in modern software development it is a pressing area to invest in, especially as your team scales.
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On Sizing Your Engineering Organizations
One of the most frequent conversations I have with teams is how to think about organization size. Or rather we have a conversation that goes something like, “We need to double/triple/quadruple our engineering team next year, and now we need to hire a leader who has done it before.” And to have that conversation well you need a theory of organization size.
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FAQs from Coaching Technical Leadership
I’m 6 months into my second extended sabbatical from operating. It’s my birthday today and I’m taking some time to reflect on what I’ve been up to this year. And one of my favorite things I’ve been doing is coaching engineering organizations on how to be high impact. Relecting on that half year of chatting with CEOs, CTOs and VPEs there have been a few FAQs.
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Advice For a New Manager
Read the full articleI’ve been an engineer for a decade, and recently joined a company as Director of Engineering. I am a talented engineer, but this is a total different role, and it has been challenging. I was wondering if you had any advice. Specifically how do I measure my success now? How do I know if I’m being as productive or effective as I could be? I’m self taught, and there is probably some imposter syndrome, but any advice for someone who wants to grow into the role?
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Towards an understanding of technical debt
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Optimizing for Learning
I gave two similar keynotes back to back in San Francisco in September. One at Github Universe, and one at the Code for America Summit. I felt like I was bit rusty after taking over two years off to focus on the inward facing work at Etsy, but folks enjoyed them.
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Five years, building a culture, and handing it off.
After 5 years, the time has come. This is my last week as Etsy’s CTO.
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Surviving being senior (tech) management
I’ve got a short list of things I tell people they need to do to survive being senior management. This list has come up a bunch in the last week talking to different folks. So I’m writing it down so I don’t actually have to remember it. That’s sort of unfortunate because there are some alternate versions that exist in a super-positional state, but I think having it written down outweighs the flexibility.
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