Jacob Kaplan-Moss

I’m a software developer, co-creator of Django, and engineering leader. I work at Latacora, co-own REVSYS, and am the Treasurer of the Django Software Foundation. Previous jobs: Hangar, 18F, Heroku. If you’re looking to contact me, please see how to get in touch and the ways I’m available to help.

Writing

So you've been reorg'd... March 12th, 2024

I’ve been through close to a dozen reorgs. This article contains the advice I wish I’d been given earlier in my career when I didn’t yet have that experience. Reorgs are disruptive, and nobody really tells you what to do in the wake of one. It’s easy to feel adrift, scared for your future, and uncertain about how to behave. Some of that fear is warranted: your job security probably goes down in the months following a reorg. But confusion and chaos aren’t necessarily signs that the reorg will go poorly, and there are things you can do to help give you and your team a better chance of emerging successfully.

Estimating Software Projects: Breaking Down Tasks March 11th, 2024

Something missing from this series on estimation, until now, has been a discussion of how to “break down” a project into a well-defined task list. I’d not previously written about this because, to me, it’s largely intuitive. But it isn’t for everyone, so this post fills the gap, and explains in detail how I break down projects into a task list.

Paying people to work on open source is good actually February 16th, 2024

If you have a problem with maintainers getting paid then you have a problem with me and I suggest you let that one marinate.

Tracking Engineering Time February 7th, 2024

How do you understand what engineers are doing with that time? How do you know if they’re working on the “right” things? Here’s how I suggest answering those questions.

Philanthropy Update January 10th, 2024

Lessons learned and updates from a couple of years of executing on my philanthropic plan: finding and tracking organizations, continuing to wrestle with anonymity, and a list of donations we’ve made.

My Diverse Hiring Playbook January 4th, 2024

I’m really proud of my track record building diverse teams. When I’ve been responsible for hiring, those teams have consistently been more diverse than industry norms, often significantly so. Over the years, I’ve developed a set of “plays”, some go-to tactics for increasing the diversity of my hiring pipeline. This is that playbook.

Managing Technical Debt December 20th, 2023

My playbook for managing technical debt.

Making Decisions: First decide how to decide: “one weird trick” for easier decisions December 5th, 2023

This is my preferred decision-making process – a version of the “document-discuss-decide” process that I called for at the end of the part 1 in this series. The most important part of this process – its “one weird trick”, if you will – is the way it includes a “how shall we decide?” step. This separates out the meta-question of the decision-making process from the decision itself, which (I’ve found) makes decisions much easier.

Making Decisions: RFC processes are a poor fit for most organizations December 1st, 2023

The RFC process has been a huge success in defining the standards that run the Internet, but naively adopting this process for your company is a mistake. RFC processes tend to fail at most organizations because they lack a clear decision-making step.

Professionalism: No Yelling November 21st, 2023

It’s never acceptable to yell at work. The norms of professional behavior call for a cool demeanor. It’s normal to have emotions at work, but there’s a limit to how strongly you can express those emotions, particularly anger.

Performance Is Contextual November 20th, 2023

Managers often talk about performance as a static thing. We say that someone is a “high performer” or “low performer”, as if performance is a fixed attribute of their personality. This fixed mindset is a mistake. Performance is contextual: how well you perform your job is deeply dependent on the conditions around you.

Does someone need to be a good manager to give good management advice? November 16th, 2023

In a management Slack I’m in, someone responded to a list of commonly-recommended management books by asking, “are these people good managers though?” It’s a fair question! But it’s not quite so simple.

How to Build Trust November 16th, 2023

What are the major management behaviors that can help build trust? Management books often cover the importance of trust, but abstractly. There’s precious little writing about the nuts and bolts, the day-to-day tasks of trust-building. That’s the gap I’d like to try to fill with this article.

Seniority and self-management: you don't have to do this alone October 4th, 2023

At a certain level of seniority – typically the Staff level for ICs, and the Director level for managers – you’ll be expected to fully own huge areas of responsibility without detailed guidance. The mistake that many people make when they’re new to this level of autonomy is believing they have to do it all themselves. It is absolutely true that, once you reach this level of seniority, you are responsible for a very broad scope of responsibilities, skills, and tasks, but you don’t have to do this alone. At this level of seniority, you have to recognize your weaknesses, figure out what kind of support you need, and take steps to get yourself that support.

RTO vs WFH: my default recommendations for remote vs colocated teams September 29th, 2023

As companies start to roll out so-called “Return to Office” (RTO) policies, I’ve found myself disappointed by the hyperbolic arguments being made by remote work / Work From Home (WFH) proponents. I believe that neither remote work nor colocated work is globally “better”: which one works best is contextual, depending on the role and the needs of the team. In this post I’ll break down how I view that context, and share my “default” recommendations for which teams should be primarily remote, and which benefit from a shared physical space.

Team size isn't a measure of success September 11th, 2023

Most managers have internalized the idea that team growth, in and of itself, is a unalloyed good, and a sign of success. This is wrong, but it’s understandable. Team growth feels like success, but headcount by itself isn’t a measure of success. Instead, we should judge management success by impact and efficiency.

Mailbag: Should you give candidates feedback on their interview performance? August 25th, 2023

Should you give unsuccessful job candidates feedback on what they did or didn’t get right?

Do I need a consultant, contractor or employee? August 24th, 2023

When is it the right choice to hire full-time staff, and when should you use consultants or contractors instead? The short answer: hire consultants for guidance, contractors for execution, and employees for stability and flexibility. For the long answer, read this article.

Hire for Floors, not Ceilings August 16th, 2023

When you’re hiring, try not to get caught in the trap of evaluating candidates based on their best possible performance. Look instead for consistency: reliable results in variable conditions, the ability to deliver predictably with consistent quality, and so forth.

Giving It All Away: My Philanthropic Plan May 15th, 2023

A major personal accomplishment in 2022 – something I’m proud of – was creating a philanthropic framework. My wife and I intend to use this framework to guide our charitable giving for the rest of our lives, with the explicit goal of giving away almost all of our wealth in our lifetimes. Here’s some backstory, and all the details of our plan and the framework that guides our giving.

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