A Health Savings Accounts (HSA) lets you save money pre-tax to use for medical expenses at any time in the future. You can also invest the money if you plan to use it in the distant future, such as in retirement. It’s one of only a handful of vehicles for pre-tax investing, which makes it very attractive. HSAs exist in large part to get people to enroll in a High Deductible Health Plan (HDHP). Even though HSAs look attractive financially, they are non-financial drawbacks that are not obvious at first. Benefits of HDHP + HSA The premium — the amount of money coming out of your paycheck automati ..read more

What is Burnout? Burnout is a state of poor professional mental health, where the feeling of being overwhelmed or a lack of enthusiasm impacts your effectiveness. It can be caused by a mixture of mental or physical exhaustion, lack of belief in the work, and lack of belief in yourself. Each individual has a personal expectation about an ideal work environment on these dimensions. When reality becomes too far detached from this ideal, the result is burnout. If you are currently burned out, you probably already know it. It feels like a crippling inability to get things done or to even care. It’s ..read more

When there are many managers in a large organization, how do you make sure that any performance ratings, promotions, and subsequent compensation changes are fair, relative to each other? A common mechanism is for all the managers to get together, and compare notes — or “calibrate” — on their team’s ratings and promotions. Why Calibrations? Calibrations are primarily about reducing the bias of ratings from individual managers, and increasing equity between managers. Secondarily, they are a great way to train managers on how the company thinks about performance. They also give senior managers da ..read more

For engineering managers, delivering projects reliably and on time is a critical part of the job. Even if everything is estimated and executed well on your team, dependencies can derail you. If you poll a group of managers on their top risks — and I have — they will come back with a list that’s 80% dependencies on other teams. But many will feel helpless to resolve those dependencies. If your project requires another team to prioritize your dependency, what can you actually do to mitigate that risk? Not needing dependencies is a luxury afforded to teams in small companies, or those running ver ..read more

Organizational Design is how you group teams together in order to optimize for various constraints. There is no perfect organization design, only a series of trade-offs. Unless you’re a small company, how you group teams together will optimize for some dimensions and constraints over others. No organization design you choose will remain stable any longer than a few years. But you can mix and match different design strategies for different parts of the organization. What is an Organization? An organization is a set of teams with one name. Your company is one organization. A large company includ ..read more

When working with a new manager that’s reporting to me for the first time, I like to share this document. Hopefully, it helps us get on the same page about our shared expectations for your role. I hold myself to the same bar on all of these – you can expect the same things from me that I expect from you. These are probably not controversial. If they are, let’s talk about it! Weekly 1:1s You should have weekly, regularly scheduled 1:1s with your direct reports. For most roles, this will be somewhere between five and eight 1:1s a week. For product teams, you should also have weekly 1:1s with you ..read more

Five years into my career, I had gone from being one of the few engineers at the company, to being the expert on a medium-sized engineering team. If someone misunderstood how something worked, I could list all the ways there were wrong. If someone had a product idea, I could find all the ways it might not work. I even remember joking about this by saying, “if you need someone to poke holes in an idea, you know who to come to”. No one ever said anything directly, but my manager started getting feedback about how I was coming across. I got some formal 360 feedback that was filled with phrases de ..read more

It was a meeting with my design and product partners. Just the day before, we had been brainstorming ideas for the strategy for the coming year. In the 24 hours between, I had written up a draft of a strategy. It was more to gather my thoughts than anything else. My design partner smiled, and I worried that maybe I had overstepped. But he wasn’t annoyed or surprised. Instead, he was complimentary. He said, “I’m always impressed by how quickly you get to an 80% draft, and how you’re OK with sharing that early work”. It’s true. In a leadership role, we’re asked over and over again to produce cla ..read more

What is strategy, versus vision or mission? Is a business goal a strategy? It’s hard to tell whether a strategy will be successful, up front. When you’re creating a strategy, it can seem impossible to achieve. In retrospect, a good strategy seems like it was obvious, even though it was anything but. In this post, I’m going to use the rough outline of a case study, to root the conversation. Because this is such a well know case study, the strategy may seem obvious in retrospect. Having been alive and following this company during this period, I can attest to the fact that it was not obvious wha ..read more

I’ve given this Agile planning workshop a few times. It’s Thanksgiving themed, because that is the time of year when we are making plans for the next year. It can help decide what some reasonable commitments are for large, multiple quarter efforts. Send out these pre-reads ahead of time: Getting Started Estimating with Story Points Estimating Epic Stories in Three Steps. What is this workshop for? (1 minute) In this workshop, we are going to learn how to estimate Epic level roadmap items. For example, these could be the primary projects for a team of engineers for an entire year. When Estima ..read more