In this post, I talk about what I’ve learned in the past year at General Task with respect to getting the most out of your team. Some of these lessons are standard best practices and some of them are a little bit less conventional, and may not work for everyone, but I’ve personally found them to be quite effective for my own team. I hope you may find some of this useful as well.

Before I get started, I want to encourage you to give General Task a try if you haven’t already: https://generaltask.com/

One of the most important things I’ve learned in the past year is that my team is much more capable than I initially thought, and has grown a great deal as a result of being pushed hard. Perhaps due to the way I hired my team (discussed in the previous post), I am lucky to have a team of highly motivated, passionate, hungry people. Some people on my team are at the beginning of their careers, though, which made me question at first what could be accomplished.

And sure enough, in the early days, our product was riddled with bugs and even relatively normal product features were quite difficult to build. But I kept pushing for us to improve, knowing my team was capable of great things with more practice. I set ambitious goals that were impossible for the team at that time, but feasible for the team I believed we could become.

For example, in August of 2022, we put the team in “war mode,” compressing our 3-4 month product roadmap into an eight week sprint, capped by a public launch of our open beta. At first, I was worried I would overwhelm the team with such an ambitious challenge and receive a lot of pushback. But instead, I was met with enthusiasm and excitement. The team rose to the challenge, and team members told me they had never felt as much clarity of purpose as they did with that nearly impossible goal ahead of us. And we shipped our product perfectly on time.

A very important caveat here is you have to choose goals that aren’t completely impossible to achieve, and you have to work with the team to create those goals. When we proposed the eight week war-mode timeline, we first brought the proposal to our engineers and designers and asked them to figure out if it was workable. And the answer was: “it looks to be just barely possible.” Because of that buy-in, the goal was a shared objective that we all knew was possible, not a top-down directive that was out of touch with reality.

At General Task, the leadership team shares everything we responsibly can with the broader company, including financials, metrics, fundraising information, ongoing major decisions, and more. This has led to a healthy culture of transparency, which has helped us in significant ways.

Last summer, when we spoke about our runway and lack of traction (at that time) with the team, it was unclear when our product might get to the point it is at now, where many people outside of our own team love using it every day. That was unfortunate news, but we didn’t shy away from it, and we didn’t sugar-coat it. And because of our transparent culture, two of my employees felt comfortable telling me they would most likely start to look for other jobs if we failed to get traction by the end of the year. That was sad but helpful information, and it made me realize what needed to be done to retain valuable members of our team. Thanks in big part to this open line of communication, I’m glad to say both of those employees are still happily working with us today.

That mutual transparency also extends to our employees feeling comfortable sharing concerns and disagreements with us about decisions we make and things we do. I make a strong effort to wait on finalizing decisions until we can adequately discuss and address the concerns and questions of everyone on our team. And while I am the final decision maker, I almost never have to use my authority to override others on the team. I’ve found that the concerns brought up by team members are often valid and have led me to change my mind and make higher quality decisions as a result. And additionally, these discussions help create high levels of alignment and motivation on the team, because everyone feels that they have a real stake in the direction of the company and that their concerns are being taken seriously.

General Task was founded in the fall of 2021, at a time when remote work was still the norm on product teams. In order to attract top talent, we offered flexible working arrangements and so we have been a hybrid team from the start. As we progressed through 2022, however, things got more normal again and we wanted to find ways to have our team work more in-person while still maintaining the flexible workplace we promised.

To make in-person work more desirable, we decided to follow a rather unconventional strategy: open an office in any area where there are two or more employees, optimally located to minimize average commute time. That led us to open a new office in New York City, and move our Bay Area office north, from downtown Palo Alto to Redwood Shores. While I live in Los Altos and my own commute got longer as a result of this, the commute for our designers became much shorter, and they have been enjoying spending much more time in the office than before.

Thanks to our employees-first office strategy, we have 75% of our team choosing to work primarily in-person, up from 25% several months ago. No mandates needed. And with offices in both the Bay Area and NYC, two of the largest tech talent hubs, we have a larger available talent pool than companies with just one location.

One of the most important management lessons I have learned in the past year is to focus on the strengths of your team members rather than the weaknesses. In the beginning, I had an urge to point out every small problem I noticed and I focused much of my initial employee feedback on dealing with those problems and molding people into my idea of a good team member. What I should have been doing instead is learning the strengths of my team, and doubling down on them.

This mistake burned me pretty early on. When one of my engineers told me they found it hard to get motivated to work on large refactoring projects and preferred to make quick fixes, I saw that at first as a concerning motivation problem that needed to be fixed by having this engineer spend more time working on refactoring projects until they got more used to them. But that was counterproductive: in a fast-paced startup environment, sending more unmotivating work to one of my engineers wasted valuable time, even if I saw the potential for it to help in the long run.

After getting advice from several sources (including some great books and advisors), I switched strategies, and refocused this engineer on projects that were more product-focused and involved rapid iteration. Immediately, I saw a huge increase in output, and this engineer became one of our most productive team members over time.

Now, to be clear, there always need to be baseline expectations of performance and conduct, and you can’t ignore those. And I strongly believe that in the long run, with enough time and practice, you can turn your biggest weaknesses into your biggest strengths. I’m a living example of that. But I’ve also learned that doing so is a personal journey that may occur over the course of years, not weeks, and it’s not something you can force on someone. So, especially in the fast-paced land of startups, it’s important to overlook some minor weaknesses and focus on making the most of your team’s strengths.

I believe that one reason I have been able to push my team as hard as I have is because they are compensated generously and treated well. Because I initially started as a solo founder, I saw my first team members as incredibly important to the success of the business, and gave very generous equity offers so that my team could more fully share in the success of what we build together. I believe these generous equity grants have helped a great deal with motivation and retention, and I also think that, on a deeper level, it sends a message that I value my team. I truly do, and I say that, but actions can speak louder than words.

And it extends beyond equity—we have great health insurance, a 401k match (I believe saving for retirement is incredibly important), and, of course, free boba once a week. We have all federal holidays off, 20 days of PTO per year, unlimited sick leave, and a flexible working environment. Some of those benefits exceed what is standard for a startup to offer. But I believe it’s the right thing to do, I believe it helps us attract top talent, and I believe it’s a crucial part of getting the most out of our team.

Thanks to the strategies outlined above, the General Task team is highly motivated and extraordinarily productive. In just over a year, we’ve built a powerful productivity tool that our users love in one of the most crowded markets in consumer software. I can’t guarantee these strategies will work for you, but I learned that they are effective at least for my own team. I can’t wait to see what we accomplish in 2023.

And don’t forget to check out General Task! https://generaltask.com/