Productivity is essential to everybody’s workday, but it’s about more than filling up your schedule with tasks.
He talked to us about building a productivity tool for profitability first, working with an asynchronous remote team, and helping others achieve a calm, intentional workday.
- Iterate based on feedback
- Build with your mission in mind
- Focus on quality
- Produce content based on your values
- Blend the practical with the philosophical
- Let customers define your vision
- Manage trade-offs of remote work
- Create camaraderie with remote teams
- Cut down on meetings
- Rethink productivity
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08:05 – Iterate based on feedback
Talking to customers through all iterations of your product is key to working toward a solution that fits their needs better.
“The funny thing is that the product that we have today, Sunsama, is a daily planner that guides you through the process of planning your day, is a lot closer to what we had envisioned at the very beginning. But in some ways, building what we’ve built now was too ambitious to start almost. It was like, how do we get there? Also, we didn’t have as much intuition for how people work, how they go about their days, how they use their tools. It was through this process of building, launching, iterating and sun-setting all of these different products that we developed a very deep intuition for how our customers think about their workday because with each of those products, we were always in this space of calendars, meetings, tasks. So, we had this chance to look at thousands of people’s calendars, talk to them about how they’re running their meetings, how they use Asana or Jira or whatever. That all came together at a certain point with one of the iterations of the product that we built, which was Sunsama as this daily Kanban list.”
13:39 – Build with your mission in mind
You may stumble upon practical and useful iterations while you build your business, but it’s important to come back to the core focus behind why you started.
“Very early on we had built something. This was probably like 2014 before Calendly was a household name. We basically built something that was very, very similar to Calendly. We actually had paying customers, but there was just something about it where it didn’t scratch our itch that we had started with. It was like, ‘Okay, this is cool. We’ve built a way for you to more easily have people book times with you.’ That’s a valuable product as we can see — Calendly, incredibly successful company — but for us it felt too transactional. It was this small sliver of what’s going on in your day. We’ve made it easier for people to transact time, but it wasn’t really getting at that real core question that was eating at us, which is for the next 40 years, potentially, we’re going to be working behind a computer. How can we be thoughtful and intentional about what we’re going to do each day? We ended up sunsetting that one, not because it couldn’t work as a business, but it wasn’t something we were excited to work on for the next 10 years.”
19:54 – Focus on quality
Craft a really good product first to make it profitable before scaling.
“Everybody who works at Sunsama loves doing this. So, we just felt like it makes sense that our worst-case scenario is that we should just keep doing this. This is a product that we want to see out in the world, regardless of what some venture capitalist decides is valuable for the world. I think, even at the scale that we’re at today, I think Sunsama is a positive force in many people’s lives and we’d like to keep that going. That’s part of it. In terms of thinking about it from the business side of things, I think that in this product category, the only way to win long-term is for the product to feel really, really good. I don’t think you get there by lighting cash on fire. I think you do it by carefully crafting a really good product.”
23:05 – Produce content based on your values
When you have core values that form the foundation of your team’s work, you can use those philosophies to guide your marketing content.
“We’re interested in this question of how can you go about your workday in a way where you feel calmer, more focused, more in control? It’s not really about doing more. Maybe doing more becomes part of that, in some way, as a secondary effect. And how can work be an opportunity for flourishing in your life, as opposed to a destructive force, an all-consuming force. That question has motivated everything we’ve done from the beginning. We know we have to work, so how do we make this feel good? How do we make it feel harmonious with the rest of our life? So, I think some of those emails and the thoughts in those emails come out of that.”
26:33 – Blend the practical with the philosophical
Tools can help you complete your work and also support your values.
“At the end of the day, if you want to boil it down, we’re making a website with checkboxes. Anybody can do it. It’s not rocket science in that sense. But I think that what we are trying to do differently is build a tool that focuses around different ideas of work, different philosophies of work, while also being very practical, in terms of we have to use Asana, we have to use Slack. Okay, how do we take these tools we have to use and how do we blend it with a larger philosophy on how we should work and really how we should live?”
30:17 – Let customers define your vision
Focus on delivering quality outcomes for the customers you have rather than worrying about perfecting the long-term vision.
“We’ve always thought of Sunsama as your primary interface for your workday. It’s the place you log in in the morning and feel like, ‘Hey, I can run my whole day out of this product.’ That’s a hazy idea of a long-term vision, but the more and more we work on it, the more and more I feel that question ends up being a distraction. The more important question is, ‘What are customers doing with the product? What do they want? And what problems do they have? If we keep repeating that cycle, it seems like the vision takes care of itself.”
36:24 – Manage trade-offs of remote work
Asynchronous remote work comes with immense benefits for the team if you set expectations and manage the trade-offs of written communication over live or in-person communication.
“Everybody on the team is pretty bought into remote async deep work. I like to think that our process isn’t that onerous. The trade-off is you have to spend 20 minutes a week writing an update about what you did that week, which is still better than a one-hour one-on-one with your manager, which most people are doing or often people are doing. The trade-off is still pretty good. I think that’s one of the things you run into with async work. You have to write a lot. You have to type a lot. You can’t just show up and run your mouth, which is often easier. I think overall, it’s a better trade-off. No meetings. Actually, I lied. We do have one meeting a week on Mondays, but we don’t talk about work. We only talk about what we did that weekend. So, it’s just a chance to have some human interaction time with our colleagues.”
38:15 – Create camaraderie with remote teams
If you’re working remotely, you can adapt to using new tools and behaviors so you maintain a sense of community and culture.
“We have that call where we just don’t talk about work and we just talk about what we did with our families or books we’re reading or whatever, just hang out. I think that that’s helpful. We also have a group chat that is not work-focused. It’s memes and pictures and fun stuff, which also allows us to not flood Slack with stuff and keep work more async. I think one of the things for us is that I think we have been able to build a camaraderie about a different way to work, in a lot of ways. I think that, in a lot of ways, makes it not transactional. I think everybody on the team is motivated by building and having the time and space to build high-quality things. We don’t get to collaborate that much in a room on a whiteboard, but it’s not like we’re not collaborating. I still am leaving a bunch of comments on every Loom video. I’m leaving ideas on PRs. There’s still a lot of collaboration happening. In a lot of ways, it doesn’t feel like there’s a lack of that human element. It’s just different.”
46:30 – Cut down on meetings
Removing unnecessary and speculative meetings saves time and energy to focus on delivering the work in front of you that you know adds value.
“One of the big ones I feel that I’ve cut out is meetings. That’s been big for me, just being able to do the work that I want to do instead of talking about the work. I think that’s from a work perspective, the biggest thing that we’ve done. Then, cutting out any sort of, I don’t know what you even call it, the meetings with other people outside of the company that would have, ‘Oh, maybe this will pan out,’ just cutting all of that out. Not talking to investors who reach out. Not talking to … Yeah, those networking calls where it’s like, ‘Oh, something could happen.’ Maybe I’m going to miss out on something, but it just feels better to not do speculative stuff. When a customer is like, ‘Hey, here’s something I need,’ I’d rather spend my time on something that I know adds value than something that could maybe possibly add value in 10 years or something. I don’t know. For me, I think the big thing I’ve cut out is those meetings. That’s been really valuable for me.”
50:15 – Rethink productivity
Humans aren’t machines and thinking of productivity as simply increasing output per hour is impractical.
“Trying to do more or getting more done each day or each hour is a really bad way to think about productivity. I think that it tends to be something that we’ve caught onto as part of our industrial revolution notions of productivity, which is how do we process more widgets per hour in a factory? I just don’t think that that’s how humans function. We’re not machines. There’s a lot of danger in trying to think of a human being as a machine or a factory. For me, that stance on productivity and products that are focused on here’s how we do whatever in half the time or whatever, what have you, is not the right approach to productivity. That, for me, is the big one.”