Michael Boykin

This Week in Startups community AMA

A TWIST Q&A on building culture, navigating WFH, product development, and the evolving changes to the startup world

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Last week, Range co-founder Dan Pupius joined Jason Calacanis on the [This Week in Startups podcast to discuss everything from workplace performance and management philosophies to his experience leading teams at Google, Medium, and now Range.

This week, Dan stepped into This Week in Startups’ Slack channel for an “Ask Me Anything” (AMA) session with the community. He fielded questions around managing WFH, product development roadmaps, working with investors, and the future of Range. We’ve put together a recap of some of the session below.

Do you personally find it challenging not to be in the same physical space as your team?

We actually didn’t start Range to be a remote work company. We were mostly interested in making work better for everyone, doing a lot of research into the challenges facing teams as they try to scale. What we noticed was that remote companies are generally more intentional about how they set up their processes and that the problems that they face are actually amplified versions of the problems co-located teams are facing.

What that meant was as we started solving problems for teams Range resonated most with remote teams.

From a personal point of view on not being in the same physical space, I actually don’t find it challenging. I do like working in an office. I do like having a desk, a mini kitchen, and randomly bumping into people. But some of my best collaborative moments have been with people not in the same office as me, such as when I was working on Gmail Chat.

What advice would you give around developing and sticking to a product development roadmap as a first-time founder?

One of my favorite quotes, which my team get very bored of me quoting, is “Planning is everything. The plan is nothing.” What that means is the act of planning is very useful; it’s a way of orienting yourself and figuring out which direction you should go. But once things are in motion the plan can be a liability.

"Planning is everything. The plan is nothing." — Dwight Eisenhower

So, what I would say is sticking to a roadmap shouldn’t necessarily be the goal. Solving customer problems is the goal, and you work out a roadmap which is a hypothesis for how to solve those problems and fulfill customer needs in order to build alignment with your team. But you have to be agile and flexible — especially at early-stage startups — about that roadmap and adapt as necessary.

Generally, I recommend writing down your roadmap, holding planning sessions with your team, and evening developing a company manifesto. Documenting your plans is just the starting point.

What’s a good way to establish and calibrate sprint lengths when looking at various aspects of the build?

One important thing to think about here is that there are two cycles that don’t necessarily need to be combined. The first is a cadence of communication that is about how your team comes together to communicate and align on a north star. The second is your work cadence, which is about how you do project planning and measure units of work.

In some companies, it’s possible to have those two cadences align — you might do a two-week sprint on work and align it with your communication cadence. But at other companies, especially as they grow, different workstreams naturally have different cadences.

Start by defining the cadence of communication, which is when you start planning. At Range, we do a Monday morning briefing and have two-week sprints. We plan our work for two weeks and have a retro at the end of the cycle with the whole company.

What are best practices around building a tight, mission-driven culture when working remotely?

Have you set out from the start to build a remote company or have you been thrown into operating remotely? Those are two different realities.

If you are building a remote company from scratch, then a lot of this comes down to hiring and onboarding, making sure you’re attracting people who understand the problems you’re trying to solve and who resonate with the mission. Unfortunately, a lot of people are now in this remote work situation where they haven’t been able to build a solid foundation.

A tactic to think about here is establishing rituals and rhythms, which goes back to the cadence of communication. You have to have this drumbeat where you’re reinforcing why you’re doing what you’re doing, and that has to ladder through the company. Some companies use goals and OKRs to accomplish this and build alignment.

Have you received any downstream investor interest since the start of mass quarantine across the US? Do investors see this as an opportunity?

In short, yes. I think there are a lot of investors who are healthily skeptical of productivity and team software, especially in the HR space. And now they’re suddenly realizing there’s a big opportunity here. The world has changed and they’re trying to understand the market. So there’s definitely a lot of opportunity and this has been accelerating a lot of trends we were already seeing in the workplace. If you think about what the operating system for work looks like in five, ten years, it looks very different from the stack of today.

Can you share a little about where you want Range to be in 18-24 months? How are you planning on scaling and what does your product roadmap look like?

Ultimately, our goal is to help teams be more successful. In 18-24 months, I’d love for our customers to look back and say, “Yes, Range really helped our teams navigate this really difficult time.” I think that Range can really help companies right now, helping them to build strong foundations for good teamwork.

On the product side, we’ve been focused on the team as the unit of work. It works pretty well for teams as a way to stay connected and know what’s happening. What we’re looking for over the next year or so is to deepen product value for the individual, team, and organization.

On the individual level, we already integrate with the tools you use every day, so I’m pretty excited about some of the work we’re doing around attachments and integrations to really nail your personal workflow.

For teams, we’re looking at cadences, these rituals and rhythms. We see an opportunity for Range to help teams build that cadence and find their own groove.

At the organizational level, we’re starting to collect some very interesting data across tools and updates. We’re looking at how we can provide insight and help companies function better on the whole to increase both team and organizational value.

Really like the use of daily check-ins and achievement tracking within Range to keep people on-track. How can we encourage these actions in important areas outside of work where people aren’t directly incentivized to do so (fitness, eating, learning)?

One of the things we looked at with Range was how to encourage behavior that people may intellectually know is valuable but doesn’t stick. Even the daily check-in, or work planning, is something that everyone knows makes them more productive, but a lot of people don’t take that time at the beginning of the day because they just get caught up in the rush of work.

When you look at behavior loops there’s a cue, something that triggers the behavior, the thing you actually want to happen. Then you need to have some type of reward.

That reward reinforces the behavior. For Range, we actually have multiple overlapping habit loops around the behavior, so multiple cues and rewards. When you’re looking at other areas you have to think about the same things. With fitness, what is the cue to exercise, and what is a cue that will be motivating? As someone who exercises fairly regularly, a notification isn’t going to be the right cue to get me to go on a run. But my watch telling me I’m now unproductive might. And then, what’s the reward on the other side?

What do you look for in a co-founder, and what advice would you give to founders looking for one? Do you even need to?

When we were starting Range, it was really important to have a good spread of skills, abilities, and behaviors. And I think Braden, Jen, and I really complement each other really nicely. There’s very little overlap in our core disciplines. From a behavioral perspective, we all bring different points of view to the table. I think it could be pretty tricky if the founding team all comes from similar backgrounds, focuses, or skills. This can make you a bit blind to opportunities.

Looking for a foundation of trust is key. You will have conflict, and conflict is good if you can handle it and process it effectively. I think what often happens is founding teams try to avoid that conflict, which creates this kind of seed of doubt and lack of commitment to each other that can eventually blow up into something, eroding the trust over time.

I personally wouldn’t want to build a company on my own. It’s really difficult. Being able to lean on other people to step in if you’re having a bad week or month is really valuable.

What should self-funded startups be thinking about right now and 24-36 months out?

No one knows what the world is going to look like two or three years from now. It’s all reading tea leaves and making predictions. I think the main thing to do is think through various scenarios and your own hypotheses. That might be based on optimistic recoveries or it could be something more extreme. But from there you can start to ladder back from these scenarios, think through plans, and spot commonalities.

Any tips on joining a small tech team as a new leader, particularly fully remote teams?

A lot of this depends on your background. If you come from a big company and were a leader there, then everything is going to look different at a small company. You have to reassess what the role of a leader is and rethink what your day-to-day job looks like.

One mistake people in roles of leadership can make is failing to recognize that there are three levels to work: establishing a vision, writing the playbook, and running the playbook.

If you’re a very senior leader in a big company, then you can get away with just setting the vision and not actually being able to write the playbook. You can delegate that to someone else. But when you go into a start you must be prepared to get your hands dirty. You have to be able to write and run the playbook.

Are you a leader or a co-founder? Can you be both?

You can definitely be both. I think everyone is a leader. Leading is about having an idea and taking action towards that idea and influencing others.

Co-founder isn’t really a job, it’s a title. Co-founder doesn’t mean anything. It doesn’t tell you about what I do or what value I provide. It just means I was there when the company was incorporated.

As the company grows, “co-founder” can be this amoral compass that can anchor the organization, which can be valuable, but it can also be harmful because it can imbue authority where authority doesn’t necessarily need to be as the company grows.

We prefer to talk about your role versus your title. Your role is the hat that you wear, and that hat can be taken off and given to someone else at different times. At a small company, I do a lot of work that isn’t typically the work of a CEO but there are other hats I have to wear.

How do you split up your day working at a remote company? Do you have days when you do certain work?

Abstractly, this depends on your energy level and how you like to work. Some people prefer to have a day of focus time. Maybe that’s your coding day. Others prefer horizontal blocks of time. So, coding in the morning and maybe investor meetings and 1:1 meetings in the afternoon.

For me, I follow much more of a GTD methodology. By that I mean if something will take me less than five minutes I’ll just do it to get it off my plate and out of my mind. I don’t want to store things in my mental cognitive space longer than is necessary. I sketch out my day in Range and pull things off my list throughout the day, setting deadlines for myself as necessary.

There will always be a lot to do, and things will always be urgent. Plans won’t hold, and you’ll have to get good about rolling with the punches and riding the ride.

What do we lose by being remote, and how do we get it back if we stay remote?

The biggest thing we lose are the chaotic interactions that happen in the workplace. Pixar designed their offices to force random, chaotic interactions. They architected where the offices, the toilets, and the kitchens were so people would run into each other. Those interactions are used for transmitting information and sharing data, but also for renewing belonging cues. When you don’t have those common spaces you lose a lot of those ad hoc interactions that build that foundation for healthy teamwork.

When you go remote, you have to think intentionally about how you build this foundation for your team. You have to be more intentional, but when you get it right it can create a much more inclusive culture and community.

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