How to stay scrappy

And keep your team happy

John Saito
Sep 5, 2018 · 6 min read

If you’ve ever worked on a small team with limited resources, you’ve probably felt it — that scrappy spirit. That itch that gets you going when the going gets tough. That burst of motivation when they say you aren’t good enough.

Time and time again, I’ve seen how amazing things happen when you tap into that feeling of scrappiness. But how do you keep that scrappy spirit as your team gets bigger?

A few months ago, I joined the Dropbox Paper team. By that time, the team had already grown to a pretty big size. I still remember my first team meeting and thinking we could probably fill a whole movie theater. (I was already daydreaming about offsites, I guess.)

Now I’m a few months into it, and I’ve noticed something: Even as our team gets bigger, we’ve somehow kept the scrappy spirit of a small team. I don’t know if this happened by chance or by design, but here are my theories about how we stay scrappy.

🚀 Progress over process

The other day, I was chatting with our Group Product Manager, Kavitha Radhakrishnan, and she said something that knocked the wind out of me:

“Specs become outdated as soon as you’ve written them.”

If you read my story about design docs, you know how I love me some good documentation. But as I thought more about my recent projects, I realized she was on to something.

Specs are great for getting aligned on a project’s goals and scope. But once you start putting your concepts into code, things rarely go as planned. At that point, progress becomes the priority. Documentation becomes an afterthought.

I’d say 25% of the real design work happens after a designer hands off their designs. That’s when engineers start pressure testing your designs, and they’ll find new constraints and edge cases you never expected. At that point, you gotta get scrappy and do whatever it takes to move forward.

On the Paper team, we’ve learned to roll with the punches and embrace the fact that plans will change — no matter how good your specs are.

🙅‍ No ivory towers

As a company gets bigger, the people making the product tend to grow further and further away from their users. Know a designer or product manager who works at a large company? Try asking them how often they talk with their everyday user. I bet you’ll be surprised by what you hear.

On the Paper team, we try our best to not build those ivory towers that distance ourselves from users. Instead, we do scrappy things to get to know the people who use Paper.

One thing we do is called Real World Wednesdays, which was started by one of our researchers, Mira Rao. Every other Wednesday, we invite people to come by our office to get their thoughts on stuff we’re working on. It’s set up like a speed dating session, so a participant chats with several people from our team, one at a time. And the nifty part is that designers, engineers, and product managers are often the ones interacting with these people, not a researcher. These sessions get us in the habit of talking with real users on a regular basis.

We also schedule casual chats with teams who use Paper. We like to see how people use Paper out in the wild, and we’ll visit their office if we can. Anyone on our team can tag along on these visits — designers, writers, engineers, whoever. Every chat is a chance to inspire us and learn something new about our users.

A few Paper peeps chatting with the team at Airtasker

🎮 Hack time

A lot of tech companies have “hack weeks” where you can work on whatever project you want for a whole week. On the Paper team, we have hack weeks, but we also have something called “Hacky Hour.”

Every few weeks, on Friday afternoons, we get together with some drinks and hack on whatever we want. We can spend an hour hacking, or we can spend a whole afternoon on it.

Believe it or not, many of the features that Paper users love most were built during these hack sessions. Ever try presentation mode? That was a hack project. How about emoji titles? Yep, hack project, too.

Paper wouldn’t be where it is today if it weren’t for these hack sessions. When you give people the time and space to play, you’ll be surprised by the scrappy things they come up with.

Leandro Castillo and Sheila Ramaswamy hacking away during Hacky Hour

🤠 Role play

On the Paper team, it’s not unusual to see people playing different roles on different projects. I’ve seen product managers running usability studies. I’ve seen researchers doing design work. We have assigned roles for everyone, but we’re empowered to wear different hats, too.

At large companies, it’s so easy to back away and say, “Sorry, that’s not my job”—because large companies have such specialized roles. You don’t just have a designer. You have an interaction designer, a visual designer, a motion designer, a systems designer, and so on.

But over here, job titles don’t define us. We just do whatever it takes to get stuff done. I’m a writer, but I do some design work from time to time. Neil Sethi and Caroline Frost are product managers, but I’ve seen them dig into the code and build amazing things.

It’s pretty humbling when you see people all around you getting super scrappy, just to help each other out.

🙌 Small wins

For whatever reason, our team loves giving kudos to each other. Seriously, I have at least two meetings a week where we set aside time to give kudos and thank other folks on the team.

To make things a little less awkward, we also set up anonymous forms, so people feel less shy about laying on the love.

On the surface, kudos might seem like a silly tradition, but I’ve noticed how kudos lead to one good thing after another. Person A gives a shout-out to Person B, then Person B feels good and gives a high five to Person C. Before you know it, everyone’s chipping in a little bit more each week.

Everyone wants to feel valued, and a simple thanks goes a long way in helping people feel appreciated, energized, and united as a team. It’s not just the big launches that matter. Celebrate the scrappy small wins, too.

💙 A love for experiments

The Paper team loves to experiment. At any given time, there are dozens of feature experiments we can switch on to try things out internally. We have experiments that play with layouts, experiments that play with UI copy, experiments for pretty much anything.

For example, here’s an internal experiment created by Aisha Ferrazares and Harold Check, where we show a warning if you try to send a notification to everyone in a doc:

We wouldn’t launch this as is, but it helps us feel whether this is helpful or not.

We try to make it as easy as possible to push out experiments within our team, because we want to make it easy to see what feels good and what doesn’t.

We’ve also been experimenting with different ways of working. We’re now trying something called “hack-a-sprint,” where a small group focuses on one project for 6 whole weeks. They can skip all meetings and other responsibilities, so that they can focus on just one thing. It’s like having a scrappy startup within a bigger team.

So there you have it. I’m no organizational psychologist, so take it all with a grain of salt. But from what I’ve seen, these are the things that keep our team feeling scrappy and happy.

If you’re on a growing team, looking for ways to stay scrappy, hopefully these tips will jumpstart some ideas in your head.

Oh, and if you have thoughts you want to pass along to the Dropbox Paper team, feel free to leave a comment below. We’d love to hear from you.

Hope you enjoy using Dropbox Paper as much as we enjoy building it.

Want more from the Dropbox Design team? Follow our publication, Twitter, and Dribbble. And if you’re looking for a new gig, come join us!

Thanks to everyone who helped bring this story to life, including Kurt Varner, Igor Kofman, Kavitha Radhakrishnan, Roxy Aliaga, Neil Sethi, Caroline Frost, Mira Rao, Sheila Ramaswamy, Leandro Castillo, Aisha Ferrazares, Harold Check, Andrea Drugay, Faryl Ury, and Justin Tran.

Dropbox Design

We believe joy is the engine that powers the best ideas.

Dropbox Design

We believe joy is the engine that powers the best ideas. We’re designing a more enlightened of working, so you can love the way you work. More on

John Saito

Written by

Design @latticehq. Always chasing rainbows.

Dropbox Design

We believe joy is the engine that powers the best ideas. We’re designing a more enlightened of working, so you can love the way you work. More on