How We Tried to Design Our Own Book Cover (and How Jessica Hische Saved the Day)

Quick background: In 2010, I created a process called the design sprint, and in 2012, I brought it to Google Ventures. Since then, my fellow partners and I have run more than one hundred sprints with GV startups. Many people read our posts about the method and asked us to write a book with more stories and a how-to guide. So we did! You can find Sprint in bookstores now.

Last June, with a near-complete draft of our book in hand, we began thinking about the cover design. We’re a team of designers, so how hard could it be? (Spoiler alert: Turns out it is very, very hard.)

We wanted to capture the promise of going from problem to solution with great speed. But we also wanted to avoid a “designer-y” cover. Sprint is not just a book for designers — we wrote it to be equally useful to an engineer, a teacher, a startup founder, or a student. The cover should invite readers who have never thought about design at all.

219 rough ideas

To begin, we “sketched” on the computer: each person using clip art and their favorite illustration tool (that’s Sketch for Braden Kowitz and Daniel Burka, and Keynote for me). We ended up with 200+ rough sketches and variations. Here are some examples:

Five good designs

There were some promising ideas in that first batch, but we needed higher fidelity to know whether any could work. At this point, Daniel took over. He refined the best sketches and created five distinct directions. Keep in mind that none of these were final — we planned to hire a professional illustrator once we zeroed in on the right concept.

The cover

I loved the illusion of motion and depth created by the arrows… but at the same time, it’s not crystal clear what the arrows mean. They could be on the cover of almost any business book. Similarly, the text-only covers have a refreshing clarity. But they also lack a clear message or personality.

We decided on the stopwatch. It was solid. The tomato red was eye-catching. It conveyed the ideas of “speed” and “five days” without forcing the viewer to think too hard.

But a few weeks later, we had second thoughts. The stopwatch looked a little derivative, and the personality was wrong. A stopwatch is intense. We think Sprint is a fun and approachable book—and we wanted that personality to shine through.

At a meeting in October, our editor Ben Loehnen encouraged us to give it one more shot. “You’ll have to live with this cover for a long time. You should love it.”

Braden’s sketch

Just a few minutes later, I sat with Ben and our agent Sylvie Greenberg, flipping through old cover designs, hoping to spark an idea.

Meanwhile, Braden sat at the other end of the table, quietly doodling. Braden does this all the time—he goes to the side of the room, works in silence, and comes up with something amazing.

This was no exception. Here’s what Braden sketched:

It was the word “sprint”, progressing from a roughly-sketched S to a polished, three-dimensional T. It perfectly captured the book: You start with a problem on Monday, and end with a tested prototype on Friday. We knew instantly that this was the winning idea.

The next day, Braden put together a rough cover mockup:

We were even more convinced this was the right direction. Now it was time to find our illustrator.

Jessica Hische saves the day

As luck would have it, Daniel is friends with design superstar Jessica Hische. Jessica is an awesome illustrator and letterer. Her impressive projects include the cover for Dave Eggers’ The Circle and the titles for Wes Anderson’s Moonrise Kingdom.

We met with Jessica and showed her the concept mockup. We also explained that our exploratory work had burned nearly all of the time before publication. We only had a couple of weeks to get it done. Jessica told us not to worry.

Jessica started on paper. Here are a couple of her preliminary sketches for Sprint:

Already amazing, right? Next, she created a round of quick, full color designs, exploring a few different directions:

We loved the progression from sketch to finished in the first two designs. But there was also something really great about that last one, with the slanted letters. As Jessica put it:

I think if we did something for the word “sprint” to logoify it, this would be an interesting one. Right now it feels a little Soviet with the red and yellow, so we’d need to talk color.

For the next round, she did just that: turning “sprint” into a logo and refining the type. Jessica decided that Freight Sans Condensed matched the personality of the book. She had to redraw the letters to correct for the slant, but by starting with type, she was able to do lots of iterations very quickly.

Here’s what she ended up with:

Just like that, in a matter of days, Jessica had done what we’d been trying to do for months. That was the cover. All we had to do was choose a color:

You can’t judge a book by its cover, of course. But we really love this cover. And we learned a very important lesson: The next time any of us writes a book, we’re going straight to Jessica.

Sprint is a book about surprising ideas: that the biggest challenges require less time, not more; that individuals produce better solutions than teams; and that you can test anything in one week by building a realistic façade.

We wrote Sprint to be a practical guide for teams of any size, from small startups to Fortune 100s, from teachers to nonprofits. You can order it on Amazon or see more ways to buy.