Making Fun of the Enterprise

Chris Butler
Philosophie is Thinking
6 min readJun 7, 2017

This year, Philosophie is sponsoring Enterprise UX, and we wanted to share a little love with the brave designers and product managers that are trying to make enterprise software more humane. We considered what kind of swag would make sense — surely the attendees have enough pens, mousepads, t-shirts, and other swagbag stuffers. How could we leave them with something useful?

If you know Philosophie, you know that we’re about breaking down the usual barriers that prevent good ideas from getting executed. You also know that we have fun while doing that. So that’s how we framed our swag problem: how do we make the enterprise design environment more fun?

Personally, I’ve been experimenting a lot with the idea of introducing randomization into design explorations. Looking at all of the brainstorming and creativity tools on my desk, it struck me that we could apply an element of randomness to one of our favorite collaborative design methods: the Design Studio.

If you’re not familiar with Design Studio, check out this classic talk by Todd Zaki Warfel. To summarize, you bring together a diverse group of people to work together to solve a problem. First, the group engages in divergent thinking, generating as many distinct solutions very quickly. After presenting and discussing the possibilities, the group works together to converge to the best solution to move forward with.

We love this method because it helps give some structure to creative ideation and decision-making, helping to avoid the usual pitfalls of “brainstorming” sessions.

Designing the game

I pitched the idea to our CEO Skot Carruth and within minutes we were running with the concept. As a small organization, we had the usual constraints: very little money, no one dedicated to the project, and only a couple weeks before they had to go to the printer.

We started by sketching concepts in order to visualize the form the game might take. We knew that we wanted to incorporate randomness and time-boxing, so we were drawn to solutions that accomplished both without the need for custom game pieces.

Using Design Studio to improve the design of Design Studio.
Tiny minute timers were tried first

We settled on using dice for the element of randomness, and decided to try sand timers for the timing. We realized they could also serve as the gamepiece that players would move along the board.

The rough format seemed doable. We had minimized the cost and lead time for the components, but next we needed the most important part: the content!

As you can see in the photo to the left, I keep a deck of Oblique Strategies nearby at all times. What makes Oblique Strategies such a powerful creativity tool is that it takes your current understanding of the problem and expands it based on the random card you draw from the deck. This is what we shoot for when we practice divergent brainstorming, so we generated a number of our own prompts that we thought could have a similar effect:

As a bit of an easter egg, we included some of our company’s core values. Can you guess which ones they are?

We needed to also think about the converge part of the game. How might we help a group of people drive toward consensus? Generally, we use different voting or prioritization techniques in our client practice, but we select the method based on the project’s circumstances. How might we provide useful guidance when we don’t know those circumstances? Furthermore, how do we incorporate the spirit of randomization?

We’re still not sure! We decided to incorporate a variety of prompt types for our MVP. Many of the options aim to spark conversation through a particular lens, such as “how would marketing prefer it?” or “what can we ship next week?” Others ask people to rank ideas or vote based on some criteria, such as “which idea is the bravest?” or “prioritize based on simplicity.”

As we were experimenting with the content, Brooke Kao started turning our rough sketches into digital layouts. Her original inspiration was classic boardgames like Monopoly. Skot Carruth and Keaton Herzer pushed the design even further.

Design Prototypes

Since we’re all about rapid design experimentation, we decided to make the board in the shape of the speed pixel, the beloved oblique square that serves as a building block to our identity design system.

Play Testing

We weren’t going to ship this without testing it. Fortunately, we’re in the design business so we had a few opportunities to use it, gather feedback, and tweak it before shipping to the printer.

Hijacking the designer roundup to play test

Printing and Packaging

Our Community Manager Jessica Ramos coordinated printing, shipping, and ordering the game pieces. As the final designs went to press, we experimented with different forms of packaging. We evaluated three options: a traditional box, rolling the board up into a cardboard tube, or simply putting it in a plastic bag.

The simplest option proved the best for the first version of the game. When I mentioned it reminded me of shareware back in the day, I got the equivalent of blank stares… you know what I mean right?!

Yes, software used to be sold this way in shops. I know, shops.

Everything got shipped to our San Francisco office where Skot Carruth, a task rabbit, and Chris Meono assembled the parts with the help of good music and a bit of wine. Here’s the final product boxed up and ready to be shipped to the conference organizers:

Ship it!

:shipit:

Like a lot of projects we take on at Philosophie this one was executed swiftly and with a tremendous amount of collaboration. It’s still just an MVP, but the only way we can make it better is by putting it out there and listening to the people who use it.

We hope you enjoy the game and find it useful. If you’re not fortunate enough to be attending the conference, we’re still happy to send you a copy of the game, just contact me.

Philosophie is a digital innovation firm with offices in San Francisco, Los Angeles, and New York City. We help large organizations validate and develop their promising ideas through agile design, rapid prototyping, and software craftsmanship. Whether it’s to reduce costs, explore emerging markets, or improve the customer experience, we apply a startup mentality and toolset to deliver meaningful progress faster than you think is possible.

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Philosophie is Thinking
Philosophie is Thinking

Published in Philosophie is Thinking

Thoughts from the ridiculously talented inventors and makers at Philosophie, a digital product consultancy in Los Angeles and New York. Learn more at: http://philosophie.is

Chris Butler
Chris Butler