My afternoon with Dropbox New York

Warren Challenger
3 min readJun 10, 2017


As part of the 99u experience, every attendee has the opportunity to attend two workshops — my second was with Dropbox New York.

Who are Dropbox?

Dropbox was originally founded in 2007, by Drew Houston and Arash Ferdowsi. Dropbox started life with initial funds from seed accelerator Y Combinator and began it’s journey as a digital storage platform. Today with offices worldwide and a blossoming portfolio of products, Dropbox has grown into much more than the documents folder that appeared on every single one of your desktops.

Transparent Teams: Driving Alignment Through an Open Creative Process

One of the most important steps in the creative process is feedback or crit. The earlier you get feedback the better your product or design will be. You’ll also get buy in from the very start, making the journey for both you and your stakeholder much easier.

Hosted by Aaron Robbs, Brand Studio Creative Director & Collin Whitehead, Head of Brand Studio.

Dropbox Paper — The Dropbox answer to transparency within teams

The afternoon was spent talking about the Dropbox creative process and challenges on keeping an open forum for feedback across many teams, office locations and time zones. With a dash of self promotion, some of the key takeaways were:

  • Collaboration is hard, but it’s worth the effort. Silos are not an option for an excellent creative process.
  • The workforce is changing. With over 30% of creatives now being freelance or self employed.
  • Transparency can suck but embrace it anyway. Your projects will be better for it.
  • Make sure your working environment is a safe place for creatives to do their best work and not feel they can’t speak up or make mistakes.
  • Creatives need time and space to create their best work.
  • Design or agree your creative process before starting the creative.
  • Open communication always.
Dropbox Paper — Collaboration Tool
  • Feedback early and often. Sharing becomes less scary the earlier you invite others to collaborate.
  • When working with external agencies or studios, integrate that team and work as one.
  • Show all work to stakeholders during the feedback process, even the ideas that didn’t make the cut.
  • Show your math and thinking with any creative piece. Verbalise your design decisions. Retain a level of objectivity, there are reasons why this idea hits the brief and why this other idea doesn’t.
  • Perform retro’s, asking questions such as: What happened right or wrong? Any lessons for the future?
  • Document your retro, never verbal only.
  • Dropbox share there retro’s with the whole company globally. So everybody can learn from paths already walked.
  • Be mindful to sweat the right details and not all the details, when dealing with large projects or many iterations.

If you’d like to learn more about 99u and are thinking of attending next year please visit their website. If you’re a creative always looking to learn and push yourself, I couldn’t recommend attending enough.

Further Reading

My first workshop at 99u 2017 was at the ustwo New York office “Designing Across the Client Spectrum”. Click here to read more about that session.

My first 99u 2017 afternoon session was with ustwo New York