Dropbox executive Dean Swan on why the modern way of working is broken

My guest on today’s show is Dean Swan. Dean is the Country Manager of Dropbox, where he oversees Dropbox’s business operations across Australia and New Zealand. And in case you haven’t heard of Dropbox, it’s one of Silicon Valley’s unicorns, which is a company valued at over $1 billion. Dropbox provides file hosting and I’ve been a customer of Dropbox for many years.

I connected with Dean as Dropbox Australia has been experimenting with how they work and challenging a lot of the working norms that exist. This has resulted in the launch of Dropbox’s ‘Enlightened Summer’, which is a summer-long initiative encouraging workplaces across Australia to reimagine a more enlightened way of working.

In my chat with Dean, we start by talking about how Dropboxers have changed their approach to work, and we then delve into how Dean has adapted his own working behaviours too. And if you like the sound of what Dropbox is doing, I finish my chat with Dean talking about advice he has for listeners who are trying to influence their boss on changing the working norms.

More specifically, we cover:
  • Dropbox’s Enlightened Summer campaign
  • How Hack Week’s work at Dropbox
  • The range of productivity techniques that Dropbox Australia have been trialling
  • Why Dean moved the Dropbox office to the Bondi Surf Life Saving club for a day
  • Why Dean had to unlearn everything he learned in his corporate life at Microsoft when he moved to being a start-up founder
  • How being a chef helped Dean think about how he manages his energy during the day
  • How Dean uses his runs for problem solving
  • How Dean combined Manager and Maker time when he moved to Dropbox as head of sales for Asia-Pac
  • Dean’s ideal weekly schedule
  • How Dean uses walking meetings to change energy levels
  • The importance of retrospectives at Dropbox
  • Tips on how to convince your boss that the current way of working is broken and that change needs to happen.

Find out more about Dropbox’s Enlightened Summer campaign and download the toolkit.