May 12 / 41 min

Atlassian’s Stephen Deasy: How designers and engineers unite the possible with the probable

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Stephen Deasy

Stephen Deasy

Head of Cloud Engineering, Atlassian
About The Episode

“Designers are about possibilities. Engineers are about probabilities.” This quote, from Stephen Deasy, Head of Cloud Engineering at Atlassian, is just one example of how concisely he can describe the relationship between designers and engineers. 

Our interview with him was our first chance to learn from a leader on the engineering side, and he shared a wealth of knowledge that will help designers work more effectively with their engineering counterparts.

Stephen gave us insights about running regular retrospectives and health monitors with your team, and “plays” like Roles and Responsibilities. He also spoke to the mindset and process shift that occurs when teams scale from 15, to 50, to 150 people. Stephen also relayed some great insights on design and agile.


  • How to look across a company to get a pulse on the health of teams 
  • Understanding the mindset shift as teams scale
  • What it looks like when teams are efficient and productive in an agile environment


Stephen Deasy is an experienced engineering leader helping teams, systems, and companies scale. He’s built and led teams all over the world build products that users love, from his current role at Atlassian to Groupon and VMWare.

He’s spoken at events like Atlassian Summit, VMware’s VMworld, OpenView’s Product Led Growth event, as well as published papers and filed seven patents.

Meet Your Hosts

Aarron Walter
VP of Design Education

Aarron Walter is Director of Product on the COVID Response team at Resolve to Save Lives. Previously, he was VP of Design Education at InVision, and founded the UX practice at Mailchimp where he helped grow the product from a few thousand users to more than 10 million. He’s the author of a number of books, the latest of which is a second edition of Designing for Emotion. Aarron’s design guidance has helped the White House, the US Department of State, and dozens of major corporations, startups, and venture capital firms.

You can find Aarron on Twitter and LinkedIn.

Eli Woolery
Director of Design Education

Eli is the Director of Design Education at InVision. His design career spans both physical and digital products, and he has worked with companies ranging from startups (his own and others) to Fortune 500 companies.

In addition to his background in product and industrial design, he has been a professional photographer and filmmaker. He teaches the senior capstone class Implementation to undergraduate Product Designers at Stanford University. You can find Eli on Twitter and Medium.

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