My Favorite Mistake — 178: Why CEO Ian Small “Needs to Listen Better” and How He Learned to Do So

CEO of Evernote

Episode page with video, transcript, and more

My guest for Episode #178 of the My Favorite Mistake podcast is Ian Small, CEO at Evernote, the app that launched a personal productivity movement for knowledge workers around the world. Under Ian’s leadership (since 2018), Evernote found the courage to go back to basics, launching a new era of innovation for the company and building upon a decade of growth.

Ian brings more than 25 years of global product, technology, and business leadership experience to his current role. Trained as an engineer, Ian’s career has evolved from designing and building user experiences at Apple into product leadership and large-scale business management as CEO of TokBox and global Chief Data Officer for Telefónica SA.

In addition to his current role at Evernote, Ian sits on the board of directors for Lumentum and is an advisory board member for Alphabet subsidiary Loon (a graduate of Google’s X Lab).

He holds a Master’s degree in Computer Science, a BASc in Engineering Science from the University of Toronto, and has earned more than 10 patents.

In this episode, Ian tells his favorite mistake story about being told, early in his career, that he needed to be a better listener. What were the consequences as he became a manager? How did he realize that he needed to change and how did he work to overcome that bad habit to the point that he can now coach younger leaders to avoid or get out of this same trap? And how did Ian learn to listen better to customers and employees alike?

We also talk about questions and topics including:

  • Your favorite patent?
  • Having to change habits… how?
  • “Listen with a beginner’s mind “ Marc Benioff – Salesforce
  • The episode with Emily Learing
  • Overhauling Evernote over 2 years — rebuilt from scratch?
  • Better listening to customers, employees, and the board/investors
  • Everybody internally (and customers) could tell you what the problem — why wasn’t it being addressed?
  • Was Evernote not listening or not taking action?
  • The mistake of inaction vs. action?
  • What do you think of the SV mantra “fail fast, fail often”?
  • How to avoid needing another reboot in 2030?
  • Mistakes in how users use Evernote or is that not possible?

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