CEO Ian Small Was Told He “Needs to Learn to Listen Better”

CEO Ian Small Was Told He “Needs to Learn to Listen Better”


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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?

Scroll down to find:

  • Video of the episode
  • Quotes
  • How to subscribe
  • Full transcript

Find Ian on social media:

Watch the Full Episode:


"My first five annual performance reviews that I received as an engineer in Silicon Valley every year would start the same way: 'Ian needs to learn to listen better.'"
"I wouldn't be in the role that I am in now, and I wouldn't have access to the roles that have defined my career over the last 10 to 15 years, if I hadn't learned to overcome this."
"Learn to dismiss nothing. That's actually very, very hard to do... [pattern matching] is a negative where you can dismiss things really quickly, because they seem to match a pattern that you think is applicable, and then you stop listening."

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Automated Transcript (Likely Contains Mistakes)

Mark Graban is an internationally-recognized consultant, author, and professional speaker who has worked in healthcare, manufacturing, and startups. His latest book is Measures of Success: React Less, Lead Better, Improve More. He is author of the Shingo Award-winning books Lean Hospitals and Healthcare Kaizen, as well as The Executive Guide to Healthcare Kaizen. He also published the anthology Practicing Lean that benefits the Louise H. Batz Patient Safety Foundation, where Mark is a board member. Mark is also a Senior Advisor to the technology company KaiNexus. He is also a Senior Advisor and Director of Strategic Marketing with the healthcare advisory firm, Value Capture.