COO of Headspace: Why You Should Re-Recruit Yourself

COO of Headspace: Why You Should Re-Recruit Yourself

What does it take to lead through 15 years of pivots, mergers, layoffs, and massive growth— without losing your people (or your mind!) along the way? Annie Riley sits down with Karan Singh, co-founder of Ginger and COO of Headspace, to unpack why great managers win people over through curiosity and genuine connection, how managers need to learn to ride the “J-curve” of change, and why everyone should re-recruit themselves to their role.


Timestamps:

00:00 Meet Karan Singh

04:30 Learning to manage on the fly

07:20 Winning people over

09:25 The mindset for surviving startup chaos

12:01 The j-curve of change

14:41 Speed vs. Space: giving teams time to process change

18:32 Healthy departures

22:24 Creating a “Next Play Plan”

26:49 Why you should re-recruit yourself

38:52 Rethinking PIPs: What most people get wrong


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