COO of Headspace: Why You Should Re-Recruit Yourself
Best Manager Ever · Annie Riley
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Show Notes
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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