As a veteran of several high-powered organizations — including McKinsey, Google, Dropbox — Notion advisor Olivia Nottebohm has learned the importance of respecting her teams’ personal journeys. She believes none of the 10 most important milestones in any person’s life will be career-related, and it’s important for leaders like her to strike a balance between accountability and empathy. “Before I need to have a tough conversation,” she says, “I try to put myself in their situation and think, ‘OK, how would I best receive something? ... [And] how is this person different from me?’”

In this episode, Olivia and Joubin discuss immigrant assimilation, the joy of learning, college vs. startups, stepping away from work, growth vs. profits vs. product, steep learning curves, working through a restructuring, collaborative creativity, what CEOs care about, community-led growth, screening for Grit, finding focus, and the only things people will remember about us when we’re gone.

In this episode, we cover:

• Olivia’s parents and how she became a grammar stickler (01:00)
• Small-town ice hockey and playing with the boys (03:54)
• Why her parents didn’t want Olivia to go to Harvard, and what she wants for her own kids (08:49)
• Choosing to go into business instead of science (15:32)
• What changed for Olivia when her brother passed away unexpectedly (18:42)
• “Grow Fast or Die Slow” (24:29)
• Who doesn’t believe in growth in 2022? (31:37)
• Leaving McKinsey after making partner (35:32)
• Six years at Google and one year at Dropbox — starting right before COVID (39:34)
• How Olivia got to Notion, the crowded “all-in-one” space, and its enormous addressable market (42:36)
• The evolution of go-to-market strategies (49:43)
• Accountability, empathy, and the biggest milestones in everyone’s life (58:36)

Links:

• Connect with Olivia
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm