Divot #19: Leading with Curiosity, Building Culture, and Finding Joy at Work
Work is changing fast, but how do you build cultures and teams that thrive through it?
In this episode, Anne Raimondi, COO and Head of Business at Asana, shares lessons from two decades leading fast-growth companies like Zendesk, SurveyMonkey, and TaskRabbit, serving on boards including Gusto and Patreon, and teaching leadership at Stanford GSB.
She opens up about growing up as the child of immigrants, why curiosity became her leadership superpower, and how she balances ambition with humility. You'll hear her talk about building resilient culture, using humor in high-pressure rooms, navigating perfectionism, and bringing AI into teams with trust and clarity.
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Timestamps:
0:00 - From San Jose roots to Asana's COO
1:13 - Childhood lessons from immigrant parents
2:21 - Seeing herself as a problem solver
2:46 - Curiosity as a leadership superpower
4:12 - Building advocacy with customers and employees
5:15 - Staying lighthearted in high-pressure rooms
7:19 - Using humor and honesty to diffuse tension
9:03 - Leading without yelling: turning up the right "dials"
11:04 - Rallying teams around the customer's voice
13:03 - What makes someone have outsized impact
14:34 - Healthy ambition vs. territorial behavior
17:24 - Why fun and joy matter at work
18:26 - Defining culture: mission + values + norms
20:17 - How to evaluate a company's culture
23:01 - Can you change culture or must you choose it?
24:34 - Leadership training and conscious leadership at Asana
26:07 - Serving on boards: how she got her first seat
29:07 - How board work makes you a better operator
33:49 - Why she wanted to be in the boardroom
33:57 - On being a "recovering perfectionist"
34:54 - Balancing family, career, and letting go of perfection
35:57 - What her kids might say about her work
39:45 - Privilege, gratitude, and immigrant perspective
39:45 - AI's impact on how teams are built
42:02 - How to bring AI into a resistant culture
43:19 - Asana's "AI first" approach
46:07 - The leader she most admires
48:16 - The one idea she'd implant in everyone's mind
49:08 - Hardest accomplishment: 30-year marriage
50:20 - Her best advice on resilience and bouncing back
50:55 - What she's most proud of in her career
52:02 - The measure of a life well lived
53:11 - The impact she hopes to leave on the world
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Hashtags:
#DivotPodcast #Leadership #Culture #Curiosity #JoyAtWork #Asana #Entrepreneurship #Resilience #TeamBuilding #AI