How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit)

Published: July 9, 2023, 12:01 p.m.

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Paige Costello is a beloved product leader with a reputation as a remarkable coach and mentor. She is currently the Head of Core Product at Asana, where she leads the group responsible for Asana\u2019s web, desktop, and mobile apps. Prior to that role, she served as the Director of Product at Intercom and, before that, as a Group PM at Intuit, where she kickstarted her product career through their renowned APM program. In today\u2019s episode, we discuss:

\u2022 The unique product development process at Asana and how it\u2019s evolved

\u2022 The double-diamond framework

\u2022 Conscious leadership training, and why every Asana employee learns it

\u2022 How to demonstrate confidence and earn trust from skeptics

\u2022 Why curiosity and openness may be the most important PM competencies

\u2022 How to give feedback using impact statements

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Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-ask-the-right-questions-project

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Where to find Paige Costello:

\u2022 Twitter: https://twitter.com/paigenow

\u2022 LinkedIn: https://www.linkedin.com/in/paigecostello/

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Where to find Lenny:

\u2022 Newsletter: https://www.lennysnewsletter.com

\u2022 Twitter: https://twitter.com/lennysan

\u2022 LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Paige\u2019s background

(04:38) What Paige is responsible for at Asana

(06:04) The evolution of Asana\u2019s product development process

(09:10) Planning frequency

(11:26) Examples of areas and metric tracking at Asana

(12:46) The double-diamond process and how it\u2019s applied at Asana

(16:53) Asana\u2019s office-centric hybrid work culture and the future of WFH

(21:45) How to garner trust and win over skeptics

(24:45) Why you should befriend researchers

(26:17) How to exude confidence

(29:03) The 3Es framework

(33:43) Advice for early-career PMs

(38:43) Paige\u2019s latest pillars strategy

(40:05) AI at Asana

(41:50) Lessons from Paige\u2019s time at Intuit

(45:53) Challenges new PMs face

(48:55) Challenges Paige has faced in her career

(52:39) Paige\u2019s skill-focused career philosophy

(55:43) Lightning round

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Referenced:

\u2022 Use This Equation to Determine, Diagnose, and Repair Trust: https://review.firstround.com/use-this-equation-to-determine-diagnose-and-repair-trust

\u2022 About conscious leadership at Asana: https://wavelength.asana.com/workstyle-simple-shift/

\u2022 The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable/dp/0990976904

\u2022 Intuit: https://www.intuit.com/

\u2022 Inspired: How to Create Tech Products Customers Love: https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507

\u2022 The Blind Assassin: https://www.amazon.com/Blind-Assassin-Novel-Margaret-Atwood/dp/0385720955

\u2022 The Alchemist: https://www.amazon.com/Alchemist-Paulo-Coelho/dp/0062315005

\u2022 The Diplomat on Netflix: https://www.netflix.com/title/81288983

\u2022 Fire of Love on Disney+: https://www.disneyplus.com/movies/fire-of-love/1hC7erRfsl3B

\u2022 Poe: https://poe.com/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.



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