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

Brought to you by Brave—An independent, global search index you can use to power your search or AI app | Attio—The powerful, flexible CRM for fast-growing startups | Round—The private network built by tech leaders for tech leaders

—

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’s 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’s episode, we discuss:

• The unique product development process at Asana and how it’s evolved

• The double-diamond framework

• Conscious leadership training, and why every Asana employee learns it

• How to demonstrate confidence and earn trust from skeptics

• Why curiosity and openness may be the most important PM competencies

• How to give feedback using impact statements

Listen now on Apple, Spotify, Google, Overcast, and YouTube.

Find the transcript for this episode and all past episodes at: https://www.lennyspodcast.com/episodes/. Today’s transcript will be live by 8 a.m. PT.

Where to find Paige Costello:

• Twitter: https://twitter.com/paigenow

• LinkedIn: https://www.linkedin.com/in/paigecostello/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• Twitter: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Paige’s background

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

(06:04) The evolution of Asana’s 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’s applied at Asana

(16:53) Asana’s 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’s latest pillars strategy

(40:05) AI at Asana

(41:50) Lessons from Paige’s time at Intuit

(45:53) Challenges new PMs face

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

(52:39) Paige’s skill-focused career philosophy

(55:43) Lightning round

Referenced:

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

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

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

• Intuit: https://www.intuit.com/

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

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

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

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

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

• Poe: https://poe.com/

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

Lenny may be an investor in the companies discussed.