Lenny's Podcast: Product | Career | Growth

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

July 9, 2023

AI Summary

5 min read

Paige Costello, head of Asana's core product pillar covering desktop, web, and mobile apps, discusses evolving product processes at scale, leadership tactics for gaining trust, and practical advice for PMs amid rapid tech changes like AI.

Product organization and planning shifts
Asana structures product around pillars (e.g., core clarity features like goals, portfolios, projects), areas (e.g., "Coordinate" for team collaboration on tasks/projects, tracking metrics like org paying weekly active users and healthy project use), and teams, each with nested metrics for accountability. Planning has shifted from annual cycles organized by projects/locations to six-month updates for a rolling 12-month horizon, enabling quicker pivots to new opportunities or tech while aligning with go-to-market. Roadmaps emphasize problems over features, with prototyping encouraged and explicit allowance to cut or pivot post-roadmap.

Continue reading the full summary in the app — free to try.

Read Full Summary →

Free • No credit card required

Listen to Audio Summary Open in App

What you'll learn

1 `* (04:38) **Asana Role and Core Product Focus**`
2 `* (06:04) **Evolution of Asana's Product Development Process**`
3 `* (12:46) **Double Diamond Product Process**`
4 `* (17:27) **Hybrid Work Policy and Office Dynamics**`
5 `* (21:45) **Building Trust as Youngest Leader**`
6 `* (26:36) **Projecting Confidence and Career Growth (3 Es)**`
7 `* (33:43) **Key Advice and Conscious Leadership Mindset**`

+ Full timestamped outline available in the app

Show Notes

Brought to you by Brave—The 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

—

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

—

Where to find Paige Costello:

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

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