Lenny's Podcast: Product | Growth | Career

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

Jul 9, 2023

Paige Costello, Head of Core Product at Asana, previously led teams at Intercom and Intuit. She shares insights on Asana's unique product development approach and the evolution of teamwork within tech. Paige emphasizes the double-diamond framework, the value of curiosity and openness in product management, and the importance of authentic communication in building trust. She also highlights strategies for effective feedback using impact statements, along with the significance of mentorship in personal and professional growth.

01:03:20

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Episode guests

Paige Costello

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Quick takeaways

To build trust with skeptics, new PMs should challenge assumptions, be open, ask good questions, and embrace feedback.

Coaching product managers requires leading by example, creating a safe space, and providing guidance without being too prescriptive.

At Asana, the product development process has evolved to a six-month rolling planning cycle using the double diamond framework for thorough exploration and effective decision-making.

Deep dives

Bringing Insight and Curiosity to Win Trust and Overcome Skepticism

When trying to garner trust and win over skeptics, it is important to bring insight and knowledge to the table. Understanding the customer, market, competitors, numbers, and product is crucial. New PMs can get held back by a scarcity mindset and the belief that they must have all the answers. By challenging assumptions and adopting a mindset of curiosity, they can build trust and be open to different possibilities. Building trust is also about being authentic, vulnerable, and showing a genuine interest in learning and understanding. By being open, asking good questions, and embracing feedback, new PMs can navigate skeptics and build trust.

bring the insight to lead

02:40

The Importance of Experience

03:51

The Importance of Authenticity and Transparency in Leadership

02:53

The Double Diamond Process: Going Broad and Narrow in Product Thinking

01:44

Intro

4min

Navigating Teamwork in Product Management

13min

Navigating Hybrid Work Dynamics

5min

Building Trust Through Leadership and Communication

7min

Leading by Example: The Power of Mentorship and the Three E's Framework

3min

Navigating Effective Meeting Management

26min

Chatbot Innovations and Team Productivity

6min

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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’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

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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:

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

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