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

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 — Brought to you by Brave Search API—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 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/ 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.

Lenny RachitskyhostPaige Costelloguest
Jul 8, 20231h 3mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Paige Costello on trust, coaching PMs, and smarter product strategy

  1. Paige Costello, product lead at Asana, shares how she builds trust and credibility as a relatively young leader by deeply understanding customers, markets, and metrics, and by showing up with unique insight instead of pretending to know everything.
  2. She explains Asana’s evolving product development and planning processes—nested metrics, area-based ownership, rolling 12‑month plans, and the Double Diamond framework—and how these changes improved focus, autonomy, and speed.
  3. Paige dives into her approach to mentoring PMs through leading by example, exposure over instruction, and concrete tools like better feedback frameworks and clearer decision ownership.
  4. Throughout, she highlights common PM pitfalls, mindsets that accelerate growth, and practical techniques for confidence, handling trade-offs, and integrating AI and LLMs into product work.

IDEAS WORTH REMEMBERING

5 ideas

Bring unique insight to build trust, regardless of your seniority.

Paige emphasizes that younger PMs win over skeptics by deeply knowing the customer, product, numbers, and competitive landscape—showing up with real insight rather than trying to out-expert functional veterans.

Plan at multiple altitudes with rolling horizons, not rigid annual roadmaps.

Asana moved to nested metrics (R&D → pillar → area → team) and rolling 12‑month plans updated every six months, which aligns product and go-to-market while admitting that priorities will change.

Use the Double Diamond to force real discovery, not opinion-driven solutions.

By explicitly broadening and narrowing on customer, problem, and solution—and mapping reviews (kickoff, concept, spec, full experience, launch) to those phases—teams escape knee-jerk feature thinking and stay customer-targeted.

Coach by example and exposure, not just instructions.

Paige intentionally runs meetings the way she wants others to run them and brings PMs into high-stakes situations so they can learn through exposure (seeing how it’s done) alongside education and direct experience.

Shift from advocacy to inquiry to grow faster as a PM.

New PMs often feel compelled to be the expert and defend a fully-baked plan; Paige advises instead to be truly curious, invite challenge, and co-develop solutions, which leads to better outcomes and stronger relationships.

WORDS WORTH SAVING

5 quotes

Bring the insight. Know thy customer, know thy market, know thy competitors, know thy numbers, know thy product.

— Paige Costello

Think big, ship small.

— Paige Costello

Trust is equal to credibility plus reliability plus authenticity, divided by perception of self-interest.

— Paige Costello (referencing Anne Raimondi’s framework)

Always answer the question they should have asked.

— Paige Costello (advice from an Intuit business unit leader)

Sometimes your brain is so accustomed to having a scarcity mindset. The moment I asked myself, ‘How might the opposite be true?’ my shoulders dropped.

— Paige Costello

Building trust and credibility as a younger or less-experienced leaderAsana’s product planning structure, metrics, and Double Diamond processHybrid work, office culture, and collaboration dynamics at AsanaCoaching and developing product managers (experience, exposure, education)Mindsets for confidence, curiosity, and challenging scarcity thinkingIntegrating AI/LLMs into an existing product and org structureCareer management: learning curve, environment, and problem selection

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