How to ask the right questions, project confidence, and win over skeptics

Paige Costello, Head of Product for the core, desktop, web, and mobile apps at Asana (previously at Intuit), discusses how Asana's product planning and development process has evolved. The conversation covers planning cadence, the Double Diamond process, hybrid work, building trust with skeptics, coaching, AI experimentation, and career thinking.

01Key learnings

• Plan on a rolling 12-month horizon, refreshed every six months, so the immediate half has higher confidence and the business stays aligned with go-to-market.
• Structure planning in nested altitudes (company, pillar, area, team) with metrics at each level so every team knows the outcome it drives.
• Use a broad-then-narrow process for each problem: choose the customer, then the problem, then the solution, and pick success metrics tied to outcomes rather than feature usage.
• To earn trust with skeptics, bring insight: know your customers, market, competitors, numbers, and product well enough to make a point of view credible.
• Cap approvals on a piece of work to a small number of reviewers with one accountable decision-maker, so work keeps moving and agency stays close to teams.
• When giving feedback, describe the situation, behavior, and impact so the feedback is a subjective observation that opens a conversation rather than a verdict.
• Ask 'How might the opposite be true?' when you feel trapped by scarcity, as it often reveals alternatives and relieves pressure.
• Assess a role by its learning curve, supportive environment, and whether the problem is interesting, and focus on skills and experiences rather than titles.

02Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.