Building trust, confidence, and coaching skills as a product leader

Executive overview

New PMs often default to advocacy over inquiry — projecting false certainty instead of bringing genuine customer insight. The leaders who win over skeptics and experienced peers do so by knowing the customer, the market, and the numbers better than anyone else in the room.

Paige Costello, product lead at Asana, shares frameworks for building trust, coaching PMs, and evolving product development processes at scale.

Credibility comes from insight, not authority — know thy customer, know thy market, know thy numbers.

Asana's product development process

• Planning moved from annual to rolling 6-month cycles covering 12 months: higher confidence in the near half, lower in the far half.
• Structure nested into pillars, areas, and working teams — each area has a specific target customer, problem space, and one or two key metrics.
• The double diamond process maps reviews to inflection points: kickoff → customer and direction selection → design concept review → product spec → full experience review → launch.
• Going broad then narrow forces teams out of opinion-driven thinking and into systematic customer discovery.
• Reviews are async-first; meetings called only when unresolved questions remain.
• No more than three reviews per piece of work; one person is the blocker at each stage.
• Meeting size capped at 10; beyond that, the host removes excess attendees and writes better decision notes.
• AI/LLM exploration was staffed as a dedicated prototype team to move fast outside the standard double diamond — then findings handed to domain teams.

Winning over skeptics and building trust

• Bring the insight: watch customers use the product firsthand, know competitors, market, and numbers.
• Trust equation: credibility + reliability + authenticity, divided by perceived self-interest.
• Credibility tips the scales fastest when you're unknown — insight you've earned is the shortcut.
• When joining a new role, become close with a researcher immediately and get direct customer observation time.
• Dog-fooding cultures create a risk: teams stop seeing what real customers actually need.

Communicating confidence

• Speak before you feel fully ready; ask for forgiveness and be vulnerable.
• Real confidence is conveyed by asking questions and admitting uncertainty — not by asserting answers.
• Body language matters: make eye contact, be physically present, scan the room for questions.
• In meetings: clear agenda, move quickly, leave space for debate, close with "did I get all of that?"

Coaching and leading by example

• Three E's framework: experience, exposure, and education — exposure is the most underused lever for growth.
• Run the kind of meetings you want others to run; your style becomes the template.
• Write post-its of what you want to say; wait to see if someone else says it first — police your own micromanagement.
• "Always answer the question they should have asked" — surface the bigger picture, not just the literal query.

What holds new PMs back

• Believing they must be the expert — leads to doing discovery in isolation and showing up with closed thinking.
• Performative collaboration: running reviews while privately rejecting all feedback.
• Career-anxiety-driven behaviour: focus on the work and outcomes; promotions follow from connection to the work.
• Inquiry beats advocacy — ask the question behind the question; categorise feedback as must/should/consider.

Career advice and personal frameworks

• Don't self-select out: don't disqualify yourself before applying or raising your hand.
• Think big, ship small: avoid incremental thinking caused by over-optimising near-term metrics.
• Above or below the line (Conscious Leadership Group): above = open, curious, committed to learning; below = committed to being right; recognise which state you're in before making decisions.
• How might the opposite be true? — a single question that breaks scarcity thinking and reveals false trade-offs.
• Evaluate career health on three dimensions: steepness of learning curve, quality of environment, interest in the problem being solved.
• Think in terms of skills and experiences to acquire, not roles or companies to target.

Giving feedback

• Situation → Behavior → Impact format: grounds feedback in observable events, not judgement.
• Keeps feedback subjective and experiential — "this is what I experienced" — making it harder to dismiss.
• Enables a next-steps conversation instead of a debate about facts.

Asana pro tip

• Use multi-assign on subtasks to send pre-reads with due dates to a whole team in one step.
• Take meeting notes live in a task; highlight action items and convert them to subtasks immediately.