Paige Costello on Asana's Product Process, the Double Diamond, and Coaching PMs

Paige Costello on Asana's Product Process, the Double Diamond, and Coaching PMs

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Paige Costello on Asana’s Product Process, the Double Diamond, and Coaching PMs

Source: Lenny’s Podcast Speaker: Paige Costello Date: ~2023 Link: https://www.lennysnewsletter.com

Key ideas

  • The Double Diamond maps divergence and convergence to product artefacts. Asana uses the Double Diamond to sequence discovery work: broad customer selection → narrow to target customer → broad problem exploration → narrow to core problem → broad solution ideation → narrow to spec → launch. Each inflection point corresponds to a specific artefact — kickoff, direction selection, design concept review, product spec, full experience review, launch review. The model prevents teams from shipping solutions to poorly-framed problems.
  • Six-month rolling plans beat annual plans for strategy and quarterly plans for shipping. Asana moved from annual to rolling 12-month planning, reviewed every six months, with high confidence in the near half and lower confidence in the far half. This creates enough horizon for go-to-market alignment without the rigidity that produces wrong priorities in month ten of a twelve-month plan.
  • Trust = (credibility + reliability + authenticity) / perception of self-interest. This formula, attributed to board member Anne Raimondi, gives Costello a diagnostic for broken relationships. When a PM is not getting traction with a cross-functional stakeholder, she checks each variable: credibility (are you bringing insight?), reliability (are you doing what you say?), authenticity (are you being yourself?), and self-interest (do they believe your motives are aligned?). Usually, one of the four explains the friction.
  • Leading by example teaches more than explicit instruction. Costello attributes much of her coaching effectiveness to running her own meetings the way she wants her team to run theirs — sharp agenda, time for real debate, genuine scanning of the room. The mechanism is exposure: if people experience well-run meetings repeatedly, the pattern transfers without a seminar on meeting management.
  • “Think big, ship small” is not a contradiction. A PM who ships incrementally without maintaining a large frame will optimise metrics at the cost of the product’s purpose. The discipline is to hold both simultaneously: the long-run aspiration anchors decisions about what to ship next, and the small increment produces the data needed to update the aspiration. Neither alone is sufficient.

Overview

Paige Costello leads the core product organisation at Asana, responsible for the desktop, web, and mobile experience — goals, portfolios, projects, tasks, and reporting. Before Asana she was director of product at Intercom and spent five and a half years as group PM at Intuit, where she credits the Intuit APM programme and feedback training (situation–behaviour–impact format) as foundational. The episode covers Asana’s planning evolution (annual to six-month rolling), the Double Diamond process and how artefacts map to its inflection points, hybrid office policy, how she wins trust with more experienced stakeholders, the “above or below the line” consciousness model from The 15 Commitments of Conscious Leadership, and the most common mistakes she sees in early-career PMs.