Lenny's PodcastHow to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana)
CHAPTERS
- 0:00 – 0:42
Cold open: earning trust as the youngest person in the room
A quick teaser sets the episode’s theme: winning over skeptics through preparation and insight. Paige hints that credibility comes from knowing customers, the market, and the numbers—then asking sharp questions.
- •Garnering trust is less about seniority and more about insight
- •Deep customer/market/competitive knowledge as a credibility shortcut
- •Curiosity and strong questions as a leadership lever
- 0:42 – 3:44
Episode setup: Paige’s roles across Asana, Intercom, and Intuit
Lenny introduces Paige’s background and what the conversation will cover, from product process to coaching and career lessons. Sponsor messages follow before the interview begins.
- •Paige’s current scope: product lead at Asana
- •Prior experience at Intercom and Intuit
- •Preview of topics: trust, coaching, process, and missteps
- 3:44 – 4:38
Starting the conversation: how Paige’s colleagues shaped the questions
Lenny explains he gathered prompts from Paige’s current and former coworkers, setting up a practical, experience-driven interview. Paige reacts and the discussion pivots into her current responsibilities.
- •Colleague-sourced questions to ground the conversation
- •Establishing rapport and context for the interview
- •Transition into Paige’s day-to-day scope at Asana
- 4:38 – 6:04
Paige’s scope at Asana: owning the core product experience
Paige explains what her org builds across web, desktop, and mobile, and what “clarity” means in Asana’s product strategy. She frames the core user value as answering ‘who’s doing what by when—and why.’
- •Teams responsible for Asana’s core work management experience
- •Clarity as a product north star (purpose, plan, progress, responsibility)
- •Feature surface area: goals, portfolios, projects, tasks, reporting
- •How her org fits alongside other pillars (workflow, adoption/enterprise scale)
- 6:04 – 8:19
How Asana’s product planning evolved: pillars → areas → teams, and better metrics
Paige describes how Asana changed its planning ‘altitudes’ as it scaled, adding an ‘area’ layer to improve ownership and accountability. She also explains how metrics nest from R&D to pillar to area to team.
- •Shift from feature/project-driven planning to durable, problem-focused planning
- •Definition of pillars and areas; why areas were added
- •Nested metrics structure to align strategy and measurement
- •Organizing around target customers and problem spaces
- 8:19 – 11:26
Rolling planning cadence: six-month planning for a rolling 12 months
Asana moved from annual planning to revisiting plans every six months while maintaining a 12-month view. Paige explains how this reduces thrash, improves GTM alignment, and keeps teams principled when strategy changes.
- •Higher confidence in the near half; lower confidence in the back half
- •Planning frequency as a tool for fast pivots without chaos
- •Why strict dates can drive bad scope decisions
- •Emphasis on success definitions and iterative shipping
- 11:26 – 12:46
Concrete examples: what an “area” is and how Asana chooses health metrics
Paige gives a specific example of an area (Coordinate) and the kinds of metrics it tracks. The focus is on balancing growth indicators with guardrails that reflect real user value, not vanity usage.
- •Example area: Coordinate (projects/tasks collaboration layer)
- •Example metrics: org paying WAU and “healthy project use”
- •Defining ‘good looks like’ to avoid metric gaming
- •Using guardrails to prevent optimizing one metric at users’ expense
- 12:46 – 17:27
Asana’s double-diamond in practice: artifacts, reviews, and decision quality
Paige breaks down the double-diamond approach as repeated divergence and convergence—starting with customer selection and ending with launch readiness. She maps Asana’s rituals (kickoff, concept reviews, specs, crits) to the framework and explains when reviews are async vs in-person.
- •Go broad/go narrow across customer, problem, and solution
- •Artifacts at inflection points: kickoff → direction selection → concept review → spec → full experience review → launch
- •Avoiding “teaching to the test” metrics that only measure feature usage
- •Choosing async vs in-person based on ambiguity and complexity
- 17:27 – 21:45
Office-centric hybrid at Asana: rebuilding the in-office muscle
The conversation shifts to work culture: Asana’s Monday/Tuesday/Thursday in-office cadence with remote Wednesdays and Fridays. Paige shares how teams re-learned in-person collaboration and why casual collisions can accelerate strategy and decision-making.
- •Hybrid model: in-office 3 days, remote 2 days
- •Why Asana committed early rather than debating remote-first
- •Rebuilding habits: whiteboards, standing standups, office energy
- •In-person serendipity enabling faster, unscheduled strategic conversations
- 21:45 – 26:18
Winning over skeptics: insight, the trust equation, and researcher “best friends”
Paige details how she earns trust with more experienced stakeholders by being the person who brings real customer and market insight. She introduces a practical trust equation and argues that close partnership with researchers speeds up true customer understanding.
- •“Bring the insight”: customers, market, competitors, numbers, product
- •Trust equation: credibility + reliability + authenticity / self-interest
- •Reliability as “say-do ratio”; authenticity as vulnerability
- •Befriend researchers and watch customers firsthand to avoid dogfood bias
- 26:18 – 29:04
How to project confidence: presence, vulnerability, and asking ‘basic’ questions
Paige reframes confidence as openness rather than armor—being willing to admit uncertainty, clarify, and stay present. She shares practical behaviors: eye contact, body language, and running meetings with intentional attention.
- •Confidence comes from courage in small moments
- •Vulnerability and “I don’t know—can you say that again?” as strength
- •Presence: don’t multitask; scan the room; create space for questions
- •Opening/closing rituals that make conversations feel grounded and complete
- 29:04 – 33:59
Coaching by example + the 3Es: experience, exposure, education
Paige explains why modeling behaviors beats purely giving advice: repetition is how people internalize new patterns. She introduces the 3Es framework and shares concrete examples, including an Intuit lesson: answer the question they should have asked.
- •Why leading by example works: repetition builds instincts
- •3Es framework: experience, exposure, education
- •Designing meetings as the “template” you want others to copy
- •Intuit takeaway: address the bigger strategic question, not only the literal one
- 33:59 – 40:04
Career and product principles: don’t self-select, think big/ship small, stay above the line
Paige shares recurring advice for early-career PMs and the mindset tools she uses herself. She highlights Conscious Leadership concepts—operating above/below the line—and a reframing question that breaks scarcity thinking: ‘How might the opposite be true?’
- •Early-career advice: don’t self-select out of opportunities
- •Product mantra: think big, ship small (avoid small thinking)
- •Above the line vs below the line: learning/curiosity vs winning/being right
- •Reframing tool: “How might the opposite be true?” to reject false trade-offs
- 40:04 – 41:50
AI at Asana: prototyping fast, then handing keys to domain teams
Paige describes how Asana approached the LLM wave: a dedicated team bypassed normal process to prototype quickly and test feasibility. Once promising, ownership shifts to teams closest to the customer problem to scale learning into real product work.
- •Existing ML foundations (e.g., prioritization models) vs new LLM leap
- •Prototype-first to test what’s actually possible (skip the usual diamond early)
- •Rapid validation: some ideas better than imagined, others fail fast
- •Transition model: seed hypotheses, then empower domain teams to execute
- 41:50 – 45:53
What Intuit taught Paige: customer-centricity and situation-behavior-impact feedback
Paige reflects on Intuit’s strong PM and manager training programs. The biggest managerial takeaway is a structured feedback method that focuses on observed impact and enables action without requiring “objective proof.”
- •Intuit’s customer-centric product training and origin stories
- •Building insight from observing real workflows and artifacts
- •Manager training highlight: situation–behavior–impact feedback format
- •Feedback framed as lived experience to open productive next steps
- 45:53 – 48:55
What holds new PMs back: advocacy over inquiry and performative collaboration
Paige explains that many new PMs feel pressure to look like experts, which pushes them toward solitary decision-making and rigid advocacy. The antidote is genuine curiosity—inviting questions early, clarifying feedback, and staying connected to the work rather than chasing promotions.
- •New PM trap: trying to be all-knowing instead of inquisitive
- •Risks of building in isolation then “revealing” the answer
- •How to handle feedback: clarify the intent (must/should/consider)
- •Career advice: focus on outcomes and craft; recognition follows
- 48:55 – 52:40
Missteps and growth: micromanagement instincts, optimism gaps, and being ‘70% done’ out loud
Paige shares lessons learned the hard way as she moved into management: resisting the urge to over-direct and learning to be more explicit about what’s not working. She offers tactics like “Post-it policing” to create space for others and modeling authenticity by naming what’s incomplete.
- •Manager pitfall: giving precise instructions instead of repeatable patterns
- •Technique: write impulses on Post-its to avoid dominating discussions
- •Optimism can read as inauthentic if you don’t acknowledge problems
- •Practical fix: explicitly label what’s missing (e.g., ‘this is 70% done’)
- 52:40 – 1:03:20
Skill-focused career philosophy + lightning round (books, interview prompts, process tips, Asana workflow)
Paige outlines how she evaluates her career through learning curve, environment, and problem interest—optimizing for skills and experiences over titles. The lightning round covers her most recommended books, an interview question about failure, a process tweak to reduce approval drag, and her favorite Asana power-use workflow for meetings.
- •Career evaluation lenses: learning curve, environment, and problem fit
- •“Passions are made, not found” and experimentation over long-range certainty
- •Execution boost: limit reviewers/approvals; cap meeting size; strengthen decision notes
- •Asana pro tip: run meetings via tasks, multi-assign pre-reads, convert notes to sub-tasks
