Jul 9, 2023 · 1h 3m · lennys-podcast
How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana)
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In this episode of Lenny's Podcast, Asana Product Lead Paige Costello shares practical frameworks for building credibility with senior peers, scaling product development processes, and cultivating high-leverage leadership mindsets. She offers actionable insights on roadmapping, rapid AI prototyping, cognitive reframing, and navigating intentional career growth.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 23.3% of the talking time here. How this is scored →
Lenny as informed peer 2.1 Guest teaching 5.8 Guest disagreement 0.2 Lenny pushing back 0.2
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 46:11 Rebuffing the 'smartest person in the room' mindset
Costello forcefully dismisses the common junior PM urge to act like an all-knowing authority who designs in isolation and executes performative reviews.
Hardest push from Lenny ▶ 14:43 Probing Double Diamond artifact specificsRachitsky interrupts to ask Costello to define the exact terminology for each phase and clarify how it relates directly to customer selection versus solutioning.
Biggest teaching moment ▶ 23:15 Masterclass on the trust formula and customer insightCostello breaks down the mathematical formulation of trust (credibility plus reliability plus authenticity over self-interest) and how junior leads can leverage objective customer insight.
Lenny holds their own ▶ 9:09 Synthesizing product planning trends across Shopify and AsanaRachitsky demonstrates broad domain authority by validating Costello's 6-month rolling roadmap shift with recent firsthand insights from Shopify product leadership.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| Defining Paige Costello's Core Product Role at Asana | 4 | 5 | 0 | 1 | Costello outlines how Asana evolved its planning hierarchy from ad-hoc projects to nested pillars and areas with rolling 12-month roadmaps. Rachitsky connects this directly to similar shifts he observed talking with product leaders at Shopify. | |
| Executing the Double Diamond Framework and Review Cadence | 3 | 6 | 0 | 1 | Costello breaks down the mechanics of the Double Diamond framework and how Asana maps review milestones to divergence and convergence phases. Rachitsky probes into whether the framework is strictly customer-target focused and how reviews are conducted. | |
| Navigating In-Person Collaboration and Hybrid Work Realities | 4 | 3 | 0 | 0 | The conversation shifts to return-to-office dynamics and hybrid schedules. Rachitsky shares his own experience from Airbnb regarding meeting-free Wednesdays and rowdy team standups, while Costello emphasizes protecting chronotype deep-work blocks. | |
| Building Trust, Winning Skeptics, and Projecting Real Confidence | 2 | 7 | 0 | 0 | Costello shares a detailed masterclass on building trust as a younger leader by leading with deep customer insight and leveraging the trust equation. Rachitsky listens attentively and prompts her to expand on communicating with confidence. | |
| Sponsor Break: Round Leadership Network | 2 | 6 | 0 | 0 | Following the sponsor break, Costello explains the Three E's framework (Experience, Exposure, Education) and recounts how an Intuit executive taught her to answer the question that should have been asked. | |
| Conscious Leadership, Cognitive Reframing, and Managing Priorities | 1 | 7 | 1 | 0 | Costello introduces the 15 Commitments of Conscious Leadership and the concept of above versus below the line thinking. She explains how asking 'how might the opposite be true' helped dissolve her scarcity mindset when preparing for this very podcast. | |
| Asana's AI Strategy and Rapid Prototyping Workflow | 2 | 6 | 0 | 0 | Rachitsky asks how Asana allocates resources for generative AI exploration, and Costello describes how they spun up a dedicated fast-prototyping squad that bypassed traditional process gates before handing prototypes to domain teams. | |
| Customer Centricity and Situation-Behavior-Impact Feedback at Intuit | 2 | 7 | 0 | 0 | Costello details Intuit's customer obsession philosophy (follow-me-home research) and the Situation-Behavior-Impact (SBI) feedback model. Rachitsky highlights how crucial soft skills are compared to purely technical product management frameworks. | |
| Common Pitfalls Holding Back Early-Career Product Managers | 1 | 7 | 1 | 0 | Costello critiques junior PMs who fall into performative collaboration or feel pressured to act as all-knowing experts rather than practicing genuine inquiry. She advises them to let outcomes speak rather than obsessing over promotions. | |
| Managerial Mistakes, Self-Restraint, and Radical Candor | 1 | 6 | 0 | 0 | Costello candidly reflects on management missteps, including using sticky notes to stop herself from speaking over others in meetings and learning to be open about product flaws rather than defaulting to toxic positivity. | |
| A Strategic Framework for Career Growth and Role Evaluation | 1 | 6 | 0 | 0 | Costello presents her tripartite framework for evaluating career moves—learning curve, environment, and problem interest—emphasizing that passion is developed through curiosity rather than discovered pre-formed. | |
| Lightning Round: Recommendations, LLM Tools, and Asana Pro Tips | 2 | 4 | 0 | 0 | In the lightning round, Costello recommends books, shares interview questions, and details tactical Asana pro-tips, such as converting live meeting notes into actionable subtasks with multi-assign. |
Statements from this episode (15)
Costello: Asana replaced annual planning with a rolling 12-month horizon
“Before we planned annually primarily, and now we plan every six months, but for a rolling 12 months. And so we have higher confidence in the immediate half, lower confidence in the following half, but we just plan every 12 months, every six months, because it …”
Costello: Rigid quarterly deadlines lead to strange product scoping decisions
“If you ask too much for a particular quarter or a particular week or date, people make strange choices about scope, and so really we align on what success looks like, and the teams do their best job to ship as quickly as possibly, as iteratively as possibly”
Costello: Measuring feature usage instead of customer outcomes is teaching to the test
“Because if you pick your success metrics as using a feature, that's, you're teaching to the test. It's not actually driving the outcome.”
Costello: Asana operates on a three-day in-office hybrid schedule
“Well, we were fully remote during the pandemic, and then we came back to the office in an office-centric hybrid format. So we're in the office Monday, Tuesday, Thursday, and then work from home mostly on Wednesdays and Fridays.”
Costello: Returning to office benefits mental health and spontaneous collaboration
“I think it's a real thing for mental health. I do think that having social casual relationships as well as more opportunities to talk strategy with people you're not forced into a meeting room with has been super beneficial.”
Costello: New PMs should directly observe customers rather than trust summaries
“When you take a new role, become best friends with a researcher and spend time with watching customers use the product firsthand, because what they maybe report on or are trying to do a study about might be very different from what you observe, but you really …”
Costello: Heavy dog-fooding cultures blind teams to actual customer needs
“Especially in organizations where there are heavy dog-fooding cultures. It's really risky to become less sensitive to the needs and behaviors of customers because people think they are their customer. And it also becomes very navel-gazy.”
Costello: Genuine confidence comes from openness, not constant assertion
“Real confidence is often conveyed by being willing to ask the question or to say, I don't, Know what you mean by that. Can you say that again?... It's really about being open and that conveys confidence more than being assertive and advocating a hundred percen…”
Costello: In strategic meetings, answer the question they should have asked
“Our, like, the leader of the business unit, as she was leaving the room, said, always ask, or always answer the question that they should have asked, and always answer the question they should have asked, and I was pretty surprised by that advice, because it w…”
Costello: New Asana employees undergo conscious leadership training
“When cut when employees join Asana, they get a book called The 15 Commitments of a Conscious Leader. It's led by the Conscious Leadership Group. They also get two-day training on some, like, language and tools for how to Effectively work with other people.”
Costello: Asana Bypassed Standard Product Process for Rapid LLM Prototyping
“When it came to the massive leap forward in LLMs recently, we staffed a team to really prototype quickly and discover what was possible and just apply hypotheses outside of the typical norms of how we work. So they kind of went straight to prototyping instead …”
Costello: PMs do not need to ask for promotions
“You don't need to ask for a promotion. Your outcomes should speak for themselves, and yes, you should have sponsors and people who advocate for you, But a lot of that just comes from that, like, raw connection to the work and to your team.”
Costello: Good managers teach repeatable patterns over one-off instructions
“What you're trying to do is to teach a repeatable pattern instead of giving a precise instruction that can be used once and then disposed of.”
Costello: Managers must police their airtime because employees rarely challenge bosses
“You've got to police yourself because no one else will do it, because no matter how accessible. You think you are. Other people know that you're the boss. They're not gonna necessarily speak over you or challenge you directly.”
Costello: Asana caps product reviews at three and meetings at 10 attendees
“So no more than three reviews on a given piece of work where people are blocking one approver. And If a meeting has more than 10 people on it, we ask the person hosting the meeting to kick out the other people and write better decision notes.”