Paige Costello (Asana, Intercom, Intuit)09 July 2023

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

8Frameworks

15Insights

Episode overview

Paige Costello explains how Asana evolved its product planning into a rolling 12-month process and maps product reviews onto the Double Diamond framework. She argues that product leaders earn trust by bringing firsthand customer and market insight, asking strong questions, communicating openly, and staying curious rather than pretending to know everything. The conversation also covers coaching through example, giving actionable feedback, rejecting false trade-offs, adopting AI through rapid prototypes, and designing teams with clearer decision ownership.

Key ideas

Earn trust by knowing the customer, market, competitors, numbers, and product well enough to bring useful insight.
Asana plans every six months across a rolling 12-month horizon, with higher confidence in the nearer half.
The Double Diamond alternates broad exploration with narrow selection across customers, problems, directions, and solutions.
Confidence often appears as presence, vulnerability, thoughtful questions, and comfort saying that you do not understand.
Use experience, exposure, and education together to accelerate professional development.
New product managers should favor genuine inquiry and collaboration over performative certainty and premature advocacy.
Think big but ship small, preserving ambitious direction while delivering iterative increments.
Rapid AI prototyping can expose promising opportunities before teams invest in the full normal product process.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Influence3 steps

Bring the Insight to Win Over Skeptics

Earn trust from more-experienced people by owning customer insight, not by faking expertise

Read →

Mindset3 steps

How Might the Opposite Be True

Break a scarcity or false-tradeoff frame by forcing yourself to argue the reverse

Read →

Self-Mastery3 steps

Learning Curve, Environment, Problem

Evaluate whether to stay in or leave a role using three questions, not job titles

Read →

Productivity3 steps

Single-Owner Review Limits

Cap reviews, approvals, and meeting size so one accountable owner drives the pace

Read →

Leadership3 steps

Situation-Behavior-Impact Feedback

Deliver hard feedback as an undeniable subjective observation, not a verdict

Read →

Innovation4 steps

The Double Diamond Product Process

Alternate broad exploration and narrow selection across customer, problem, and solution

Read →

Self-Mastery3 steps

The Three E's of Career Growth

Grow faster by deliberately balancing experience, exposure, and education

Read →

Influence4 steps

The Trust Equation

Trust = (credibility + reliability + authenticity) / perception of self-interest

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 9

Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter
“welcome to Lenny's podcast where I interview world-class product leaders and growth experts”
▶ Watch at ~0:30approx.
Paige CostelloMentionsPaige is a product lead at Asana overseeing teams responsible for the core product experience of Asana
“today my guest is Paige Costello”
▶ Watch at ~0:30approx.
Paige CostelloMentionsPaige is a product lead at Asana overseeing teams responsible for the core product experience of Asana
“before Asana she was director of product at intercom and prior to that she was a group product manager into it”
▶ Watch at ~1:00approx.
Jackie BavaroMentionsA big thank you to Jackie Bavaro
“A big thank you to Jackie Bavaro”
▶ Watch at ~4:00approx.
Anne RaimondiMentionsour former board member and raymondi and now our head of business wrote an article on first round
“our former board member and raymondi and now our head of business wrote an article on first round”
▶ Watch at ~23:30approx.
Scott CookMentionsthere's the story about Scott Cook watching his wife balancing her checkbook at the kitchen table
“there's the story about Scott Cook watching his wife balancing her checkbook at the kitchen table”
▶ Watch at ~42:30approx.
Marty CaganCoinedMarty has been helping product teams and product managers improve their craft processes and careers for over 20 years
“my go-to book recommendation for other PMS is inspired by Marty Kagan”
▶ Watch at ~55:30approx.
Paulo CoelhoCoinedThe Alchemist by Paula cuello
“The Alchemist by Paula cuello”
▶ Watch at ~56:00approx.
Margaret AtwoodCoinedthe blind Assassin by Margaret Atwood
“the blind Assassin by Margaret Atwood”
▶ Watch at ~56:00approx.

Resources · 28

Lenny's PodcastCoinedpodcast · Lenny Rachitsky
“welcome to Lenny's podcast where I interview world-class product leaders and growth experts”
▶ Watch at ~0:30approx.
IntuitMentionscompany
“prior to that she was a group product manager into it where she spent five and a half years”
▶ Watch at ~1:00approx.
IntercomMentionscompany · Intercom
“before Asana she was director of product at intercom”
▶ Watch at ~1:00approx.
Brave Search APIMentionstool · Brave Software
“their newest product the brave search API an independent Global search index you can use to power your search or AI apps”
▶ Watch at ~1:30approx.
AttioMentionssoftware · Attio
“this episode is brought to you by atio a new type of CRM that's powerful flexible and built around your data”
▶ Watch at ~3:00approx.
AsanaMentionssoftware · Asana, Inc.
“I lead the product organization that's responsible for our desktop web and mobile apps at Asana”
▶ Watch at ~4:30approx.
Double DiamondUsesother
“I think you use a process called The Double Diamond process at assignment”
▶ Watch at ~12:30approx.
Double DiamondUsesother
“each of our typical reviews or artifacts sit at different inflection points on the Double Diamond”
▶ Watch at ~13:30approx.
AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk
“it was at Airbnb”
▶ Watch at ~21:00approx.
First Round ReviewMentionswebsite · First Round Capital
“our former board member and raymondi and now our head of business wrote an article on first round”
▶ Watch at ~23:30approx.
SlackUsessoftware · Slack Technologies
“looking at your computer and going through slack messages”
▶ Watch at ~27:00approx.
RoundMentionscompany
“round is the private Network built by Tech leaders for Tech leaders”
▶ Watch at ~28:00approx.
The Conscious Leadership GroupMentionscompany · Jim Dethmer and Diana Chapman
“it's led by the conscious leadership group”
▶ Watch at ~35:00approx.
IntuitMentionscompany
“the biggest thing that they taught was around customer centricity”
▶ Watch at ~42:00approx.
InspiredRecommendsbook · Marty Cagan
“my go-to book recommendation for other PMS is inspired by Marty Kagan”
▶ Watch at ~55:30approx.
Fire of LoveMentionsdocumentary
“I just watched the fire of Love documentary which is about a couple who study volcanoes”
▶ Watch at ~56:00approx.
The Blind AssassinRecommendsbook · Margaret Atwood
“the other books that I have enjoyed and recommended lately are the blind Assassin by Margaret Atwood”
▶ Watch at ~56:00approx.
The AlchemistRecommendsbook · Paulo Coelho
“The Alchemist by Paula cuello”
▶ Watch at ~56:00approx.
The DiplomatMentionstv show
“I'm very much enjoying the Diplomat right now”
▶ Watch at ~56:00approx.
PoeUsessoftware · Quora
“I've been playing a lot with poe.com lately”
▶ Watch at ~57:30approx.
PoeMentionssoftware · Quora
“po just it's the quora founders llm chatbot”
▶ Watch at ~58:00approx.
QuoraCoinedwebsite
“po just it's the quora founders llm chatbot”
▶ Watch at ~58:00approx.
Lenny's NewsletterCoinednewsletter · Lenny Rachitsky
“it is trained on all of my newsletter posts”
▶ Watch at ~58:30approx.
LennybotMentionswebsite · Lenny Rachitsky
“there's also a lennybot.com for folks that haven't seen this”
▶ Watch at ~58:30approx.
LennybotMentionswebsite · Lenny Rachitsky
“it is trained on all of my newsletter posts”
▶ Watch at ~58:30approx.
AsanaUsessoftware · Asana, Inc.
“I use Asana to run all my meetings and assign pre-reads”
▶ Watch at ~1:01:00approx.
LinkedInUseswebsite · LinkedIn
“you can find me on LinkedIn and Twitter page Costello”
▶ Watch at ~1:02:00approx.
TwitterUseswebsite · Twitter
“on Twitter at page now”
▶ Watch at ~1:02:00approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 1

Hot Take22:00

How to Win Over Skeptics When You're the Youngest in the Room: Bring the Insight

Being often the youngest person leading more experienced people, Paige's approach to earning trust is to bring insight rather than fake expertise. Know your customer, market, competitors, numbers, and product deeply. If you can speak with confidence and clarity about how customers actually use the product, you make people curious and earn trust without needing their functional expertise.

Don't pretend to have experience you lack; instead bring genuine insight
Know your customer, market, competitors, numbers, and product
Being the person who has watched customers use the product creates credibility
Ask great questions and stay curious rather than posturing as the expert

“the thing I would say is bring the Insight Know Thy customer know they Market know like competitors know like numbers Know Thy product”
Paige Costello · 22:00

“you can bring Insight that makes people curious and trust you”
Paige Costello · 22:30

#trust#leadership#product-management#influence

Explainer· 3

Explainer06:30

Why Asana Switched to Six-Month Plans for a Rolling 12 Months

Paige explains how Asana's planning process evolved as the company scaled. They moved from annual planning to replanning every six months for a rolling twelve-month window, giving high confidence in the near half and lower confidence in the following half. They also made roadmaps explicitly cuttable, treating a roadmap item as something that can be pivoted or dropped rather than a binding commitment.

Shifted from primarily annual planning to replanning every six months for a rolling 12 months
High confidence in the immediate half, lower confidence in the following half
More frequent replanning aligns go-to-market and product, and reduces churn and thrash
Added an explicit norm that roadmap items can be pivoted or cut, not treated as mandatory once listed

“before we planned annually primarily and now we plan every six months but for a rolling 12 months”
Paige Costello · 08:30

“once it was on the roadmap it had to be done and that's just not smart”
Paige Costello · 11:00

#planning#product-process#roadmap#asana

Explainer45:30

What Holds New PMs Back: Advocacy Instead of Inquiry

Paige says the biggest thing holding new PMs back is the illusion that they must be all-knowing and confident, which pushes them into advocacy instead of inquiry. They do discovery alone, then arrive declaring the answer, shutting down the questions that would make them smarter. She argues real curiosity and openness lead to better outcomes, and that strong work earns promotion without asking.

The illusion of needing to be all-knowing pushes PMs into advocacy over inquiry
Working in a 'dark room' then declaring the answer kills useful questions
Genuine curiosity and openness, not performative collaboration, drive success
If you're present and solve problems, people advocate for you; you don't need to ask for a promotion

“this illusion you have to be all-knowing and super confident sets you up to be in a place of advocacy instead of inquiry”
Paige Costello · 46:00

“you don't need to ask for a promotion your outcomes should speak for themselves”
Paige Costello · 48:30

#product-management#career-advice#collaboration#curiosity

Explainer59:00

The Process Change That Sped Up Asana: Fewer Reviews and Approvers

Paige names being real about how many reviews and approvals a piece of work needs as a small change with big impact. Asana got aggressive about who is actually responsible at each level, capping the number of blocking reviews and meeting attendees. This created more agency and pace within working teams.

Be honest about how many reviews and approvals work actually requires
No more than three reviews on a piece of work, with only one person blocking approval
Meetings over 10 people: host must kick people out and write better decision notes
Fewer approvers created more agency, pace, and quality within teams

“no more than three reviews on a given piece of work where people are blocking one approver”
Paige Costello · 1:00:30

“if a meeting has 10 more than 10 people on it we ask the person hosting the meeting to kick out the other people and…”
Paige Costello · 1:00:30

#product-process#execution#meetings#decision-making

Story· 4

Story32:00

The Intuit Advice That Changed How Paige Answers Questions

After a high-stakes product review at Intuit, a business unit leader told Paige on her way out to always answer the question they should have asked. It struck her because achievers tend to answer questions one-to-one, but real strategy means addressing the bigger picture or the alternative the asker didn't see or consider.

A business unit leader's parting advice: answer the question they should have asked
High achievers default to literal, one-to-one question answering
There's another altitude of strategy: cover the more important underlying point
Surface the alternative or bigger picture the asker may have missed

“always answer the question they should have asked”
Paige Costello · 32:30

“there's actually another altitude another point of strategy when you're in a meeting or in a conversation to make sure that you're covering the more…”
Paige Costello · 33:00

#communication#strategy#career-advice#intuit

Story36:30

How Might the Opposite Be True: Beating a Scarcity Mindset

Paige shares a self-coaching question she uses to reject false trade-offs: how might the opposite be true. She recounts feeling overwhelmed by having to deliver a major pillar brief and record the podcast on the same day, then asking the question and realizing she could do both. It popped the balloon of a scarcity mindset and let her relax.

Use 'how might the opposite be true' to challenge false trade-offs
A scarcity mindset blocks seeing alternative options or a different path
Real example: feeling she had to cancel one of two big same-day commitments
Asking the question let her realize she could do both and relax

“sometimes your brain is so accustomed to having a scarcity mindset as opposed to like creating alternative options or seeing a different path”
Paige Costello · 37:30

“the moment I challenged myself and said how might the opposite be true my shoulders dropped I felt more relaxed I was like oh yeah…”
Paige Costello · 38:00

#mental-models#mindset#decision-making#productivity

Story42:00

The Intuit Customer-Centricity Lesson (and the Scott Cook Checkbook Story)

Paige describes what she took from Intuit's famous PM program: deep customer centricity rooted in the company's founding story of Scott Cook watching his wife balance her checkbook and thinking there had to be a better way. The training emphasized watching customers actually use the product, collecting their artifacts and workarounds, and building products from that firsthand insight.

Intuit's PM training centers on customer centricity from the company's founding story
Scott Cook watched his wife balance her checkbook and saw a software opportunity
Watch customers use the product; collect their artifacts and workarounds
Use that firsthand experience to build opportunities for surprise and insight

“there's the story about Scott Cook watching his wife balancing her checkbook at the kitchen table and staring at it saying there's got to be…”
Paige Costello · 42:30

#customer-research#product-management#intuit#training

Story50:30

When Being Too Positive Made Paige Seem Inauthentic

Paige shares a leadership misstep: as a naturally optimistic person, she avoided dwelling on problems because she trusted the plan. But her team read her silence on the bad stuff as inauthentic, thinking she either didn't see the problems or wasn't being real. She learned to name what's incomplete or not working, being real about small things as well as big ones.

Paige's optimistic nature led her to avoid highlighting problems she did see
Teams sometimes need you to be real and tell them what's bad
Silence on problems can read as inauthenticity, not confidence
Fix: openly name what's incomplete (e.g. 'this is 70% done') on small and big things alike

“I'm a very optimistic person and I like to look on the bright side”
Paige Costello · 50:30

“I didn't realize that people didn't think I was being authentic because they thought something was bad and I wasn't talking about it”
Paige Costello · 51:00

#leadership#authenticity#management#communication

Q&A· 1

Q&A17:30

Asana's Office-Centric Hybrid Policy and Relearning In-Person Muscles

Asked about the return-to-office shift, Paige describes Asana's deliberate office-centric hybrid: in the office Monday, Tuesday, and Thursday, working from home mostly Wednesday and Friday. She notes the plan was set from the very beginning rather than agonized over, and reflects on how quickly teams lost in-person habits like standing up during stand-ups and using whiteboards, and how vibrancy has returned.

Office-centric hybrid: in-office Mon/Tue/Thu, home mostly Wed/Fri
The policy was decided from the start, avoiding hemming and hawing over remote vs office
Teams lost in-person habits (stand-ups, whiteboards) surprisingly quickly
Casual, unscheduled conversations are cited as a major benefit for strategy and mental health

“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…”
Paige Costello · 17:30

“it's bizarre that we could lose a muscle that we had that was so innate uh so quickly”
Paige Costello · 19:00

#remote-work#hybrid#culture#asana

Tool· 1

Tool1:01:00

Paige's Asana Pro Tip: Multi-Assign Subtasks for Meetings

Paige runs all her meetings in Asana. She uses the multi-assign feature in subtasks to send pre-reads with due dates to a team or set of individuals at once, then takes notes live in a task during the meeting and converts highlighted parts into subtasks so no action items get lost.

Use the multi-assign feature in subtasks to assign pre-reads to many people at once
Set a due date so the pre-read is done before the meeting
Take meeting notes live in a task
Highlight parts of the notes and convert them into subtasks so action items aren't lost

“I use the multi-assign feature in subtasks all the time”
Paige Costello · 1:01:00

“when I'm in the meeting I take notes live in a task and then highlight parts of those notes and convert them into subtasks so…”
Paige Costello · 1:01:30

#asana#tools#meetings#productivity

Takeaway· 5

Takeaway21:00

Guard Your Peak Hours: Know Your Chronotype

Paige advises knowing your chronotype and protecting the window when you have the most mental headspace for your hardest work. As a morning person, she blocks meetings before 10 or 11am so that time is reserved for her most demanding tasks.

Identify your chronotype and protect the time you have the most head space
Paige, a morning person, avoids meetings before 10-11am
Use that protected window for your hardest task of the day

“I would encourage you to know your chronotype and to walk that time where you have the most head space to do that work”
Paige Costello · 21:00

#productivity#deep-work#time-management

Takeaway26:00

Real Confidence Is Being Willing to Ask the Question

On projecting confidence, Paige argues it comes from being brave in small moments, showing up before you're ready, and being vulnerable rather than armored. Real confidence is conveyed by being willing to ask a question or admit you don't understand, plus attentiveness, eye contact, and body language that shows you're present.

Be brave and courageous in small moments; speak before you're fully ready
Vulnerability builds more trust than projecting all-knowing armor
Confidence shows in willingness to ask questions and admit confusion
Body language, eye contact, and scanning the room convey more than assertiveness

“you have to show up and say it before you're ready to say it and ask for forgiveness and be vulnerable”
Paige Costello · 26:30

“real confidence is often conveyed by being willing to ask the question or to say I don't know what you mean by that”
Paige Costello · 27:00

#confidence#communication#leadership#vulnerability

Takeaway29:00

Why Coaching by Example Beats Telling People What to Do

Paige explains her preference for teaching by example over instruction, grounding it in repetition: we are all students of repetition, and seeing something done a few times makes it stick. She runs her meetings the way she wants meetings run, so people internalize the pattern by exposure rather than being lectured.

We're all students of repetition; seeing something done a few times helps internalize it
Run your meetings the way you want meetings to be run elsewhere
Model the behavior you hope people replicate in rooms you're not in
Leading by example teaches a repeatable pattern rather than a one-off instruction

“I think the main thing is repetition uh we're all students of repetition if you see something done a few times you're more likely to…”
Paige Costello · 29:30

#coaching#management#leadership#mentoring

Takeaway34:00

Two Pieces of Advice: Don't Self-Select, and Think Big Ship Small

Paige shares recurring advice she gives. First, don't self-select out of opportunities by assuming you lack the experience; apply anyway. Second, think big but ship small: work in small chunks toward a big vision to avoid getting too incremental and losing the bigger picture.

Don't self-select out; it's easy to say you're not experienced enough and not apply
Think big, ship small: find the smallest thing you can do toward the big goal
Shipping small chunks avoids getting too incremental and wrapped around a metric
Advice lands best when tailored to a specific person at a specific career stage

“advice I love giving to people who are early in their career is don't self-select”
Paige Costello · 34:00

“think big ship small like what's what's the smallest thing you can do to do that thing”
Paige Costello · 34:30

#career-advice#product-management#execution

Takeaway52:30

Three Checks for Whether You're in the Right Role

On managing her career, Paige focuses on the skills and experiences she wants rather than specific roles or companies. She assesses a role by three things: the steepness of her learning curve, whether the environment (staffing, tooling, healthy people) supports her growth, and whether the problem is genuinely interesting. She adds that passions are made, not found.

Think in terms of skills and experiences you want, not roles or companies
Check the steepness of your learning curve; are you being challenged?
Check the environment: staffing, tooling, advocates, and no toxic people
Check the problem: is it fun and interesting? Passions are made, not found

“I evaluate whether I'm in a healthy role and in a good setup by asking myself about my learning curve”
Paige Costello · 53:00

“passions are made not found”
Paige Costello · 54:30

#career#growth#self-assessment#decision-making

Key ideas

Frameworks in this episode

Bring the Insight to Win Over Skeptics

How Might the Opposite Be True

Learning Curve, Environment, Problem

Single-Owner Review Limits

Situation-Behavior-Impact Feedback

The Double Diamond Product Process

The Three E's of Career Growth

The Trust Equation

People & resources mentioned

People · 9

Resources · 28

Insights & moments

◆Hot Take· 1

How to Win Over Skeptics When You're the Youngest in the Room: Bring the Insight

✶Explainer· 3

Why Asana Switched to Six-Month Plans for a Rolling 12 Months

What Holds New PMs Back: Advocacy Instead of Inquiry

The Process Change That Sped Up Asana: Fewer Reviews and Approvers

❝Story· 4

The Intuit Advice That Changed How Paige Answers Questions

How Might the Opposite Be True: Beating a Scarcity Mindset

The Intuit Customer-Centricity Lesson (and the Scott Cook Checkbook Story)

When Being Too Positive Made Paige Seem Inauthentic

?Q&A· 1

Asana's Office-Centric Hybrid Policy and Relearning In-Person Muscles

✦Tool· 1

Paige's Asana Pro Tip: Multi-Assign Subtasks for Meetings

▲Takeaway· 5

Guard Your Peak Hours: Know Your Chronotype

Real Confidence Is Being Willing to Ask the Question

Why Coaching by Example Beats Telling People What to Do

Two Pieces of Advice: Don't Self-Select, and Think Big Ship Small

Three Checks for Whether You're in the Right Role

Hot Take· 1

Explainer· 3

Story· 4

Q&A· 1

Tool· 1

Takeaway· 5