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How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana)

How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana)

43 segments available

Paige Costello is a beloved product leader with a reputation as a remarkable coach and mentor. She is currently the Head of Core Product at Asana, where she leads the group responsible for Asana’s web, desktop, and mobile apps. Prior to that role, she served as the Director of Product at Intercom and, before that, as a Group PM at Intuit, where she kickstarted her product career through their renowned APM program. In today’s episode, we discuss: • The unique product development process at Asana and how it’s evolved • The double-diamond framework • Conscious leadership training, and why every Asana employee learns it • How to demonstrate confidence and earn trust from skeptics • Why curiosity and openness may be the most important PM competencies • How to give feedback using impact statements — Brought to you by Brave Search API—An independent, global search index you can use to power your search or AI app | Attio—The powerful, flexible CRM for fast-growing startups | Round—The private network built by tech leaders for tech leaders Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-ask-the-right-questions-project Where to find Paige Costello: • Twitter: https://twitter.com/paigenow • LinkedIn: https://www.linkedin.com/in/paigecostello/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Paige’s background (04:38) What Paige is responsible for at Asana (06:04) The evolution of Asana’s product development process (09:10) Planning frequency (11:26) Examples of areas and metric tracking at Asana (12:46) The double-diamond process and how it’s applied at Asana (16:53) Asana’s office-centric hybrid work culture and the future of WFH (21:45) How to garner trust and win over skeptics (24:45) Why you should befriend researchers (26:17) How to exude confidence (29:03) The 3Es framework (33:43) Advice for early-career PMs (38:43) Paige’s latest pillars strategy (40:05) AI at Asana (41:50) Lessons from Paige’s time at Intuit (45:53) Challenges new PMs face (48:55) Challenges Paige has faced in her career (52:39) Paige’s skill-focused career philosophy (55:43) Lightning round Referenced: • Use This Equation to Determine, Diagnose, and Repair Trust: https://review.firstround.com/use-this-equation-to-determine-diagnose-and-repair-trust • About conscious leadership at Asana: https://wavelength.asana.com/workstyle-simple-shift/ • The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable/dp/0990976904 • Intuit: https://www.intuit.com/ • Inspired: How to Create Tech Products Customers Love: https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507 • The Blind Assassin: https://www.amazon.com/Blind-Assassin-Novel-Margaret-Atwood/dp/0385720955 • The Alchemist: https://www.amazon.com/Alchemist-Paulo-Coelho/dp/0062315005 • The Diplomat on Netflix: https://www.netflix.com/title/81288983 • Fire of Love on Disney+: https://www.disneyplus.com/movies/fire-of-love/1hC7erRfsl3B • Poe: https://poe.com/ Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

Segments Timeline

1
0:00 - 0:39
0:39 duration122 words

Building Trust as a Young Leader

Paige Costello shares her insights on how to garner trust and win over skeptics, especially when you're often the youngest person in the room. She emphasizes the importance of understanding your market, competitors, and product metrics to build credibility and confidence.

"you're often the youngest person in the room what have you learned about how to Garner trust and win over Skeptics the thing I would say is bring the Insight know that I customer Know Thy Market know ..."

2
0:40 - 1:34
0:54 duration164 words

Paige Costello's Journey

In this segment, Paige Costello introduces herself and her role at Asana, detailing her background as a product leader and her previous experiences at Intercom and Intuit. She discusses the importance of building trust with more experienced colleagues and the value of leading by example.

"welcome to Lenny's podcast where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products today my gues..."

3
1:35 - 2:15
0:40 duration120 words

The Evolution of Asana's Product Development

Paige explains how Asana's product development process has evolved over the years, focusing on strategic planning and the importance of clarity in team roles. She highlights the shift from project-based organization to a more problem-focused approach that enhances accountability and agency.

"colleagues and former colleagues and everyone I talk to love Paige you'll soon see why enjoy this episode with Paige Costello after a short word from our sponsors today's episode is brought to you by ..."

4
2:16 - 3:00
0:44 duration116 words

Planning Strategies at Asana

Discussing the planning strategies at Asana, Paige outlines the changes in planning frequency and the introduction of area perspectives. She explains how these changes have improved the precision of their product strategy and the metrics used to measure success.

"independent from the big tech companies its index features billions of pages of high quality data from real humans and it's constantly updated thanks to being the default search engine in the brave br..."

5
3:01 - 3:45
0:44 duration119 words

The Double Diamond Process Explained

Paige introduces the Double Diamond process used at Asana, which emphasizes a systematic approach to problem-solving. She describes how this framework encourages teams to explore broad options before narrowing down to specific solutions, fostering curiosity and rigorous decision-making.

"brave.com Lenny this episode is brought to you by atio a new type of CRM that's powerful flexible and built around your data traditional crms were built for a different era with totally different spee..."

6
3:46 - 4:30
0:44 duration118 words

Metrics and Team Accountability

In this segment, Paige discusses the importance of metrics in Asana's product teams. She shares examples of how teams measure success and ensure that they are delivering real value to users, emphasizing the balance between driving metrics and meeting customer needs.

"model or company stage atio is the CRM for fast growing startups get started today and get 15 off your first year at ezio.com Lenny that's ATT io.com Lenny Paige welcome to the podcast thanks Lenny gr..."

7
12:32 - 13:34
1:01 duration225 words

Understanding the Double Diamond Process

Paige Costello explains the Double Diamond process used at Asana, which emphasizes a systematic approach to product development. This framework encourages teams to explore broad questions about customer needs before narrowing down to specific solutions, fostering curiosity and rigorous decision-making.

"metrics to have as a guard rail to ensure that we're not driving one metric at the expense of people really getting what they need out of Asana just a couple more questions along these lines some nerd..."

8
13:34 - 14:45
1:10 duration180 words

Mapping Artifacts to Decision-Making

In this segment, Paige discusses how Asana maps its product development artifacts to the Double Diamond process. She highlights the importance of customer insights and structured reviews to ensure that product decisions are informed and aligned with user needs.

"people to get out of their um opinion driven lands because so often we really want we we need to be curious quantitatively and and qualitatively about what we're doing and why and be more systematic a..."

9
14:45 - 15:31
0:46 duration140 words

Defining Success Metrics

Paige emphasizes the significance of defining success metrics in product development. She explains how understanding who the product is for and what success looks like is crucial to avoid misleading outcomes and ensure that customer benefits are prioritized.

"way you described it is it was very customer Target oriented is that just is that the actual framework is it around like who to build this for and then what to build or is it more it is yeah it's real..."

10
15:31 - 16:33
1:02 duration164 words

Phases of the Double Diamond

Paige outlines the specific phases of the Double Diamond process, including kickoff, customer selection, and design concept reviews. She explains how these phases guide teams in exploring solutions and refining their approach based on customer feedback.

"problem solved and so there it always starts with enough customer Insight such that we can creatively do what they're trying to do and really inventing on behalf of customers can you maybe repeat if t..."

11
16:33 - 18:01
1:27 duration268 words

Asana's Hybrid Work Culture

In this segment, Paige shares insights into Asana's hybrid work culture post-pandemic. She discusses the balance between in-office collaboration and remote work, highlighting the importance of creating spaces for team interaction and the gradual adjustment back to office dynamics.

"and so that launch review is often just hey you really hears the thing here's what we said here are the past follows most of the time by that time it's already been dog fitting internally for some tim..."

12
18:01 - 20:05
2:03 duration383 words

The Benefits of In-Person Collaboration

Paige reflects on the benefits of in-person collaboration at Asana, noting how casual interactions can lead to valuable discussions and insights. She emphasizes the importance of social relationships for mental health and productivity in the workplace.

"designed from the start we wanted to make sure that we took advantage of what's great about working together as teams and so it's it's been the standard so I I would say what's unique about maybe Asan..."

13
20:05 - 21:01
0:56 duration222 words

Finding Productivity in Remote Work

Paige discusses the challenges and productivity dynamics of remote work, sharing her experiences with 'no meeting' days. She highlights the importance of understanding personal work rhythms and creating environments conducive to deep work.

"opportunities to talk strategy with people you're not forced into a meeting room with has been super beneficial I can say that just just today I was having lunch and sat down with my head of data scie..."

14
21:01 - 22:55
1:53 duration329 words

Building Trust with Skeptics

Paige shares her strategies for building trust and winning over skeptics, particularly when leading more experienced colleagues. She emphasizes the importance of bringing insights, understanding customer needs, and asking great questions to foster credibility.

"it was yeah it was at Airbnb I would encourage you to know your chronotype and to walk that time where you have the most head space to do that work so for me it's warnings say morning what is that I'm..."

15
22:55 - 24:39
1:44 duration264 words

The Trust Equation

In this segment, Paige introduces the 'trust equation' as a framework for establishing credibility and reliability in professional relationships. She discusses the components of trust and how authenticity and self-interest perceptions play a role in gaining trust.

"opportunity that's you're not advocating for that just is is true but I think that's a really tricky and unique thing is not to pretend like you have more experience than you do but to be willing to a..."

16
24:39 - 26:01
1:22 duration239 words

Gaining Customer Insights

Paige emphasizes the importance of gaining firsthand customer insights to build trust and understanding within the organization. She encourages new leaders to engage with customers directly to better grasp their needs and improve product offerings.

"perception of self-interest really can change whether people like how much they trust you in terms of knowing the insight and knowing that customer putting the time I imagine is a big element of that ..."

17
26:01 - 27:39
1:37 duration302 words

Communicating Confidence

Paige discusses how to communicate confidence effectively in leadership roles. She highlights the value of vulnerability, body language, and active engagement in meetings as key elements in conveying confidence and building trust with teams.

"break break up how people are having conversations about what we should do and why and what we shouldn't do and why and it's not about your opinion it's about asking questions and then bringing Insigh..."

18
28:03 - 29:00
0:56 duration168 words

Leading by Example

Paige discusses her approach to mentoring and coaching product managers at Asana by leading through example. She explains the importance of repetition in learning and introduces the '3Es' framework—Experience, Exposure, and Education—as a guide for career growth. This segment emphasizes the value of practical experience and learning from observing others in action.

"this episode is brought to you by round round is the private Network built by Tech leaders for Tech leaders round combines the best of coaching learning and authentic relationships to help you identif..."

19
29:01 - 30:58
1:57 duration340 words

Think Big, Ship Small

In this insightful segment, Paige shares her advice for early-career product managers: 'Think big, ship small.' She encourages aspiring PMs to focus on making incremental progress while keeping the bigger picture in mind. This approach helps avoid getting bogged down in details and fosters a mindset geared towards continuous improvement and innovation.

"from my chats with folks that you work with it's really clear that you put a lot of time and energy into mentoring and coaching PMS on your team and I think probably broadly at Asana and one thing spe..."

20
30:59 - 32:08
1:08 duration180 words

Transformational Leadership Training

Paige reflects on the transformational impact of the '15 Commitments of Conscious Leadership' training that new Asana employees receive. She explains how this training equips them with tools and vocabulary to foster effective collaboration and decision-making. The segment highlights the importance of self-awareness and understanding one's mindset in leadership roles.

"than you will get from just you know what does your day entail from a what work is directly required of you is there an example of that happening either to you or you saw a manager leader do this and ..."

21
32:09 - 33:29
1:19 duration218 words

Answering the Unasked Questions

In this segment, Paige shares a pivotal piece of advice she received during a high-stakes product review: always answer the question that should have been asked. This insight encourages product managers to think strategically and address broader implications rather than just responding to surface-level inquiries, enhancing the quality of discussions and decisions.

"in terms of experiences like sometimes the experience is you doing the thing and getting that experience firsthand other times you you need an education you need a mentor you need a coach who will tel..."

22
33:30 - 35:00
1:30 duration277 words

Avoiding Self-Selection

Paige advises early-career professionals to avoid self-selection, encouraging them to apply for opportunities even if they feel underqualified. She emphasizes the importance of thinking big while shipping small, reminding PMs to maintain a balance between ambition and practicality in their work. This segment serves as a motivational call to action for those hesitant to pursue their goals.

"experience exposure and education really helps you make sure that you're consciously moving forward on each of those fronts or finding people who can help you there I love that piece of advice and it ..."

23
35:01 - 36:36
1:35 duration259 words

Mindset Matters: Above or Below the Line

Paige introduces the concept of being 'above or below the line' in terms of mindset. She explains how being above the line fosters curiosity and openness, while being below the line leads to a more rigid, win-at-all-costs mentality. This segment encourages leaders to cultivate a learning-oriented mindset and recognize the impact of their mental state on decision-making and collaboration.

"of advice that I would say that I I like is more of a way of thinking so this is a little a little abstract but when cut uh when in plays join Asana they get a book called the 15 commitments of a cons..."

24
36:37 - 38:17
1:39 duration291 words

Challenging Scarcity Mindsets

In this segment, Paige shares a personal anecdote about overcoming a scarcity mindset when faced with multiple responsibilities. She illustrates how asking herself, 'How might the opposite be true?' helped her find a more positive and productive perspective. This approach encourages flexibility and creativity in problem-solving, essential traits for effective product leadership.

"it also helped me think about like rejecting false trade-offs and challenging like effectively there's this notion of how might the opposite be true and that's that's a piece of advice that I give mys..."

25
38:18 - 39:39
1:21 duration209 words

Navigating AI in Product Development

Paige discusses the rapid advancements in AI and how Asana is approaching investment in AI exploration. She explains the balance between dedicated AI teams and the broader product team, emphasizing the importance of prototyping and innovation in leveraging AI technologies. This segment highlights the strategic considerations product leaders must make in a fast-evolving tech landscape.

"show up and be curious and like really engage with you on the topics that you've found interesting and we'll just do that and so how might the opposite be true has been a really helpful piece of advic..."

26
39:39 - 40:01
0:21 duration70 words

Empowering Teams with AI

Paige explains how Asana empowers teams to leverage AI by providing them with the necessary tools and hypotheses. This approach fosters a culture of experimentation and skill development, enabling teams to tackle customer challenges effectively.

"to serve with new ways of serving them and so it was a really fun conversation and I also had to be honest with people and say this is a 70 cut 30 of this is missing or incorrect and that's why I'm co..."

27
40:01 - 40:52
0:51 duration149 words

Lessons from Intuit

Reflecting on her time at Intuit, Paige shares valuable insights on customer-centric product management. She highlights the importance of understanding customer needs and behaviors to create impactful products, a principle that remains central to her coaching philosophy.

"our 12-month rolling planning conversation let me pull on this AI thread because it's uh clearly top of mind for a lot of people yeah how do you think about splitting up investment in AI exploration w..."

28
40:52 - 41:36
0:43 duration138 words

The Art of Feedback

Paige discusses the critical skill of delivering feedback effectively. She introduces the Situation-Behavior-Impact framework, which helps managers provide constructive feedback that fosters growth and understanding among team members.

"Norms of how we work so they kind of went straight to prototyping instead of going through that double Diamond I was explaining earlier what that meant was that we were really quickly able to say wow ..."

29
41:36 - 42:18
0:41 duration119 words

Overcoming New PM Challenges

In this segment, Paige identifies common challenges faced by new product managers, such as the pressure to be an expert. She emphasizes the importance of collaboration and curiosity over the need for immediate confidence, encouraging PMs to engage in open dialogue.

"want to do um and so we're able to like nudge people without wasting time and build the skills locally within the teams that then move those experiences forward I'm going to come back to the coaching ..."

30
42:18 - 43:09
0:51 duration142 words

Authenticity in Leadership

Paige reflects on the importance of authenticity in leadership. She shares her journey of learning to communicate challenges and setbacks openly, fostering a culture of trust and transparency within her teams.

"and their training so on the PM front the biggest thing that they taught was around customer centricity and it really started with the founding of the company like if for anyone who works it into it o..."

31
43:09 - 44:02
0:52 duration144 words

Learning from Mistakes

Paige recounts a pivotal moment in her career where she learned the importance of guiding without micromanaging. She discusses how to provide direction that empowers team members while avoiding the pitfalls of overbearing leadership.

"create products around they also are very specific about how they Define a durable advantage and think about overall like the the product process from a place of customer Insight through to like the m..."

32
44:02 - 44:55
0:53 duration148 words

Balancing Optimism and Realism

In this segment, Paige shares her experience of balancing optimism with the need for realism in leadership. She discusses how acknowledging challenges can enhance team dynamics and foster a more authentic work environment.

"don't set up your your teammates your teams for growth or success in their careers and so their their program for helping you think about like okay I'm gonna convey this feedback as situation Behavior..."

33
44:55 - 45:53
0:58 duration171 words

Intentional Career Planning

Paige discusses her approach to career planning, focusing on skills and experiences rather than specific roles. She emphasizes the importance of evaluating learning curves and ensuring a supportive environment for personal and professional growth.

"format and framing really helped me understand that delivering feedback isn't about being right or about getting the right information to the other person it's about sharing the impact of different de..."

34
45:53 - 46:43
0:50 duration132 words

Creating a Supportive Environment

Paige highlights the significance of a positive work environment in career development. She stresses the need for supportive colleagues and advocates who can help navigate challenges and foster growth within teams.

"so you've worked with a lot of early product managers I'm curious what you find most holds back new PMS in help being successful in their career and even on the flip side what most helps new PMS be su..."

35
51:38 - 52:40
1:01 duration179 words

Communicating Incompleteness

Paige Costello shares her approach to communication in leadership, emphasizing the importance of being transparent about uncertainties. She discusses how she openly acknowledges when her work is incomplete, fostering a culture of honesty and collaboration within her team. This segment highlights the significance of balancing optimism with realism in leadership communication.

"what I was saying or if we were saying the same things that was really an interesting experience um yeah there are just so many yeah with that second lesson is there something you've changed in the wa..."

36
52:40 - 54:23
1:43 duration268 words

Intentional Career Planning

In this segment, Paige discusses her intentional approach to career planning, focusing on skills and experiences rather than specific roles or companies. She emphasizes the importance of evaluating one's learning curve and the work environment to ensure personal growth and fulfillment. Paige shares insights on how to assess whether one is on the right career path.

"I'm curious how you think about your career going forward how far out do you think where you want to be and how do you kind of plan out the future of Paige's career I try to be really intentional abou..."

37
54:23 - 55:17
0:54 duration170 words

Finding Passion in Problems

Paige Costello reflects on the idea that passions are cultivated through experiences rather than found. She encourages exploring different problems to discover what is interesting and engaging. This segment underscores the importance of curiosity in product management and how it can lead to better job performance.

"work and then the third piece is really around just the problem the problem your product is solving is it fun is it interesting I often like to think about like passions are made not found because I t..."

38
55:17 - 56:11
0:53 duration160 words

Lightning Round: Book Recommendations

In a quick-fire lightning round, Paige shares her top book recommendations for product managers, highlighting 'Inspired' by Marty Kagan as a classic. She also mentions 'The Blind Assassin' by Margaret Atwood and 'The Alchemist' by Paulo Coelho, providing insights into why these books resonate with her and their relevance to product management.

"are things that I use to assess like am I still on the right path or should I consider an alternative but when I think about my own career I really think about skills and experiences as opposed to rol..."

39
56:11 - 57:32
1:21 duration231 words

Interview Insights: Learning from Failure

Paige discusses her favorite interview question that probes candidates about past failures. She explains how this question reveals a candidate's mindset and problem-solving approach, emphasizing the importance of resilience and learning from mistakes in product management.

"what is a favorite recent movie or TV show ooh I'm very much enjoying the Diplomat right now and then TV show or a movie let's see I just watched the fire of Love documentary which is about a couple w..."

40
57:32 - 58:38
1:06 duration171 words

Exploring New Product Innovations

In this segment, Paige shares her recent exploration of the product 'Poe.com,' a chatbot that allows users to learn about large language model capabilities. She discusses her excitement about creating a page bot and the potential for AI to enhance product management practices.

"what is a favorite product that you've recently discovered that you love I've been playing a lot with poe.com lately just an opportunity to learn more about llm capabilities in a first-hand way it's b..."

41
58:38 - 1:01:03
2:24 duration439 words

Streamlining Product Development Processes

Paige outlines a significant change in her product development process that has improved team efficiency. She emphasizes the importance of clear ownership in reviews and approvals, advocating for a streamlined approach that empowers teams and accelerates decision-making.

"there's also a lennybot.com for folks that haven't seen this somebody built actually there's a whole post on my newsletter of how how it was built and you go to lennybot.com and it is trained on all o..."

42
1:01:03 - 1:02:02
0:59 duration159 words

Asana Pro Tips for Effective Meetings

Paige shares her favorite Asana pro tip for managing meetings effectively. She explains how she uses Asana to assign pre-reads and take live notes during meetings, ensuring that action items are captured and tracked efficiently. This segment highlights practical strategies for leveraging tools to enhance team collaboration.

"stage got it informed people stakeholders decision makers okay great final question you work at Asana what is your favorite Asana Pro tip I use Asana to run all my meetings and assign pre-reads so I u..."

43
1:02:02 - 1:03:10
1:07 duration206 words

Engaging with the Community

In the closing segment, Paige invites listeners to connect with her on LinkedIn and Twitter. She expresses her interest in hearing thoughts on how AI can shape the future of software for knowledge workers, particularly in relation to Asana. This segment emphasizes the importance of community engagement and feedback in product development.

"awesome thank you so much for doing this two final questions where can folks find you online if they want to reach out and learn more and how can listeners be useful to you you can find me on LinkedIn..."