Episode Summary: How to Ask the Right Questions, Project Confidence, and Win Over Skeptics | Paige Costello

In this insightful episode of Lenny's Podcast: Product | Growth | Career, host Lenny Rachitsky converses with Paige Costello, a seasoned Product Lead at Asana with a rich background that includes leadership roles at Intercom and Intuit. Released on July 9, 2023, this episode delves deep into Paige’s strategies for building trust, fostering confidence, and effectively managing product development in a fast-paced tech environment.

1. Building Trust and Winning Over Skeptics

Timestamp: [00:07]

Paige emphasizes the importance of bringing insights to the table. She advises new product managers (PMs) to thoroughly understand their customers, market, competitors, numbers, and the product itself. By being the person who has conducted extensive customer research and possesses a clear viewpoint, PMs can naturally earn trust and pique the curiosity of more experienced or skeptical colleagues.

Paige Costello: "Know thy customer, know thy market, Know thy competitors, know thy numbers, know thy product." ([00:07])

She further elaborates on the trust equation, combining credibility, reliability, and authenticity while minimizing the perception of self-interest. This framework, inspired by insights from Ann Raymondi, highlights that trust is built not just by expertise but by consistent, authentic interactions.

Paige Costello: "Trust is equal to credibility plus reliability plus authenticity divided by perception of self-interest." ([23:34])

2. Overcoming the Scarcity Mindset

Timestamp: [00:19]

When discussing common challenges faced by new PMs, Paige identifies the scarcity mindset—the tendency to see limited options or paths forward—as a significant barrier. She shares her personal breakthrough by challenging herself with the question, "How might the opposite be true?", which alleviated her anxiety and opened up new possibilities.

Paige Costello: "My brain is so accustomed to having a scarcity mindset... the moment I challenged myself and said how might the opposite be true? My shoulders dropped. I felt more relaxed." ([00:19])

3. Evolution of Product Development at Asana

Timestamp: [06:00]

Asana’s product development process has undergone substantial changes under Paige’s leadership. Initially organized around projects and locations, Asana transitioned to a more structured approach involving Pillars, Areas, and Teams. This reorganization fosters agency and accountability, aligning teams closer to specific customer segments and problem areas.

Pillars and Areas

• Pillars represent broad strategic categories (e.g., Core Product, Adoption and Enterprise Scale, Workflow).
• Areas are subgroups within each pillar, targeting specific customer needs and problem spaces.
• Teams focus on executing within these areas, driving measurable outcomes through well-defined metrics.

Paige Costello: "We have pillar metrics, area metrics, and then at the team level, there's often like one or two that they're really driving forward." ([07:23])

Strategic Planning

Paige highlights the shift from annual planning to a rolling 12-month plan with six-month reviews. This allows Asana to remain agile, adapting to new opportunities and technological advancements without being locked into long-term plans that may become obsolete.

Paige Costello: "We plan every six months because it gives our business more confidence in what's coming and a better opportunity to align our go-to-market and product planning." ([09:10])

4. Implementing the Double Diamond Process

Timestamp: [13:00]

Asana employs the Double Diamond Process, a framework that encourages teams to explore broadly before narrowing down to specific solutions. This method ensures that product development is customer-centric and rigorous, moving beyond opinion-based decisions to data-driven outcomes.

Phases of the Double Diamond

1. Discover: Broad exploration to understand customer needs.
2. Define: Narrowing focus to specific problems.
3. Develop: Expanding potential solutions.
4. Deliver: Finalizing and launching the best solution.

Paige Costello: "The double diamond process that Asana effectively each of our typical reviews or artifacts sit at different inflection points on the double diamond." ([14:44])

This structured approach aids in maintaining clarity and alignment across teams, ensuring that every product decision is backed by substantial customer insight and strategic thinking.

5. Asana’s Work-from-Home Policy

Timestamp: [17:42]

Paige describes Asana’s office-centric hybrid model, designed to balance the benefits of remote work with the advantages of in-person collaboration. The current policy mandates office presence on Mondays, Tuesdays, and Thursdays, with remote work permitted on Wednesdays and Fridays.

Paige Costello: "We're in the office Monday, Tuesday, Thursday and then work from home mostly on Wednesdays and Fridays." ([17:42])

This structure was intentionally established to foster team cohesion and spontaneous interactions, which are often lost in fully remote setups. The hybrid model has evolved to cultivate a more vibrant office environment, encouraging casual conversations and organic collaboration.

6. Projecting Confidence and Effective Communication

Timestamp: [26:36]

Confidence, according to Paige, stems from bravery, vulnerability, and effective communication. She advises PMs to:

• Show up and speak before fully ready, demonstrating courage.
• Be transparent about uncertainties or incomplete aspects of a project.
• Engage fully in meetings, maintaining eye contact and active listening.

Paige Costello: "Real confidence is often conveyed by being willing to ask the question or to say, I don't know what you mean by that." ([26:36])

Paige underscores the importance of body language and active presence in meetings, suggesting that being engaged and open fosters trust and conveys genuine confidence.

7. Coaching PMs and Leading by Example

Timestamp: [29:34]

Paige is a strong advocate for experiential learning and leading by example. She implements the Three E’s Framework—Experience, Exposure, and Education—to guide the development of her team:

• Experience: Hands-on involvement in projects and leadership roles.
• Exposure: Observing and analyzing different aspects of the business without direct control.
• Education: Continuous learning through reading, mentorship, and training.

Paige Costello: "There's a framework called the three E's Experience, Exposure and Education... [it] really helps you make sure that you're consciously moving forward on each of those fronts." ([29:34])

By embodying the behaviors and practices she expects from her team, Paige ensures that lessons are internalized through repetition and modeling, fostering a culture of continuous improvement and proactive learning.

8. Career Lessons and Managing Mistakes

Timestamp: [49:15]

Paige candidly shares her missteps in management, highlighting the delicate balance between providing guidance and avoiding micromanagement. She emphasizes the importance of delivering constructive feedback using the Situation-Behavior-Impact (SBI) framework, which focuses on objective observations and personal impacts rather than subjective judgments.

Paige Costello: "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 decisions that they're making." ([45:35])

Additionally, Paige discusses the challenges of maintaining authenticity while being inherently optimistic. She learned to communicate real-time issues without losing her positive outlook, ensuring her team remains informed and aligned without feeling disheartened.

Paige Costello: "I try to be more real with myself and others. I try to show up and say, like, hey, this is incomplete." ([52:00])

9. Career Planning and Growth

Timestamp: [52:50]

Paige approaches her career with intentionality, focusing on acquiring skills and experiences rather than merely seeking new roles or titles. She assesses her current position by evaluating:

• Learning Curve: Is her role challenging enough to foster growth?
• Environment: Does the workplace support her development with the right resources and a positive culture?
• Problem Alignment: Is the work engaging and aligned with her interests?

Paige Costello: "I really think about skills and experiences as opposed to roles or companies or specific problems." ([52:50])

This strategic approach ensures that her career progression is aligned with her personal and professional growth objectives, allowing her to remain adaptable and fulfilled.

10. Lightning Round Highlights

Timestamp: [55:44]

In the lightning round, Paige shares some of her personal favorites and professional preferences:

• Books:
  • Inspired by Marty Cagan – A staple recommendation for PMs.
  • The Blind Assassin by Margaret Atwood
  • The Alchemist by Paulo Coelho

Paige Costello: "My go to book Recommendation for other PMs is inspired by Marty Kagan." ([55:54])

• TV Shows/Movies:

  • Currently enjoying The Diplomat.
  • Recently watched the documentary Fire of Love about volcanoes.

• Interview Questions:

  • Prefers asking candidates about times when something went wrong to assess their problem-solving and mindset.

Paige Costello: "I like to ask, tell me about a time something went wrong. What was it? What did you do about it?" ([56:49])

• Favorite Products:
  • Enjoys experimenting with poe.com to explore LLM capabilities and create bots.

Paige Costello: "I've been playing a lot with poe.com lately... it's been fun to create little bots." ([57:37])

• Asana Pro Tip:
  • Utilizes Asana to manage meetings and assign pre-reads effectively using the multi-assign feature in subtasks.

Paige Costello: "I use Asana to run all my meetings and assign pre reads." ([61:11])

11. Final Thoughts and How to Connect

As the episode concludes, Paige shares her enthusiasm for the ongoing technological transformations, particularly regarding LLMs (Large Language Models), and expresses eagerness to integrate AI to enhance efficiency and alignment within teams.

Paige Costello: "We really have lots of interesting paths forward and are trying to make sure that we're on the cutting edge while really looking at what does it mean to serve the companies and organizations that we want to serve." ([38:52])

For listeners interested in connecting with Paige or contributing insights on AI in software for knowledge workers, she can be found on LinkedIn and Twitter (@PageNow).

Notable Quotes

• Paige Costello: "Knowledge of thy customer, know thy market..." ([00:07])
• Paige Costello: "How might the opposite be true?" ([00:19])
• Paige Costello: "Real confidence is often conveyed by being willing to ask the question." ([26:36])
• Paige Costello: "Trust is equal to credibility plus reliability plus authenticity divided by perception of self-interest." ([23:34])
• Paige Costello: "Don't self select... think big ship small." ([33:58])

Conclusion

This episode offers a treasure trove of actionable insights for product managers and leaders aiming to enhance their strategic thinking, foster team trust, and navigate the complexities of product development in a dynamic environment. Paige Costello’s experiences and methodologies provide a roadmap for aspiring PMs to build impactful careers while driving meaningful product innovations.

For those looking to implement these strategies, Paige’s emphasis on customer-centricity, structured planning, and authentic leadership serves as a foundational guide to achieving excellence in product management.