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

How to Garner Trust and Win Over Skeptics

In this section, the speaker discusses strategies for gaining trust and winning over skeptics in professional settings.

Insight and Knowledge as Key Factors

• Bringing insight, customer knowledge, market understanding, competitor awareness, and product expertise are essential for building trust.

Overcoming a Scarcity Mindset

• Challenging oneself to consider alternative options and different paths can help overcome a scarcity mindset. Embracing the idea of "how might the opposite be true" can lead to more relaxed thinking.

• By realizing that it is possible to do both things successfully, one can alleviate self-imposed limitations.

Interview with Paige Costello

This section introduces Paige Costello as the guest for the interview.

Background of Paige Costello

• Paige Costello is a product lead at Asana, responsible for overseeing teams focused on the core product experience. She has previous experience as a director of product at Intercom and as a group product manager at Intuit.

Topics Covered in the Interview

• Strategies for building trust with more experienced or older individuals

• Coaching techniques for product managers

• Asana's product development process

• Lessons learned from product and career missteps

Sponsorship by Brave Search API

This section highlights sponsorship by Brave Search API.

Introduction to Brave Search API

• Brave Search API is an independent global search index that provides high-quality data for training AI models and powering AI applications. It offers a competitive alternative to Bing or Google, with intuitive structuring and affordable costs.

Sponsorship by Atio CRM

This section highlights sponsorship by Atio CRM.

Introduction to Atio CRM

• Atio CRM is a powerful and flexible CRM solution built around your unique workflows and data structures. It offers real-time dynamic reporting, automatic data enrichment, and the ability to build and adapt your CRM on the fly.

Interview with Paige Costello (Continued)

The interview with Paige Costello continues.

Input from Colleagues

• Questions and suggestions for the interview were provided by colleagues of Paige Costello, including Jackie Bavaro, Yasmin, Montgomery, and Steve Morinasana.

Role at Asana

• Paige leads the product organization at Asana responsible for desktop web and mobile apps. The goal is to help teams work together more efficiently and achieve their desired outcomes through features like goals, portfolios, projects, tasks, and reporting.

The transcript continues beyond this point but does not provide any additional relevant information for note-taking purposes.

Evolution of Product Development at Asana

In this section, the speaker discusses the changes in the product development process at Asana over the years.

Changes in Planning and Strategy

• The planning process at Asana has evolved in terms of altitudes, time horizons, and inputs.

• There are now more precise and opinionated inputs for strategy setting and planning.

• Pillar plans and team plans have always existed, but an intermediary layer called "area perspective" has been added to create more agency and accountability.

• The organization is reorganized to have teams focused on specific target customers and problems.

Structure of Asana's Organization

• Asana is organized into pillars (e.g., core product pillar, adoption and enterprise scale pillar, workflow pillar).

• Each pillar consists of subgroups called areas that focus on specific target customers and problem spaces.

• Different levels of metrics are used to measure success at the R&D level, pillar level, area level, and team level.

Shift from Project-Focused to Problem-Focused Approach

• Previously, Asana was organized around projects and locations. Now it focuses on durable problem-focused thinking.

• Roadmaps are no longer about features but about tackling what is most meaningful for business growth.

Changes in Time Horizon for Planning

• Initially, annual planning was primarily done. Now planning is done every six months for a rolling 12-month period.

• This allows better alignment between go-to-market strategies and product planning.

Benefits of Frequent Reflection on Plans

In this section, the speaker explains why frequent reflection on plans is important for successful product development.

Agility in Response to Change

• Reflecting on plans frequently allows quick pivoting when something changes or new opportunities arise.

• It reduces the feeling of churn and thrash and makes the team more principled in decision-making.

Leveraging Faster Progress and New Opportunities

• Sometimes, progress is made faster than anticipated, or new technologies emerge.

• Frequent reflection on plans helps identify these opportunities and allows the team to go bigger on them.

Making the Best Use of Teams

• Reflecting on plans frequently ensures that teams are making the best use of their resources.

• It helps prioritize work based on what will have the most impact.

Detailed Roadmap and Prototyping

In this section, the speaker discusses how Asana approaches detailed roadmaps and prototyping.

Alignment on Success Criteria

• Instead of having quarterly plans or sprints, Asana focuses on aligning teams around success criteria.

• The teams ship as quickly and iteratively as possible to achieve those criteria.

Encouragement of Prototyping

• Asana encourages prototyping and acknowledges that some items may be pivoted or cut from the roadmap if necessary.

• This approach allows for flexibility in responding to user feedback or changing priorities.

Metrics for Asana Teams

In this section, the speaker discusses metrics that are important for teams at Asana.

Metrics for the Coordinate Team

• The Coordinate team at Asana focuses on ensuring that the slice of Asana used by teams to work together is effective.

• Some metrics that the Coordinate team cares about include weekly active users and healthy project use.

• The goal is to understand what good looks like and create a dynamic where people get real value from using Asana.

The Double Diamond Process

This section explains the Double Diamond process used at Asana for product development.

What is the Double Diamond Process?

• The Double Diamond process involves going broad and then narrowing down when solving problems.

• It starts with asking which customer to solve for (going broad) and then identifying their problems (narrowing down).

• Next, it involves determining possible solutions (going broad) and selecting the best solution (narrowing down).

• This process helps in making data-driven decisions and being more systematic in problem-solving.

Customer-Oriented Framework of the Double Diamond Process

This section explores how the Double Diamond process at Asana is customer-oriented.

Customer Target Orientation in the Framework

• The Double Diamond process at Asana emphasizes understanding who to build a product or feature for.

• By focusing on customers, it becomes clear what success looks like beyond just using a feature.

• Planning processes define categories and how to win, while individual projects focus on solving specific problems for customers.

Inflection Points in the Double Diamond Process

This section highlights different inflection points within the Double Diamond process at Asana.

Inflection Points in Product Development

1. Kickoff: Gathering information broadly and selecting a target customer.

2. Customer and Direction Selection: Identifying the path to pursue in solving the problem.

3. Design Concept Review: Going broad within the chosen path and exploring different concepts.

4. Full Experience Review: Evaluating the end-to-end experience of the product or feature.

5. Launch Review: Ensuring readiness for launch, including metrics and final adjustments.

Conducting Reviews in the Double Diamond Process

This section discusses how reviews are conducted during the Double Diamond process at Asana.

Review Formats

• The format of reviews depends on the complexity and ambiguity of the solution being developed.

• Crits (critiques) often happen in person for design-related aspects, while spec reviews are more asynchronous.

• Meetings or asynchronous discussions are determined based on the number of questions and level of complexity.

The transcript is already in English, so there is no need to translate it.

Asana's Office Policy and Changes

The speaker discusses Asana's office policy and how it has changed over the past couple of years.

Asana's Hybrid Office Format

• Asana was fully remote during the pandemic but has now adopted an office-centric hybrid format.

• Employees work in the office on Monday, Tuesday, and Thursday, and work from home mostly on Wednesdays and Fridays.

• This dynamic was designed to take advantage of the benefits of working together as teams.

Embracing an Office-Centric Approach

• Asana made a deliberate decision to be an office-centric hybrid workplace from the beginning.

• They wanted to create spaces for people to work together and move quickly.

• It took some time for employees to adjust to being back in the office, but there is now more vibrancy, conversation, and casual interactions.

Benefits of Being in the Office

• Being in the office allows for social casual relationships and more opportunities for spontaneous discussions outside of formal meetings.

• It positively impacts mental health by providing a balance between social interactions and deep work.

• The speaker shares a personal experience of having impromptu conversations with colleagues that might not have happened if they had to schedule a meeting.

Reverting Back to Pre-Pandemic Ways

• The current hybrid model feels similar to pre-pandemic days when there were no meetings scheduled, allowing for focused work from home.

• People are adapting well to this new way of working, with remote days becoming more impactful while in-person days foster collaboration.

Building Trust as a Young Leader

The speaker discusses their experience as a young leader leading individuals with decades more experience. They share insights on how to garner trust and win over skeptics.

Importance of Insight and Knowledge

• To gain trust as a young leader, it is crucial to bring insight and knowledge about the customers, market, competitors, and product.

• Having a deep understanding of the product and being able to articulate why certain tools are better or worse in specific dimensions builds credibility.

Confidence in Sharing Insights

• Young leaders don't need to have expertise in every functional domain but should be confident in sharing their insights.

• By bringing unique perspectives and making others curious, trust can be established even with skeptics who have more experience.

Asking Great Questions

• It is essential for young leaders to ask great questions rather than pretending to have more experience than they do.

• Being willing to learn from others and seeking input from experts in different domains helps build trust and credibility.

The transcript provided does not specify the language used. Therefore, the summary has been written in English.

New Section

In this section, the speaker discusses the concept of trust and its components: credibility, reliability, authenticity, and perception of self-interest. They emphasize the importance of creating credibility when meeting someone new and how bringing insight can help build trust.

Building Trust

• Trust is equal to credibility plus reliability plus authenticity divided by perception of self-interest.

• When meeting someone new, focus on creating credibility by bringing insight.

• Reliability is important in building trust.

• Authenticity involves being vulnerable and genuine.

• Perception of self-interest can impact trust levels.

Understanding Customers

• Spending time with customers firsthand is crucial for understanding their needs and behaviors.

• Observing customers using the product provides valuable insights that may differ from reported data or studies.

• Breaking away from internal perspectives and heavy "dog fooding" cultures helps maintain sensitivity to customer needs.

Communicating Confidence

• Confidence is conveyed through bravery, courage, vulnerability, and asking questions.

• Being open and attentive during meetings conveys confidence more effectively than assertiveness alone.

• Non-verbal communication such as eye contact and body language also play a role in conveying confidence.

New Section

In this section, the speaker introduces Round as a private network designed for tech leaders to connect, learn, and grow together.

Round - Private Network for Tech Leaders

• Round is a private network created by tech leaders for tech leaders.

• It combines coaching, learning, and authentic relationships to support personal and professional growth.

• Round aims to shape the future of technology and its impact on society.

• Building and managing a network within Round provides opportunities for learning, finding new opportunities, and achieving goals.

New Section

In this section, the speaker discusses the importance of mentoring and coaching product managers (PMs) at Asana. They emphasize leading by example as an effective approach to teaching and guiding others.

Leading by Example

• The speaker invests significant time and energy into mentoring and coaching PMs at Asana.

• Leading by example is a key aspect of their approach.

• It involves demonstrating how things are done rather than simply explaining them.

• This approach is believed to be more successful in guiding PMs towards growth and development.

The Three E's Framework for Career Growth

In this section, the speaker discusses a framework called the three E's - experience, exposure, and education - as a way to grow one's career and be more purposeful about personal growth.

The Three E's Framework

• Experience: Gaining practical experience is important for career growth.

• Exposure: Being present, analytical, and learning from the environment can lead to significant growth in various directions.

• Education: Continuous learning through formal education or mentorship/coaching is crucial for personal development.

Examples of Applying the Three E's

• Running Meetings: The speaker ensures that their meetings reflect the kind of meetings they want to be a part of. They focus on clear agendas, productive conversations, and creating a positive experience for everyone involved.

• High-Stakes Product Review: During a product review session, the leader advised always answering the question that should have been asked. This approach helps address bigger picture considerations and alternative perspectives.

Impactful Advice for Career Growth

In this section, the speaker shares advice that has been impactful in their own career journey and offers common pieces of advice to their team members.

Advice for Early Career Professionals

• Avoid Self-selection: Encourage early-career professionals not to self-select out of opportunities due to perceived lack of experience or qualifications.

• Think Big, Ship Small: Emphasize thinking big while taking small steps towards achieving goals. Avoid getting too caught up in incremental optimizations at the expense of broader vision.

Conscious Leadership Approach

• "The 15 Commitments of a Conscious Leader": A book recommended by Asana for new employees that focuses on conscious leadership principles.

• Above vs Below the Line Thinking: Being above the line means being open, curious, and committed to learning. Being below the line indicates a closed mindset and resistance to growth.

Additional Advice and Training

In this section, the speaker shares additional advice and training that has been impactful in their career journey.

Additional Advice

• Don't Self-select: Encourage individuals not to limit themselves based on perceived limitations.

• Think Big, Ship Small: Emphasize the importance of balancing ambitious thinking with practical execution.

Conscious Leadership Training

• Asana provides new employees with a book called "The 15 Commitments of a Conscious Leader" and two-day training on effective collaboration techniques.

• Above vs Below the Line Thinking: The training introduces the concept of above vs below the line thinking, emphasizing the importance of maintaining an open and growth-oriented mindset.

The transcript provided does not contain timestamps for all sections.

Personal Headspace and Mindfulness

The speaker reflects on the advice they received about being mindful of their personal headspace and how it affects their decision-making. They also discuss the importance of recognizing others' perspectives and rejecting false trade-offs.

Being mindful of personal headspace

• Recognizing the impact of personal headspace on decision-making.

• Importance of understanding one's own operating state.

• Reflecting on how personal headspace affects decision-making.

Recognizing others' perspectives

• Considering the context and mindset of others when making decisions.

• Understanding the importance of empathy in decision-making.

• Challenging false trade-offs and exploring alternative options.

The power of questioning

• Using the question "How might the opposite be true?" to challenge assumptions.

• Overcoming a scarcity mindset by considering different paths or options.

• Feeling more relaxed and open-minded by challenging oneself with alternative perspectives.

Product Leadership in Times of Technological Transformation

The speaker discusses the role of product leadership during a time of technological transformation, particularly in relation to serving companies and organizations with new ways of meeting their needs.

Technological transformation in llms

• Astonishing pace of technological development in llms (learning management systems).

• Ability to ship quickly and deliver intelligent solutions.

• Focus on serving companies and organizations with new approaches.

Clarity pillars strategy

• Delivering clarity pillar briefs to area leads.

• Ensuring understanding of strategic priorities, metrics, and usability plans.

• Establishing perspective, documenting plans, and encouraging open dialogue.

Investment in AI Exploration within Product Team

The speaker discusses how investment in AI exploration is approached within the product team, including the involvement of dedicated teams and integrating AI into various product areas.

AI exploration within the product team

• Existence of an ML team for test prioritization and notification models.

• Staffing a dedicated team for prototyping and exploring possibilities in llms.

• Skipping traditional processes to quickly prototype and discover unexpected improvements.

Integrating AI expertise

• Giving teams with expertise in customer problems ownership of AI integration.

• Providing starter hypotheses and progress reporting for experimentation.

• Nudging teams without wasting time and building local skills.

Customer Centricity in Product Management

The speaker reflects on their experience at Intuit, known for its strong APM program, and highlights the importance of customer centricity in product management. They also mention the APN program at Asana.

Learnings from Intuit's APM program

• Emphasis on customer centricity as a core value.

• Foundational focus on understanding customers' needs.

• Bringing customer-centric mindset to coaching and product management roles.

Training programs at Intuit and Asana

• Recognition of Intuit's reputation for excellent APM training.

• Mention of Asana's APN program as another example of effective training.

Understanding Customer Behavior and Feedback

In this section, the speaker discusses the importance of observing and understanding customer behavior to build successful products. They also highlight the significance of delivering effective feedback.

Observing Customer Behavior

• Collect artifacts and observe customers using your product to gain insights for building better products.

• Pay attention to workarounds and use that experience to identify opportunities for innovation.

Importance of Feedback

• Delivering feedback is critical for managers as it sets up teammates for growth and success in their careers.

• Use a structured approach when giving feedback, such as conveying the situation, behavior, and impact.

• Feedback should focus on sharing the impact of different decisions rather than being right or providing information.

• Formalizing feedback helps create clarity and engagement within teams.

Challenges and Success Factors for New Product Managers

In this section, the speaker discusses common challenges faced by new product managers (PMs) and factors that contribute to their success.

Challenges Faced by New PMs

• The illusion of needing to be all-knowing and super confident can hinder PMs from adopting an inquiry-based approach.

• Trying to be a "Pro" too quickly can lead to reduced information sharing and collaboration.

• Avoid being performative in collaboration; instead, embrace true curiosity and openness.

Success Factors for New PMs

• Be present, ask clarifying questions, seek feedback, and engage in conversations that move relationships forward.

• Don't let ambition and career-centric focus overshadow the importance of enjoying the job and solving problems.

• Let your outcomes speak for themselves, and others will recognize your contributions.

The transcript provided is in English, so the notes are also written in English.

Lessons Learned from Moving into a Management Role

In this section, the speaker reflects on their experience transitioning from an individual contributor (IC) to a management role and shares valuable lessons learned.

Giving Guidance without Micromanaging

• One challenge faced in a management role is providing guidance and direction without micromanaging.

• The speaker emphasizes the importance of teaching repeatable patterns instead of giving precise instructions that can only be used once.

• They suggest using techniques like writing down thoughts on Post-it notes during meetings to ensure effective communication without being overly controlling.

Balancing Optimism and Realism

• The speaker acknowledges their natural inclination towards optimism but highlights the need to balance it with realism in certain situations.

• Depending on the team or organizational culture, it may be necessary to address and discuss negative aspects or challenges openly.

• They share an experience where they unintentionally appeared inauthentic by not addressing concerns or problems due to their optimistic nature.

Being Real and Transparent

• The speaker discusses the importance of being real and transparent with oneself and others.

• They give an example of how they communicate incomplete work or uncertainties, allowing for open discussions about improvement areas.

• By being honest about both small and big issues, people can have a balanced perspective of one's work and contribute effectively.

Planning Career Growth with Intentionality

In this section, the speaker talks about their approach to career planning and growth, focusing on skills, learning curves, environment, and problem-solving interests.

Evaluating Learning Curve in a Role

• Instead of solely considering roles or companies, the speaker evaluates their career based on learning curves and personal growth opportunities.

• They emphasize the importance of feeling challenged and continuously learning in a role, even if other aspects are favorable.

Considering the Impact of Environment

• The speaker highlights the significance of the work environment in career growth.

• Factors such as staffing, toxic team members, or inadequate resources can impact one's ability to make an impact and grow professionally.

• They stress the need for an environment that includes advocates and provides the right ingredients for success.

Passion for Problem-Solving

• The speaker encourages exploring different problems and evaluating personal interest in them.

• They suggest that passion is developed through curiosity and finding problems that are interesting or fun to solve.

• It is not necessary for a problem to be glamorous or associated with a well-known company; what matters is genuine curiosity and dedication to doing good work.

The transcript provided does not contain any additional sections.

Lightning Round: Book Recommendations, Favorite Movie/TV Show, Interview Questions, Product Discovery, Process Improvement, Asana Pro Tip

In this lightning round segment of the transcript, the speaker answers a series of questions related to book recommendations, favorite movie/TV show, interview questions, favorite product discovery, process improvement in product development, and an Asana pro tip.

Book Recommendations

• The speaker's go-to book recommendation for other PMs is "Inspired" by Marty Kagan.

• Other books recently enjoyed and recommended are "The Blind Assassin" by Margaret Atwood and "The Alchemist" by Paulo Coelho.

Favorite Movie/TV Show

• The speaker is currently enjoying watching the TV show called "The Diplomat".

• They also recommend watching the documentary "Fire of Love", which is about a couple studying volcanoes.

Favorite Interview Question

• The speaker likes to ask candidates about a time when something went wrong and how they handled it. This question helps evaluate their problem-solving skills and mindset.

Favorite Product Discovery

• The speaker has been exploring poe.com lately to learn more about LLM capabilities firsthand. They mention playing with creating a page bot on poe.com.

Process Improvement in Product Development

• One major process improvement implemented was being clear about the number of reviews and approvals required for a task or project.

• They limited the number of people involved in each review meeting and assigned one person as the final decision-maker to increase efficiency and accountability.

Asana Pro Tip

• The speaker uses Asana to run meetings and assign pre-reads.

• They frequently use the multi-assign feature in subtasks to assign tasks with due dates quickly.

Timestamps have been provided for each section based on available information from the transcript.

Introduction and Contact Information

In this section, the speaker introduces themselves and provides contact information for further engagement.

Speaker Introduction and Contact Information

• The speaker can be found online on LinkedIn and Twitter as Paige Costello.

• LinkedIn: Paige Costello

• Twitter: @paigenow

How Listeners Can Be Useful

• Listeners are encouraged to share their thoughts on how they think AI will shape the future of software for knowledge workers.

• Specifically, if listeners and their teams use Asana, the speaker would like to know where they would like to see AI playing a bigger role in driving efficiency and alignment for their team's work.

Opportunities with AI in Asana

In this section, the speaker discusses the opportunities for AI in Asana and invites feedback from users.

Opportunities with AI in Asana

• Asana offers goal management and work management features that help teams collaborate effectively.

• The speaker is interested in hearing from users about where they see opportunities for AI to play a bigger role in driving efficiency and alignment within their teams.

Conclusion and Call to Action

In this section, the speaker concludes the conversation and provides instructions for listeners.

Conclusion and Call to Action

• The speaker thanks the audience for listening.

• If listeners found the content valuable, they are encouraged to subscribe to the podcast on Apple Podcasts, Spotify, or their favorite podcast app.

• Leaving a rating or review is appreciated as it helps other listeners discover the podcast.

• All past episodes can be found on the podcast's website for further reference or learning.

The transcript provided does not contain any content that is not in English.