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

1. Bring the Insight

To gain trust and convince skeptics, especially when younger or less experienced, focus on bringing deep insight by thoroughly knowing your customer, market, competitors, numbers, and product. This creates credibility and makes people curious and trusting.

2. Build Credibility & Reliability

Build trust by focusing on credibility (bringing insight), reliability (your say-do ratio), and authenticity (being vulnerable). Ensure people perceive you as not acting out of self-interest, as this can significantly impact trust.

3. Challenge Scarcity: “Opposite True?”

When feeling overwhelmed or constrained by a scarcity mindset, ask yourself, “How might the opposite be true?” This question can help break mental frames, create alternative options, and reveal different paths, reducing stress and opening possibilities.

4. Operate Above the Line

Be mindful of your headspace: operate “above the line” by being committed to learning, open, curious, and playful. Avoid operating “below the line,” which is characterized by being committed to winning, being right, and seeing things as black and white.

5. Utilize Experience, Exposure, Education

Grow your career purposefully by focusing on three “E’s”: gaining direct Experience, seeking Exposure (observing and evaluating from the passenger seat), and pursuing Education (reading, mentors, coaches). Exposure is particularly important for rapid, multi-directional growth.

6. Answer the Unasked Question

In meetings or conversations, always answer the question that should have been asked, not just the one posed. This demonstrates a higher strategic altitude, covers the bigger picture, and considers alternatives the questioner might have missed.

7. Give Effective Feedback

When giving feedback, use the “Situation-Behavior-Impact” framework: describe the specific situation, the observed behavior, and the subjective impact it had on you. This makes feedback clear, actionable, and less about being “right,” focusing instead on shared experience.

8. Don’t Self-Select Out

Especially early in your career, don’t self-select out of opportunities by thinking you lack experience or aren’t “enough” for a role. Push yourself to apply and try new things, even if you feel unprepared.

9. Think Big, Ship Small

For product development, always “think big, ship small.” Envision the grand vision but break it down into the smallest possible, shippable increments to avoid getting too incremental or missing the bigger picture.

10. Assess Career Path

Evaluate your career path by asking three questions: Is your learning curve steep enough? Is your environment positively impacting your growth and ability to make an impact? Is the problem your product solves fun and interesting to you?

11. Prioritize Skills & Experiences

When planning your career, focus on acquiring desired skills and experiences rather than fixed roles or companies. This approach helps you make the most of your current career path and adapt to new opportunities.

12. Gain Customer Insight Quickly

When starting a new role, become best friends with a researcher and spend time directly watching customers use the product firsthand. This helps you quickly understand customer needs, problems, and product usage, preventing an “inside-out” perspective.

13. Communicate with Open Confidence

Convey confidence by being brave and courageous in small moments, showing up and speaking even before you’re fully ready, and being vulnerable. True confidence is also shown by asking questions, admitting “I don’t know,” and maintaining good body language (eye contact, presence in meetings).

14. Lead & Teach by Example

Lead and teach by example because repetition helps people remember and internalize lessons more effectively. Model the behaviors and meeting styles you want your team to adopt, creating the experience you hope they’re creating.

15. Avoid “All-Knowing Expert” Trap

New Product Managers should avoid the illusion of needing to be all-knowing and super confident, which leads to advocacy instead of inquiry. Instead, embrace curiosity and openness to collaboration, as trying to be the sole expert can hinder learning and feedback.

16. Focus on Work Outcomes

Instead of constantly seeking promotion, focus on being present in your job, having fun, and solving problems. Good outcomes will naturally lead to recognition and advocacy from others, making promotion a consequence rather than a direct pursuit.

17. Give Guidance, Not Micromanagement

As a manager, focus on giving guidance and direction that teaches repeatable patterns rather than precise, one-time instructions. This empowers your team and avoids micromanagement.

18. Police Your Own Input

In meetings, especially as a leader, police your own input by writing down what you want to say on post-its and waiting to see if someone else says it first. Only speak if your point is still valuable by the end of the meeting, as others may not challenge you directly.

19. Be Real, Even Optimistic

While optimism is good, be authentic and “real” with your team about challenges, incomplete plans, or areas of uncertainty. This builds trust and ensures everyone has a balanced perspective of the situation.

20. Know Your Chronotype

Understand your personal chronotype (e.g., morning person) and proactively block out time during your peak mental hours for deep work. This ensures you have dedicated headspace for your hardest tasks.

21. Rolling 12-Month Planning Cycle

Adopt a rolling 12-month planning cycle, revisiting and refining the plan every six months. This allows for higher confidence in the near term, better alignment with go-to-market, and quicker pivots based on new opportunities or progress.

22. Nested Product Strategy Metrics

Organize product strategy with a nested structure: R&D metrics, pillar metrics, area metrics, and then one or two key metrics at the team level. This provides clarity and accountability across different organizational altitudes.

23. Use Double Diamond Process

Implement the Double Diamond process (broaden, narrow, broaden, narrow) for product development. This systematic approach ensures rigorous customer selection, problem definition, and solution exploration, forcing teams to move beyond opinion-driven decisions.

24. Optimize Meetings & Approvals

To improve execution pace and quality, limit meeting attendance (e.g., no more than 10 people) and streamline approvals. Assign a single, clear approver for each piece of work and limit the number of formal reviews (e.g., no more than three).

25. Hybrid Office-Centric Work Model

Consider an office-centric hybrid work model (e.g., 3 days in office, 2 days remote) to leverage the benefits of in-person collaboration and impromptu strategy discussions, while retaining focused remote workdays. Actively encourage teams to re-engage with office practices like whiteboarding.

26. Staff Dedicated AI Prototyping

For exploring new technologies like LLMs, staff a dedicated team to prototype quickly and discover possibilities outside of typical development norms. This allows for rapid validation of hypotheses and identification of unexpected opportunities before full integration into product roadmaps.

27. Run Meetings with Asana

Use Asana to run all your meetings by assigning pre-reads with due dates using the multi-assign feature in subtasks. Take notes live in a task during the meeting, then highlight and convert action items into subtasks to ensure nothing is lost.