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Product leadership often requires navigating rooms filled with stakeholders who have decades more experience than you do. Whether communicating with engineering leads, designers, or C-suite executives, the pressure to prove one's value can lead to defensiveness or "imposter syndrome." However, the most effective leaders do not rely on tenure or technical dominance to win arguments. Instead, they rely on a deep, empirical understanding of the customer.
Paige Costello, Product Lead at Asana, has spent her career leading teams at major tech companies like Intercom and Intuit, frequently finding herself as the youngest person in the room. Through these experiences, she has developed frameworks for garnering trust, evolving product strategies at scale, and coaching the next generation of product managers.
Key Takeaways
- Bring the insight, not just the opinion: You can win over experienced skeptics by becoming the foremost expert on customer behavior and market data.
- Adopt a rolling planning cadence: Asana moved from strict annual planning to a six-month cycle with a rolling 12-month view to balance predictability with agility.
- Utilize the "Exposure" lever for growth: Career growth isn't just about education and experience; it requires "exposure"—being in the room to observe how decisions are made.
- Challenge scarcity mindsets: When faced with difficult trade-offs, asking "how might the opposite be true?" can unlock creative solutions that accommodate conflicting needs.
- Formalize feedback with SBI: Use the Situation-Behavior-Impact framework to deliver difficult feedback objectively, reducing defensiveness.
Winning Trust Without Tenure
One of the most daunting challenges for rising product leaders is influencing stakeholders who possess significantly more functional expertise or tenure. Attempting to out-engineer an engineer or out-design a designer is rarely a winning strategy. Instead, the most reliable path to credibility is "bringing the insight."
The Power of Customer Expertise
If you can speak with authority on how customers actually use the product, you shift the conversation from opinion to evidence. This does not require decades of experience; it requires the discipline to sit with researchers, watch customer sessions, and analyze the data.
The thing I would say is bring the Insight. Know Thy customer, Know Thy Market, know [thy] competitors, know [thy] numbers, know [thy] product. If you can be the person in the room who has watched customers use the product... and you can do that with confidence and Clarity... you can bring Insight that makes people curious and trust you.
By effectively becoming the voice of the market, you provide value that functional experts may lack. This creates a "trust equation" defined by credibility, reliability, and authenticity, divided by the perception of self-interest. When stakeholders see that your insights are grounded in customer reality rather than personal ego, trust follows naturally.
Confidence Through Curiosity
Paradoxically, projecting confidence often involves admitting what you do not know. Leaders who armor themselves with feigned certainty are less trusted than those who are vulnerable enough to ask questions. Real confidence is displayed by body language, direct eye contact, and the courage to ask for clarification when a concept is unclear.
Evolving Product Strategy at Scale
As companies scale, their product development processes must evolve to prevent stagnation. At Asana, this meant shifting the altitude and horizon of their planning efforts. Originally organized around projects and locations, the product organization restructured into "Areas" and "Pillars."
The Rolling Planning Model
Static annual plans often fail because they cannot account for the rapid pace of technological change. Asana shifted from a strict annual plan to a six-month planning cycle that maintains a rolling 12-month view. This hybrid approach provides the business with enough confidence to align go-to-market strategies while retaining the flexibility to pivot based on new data or technologies, such as the recent explosion in Large Language Models (LLMs).
The Double Diamond Process
To ensure rigorous thinking, Asana utilizes the "Double Diamond" design process. This involves two phases of diverging and converging:
- Problem Space: Go broad to identify the right customer and problem, then narrow down to a specific target.
- Solution Space: Go broad on potential solutions, then narrow down to the specific execution path.
This structure prevents teams from jumping straight to solutions based on intuition. However, processes must serve the goal, not the other way around. With the advent of generative AI, Asana’s teams recognized that the standard Double Diamond process might be too slow. They authorized teams to skip straight to prototyping, allowing them to validate the capabilities of LLMs rapidly before committing to full-scale development.
Coaching and Conscious Leadership
Effective management goes beyond assigning tasks; it requires modeling the behaviors you want to see. This is often described as the "Three E's" of career growth: Education, Experience, and Exposure. While most early-career professionals focus on education (reading books) and experience (doing the job), they often underestimate exposure—the value of simply being present where high-level work happens.
The "Above the Line" Mindset
A critical component of Asana’s culture is the concept of "Conscious Leadership," specifically identifying whether one is "above the line" or "below the line."
- Above the Line: Open, curious, and committed to learning. Playful and creative.
- Below the Line: Committed to being right, winning, and defensiveness. Black and white thinking.
Recognizing when you or your teammates have drifted "below the line" allows for a reset. It creates a shared vocabulary that makes conflict resolution less personal and more productive.
Escaping the Scarcity Trap
When leaders feel overwhelmed by conflicting priorities, they often default to a scarcity mindset—believing they must choose between two negative options. A powerful tool to break this cycle is the question: "How might the opposite be true?"
The moment I challenge myself and said how might the opposite be true my shoulders dropped I feel more relaxed I was like oh yeah I can do both it'll be fine.
This simple prompt forces the brain to stop looking for reasons why something can't work and start looking for creative ways it could work. It moves the mental state from anxiety to problem-solving.
Common Pitfalls for Product Managers
Even talented product managers can stall their careers if they misunderstand the role's core demands. The most common error is the "illusion of the all-knowing PM."
Advocacy vs. Inquiry
Junior PMs often believe they need to be the smartest person in the room. This leads to "dark room" development, where a PM works in isolation to perfect a spec, only to reveal it with a rigid defense. This approach alienates the team and misses critical feedback.
Success comes from "performative collaboration" transitioning into genuine inquiry. When a PM shares work early (e.g., "This is 70% complete, and here is the 30% I am unsure about"), they invite the team to co-create the solution. This builds buy-in and results in a more robust final product.
The SBI Feedback Loop
When things go wrong, managers must give feedback that is actionable rather than accusatory. The Situation-Behavior-Impact (SBI) model is essential for this:
- Situation: "In Tuesday’s marketing meeting..."
- Behavior: "...you interrupted the presenter three times..."
- Impact: "...which caused the team to withdraw and stopped us from hearing their full proposal."
By focusing on the subjective impact ("it made me feel" or "it caused X") rather than objective truth ("you were rude"), the conversation becomes about resolving the outcome rather than debating the intent.
Conclusion
Building a successful career in product leadership is rarely about having all the answers. It is about asking better questions, gathering better data, and creating an environment where the team can operate "above the line."
Whether it is adopting a rolling planning process to stay agile, or using mental models to reduce anxiety, the goal remains the same: clarity. As Paige Costello notes, assessing your career health comes down to three factors: the steepness of your learning curve, the supportiveness of your environment, and the genuine interest you have in the problem you are solving. If those three align, the titles and accolades will follow.
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