How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana)
Executive Summary
Paige Costello discusses problem-focused planning, exploring before narrowing, meaningful success measures, customer insight and open communication. Selected third-party transcript coverage excludes sponsor reads, personal wellbeing, AI passages and current workplace-policy claims. Asana examples are her historical accounts, unverified here. Untimed editorial topics are not video chapters.
Key Takeaways
Organize around a durable problem
Costello describes moving beyond projects and locations toward areas with a target customer and problem space. The structure connects strategy and measures at different levels. A roadmap becomes more useful when it explains the problem being addressed rather than only naming features.
Revisit plans with different confidence levels
She describes planning for a nearer period with more confidence and a later period with less. Revisiting the plan makes room for changed opportunities and new information. The example is her account of Asana's approach, not a claim that every team needs the same cycle.
Go broad before narrowing a choice
Her Double Diamond description explores customers, problems and solutions before selecting among them. The steps push a team beyond its first opinion. Reviews and artifacts are matched to the ambiguity already resolved rather than forcing every project through identical research.
Define solved problems rather than feature use
Costello warns that choosing feature usage as the success measure can become teaching to the test. The team needs to know who it serves and what it means for their problem to be solved. Usage is not automatically the intended customer outcome.
Bring insight instead of pretending experience
She recommends knowing the customer, market, numbers and product well enough to contribute a useful perspective. A younger or newer leader does not need to imitate another person's expertise. Asking strong questions and sharing grounded insight can make the conversation more useful.
Watch customers firsthand
Costello suggests working closely with research and seeing actual product use. Heavy internal use can make a team assume it behaves like its customers. Firsthand observation helps reveal where that assumption is wrong and where the organization serves people poorly.
Show confidence through openness
She describes asking for clarification and checking what was missed rather than asserting an answer constantly. Being present in the meeting also helps notice unanswered questions. Openness supports a more accurate discussion, not merely a more forceful performance.
The Conversation Breakdown
Organize around a durable problem
⏱ Untimed topicCostello describes moving beyond projects and locations toward areas with a target customer and problem space. The structure connects strategy and measures at different levels. A roadmap becomes more useful when it explains the problem being addressed rather than only naming features.
Revisit plans with different confidence levels
⏱ Untimed topicShe describes planning for a nearer period with more confidence and a later period with less. Revisiting the plan makes room for changed opportunities and new information. The example is her account of Asana's approach, not a claim that every team needs the same cycle.
Go broad before narrowing a choice
⏱ Untimed topicHer Double Diamond description explores customers, problems and solutions before selecting among them. The steps push a team beyond its first opinion. Reviews and artifacts are matched to the ambiguity already resolved rather than forcing every project through identical research.
Define solved problems rather than feature use
⏱ Untimed topicCostello warns that choosing feature usage as the success measure can become teaching to the test. The team needs to know who it serves and what it means for their problem to be solved. Usage is not automatically the intended customer outcome.
Bring insight instead of pretending experience
⏱ Untimed topicShe recommends knowing the customer, market, numbers and product well enough to contribute a useful perspective. A younger or newer leader does not need to imitate another person's expertise. Asking strong questions and sharing grounded insight can make the conversation more useful.
Watch customers firsthand
⏱ Untimed topicCostello suggests working closely with research and seeing actual product use. Heavy internal use can make a team assume it behaves like its customers. Firsthand observation helps reveal where that assumption is wrong and where the organization serves people poorly.
Show confidence through openness
⏱ Untimed topicShe describes asking for clarification and checking what was missed rather than asserting an answer constantly. Being present in the meeting also helps notice unanswered questions. Openness supports a more accurate discussion, not merely a more forceful performance.
Core Frameworks & Ideas
Explore then narrow
Consider customer, problem and solution alternatives before settling on the next build.
Problem-based success
Define the customer outcome instead of treating feature use as sufficient.
Insight-based credibility
Observe customers and bring a grounded perspective while remaining open about what you do not know.
Actionable Next Steps
- ✓Name the target customer and durable problem behind a roadmap item.
- ✓Define what solved means before picking a feature metric.
- ✓Observe a customer using the product firsthand.
- ✓Ask at the end of a discussion what was missed or needs clarification.
Notable Quotes
“So I really push people not to self-select, and I try to remind myself where that's appropriate to do the same thing.”
“It's really important because then you also know what success looks like because if you pick your success metrics as using a feature, that's it.”
“So thinking about the learning curve, thinking about whether the environment is positively impacting your ability to grow your career and make an impact.”
The One Thing to Remember
Know the customer problem and what solved means before choosing features and measuring their use.