Beyond the Five Whys: The Power of Smart Questioning for Product Leaders
Ditch the 'why' and embrace 'what' and 'how' to boost team creativity and navigate ambiguity in the age of artificial intelligence and beyond
Throughout my career, I’ve encountered many smart people with a fixed mindset. They saw no reason to adjust their response to a different perspective or new information. What they knew or thought was ‘right’ was it - end of story.
I recall a CEO I reported to asking why a bug hadn’t been caught earlier in development. I appreciated their frustration. I also knew the individual didn’t want to hear the truth - we did thorough testing, but an edge case had been missed. Yes, it was an issue we’d learn from. In the CEO’s mind, there was zero reason for error. Despite working in technology, he associated a ‘bug’ with ‘being wrong’ - and that was not tolerated.
Where does your workplace fall on the following statements?
Leaders seek input from those who consistently validate their views or have similar backgrounds and styles.
Leaders demand answers NOW, viewing immediate responses as the only sign of intelligence and perceiving the fastest voices to be “right.”
With the rise of AI, growth-minded organizations are shifting from valuing those who simply 'know it all' to those who can 'learn it all'. Microsoft’s CEO Satya Nadella is the reference which often comes to mind. His focus on favoring a growth mindset is noted as one of the factors leading to the company’s continued growth.
With anyone being able to access a wealth of information through AI tools, knowing all the answers is no longer a badge of superiority. For example, in product management interviews, recruiters are calling out candidates who are obviously typing into a chatbot before responding.
Instead, how you gather, use, and apply the information distinguishes strong product managers and leaders. Welcome to the AI era, where the differentiator is how you ask a question. We’ll explore each of the following topics.
A "learn-it-all" mindset focused on continuous learning and adaptation is more valuable than a "know-it-all" mindset relying on existing knowledge.
Shifting from "why" questions to "what" and "how" questions promotes deeper thinking, innovation, and inclusivity in team discussions.
Developmental leadership helps organizations navigate complex challenges and drive positive change in uncertain environments.
Limitations of the Five Whys
I began my product management career as a user experience researcher at Salesforce. I frequently used the Five Whys technique, asking “why” five times to get to the root of the response.
[Researcher] Why did you decide not to renew your subscription?
[Customer] We found the reporting functionality to be inaccurate.
[Researcher] Why do you think the report results are inaccurate?
[Customer] The layout isn't intuitive, and the page loads slowly.
[Researcher] Why do you think the layout and loading speed are causing the report results to be questioned?
[Customer] The slow loading and unclear layout create a lack of trust in the information. As a result, Sales contacts me directly for data.
[Researcher] Why do you think they see calling you as a more reliable option?
[Customer] They expect an immediate response.
[Researcher] Why does Sales prefer an immediate response from you over the online reporting capabilities?
[Customer] They find the reporting page confusing and can't easily find the reports they need.
[Researcher] The core issue seems to be the confusing interface and slow performance, leading to a lack of trust in the reporting capabilities.
Mystery solved. The interface and load times, not inaccurate results, caused data distrust and attrition. All wonderful in a simple scenario, yet the Five Whys technique is no longer sufficient for today’s complex product environments where every customer and interaction can result in a different response and experience.
Similarly, when one has access to unlimited “factual” information, asking why in a stakeholder meeting won’t win you any friends. When asked ‘why’ in a work setting, people often get defensive. They feel they must have the perfect answer immediately. Instead, asking “what” and “how” - inquisitive questions - dig deeper, bringing non-obvious information to the surface quickly.
Dealing with feelings and relating to one another is not a distraction from our work — it is part of our work, because we are all human beings (for now!).
For example, let’s try these questions and the reframed versions on for size.
[Original] Why pursue that option?
[Reframe] What is your perspective?
[Reframe] What are other ways to approach the situation?
[Original] Why did you reach that conclusion?
[Reframe] Have you faced this situation before? What did you do that worked?
[Reframe] What could you change for better results?
Even though Five Whys will remain a useful resource for customer research, asking questions in a manner that reflects empathy, listening, and fostering growth will differentiate strong leaders for employees facing constant change and complexity, wondering when AI will replace them.
Developing a Balanced Question Mix
How and What questions help not only with growth mindset oriented employees, they can also help with the tricky fixed mindset ones too - maybe even your fixed mindset CEOs.
We’ve all had challenging days and likely been a difficult employee at some point. I had a very organized employee who showed up for brainstorming meetings with extensive, multi-step FigJam templates. His colleagues found his approach too controlling and fixed - not the environment associated with ideation. Whenever they raised concerns, he declared them difficult and complained to me.
A common coaching practice is to ask clients how they’d like or expect to be treated in the same situation. Following this guidance, I avoided “why” questions. Instead, I led with curiosity to explore my employee’s motivation. Here are the steps I took.
Provide examples. I asked him to describe the last meeting and how he felt it went. I shared his colleagues’ different perspective. Using a recent example brought images of the meeting to mind.
Acknowledge the problem. He thought he was being helpful by providing a detailed structure. I proposed an alternative view that his colleagues found his approach off-putting.
Listen actively. Instead of judging, I asked open-ended, inquisitive questions. By listening with empathy instead of immediately telling him what to do, I created a safe space for expansive thinking.
Explain the impact. The detailed structure he provided reflected his thinking process. He liked to see all options in one place to evaluate and decide on the path forward. We discussed how his approach limited his colleagues to one - his.
Agree on next steps. With a better understanding of his colleagues’ perspectives, we agreed on two immediate actions: he would provide more context to clarify his thought process and invite others to lead brainstorming sessions to learn from their approach.
He realized he’d likely receive constrained thinking in return when he visualized himself as the recipient of strict work requirements. But if he gave people the benefit of the doubt, he’d likely receive more open and exploratory thinking.
Although displaying forcefulness was high on the list of most-sought-after communication traits in 2012, it’s less desired today. People now gravitate more toward leaders who listen and learn from others before they make decisions—a trait seen as critical to growing markets and retaining top talent.
I circled back with the employee and his colleagues. The next session was more open and raised new ideas. Even though the difficult employee had a couple of stops and starts during the session, his willingness to explore alternative approaches impressed his colleagues. Through the exercise, he started to appreciate true team collaboration.
Rise of Developmental Leadership
Developmental leadership emphasizes creating conditions for all employees to grow daily. It establishes a mindset of “What could I change — or what could we change — to improve the way we are working?”
Developmental leaders drive change by prioritizing human skills, not just technical abilities. In today’s environment where AI is quickly making advances in technical domains, the importance of deepening our capacity for what is uniquely human is greater than ever.
To put it another way, leaders are no longer solving linear technical problems. Instead, we are working with complex adaptive systems and adaptive challenges that don’t have obvious answers. Navigating to solutions requires engagement and collaboration from all parts and levels of the organization, not just senior leaders.
Product leaders navigate complex technology, market dynamics, and user needs. The shift from a "know-it-all" to a "learn-it-all" mindset is essential for organizational and individual success. Creating an environment that values learning over repetition and encourages smart questioning over providing answers enables organizations to adapt in uncertain times.
What the Future Holds for Product Leaders
The future of product leadership isn't about asking 'why' or immediately providing the 'right' answer. Instead, it's in asking open-ended, developmental questions that invite every employee to seek ways to improve the ways of working together.
Shift from "know-it-all" to "learn-it-all" mindset: Transitioning from a fixed mindset valuing historic knowledge to a growth mindset prioritizing continuous learning and adaptation is crucial in the AI age, where access to information is readily available, and the ability to learn and apply knowledge is more valuable than simply possessing it.
Importance of asking effective questions: Moving away from "why" questions, which can make people defensive, and focusing on "what" and "how" questions encourages deeper thinking, fosters innovation, and creates a more inclusive environment for team members to contribute ideas.
Developmental leadership creates growth conditions. In today's complex business environment, leaders face challenges without obvious answers. By prioritizing human skills, encouraging collaboration across all organizational levels, and valuing learning over immediate answers, organizations can navigate uncertainty and drive positive change.
“If you want people to listen to you, listen to them. The best way to achieve success is to deserve success. Small changes in your actions change your entire world.” - Shane Parrish
Implementing these strategies can help you foster a more innovative and adaptable team, ready to tackle any challenge.
