The Power of Why: Why Asking Questions is the Hallmark of Great Product Leaders

Amjad Shaikh
IncuBox
Published in
4 min readMar 19, 2024

In the fast-paced world of product development, decisive leadership is often seen as the key to success. But, what if the most valuable trait for a product leader isn’t the ability to give answers, but the relentless pursuit of asking questions?

Great product leaders are, at their core, deeply curious. They understand that the path to building products people love is paved with a constant stream of “whys” and “hows.” Here’s why asking questions is the superpower that sets them apart:

Photo by Sindy Süßengut on Unsplash

1. Unmasking Hidden Needs:

  • The Challenge: People often don’t know what they don’t know. Surface-level questions about features won’t unearth the gold beneath.
  • The Solution: Become a master interrogator! Instead of, “What features do you want?” ask, “Walk me through a typical workday. Where do you get stuck?” This approach uncovers hidden pain points users might not even realize exist.

2. Shattering Assumptions:

  • The Challenge: Our teams can get stuck in a rut of “how things have always been done.” This stifles creativity.
  • The Solution: Challenge those assumptions! Don’t accept user preferences or market trends at face value. Ask, “What evidence supports this?” or “Have we considered other viewpoints?” This critical thinking sparks innovation and opens doors to groundbreaking solutions.

3. Building Empathy: Walk a Mile in Their Shoes

  • The Challenge: Great products solve not just problems, but emotional needs too. If you can’t understand your users’ feelings, you’ll miss the mark.
  • The Solution: Go beyond features. Ask, “What emotions drive this behavior?” or “How can we design something that truly delights users?” By understanding their motivations, you can create products that connect on a deeper level.

4. Collaboration: Stronger Together

  • The Challenge: The best ideas often come from diverse perspectives. But if team members feel unheard, those ideas never surface.
  • The Solution: Become a facilitator, not a dictator. Ask, “What are your thoughts?” or “How can we leverage everyone’s expertise?” This fosters a collaborative spirit where everyone feels valued, leading to richer discussions and better decision-making.

5. Fostering a Culture of Continuous Learning:

  • The Challenge: The product landscape is ever-changing. Without a thirst for knowledge, your product risks becoming obsolete.
  • The Solution: Make asking questions a core value. Don’t see failures as setbacks, but as learning opportunities. Ask, “What can we take away from this?” or “How can we use these insights to improve?” This curiosity fuels innovation and keeps your team ahead of the curve.

By mastering the art of asking the right questions, you can become a product leader who uncovers hidden needs, fosters a vibrant team environment, and ultimately, builds products that users love.

Of course, asking questions isn’t just about quantity. It’s about the quality of your inquiries. Great product leaders ask questions that:

  • Dig Deeper: Don’t settle for surface-level answers. Imagine a user says, “The app is slow.” Instead of simply adding a “make it faster” ticket to the backlog, ask, “Can you walk me through a specific instance where the app felt slow? What were you trying to accomplish?” By probing further, you might uncover underlying issues like inefficient workflows or unclear navigation.
  • Challenge the Status Quo: Don’t be afraid to question long-held beliefs or assumptions. For example, your team might be convinced users need a complex feature. Ask, “Have we considered a simpler solution that achieves the same outcome? What evidence supports the need for this specific feature?” This can spark discussions that lead to more elegant and user-friendly solutions.
  • Spark Creativity: Use open-ended questions to encourage creative brainstorming and innovative solutions. Instead of asking, “What color scheme should we use for the new interface?”, try, “If we could completely redesign the user experience from scratch, what would it look like?” This kind of open-ended question allows your team to think outside the box and come up with truly groundbreaking ideas.

Here are some bonus tips for crafting powerful questions:

  • Start with “Why” and “How”: These words encourage people to explain their reasoning and thought processes, leading to richer insights.
  • Actively Listen: Pay close attention not just to the words, but also to the emotions and body language of the person you’re questioning.
  • Follow Up: Don’t be afraid to ask clarifying questions or dig deeper based on the initial response.

By incorporating these techniques, you can transform yourself into a master questioner, able to unlock hidden gems and propel your product to new heights.

Remember: There are no bad questions in the world of product development. By fostering a culture of curiosity and actively seeking answers, product leaders can create a space where the best ideas flourish, leading to products that truly resonate with their users. So, the next time you’re faced with a product decision, ditch the urge to jump to conclusions and get curious. Ask questions, explore possibilities, and watch your product soar.

Note: So much of this article is inspired by me reading “Great leaders ask great questions: Here are 3 steps to up your questioning game.” Please do read it. It is a fascinating article about why questioning is a critical leadership skill and Questioning isn’t just a way to get the right answer — it’s also a means for sustaining relationships and creative thinking.

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Amjad Shaikh
IncuBox
Editor for

Crafting stories, shaping experiences, and engineering innovation – all while embracing the art of continuous learning and changing.