The art of asking better questions
And why it will change the way you do product!
In my time in product, I’ve noticed a common denominator in the most successful product managers that I’ve worked with. These people aren’t necessarily the smartest in the room nor do they have the most years of experience. What differentiates them from the rest is that they’ve mastered an important, underrated skill.
The art of asking questions
You might wonder, what’s so hard about asking questions? It’s easy, right? Everyone does it. The average adult asks about 25-30 questions a day.
But it’s not about asking questions, it’s about asking the right questions. The kind that digs deeper, gets customers to open up and uncovers their real problems.
This is a skill that takes time and practice, and what separates a feature factory from an outcome-driven product leader.
Let’s dive into a few ways to get you started.
Be curious
It’s as simple as that. Be curious about the world; the way things work and the reasons they are the way they are. As a child, I remember questioning everything (like, everything). In fact, preschoolers ask up to 400 questions a day.
Why does this number drastically drop as we get older? We stop being curious. We assume we should already know the answer and worry people will think less of us if we don’t. When is the last time you said “I don’t know” at work?
Curiosity is not a personality trait, it’s a practice. It’s a muscle you can strengthen by intentionally practicing it in your daily life.
As product managers, our jobs are centred around solving problems and figuring out what to build. But we aren’t expected to know the exact solution or answer, that’s why product roles exist!
So be curious, you’re never going to know everything, the only way to learn is to be open and start asking more questions.
Listen to understand, not to respond
Actively listen. When having a conversation, it’s very easy to start thinking about what you are going to say next rather than really listening to what the other person is saying.
We are so efficient with language that we forget to actually be effective with it. Active listening means to understand what the person is saying, reflect, then responding to what they have just said.
When interviewing customers, you might have prepared a script or a bank of questions to go through which can be a great starting point, but it’s important to be flexible.
If you actively listen, you will start to feel more engaged and notice small details you didn’t notice before. It may even prompt you to ask different questions than you originally planned.
The greatest product managers put themselves in their customers’ shoes and show genuine empathy. If you aren’t present in the conversation, you can completely close the door to key details that matter the most.
The customer conversations I’ve gotten the most value out of are when I have asked my customer an open question, put my pen down and actually listened, instead of formulating my next response in my head. Customers want to share their experiences, but you need to create a space where they trust you and feel comfortable enough to share their frustrations.
Ask open ended questions
Yes or no questions quickly shut down a conversation. I’ve seen people ask a question and then immediately answer it themselves (and yes, I’ve been guilty of this too).
Keep it open. Ask a clear question, pause and let the person think. The pause not only allows the other person to digest your question and formulate their response but also shows you are trying to understand them. Remember, customers can’t always clearly articulate their problems, which is why they often skip straight to surface-level solutions.
A great example: I once had multiple enterprise customers consistently requesting a feature that would completely change the purpose and architecture of the product. The feedback was persistent, so I arranged calls with several customers. Rather than discussing the feature request itself, I asked what outcome they were trying to achieve.
The answer surprised me: what they actually needed was something completely different. The feature they were requesting wouldn’t have solved the underlying problem.
The conversation changed our direction entirely. Once we understood the underlying problem, we were able to build a feature that customers genuinely needed rather than the solution they initially requested.
One of my favourite techniques is one I learnt from Dr Alison Wood Brooks, a Harvard Business School professor, is called “never ending follow-up questions”. It’s exactly what it sounds like. You ask a follow-up question every time they respond. It shows that you are genuinely interested in what the other person is saying. It can feel unnatural at first, but it drives deeper connections.
For example,
PM: Can you walk me through the last time this problem came up for you?
User: I was trying to generate a report
PM: What were you trying to show in the report?
User: The team’s weekly sales metrics.
PM: Who else needs to see that report?
User: My manager and two other sales leads.
PM: How often does your manager ask for this kind of report?
User: Every Monday morning.
PM: What happens if the report isn’t ready by Monday?
User: Our weekly sales meeting gets delayed.
And it keeps going:
How long does the meeting get delayed by?
What do you do while you wait for the data to load?
Have you tried any other workarounds?
How long does that take?
The right question is better than the right answer
Asking the right questions often uncovers bias and preconceived assumptions you didn’t even know you had.
When building products, it’s easy to unintentionally start solutioning based on what you think users need. This is where great products go wrong. You end up building for a problem you don’t understand.
The best way to uncover the real problems is to ask the right questions.
When you admit you do not know the answer, you invite others to work together to come up with a solution.
The best features I have shipped were designed in partnership with design, engineering, customers, marketing, sales and customer success teams.
Don’t know what to ask?
I’ve been in situations where the most senior person present asked a simple question “Why are we working on this?” and nobody was able to answer them. That one question opened the conversation and created space for others to challenge assumptions and explore new perspectives.
If you’re stuck, the 5 Whys method is a great one that I keep coming back to. It’s easy to remember and extremely effective, allowing you to challenge the status quo.
Give it a try
The next time you’re having a conversation, whether it be with a customer, a colleague or a friend, try out one of these techniques and notice what changes about your conversations.
What’s the best question someone has asked you? Drop it in the comments below.