The Power of Asking Questions

There is a quiet superpower many overlook in product leadership—not charisma, not vision decks, not sweeping strategies. Just questions. Good ones.

The kind that make people pause.
That open blind spots.
That make teams feel seen, not judged.

In a world that rewards fast answers and confident opinions, the ability to ask thoughtful, honest questions is often what sets the best leaders apart. Not the loudest in the room, but the most curious. Especially in the moments no one else is paying attention.

A Tale of Two Onboardings

You can often tell whether someone will thrive in a product leadership role within their first few weeks—not by what they say, but by what they ask.

Years ago, I got a new manager. In our early meetings, they asked what felt like an endless stream of basic questions—
"What do you do exactly?"
"What is this initiative about?"
"Which KPIs are we tracking?"
"What does each team member own?"
Then they asked how to use our internal tools.

At first, I was confused. These seemed like things a senior person should already know. Why were they hired if I needed to explain all the basics? But then I noticed something. Their questions weren't careless—they were deliberate. They weren’t pretending to know. They were trying to truly understand.

Soon, the questions evolved from “what” and “how” to “why.”
“Why did we prioritize this initiative over another?”
“Why is this feature built this way?”
“Why is this our scope?”

And suddenly, I was challenged. Not defensively, but constructively. I felt like someone finally understood the depth of our work—and wanted to make it better. That manager earned respect by doing something deceptively simple: asking questions that made us think sharper, act bolder, and deliver stronger.

Now contrast that with another experience. I was asked to onboard a product leader with impressive credentials. I was genuinely excited—until our first meeting. They opened with a long monologue about their past roles, notable companies, and opinions on the industry. It felt rehearsed.

When I gave a quick overview of what my team does, I expected curiosity. Questions. Engagement.
Instead? Silence.
No “What are your biggest challenges?”
No “Where do you need support?”
No “What are your expectations of me?”

It was underwhelming. I wrapped the meeting by offering help:
“If you have any questions, I’d be happy to explain more.”
Their reply? “Let’s do monthly 1:1s.”

Those became a 30-minute black hole each month—filled with generic talk about processes and previous jobs, none of it relevant to my reality.

So, what happened next?
Manager #1 thrived. They grew. The team flourished under their leadership.
Manager #2 quietly left after a while. I suspect they couldn’t hold their ground in high-stakes conversations. Not because they lacked knowledge—but because they never took the time to truly understand the products, the users, or the problems.

Their contributions remained surface-level. They spoke in frameworks and best practices—but couldn’t connect those to the messiness of real product work.

Why Questions Matter

The strongest people I have worked with rarely lead with statements.
They lead with questions like:

• “What is the biggest risk no one is talking about?”

• “What is the real problem we are solving here?”

• “If this goes well, what changes for the user?”

• “What would we build if we started from scratch?”

These questions aren’t flashy. But they cut through noise. They create clarity. And they build trust.

What strong leaders do:

• Ask before advising.

• Listen before responding.

• Challenge assumptions, not people.

• Use curiosity to unlock impact—not to perform intelligence.
  

When Asking Questions Is Crucial

Let’s explore where asking the right questions makes the biggest difference:

1. Onboarding into a new team

We have all seen it: a new joiner walks in and starts offering “solutions” before understanding the problem. It is frustrating.
Strong leaders don’t rush to change things—they slow down to ask questions like:
✅ “What is the biggest challenge your team is facing?”
✅ “What would you improve if you had no constraints?”
❌ “Why are you still doing it this way?”

Respect is earned through curiosity. Listening builds credibility faster than expertise.

2. Working with cross-functional teams

Many PMs shy away from technical discussions, thinking it is “not their domain.” But the best ones lean in—with humility.
✅ “What is the biggest tech constraint we need to factor in?”
✅ “How does this API impact downstream flows?”
❌ “Can we just do it like in my last company?”

Asking thoughtful, non-judgmental questions shows engineers you respect their craft—and want to understand it, not override it.

3. Review sessions (design, sprint, product)

Saying “I don’t like it” is rarely helpful.
Instead of offering vague opinions, good product folks ask user-centered questions:
✅ “How does this help a first-time user complete the task faster?”
✅ “What is the one thing we want users to notice here?”
❌ “Can we make the button red instead?”

Good questions spark reflection, not defensiveness.

4. Strategy discussions

Even in the most senior conversations, questions matter.
✅ “What assumptions are we making here?”
✅ “How are we measuring long-term success?”
❌ “Is this aligned with the strategy deck?”
The goal isn’t to sound smart. It’s to think clearly, together.

Questions That Miss the Moment

It is not always about asking “bad” questions—but about asking the wrong ones at the wrong time.

Context 1: Team shares a new initiative

❌ “When will it be done?”
✅ “What problem are we solving—and how will we measure success?”

Delivery dates matter. But if that is your only question, it signals you care more about deadlines than impact.

Context 2: Team escalates a dependency

❌ “Can you align better with the other team?”
✅ “What is blocking progress—and what is the risk if it is delayed?”
✅ “Which initiatives are we deprioritizing if we say yes to this?”

Process talk won’t unblock them. Deep understanding might.

Context 3: Giving feedback

❌ “I would have done it differently.”
✅ “What were the trade-offs you considered when deciding this path?”

Judgment shuts down conversation. Curiosity keeps it open.

How Not to Ask Questions

Not all questions are created equal.
Even with good intentions, some ways of asking can lead to confusion—or worse, derail the conversation entirely.

Here are a few patterns I have observed that can weaken the power of a question:

1. Asking... then immediately answering yourself

Some people ask a question and jump straight into their own opinion—leaving the other person unsure whether a real answer is expected.

❌ “Why didn’t we prioritize this feature? I mean, I assume it is because the tech team didn’t have capacity, and anyway it probably wouldn’t have moved the needle that much…”
✅ “Why didn’t we prioritize this feature—and what were the trade-offs we considered at the time?”

If you’re genuinely asking, ask. Then pause. Give space for the answer. Let curiosity win over performance.

2. Combining multiple questions into one long sentence

This usually overwhelms the other person—and makes it unclear what to answer first.

❌ “So what was the user insight behind this change and how did you come up with the solution and what would you have done differently if you had more time?”
✅ “I have a few questions—can I ask them one by one?”
✅ “First, what was the key user insight behind this change?”

Shorter questions are more challenging to answer—not because they are difficult, but because they require clarity of thought. And that is a good thing.

3. Being vague or abstract

Vague questions lead to vague answers. If you are not clear in what you are asking, the other person is left guessing.

❌ “What’s the situation with that thing from last week?”
✅ “What’s the current status of the backend fix we discussed in last week’s bug triage?”

The more precise your question, the easier it is for others to respond meaningfully.

The takeaway:

🟢 Be clear. Be concise. Be intentional.
A well-crafted question is a sign of respect—it shows that you value the other person’s time, thinking, and perspective.
And that clarity often invites a deeper, more useful answer.

In Closing

The next time you're in a meeting, try holding back your opinion for just a moment longer.
Instead, ask:
“What am I missing?”
You will be surprised how much you learn—and how much faster you build trust.

Strong product leaders don’t have all the answers. But they ask the kind of questions that bring better answers to the surface. And that’s what makes all the difference.