The Key to Asking Great Questions
Hint: It’s not just about what you ask, but how you ask it.
Don’t hesitate to ask questions!
It’s a piece of advice repeated so often that it’s practically a workplace mantra.
And yet, most of us don’t ask enough questions. Instead, we hold back, make assumptions, fill in the blanks ourselves, and move forward with incomplete information. The result? Misunderstandings, miscommunications, and mistakes that could have been avoided with a simple, well-placed question.
The idea for this article came from a recent conversation with one of my 1-1 coaching clients that went something like this:
Client: “I don’t know why my manager suddenly asked about this. He seemed stressed and a bit micromanage-y.”
Me: “Did you ask him?”
Client: “Not really. I didn’t want it to seem like I was questioning his authority.”
My client’s response brought up a common misconception: that asking questions can be seen as a challenge rather than a tool for clarity and collaboration. He assumed his manager was unhappy with him and hesitated to ask for fear of making things worse. I encouraged him to go ask and coached him on how to frame his question to get the clarity he needed.
In our next session, he came back relieved. It turned out there had been a simple miscommunication. His manager wasn’t upset—he was reacting to incomplete information. The fact that my client asked the question helped clear up the misunderstanding and improved their working relationship.
This conversation made me realize how often we hold back from asking questions, why that’s the case, and what to do about it, so in this article, we’ll cover:
Why we don’t ask enough questions
How to avoid seeming insecure when asking questions
How to ask questions without coming across as confrontational
How to frame questions from a place of curiosity
Let’s dive in.
So why don’t we ask more questions?
One big reason is that asking questions can feel risky. People often hesitate because:
Questions can reveal insecurities – Asking too many or overly cautious questions can make someone seem unsure of themselves, especially in professional settings.
Questions can feel aggressive – If phrased bluntly or repeatedly, they might come across as challenges rather than genuine curiosity.
These concerns often lead people to stay silent, assuming they should already know the answer or fearing they’ll make someone uncomfortable. But avoiding questions doesn’t lead to clarity—it leads to misalignment, frustration, and preventable mistakes.
That’s why it’s important to understand when asking questions feels like insecurity and when it feels like an attack—and how to ask them in a way that builds trust rather than tension.
When asking questions feels like insecurity
Asking questions shows you're interested in learning. But if you ask too many questions or sound unsure of yourself, people might think you lack confidence. You don’t want questions to make others question you. Here's what to watch out for:
Constantly seeking reassurance instead of clarity – If your questions sound like you’re looking for validation rather than understanding, it can make you seem unsure of yourself.
🚫 “Is this the right way to do it?” (Sounds like self-doubt)
✅ “Can you confirm if this aligns with what we discussed?” (Shows initiative and checks alignment)
Over-explaining before asking – Long-winded lead-ups to a question can make it seem like you’re hesitant or trying to justify asking.
🚫 “So, I was thinking about this and wasn’t sure if it made sense, but I wanted to check because I don’t want to mess it up…” (Feels unsure)
✅ “Can you clarify how this part should work?” (Direct and confident)
Asking the same question multiple times – You can ask a question more than once, but be mindful of how frequently. Repeatedly checking the same thing can make it seem like you lack confidence in the answer you already received.
🚫 “Wait, so just to confirm one more time, we are going with option A?”
✅ “Got it—we’re moving forward with option A.” (Confidence through affirmation)
Excessive apologizing – Prefacing a question with an apology can make it seem like you’re unsure whether you should be asking at all. Similar to the previous point, apologizing before asking questions is negative only if done in excess. You can sound polite without needing to apologize.
🚫 “Sorry if this is a dumb question, but…”
✅ “I want to make sure I understand this correctly…” (Owns the question without apology)
When asking questions feels like an attack
How you ask questions matters a lot. A question can either lead to a good conversation or make people uncomfortable. Even when you mean well, some ways of asking questions can make people feel like they're being attacked or judged instead of being invited to share their thoughts. Here are some common mistakes to avoid:
Implying doubt – Questions that sound like skepticism rather than curiosity can make the other person feel like they need to defend themselves.
🚫 “Are you sure that’s the right approach?” (Suggests lack of confidence in their decision)
✅ “What made you choose that approach?” (Shows interest in their reasoning)
Asking “why” – “Why” questions often come across as confrontational, especially if they’re directed at someone’s decision-making. They can make the person feel like they’re being challenged rather than invited to explain. You can find out the “why” behind something by asking “how” or “what” questions.
🚫 “Why did you do it like this?” (Feels like an accusation)
✅ “How did we decide on this approach?” (Encourages discussion)
Badgering the witness – Asking the same question repeatedly, pressing for a specific answer, or layering multiple questions at once can feel like an interrogation. If someone isn’t responding the way you expect, consider whether your approach is putting them on the defensive.
🚫 “But why? That doesn’t make sense. Are you sure?” (Feels aggressive and exhausting)
✅ “I see it differently—can you help me understand how you got there?” (Encourages open dialogue)
Finding someone to blame - Questions that assign fault rather than seek understanding can make others defensive.
🚫 “Who approved this?” (Feels accusatory)
✅ “How was this decision made?” (Encourages discussion)
Not engaging with the answers provided – If you ask a question but don’t acknowledge the response—or dismiss it outright—it signals that you weren’t really looking for an answer. Instead of fostering conversation, this can make the other person feel unheard or unappreciated.
🚫 “That’s not important.” (Shuts down conversation)
✅ “That’s an interesting perspective—can you elaborate?” (Shows respect and invites further discussion)
Questions that feel like attacks make people go into defense mode, killing your shot at an open and productive conversation. Ultimately, the goal of questions is an honest and thoughtful dialogue. So how can we reach this goal? By using curiosity.
Curiosity, the magic ingredient of great questions
Being curious means being open to learning new things and understanding others better. When you ask questions with real curiosity, you show that you want to learn, not judge or criticize.
Questions are a great way to show curiosity. But the way you ask them matters a lot.
Next, we’ll discuss ways to ask questions that make people want to open up.
How to frame questions from a place of curiosity
If you want to ask questions without sounding skeptical or confrontational, try these techniques:
Invite people to explain their thought process – Instead of making someone feel like they have to defend a choice, invite them to explain it.
“What led you to take a different approach this time?”
“What inspired this decision?”
Express curiosity and desire to understand – Your interest might be obvious to you, but not to the other person. Being explicit about it! Expressing interest in learning helps set the stage for meaningful questions. For example:
“I’m curious about…”
“Could you help me understand…?”
Frame it as learning – Present your question as a chance to gain insights rather than challenge ideas.
“This is really interesting—how did you arrive at this solution? I’d like to learn from your process.”
Show respect for their knowledge – Start by showing you value what they know. This makes your question sound friendly and open to learning.
“You have more experience with this—could you share your perspective on why this works best?”
Final thoughts
The way we ask questions determines how people respond. Questions coming from curiosity rather than doubt, questioning, or insecurity lead to deeper understanding, stronger relationships, and better decisions.
So, the next time you hesitate to ask something, remember that the risk of not asking is often greater than the risk of speaking up.
Until next time,
Irina
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Asking questions from a tone of curiousity rather than defensiveness is a win-win, every time.
Great article, Irina! I have noticed some teammates using the questions below throughout my career.
“This is really interesting—how did you arrive at this solution? I’d like to learn from your process.”
“You have more experience with this—could you share your perspective on why this works best?”