If you’ve ever hesitated to speak up in a meeting or held back a question because it felt too bold, you’re not alone. Many professionals wonder how to feel comfortable asking the most important question at work—especially when the room feels tense or uncertain. The truth is, asking questions isn’t just a sign of curiosity, it’s a leadership skill. And one question stands out for unlocking honest conversations: “What are we not asking?”

This question creates space for overlooked concerns, unsaid thoughts, and meaningful dialogue. But to ask it confidently, it helps to understand why people hold back, what makes a question effective, and how to shift your mindset around curiosity and communication.

Why We Hold Back From Asking Bold Questions

Studies, including one published by the Harvard Business Review, show that employees are far more likely to speak up when they feel psychologically safe. Without that sense of safety, even the smartest questions can stay unspoken. People worry about sounding challenging, exposing gaps in knowledge, or rocking the boat. As a result, conversations often stick to the surface—and progress stalls.

How to Make Questions More Thoughtful and Engaging

A good question moves a conversation forward. That means asking open-ended questions that invite real answers. Instead of saying, “Did you finish the report?” try, “What’s still on your plate today?” It’s a small shift, but it changes the tone from checklist to collaboration.

When you want to understand how someone’s feeling or thinking, avoid yes-or-no formats. Ask questions like, “What was the biggest challenge in this project?” or “What made you choose that approach?” These kinds of questions open the door to deeper understanding.

How Tone and Timing Shape the Impact of a Question

It’s not just what you ask—it’s how you ask it. A question like “Why didn’t you speak up earlier?” can sound accusatory, even if it’s well-intentioned. Rephrasing it as, “Was there anything that made it hard to speak up earlier?” makes it feel more like an invitation and less like a challenge.

Tone matters even more in writing. In emails or messages, people often read tone based on their last experience with you. A neutral question can come off as harsh if trust hasn’t been built. That’s why reviewing your message before hitting send can make a big difference in how it lands.

Avoiding “Filler” Questions That Don’t Go Anywhere

Sometimes, people ask questions just to fill silence. These often feel generic or disconnected—like they’re coming from a script. Instead, pause and ask yourself, “What do I genuinely want to know right now?” One thoughtful question is more valuable than five rushed ones. Silence can be uncomfortable, but letting it breathe gives others the chance to think—and respond meaningfully.

How Assumptions Can Undermine Your Question

Assumptions can sneak into your questions and make others feel boxed in. For example, asking “How are you adjusting to the new system?” assumes they are adjusting. A better way to phrase it: “What’s working well with the new system, and what’s still challenging?” That phrasing leaves room for honest input.

Being curious means staying open to what you don’t know yet. Questions that are free from assumptions allow others to speak freely, without feeling judged or led toward a specific answer.

Examples of Questions That Truly Open Up Dialogue

Some questions make people pause—in a good way. They invite honesty, creativity, and clarity. Here are a few powerful ones that often go unasked:

• What are we not talking about that we should be?

• What’s something that doesn’t feel right but hasn’t been said yet?

• What would you do differently if this were your decision?

• What are we assuming that might not be true?

• What’s a risk we’re not acknowledging?

When these kinds of questions are welcomed in the workplace, trust grows and new solutions emerge.

How to Build Confidence in Asking the Tough Questions

Start small. You don’t have to challenge the entire strategy on day one. Begin with questions that show engagement, like, “Can you walk me through the thinking behind that?” or “What’s our main goal here?” These kinds of questions feel constructive and curious—not confrontational.

Also, try turning your concerns into open-ended prompts. Instead of saying, “This won’t work,” ask, “What might stand in our way?” This approach fosters collaboration while still raising important issues.

Why Asking the Right Question Changes the Conversation

The right question at the right time can shift the entire direction of a meeting. “What are we not asking?” is one of those questions. It shows courage, thoughtfulness, and leadership. And it creates the kind of environment where people feel safe to share what really matters.

Whether you’re early in your career or managing a team, learning how to feel comfortable asking the most important question at work will help you build better conversations, stronger relationships, and a more open workplace culture.

If this helped you rethink the way you ask questions, consider sharing it with a colleague—or try asking one of the questions above in your next meeting. You might be surprised by what comes up.