How To Feel Comfortable Asking The Most Important Question At Work

Forbes

21-05-2025

How To Feel Comfortable Asking The Most Important Question At Work
Since my work focuses on helping people develop curiosity, I get asked a lot whether there is such a thing as a bad question. Technically, there can be. If a question is meant to trap someone, push an assumption, or make another person feel under attack, it's not helpful. But more often, the good questions never get asked at all. People hold back. A study in the Harvard Business Review showed that employees are far more likely to speak up when they feel psychologically safe. Without safety, people stay quiet or rely on safe, scripted questions that don't move the conversation forward. There's one question everyone should feel comfortable asking: "What are we not asking?" It gives people permission to bring up what they've been thinking but haven't said out loud. It slows things down in a good way and opens the door to a more honest, thoughtful discussion. That question is a great place to begin. Getting more comfortable with asking questions starts by understanding how they land, what holds people back, and why tone and timing matter.
What Types Of Questions Develop Conversations?
When I hosted my radio show, I learned quickly that a yes or no question could stop a conversation in its tracks. If I asked, "Do you like your job?" and the guest said "yes," there wasn't much to follow. But if I asked, "What part of your work keeps you up at night?" or "What made you take that role in the first place?" I'd hear real stories and insights. The same thing applies at work.
Some questions feel safer than others. Closed-ended ones, like "Did you finish the report?" are simple, but they can shut down a deeper conversation. If the answer is more nuanced, it gets lost. That kind of question might get a quick response, but it doesn't offer much clarity. Try asking something like, "What do you still need to get done today?" That gives the person space to share where things really stand.
Closed questions are useful when you need a clear answer. But when you're trying to understand what someone is thinking, open questions work better. They make it easier to have a real conversation. They also help the person asking feel more engaged, because the dialogue feels less like a checklist and more like a connection.
Why Do Some Questions Come Across As Confrontational?
Tone, timing, and phrasing matter. A question like, "Why didn't you speak up in that meeting?" might come from a good place, but it rarely feels that way. A better approach would be, "Was there anything that made it harder to speak up earlier?" That feels softer, making it more like an invitation than a challenge.
Even a good question can be delivered badly. When tone feels sharp or the question lacks context, people can feel backed into a corner. That's when the conversation you intended can turn into more of a reaction.
This happens often in email. I've had people read me an email aloud in a snarky tone, hoping I'd confirm how awful the sender was. But without knowing the person, I don't hear it that way. We tend to fill in tone based on past experiences. If the last interaction with someone was tense, even a neutral question can feel terse. That's why questions in writing need extra attention. It helps to go back and read what you wrote several times to look for how it might be received.
What Happens When Questions Are Used Just To Fill The Silence?
Some questions are asked just to break the silence. No one knows what to say, so someone speaks up to keep things moving. But when a question has no clear purpose, people notice. Those kinds of questions don't go anywhere.
I've been interviewed by people who asked empty or canned questions. The worst is when someone asks something, ignores the answer, and jumps to the next topic like they're reading from a script.
It's better to ask fewer questions that matter. As an extravert, I understand that dead air gives people like me some anxiety. However, sometimes pausing can be the best thing you can do. Giving people space to think usually leads to better answers. Instead of avoiding silence, ask yourself, "What do I actually want to know right now?" Then stop and let people have time to answer without you filling in the blanks for them.
How Do Assumptions Get In The Way Of Asking Good Questions?
Assumptions can sneak into how we phrase things. A question like, "How are you adjusting to the new system?" assumes the person is already adjusting. A better version might be, "What's working with the new system, and what's still a challenge?"
When a question carries a built-in assumption, people are less likely to respond openly. It feels like the answer has already been decided for them. Dropping that framing gives others more room to respond honestly. Curious questions come from a place of wanting to learn what hasn't been said yet.
What Do Comfortable, Useful Questions Sound Like?
A good question feels like an opening. It's clear, simple, and open enough to take the conversation in different directions. Questions like, "What's getting in the way right now?" or "What's something we might be missing here?" tend to spark more real answers.
People respond to tone. When someone hears a question that comes from genuine interest, they're more likely to share. That kind of trust builds momentum. And the more often someone has a good experience asking or answering a question, the more likely they are to keep going.
How To Build Comfort With Asking Hard Questions
If you're not used to speaking up, start small. You don't have to ask the hardest question in the room right away. Begin with clarifying questions that show you're engaged, like "Can you walk me through the thinking behind that decision?" or "What's the main goal we're trying to reach here?" These feel natural and nonthreatening but still move the conversation forward.
Practice rephrasing tough thoughts into open-ended prompts. Instead of saying "I don't think this will work," try asking "What challenges do you think we might run into?" It keeps the door open without putting people on the defensive.
What Are Some Of The Most Important Questions That Often Go Unasked?
Some of the most powerful questions are the ones people aren't sure they're allowed to ask. These include:
When questions like these are welcomed, people start to feel safer being honest.
Why Do These Questions Matter So Much?
Most people have been in a meeting where the right question could have changed the direction of the conversation. But no one asked it. Sometimes it's fear. Sometimes it's habit. And sometimes it's just easier to stay quiet. Getting more comfortable asking questions like "What are we not asking?" takes practice, awareness, and a willingness to make room for whatever might come next. Asking a good question is what leads to better conversations, builds trust, and makes work feel more open, more thoughtful, and more productive.