Most managers are told the same thing:
- Ask more and better questions.
- Listen more than you talk.
- Create open-ended conversations.
Yes, I know, I’m one of those people who have told you all to do this over the course of many newsletters!
The good news is that many managers genuinely try to do these things and on the whole, they are great things to get better at.
But… despite good intentions, some of these conversations can still feel a little bit… limited.
You ask a question, then you get a short answer. So you try again, and you don’t get much more.
So it can be easy for us to assume that:
- They don’t have anything to say.
- Everything is genuinely fine.
- They’re just a quieter person.
Whilst these may well be true sometimes, there are other times when there is an issue, but it’s not because of the person.
It’s because of the question.
Small differences in how questions are asked can significantly shape what people feel able or willing to share.
Why well-meaning questions can limit conversations
This isn’t about managers asking “bad” questions.
It’s about how normal, well-intentioned questions can unintentionally narrow the conversation.
Managers default to efficiency
When time is tight, questions become shorter and more direct. Again, we don’t mean to rush things, but we can end up asking questions that are short and to the point, such as:
- “What’s the update?”
- “Any issues?”
- “Are we on track?”
These questions are efficient. They move things forward.
But they also signal that the conversation is about output, not reflection.
Questions reflect what the manager wants to know
We often ask questions based on what we need, not what our team needs. For example, we need things like the following:
- Status updates.
- Clarity on delivery of work.
- Progress against deadlines.
There is a subtle shift that happens here and most of us don’t notice it.
Instead of seeking to find out “what is actually going on”, the conversation becomes closer to “What do I need to know to keep things moving?”
And those are not the same thing.
People take cues from the question
This is a big one and one that we can underestimate the impact of. Basically, the fact that we’re someone’s manager and therefore, in a position of authority, means that every question that we ask sends a signal.
Our team is trying to work out what we want from a question and can sometimes feel the pressure of the authority that we hold.
When we ask a question, the person on the other end is trying to figure out:
- How much detail is expected.
- What kind of answer is appropriate.
- Whether it’s safe to go deeper.
If the question that you ask is narrow, the answer will be too. Remember, you are their boss, so many won’t feel comfortable with expanding their answer beyond what you’ve actually asked for.
If the question feels leading, the answer will follow that lead.
And over time, people adapt.
They learn what kind of answers are expected and they give them.
The types of questions that shut conversations down
You’ll probably find that the following questions are very familiar to you.
Closed questions
These are the types of questions that someone can easily say yes or no to. They don’t invite a more detailed answer.
Questions like:
- “Are you okay with this?”
- “Is everything going fine?”
- “Any issues?”
These invite a yes or no.
And even if someone does have something to say, the easiest response is: “Yeah, all good.”
The conversation ends before it really begins.
Leading questions
These are super easy to ask, especially if you are busy and if you want to get to a resolution or closure of the conversation quickly. So to do this, we ask questions in a way that may not be a straight yes or no, but they are likely to make someone just agree with us.
For example:
- “You’re happy with how that went, right?”
- “That wasn’t too difficult, was it?”
These suggest the “right” answer.
Even if unintentionally, they make it harder for someone to say something like “Actually, I found that quite difficult.”
So people follow your lead instead.
Task-focused questions (too early)
Again, these make us focus a little too much on the nitty gritty details of whatever is going on at the time.
Questions like:
- “What’s the update on the project?”
- “Where are we with this?”
- “What’s next?”
Again, nothing wrong with these in principle.
But when they come at the start of a conversation, they immediately move everything into delivery mode.
Anything outside of tasks becomes less likely to surface.
Rapid fire questions
I’ve noticed that managers who are a little bit nervous or a touch insecure in their role do this a lot. To try and compensate for a lack of confidence, they’ll sometimes ask several questions at once:
“How’s the workload? Are priorities clear? Any blockers?”
This can feel overwhelming for your team members. Not to mention that in practical terms, these aren’t all getting answered properly!
So instead of answering fully, people often default to the simplest response: “Yeah, it’s all fine.”
Questions followed by immediate problem-solving
I’ll admit that I used to do this a lot in the early years of my career – well before I started to learn that a good manager listens more than they talk!
The pattern of a meeting can be along the lines of:
- A manager asks a question.
- The employee starts answering.
- The manager jumps in with a solution.
Over time, the message becomes clear:
“This isn’t really a space to think out loud.”
So people stop trying.
Why this matters more than it seems
At least a few of you will be sitting there thinking that this just feels like a small communication detail.
But over time, it has a significant impact and it can spread across your team.
Conversations stay at surface level
One of the biggest benefits of spending one-on-one time with your team is that you can go deep into their challenges and learn more about them as a person. But if we’re not careful, our questions can lead to the opposite happening.
This means that you’ll miss things like:
- Early signs of struggle.
- Uncertainty.
- Frustration.
- Development needs.
This is because the conversation never quite gets there.
People stop bringing things up
Over time, you’ll accidentally train your team members to think that every conversation is going to be a series of questions that lead to a short, transactional exchange. As a result, they adjust their expectations of what those conversations are about.
They will stop thinking that the conversation is an opportunity to talk openly about their challenges and careers, whilst moving more towards thinking “this is where I give updates.”
How to ask better questions (without overcomplicating it)
Don’t worry – making this change and improving your skills here isn’t actually that complicated. We’re not talking about learning a completely new framework or way of thinking.
It’s more about making small, intentional shifts in how you approach a conversation.
Start broader, then narrow
Instead of starting a conversation with: “Any issues with the project?”
Try something like: “How are things feeling at the moment?”
Then follow up with questions such as: “What’s been working well?” or “What’s been more challenging?”
This creates space first and structure second. It also allows the person to bring up something that is on their mind but may not be part of the formal agenda or talking points.
Ask open ended questions
Focus on asking questions that invite explanation rather than confirmation.
For example:
- “What’s been on your mind recently?”
- “What’s felt difficult this week?”
- “Where do you feel least clear right now?”
These encourage people to think and share deeper responses, not just respond with a short sentence or a yes or a no.
Remove the “expected answer”
Remember how we said above that we can accidentally ask questions that just get someone to agree with us? This is the remedy to that.
So instead of saying: “You’re okay with this, right?”
You’re saying: “How do you feel about this approach?”
It’s a very, very small change, but you can easily imagine how the answers to these questions will differ.
Listen without immediately solving
This is one of the hardest habits to shift – I know because I’ve tried!
But also one of the most valuable.
Try a little harder to:
- Let people finish.
- Let them think out loud.
- Let them explore the problem.
Sometimes, they don’t need a solution from you.
They just need space to reach clarity themselves.
Most managers don’t struggle because they’re not asking questions.
They struggle because the questions they ask unintentionally limit the conversation.
It’s not an impossible one to solve. You don’t need loads more time or a new fancy system. You just need slightly better questions.
Because people usually have more to say than they initially share.
The role of a manager isn’t to extract it.
It’s to create the conditions where it feels natural to say it.
And that starts with how you ask the question.
