What’s Clouding Your Mind Today?
Most workplace conversations start with autopilot questions and autopilot answers. Here’s how to open the door to something deeper.
Yesterday, I was chatting with a school psychologist. I asked her what the first thing is that she asks a student when she sits down with them to talk.
She said, “I always start the same. I ask, ‘What is clouding your mind today?’”
That question stuck with me. And I started thinking, “Man, that’s a great question.” But the more I thought about it, the more I realized this isn’t just a good question to ask students. It’s a good question for the rest of us, too — especially when we’re talking with people we work with.
Think about how those conversations normally start:
“How’s it going?”
“What can I do for you today?”
“How can I help?”
“What’s new?”
I’ve heard all of these over the years. I’ve asked most of them myself. Here’s the truth: none of those are actual conversation starters. They don’t open anything up. They’re too generic to mean much and too familiar to sound like genuine curiosity. They’re autopilot questions that produce autopilot answers. “Fine.” “Not much.” “All good.”
Most of them are really just polite greetings pretending to be conversation starters. Others sound like you’re an order taker waiting for instructions. And the common problem with all of them is that they ask the other person to carry the work of the conversation without giving them a clue about where to even start. They basically say, “You figure out what we should talk about.”
🧭 Why the First Question Matters
What you open with matters more than most of us realize. If it’s a quick “How’s it going?” that tells them it’s going to be a surface-level check-in. If it’s a more intentional question, that signals a conversation that matters.
Those first 30 seconds do more than break the ice. They set the tone. They tell the other person whether this is about brainstorming, problem-solving, reflection, or support. And they influence how much that other person will want to share.
If you start vague, the answers stay on the surface. If you start with a thoughtful question, the conversation goes deeper.
It’s also a matter of trust. Most people walk into a one-on-one with a lot on their mind that they’ll never say out loud: deadlines, stress, frustrations, questions. A question like “What’s clouding your mind?” doesn’t demand that they unpack it all. But it does give them permission to be honest. And that’s usually where the real insight is hiding.
I know this because I’ve been on the other side of these conversations. For way too long, my default opener was, “How’s your week going?” And almost every time, I got the answer, “Great.” It didn’t matter if their week was actually great or not. It wasn’t that they were lying to me — it’s just that I had set the bar so low that “great” was the safest response possible.
That’s when I realized something important. If you start vague, you will stay vague. If you want to get real insight, you have to ask for it.
🛠️ A Toolkit for Better Conversations
So what should you start with instead? One option is to ask something specific and forward-looking to signal that you’ve been thinking about their work:
“I’ve been thinking about our Q4 content calendar. Where do you feel like we have the most momentum right now?”
“How did the donor pitch go yesterday?”
“I saw your draft on the housing series. What’s your instinct on the framing?”
Another option is to make space for reflection:
“What’s been on your mind this week?”
“What’s taking up the most headspace for you right now?”
These kinds of questions can signal that you’re curious and give the other person a lane to respond in. They also help you skip over the small talk and get to a real conversation faster.
I started opening my check-ins with a version of “What’s been weighing on you this week?” and the difference was immediate. Instead of quick status updates, I started hearing about the real work: the stuck points, the unexpected wins, the ideas that weren’t ready to be shared yet. It turned my one-on-ones from updates into collaborations.
I could put together a whole list, but here are a few more ideas to try:
To spark reflection:
“What’s felt most rewarding — or most frustrating — this week?”
“What’s been sitting at the back of your mind that we haven’t talked about yet?”
To get strategic:
“What feels like the biggest lever for impact right now?”
“If you had one extra day this week, where would you put it?”
To build trust:
“What’s one thing you wish I understood better about your role?”
“Where could I be more helpful as a manager or partner?”
☁️ The Invitation
I haven’t had a chance to use that psychologist’s question yet. I only heard it yesterday. But I will. And I’m already curious to see what happens when I do.
I imagine the conversations will be deeper and more honest. Not because the words themselves are magic, but because they carry an invitation that most of our workplace questions don’t. They assume there’s something worth naming. And they make it safe to bring it forward.
So here’s the invitation. Change the first question you ask someone this week. Make it sharper. Make it braver. Make it more curious. Then see how the conversation changes.
Before you leave, I’d love to hear from you. What’s the best opening question you’ve ever been asked in a one-on-one — or one you now use yourself? Drop it in the comments. I’m curious to see what’s working in real conversations.
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