Andy has been losing sleep. He’s a real estate broker with a mid-sized company who has done well over the last few years. But with all the changes in federal policy, he’s increasingly worried. Much of what concerns him right now feels largely out of his control.
We’ve all been there, right? And many of us are losing sleep these days. It can feel as though the world is changing in ways that are nearly impossible to keep up with.
As a coach and trainer, I have a growing suspicion that I could offer more to potential clients like Andy if I better understood what they truly need. Not just what they say they need on a good day, but what shows up in the quiet hours. I want to understand their “wake-up worried” problems — the thoughts that surface at 3 a.m. — and what they most deeply yearn for underneath those concerns.
To that end, I’ve begun a series of short interviews (15 to 20 minutes) with people in business. Some are employed, like Andy, in brick-and-mortar organizations. Others are self-employed or running their own ventures. I ask them questions about what’s challenging them right now. These are not sales calls. My goal is simply to listen and learn. I’m taking my time with this process because I know that asking the right questions matters.
A powerful question is like a key in a door. It opens access to lived experience, emotion and insight. It can quickly deepen a conversation and build trust in the interaction. In my experience, strong questions are one of the most important elements a coach brings to their practice.
Here are the questions I’m currently working with. They evolve depending on who I’m interviewing, but the intention stays the same: to move beyond surface-level problem solving and into something more human and useful.
Current focus/context
“Tell me a little about what you’re working on right now in your role or your business.”
I often listen for what feels most urgent or demanding, what’s taking the most energy —mentally or emotionally — and what a “full” week actually looks like. This question sets the landscape without judgment. It anchors the conversation in reality.
Friction points
“Of everything you just described, what’s been most challenging or frustrating lately?”
Here, people often reveal where things slow down, get messy, or feel heavier than they should. I’m curious whether the challenge is new or long-standing and what prompts the quiet thought, “This shouldn’t be this hard.”
Lived impact
“How does that challenge show up for you day to day?”
This question tends to shift the energy in the room. We move from logistics to impact: mood, confidence, energy, sleep. People notice whether the challenge spills into evenings or time off and whether it leads them to second-guess themselves, push harder or quietly pull back.
Desire for support
“If you could wave a wand and get support in one area of your work, where would it be?”
This is where longing appears. The answers often surprise people. Is the need about clarity, confidence, skills, accountability, or simply space to think? What would actually be different if that support were in place?
Barriers to getting help
“What tends to stop you from getting the help you know you could use?”
Here we uncover time, money, trust, past experiences or something harder to name. Sometimes it’s the belief that they should be able to handle this on their own. Sometimes it’s a memory of help that didn’t quite land.
Key takeaways
Andy may never know how many other people wake up at 3 a.m. with the same tight chest and looping questions. But that’s the quiet common ground I’m listening for in these conversations. Beneath strategy and skill gaps, there’s almost always a very human mix of worry, responsibility and hope.
These interviews are my way of slowing down long enough to hear that clearly — to understand not just what’s broken, but what people are trying to protect, build or hold together.
When we listen at that level, better questions emerge, and with them, more honest forms of support. My hunch is that if we can name the “wake-up worried” moments with care, we can also begin to imagine what might help people sleep again.
