The Questions Executive Coaches Ask (That You Can Ask Yourself)
- Merve Kagitci Hokamp
- Jul 21
- 6 min read
Last week, I was having drinks with a friend who's spent 20+ years climbing the ladder at the same company - a global giant with great reputation.
Smart, capable, respected — by any external measure, she's crushing it. But when I asked if she was happy, she gave me that look.
You know the one. The conflicted, "I mean... I should be grateful for what I have... I'm happy enough... but I'm not fulfilled... Not exactly... but complaining would be ungrateful... but if I'm honest about being unhappy, then what?" look.
"This is the best option out of all the options available to me," she said.
I couldn't help myself. "What are the other options?"
She started listing them like she was reading from a script: "I could go to our competitors, but they're not any better. I could take a position at a smaller company, but that would be a step backward. I could look at adjacent industries, but they'd probably pay less..."
Each option sounded like a variation of her current set-up. A different flavor of the same flavor.
Here's what I noticed: she was thinking about change like she was rearranging furniture in the same room. Moving the couch from one wall to another. Incremental shifts within the same four walls.
But real change - the kind that actually matters - doesn't start with "what's available." It starts with a blank canvas.
What do you actually want?
What are you genuinely good at?
What would you build if you were starting from scratch?
What does the world need more (or less) of?
This is my friend I'm talking about and we were out for a social gathering, so we didn't launch into a full coaching session. But watching her face shift as we talked —that moment when someone realizes they've been asking themselves the wrong questions entirely— it reminded me how easily we box ourselves into impossibly small corners. The questions seemed to shake something loose in her (in a good way, I think). It's funny how obvious it sounds in hindsight, but we so rarely pause to examine the assumptions driving our choices.
Why Leaders Get Stuck
Here’s what I notice about the leaders who book coaching sessions with me: They’re not stuck because they lack intelligence, experience, or options.
They’re stuck because they’ve been solving for the wrong variable. They’ve been asking questions like:
“What’s the next logical step?”
“What would look good on paper?”
“What’s the safest choice?”
Instead of:
“What’s actually fulfilling?”
“What do I want to learn next?”
“Where do I feel most alive?”
The result is a slow drift into inertia, even in high-functioning, high-achieving lives.
The ROI of Asking Better Questions
Research shows that executive coaching delivers a 788% ROI, but here's what the studies don't capture: the breakthrough moments rarely happen when I'm giving advice. They happen when I ask the question that stops a client mid-sentence, the one that makes them go quiet for thirty seconds before saying, "I've never thought about it that way."
Like Sarah, a VP who came to me convinced she was "bad at conflict." Three months of trying to fix her conflict skills had gotten nowhere. Then I asked her: "What if you're not bad at conflict — what if you're just really good at avoiding it?" The shift was immediate. She wasn't broken; she was strategic. She just needed to be strategic in a different direction.
Good coaching questions do something most advice can't: they help you think differently about what you already know. They create space between you and your assumptions. They interrupt the mental loops that keep you stuck.
As Jim Knight puts it: "Good questions open up conversations, generate respect, accelerate learning, and build relationships." Research from the Instructional Coaching Group shows that when leaders learn to ask better questions, they increase productivity by 88% compared to traditional training alone.
Here’s something I’ve noticed — both in my work with people and in myself: It’s easy to get swept up in the day-to-day. Meetings, decisions, deliverables… and before you know it, weeks go by without really pausing to zoom out.
We’ll spend hours digging into market data or prepping for performance reviews — but rarely take five quiet minutes to ask:
→ What am I avoiding here?
→ What story am I telling myself about this situation?
It’s not that we’re doing it wrong. It’s just that we often forget to check in with ourselves.
So, if you’d like to give yourself a mini-coaching session, start with these prompts:
The Questions That Cut Through the Noise
When you're stuck in decision paralysis:
"What would I do if I knew I couldn't fail?"
"What would I do if I knew I would fail, but it would be worth it anyway?"
"What's the smallest step I could take that would give me more information?"
When you're feeling overwhelmed:
"What am I making this mean about me?"
"What would this look like if it were easy?"
"What would I tell my best friend if they were in this situation?"
When you're avoiding a difficult conversation:
"What's the cost of not having this conversation?"
"What story am I telling myself about what will happen?"
"What would my future self thank me for doing right now?"
When you're questioning your leadership:
"What would I need to believe about myself to act with confidence here?"
"What would someone who respected me see in this situation?"
"What's one thing I've handled well that was harder than this?"
I asked that last question to Marcus, a new director who was convinced he was "in over his head." He went quiet for a full minute before saying, "I rebuilt our entire customer service process during COVID with half the staff." Sometimes we need permission to remember our own competence.
The Meta-Question That Changes Everything
But here's the question that sits behind all the others, the one that transforms how you think about challenges:
"What if this is exactly where I'm supposed to be?"
Not because everything happens for a reason (please). But because resistance to your current reality takes up the energy you need to navigate it.
When you stop fighting where you are, you can start working with what you have.
I learned this from a client who was furious about a reorganization that "ruined" her carefully planned career trajectory. After weeks of trying to help her accept the change, I asked:
"What if this chaos isn't happening to you — what if it's happening for you?" She got the promotion she'd been chasing for two years. Not despite the chaos, but because of it.
How to Actually Use These Questions
Here's what doesn't work: Reading these questions once and expecting them to change your life.
Here's what does work:
Pick one question that makes you a little uncomfortable
Sit with it for five minutes without trying to answer it
Notice what comes up — the resistance, the stories, the automatic responses
Ask it again tomorrow
The questions aren't tests. They're tools. And like any tool, they get more useful with practice.
Why This Matters More Than You Think
The research is clear: 86% of companies report recouping their investment in coaching, but the real impact isn't measurable in ROI spreadsheets. It's in the moment when a leader stops trying to force a solution and starts asking what they can't see yet.
Michael Bungay Stanier, author of "The Coaching Habit," puts it perfectly: Coaching happens in conversations of 10 minutes or less. It's not about lengthy therapy sessions or complex frameworks. It's about asking the right questions that trigger introspection, alternative thinking, curiosity, and motivation.
The questions executive coaches ask are designed to help you see what you already know but can't access when you're inside your own head.
You don’t need a new plan. You need a better lens — and that starts with the right question.
Hi, I’m Merve 👋
I work with ambitious leaders who want to show up with confidence, clarity, and control.
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