Questions to ask an executive coach before engaging

You've decided coaching might help, but you're not sure if a particular coach is worth your time and money. The questions that matter aren't about credentials alone—they're about fit, method, and whether this person can actually help you move. Here's what to ask, why it matters, and how to spot a coach who thinks clearly versus one who's selling a promise.

Does this coach ask about the real situation first?

Before a coach tells you what they do, they should ask what you're trying to fix or build. A strong opening question sounds like: "What brought you to explore coaching right now?" or "Tell me about a specific situation where you're stuck." Listen for genuine curiosity, not a rush to diagnose.

If they launch into their process, their philosophy, or what coaching "typically" achieves before understanding your world, that's a yellow flag. A good coach wants to know your industry, your team size, recent wins and failures, and the actual blocking point—not because they need to fix you, but because coaching only works when it's anchored to something real. Watch too for coaches who minimize your challenge ("That's common, we fix that") versus those who dig deeper ("Help me understand what makes your situation different").

How do they measure whether the coaching is working?

Ask directly: "How will we know if this is working? What will be different?" A coach who umms and says "You'll just feel it" or "You'll be more authentic" is vague in a way that lets them off the hook. Better answers sound like: "By week six, you should be clearer on whether you want to stay in that role, and we'll have talked through what moving looks like" or "We'll define a leadership behaviour you want to shift, and you'll track how your team responds over three months."

Good coaches tie progress to observable change—something you or your manager or your team would notice, not just an internal feeling. They also name what they can't promise. A coach might say, "I can help you lead differently, but I can't guarantee your boss will respond the way you hope," or "We can work on your confidence, but I'm not a therapist if this is rooted in deeper anxiety." That honesty is trustworthy.

What happens if we're not clicking or if nothing shifts?

Ask how the engagement ends and what happens if it's not working. A coach who says "Let's try six sessions and check in" is safer than one who locks you into twelve months upfront with no exit clause. Good coaches build in review points—often at session four or six—where you both honestly assess whether to continue, change approach, or stop.

Also ask what they expect from you between sessions. Coaching isn't passive; coaches typically set small actions or reflections for you to do. If a coach doesn't mention this or says "Just come to the sessions," they're not setting you up for real change. A solid answer is something like: "Between our calls, I'll send you one or two things to observe or try—usually takes twenty minutes. We'll unpack what happens." That signals they're designing the work, not just chatting.

Push on their cancellation or refund policy too. If a coach is reluctant to let you stop or renegotiate, their incentive is the fee, not your progress.

What's their take on confidentiality and feedback loops?

If your company is paying, ask: "What will you report back to HR or my manager?" A coach should be clear—typically they don't share session content, but they might report on whether you're engaging and whether goals are tracking. If it's entirely secret, your manager won't know you're working on leadership change, which wastes the opportunity. If your coach tells your boss everything, that kills trust.

Also ask whether they'll help you gather feedback from your team or peers. Some coaches do 360-degree surveys or interviews; others work purely from your own reflection. Neither is wrong, but you should know which, because it changes the coaching.

The strongest coaches ask good questions, admit what they can't fix, measure progress against something real, and treat the engagement as a partnership you can pause or end. When you're vetting coaches on Strove, use these questions as your interview script—a responsive, straight-talking coach will welcome them.