When Executives Don’t Know What to Talk About in Coaching

A simple question often unlocks awareness

In my executive coaching practice, every engagement begins with a foundation of insight. I often start with assessments — 360° feedback from colleagues, upward feedback from team members, and a range of personality, leadership, or emotional intelligence assessments. These tools are invaluable. They help my clients reflect on their strengths, challenges, and blind spots, and they guide us in shaping the focus areas for our coaching journey.

Yet, even with all this data in hand, it’s not uncommon for some executives to arrive at a session unsure of what exactly they want to talk about.

This doesn’t mean they lack challenges or growth opportunities. In fact, it’s often the opposite. Sometimes they’re overwhelmed, other times they’ve had a demanding week and come less prepared. And occasionally, it’s simply that they haven’t paused long enough to connect inward and recognize what truly needs attention.

When this happens, my first instinct is empathy — not urgency. I remind myself that coaching is a space for reflection, not performance. I start with a friendly, open conversation. We talk about what’s been keeping them busy, or I revisit the actions they took accountability for in our previous session. Almost always, within a few minutes, the real topic surfaces — something that’s been sitting beneath the surface waiting to be explored.

There are other ways I help my clients access clarity. One of my favorite prompts is:

“If I were to call your boss right now and ask what one priority development area you should focus on, what do you think they’d say?”

This simple question often unlocks awareness. It helps the client step outside themselves and view their development from another’s perspective. And in that moment, we often land right where we need to — the true focus of the session.

At the heart of effective coaching lies self-awareness — the ability to acknowledge one’s opportunities for growth and see how addressing them connects directly to achieving personal or business goals. When this clarity is missing, I see it as my responsibility to nurture it. My role as a coach is not just to help clients find answers, but first to help them discover the right questions.

Time and again, this approach has yielded profound results. Clients leave these sessions not just with an action plan, but with a renewed sense of self-understanding. And when I ask at the end, “What did you learn about yourself today?”, the aha moments are both humbling and rewarding.

Those moments remind both of us of the true value of coaching — the power of curiosity, empathy, and genuine belief in human potential. Because sometimes, the most powerful coaching starts not with a clear agenda, but with a caring conversation.

If you’re an executive seeking greater clarity, impact, or self-awareness, I invite you to explore how coaching can help you unlock your full potential. Reach out for a discovery conversation — a space to reflect, refocus, and reimagine what’s next for you as a leader.

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