The Coaching Questions You May Hesitate to Ask Your Team (But You Should)

The beginning of the year is a powerful inflection point. Expectations are being formed, assumptions are solidifying, and unspoken narratives take root quickly. Yet many leaders default to telling rather than asking—often out of concern about unsettling the team, surfacing discomfort, or appearing uncertain.

Research from leading business schools consistently shows that leaders who use inquiry rather than directive control build stronger engagement, higher accountability, and better decision quality over time. 

From a neuroscience perspective, thoughtful questions activate the brain’s prefrontal cortex, supporting reflection, ownership, and creative problem-solving rather than triggering threat-based, defensive responses.

Here are five coaching questions leaders often hesitate to ask at the start of the year—and why they matter.

1. “What feels unclear or unrealistic about our priorities right now?”

Leaders often assume silence equals alignment. It doesn’t. This question invites honesty before misalignment becomes frustration or quiet disengagement. It also signals that clarity is a shared responsibility, not a top-down mandate.

2. “Where do you feel most stretched or most constrained by how we’re working?”

This question surfaces structural and emotional friction early. It helps leaders identify whether pressure is coming from workload, process, decision bottlenecks, or role ambiguity—before it shows up as burnout or underperformance.

3. “What are you most confident about this year and where do you feel less certain?”

Many leaders worry this question will expose weakness. In practice, it builds trust and psychological safety. It also allows leaders to calibrate support, resources, and expectations with far greater precision.

4. “What would meaningful success look like for you personally this year?”

This shifts the conversation from metrics alone to motivation and meaning. When leaders understand what success means to their people—not just what it measures—they can align work in ways that sustain energy and commitment.

5. “What do you need more of (or less of) from me to do your best work?”

Perhaps the most uncomfortable question of all. And often the most powerful. This invites feedback in real time, rather than after trust has eroded or performance has slipped. It models humility and strengthens the leadership relationship.

Asking these questions doesn’t mean relinquishing authority. It means expanding leadership capacity—yours and your team’s—by creating space for truth, ownership, and shared clarity.

Leadership Practice

Choose One Question. Create One Conversation.

This week, select one of the questions above and intentionally use it in a 1:1 or team conversation.

As you ask it:

• Pause. Resist the urge to fill the silence.

• Listen for both content and emotion.

• Reflect back what you hear before responding or problem-solving.

Afterward, note:

• What surprised you?

• What shifted in the quality of the conversation?

• What action or follow-up is now needed from you as the leader?

Small moments of inquiry, practiced consistently, create powerful leadership momentum over time.

Author

Athena Williams, Founder and CEO of Tenacious Leadership Institute, partners with senior leaders and organizations navigating complex transformation at scale. For more than two decades, she has supported executives at global companies including Fortune 500 and high-growth organizations to strengthen leadership capacity, accelerate transformation, and deliver results that hold under pressure.

Her work sits at the intersection of neuroscience, leadership behavior, and execution - helping leaders think clearly in complexity, lead decisively through disruption, and align teams and organizations during critical inflection points. Through executive coaching and leadership development programs, Athena supports transformation that shows up in stronger decisions, sharper execution, and sustained performance across people, teams, and the enterprise.

Take the next step in strengthening how you lead transformation.