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

Athena Williams • February 8, 2026

Share this article

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.

Recent Posts

Business meeting in a glass-walled office, with a woman speaking to seated colleagues.
By Athena Williams • October 15, 2026
Transformation creates an interesting tension for leaders. As the pace and complexity of transformation increase, we tend to focus on what the organization needs to do differently: new strategies, structures, technologies, operating models, priorities. But there is another question that matters just as much: Are you building the leadership capacity required to lead what you are creating? We think of this as the acceleration gap: the distance between the ambition and pace of transformation and the leadership capacity available to make it happen. It is a gap that rarely appears in the transformation plan or budget, yet it can become very expensive in execution. And because it isn't always recognized as a leadership capacity issue, its symptoms are often attributed to something else: resistance, slow execution, competing priorities, poor decisions, or individual leaders who appear to be struggling. But transformation doesn't just ask more of the organization. It asks more of its leaders. More ability to navigate uncertainty. More strategic thinking. Faster decisions. Greater adaptability. More capacity to align people around priorities while continuing to deliver today. And when that capacity doesn't grow alongside the demands of transformation, the gap eventually becomes visible. Here are three places to look:
By Athena Williams • October 10, 2026
Every transformation creates new demands on the people expected to lead it. We spend significant time planning what needs to change, the strategy, technology, structure, operating model and ways of working. But we spend far less time asking whether leaders are ready for what those changes will require of them.
Colleagues meeting around a laptop in a bright office conference room, discussing documents and notes.
By Athena Williams • October 3, 2026
Most successful leaders have a playbook. You’ve built it over years of experience. You know how to make decisions, mobilize people, solve problems, deliver results and navigate pressure. That playbook is part of what got you here. But transformation has a way of changing the game. The environment becomes more complex. Decisions become more interconnected. The number of stakeholders increases. Teams are expected to deliver today's results while simultaneously building something that may look very different tomorrow.
Two colleagues walking through a modern office hallway, talking as coworkers in glass meeting rooms work nearby
By Athena Williams • September 26, 2026
By the time you reach the final quarter of the year, your team has already lived a lot of life together. Priorities have shifted. Plans have changed. Some goals have been achieved, others have quietly slipped. There may have been reorganizations, new leaders, departures, launches, disappointments and more than a few things nobody anticipated back in January. And yet this is often the moment leaders ask their teams to push harder.
Team collaborating at a computer in a modern office, focused on a screen.
By Athena Williams • September 19, 2026
For decades, organizations prized specialists. Then came the idea of the T-shaped employee: deep expertise in one discipline, represented by the vertical line of the T, combined with enough breadth across other disciplines to collaborate effectively, represented by the horizontal line. The emerging idea of the X-shaped employee, recently discussed by Shopify COO Jess Hertz, takes this further. An X-shaped person doesn't simply possess expertise and breadth. They can cross boundaries, connect disciplines, work effectively with other experts and contribute beyond the confines of their own role. And I think this idea becomes even more important when we apply it to leadership.
Team meeting in a glass office, with a woman speaking to seated colleagues.
By Athena Williams • September 12, 2026
Hope may not appear on your transformation roadmap, but perhaps it should. Transformation depends on people being willing to invest effort today in a future they cannot yet fully see. When people stop believing that the future is possible, transformation can quickly become another initiative to survive rather than something they are actively helping to create. And this applies to you, too. Senior leaders are often expected to carry confidence for everyone else while privately navigating their own uncertainty, frustration and fatigue. Holding onto hope doesn’t mean convincing yourself everything will work out exactly as planned. It means maintaining a grounded belief that something better is still possible, and continuing to lead toward it.
Person on a video call at a desk, viewing multiple participants on a computer screen.
By Athena Williams • September 5, 2026
Resistance during transformation rarely announces itself with, “I don’t support this.” More often, it hides in plain sight. People agree in the meeting, then continue operating exactly as they did before. Decisions get revisited. New processes are adopted inconsistently. Leaders say they support the transformation while continuing to reward old behaviors. Teams ask for more clarity when what they may really need is greater confidence, capability, or trust.
Two professionals standing with arms crossed in a modern office, smiling at the camera
By Athena Williams • August 29, 2026
One of the great paradoxes of transformation is that leaders must create urgency while also having the patience to build something that lasts. Executives are rewarded for moving quickly. You make decisions, solve problems, push through barriers and expect progress. During transformation, those instincts are valuable, until speed becomes the measure of success.
People in a glass-walled conference room discussing around a table in a modern office
By Athena Williams • August 21, 2026
One of the greatest risks in transformation is not that your organization will resist change. It is that everyone will agree to change, and still never transform. We see this with senior leadership teams all the time. There is a bold ambition at the beginning, a new strategy, operating model, organizational structure, technology platform, customer experience or way of working. Leaders talk about doing things differently. Then the machinery of the organization kicks in.
Man working at a laptop in a modern office, with a notebook beside him.
By Athena Williams • August 15, 2026
When transformation gets difficult, even experienced leaders can fall back on what made them successful in the first place: expertise. You see the problem, you know what should happen, so you step in. That can work beautifully in the short term. But if you become the person everyone depends upon for direction, decisions and problem solving, you may inadvertently create the very thing transformation cannot afford: organizational dependency on you.
Show More