When a Leader Needs a Better Question

An experienced leader may know the options and still find a decision difficult.

They understand the budget. They know the board's expectations. They can describe the staff implications. What they need to work through is how much uncertainty they are prepared to accept, which responsibility matters most, or what they have been reluctant to say aloud.

I value coaching for that kind of conversation. Leadership asks people to exercise judgment with consequences attached. Having a place to examine that judgment carefully is a worthwhile form of support.

My executive experience informs the questions I ask. It also reminds me to check whether a situation resembles something I know or only appears to. The leader in front of me has their own knowledge of the organization, relationships, and constraints.

Find out what kind of help is needed

Imagine a hypothetical executive weighing a new partnership. The proposed work serves the mission, and the funding looks promising. The executive is uneasy about the delivery schedule and the influence the partner would have over the program.

Advice about a standard partnership agreement might be useful. So might financial analysis or consultation with someone who has the relevant expertise. A coaching conversation can help the leader examine their own judgment: what the uneasiness concerns, what they need to learn, and what terms they can responsibly accept.

I would first ask what would make the conversation useful. Does the leader want to examine the decision, prepare for a discussion, or understand why a particular option feels difficult? Agreeing on that purpose makes the time more likely to serve the person using it.

It also helps establish when a different kind of support is needed. A question requiring specialized advice should receive it. A decision that belongs to the board still belongs there. Coaching can help a leader prepare without taking over those responsibilities.

Leave room for the leader's own reasoning

A question can sound open while quietly directing someone toward the answer the questioner prefers. Experience makes that temptation especially easy. We recognize a pattern and want to save the person time.

I would rather check my understanding before treating a familiar pattern as the explanation. In the partnership example, I might ask:

• Which part of this agreement will be hardest for your team to honor?
• What would you need to learn before you could stand behind the decision?
• Where do your responsibilities to the organization and your concern about this partnership meet?
• What are you preparing to agree to that you have not discussed with the other party?

The answer will determine where the conversation goes. I might learn that the staffing concern is manageable, while the question about the partner's influence needs far more attention.

Allow time for that answer. Listen for what the leader considers important, rather than using the reply as a route into your own story. If you reflect an observation, check it: “I heard you return to the staffing commitment several times. How does that fit with what is concerning you?” The person should be able to correct your interpretation.

What the research can support

A 2023 review of 37 randomized controlled studies of workplace and executive coaching found a moderate average benefit across the leadership and personal outcomes studied. It also identified publication bias and larger effects in self-reported outcomes than observed outcomes. That is encouraging evidence for coaching as a form of support, with important limits. It does not establish that every coaching approach works equally well or that any particular conversation will improve an association's results.

Research on motivation at work also emphasizes the significance of autonomy, competence, and connection with others. My practical interpretation is to respect a leader's ability to choose, recognize the knowledge they already have, and offer a relationship in which they can examine their thinking.

I would judge an engagement against the purpose agreed with the leader. Did they understand the decision more fully? Identify missing information? Prepare a conversation they needed to have? Make a choice they can explain and review? Those are useful questions to revisit together.

If you manage the person, be honest about power

Association executives can use thoughtful questions and careful listening with staff. They also have authority over assignments, performance, and opportunities. That authority remains in the conversation.

If you have already decided on a deadline or requirement, state it plainly. Then invite discussion about how to meet it and what support is needed. Asking questions until an employee proposes your predetermined answer can make the exchange feel like a test.

When an association pays for outside coaching, agree at the outset on the purpose, what will remain private, and what information will be shared with the sponsor. An executive should know the terms before deciding what to discuss.

Pay particular attention when a staff member names a problem the organization has created. If their workload cannot fit into reasonable hours, they need a management decision about staffing, priorities, scope, or timing. A reflective question should not transfer that decision back to the person without authority to make it.

Make space for a decision that is still yours

For the partnership example, a useful outcome might be identifying the staffing assumptions that need verification, the terms the executive wants to renegotiate, and the information the board needs before approval. The leader remains responsible for judging those steps in their own context.

If you are facing a decision, begin by writing down what you know, what you are assuming, and what you have been reluctant to discuss. Bring that account to someone who can listen carefully and help you examine it.

I offer that support through Rest & Resolve. We can give a leadership question time and attention, while keeping the organization's responsibilities in view. You can begin with a conversation about what you need.

References

1. de Haan, E., & Nilsson, V. O. (2023). What can we know about the effectiveness of coaching? A meta-analysis based only on randomized controlled trials. Academy of Management Learning & Education, 22(4), 641-661. Read the source.
2. Deci, E. L., Olafsen, A. H., & Ryan, R. M. (2017). Self-Determination Theory in Work Organizations: The State of a Science. Annual Review of Organizational Psychology and Organizational Behavior, 4, 19-43. Read the source.

Training and reading background

• Kimsey-House, H., Kimsey-House, K., Sandahl, P., & Whitworth, L. (2018). Co-Active Coaching: The Proven Framework for Transformative Conversations at Work and in Life (4th ed.; especially chapters 2, 3, and 5). Nicholas Brealey Publishing. Publication details.