What Keeps You Awake at Night as a Leader? Three Questions That Create Clarity

By Jerome Hopkins, CHA | Founder & CEO, Victor Cannon Leadership

The workday ends, but the leadership questions keep going.

A conversation you have delayed. A team member whose performance is slipping. A customer problem that keeps returning. A decision that affects people who depend on you.

You replay the situation, consider another possibility, and promise yourself you will deal with it tomorrow. Yet tomorrow arrives with more demands, and the same concern remains.

You may not need another hour of thinking about the problem. You may need a clearer way to decide what deserves your attention and what you will do next.

Start with three questions: What is actually happening? What is mine to lead? What action have I been avoiding?

1. What is actually happening?

Pressure can turn one difficult event into a broad conclusion.

“The team does not care.”

“Nothing is working.”

“I have to handle everything myself.”

Those statements express frustration, but they do not tell you where to act.

Describe what you can observe. What happened? When? What expectation was missed? What was the effect? What information is still missing?

Consider an illustrative hotel situation. A GM notices that promised guest callbacks have been missed on three evening shifts. The first conclusion is that the evening team lacks commitment.

A closer look reveals that callback requests are recorded in two places, the handoff does not identify an owner, and the supervisor has not been checking unresolved requests.

That does not excuse a missed promise. It identifies what the leader needs to investigate and address.

Write one sentence that separates the facts from your interpretation:

“On three evening shifts this week, promised guest callbacks were not completed, and we have not confirmed who owned each follow-up.”

Now you have a problem you can discuss, rather than a judgment you must defend.

2. What is mine to lead?

Responsibility does not require you to personally complete every task. It requires you to recognize where your leadership is needed.

In the callback example, the GM may need to clarify the service standard, settle the handoff process, give the supervisor appropriate authority, and establish a review point. The supervisor and team members still have work they must own.

Ask yourself:

• What decision requires my authority?
• What expectation have I left unclear?
• What support or resource must I provide?
• What responsibility belongs to someone else?

Be specific about the boundary. “I will lead the reset of our callback process. The evening supervisor will coordinate completion and escalate unresolved requests.”

You also need to recognize what you cannot decide alone. An owner’s approval, another department’s resources, or a contractual commitment may require escalation. Name the person who can act and the information they need.

Clarity grows when you stop treating every concern as a task you must carry yourself.

3. What action have I been avoiding?

Sometimes the next step is already clear. You have been postponing it because it feels uncomfortable.

Perhaps you need to address repeated missed commitments. Perhaps you promised support and have not delivered it. Perhaps a plan needs to change, and you are reluctant to acknowledge that.

Ask: “What conversation, decision, or request would move this forward?”

For the hotel GM, that might mean meeting with the evening supervisor, reviewing the missed callbacks, hearing the supervisor’s perspective, and agreeing on one process for assigning and tracking follow-up.

Prepare the conversation around the expectation and evidence. State what needs to change. Listen before deciding whether the issue is understanding, resources, capability, or behavior.

Choose an action you can reasonably begin within 24 hours. If you need more information, your first action may be requesting it. A responsible decision can take time; beginning the work does not have to wait indefinitely.

Your 24-hour leadership commitment

Before you close your workday, complete these five lines:

For example: “Tomorrow at 10:00 AM, I will review the callback handoff with the evening supervisor. We will agree on ownership and escalation. On Friday, we will check whether promised callbacks were completed and identify any remaining gaps.”

This is a tool for organizing a leadership concern, not a promise that every difficult situation will disappear overnight.

The purpose is to move from repeatedly carrying the concern to deliberately leading the next step.

Leadership growth becomes visible in what happens after the reflection. Think with greater clarity. Lead with greater intention. Execute with greater discipline. Review the result and adjust.

If you prefer to plan on paper, use the Victor Cannon Leadership “Write It. Own It. Do It.” Journal to record your answers, your next action, and your follow-up date. Return to that entry after you act and note what changed.

Take the next step

For a practical introduction to the Victor Cannon approach to leadership, mindset, execution, and service excellence, get the complimentary Victor Cannon Leadership Playbook™.

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