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    The 1 Question I Ask in Every Leadership Meeting

    wildgreenquest@gmail.comBy wildgreenquest@gmail.comOctober 20, 2026006 Mins Read
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    Opinions expressed by Entrepreneur contributors are their own.

    Key Takeaways

    • Green dashboards don’t necessarily reflect reality. Ask, “What am I missing?” to uncover hidden risks, flawed assumptions and obstacles before they derail a project.
    • Encourage team members to explain risks and propose solutions. Creating a culture where people feel safe raising concerns early builds trust and accountability.
    • End meetings with action. Every concern should lead to a clear decision, an assigned owner and specific next steps. That discipline turns discussion into execution.

    Every executive has sat through the familiar project review. A dashboard flashes green, yellow and red. Leaders move from one initiative to the next, assuming the colors tell the story. They don’t.

    I remember sitting in a leadership meeting reviewing a major project. The status was green. The completion percentage was 20%. The deadline was the next day.

    I said, “Walk me through how we’re going to finish the remaining 80% by tomorrow.”

    The response caught me completely off guard.

    “We’re not late yet.”

    Technically, that was true. The deadline hadn’t passed. Operationally, it was disconnected from reality.

    That meeting reinforced something I’ve seen throughout my career. Leaders can become so focused on reporting status that they lose sight of what is actually happening. Green, yellow and red tell you almost nothing by themselves. A project can appear healthy while serious risks are quietly building beneath the surface. Teams can update every dashboard and complete every status report while moving steadily toward a missed commitment.

    People confuse process with progress.

    From that point on, I changed how I ran leadership meetings. Instead of asking people to explain the dashboard, I started asking one question: “What am I missing?”

    That question has consistently improved the quality of decisions, strengthened accountability and helped teams execute more effectively because it uncovers information a status report never will. The real value, however, comes from what happens after full transparency is provided.

    Step 1: Surface reality

    When I ask, “What am I missing?” I’m not asking for opinions. I’m asking for information. I want to know what risks haven’t surfaced, what assumptions we’re making, what dependencies could derail the timeline and what decisions are preventing progress.

    If your meetings consist of everyone reporting that everything is on track, you’re probably missing something important. When you think about it, what does a green status tell you about what’s really going on? Instead, ask questions that reveal what’s actually happening.

    • What risk are we not discussing?
    • What assumption could prove wrong?
    • What decisions need to be made today?
    • Where do you need my help?

    Those questions move the conversation beyond reporting and into problem-solving.

    Step 2: Clarify the risk

    Finding a risk is only the beginning. When someone raises a concern, don’t move on to the next agenda item. Ask them to walk you through it.

    What evidence supports your concern? What happens if we do nothing? What options do we have?

    This is exactly what happened during that project review. Once we walked through the work that remained, everyone could clearly see the project wasn’t green at all. We still had time to respond because we identified the problem before the deadline arrived.

    Leaders don’t create value by discovering problems. They create value by discovering them while options still exist. Time is a precious resource; get to the heart of your issues early, and you will have more room to work out a solution or do damage control.

    Step 3: Turn concerns into ownership

    One of the biggest mistakes leaders make is allowing someone to identify a problem without asking them to help solve it. Whenever someone raises an issue, I follow with another question.

    “How would you approach it?”

    That shifts the discussion immediately. Instead of simply pointing out what’s wrong, people begin thinking through priorities, tradeoffs, resources and execution. They become invested in the outcome because they’ve contributed to the solution. Ownership grows when people articulate their thinking and help shape the path forward. Ownership is a way to reward people for providing transparency.

    Step 4: End with action

    Every concern raised in a meeting should end with a decision or an owner. If additional resources are required, decide who will secure them. If priorities need to change, make the tradeoff before the next meeting. If an issue needs to be escalated, assign someone to do it.

    Meetings should never end with everyone agreeing there is a problem. They should end with clarity about who is doing what next. That discipline turns discussion into execution.

    Transparency creates trust

    This process only works if people believe it’s safe to speak honestly. Too many organizations unintentionally reward good news, and that can have unintended negative consequences. People learn to protect themselves by reporting green until the evidence becomes impossible to ignore.

    I reward something different. I reward transparency. Silence can be deadly, never mind expensive.

    When someone surfaces a risk early, my first question isn’t, “Who caused this?” It’s, “What decision do we need to make now?” That response teaches the organization that identifying problems early is valued because it gives us time to solve them. Over time, people stop hiding issues and start bringing them forward while options still exist. That is how trust accelerates execution.

    Better questions create better leaders

    Leadership today is very different from when I started my career. Technology evolves rapidly. AI is changing how organizations operate. The pace of business continues to accelerate, and no leader has all the answers.

    The leaders who succeed are the ones who consistently uncover the information they don’t have. At the beginning of your next leadership meeting, try this simple process. Ask, “What am I missing?” Listen carefully before offering your own conclusions. Turn concerns into ownership by asking how people would solve the problem. Leave the meeting with clear decisions, clear owners and clear next steps.

    Better leadership rarely begins with having the smartest answer. It begins with asking the question that unlocks clarity, better judgment and stronger decisions.

    Key Takeaways

    • Green dashboards don’t necessarily reflect reality. Ask, “What am I missing?” to uncover hidden risks, flawed assumptions and obstacles before they derail a project.
    • Encourage team members to explain risks and propose solutions. Creating a culture where people feel safe raising concerns early builds trust and accountability.
    • End meetings with action. Every concern should lead to a clear decision, an assigned owner and specific next steps. That discipline turns discussion into execution.

    Every executive has sat through the familiar project review. A dashboard flashes green, yellow and red. Leaders move from one initiative to the next, assuming the colors tell the story. They don’t.

    I remember sitting in a leadership meeting reviewing a major project. The status was green. The completion percentage was 20%. The deadline was the next day.

    I said, “Walk me through how we’re going to finish the remaining 80% by tomorrow.”



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