Introduction
Early in my leadership career, I would engage with employees who made a poor choice or failed to meet a deadline in a rather authoritative manner. I usually opened with questions like “Why did you do that?” or “Why is this not completed on time?” Those questions immediately put people on the defense and rarely led to good outcomes.
One specific example stands out. I once asked a teacher why I saw her driving away from the building before the day was complete. She told me she had a meeting across town, which I then called and verified. She was offended that I would “check up on her” rather than simply trusting her word. My choice to stop after that first question created damage to our relationship. Had I simply asked another question or two—about her day, about what she was heading to—I would have built clarity instead of distrust.
That moment taught me an important leadership lesson: asking the extra questions is critical. It not only clarifies what’s really happening, but also shows employees you care enough to understand before you judge.
The Problem with Stopping at the First Question
Most leaders fall into the trap of asking just one question: “Why did this happen?” or “What went wrong?” These questions may feel natural, but they often invite defensiveness instead of dialogue. When we stop there, we risk walking away with assumptions rather than understanding. Worse, we may damage relationships by signaling we don’t trust or respect our people.
The Power of the Extra Questions
The extra questions open doors. They move the conversation from confrontation to curiosity, from accusation to understanding. They help uncover whether the challenge is about will, skill, clarity, or something external that is impacting performance. Most importantly, they show your employees that you value them enough to truly listen.
Categories of Extra Questions Leaders Can Ask
- Clarify Context
- “Can you walk me through what led up to this?”
- “What factors influenced your decision here?”
- Explore Resources & Support
- “What resources or tools were available to you?”
- “What support might have helped in this situation?”
- Dig Into Process
- “How did you decide on this approach?”
- “Where in the process did you feel stuck or challenged?”
- Uncover Barriers
- “What obstacles got in the way?”
- “What turned out to be harder than expected?”
- Connect Back to Expectations
- “How do you understand the expectation in this situation?”
- “What does meeting the expectation look like to you?”
- Look Forward, Not Just Back
- “What’s one adjustment you could make next time?”
- “What support from me would help you succeed moving forward?”
Benefits of Asking the Extra Questions
When leaders lean into the extra questions, three things happen:
- Trust grows. Employees feel respected and valued rather than judged.
- Clarity emerges. Leaders discover whether the issue is a misunderstanding, a resource gap, or something else entirely.
- Solutions surface. By exploring barriers and processes, leaders and employees can work together to prevent repeat issues.
The real power is in shifting the conversation from “what went wrong” to “what can we learn and how do we move forward?”
Conclusion
Leadership isn’t about catching people in mistakes—it’s about helping them succeed. That requires curiosity, patience, and a willingness to ask one more question than feels natural.
The next time you’re tempted to stop at the first question, pause. Ask the extra questions. You may be surprised by what you uncover—and by how much stronger your relationships become when you choose curiosity over judgment.
If you or your team are wrestling with how to have these kinds of conversations, I’d love to help. This is the work I do every day with leaders and leadership teams—creating clarity, strengthening trust, and developing the confidence to handle tough situations with grace and purpose. If you’d like to explore this further, let’s connect for a conversation, or consider bringing me in to work alongside your team. Together, we can build the habits of asking the extra questions that lead to stronger culture and better outcomes.