Generally, leaders are supposed to be the ones who know the answers. But we all know that leadership involves as many questions as answers.

Asking the right questions helps keep your thought process fresh and opens you up to new ideas.

Knowing which questions to ask when can improve our leadership qualities. Good questions are ones that help provide direction, increase knowledge, promote engagement, and help with decision-making. Here are seven questions that leaders need to regularly ask themselves and answer with total honesty.

1. What’s the best thing I could do in the next 10 minutes?

Time management and prioritization are two important leadership qualities. This question gets at both these issues. Perhaps the thing you need to do most is “eat the frog” by doing something you dislike so you can have it off your plate. Or perhaps you need to make a list of things you need to do so you can put them in priority order. Either way, you’re preparing yourself for effective action.

2. How can I bring clarity to this situation?

When teams struggle (or even if they’re just having an “off” day), it can help to reframe the vision for what needs to get done. Adding clarity when people are struggling forces you to take stock, defining immediate goals and timeframes, and ensure people have the resources they need. Sometimes turning a difficult day for your team around can be done by bringing clarity to the situation.

3. What would a great leader do in this situation?

If you have a “hero” leader that you have always looked up to, why not ask yourself what they would do in your situation? Not only can this give you courage and inspiration, it can put your situation into perspective. For example, asking how Augustus would handle the changeover to new accounting software can remind you that you’re not conquering Egypt and Dalmatia, but handling something that every business must cope with.

4. How did I enable or hold back my team today?

While there is little to be gained from replaying conversations repeatedly in your mind, there is much to be gained from reviewing the day and being honest about ways you could have done more to facilitate your team’s performance. Or maybe you said something that had unintended negative consequences. Unpacking that and understanding why it happened can help you avoid similar blunders in the future.

We all should review our performance and learn from both successes and mistakes.

5. Who is challenging my way of thinking?

It’s not healthy to be surrounded by “yes-men.” In fact, the best leaders surround themselves with people who aren’t afraid to challenge them. You don’t want to create a corporate culture where people are afraid of challenging their leaders when they feel strongly about something. Who are these people? Are they getting under our skin, and if so, why? What might be gained from trying to see things from their perspective?

6. Who haven’t I met with recently?

If your team is carrying on effectively, it’s easy to assume that someone you haven’t talked to in a while is simply working well on their own. That may be the case. Then again, if you haven’t had face time with someone for a while, it’s a good idea to reach out. Just as the geraniums in your planters may appear to be thriving while actually being choked out by an invasive vine, the dependable team member may be dealing with something where you could help. And you won’t know unless you ask.

7. What do I need to work on?

It’s nice being comfortable as a leader. But comfort may indicate that we need to stretch a little. We need to regularly remind ourselves of new opportunities, new responsibilities, or simply of skills we need to work on. There’s truth in the old joke that says, “If you’re resting on your laurels, you’re wearing them in the wrong place.” The world is changing, and the methods and skills that got you to where you are won’t necessarily equip you for future success. Make continual learning one of your top goals.

Leadership coaching often involves helping clients learn to ask the right questions of themselves and answer them honestly. Doing so can help you lead effectively day-to-day and over the long term. If you’re interested in learning more, I invite you to check out my books. 


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