One of the most important skills of a leader is the ability to ask great questions. While some people’s leadership style is better characterized by an exclamation mark (“Look at me!” or “Do this!”), the greatest influencers shape their leadership around the question mark – they know what to ask and when to ask it.

The Power of a Great Question

You know the power of a great question. Have you ever made a major shift in the direction of your life after asking yourself, “Why am I doing this?” Have you ever been brought to tears by someone, either a friend or even a stranger, who asked at just the right moment, “How are you doing?” One question is so important it often comes with a diamond ring (“Will you marry me?”). Questions have been the catalyst for changing vision statements of entire companies, created new and ingenious inventions, and propelled scientific advances. They have enormous power.

Why is it, then, that most of our discussions as teams at work or families at home are less than inspiring? Question and answer times are often something we begrudgingly do and endure instead of anticipate with excitement. In the process, we wind up missing out on a powerful opportunity to connect and dream with those around us.

How to Ask Better Questions

What separates great questions from poor or boring ones? I write discussion guides as part of my job – I love thinking through what makes or breaks a question. And so, as I think through potential questions to ask my team at work or even for a discussion with my spouse or another friend, I run them through these seven filters. In a sense, these are questions for my questions.

1. Can the question be answered with a “yes” or “no?” If so, it’s probably too simplistic. Great questions stimulate conversation; questions that require only one-word answers or a simple affirmation typically stifle conversation – it only wants a quick conclusion, not a great discussion.

2. Is the answer to the question super obvious? I call these, “Well, duh,” questions. For example, in the church, there’s a joke that if you get called on by a Sunday School teacher when you weren’t listening, just say the answer is Jesus. You’d have a pretty great chance at being correct! Often this type of question is asked to make sure people have a basic comprehension of the material. That’s not a bad goal. But, when the answer is already known by most everyone, people will check out fast. Consider other ways to check comprehension, like, “What one thing surprised you in that talk,” or “Did anything bother you in this chapter?”

3. If the question is personal in nature, am I willing to answer first? Questions like, “What’s your greatest weakness,” or “What did you learn from a recent failure,” have a lot of potential for a powerful conversation. But, when vulnerability is involved, someone needs to go first, and that is a risky step. If you are leading a discussion and you include a deeply personal question, it’s your job to set the example and open up first. If you’re not willing to do it, you can’t expect others will either.

4. Am I only asking “serious” questions? Let’s be honest – some of us aren’t a lot of fun. That’s okay; we still love you, and if we were in a group project with you, we probably did well because of all the work you did… so thank you! But, if you are more of a no-nonsense leader, you probably downplay the necessity of inserting fun questions. But, questions that seem, on the surface, silly are actually quite important. Some of the best conversations start with a simple game or random question. For example, one time I started a team meeting by putting out a bunch of drinks I got from a convenience store. I asked everyone to pick a drink that best represented their week. It had nothing to do with our current initiatives or deadlines, but it produced one of our best, most bonding conversations. These questions help build cohesion and loosen things up a bit, so don’t skip them!

5. Did I plan ahead? We often think a great conversation just happens, but that’s hardly ever the case. The best facilitators spend a significant amount of time crafting the discussion ahead of time. They thought about their audience: who they were asking the questions to and what would best connect with them. Would you ask a teenager the same question you would ask a toddler? They also think about the destination: where are we headed? Without preparation, a conversation can lose purpose real quick.

6. What would be a potential follow-up question? Even though you should have a plan, we need to be willing to deviate from it if someone shares something significant. Some of the most memorable questions I’ve been asked weren’t the first question; they were the follow-up questions, like, “Why did you think that?” or “Can you tell me more about that feeling?” These type of questions show someone is actually listening and not just plowing through an agenda.

7. Am I okay with silence? For most of us, the answer is no. Which means if we ask a question and more than five seconds pass by, we tend to move on to the next one. However, if it’s a truly great, thought-provoking question, it will take people time to think and answer. Leadership is not always about talking and asking; it’s more often displayed in waiting and listening. So, ask a question, put a smile on your face, look at different people in the circle, and calmly say, “I’ve got all day and silence is just fine with me.”

The world could use more leaders who are in the business of asking questions first and making statements second. Leading great conversations is an art form worth developing. A question has the power to penetrate the soul, change the status quo, and invite others to join us in discovering truth. So, let’s ask those type of questions with those around us.

As you think about the time you spend with your co-workers, significant other, children, and kids, what questions do you need to ask – question that would connect you in a deeper, more powerful way?