Early in my career, in my mid-twenties, I had already the privilege of working with Executive Board Members of my company. I was a project lead for an IT implementation project. It was about an analytics system and as it was also about providing new analytical capabilities to the Executive Board, there were also board members taking part in my steering committee meetings. As our company got a new CFO, I gave him an introduction about the background of the project and the deliverables planned. So far so good. One day, as I walked by his office, he called me in and asked some questions. He asked me about how I’m doing, about my opinion of several things across the company, the IT organization as well as what he has planned to do in finance and what I would think of it. As a leader, he engaged me in his thinking process. It impressed me a lot, how open he was at that time and how curious and interested he listened to me and my opinion. I believe that this talk also inspired me a lot on my journey to become an executive leader afterwards. At that time, this Senior Executive already showed a fresh style of an open and trustful leadership. He was not anymore standing for a conservative, traditional leader who command and control, direct, and tell. He was an empathic, open, curious leader, who understood the power of direct engagement across hierarchies.

Nowadays, if a Senior Executive stands only for command and control, he or she is missing the point – and even more, he or she is missing the biggest opportunity to help his team to grow and advance their skills. Instead, asking great questions is exactly the ingredient to foster a culture of learning and with that the most powerful development measure a leader has. For me, asking great questions is THE superpower, every leader should master.

“It is better to know some of the questions than all of the answers.”
James Thurber

Yes, for sure, we as leaders are asked to set the vision and strategy and provide the direction. But the best leaders know, that to be successful, you must do one thing extraordinary well: asking great questions. This is where the magic of successful leadership happens.

The best leaders don’t sink in monologues, they encourage conversation and dialogue. They understood the superpower of asking questions over than always providing the answers. And furthermore, asking questions helps others to follow their thinking. As we open the space for a dialogue by thought-invoking questions, everyone has the time to think through and develop better decisions or approaches. Obviously, it doesn’t stop there with asking the question, we as leaders also need to be ready to pause and then listen. Which also sounds sometimes easier than it is.

So, while any answer is only as good as the question asked, leaders need to master to ask not only good but great questions. Not everyone is by nature good in it or knows how to ask great questions. It’s like many other things a craft which requires time and effort to learn and to perfect. And it requires a lot of courage and sometimes tact, to ask not only great but tough questions without lighting defensiveness. Let’s have a look how to master this superpower of asking great questions.

What makes a great question?

First, there are no bad questions – bad or wrong questions don’t exist. However, some questions are better in line of the context or moment, hence they are much more powerful. This also means, there is not that most powerful question of all, but again, only just the right and greatest question for the moment. It is the one which is spot-on, and which is right for the person being addressed. And most importantly it is the question which unlocks the door towards more information, greater insights and better decisions and answers.

Good questions are concise, they are clarifying deadlines or uncovering who is doing what, they are getting right to the point, and they are necessary to avoid confusion. But a great question returns even more information. If you want to be an outstanding leader, you need to ask those great intelligent questions more often than simply good questions.

To understand what makes a great question, let’s look on the main categories of questions you can ask and what ability they have in a conversation: 

• Open questions – If you ask Open-ended questions, you are extending the conversation for more information and explanation. This then also can help to stimulate out-of-the-box and alternative ways of thinking about the topic of the dialogue. And as a great leader, you also look for the greatness in others. So, with open questions you can foster that joint brainstorming to leverage the intelligence of all participants in the conversation. This is how best ideas appear, when we use our intelligence jointly to explore an issue and things that neither anticipated. By combining the open question practice with the funnel questions technique, you can question-by-question deepening the topic and narrow the scope of the discussion. Hence, use open questions primarily to strengthen engagement, scoping innovation and to bring new ideas to the table (when things or solutions are not yet fixed).
• Probing Questions – In order to assess assumptions and to avoid making decisions on faulty premises or incomplete understandings, you should probe what you have heard. Dig into the topic and ask why… or what if…. This is to draw out the person’s knowledge but also to foster personal growth as it leads others to a more accurate view of what they have talked about. It also can expand you conversation in new directions as well. Use probing questions to help people to open and reflect, to promote critical thinking and to dig deeper into the topic.
• Clarifying questions – Once you are not sure that you fully got the point, when something is unclear or hard to understand, please ask a clarifying question. Ask to avoid any confusion or misunderstanding, but not to challenge or probe. In such a situation you should avoid pushing someone into a specific question, but you should understand the topic better. This type of questions is primarily meant for yourself. Use clarifying questions to eliminate or prevent any mistake, confusion, or ambiguity.

All these types of questions do have the potential of being a great question to ask, if you are able to combine them with your own knowledge and experience so that you are asking them in the right moment, tone and to the right people. And while you should use primarily these three types of questions, this also means you should minimize the usage of closed, rhetorical, or leading questions as suggestive way of a conversation. They either will not bring the topic forward or such in case of the leading question prompts a respondent towards an already-determined answer.

What makes you a great questioner?

While you now know the three preferred types of questions to ask, let’s have a look on what is required on top to make you a great questioner.

It starts with simply making questioning a part of your daily practice as it is a skill that takes time and practice. In addition, the following characteristics should be on top of your mind as well to make you a great questioner.

• Be curious – A good questioner is curious above all. Be interested in the topics and in your dialogue partner. You need to know what information is needed and who is the best person to talk to. You need to think two steps ahead as well as you might need to use the proper tone and adjust your style flexibly.
• Be prepared – In order to think two steps ahead, you need to prepare yourself and keep your knowledge up to date. Do your research to fully understand what you are asking or what you are confused about. If you are expecting an intense discussion, better have your facts together well ahead of time to reflect on it.
• Be purposeful – Always have the purpose of the dialogue in mind and choose your words and timing wisely. A leader never jokes at the expense of others and irony, sarcasm and cynicism are out of place.
• Be courageous – Sometimes it is also required to be the most courageous person in the room by speaking out things no one will hear. But bear in mind, if your question is to fluffy or confusing, you won’t add to the discussion, nor you will get the type of answer you need. So go beyond the surface-level if you think it is needed.

Finally, please have in mind that keeping questions short still by providing sufficient details is always your goal. Not the question should take most of the time in a dialogue, but the answers. In combination, it is also ok to pause to listen and think between answers as it gives you the needed time to reflect about what was said. Hence, get comfortable with silence and always use silence to your advantage.

What is the result of a leadership-worthy question?

Consequently, intelligent, skillful questioning is a superpower, which leads a dialogue to a clearer, better result. By creating a foundation of mutual understanding, great questions are the direct accelerator for decision-making. And over time, it guides your employees away from being dependent on your answers. You can strengthen their ability to gain the benefit of their knowledge right away as they will train to think through the topic before they finally bring it to your attention. They will know that you are not the one who will supply all the answers but the one who is asking even more questions. And by that, asking smart great questions is one of the most effective ways to lead your team. Your team will understand better what you are thinking and what you are heading for.

However again, leadership-worthy questions are always a combination of thoughtful communication and tactful timing. The best order and sorting of your questions within a conversation depends on the circumstances. Even if you must start with a tough question in tense situations, it might can help to get your dialogue partner out of their shell. But for sure it requires the finesse to identify if it is appropriate and helpful to do so. But the good news is that when we ask questions, we automatically increase our emotional intelligence, which in turn leads to us becoming better questioners. Trust in yourself as a seasoned leader, that your personal style and your experience will help you to find the right and best time and technique to question your people. Still, the art of questioning is a practice which needs to be build up. But the result is a more human, better culture as well as a more successful business. Asking questions is a unique, incredibly powerful means of releasing values in companies: It promotes knowledge growth and the exchange of ideas, stimulates innovation and motivation, has a performance-enhancing effect, and helps to build relationships and trust in the team. It can mitigate business risk by uncovering unforeseen pitfalls and obstacles.

And with all above, you now also know the importance of listening. Asking but then ignoring or not listening is the worst what can happen. Only exchange and real dialogue lead to a powerful engagement and benefits both parties. So be not only a great questioner but an evenly great listener.

My personal reminders for pertinent questions

When I started to dig deeper into the art of questioning, I found 10 reminders for myself that helped me to master the superpower of asking great questions. Let me share them with you as they could help you, too.

1. There are no dumb questions.
2. It’s not about you! Show genuine interest in the answers.
3. Ask about things you don’t know the answer to already.
4. Don’t ask either/or questions.
5. Do not advice disguise as a question.
6. Don’t over explain your question, just get to the point.
7. Genuinely listen to and care about their answer (even if you initially disagree).
8. Appreciate the answer you are receiving, without directly interfering with your own opinion.
9. Pause after your counterpart’s response. Learn to endure silence.
10. If you think the questioner could answer the question by himself, return it back to him. 

And finally, start within your meeting culture: move towards not only providing an agenda upfront of a meeting, but also with naming the three critical questions that you need to answer during that meeting. At the end of those meetings, go back and check if you were able to answer them.

The only bad question is the one you didn’t ask.

To brush up your organization and teams to manage even greater business in future, you need to quit giving answers and focus on asking better question to unlock new opportunities. It also helps you to create a vibrant dialogue where anyone can learn. Great questions challenge your thinking, reframing the problem, analyzing the situation and helps building leadership skills among the team.

But the importance is not only for those who you are leading – remember, if you come home from a working day and you didn’t ask questions, you were not able to learn something new either. If you do all the talking all day long, you will not grow but stand still.

Let me know your thoughts. Would you agree to see Questioning as the Superpower for Executives? What was the greatest questions you heard and why? And finally, what would be your best tips to master the superpower of questioning. Eager to hear and read your thoughts.

“Look for people who have lots of great questions.
Smart people are the ones who ask the most thoughtful questions, as opposed to thinking they have all the answers.
Great questions are a much better indicator of future success than great answers.”

Ray Dalio