10 questions that will make you a better leader

I remember the first time feeling the power of a question. I was preparing for a new project, which had a lot of focus from various stakeholders in the organization. Each of them had – naturally – different, even conflicting views on the goals and key outcomes as well as the risks of the project. I needed some guidance before getting the team started, risking that they would work on something that was not needed while something crucial was completely forgotten.

What made the situation more complicated was that my direct manager had just left the organization and I had no other choice but to skip a level and go directly to the senior vice president for advice. I have prepared my questions and managed to reserve 10 whole minutes in his calendar.

The meeting started as usual. I quickly presented the situation.

“What shall I do?”- I asked, full of expectations to finally get some clear guidance.

“What would you recommend we do about this?”, he answered.

I was shocked. With some 8 years of experience in different jobs, I was used to the senior managers TELLING you what to do. Not only that but having very clear, sometimes extremely detailed opinions on what to do. Even getting upset if you deviate from their vision of what should be done – and how – by a millimeter.

But this time, I got a question. The senior vice president smiled, curiously looking at me, genuinely waiting for an answer. I composed myself and answered. To my own surprise, I did indeed have a very good idea of what we should do and could clearly explain why it is a good idea.

“Great! Then that’s what we do. Thank you for a productive meeting!”, said the SVP, apologized for having to leave for the next meeting, and walked out of the room.

It was a very productive meeting. Not only did I get a clear idea of how to define the project and present it to my team, but also felt empowered, motivated, and energized. Just ten minutes and one question to achieve that!

Soon after that, I became interested in coaching: the art of asking good questions. While it is, indeed, a form of art and requires a lot of experience and a close relationship with a coachee to ask the most effective questions, I believe that any leader can become better by asking questions instead of telling their team what to do. In fact, there is a myriad of benefits to doing so: according to the Harvard Business Review, „people with this skill are seen as more empathetic. They also lower the threshold for others to speak up, increase the quality of decisions, and foster collective intelligence.“

https://hbr.org/2022/05/the-art-of-asking-great-questions

You can start by trying the list of my favorite ones:

1. Can you tell me more?

This is a great question to demonstrate your curiosity and show respect for the person talking to you. Too often, people start assuming what you will say next. They hear the first few words and feel like they already know the context, your position, and what should be done. Not only it is a very biased and limited approach, it likely leads to worse outcomes. Additionally, it makes the conversation partner feel disrespected, not listened to and offended.

“Can you tell me more” is a very open question for any situation. It helps build a relationship, explore possibilities, and get more creative. Finally,  the person asking the question might learn something surprising. Absolutely a win-win, isn’t it?

2. What do you really want?

Many people have a very hard time telling what they want. They feel ashamed or scared of wanting something. Perhaps their wish is too simple, too materialistic, too ambitious, not ambitious enough… Getting a clear „no“ is so scary. Better to not even ask. Or is it? By not asking, one will surely not get what one wants.

This question legitimizes wanting, as it absolutely should be allowed. It does not guarantee all wishes will be granted, but surely brings a person one step closer. So many leaders do not give their employees what they want simply because those same employees do not tell them what they want. It could be that simple. Being invited to a meeting with important stakeholders, a super long vacation, getting on a project, getting off a project, going for that promotion… How can a leader know if you do not tell them clearly?

3. What is blocking you?

I really like this question because it is something that people often do not think about. They FEEL blocked, but are they blocked in reality? If so, can those blockers be removed easily? Sometimes, this question is enough to remove those barriers. If not, stating them clearly helps to create concrete approaches to navigating around them.

4. What is the worst that can happen?

This question might sound negative, but it is extremely powerful. The human brain is very good at overstating the dangers. Have you ever been anxious before a presentation? Nervous just thinking about a meeting with a specific stakeholder? Perhaps sweating just imagining the networking part before the workshop? Have you ever tried thinking, about what is the worst that can happen in these situations – and what you can do in those cases?

The answer is that these are not life-or-death situations. You might not become their idol, might need to smile and say your name and what you do. Does that really sound so bad? Of course, not – and that is exactly what this question helps to uncover.

5. What would (insert a relevant person) do in this situation?

As humans, we are extremely self-centered. When we experience strong feelings, it is hard to even think that different perspectives might exist. This question helps to get out of that.

The first time I experienced this question in action was in relation to the organizations, not people. It is a question often used by consultants, aiming to get the workshop participants out of their usual way of thinking. „How would Google solve this problem? What about Coca-cola?“ asks the facilitator. The workshop participants, which might be working for a pump producer or an energy conglomerate (important that it is distant enough to get creative juices flowing), get initially confused, but then start shooting answers, one more creative than another. Finally, they allowed themselves to get a bit playful and forget their typical jargon and abbreviations – those would not work for Google or Coca-cola anyway.

For persons, this question works very similarly. Can they think of what would a person they respect do in this situation? Could be anybody: a friend, an idol, a respected colleague, or a senior leader. What‘s important is not even the solution, but showing that different paths exist.

6. On a scale of 1-10, how motivated are you to do this?

Scale of 1-10 questions can be used in many different situations (not only about motivation). Their magic lies in the numeric expression of something that is typically perceived as soft and uncountable. To make their feeling precise, humans must first try to understand what they feel. Listen to the inside and explore.

Additionally, the number helps to understand reality. Generic answers, like “I am motivated” or “It goes well” could mean absolutely anything. Most often, they are a polite version of not telling anything. On the other hand, answering “My motivation is currently a 4 out of 10“ provides much more insight and opens the door for additional questions.

7. If you had all the needed resources, what would you do?

This is an explorative question, which removes (real or imagined) barriers and welcomes creativity.

People often do not allow even the tiniest mental exploration of a target state if they believe they will be blocked from it. „I will never get funding for this idea“, they think. „Our team will not have time to work on it“, they say to themselves.

Is it always true? I do not think so.

This – and other If…, what…? questions create a little playground for unrealistic ideas. Once played, many of them might become very realistic.

8. What will happen if you continue like this?

Feeling stuck is horrible. It is also a self-fulfilling prophecy: when you feel stuck, everything around you seems to make you even more grounded. Any other options seem unrealistic, scary, or worse than reality.

This question aims to show that being stuck is not a good choice. It is a bit like the reminder in the airplanes: „Nearest emergency exit might be behind you“. What will happen if you continue pushing for the door in front of you, but it is still far away and way too crowded? Think about it. Continuing the situation also has its price, sometimes way bigger than one expects. Once understood, changes might no longer seem so scary.

9. What will be the next step?

Have you ever attended a meeting, where really many things were discussed, but once it ended, nobody was really sure what to do? Of course, you have – most meetings are like that. Sadly.

It is an enormous waste of everyone‘s time and very costly for organizations.

Do you want to be the one breaking this cycle? Use this question to ensure at least one clearly defined action is agreed upon. It could be very small: to ask somebody for help, summarize the discussion, organize a follow-up, etc. What this question aims to do, is not necessary to DEFINE a concrete action, but to get participants‘ minds into thinking about actions. It might result in a question that one of the participants did not think – or dare – to ask, but now they did as otherwise, they cannot do the next step. It might force people to make a decision – perhaps they cannot „afford“ another action being put on the to-do list.

That are just a few examples. The possible outcomes are uncountable, but one thing is sure: this question reduces the time-wasting blabbering that many meetings are plagued with and gets people to do some real work.

10. What is it that I did not ask, but you think I should?

Asking good questions is not easy. That is why I define coaching as the art of asking good questions. Mastering that art is not easy. Even for the masters, sometimes one just lacks inspiration or insights.

This question helps to overcome it. It gives freedom for the coachee to add an additional perspective, the one that the person asking the questions did not even think about.

In my experience, this question is a bit like poking in the dark. Most often, the conversation partner will not answer anything. However, when they do – it is pure magic, truly unexplored territories, and an enormous learning opportunity.