Great Leaders Ask Great Questions

Guest Post by Phil Owens

Originally Posted @

Too often we look to leaders and managers to ‘tell’ the staff what to do, or how to do it. This is a habit of management and leadership left over from the ‘command and control’ model of management that we left behind last century. It assumes that all of the knowledge resides in the leader or manager, and ignores what the staff member knows. It also fails to account for the collaborative potential of what may be discovered or created during a quality conversation.

If we believe that individuals can bring motivation, intellect, experience and innovation to the business, then rather than simply ‘telling’ them what to do we may engage them in appropriate conversations on the topic. This allows the leader to realise the inherent potential of the person or people they are leading, and enhance overall performance. The best way to encourage such quality conversations is for the leader to become expert at asking quality questions.

Questions help us understand and explore a situation, as well as challenge and expand it. Whilst we can simply ‘tell’ someone to perform a task, this does not guarantee that they have the motivation, the skill or the infrastructure to make it happen. It does not allow us to explore if there is a better way to do it, or what needs to be changed or added so that what needs to be done can be completed as effectively and efficiently as possible.

It is here that great questions allow these elements to be unlocked or defined to help us draw the potential out of those we lead, ensure tasks can be done, and open the way for innovation to emerge. As a leader, we can help those we lead to understand their thinking frames and thinking processes, as well as to expand what they know and create space for them to imagine new possibilities.

By asking rather than telling, we invite the other person to bring their subjective experience and beliefs into the discussion in a valuable way. We use their current beliefs and knowledge as he starting point. Telling, on the other hand, neither adds to their knowledge or beliefs, or helps a person make different meaning of what they already know. In this way, leadership is all about the quality of questions that we choose to ask.

Being a great leader starts with asking great questions which allow us to understand someone’s subjective experience. From there we can add our opinion and objectively derived facts. We can then work to get a specific agreement in terms of a shared understanding. From this point we can work to either deepen their understanding, or expand their thinking, depending upon their circumstance. The process of ASK-ADD-AGREE is a critical one for leaders to adopt to influence change. If we do not ask, we never find out their subjective experience. If we do not add, we do nothing to help them shift to some new understanding. If we do not then get agreement, we have no shared understanding of the ‘new’ position from which we can work forwards.

This process is only possible if we ASK first – Put simply, great leaders ask great questions to drive high performance.

What is a great question?

A great question advances the conversation; expands options, understanding and possibilities; and resolves issues. It is used as a way to open a topic, rather than close it.

A great question demonstrates parsimony. It is the simplest that it can be to get the result it seeks. Making a question complex, leading or double barreled (who likes to answer two questions at once, do you know anyone?) can make it difficult for the person to answer clearly and concisely. A great question is set up so it is easy to answer.

Great questions are effective. They ask what needs to be asked to deepen or expand the conversation. Ineffective questions either cover old ground, or invite tangential thinking which does not add value to the conversation or move it to where it needs to go.

Great questions are tactful. This means that the questions can be heard and understood. They are phrased so that they match with the thinking and communication style of the person being asked, taking note of their language and incorporating their subjective experience. This means the person needs less effort to access the information or experience, and removes the potential for misunderstanding or defensiveness which can occur when non-tactful questions are asked.

If we genuinely are interested in what the person will answer, and we approach the person curiosity and empathy, then we create the space for great questions to be asked. When we think we already know the answer, or really don’t want to hear the person’s opinion, then this becomes obvious to the person being asked the question. This facilitates defensiveness rather than openness. Asking great questions involves creating compassionate, empathetic space for the answers to be given.

When do questions not work?

Poor questions close off options, limit thinking, create defensiveness and get people stuck.

Often we refer to these as ‘closed’ questions that have a specific response set (such as yes/no) rather than unspecified response set (no defined answer set).

However, we also can ask questions which appear open, but due to social conventions, provide a limited or closed set of responses. These do not encourage the conversation to progress, but rather to act as ‘verbal wallpaper’.

A classic example is when one partner comes home from work. The question “How was your day, dear?” often has a formulaic response. Depending upon the context, the routine answer might be ‘fine’, or ‘lousy as usual’. Once the person has responded to the question according to the ritual, the topic is closed off. In this way, questions that appear open are actually ‘closed’ as they are asked to only draw a socially context-dependent closed response.

The way to counter these social questions is to be more specific. Ask “What was something good that happened at work today?” – the response makes the person reflect on their experience and share something which can start or progress the conversation. Therefore, before you ask a question it is useful to consider if there are a series of social conventions relating to that topic or question which render it ‘closed’.

Specific questions are also useful when people present global problems (such as always, never, should, etc). By asking where/when/how/who specifically, we can uncover the issue or circumstance that needs to actually be addressed.

When we ask questions which are injunctions (‘why did you do X’) it leads to defensiveness. For example, many people ask questions when they really want to tell you what to do. When your partner asks “Why didn’t you put the bins out”, they rarely want to understand the motivation behind your inaction, but rather the message is “Put the bins out!” Injunction questions – virtually any question with ‘Why’ – leads only to justification and often defensiveness, which only works to make people feel defensive, pressured or manipulated, which destroys quality outcomes. However, in such circumstances, we can either make a suggestion or directive (“Could you please put the bins out?”) or ask the question in a way to leverage the information that we want.

When we keep asking the same thing but hope for a different answer, we are asking a bad question. It is critical that we listen to the answer that a person gives, and work out what follow up question is required to add value and move the conversation forward. If you just keep asking the same question and expect a different answer, then both you and the person answering the question will both be disappointed.

Types of questions and their application:

We can use questions in two specific ways; to explore the knowledge or circumstance; and to expand the possibilities of what is known or believed.

If we imagine the person’s knowledge, beliefs and subjective experience was a closed frame, the first way to use questions allows us to understand the frame and what is within it. These questions include:

  • Determining current knowledge or beliefs (always a critical first step).
  • Defining boundaries, including exceptions to what we believe is true.
  • Determining processes that people follow.
  • Establishing categorization and sub-categorization of current knowledge or beliefs.
  • Defining meaning of the information or beliefs that are already held.

The second use of questions seeks to expand the frame. This creates possibilities. It takes what we think we know about what we know, and opens up the space for more expansive thinking, so that we add to, remove or modify knowledge and beliefs. These methods include:

  • Questioning the current boundaries of knowledge or beliefs, in particular exploring connections and additional elements which can be included.
  • Testing the content, particularly for accuracy or relevance.
  • Exploring categorizations and distinctions of what is known or believed
  • Reframing the meaning given to what is known or believed.

These questions all force the person to stop being stuck in their current thoughts, and start thinking. By encouraging a transderivative search, the person has to explore outside the current structure of their knowledge, connect ideas in different ways and create new meanings for knowledge they already have.

These processes relies on us, as questioner, to recognize that knowledge and beliefs are subjective, and that by asking great questions from a place of curiosity and empathy, we help shift the person answering from their current thoughts to new ways of thinking. This can be through a greater understanding of their knowledge and beliefs, or through changing and expanding their thoughts and beliefs.

This can be summarized as starting with people’s current knowledge and beliefs, and then either drilling down into these, or expanding outward. Both of these approaches allow increased understanding and learning for both the questioner and the person being questioned.

Applying leadership questions in practice:

Specific communication issues can be solved by asking great questions:

When a conversation (in particular, a negotiation) is stuck at a ‘content’ level, and people are taking rigid positions which do not allow compromise or collaboration, then shifting to ‘big picture’ questions allows us to break the impasse. Asking questions about purpose and relationships when content-type questions get stuck, allows those involved to see the content questions in context, allowing them to see how negotiating on a particular content topic where they previously wouldn’t have, helps get them what is really important in the discussion.

Shifting the questions to focus on the purpose of the discussion (the reason why it is important, what the conversations serves in the bigger picture) allows people to get some perspective. Questions like “What are we seeking to achieve by getting agreement here?” can open different lines of conversation and suggest other options of getting the conversation to where you want it to go. We can also switch our questioning to discuss how the relationship between disagreeing parties is important – this brings goodwill and purpose back into the discussion. For example: “We really value how our teams work together, and trust that between us we can get some agreement to strengthen how we do this. How else can we move forward and continue our excellent collaborative relationship?”.

Sometimes we can unlock stuck conversations by using process oriented questions, such as ‘how do you decide X?’ or ‘How do you determine which option has the most value?’ When you work out how the other side makes the decisions (or to help them work this out for themselves), loggerheads can be broken down and steps to move forward can be created. Often, if someone has a process for deciding or discriminating which is ineffective, then this creates the circumstances which gets them stuck. For example, if someone has poor time management skills, the likelihood is that they have a poor process for how they prioritize things. Asking ‘how do you determine what to prioritize?’ explores their process, and once we learn that it is unresourceful, as a leaders we can mentor them to better ways of doing this.

When we ask questions which access fixed thoughts (what they know), then regardless of how we ask, how many times we ask, how intensely we ask, we will always get the same response. However, asking questions which force the other person to start thinking shifts them from their fixed beliefs into discovery. To achieve this, shift our questions to inspirational questions (inviting them to consider, imagine etc,) and softening them can make a big difference. “I wonder”, “What would happen if”,etc., are great examples of questions that encourage expansive thinking.

When not to ask questions:

Although asking questions is a critical skill for a great leader, so is knowing when NOT to ask questions. There are times when an authoritative leadership style is required, and asking questions simply gets in the way of action taking. For example, if the building is on fire, we don’t want someone to spend 20 minutes asking us questions. What is most appropriate in this circumstance is for the leader to direct positive action (everyone get up, walk to the door, down the stairs….etc). In this case, asking questions, regardless of how good they are, is not the right way to lead. Therefore a leader needs to understand when to ask questions, and when to simply lead action from the front.

What can you do next?

Consider what you can do next. If you pay attention to the questions you are currently asking, you can reflect on where they are they adding value, and where are they not. By preparing yourself by getting into the right frame of mind (curious, empathetic), deciding what type of questions are required (deepening questions, or expansive questions), and understanding how you can ask, add then gain agreement on the topic under discussion, you can have immediate impact as a leader.

In the end, it comes down to practice and your desire/frame of mind.

Using these strategies can make you a skilled questioner, able to help yourself and others open possibilities, create consensus, resolve issues and drive enhanced performance.

Learning the skills of great leadership, such as the use of language and asking great questions, are part of The Bigger Game coaching and training approaches. Please contact me if you would like to learn more.

Phil Owens


Phil Owens is a specialist in adaptive change and has spent his career helping people, teams and organizations get unstuck. He has worked with individuals and organizations in over 50 countries to help them adapt and change to experience greater levels of success and create ‘better’ versions of themselves. Phil is the author of several very popular books including: “Mastering the Change Curve: Getting Unstuck and Moving On With Your Life” and “Unstuck: The Strategic Approach to Living the Life You Want.”


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