Using Strategic Questioning to Explore Complex Subjects

“The answers are all out there, we just need to ask the right questions ” Oscar Wilde

At 2112 Consulting, we work from the perspective that strategy creation is based on information, much of which is messy and complex.  Consequently, the first step in the strategy creation process is gathering strategic information. Most of this information is subjective in nature, consisting of the thoughts and views of the key people within the organisation.

This information can, therefore, be difficult to obtain and to manage. As a result, we use tools and techniques that are designed to help us to obtain the views of key people. These are the individuals who will shape the future of the organisation and ultimately be responsible for implement the strategy.

Strategic questioning (also known as Socratic Questioning) is one of the primary techniques that we use. This helps to obtain facts, ideas and assumptions about the organisation and its future. The technique is used in both individual interviews and strategic workshops. In both of these methods, gathering useful information through asking the correct questions is important. The questions should help the individual or group generate ideas, uncover assumptions, examine concepts, identify and explore issues, goals and objectives.


The questions that we ask are critical to the quality of the information that is obtained.  We use a technique called laddering to clarify and expand on the information obtained. This technique uses questions to understand the cause and effect relationship among statements and is crucial to creating a causal map.

Laddering works in two directions. You can ladder up to discover the impact of an idea, action, issue, etc. Laddering down, on the other hand, is used to uncover the cause of the outcome, i.e. what is driving the outcome. Consequently, the questions used in laddering typically fall into one of the following four categories:

Seeking clarification.

As a facilitator you should never make assumptions about what people mean.  It is, therefore, important so clarify what the person means by a statement that they make.  These will tend to be used to narrow the focus of a general statement, in other words, getting more specific information from the participant.

Testing beliefs and perspectives.

Everybody has their own belief system that is developed through their life experiences. These beliefs will influence how they look at things.  Typically, we will have a pen portrait of each of the participants involved in the strategy development process. This will give the facilitator an understanding of their background.  Understand the person allows the facilitator to ask questions to understand how their beliefs may influence their statements. As a result, we can ensure that their statements are taken in the correct context.

Examine reasoning and evidence.

People can make ‘off the cuff’ statements. If taken at face value could have an impact on strategic direction of the organisation.  Consequently, our facilitators will ask questions that are designed to validate the statements. This is done by ensuring that they are based in sound logic and that there is evidence to support them.  We often find that when we challenge a frivolous statement the person will amend or retract it. They may, for example, say “oh, that is not what I meant” or “what I meant to say was …”.

Explore cause and effect relationships.

Causal mapping is the primary tools we use to capture information that is used in the strategy creation process.  A crucial part of this process is understanding the implications and consequences of statements that are made by participants. In addition, this helps to add context to the content that is captured. This is important when analysing the strategic information that has been gathered.


In summary, strategic questioning is an important part of the strategy creation process. Done properly, it will uncover a wealth of detailed information that will ultimately be used as the building blocks of creating a robust strategic for the organisation.


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Related Categories:

Obtaining Strategic Information, Resources

Additional Resources:

Obtaining Strategic Information, Strategic Interviews, Strategy Workshop, Tools and Techniques