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 which is subjective in nature, consisting of the thoughts and views of the key people within the organisation.

This information can be difficult to obtain and to manage so we use tools and techniques that are designed to help us to obtain the views of 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 to obtain facts, ideas and assumptions about the organisation and its future through either individual interviews or strategic workshops. No matter which technique is used to gather the information, it is important to ask questions that will 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 during the information gathering phase of the strategy development process. We use a technique called laddering to clarify and expand on the material obtained by asking questions to understand the outcomes of activities (laddering up) and what activates should be taken to achieve an outcome (laddering down).  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 and 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 which will give our facilitator an understanding of their background.  This allows them to ask questions that will test how their beliefs are influencing the statements that they are making to ensure that they are taken in the correct context.

Examine reasoning and evidence.  People can make ‘off the cuff’ statements that 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 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, saying “oh, that is not what I meant” or “What I meant to say was …”.

Explore cause and effect relationships.  One of the primary tools that we use to capture information that is used in the strategy creation process is causal mapping.  A crucial part of this process is understanding the implications and consequences of statements that are made by participants.   This also helps to add context to the content that is captured which is important when analysing the strategic information that has been gathered.

In summary, strategic questioning is an important part of the strategy creation process as, 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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