What are The Right Questions for Decision Making and Strategic Planning?

What are The Right Questions and how does strategic planning link to decision making and achieving goals?

So, having established in previous posts the background to The Right Questions and an idea of their importance, we can now get an overview of The Right Questions and how they are applied to strategic planning and achieving goals, both in a personal or business context. The questions come in an order of sorts but the process of asking The Right Questions is also iterative and cyclical. In other words, the answer to one question is likely to inform an answer to another, and even after we have worked through all the questions we will generally go back and revisit the others to refine our answers.

How to Use The Right Questions Decision Making and Coaching Framework to Achieve Goals

It is beneficial to explore the questions in two broad groups. The first is comprised of the where, what and why, and these encompass the strategic framing of a situation. The second group is made up of the questions how, when, and who and these help us develop a specific plan within the aforementioned strategic frame.

The two groups are joined by ‘which’ as this question deals with the concepts of options and risk. After looking at the overall strategic picture we use ‘which’ to explore courses of action from which we can choose an option to develop into a more detailed plan. We then return to this same question to weigh the risks as the plan progresses. Looking at these options and risks are the key decision points and can lead us to return through the strategic framing or planning loops again.

Taken all together these seven questions create a template for strategic planning and also become a decision-making process that follows a figure of eight cycle, as demonstrated in the diagram below.

“I keep six honest serving-men, (They taught me all I knew); Their names are What and Why and When, And How and Where and Who.” Rudyard Kipling


Why? (Values and Priorities)

The ‘Why?’ represents our values. Our values are our identity; the things at our centre that define why we have the vision in the first place, why we do the things we do, why we attract certain people. They are our beliefs and worldview. These are often things we hold in common with others at one level but the particular combination and application of the values make them unique to us. Knowing our principles shows us what we value most and therefore it also helps us to prioritise and make good decisions.

Where? (Situation and Vision)

‘Where?’ is the present location and the future destination, the situation and the vision. We look at whence we have come from and whither are we going as our journey is bracketed by these ideas of ‘where’. When you get out a map the first thing you do is identify where you are and get your bearings; only once you have done this do you plan to move. And when you move, you don’t want to wander aimlessly (movement in itself is not progress), there needs to be a destination, something we are aiming for. This destination is the dream, the thing that stokes our passion and gives us our drive.

What? (Mission)

‘What?’ represents the mission, the reality of what we are going to do. The mission is the bottom line, the tangible measured difference that we are to make. To work out the mission we need to define success so that we know our finish line. We can then sum this up in a pithy and memorable way to get our mission statement.


Which? (Options, Risk and Reflection)


We have to choose which way to go and therefore ‘Which?’ deals with the idea of selection. First, we have to generate a range of courses of options we can choose from. This is a creative process, requiring divergent thinking, and taking time to step out of the purely logical process in order to examine unorthodox ways of problem-solving. Generating these options is something we can do before looking at the how, when and who questions. We are generally faced with various strategy options and we have to select a route by assessing relevant factors.


One of the major factors affecting a decision is risk. If a venture is deemed too risky it is the surest thing that will stop us from acting, no matter how attractive the option first seemed. To make good decisions we need to identify, assess, mitigate risk and then manage the risk accordingly. Capacity for risk varies between people and situations so it is important to remember that this is an ongoing process of management. At the same time we don’t want to become defensive, timid or risk averse; achieving bold visions means taking risks. We just need to make sure we have counted the cost before we commit ourselves. 


The option does not have to be perfect. What we are looking for is the minimal viable product (MVP) approach to problem-solving. When an idea good enough to add some planning to it, but then we need to test it. This is where the ‘which’ question becomes the reflection point in the interlinking loops between strategic framing and planning. We test our ideas, reflect and learn from them, then adjust our plans and go again.


How? (Strategy, Goals, Planning and Resources)

‘How?’ is the method or plan by which we achieve the mission. Goals and activities support the overall strategy and propel us towards our dream. Breaking down the route into manageable steps gives us the basis of an action plan and makes the dream an achievable reality. Once we have worked out the detail of each task it is much easier to assess the correct resources we need for each step and therefore, by adding up these resources, we can get a better estimate of the total resources we need to achieve the whole mission.

When? (Timing and Programming)

It is no surprise that ‘When?’ refers to time. Timing is critical. Choosing the right time makes the difference between success and failure and it takes an equal measure of planning and wisdom to know when to implement strategies, to go for goals and ultimately achieve missions. Time is key to planning and is the one truly limited resource. As we overlay our plan with time we create a programme with milestones that help us to measure our progress towards our goal.

Who? (Roles, Team, Structure and Network)

The ‘Who?’ is primarily about the roles different people fulfil, the makeup of our team, the structure of our organisation and the people we connect within our personal network. Sometimes we have a mission and then we go out and put together a team and therefore we need to know what we are looking for. At other times we may need an existing team to adopt a new strategy. In this case, we need to know how best to place people as we re-structure the existing team. Even if we are operating alone, not having a specific team or organisation, we always have a unique network of contacts to draw upon. People are always involved one way or another on our journey and they are the most important resource that we can draw upon.

Now that we have looked at an overview of The Right Questions we will look at each one in greater detail in future posts.

If you want to know more about the background and evidence for the approach I recommend you read:

Beyond the 5Ws: Ask questions like a philosopher, answer as a visionary

If you want to start going through the process I recommend you ‘start with why’ (like Simon Sinek) and read the following:

What are your personal values?

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22 thoughts on “What are The Right Questions for Decision Making and Strategic Planning?

  1. How do you access The Right Choice online coaching course? The link on the FAQ page was missing. Is it still available?

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