How to Make Better Decisions

asking the right questions
Simon as a bomb disposal officer in Bosnia

Lessons from a Bomb Disposal Officer on how to ask the right questions in order to make good decisions

I was just savouring a coffee from my newly purchased coffee maker when a wide-eyed and out of breath soldier stumbled into my makeshift office. My cup was poised in my hand – the aroma was fantastic – and the thought of drinking it was more alluring than anything I could imagine that this solider might interrupt me with. This had better be good, I thought. 

“Sir! The guards think there is a bomb at the gates to the camp!”

I put the cup down; coffee time was over.

How do you make important decisions?

Let’s pause the story for a moment so I can ask you a question:

What is the most important decision you have ever made?

The most important decisions are generally not the critical, life threatening type. More likely it was choosing your school, selecting your career, buying a house, or committing to your life partner. How did you make that decision? Was it the right decision? (If you are sitting next to your spouse don’t feel you need to answer that last one just now).

As well as those big life decisions, how about the myriad of smaller decisions we have to make every day. What about those? What process (if any) did you use to make your choice? Every day we are all expected to make hundreds, if not thousands, of decisions. Research has shown we probably make more than 200 decisions a day relating to food alone (Wansink, Sobal). Yet, weirdly, despite all these decisions, very few people ever receive formal training in decision making.

Crawl, walk, run

For me it’s a bit like running.

Everyone just expects people to know how to run. For those of us blessed with full health and mobility it is a natural progression. We crawl, we walk, we run. Simple right?

But if you really want to improve your running you need to train. It was not until I started running ultra-marathons that I really started taking my running training seriously. As I did, I become more aware of the technical aspects of running such as breathing, foot fall, cadence and pace. It was only then, when I broke down my technique, I realized that I had been doing so many things wrong for so many years.

Such is the way with decision making. If you want to get better at making decisions you need to practice, but you must also understand some of the fundamentals of how choices are made.

The science and art of decision making

I started out my career as a Bomb Disposal Officer in the Army. From there I have gone on to lead in various contexts, often in some of the most challenging and hostile environments on the planet. This knowledge and experience, coupled with my love of learning, has led me to develop decision making tools that I teach, particularly to the leaders that I coach.

This is because a large part of being a leader is about making decisions. Effective leadership is dependent upon making good decisions.

The foundation of all my work is asking questions. Questions unlock understanding and understanding is a foundation of good decision making. One of my favourite quotes by Francis Bacon illustrates this:

“A prudent question is one half of wisdom.”

Francis Bacon

So, what are the right questions? This is a question I have been exploring for my whole career. I want to share with you some of the insights I have discovered on this journey over the past 20 years. My hope is that after reading this I can impart a small gift, a simple tool, to help you. Something that you need never forget and can assist you in your future choices and plans. My promise to you is a guarantee that you will be able to remember the framework. And that is because you already know it. All I am going to do is help you apply that framework.

Sound good?

Why do we need to ask the right questions?

Good questions are essential if we want to get the right information. 

If we don’t ask the right questions, we won’t get the answers we need. Without the necessary information, we won’t be able to make good decisions. If we don’t make good decisions, we can lose our direction, fail in our leadership, and can end up ineffective, unhappy or worse.

As I mentioned previously, I found out how important questions are early on in my career as a Bomb Disposal Officer.

Nasty surprises

As I put my coffee down and walked out of the office, I asked my first question:

“What do you mean by a bomb?”

“There is a suspicious package, the guards think it could be a bomb.” was the reply.

It was Bosnia in 2001, and I was a young Lieutenant in the Royal Engineers leading the Explosive Ordnance Disposal (bomb disposal) team in the local region. The conflict in Bosnia had ended some time ago and we were there primarily to clear up the mess that a war leaves behind, namely the mines, mortar bombs and other explosives that littered the countryside. But in the post 9/11 world, the threat of terrorist attack was at the forefront of people’s minds. In this context, an unexplained bag, right up against the front gates of a military camp, was screaming out ‘IED!’ (Improvised Explosive Device) and required immediate and serious attention.

Red wire or blue wire?

Therefore, I went to take control of the scene and do an initial threat assessment. I met the guard commander and asked him some questions such as:

Where exactly was the package?

What did it look like?

Who had seen it first?

When had it been found?

Why was it suspicious?

How had it got there?

Very quickly a picture emerged that put my mind at ease. One of the guards had seen an old and infirm lady dropping off the parcel. Upon questioning the local interpreters, I found out that this lady was well known to them (as she was a little eccentric) and that she had made similar deliveries before. It was more than likely that this was just a gift for the soldiers. A short trip to visit the lady at her house confirmed that yes, she had just dropped off some biscuits for the troops. It just so happened that she thought that dropping off a ‘surprise’ in an unmarked bag, unannounced, at the front gate to a military base was a good thing to do!

After establishing all of this I was able to go back, safely deal with the package (no, I didn’t eat or blow up the biscuits), give the all-clear and return the security levels to normal. I thanked the lady for the kind thought and gift but asked her to refrain from such ‘surprise’ generosity in the future.

So, the right question was not ‘do we cut the red or the blue wire?’ In fact, the right questions were not technical ones at all. 

The importance of questions

When you consider your life is under threat then it is very important to properly assess a situation. You have to overcome the ‘fight or flight’ response and use the decision space – the gap between stimulus and response – to work out what to do. In the time given you have to make an assessment. Asking the right questions and getting the right answers is essential before launching into action. 

The military, the emergency services and medical services know this and train personnel in decision making. By employing decision making processes and then applying these first in exercises and in real-life situations, personnel can build up experience and become expert decision-makers. A good methodology coupled with experience and can help to make quick, effective decisions even in high-risk environments (Klein).

Outside of careers that deal with life-threatening situations very few people get training in asking questions and making decisions. This is despite the fact that numerous studies show that these competencies are essential to employers, particularly for leaders and managers (Harrell, Barbato). The need for decision making in leaders is often expressed in other terms such as:

  • The need for analysing and overcoming problems (Zenger, Folkman)
  • Taking the initiative (Maxwell)
  • Setting direction and goals (Giles)
  • Prioritisation (Tracy)
  • Or having a clear vision and strategy (Kotter) 

But all these things are related to, or dependent upon, good decision making. 

Do we need decision making tools?

We generally take decision making for granted. After all, we each make thousands of choices every day, some conscious, some unconscious, and rarely need to apply more than our intuition to a decision. But there is a problem. Research, particularly by influential figures such as Daniel Kahneman, has demonstrated that our intuition is amazing, but it has limits.

Therefore, understanding decision making and how to make good decisions is critical to all of us, and good decision making starts with good questions. After all, as John Dewey says:

“A problem well put is half solved.”

John Dewey

The problem with many processes and tools, including those used for decision making, is that they are often non-intuitive and hard to remember. That is why we should start with what we already know and structures that are already embedded.

Start with the questions you already know

When I was training as a Bomb Disposal Officer we were taught a question technique called the ‘Five Ws’ which we used when we approached an incident. The ‘Five Ws’ is an interrogative style employed primarily by journalists and police officers, but it is a framework that can be used by anyone to make an appreciation of a given situation. 

The Five Ws are:

  • What? 
  • Where? 
  • When? 
  • Who? 
  • Why? 

To this list ‘how?’ is also usually added. This ‘5Ws and an H’ provides an easy to remember checklist that is a useful starting point towards building a quick but rounded picture of a situation.

The idea is that by using the 5 Ws to construct open questions you are more likely to get factual answers and more information while avoiding presuppositions. This is in contrast to closed questions, that have just yes or no answers, or leading questions that push people down a certain line of thinking.

Using interrogatives

As I have done further research into question technique and applied the principles in my work, I have found that it is also useful to add another ‘W’ – that of ‘which?’ – to the list. The ‘which?’ question covers the concept of selection or choice and therefore helps to inspire options and to consider risk. This helps to complete the decision-making cycle, particularly when we are planning for the future, not just examining an event that has already happened. 

This makes seven questions in a total and creates an easily remembered framework. It’s easy to recall as its based upon the most common interrogative words that we use in English. The methodology easily translates into other languages too. Seven is also a handy number as we find it harder to recall lists above seven or eight items (Buzan).

The application of the interrogatives provides a holistic approach to analysing a situation and making an informed decision. The use and application of these seven open questions is a technique I have dubbed ‘The Right Questions’, inspired by the question I had started with.

Applying The Right Questions

Simplicity is a large part of the system’s strength. But, as with any tool or model, the technique is only as good as its application and it is this application of the questions that we will start to look at here.

My experience of working as a coach and consultant has taught me that The Right Questions approach can be applied to everything from life direction and personal vision, to corporate strategy and organisational change.

The table below outlines the purpose and application of each interrogative word in sequence:

WhyReasonValues, principles, priorities, passions
WherePlaceSituation (past and present), vision
WhatThingMission, end-state, success
WhichSelectionOptions, courses of action, risks, reflection
HowMannerPlan, route, tasks, resources
WhoPersonSelf, team, network, relationships
WhenTimeTiming, programming, prioritisation
Applying The Right Questions

When you learn how to apply the system it is very flexible. My starting point when faced with a challenge – whether it is developing a business case, starting a project, or writing an article – will be to write down the seven Right Questions (often as a mind-map) and start to brainstorm and explore my thoughts under each heading.

After trying this you can also experiment with using the system as a decision-making cycle. My experience over the years has shown that most effective order is as follows:


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I agree with Simon Sinek that we should ‘Start with Why’ when approaching any problem. Asking the ‘where’ and ‘what’ questions then help to frame the problem before moving on to the ‘how’, ‘when’ and ‘who’ elements that are most helpful in developing a plan.

The ‘which’ question then serves as an inflection point between these two loops. Asking the which question helps to identify different courses of actions that can be considered in the planning loop. It may also highlight risks and assumptions that send us back to the framing questions once again.

Putting decision making theory into practice

“Everything should be made as simple as possible, but no simpler.” 

Albert Einstein

Having just read this last section you may be thinking that the process no longer seems so simple. Don’t worry! The best thing to do now is immediately put the basics of the process into practice. 

Start with something easy. What do you have to do today? Take any one task or decision – be that as simple as composing an email, planning a party or even just going to the shops – and start by writing down the seven interrogative questions. Use these to make sure you understand why you need to achieve the task and then how you are going to do it. I promise it will help!

Done? Congratulations! You have taken the first step to becoming better at making decisions. 

Now, as with the running analogy, you need to train regularly. Commit to experimenting with method, perhaps for one task every day for the next week. Once you have used it a couple of times try and apply it to a more complicated issue or more important decision. 

If you struggle don’t be disheartened. You don’t go from the couch to running marathons in one week. Instead, enjoy the learning journey. If this has piqued your interest and you want to find out more then, explore some of the links above, or references listed below, in order to delve into more detail.

Happy decision-making!

If you would like access to some bonus content and get updates then please do sign up to my email list.


Buzan, T (2010) Use Your Head, London: BBC

Giles, S (2016) The Most Important Leadership Competencies, According to Leaders Around the World, Harvard Business Review

Harrell, M and Barato, L (2018) Great Managers Still Matter: The Evolution of Google’s Project Oxygen, Google/Re:work

Kahneman, D (2011) Thinking Fast and Slow, New York: Farrar, Straus and Giroux

Klein, G (1998) Sources of Power: How People Make Decisions, Cambridge: Massachusetts Institute of Technology Press

Kotter, J P (2012) Leading Change, Brighton: Harvard Business Review Press

Maxwell, J C (2007) The 21 Indispensable Qualities of a Leader, Nashville: Thomas Nelson

Sinek, S (2009) Start With WhyLondon: Penguin Books

Tracy, B (2010) How the Best Leaders Lead, New York: American Management Association

Wansink, B; Sobal, J (2007) Mindless Eating: The 200 Daily Food Decisions We Overlook, Environment and Behaviour, 39:1, 106-23

“Mindless Eating: The 200 Daily Food 

Decisions We Overlook,” Environment and Behavior, 39:1 (January), 106-23

Zenger, J and Folkman, J (2014) The Skills Leaders Need at Every Level, Harvard Business Review

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