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Plan to fail – don’t fail to plan

“Plans are worthless, but planning is everything” (D Eisenhower).

Planning is such a critical part of success – but plans are not.  How many times are plans made and simply forgotten?  How many times do people and organisations spend massive time and effort generating a ‘plan’ only for it to be completely out of date before the ink is dry?

We are living through such a reality now – As we go through the uncertainties of COVID, organisations and individuals are describing how they have had to ‘pivot’ and ‘adapt’ – meaning that whatever that they had planned to do has been made obsolete.  If plans are worthless, why should we plan?

Lesson 1: The future is uncertain

“No plan survives the first engagement with the opposition main force” (Helmuth von Moltke, 1871).

We cannot forecast the future with any certainty.  We cannot know – or control – what is going to happen, how others will respond or act, or even how we will change on our journey to the future.

Consider a teenager at high school – they want to be a ‘doctor’ when they grow up. Will they become a doctor?  We cannot know – maybe they will.  Or maybe they find that they hate the sight of blood, or don’t have the capacity to study the subjects that are needed, or perhaps they find that they prefer to paint and become an artist instead.  For each individual, the future shifts with each time they act and learn – the two fundamental drivers of change.

Think about companies like DEC that dominated the early computer industry.  Do you think they planned to go completely out of business?  I’m sure their ‘plan’ was built around remaining a dominant force in the long term.  Competitors and customers had other ideas.  Unforeseen events and changing preferences and technology all put paid to any ‘plan’ DEC would have had. The future is simply uncertain.

Lesson 2: A fixed plan is different to encouraging a process of planning

A plan locks in actions that don’t respond to changing circumstances. “Everyone has a plan until they get punched in the mouth”, Mike Tyson famously said in response to Evander Hollyfield claiming he had a plan to beat Tyson in a boxing match.

Most modern military campaigns are designed around the concept of a goal, and a first step. Everything after that has to be left to the capability to respond. The tactical result of an engagement forms the base for new strategic decisions because victory or defeat in a battle changes the situation to such a degree that no human acumen is able to see beyond the first battle”. (Von Molke)

 So if a ‘plan’ is worthless, why engage in planning?

Planning is about assessment and foresting.  Importantly, it allows an individual, team or organisation to stop and consider their available choices and the consequences of them. It allows learning and preparation that can be vital to achieving a desirable goal. The lack of planning means that we are not able to take considered actions, and often remain simply a victim of circumstance.

Planning allows changes to be made in approaches that make actions effective or simply more efficient.  It also serves as a way of building and reinforcing skills and defining unexpected opportunity that emerges from the uncertainties if the future.  Failing to plan leaves your success up to pure luck.

What should be included in ‘planning’?

The things that should be considered in any planning (strategy) session are:

  • What is our goal? What are we aiming for? (this might change from what you have learned as you move into the future, like the teen that wanted to be a ‘doctor’).
  • Forecasting the environment and circumstances. What do we expect to happen in the near future?  What influence will this have on what we want to do?
  • Reviewing and learning – from successes and failures. Creating a realistic picture of where you are starting from and the resources (including skills and capabilities) available is critical.  Not succeeding is only a failure if you fail to learn.
  • Planning to fail – what could go wrong and how would you respond? What are obvious pitfalls to consider in selecting action?
  • Landmarks of success and failure – how do you know if you are on the right track, or sinking time and effort into a black hole with no positive outcome?
  • What is the next action we will take?

Encouraging continuous planning underscores the process of being adaptive. A ‘Plan’ fixes what you are going to do into the future that is impossible to predict, whereas planning allows continuous assessment of each action step and the possibility of change.  This is not ‘analysis paralysis’ (too much planning), but being open to continuous assessment of how things are going, having a clear action plan and taking that action.

Planning as a process also allows you the space to experiment and explore. It opens the opportunity for innovation rather than fixing people into operational straight jackets. Often a ‘plan’ excludes or discourages innovation as people just keep doing what is in the plan, regardless of its effectiveness or new opportunities that arise.

Self assessment:

  • How do you set your goals?
  • What do you control, and what is out of your control?
  • How far ahead can you reliably predict (the next engagement, different time horizons and levels of certainty)
  • How do determine when to review your plan?
  • How do you define your planning skills?

What can you do?

  • Have a clear idea of your purpose – what is your overall goal state?
  • Stop having a plan and start planning.
  • Think in small steps. Stop, evaluate achievements and define key lessons that enhance your capability to take the subsequent steps towards your goal.
  • Take considered action – without action, planning is simply rumination and anxiety.

You do not know what will happen next. You can only contribute to the creation the next moment into which it can happen. You can only face into the next ‘engagement’ and see how that turns out.


Failing to plan leaves you open to being a victim of circumstance. Planning to fail allows you to understand that circumstance is fleeting, and that developing the skills of assessing, forecasting and acting allows you to move forward, to pivot and to be effective and efficient in moving towards your goals.