10 Reasons Plans Fail and How To Change That


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Nothing ever goes as planned. And I think there are two big reasons for this. First, the universe is no respecter of your plans. Randomness and the unforeseen constantly vie to kick them from behind and disrupt your hopes and expectations. In the military context, this has been well known for centuries and is best summed up by the many paraphrases of the writing of 17th-century Prussian General, Helmuth von Moltke: “No plan survives contact with the enemy.”

This is compounded by my second reason: that we tend to recognize the truth of this quote and then immediately forget what it means, when we come to planning and executing our projects. Put simply, we put so much work into the planning process, that we start to believe our plan. So I will offer you a simple rule of my own: “The second biggest planning failure is to believe your plan.”

So, what should we do? Should we just create plans in the hope they are as good as they can be, and then resign ourselves to the scorn of a vengeful universe, actively disbelieve those plans?

No. We can do better. Instead, we should build our plans based on an understanding of some the specific mistakes that we and our predecessors make, time and time again. And then – and only the – we should recognize the reality of self-referential marvel that is Hofstadter’s Law, first cited in his book, Gödel, Escher, Bach: An Eternal Golden Braid. “It always takes longer than you expect, even when you take into account Hofstadter’s Law.”

I believe Hofstadter’s law applies equally to cost, as well. So, with such high stakes, I offer you my list of 10 things that commonly go wrong with plans…and what you can do about each of them.

planning mistakes that kill projects

1. Planning Fallacy

Perhaps inevitably, the commonest cause of plans going wrong is the tendency neglect Hofstadter’s law, and under-estimate the time, cost or resources needed. This is most often due to over-optimism about what you can achieve, but is also frequently the result of political pressures within your organization (for internal projects) or commercial pressures (when you are working for a client).

Solution: Red team review

Ask someone else or, if you are dealing with a large, complex plan, a team of people to review your plans with a skeptical eye. This can help with both causes of planning fallacy. First, while we all typically over-estimate what we can achieve, most of us equally have a more realistic view of what others can do. A red team will not assume the superhuman prowess of you and your team, that you subconsciously believe in. Second, if the over-optimism is driven by political or commercial pressures, a formal red team review can provide a structured mechanism to counter those pressures. Better yet, make this review a necessary part of your governance procedures for projects that have high expenditure, political sensitivity, or the level of complexity that make it a high-risk.

2. History Neglect

I know you are diligent in conducting lessons learned reviews at the end of your projects (and if you aren’t, you should be). But how often do you seek out the reviews of other projects, and speak to their senior team members, before you start planning the next one? And when they do give you warnings, how often do you really listen? Or do you just think: “That was them; that was then. This is me and this is now.”

A common failure is not looking back and learning from the lessons of the past, leading us to repeat the same mistakes. D’oh. Remember what George Santayana famously said, “Those who cannot remember the past are condemned to repeat it.”

Solution: Lessons learned checklist

Undertake a deliberate process of reviewing all relevant recollections, records and data. Make a checklist of all the planning failures your review exposes and then use that list to review and adjust your final plan. Better yet, give the checklist to someone else to review your plan objectively.

3. Narrow Focus

Too often, we get so drawn into our projects that they become our whole world. We can easily become too inwardly focused – particularly on what you perceive as your own job. As a project manager, it’s all your job, and if you focus too much on your own tasks, you can find yourself ignoring external factors that will impinge on what you are doing.

Solution: Deliberate observation

Put your head over the wall and look around at what else is happening in your team, your organization, among your stakeholders, and in your social and commercial environment. Look for new trends and ask how they can affect what you are doing.

4. Competition Neglect

Related to Narrow focus, one specific source of planning error is to ignore the actions of other people or organizations that are, in some way, competing with yours. It is in their interests to seize resources, misrepresent your situation, or to change to environment in which you are operating, to gain an advantage. While narrow focus refers to benign or neutral forces, competition neglect addresses potentially malevolent interests. This really is a conspiracy, and if you are paranoid, then you are right to be!

Solution: Get inside the minds of your competitors

Consider role-playing a simulation, taking the perspective of a potential competitor, to identify their possible strategies and how they may affect your initiative. At the very least, set team members the task of doing “opposition research” and figuring out what they would be doing, were they on the other side of the tracks.

5. Illusion of Control

We often have an implicit believe that we are more in control of circumstances than we really are. Two things combine to create this illusion of control. First is the tendency to ignore events and forces that are out of your control and focus only on those that you can determine. And second is the belief that we can control events that are, in fact, outside our control.

Solution: Understand where failure can happen

Look for the critical point where your plan can fail and focus on those. Control what you can control and monitor everything else constantly, so you are ready to act on any events or changes that can render your plan out-of-date.

6. Murphy’s Arrogance

Murphy’s Law says that “If anything can go wrong – it will go wrong.” Murphy’s arrogance is acting as if you are somehow special and Murphy’s Law does not apply to you. It does.

Solution: Pre-mortem

Before you finalize your plan – and certainly before you start work on executing it – think about what total failure could look like. List everything that could go wrong and amend your plan to deal with each possibility, according to its seriousness. I discussed the pre-mortem process in an earlier blog.

7. Hero Pressure

Have you ever succumbed to the temptation to accept a heroic – but impossible – challenge? That’s hero pressure, and it is a particular trait of project managers, in my experience. I don’t know whether it is because we need the excitement, enjoy the sense of achievement or crave the adulation it brings. Maybe it’s all three. It may bring out the best in us, in some ways, but succumbing also leads to wasted effort and the risk of burn-out.

Solution: Wise counsel

It is hard to spot hero pressure until it is too late. But your friends and colleagues can see it coming and recognize in you the telltale signs. The solution is therefore to adopt a trusted colleague to act as a critical friend or mentor, to say: “Hey, look out!”

8. Requirement Creep

The world changes, and people change their minds or realize they got it wrong. What they commissioned is no longer what they want or need. Some people even take any opportunity to take advantage. You have a project… “Could you just….” These are the three words that project managers fear above all others.

Solution: Formal change control

Constantly review what is needed pro-actively and, when needs change or new opportunities arise, evaluate them using a formal change control process.

9. Complexity Effect

We often underestimate the time, budget and resources that we will need to cope with the complexity of inter-dependencies. Unlike narrow focus, where we don’t see the complexities, here, we just oversimplify them. The complexity effect kicks in as soon as people need to work together, or you need co-operation form other agencies. We assume, implicitly, that negotiating with 20 people, will take twice as long as negotiating with 10. It won’t: it will probably take four-times as long.

Solution: Simplify

Where you can: simplify. Separate out freestanding work streams and strands of your project and build interfaces between them, so you have several simple mini-projects rather than one large and very complex one. Where you cannot do this: understand the complexity effect and that time and resource requirements grow as the square of the scaling. And also build in lots of contingency.

10. Black Swans

Nassim Nicholas Taleb named the Black Swan effect in his book of the same name. It stands for those unknowable future events that sometimes catch us out. The planning risk is that you focus on what you know and are over-confident in your belief that all you know is all there is.

Solution: Commander’s intent

In the face of uncertainty and rapid change, the most valuable single piece of information is your goal: what do you most want to achieve? In military language, this is the “commander’s intent” and gives every officer the context within which to make decisions in the face of changing battlefield circumstances and an inability to communicate with their commander. Your project definition; the goal and objectives your Sponsor or Board have signed off, serve as your commander’s intent.


Don’t let your plan be the source of unnecessary project failure. I have offered 10 solutions on a one-to-one basis, matching each to a single planning problem. But each solution can address multiple problems and each problem can deserve several fixes. Whatever you do, do not consider the difficulties of planning as a reason to not plan. Planning is one of the most important secrets to success, so if all of this sounds a little off-putting, remember this: “The biggest planning failure is to fail to plan.”

One way to plan and succeed is to have the right tools at hand. ProjectManager.com is such a solution, with a battery of online software that allows a project leader to collaboratively plan as well as monitor and report on their project in real time. Try it out for yourself with this free 30-day trial.

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