Project Planning Mistakes and How to Avoid the 12 Most Scary Ones

There are many reasons why projects fail*. But, one of the most common is when your plan is at fault. So, in this article, I survey my top 12 project planning mistakes. And because my job is to equip you to succeed, I’ll offer you a solution for each.

When you implement all these solutions, you’ll have a far more robust basis for delivering a successful project. And that’s what we all want.

* I discussed this in two earlier articles, and a course.

A Summary of Our 12 Project Planning Mistakes

1. Forgetting the Real World
2. Believing Your Plan
3. Planning Fallacy
4. History Neglect
5. Narrow Focus
6. Competition Neglect
7. The Illusion of Control
8. Murphy’s Arrogance
9. Hero Pressure
10. Requirement Creep
11. Complexity Effect
12. Black Swans

Mistake 1: Forgetting the Real World

The first thing to know is this:

The universe has no respect for your plans.

I first learned of a wonderful quote from a colleague who had served in the UK armed forces (thank you, Nick). In a presentation, he put up a slide that paraphrased the Seventeenth Century Prussian General, Helmuth von Moltke:

‘No plan survives contact with the enemy.’

In our world of project-based working, the reality of unexpected events is the enemy. Randomness and the unforeseen constantly vie to kick your plans and disrupt your hopes and expectations. 

‘Luck be a Lady Tonight’ sang Sky Masterson in the show, Guys and Dolls. But as a project manager, you need your luck to hold for weeks, months, or even years. It won’t!

Solution: Flexibility

The first of our project planning mistakes is to forget that the real world throws events at you constantly. So sticking to a rapidly outdated plan is foolish.

The solution is flexibility and a willingness to change your plan rapidly. A great model for the way to do this was first articulated in a military context, by Colonel John Boyd. Take a look at our article about Col Boyd’s OODA Loop. This is an essential tool for all project managers. I’ve not heard anyone claim it, but it won’t surprise me if someday an Agile practitioner claims Boyd as an originator of the idea of agility. The two have much in common.

Mistake 2: Believing Your Plan

The impact of events is compounded by my second mistake.

We tend to recognize the truth of von Moltke’s quote and then immediately forget what it means. So, when we come to planning and executing our projects, 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:

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

No. You can do better.

Solution: Contingency

Instead, you should base your plans on an understanding of estimation and error. You need to research the specific mistakes that you and your predecessors have made, time and time again.

And then it’s time to recognize the reality of the self-referential marvel that is Hofstadter’s Law. This was posited by Douglas Hofstadter, in his Book, Gödel, Escher, Bach: An Eternal Golden Braid.

Hofstadter’s Law

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. And we can also adapt it to error rates and any other aspect of your plan. Generous contingency will never let you down.

Mistake 3: Planning Fallacy

Perhaps it’s inevitable. The commonest cause of project planning mistakes is when we forget Hofstadter’s Law. As a result, you underestimate the time, cost, or resources you’ll need.  This is most often the result of over-optimism about what you can achieve. It is therefore also called ‘Optimism Bias’.

But this also often results from political pressures. These may come from within your organization (for internal projects) or commercial pressures (when you are working for a client). It is the cause of many failures of Government-sponsored projects.

Solution: Red Team Review

Don’t rely on your judgment alone. Get other people to look independently at the estimates. Or, if you are dealing with a large, complex plan, find a team of people to review your plans with a skeptical eye. This is your Red Team. They can help with both causes of planning fallacy.

1. Optimism Bias
   It’s known that, 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 that you and your team have superhuman prowess. Yet, that’s the subconscious assumption many of us seem to make about our own work.
2. Political Pressure
   Second, if the over-optimism is driven by political or commercial pressures, a formal red team review is a structured mechanism to counter those pressures. Ideally, you would make this review a necessary part of your project governance procedures. To reduce the biggest and most costly project planning mistakes, make red team review a necessary stage for projects that have:
   • high expenditure
   • political sensitivity, or
   • a high level of complexity

Necessary Corollary

However, there is a necessary corollary here. It is not sufficient to only identify the sources of bias and political pressure: you must address them. This means being prepared to have those tough conversations, speak truth to power, and take a stand where necessary.

Mistake 4: History Neglect

I hope you are diligent and always conduct a lessons-learned review at the end of your projects. If you don’t; you should. It is one of the most valuable parts of your development as a mature project manager. So, of all our project planning mistakes, this is my personal favorite to work on.

But how often do you seek out the reviews of other projects? And do you speak to their senior team members, to find out what they have learned? Do you find out what happened on a predecessor project, before you start planning the next one? And when other project professionals 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. So, it leads us to repeat the same mistakes.  D’oh.

‘Those who cannot remember the past are condemned to repeat it.’

George Santayana

Solution: Lessons Learned Checklist

Undertake a deliberate process of reviewing all relevant recollections, records, and data. Use your review to make a checklist of all the planning failures you find, and risks that materialized. And then use that list to review and adjust your final plan. Even better, give the checklist to someone else, so they can look for project planning mistakes objectively.

Mistake 5: Narrow Focus

Projects can be all consuming. So, too often, PMs get so immersed in their projects that the projects become their whole world. If this happens, you can easily become too inwardly focused – particularly on the aspects of the project you see as your job.

As a project manager, it’s all your job. Yes, you have some specific tasks. But, if you focus too much on them, you can find yourself ignoring critical external factors, stakeholders, or even what other members of your team are doing… or not doing.

Solution: Deliberate Observation

Think like a meerkat. From time to time, put your head up and look around you. What else is happening in your team, your organization, among your stakeholders, and in your social and commercial environment? What’s out on the horizon?

Look for trends and changes. Then, ask how they can affect your project.

Mistake 6: Competition Neglect

This is related to Narrow Focus, but it’s a lot more specific. This source of project planning mistakes arises when you ignore the actions of other people or organizations that are, in some way, competing with you and your project.  When is it in their interests to:

• seize resources that you need
• misrepresent your situation, or
• change to environment in which you are operating?

Who else stands to gain an advantage? These are your ‘competitors’.

While narrow focus refers to benign or neutral forces, competition neglect addresses potentially malevolent interests. At the very least, these are players whose interests can conflict with yours.

This really is conspiracy, and if you are paranoid, then that may be a good thing! Sometimes in a political organization, people really are plotting against you. And, if your project is working on a commercial product launch, for example, your competitors may be too.

Solution: Get inside the minds of your competitors

Consider role-playing a simulation, taking the perspective of a potential competitor. Use this to identify their possible strategies and how they may affect your initiative. You may like our article The Secret to Reading Minds with Perceptual Positions.

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.

Mistake 7: The Illusion of Control

We often have an implicit belief that we are more in control of circumstances than we really are. Two things combine to create this ‘Illusion of Control’.

1. First: the tendency to ignore events and forces that are out of your control and focus only on those that you can influence.
2. 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 points where your plan can fail and focus on those. If you start to believe there aren’t any, then ask a different question:

‘What would be the worst points in our plan for a failure to occur?’

Control what you can control. Then, monitor everything else constantly. This way, you’ll be ready to act on any events or changes that can render your plan out-of-date.

Mistake 8: Murphy’s Arrogance

Murphy’s Law says that…

‘If anything can go wrong – it will go wrong.’

Murphy’s arrogance is acting as if your project is somehow special; that Murphy’s Law does not apply to you.

It does.

Solution: Pre-mortem

This solution also works nicely for many other project planning mistakes – notably 1, 2, 3 and 7. 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. Now ask why each of these could have happened. Then, amend your plan to deal with each possibility, according to its seriousness.

Mistake 9: Hero Pressure

Have you ever succumbed to the temptation to accept a heroic – but impossible – challenge?

That’s the effect of hero pressure, and this is a particular trait of project managers, in my experience. I don’t know whether it is because we need the excitement, the Adrenalin/Epinephrine rush, enjoy the sense of achievement, or crave the adulation it brings. Maybe it’s all of them.

It may bring out the best in us, in some ways. But succumbing to it 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 the telltale signs in you. The solution is therefore to adopt a trusted colleague to act as an alarm bell; a critical friend or mentor, who can say: ‘hey, look out!’

Mistake 10: Requirement Creep

The world changes, and people change their minds. Or they realize they got it wrong. What they commissioned isn’t what they want or need any more. 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.

And the result… Scope Creep.

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.

Mistake 11: Complexity Effect

Far too often, we underestimate the time, budget, and resources that we will need to cope with the complexity of inter-dependencies.

This is unlike narrow focus. There, we don’t see the complexities. Instead, here we just oversimplify them.

The complexity effect kicks in as soon as people need to work together, or you need co-operation from other agencies. We assume, implicitly, that negotiating with twenty people, will take twice as long as negotiating with ten. It won’t: it will probably take four times as long. Complexity rises with the square of the number of interacting parts.

Solution: Simplify

Where you can: simplify. Separate out free-standing work streams and strands of your project. Then 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 of links. And also build in lots of contingency.

Mistake 12: 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 will catch us out. The project planning mistake here is that you focus on the things you know. So, you are over-confident in your belief that all you know is all there is.

But, maybe there are factors that you are (currently) completely ignorant of. It may be time to go and explore!

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’. It gives every officer, non-comm, and soldier the context within which to make decisions. This is vital, in the face of changing battlefield circumstances and an inability to communicate with their commander. It was perhaps most famously used by Lord Nelson, in his briefing to Captains on the eve of the Battle of Trafalgar.

Your project definition, business case, and the goal and objectives your Sponsor or Board have signed off, serve as your commander’s intent.

Conclusion

Don’t let your plan be the source of unnecessary project failure. I have offered 12 solutions to project planning mistakes, on a one-to-one basis. I have matched each solution to a single planning mistake.  But each solution can address multiple problems. And each mistake can deserve several fixes.

But here is the most important planning mistake to avoid. 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 project planning mistake is to not make a plan.’

This article is adapted from an earlier article I wrote for ProjectManager.com.