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Planning is Guessing … Really?

Decision Point I recently started reading the book “Rework” by Jason Fried and David Heinemeier Hansson, founders of They have a very successful company that’s created some great software, so I was eager to hear what they had to say about creating and running a successful business.

I’ll warn you now, however. This is a thought-provoking book that challenges pretty much every pillar of classic corporate life. If you’ve spent your career as a corporate geek like I have, you’ll likely be quickly offended by much of what they have to say. Open your mind and roll with it; it’s a great book.

Planning is Guessing

I have to admit that I was bristling at what they had to say right from the very beginning of the book. The first chapter has a section titled “Planning is Guessing.”  Seriously?  Guessing?  How asinine is that?  To say that I disagreed with this premise was an understatement.Nothing gets done properly in my world without a plan.

I read that section of the book – and re-read it a couple more times to make sure I understood the point they were trying to make – and decided that they weren’t completely wrong (I can be a jerk stubborn like that sometimes). They were picking primarily on long-range strategic business planning, not necessarily tactical project planning. Having participated in my share of strategic planning sessions over the years, I will concede that there has been a good amount of guessing and wishful thinking built into more than a few of those plans.

Organizational Agility

The authors’ main point with this is that a successful organization must have the flexibility to change direction, to take a different path as business conditions change out from under them, or as new opportunities present themselves. In short, the leadership team needs to be able to improvise and adapt quickly; they need to operate with agility. The authors argue that long-range planning by its very nature stifles an organization’s ability to be agile, primarily because too much focus is placed on the plan even when its relevancy is in question due to changing conditions.

Given this premise, if your organization is not operating in an agile manner, if it cannot turn on a dime as conditions change, is that the fault of the plan, or of execution? I’m going to go with execution (I realize that there is a huge cultural issue here as well, but I’ll deal with that in a later post). For sure, there are plans created out there that are completely unworkable, but for most situations, we have the management and leadership tools available to us to help get the job done – even long-range.

Assumptions – Guesses by Another Name

Let’s back up for a second and talk about why we're giving outsiders the perception that we are spending our valuable time making guesses in our planning process. In it’s most basic form, a plan starts with a goal and works backwards to determine everything that must be done in order for the goal to be realized. Inherent in this list of tasks are assumptions about how things will play out through the execution phase. Will we get the funding we need? Of course we will. Will the required sub-system be completed on time? Again, of course. From a planning perspective, what else can you do? You have to assume that things are going to work just fine. You’ve got to have a starting point and a direction. As a side-note, a funny thing about the word “assumption”; it’s a synonym for the word “guess”. Here then, may be the origin of those pesky guesses.

Risky Behavior

So, how do we turn all of this cold uncertainty into warm, fuzzy confidence? We take each of the assumptions within the plan and ask ourselves, “what happens if things don’t work out like we planned?” By asking this question, we magically transform the assumptions into something that we know how to work with, something without the negative connotations of guesses. Perceived risks.

Using standard risk management techniques, we force ourselves to look into the future and consider the things that can go wrong. Basically, we evaluate each risk, and then create appropriate plans to mitigate the potential negative impact of the risk. This is a very powerful tool – if it’s used correctly. Unfortunately, its frequently not. In order for risk management to be effective, it needs to be applied constantly during a project. I have seen time and time again where this analysis is done near the beginning of a project and then revisited only sporadically, if at all, over the rest of the project. Thinking about the risks in a project should be a daily task. Daily.

Are You Willing to Change?

The second tool that is required is change management, which focuses on how you will deal with any kind of change to the plan. This is the part that will make or break your plan. If you’ve stayed on top of your risks, you should have plenty of warning that things are not going to go as planned. Unfortunately, just knowing that something is going to happen isn’t good enough here. You’ve got to react, and you’ve got to do so aggressively. This is the core part of Fried and Hansson’s argument. If you don’t react quickly to the changing conditions in your plan, you are hurting your company. Bottom line.

Well, is it, or isn’t it?

So, is planning just guessing?  Sure, sometimes, but that’s often just the nature of the beast.  Does knowing all of this mean that planning is a complete waste of time?  Absolutely not!  Your success or failure will come from how you execute the plan, not from the plan itself.  You must have a deep understanding of all of the risks associated with the plan, you must perform constant, daily risk assessments, and you must be willing and able to change directions if the situation and/or environment dictates it.


I’ll leave you with a few relevant quotes.  Enjoy.

Planning is bringing the future into the present so that you can do something about it now. – Alan Lakein (author)

If you have to forecast, forecast often.  — Edgar R. Fiedler (economist)

Informed decision-making comes from a long tradition of guessing and then blaming others for inadequate results.  — Scott Adams (author)

Have you ever worked on a project that you knew was doomed, but the leadership turned a blind eye to the problems? Share your story; leave a comment.


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