“A trap is only a trap if you don’t know about it. If you know about it, it’s a challenge” — China Miéville

Some of the people I have been working with lately have found themselves in planning traps. The symptom these traps have in common is plan paralysis. In spite of the fact that they are unable to make plans, they are often still starting to work on things. Those things just often aren’t the most important thing that proper planning would reveal.

They know a plan is needed in order to deal with the real issues, but they can’t seem to escape the traps that are paralyzing their planning process.

Trap #1: There must be a better or best option.
Leaders get caught in this trap when they keep looking for the “best” way forward. None of the options they are looking at seem perfect, so they keep looking over the same options and wishing for a new super-option.

Trap #2: These one or two things are unknown.
Since we don’t know about these one or two things, we can’t make an estimate. Without estimates for those two things, we can’t make a plan.

Trap #3: There is just too much.
There is just too much of what? Too much to do. It seems impossible to organize and plan this much work.

Trap #4: We will never get done on time.
Usually, this is the trap that is the true driver behind all the other traps. People want a better option because none of the options they currently have get the work done on time. They are stuck wanting to explore unknowns because that allows them to avoid dealing with the hard reality of the schedule. There is just too much, not to plan, but actually to get done.

How do you get out of these traps? All of the escapes are actually fairly straightforward, but the last trap is one that some leaders find difficult.

Escape From Trap #1: Pick an option.
I have seen this trap many times. The top three options are equally good. I say pick one and start planning. They do. The trap is escaped. It is never more complicated than that. Sometimes while planning they do discover some better ideas, but those better ideas just improve the option they picked.

Escape From Trap #2: Make a guess for your estimate.
The one or two unknowns are balanced by over 100 known things. When I point that out, people look embarrassed and say “oh”. Then they feel free to guesstimate and move on.

Escape From Trap #3: Plan the near-term in detail, the longer-term with higher-level estimates. Once people begin detailing their plan in earnest, they start to get overwhelmed with the detail. However, after making a few detailed estimates you feel comfortable with, you can estimate the rest much more quickly. There really are two important aspects of planning. First, have a good plan for who does what when in the next few weeks. Second, know how long it will really take to get the project done.

Escape From Trap #4: Tell the truth about what it will take to get the project done on time. Escaping the first three traps is actually fairly painless. The only reason people make them hard is that they fear to have to deal with telling their stakeholders what it would really take to get the project done on time.

If you follow through on doing the first three steps of escape, you will have a good plan. You will know the truth of how long the project will take. Once you know that truth it is a bit easier to tell it.

I have worked with many clients on all these steps. The truth-telling part is the hardest for first-time practitioners. After they experience getting agreements with their stakeholders on a rational plan that is valuable for them and the customers, they feel freed to do their best work.

Yours in the calm pursuit of excellence,

Alan Willett

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