“In preparing for battle I have always found that plans are useless, but planning is indispensable.” – Dwight D. Eisenhower”

Planning is an awareness-generating process and one of the things that a good plan will illuminate is your assumptions. Every plan has some assumptions embedded in it; some of those assumptions are unproblematic, while others are crucially important.

While there’s no shortcut to becoming a master planner, one of the quickest ways to excel at it is to learn which assumptions are crucial and approximately accurate. I say approximately because all of our assumptions are rarely spot-on, but in most business matters, close is good enough. (Disregard the “close is good enough” counsel if you build bridges, create new chemicals, and so on.)

For instance, most new entrepreneurs are overly optimistic about how long it takes to accomplish a major business objective. Your gut says that you can do it in two weeks; experience shows you that it’ll take two months. The experienced planner allocates two months, as it’s better to accomplish one objective excellently than to half-finish a handful. When’s the last time you got paid and praised handsomely for a half-finish?

Another assumption that’s embedded into our plans is how many people will buy our products or services. We may not explicitly state that we expect a certain conversion rate, but somewhere in there is the assumption that it will be more than 0%. Unless, of course, we really don’t believe in what we’re selling, in which case it may very well be 0%. Hint: it’s very rarely 0%.

As I mentioned above, some of the embedded assumptions don’t need much attention, as they don’t bear that heavily on your plan, and therefore, your execution. There’s no need to spend time building up an already sturdy wall – find the ones that need some help.

A pattern that I’ve seen most often in my work with clients is that the assumptions that need the most attention are the ones in which the client assumes that they’ll be able to do something radically different from what they did last time. If they had trouble marketing the product last time, what’s going to be different this time around? What internal and external changes have happened since they last gave it a shot that will lead to a different outcome?

Likewise, if they chronically over-commit to projects and have a plan that assumes that they’ll be able to focus on fewer projects, then the assumption is that they won’t over-commit again in the future. Interestingly enough, the overt plan isn’t what needs the most attention in this case; the over-commitment is what will jeopardize the success, not the quality of the plan.

At the same time, you have to assume that you’ll succeed when you’re planning so that you start from a space of “what do we need to do to manifest our success” rather than “what do we need to do to keep from failing?” The former encourages you to think of constructive options that support your abilities; the latter marginalizes your capabilities.

And that’s precisely the reason why sitting down and planning is such a wonderful exercise, even though the plan may not last two days. The insights and awareness you get from the process are really the gems – the rest is just paper or digits.

Take a look at the most important business projects that you have going right now. If you’ve done some planning, which assumptions need the most attention? If you haven’t done any planning, the assumption that needs attention is your belief that you can get it done without planning.

We’d love to hear what you come up with in the comments below.