Entrepreneurial Series, Part 4: The best laid plans

From the Archives

Originally published October 8, 2011

Whenever I have to take public transportation to a new or unfamiliar location, I visit SEPTA’s website and click on “Plan My Trip.” On the next screen, I enter my starting point, destination, and approximate departure or arrival time. The website generates the buses, trains, and trolleys I can take to get where I need to go. It will even let me know whether there will be some walking involved. Essentially, based on the information I give the system, the website really does plan my trip. For entrepreneurs the concept is no different; without a starting point, desired destination or goal, and realistic timelines for accomplishment, the noblest goals and intentions crumble with no real plan to achieve them.

In business I like to think of planning skills as the ability to lay out and implement the steps required to achieve a goal. There are many resources and plenty of information on proven ways to plan in business. While I don’t discount any of them, I have found yet another unrefined method – an almost cynical approach – to achieving realistic goals. (In the last installment on goal-setting, I touched briefly on what realistic goals are.)

My method, formulaic as the next, is rather simple. I encourage clients to identify and clarify a specific, realistic, attainable goal and to name it at the top of a page. This page is folded in half vertically. Down the left side of the page they list all the obstacles, challenges, and reasons that would PREVENT them from achieving their desired outcomes. What do you suppose goes down the other side of the page? Natch. They list everything they can – and will – do to combat those hurdles and to claim their prize, whatever that may be for them.

That’s not the end of it, of course. This should serve merely as an exercise to condition the brain to planning. I like to use this kind of brainstorming in strategic and contingent planning processes. For instance, in direct sales jobs, one obstacle will always be competition. How will one beat out competition to win a sale? There are some unsavory methods, and they have their consequences. Then there are confidence-builders, product knowledge, and other ways marketers can turn prospects into clients. These require some work, and the benefits far outweigh the consequences.

Most aspiring entrepreneurs with whom I work cringe at the mere sound of the words “require some work.” It is the reason many people – and you know people like this; may even be one of them – do NOT plan. How many people in your circle just come up with random ideas about what they want to do and set out to do it without some reflection, introspection, and thorough planning? Thought so. It’s a shame, too, because some of the most brilliant ideas lay to waste for lack of a plan to manifest them, and some of the best laid plans fall short of victory for failure to stick to those plans!

Often accused of overanalyzing, I’m a big fan of the master plan. I like plans. I like planning. I like following plans. I even like out-of-the-box, throw-out-the-book thinking because it can be useful in diligent planning. Is there a point at which there can be too much planning? Sure. When you spend so much time planning, rethinking, retooling, planning, revamping, revitalizing, planning, rejuvenating, readjusting, planning… You get my drift? Spend so much time planning you forget to start implementing?

Bill Watterson’s Calvin, of “Calvin and Hobbes” comic strips, best expresses this sentiment when he quips, “I’m learning real skills that I can apply throughout the rest of my life … Procrastinating and rationalizing.”

So where is the middle ground? How do you know when you’re not planning enough and when you’re just overanalyzing? Simple test: If you spend more time planning something than you will implementing it, you may be spending too much time at the drawing board and not enough in the field, getting the job done. If you just cannot seem to “get it right” despite numerous attempts, or if you spend more time in error than in TRIAL AND error, you may not be planning enough.

Here’s where the five W’s come in handy (is there anything for which they aren’t useful?): Who are the people needed to move the plan toward to the goal? What are the tools and resources necessary? When are the deadlines, follow-ups, evaluations, and other vital checkpoints? Where will specific events and activities occur? Why follow a particular sequence, echelon, communication pattern, etc.? Being able to answer these questions and plenty of other questions you can develop helps form the logic behind reaching a desired outcome.

Another way to look at planning is to use objectives relevant to the overall goal. For instance, in preparing marketing initiatives to heighten visibility of a product, service, or brand, I like to look at ways in which each idea contributes to the overall goal of bringing that brand into the public eye. Someone at the marketing planning meeting may suggest business cards. That’s ONE objective of the overall goal. What are the steps required to print the business cards? Do we have a high-resolution file of the logo? Who will decide what information gets printed on the cards? How much contact information do we want printed on the cards? And so on.

Some homework for you: Assess your planning skills. Read up on goal-setting, review your self-assessment of that skill, and combine it with how you view your ability to plan. Rate yourself on a scale of 1 to 10, 10 being stellar and 1 being dismal. Then share your thoughts, insights, and experiences in comments. We want to hear from you. Share and share alike! And then check back next week for briefings on two other vital entrepreneurial traits: self-confidence and risk-taking. Happy assessing!