About a year ago when I did my third quarter review for 2011, I ended up with a long list of lessons-learned. I wanted to put those lessons to use in some way, but translating them into do-s and don’t-s felt cumbersome, ineffective – and just plain weird.

So I came up with a list of questions to ask myself instead – a vetting process, if you will – to help me act on those lessons and avoid repeating mistakes without being bossy with myself or reanimating old ghosts.

Of course, I’ve since added questions to the list as I’ve learned new lessons – and taken questions off when the lessons seem to have sunk in deeply enough that they no longer need asking. It’s a continually evolving tool.

I most often use this list after I’ve created a plan for a month or quarter but before I’ve committed to that plan or taken any action. Tweaks have been known to be made. Sometimes entire plans have been scrapped and started over.

On other occasions, I just read through the list when I’m all fired up about a new idea and deciding whether or not to move forward with it.

As we enter a season that often includes looking back at the year as it comes to a close and planning for the year ahead, I will be sharing these questions over the coming weeks. May they help you keep your own best interests and lessons-learned in mind as you reflect on the past and plan for the future.

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Question #1
What is the magnitude of what you are trying to achieve?

Is it small or large in scope? Simple or complex?
How much do you want it? How much do you want
from it?
What does this project represent to you?

Besides the importance of being clear about the What and Why elements of this container, experience suggests that the greater the magnitude, the greater the chance something other than the desired outcome is going to arise in the course of bringing this about.

To put it another way: The deeper and longer you need to dig to make this happen, the more likely it is you will bring up Dirt along with the Treasure.

We covered this a couple weeks ago: completion requires allowing sufficient space and planning appropriate supports to clear away any Dirt that shows up. And the greater the magnitude, the greater the potential for Dirt.

And the greater the magnitude, the greater potential for blind attachment and disappointed expectations. Maintaining some objectivity along with your enthusiasm for the project also requires space and support – regular opportunities to step back and look at the big picture that is forming, ask for feedback from trusted advisors, and reconnect with your purpose. And then to make any necessary adjustments in a timely way rather than enthusiastically barreling through until you’ve pushed yourself into a corner – a position from which it’s difficult to correct for miscalculations (and the general unpredictability of the future).

In sum: The greater the magnitude, the greater the need for space and support. Allow it. Plan for it. Even if in your initial excitement it seems totally unnecessary.

Also: the greater the magnitude, the more important it is to answer all of the questions to follow honestly.

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Next: Vetting Question #2 – How much of this is new?