Tolstoy begins Anna Karenina with a flawless blog-entry:  “Happy families are all alike; every unhappy family is unhappy in its own way.” Admittedly he loses his blogging style a little as he goes on for about 700 pages explaining his point.

But there’s more to this epanalepsis than witless wit.   Could it be that our choices and decisions fall into a similar logical structure?  Put differently, is it true that “All good decisions are alike; each bad decision bad in it’s own way.”

In the most simplistic sense this is true.  All decisions that help us achieve our goals are good in that they achieve their end — decision that fail, fail for any of a number of reasons, with luck and execution often playing a prominent role.  It seems very dissatisfying, however, to qualify decisions based on their outcomes.  We all have made a good decision, one that we felt was the right one, only to never see the wished for result .  This is because for all non-trivial decisions there is some uncertainty about the outcome.

The true question is if we can describe a universal optimal decision making procedure that would apply for all decisions where the outcome is uncertain.  Ironically, the quality of a decisions cannot be measured by the outcome at all.  Since we do not know the outcome at the point we make a decision, it is outside of the scope of the analysis.  What we rely on instead is the much less concrete notion of ‘expected outcome.’  The sad secret is that people are rather poorer judges of what will actually happen, than they think.  In short, we are overconfident about our ability to predict the future.

So, what is the universal decision making procedure?  I’ll leave that answer for a non-blog dissertation, but instead offer some observations.  Before you make a non-trivial decision you need to know some things.  Below are some of the things that I look at — I don’t always look at them in a particular order, and some I may look at more than once:

• * When is the earliest/last moment I can make this decision? 
• * What would be true of the outcome that I desire?
• * What are the factors that are relevant in that outcome and how important are they?
• * When examining alternative solutions, how will I select among them?
• * What information do I not have that is important to have — who could help me get it?
• * What evidence disconfirms where I’m leaning?
• * Can I reverse this decision once made?
• * What assumptions about the future am I making in my deliberations?
• * Should someone else (e.g., boss or a direct report) be making this decision?
• * Does how I make this decision matter in getting the results that I seek (i.e., do I need to involve other’s to get their buy-in, understanding, assistance)?
• * Is there a legal, ethical, or moral dimension to this decision that I should consider?

This may seem like a lot of steps, but for a small decision I can cycle through them in a few minutes, or even seconds.  For an important decision it may take longer.  These questions are never superfluous, however.  If the decision is important, making explicit (even if only to yourself) your choice, instead of keeping entirely intuitive is valuable.  If you need input from others it is critical.  If you are making a decision outside of your experience/expertise it is the only way you can really properly make the decision.