I don’t play the lottery. As the president of an independent graduate school of psychology, I have enough risk assessment to handle in my life. A friend of mine, however, does play the lottery and recently bought some tickets for a “Power Ball” lottery that apparently had accumulated quite a large sum of money for someone to win. Having been doing quite a bit of reading in recent years about something now called “behavioral economics”, I began to think about what must be going through the minds (and hearts) of those who did NOT win the lottery.

Specifically, I was wondering what it would be like to have a lottery ticket that is only one number off from the winning ticket—if this is a lottery where you get to pick your own number. Or what about the person who holds a ticket that was purchased at a store where the winner also bought her ticket? What if you purchased your lottery ticket one minute before or one minute after the winner bought her ticket. The behavioral economists do research on and write about the impact of almost wining something.  It is the person who is just a moment away from success or that could have won “if only” that shows the strongest signs of regret.

Having missed the lottery by one number is much more painful than missing it by twenty numbers; it is also much more painful if the lottery ticket was purchased in the same store at almost the same time as the winner (“if I had only not purchased that extra box of cereal and gone directly to the check-out counter to get the winning ticket!”). What do we do after we experience the regret? What decisions do we make and what actions do we take? Do I say “chance passed me by . . . “ In which case, I’m going to avoid this lottery at all costs in the future. Or so we say “I’m so close I can taste it” and participate even more earnestly in this lottery.

Behavioral economists like Daniel Kahneman observe that regret evokes much stronger emotions that either the thrill of winning or the agony of defeat (and loss). There apparently is nothing more motivating than seeking to avoid regret for a decision that was wrongly made or for a decision that was not made. And it might also be the case that nothing is more decisive than the decisions we make and actions we take post-regret.

What about the men and women we coach—either as a personal coach or coach to an organizational leader. What role does regret, the avoidance of regret, and post-regret decisions and actions play in their lives and work? In what ways, if any, do we help our coaching clients address the dynamics of regret?

As a starting point, I would suggest that the following questions be posed. These questions might engender reflections by our clients about the dynamics of regret in their own life and work: