Matt Gross, the author of the Frugal Traveler announced he is leaving the New York Times in Wednesday’s column.  He reminisced about the highlights and also listed a few regrets.  In my mind, regret is a symptom of truly trying to contribute or maximize an opportunity.  We depart with regret when we have not accomplished all that we had set-out to achieve or perhaps we learned of alternative adventures.

As board members, staff and volunteers decided to head for new horizons it might be interesting to ask them for their highlights and regrets.  What did not get accomplished during their watch that they felt was important?  What opportunities do they wish they had taken greater advantage of during their tenure with the cause?

Regrets might tell you a lot about your enterprise’s challenges and opportunities.