What We Can Learn from Sheriff James DiPaola: 
How to Admit Mistakes and Make a Comeback as a Leader

Although I tend not to follow local politics closely, I felt deeply saddened by last Saturday’s news that Middlesex County Sheriff James DiPaola committed suicide.

Sheriff DiPaola was reelected to his third six-year term just last month.  After the Boston Globe inquired about his intention to accept pension payment in addition to his salary next year, he decided he could not accept both in good conscience, even though it was legal.  He said, “I’d always be remembered for this, for double-dipping, that that would be my legacy … I tossed and turned all night. I did put myself first this time, and I don’t want it to end that way… I had a feeling in my stomach.’’ Instead, he announced he would retire next month, after 30 years of public service.

When I read his statement last week, I actively admired the Sheriff’s willingness to step up, admit his mistake, and hold himself accountable for it.  It seemed consistent with his stated philosophy “There is no excuse for crime; there is no justification for violence;
 there is no solution without example.”  But his ultimate choice, less than one week later, fails to be a viable solution or positive example for anyone. I grieve for Sheriff DiPaola and his loved ones.  And I’ve been asking myself, what we can we learn?

The spotlight of leadership can be intimidating.  I have felt that tension myself in multiple roles, including entrepreneur.  (I feel it every time I publish a blog post for the world to see, showing my warts and all).  I sense that at this point in time, each of us is being called to support ourselves and each other with increased compassion.  In my life experience, self-compassion has been much harder to come by than compassion for others.  My compassion for the Sheriff, perhaps as much for who he represents as for him personally, remains high.

At the risk of appearing to oversimplify a clearly complex situation, I thought it might be useful to identify constructive actions for us leaders who realize we have erred.  (And honestly, if you’ve never made a mistake, you’re probably not actually leading.)

Here are 5 DOs and 5 DON’Ts for effectively managing professional mistakes and mitigating negative effects.

When you or your business make a mistake, DO:

  1. Acknowledge the error, before anyone else does it for you, and apologize sincerely to your constituency.  By doing so you demonstrate control of the situation and frame the discussion on- and offline.
  2. Provide a plan.  Let those affected know how you will fix the situation and the time frame for doing so.
  3. Make space for feedback.  Sometimes people will need to tell you how the mistake affected them and others will simply need to blow off steam.  Make sure your customers have a clear channel for communicating.
  4. Compensate those who lost out.  If your mistake had any financial implications, cover all losses. In the long-term it will cost you less to do so. Consider offering something concrete to make amends – a free gift or discount may be appropriate, depending on your business.
  5. Look to the future and move forward.  Doing so is essential both to rebuilding your self-confidence and assuring your customers the error will not be repeated.

On the other hand, when you or your business make a mistake, DO NOT:

  1. Evade responsibility.  A consummate professional isn’t afraid to take responsibility when something goes wrong.  Added benefit:  you will be all the more trustworthy for doing so.
  2. Become overly defensive.   You are in the wrong here, and the customer really is right. And even where they aren’t, now certainly isn’t the time to point that out to them.
  3. Shut down communication.  Particularly if solving the problem is a lengthy process, don’t disappear on your clients.  Make sure to update them regularly, even if you’re busy.
  4. Repeat mistakes.  You are entitled to make new mistakes. Making the same one multiple times means you haven’t learned from previous experience.
  5. Harp on the past.  What’s done is done.  After you’ve completed the 5 DOs above, it’s time to move on.

Even well-intentioned leaders face crises, of their own creation or entirely beyond their control.  And every single one deserves compassion.

What’s the biggest mistake you’ve made?  How did you get through it? Did you show yourself enough compassion? Share your stories below so we can all learn from your experience.


  1. Debra Woog


    Thank you so much for sharing all these thoughts! Your point that

    "mistakes most often occurred when I wasn't fully present, focused and centered in myself… I might be feeling pressured, anxious or fearful about something and those emotions are distracting me from giving my full attention." resonated with me especially. In fact, it's an excellent segue to the post I plan to write this week, about what activities we can release from our expectations of ourselves so that we can be fully present to what's important. I'm off to focus on that now. 😉


  2. Coach Christine

    Debra – excellent article! ; )

    Your inquiry about our biggest mistake really got my brain going. I KNOW I've made countless mistakes through the years, that's for darn sure! ~lol I can't immediately recall one BIG one, but what I can distinguish is each time a mistake was made I learned something new about how to treat others and how to more effectively understand and treat myself.

    As I reflect, I find, for me, mistakes most often occurred when I wasn't fully present, focused and centered in myself. That in itself was a huge learning for me!

    My mind might be preoccupied. I might be feeling pressured, anxious or fearful about something and those emotions are distracting me from giving my full attention.

    One of the distinctions I've learned is that emotions are always predispositions for action. We do or do not do something based a LOT on how we feel. We most times are simply not conscious of the emotions running in the background because we've taught ourselves to numb them or ignore them.

    By stopping and acknowledging what I'm feeling before I take action, I have freedom to make clearer choices and that absolutely alters the outcome. The sad part is most of our work culture does not encourage the open discussion, or even, acknowledgment of the role emotions play in the workplace. The mindset is so 'performance' focused, they end up wasting a vast amount of time, energy and resources because of blindly avoiding this emotion connection.

    Another lane I found myself walking down in the past, was beating myself up or feeling shame for making a mistake. I'd feel like a failure or not good enough or smart enough. I now take a moment to objectively look at what worked and what didn't work about the situation. I become the Observer of it and from that place I can better distinguish a few things.

    I can begin to see who I was being in the matter. What was I thinking? How was I feeling? What was I avoiding doing or communicating? What was missing that would have make a difference if it'd been put in?

    It could have been a conversation with a colleague, it could have been putting an event in existence in a calendar, I could have requested support, whatever it might be. Something was clearly missing that would have made a difference and from that place I'm able to more objectively make assessments and decisions about moving forward.

    These days, if I can identify what is occurring in me first, I can more easily begin to see what I need to shift to avoid making a mistake. I can also, in essence, plan for the breakdown in my mind ahead of time by looking to see what needs to be put in to avoid a mistake being made.

    Really, mistakes are less about you or I being bad/wrong people and more about an opportunity to learn and build our awareness muscle, if we are willing. Our consciously choosing to build that muscle sets in motion a whole new way of perceiving and handling life and work circumstances in the moment.

    And one last thought…Anything is possible in communication! : )

    Believe ~ Courage ~ Action!