What has been your most disappointing moment?

I think there are a lot of ways to answer this question…disappointment in myself? in others? in relation to my business? and so forth.

For the purposes of today’s daily thought question, I’m going to answer it in terms of my most disappointing moment as an entrepreneurial leader (as that is the context the question was originally asked to me).

So here it goes…

I remember my most disappointing moment as an entrepreneur like it was yesterday (because it also doubles as most difficult & emotionally challenging). My most disappointing moment as an entrepreneur was firing the first “long term” employee for which I had high hopes for. This particular team member had been with our company for over a year & was on track to run our newest gelateria & become our first non-family member partner.

Think about it..this is like deciding who to marry. Big decision. Really important person in your life, right?!

I was at a wedding when I got the call. It was Labor Day weekend, 2011. When I received reports of the wrongdoing of one of my team members I was shaking with all sorts of emotion – anger, frustration, disbelief, confusion, guilt, disappointment, and beyond. As much as I wanted to talk myself out of it, I knew the fire needed to happen. It was agreed upon by our leadership team. When someone violates rules that are very clearly laid out & agreed upon, there’s no excuses. Allowing slippage in rule breaking creates a poison that will ultimately kill a company. And I didn’t want that. Driving back from the wedding to the store was such a difficult drive. I rehearsed my planned script the entire way. I was shaking. I got the chills. I couldn’t feel my legs. I felt sick to my stomach. I didn’t want to do this. I knew I had to though.

Why was this disappointing?

I let my team down. Not only did I put my team in a potentially dangerous situation, but I felt like I let them down as a leader. I invested a lot of time, energy, & resources into shaping a future leader only to set us back.
I let my customers down. Customers knew this individual by name & even still asked about the person after the fact. Letting them know that the person was no longer apart of the business wasn’t a fun story to tell.
I let myself down. I let my judgment down. I was disappointed in myself for not recognizing the character of the person before it came to this. I felt like I should’ve been able to predict this & thus prevent it before happening. I was also disappointed in myself for not being a better leader…perhaps something I could have done (or not done) could have prevented this.

Fortunately I learned a lot from this experience. A lot about myself. People. Hiring. Firing. Leading. What to do. What not to do. Hindsight is 20/20 after all.