Lessons Learned from Scariest Leadership Challenges

We pulled together top business experts to comment on their leadership challenges. In honor of spooky season, the theme was lessons learned from your scariest leadership challenges. They didn’t hold back. Whether it was leading through crisis or a challenge to their core values, these leaders did not get spooked. They rose to the occasion and conquered their fears. Here were their stories:

“The scariest period of time in my leadership career thus far was the first two months of the 2020-COVID 19 Pandemic. 

As a healthcare leader, I have never been ‘afraid’ of the unknown. There have always been clinical and leadership experts and peers to bounce things off of and solve problems. What made April to June of 2020 different is that in other areas of the US and world, thousands of people were dying, the care protocols were unknown, medical leaders were building the proverbial airplane while flying, and there were shortages of the very protective equipment that could keep my people safe. I had always had great respect for military leaders who could recall not how many people they had ‘killed’ but how many of their own soldiers they had ‘lost’. The idea of keeping MY team safe was THE MOST IMPORTANT thing to me, and a source of fear that had me talking in my sleep for the first time in my life.

The way I tackled this most scary time was to quickly control the things we could control. We held daily huddles, made quick decisions and really brought daily improvement and daily innovation into action. I set the tone for our work by insisting that we could ‘not let perfect be the enemy of progress’. 

Our best takeaway as a leadership team is that we have shed a previous tendency toward overthinking issues or solutions. We now are able to collaborate, solve and act much more quickly.  Everyone is much more willing to make a mistake because they know that our approach will allow them to respond quickly to tweak solutions… and they all trust each other more because accountability and follow through have been hardwired.”

Kathryn A. McGuire, BSN, MS, RN,
Vice President,
BayCare Health System


“The first that came to mind was actually a leadership situation that required managing up rather than down.  I was leading a fairly high-profile project that was being spotlighted across the entire organization – and this was a LARGE organization. We had regular full company meetings to share these key projects and their accomplishments.  It was a place where the divisional leaders could really show what their teams were doing, and my leader (two bosses above me) was very focused on wanting to showcase my project and connect its importance to a milestone project from several years earlier – essentially showing that he/she was “doing to again.”  My boss approached me and laid out their vision for what we needed to present, and the evidence underlying it. The problem was – the story wasn’t true and they knew it. To be honest it just did not fit with my moral compass, and I gathered the courage to meet with her/him and explain that I would not be presenting the project because I did not agree with what we were suggesting. I said it didn’t feel right.  My boss threatened (several times) even up to the date of the presentation. In the end, though, I believe the truth was known and even resulted in a greater respect for me and what I stood for. It was tough. Funny enough we are still friends today.”

Matt Eisenacher,
SVP Brand Strategy & Innovation,
First Watch Restaurants


“Early in the life of ProVise Management Group, LLC when every dollar of revenue was important to sustain the future of the business, I was forced with the decision to fire one of our biggest clients who had treated the staff very badly. Do I keep the revenue and make the staff wonder about me caring for them and protecting them from abuse, or the reverse. While scary, it was an easy decision. Lesson learned: leadership is about intentional influence and making human connections; leaders must clearly demonstrate their core values regardless of cost; leaders are eco-centric, not egocentric; and there is no wrong time to do the right thing.”

Ray Ferrara, CFP®,
Chair/CEO/CCO,
ProVise Management Group, LLC