Friday, August 13th, 2021 8:15 PM — My phone rings. On the other end is a parent in our program at Camp Harbor View. “I’m calling to let you know that I’ve tested positive for COVID-19, and my daughter will not be returning to camp”. 

The call set into motion our protocol of contact tracing and quarantine. The camper had minor symptoms and recovered quickly, and we avoided further cases on our campus in the Boston Harbor Islands. In looking back, this call represents the kind of moment so many of us have faced over these past two years — challenging us to make quick decisions, with compassion and safety in mind, and to continue serving our communities amidst difficult circumstances. 

1. How you practice and prepare is how you’ll play the game: I have always prided myself on setting up effective systems. I have learned, through trial and error, that this is so important to success in every facet of both personal and professional success. Part of this, I must acknowledge, comes from being diagnosed with a learning disability at a young age and having to build systems that worked for my different way of learning (I actually do not see it as a disability, more as a badge of honor that says it is okay to be a little different).

This summer was a completely different beast. Preparation began around the holidays, giving us a six-month runway to develop systems and structures to serve hundreds of unvaccinated people on an island in Boston Harbor. I was tasked with leading our COVID protocols (or, as my staff would say to get a laugh in, the “COVID Czar”). We spent countless hours — with our internal team and external doctors, nurses, and engineers — mapping out scenarios, from testing practices to what we would do in the event of a positive case. Our 35-page playbook was the lifesaver that led to only two positive cases all summer, with nearly 500 people coming to and from every neighborhood in the city.

On my last call with our epidemiologist, she said, “Two cases with that many people, are you kidding me?” to which I replied, “nope, we started preparing for this in January, and I’m glad it paid off.” This process served as a helpful reminder that how we prepare is how we will perform in every aspect of work and life.

2. It’s always about the one-on-one connection: I have worked with many leaders who focus on impact numbers first. I get it, it’s what we are held accountable to as leaders and managers. I remember being a 22-year-old manager at City Year, with 95% of my brain focused on the data, ensuring that our dashboard looked good quarter over quarter, year over year. I’ve changed over the years, no doubt. While I am still driven by results, my approach has evolved.

This summer was a helpful reminder that so much of our work’s success as leaders is grounded in building a foundation and developing genuine connections with the people we lead. If we do this well, we drive greater results for our organizations by creating a culture of connection that brings out the best in our people. Coming out of quarantine this summer served as a helpful reminder that we have to be intentional about this every day and in every interaction.

On a 98-degree day, one of several brutally hot days on the island this summer, I sat down for lunch with one of the young leaders in our program. With that kind of heat, you could not find a person on the island who wasn’t either frustrated or exhausted (or both!). This turned out to be the most impactful conversations that I’ve had in a very long time. We talked about everything from Kobe Bryant to the worries of being a senior in high school. We also spoke about the organization, and I asked my usual range of questions aimed at trying to understand how we are doing as an organization and where we need to be better. One line that has stuck with me from her was, “Josh, people have to feel something to be led by another person, without connection, you got nothing.”

It all starts with that one-to-one connection — and this summer in the trenches of leading through COVID, that mattered more than ever. The young people in our programs never cease to amaze me, or in this case, teach and remind me of the things that matter and make me the best version of myself.

3. People may disagree with a decision, but a lack of clarity is far more detrimental to the success of the team and the organization. On the second-to-last day of camp, we were hit with the most challenging moment of the summer (and likely of my professional life). We had a positive COVID case the prior week, the second of the summer, and we had successfully executed our contact tracing and quarantining plans.

Around 10 a.m. on the last day, the nurses paged me over the walkie. I walked into the office. “What’s up?” I said. “Two kids with symptoms, inclusive of fevers and sore throats.” “You have got to be kidding me. We made it the whole summer, and now this?”. I collected myself, of course, and thanked the team. Our leadership team quickly circled up, and I explained the situation. Looking around that room, we all knew what we had to do, the unpopular yet best decision—pull the plug on camp a day early. We scrambled to communicate and tell staff, executing all of this in about two hours.

I remember walking to the parking garage that evening and turning to my dear friend and colleague, Lisa, and saying, “Did we just ruin the summer for these kids? They didn’t get any closure”. Her response was something that I will never forget—”We may have just prevented an outbreak. We were clear and decisive, and people will look back on that knowing that we did things the right way”.

And this call also represents three lessons on leadership that became clear throughout the challenging — and wonderful — summer of 2021. I took time this fall to reflect on these key lessons.

As we look ahead to 2022, challenges no doubt will still come our way but the experiences and lessons from the summer of 2021 will last a lifetime and they have prepared us for whatever lies ahead.