I have always thrived on big challenges and been motivated by adversity. I’m not certain where it comes from, but I suspect that family history plays a big role. It’s lessons passed down from a grandfather who dropped out of high school during the Great Depression and kept hustling to find jobs and provide for his family, eventually enabling my mother to become a first-generation college graduate. It’s time spent in the locker room and on the practice floor with my father while he was coaching college basketball, believing he could always come up with a game plan to defeat even the toughest opponents.
It’s that same mindset that makes me enthusiastically jump into a raft, unafraid to navigate the wildest whitewater rapids, in search of both a rush of adrenaline and the wonder of the natural world.
And it’s the same mindset that attracts me to taking on challenges in my work. Over 30 years of professional experience, three recessions, one startup and multiple turnarounds, I have seen more than my share of turbulent waters. I was working in the tech industry during the dot-com crash of the late 90s, and saw the business that I co-owned contract by 40% during the Great Recession. Six months after I joined the board of a charter high school, I learned that Chicago Public Schools wanted to close our school, and three months after being asked to lead an after school mentoring program that was already taking on water, the current pushed us smack into the global COVID pandemic.
Each time I was able to navigate the rapids, keep the boat on course and emerge- if a little wet and a bit scraped up- ready to face the path ahead. Reflecting on those experiences, there are a handful of factors that have been critical in each case to steering the course. I share them here in hopes that some of the lessons from my own journey might help guide other nonprofit leaders maneuvering through their own obstacles.
RELENTLESS OPTIMISM
Maybe it’s all the locker room speeches I heard growing up, but “coach speak” comes in handy when you need to rally the troops. The leader must be an authentic, positive energy force. You have to truly believe you’re going to make it through to the other side, and project that in all of your communications and interactions. Yes, you should be transparent about the rough going ahead, but at the same time you have to give your team, board and stakeholders confidence that together you can sail through.
WINNING TOGETHER
One of my favorite proverbs is “if you want to go fast, go alone. If you want to go far, go together.” Teams that make out through difficult times do it by rowing together. One of the best examples of this that I’ve experienced is when the charter school whose board I served on (and later led as CEO) was nearly shut down by CPS. Given a one year contract renewal, a core group of teachers and staff pulled together, embraced a new curriculum model and committed to changing the school culture and performance. Over the next three years, the school became one of the most improved in Chicago, increasing its graduation rate by over 20 points.
DEEP FOCUS ON PROGRAM PARTICIPANTS
At the end of the day, the measure of any nonprofit organization is the impact it has on its participants. When COVID hit and students in our afterschool program were stuck at home, our team dove in to help kids in any and every way we could. We doubled down on our check-ins with students and their parents, provided extra resources for our school partners and re-worked our program for virtual delivery. As a result, our per school program participation increased by over 30% for the ‘20-’21 school year.
SMART INNOVATION
It can be tempting to minimize the moving parts when your organization is facing hardship, but that is exactly the time to experiment and take calculated risks. Sometimes that means incremental bets, like when we launched a new cloud practice at my technology consulting company in the wake of the ‘08 recession. Sometimes it means transforming your entire approach, as we did at our charter school by implementing project-based learning as the foundation of our school model. Whether small or big, innovation cannot stop when you’re in fast-moving waters, and in fact may lead to the pathway out.
Successfully guiding your team around big rocks, steep drops and fast-moving waters can be among the most rewarding of journeys and take you to places you would never otherwise see. If you lead with relentless optimism, value winning together, focus deeply on program participants and innovate smartly, you can carry through.
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