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How to build resilience in uncertainty

by Patrick O’Donnell

Making Waves Education Foundation » News Stories » How to build resilience in uncertainty

My First Five Years as a CEO: My Biggest Lessons Learned

A few years ago, the Making Waves community came together to define our core values, and one of my favorites is Learn & Grow: We stretch ourselves by staying curious and testing new ideas. We reflect, celebrate, iterate, and share our learning to support others’ growth.  

This summer marks an important personal and professional milestone for me: my 5th anniversary as CEO of Making Waves Education Foundation. It’s been fun to look back on my journey in education and reflect on the lessons I’ve learned and how I’ve grown, especially during my first five years as CEO.  

After starting my career as a teacher, I spent 10 years leading teams at Teach For America. I learned how to be a manager, to lead with an equity lens as a white male, to shape team culture, and to define and drive strategy. When I joined Making Waves five years ago, I was excited to put into action all my leadership learnings as the organization’s first-ever CEO. 

Five years into my role, I am “learning out loud” to share some of the lessons that have helped me get better, be more effective, and sustain my energy and commitment to the work. My hope is that sharing some of my biggest leadership lessons can support the learning and growth of other nonprofit leaders. 

My experience is just one experience – it’s unique to me and these lessons are not a solution to challenges faced by nonprofit leaders. For aspiring leaders and others in executive leadership, I do hope though that you can find something here that resonates with your own experiences or provides a fresh perspective that helps you lead and sustain your leadership in the nonprofit sector.

How to build resilience in uncertainty 

I love my role and my work at Making Waves. The reality is though, the nonprofit CEO job is challenging.

A big part of any CEO role is leading through uncertainty, and it can take many forms: 

When I started in my role, I struggled with this. Uncertainty made me uncomfortable, and I learned that when I experienced uncertainty, I had a tendency to minimize it and try to immediately solve for it.

For example, if someone on my team brought me a complicated problem, I’d jump in to be the problem-solver and give them back a solution. Or if tension built on my team because we had differing viewpoints, I’d impulsively aim to quickly land a plan rather than work through the discomfort together to land the best plan while building our collective muscle to engage in productive conflict.

My discomfort in uncertainty held me back from leading my team in ways that provided clarity, built their leadership, and strengthened our team.  

I will be forever grateful to an executive coach, Chantal Laurie Below, who helped me build resilience in uncertainty. Her coaching was grounded in the idea that leadership is inherently a human and personal endeavor – we bring our personalities, past experiences, and emotions to our leadership. To be at our best, we need to notice our tendencies so we can effectively learn, grow, and lead through them.

For me, I had to notice the moments where I felt discomfort and anxiety in uncertainty and apply tactics to operate with resilience. 

Here are some of my favorite tactics for leading in uncertainty that I hope help you too: 

1. Recognize complexity

Some challenges will be complex and without immediate, easy solutions – and that’s okay. The Cynefin framework is a great tool for recognizing the different types of challenges and how to respond accordingly.

Think of your CEO or leadership role as acknowledging the problem, naming that we don’t yet know all the answers, sharing what we do know, and laying out a plan for working together to identify solutions. 

2. Position your team to do the heavy lifting

Your team can’t learn, grow, and lead if you jump in to solve every challenge. Instead, listen, pose a question, and position them to do the heavy lifting of reflecting and defining potential solutions. I’ve loved this approach since then I can spend my energy thought-partnering with them on these options. 

3. Visualize challenging conversations going well

Before heading into a tough conversation or meeting where it’s uncertain how it will go, rather than fearing a disaster and getting anxious, visualize it going well.

What would it look like if it was a great conversation? What values do you want to be present in the conversation? What actions can you take to steer it toward the positive vs. away from the negative? 

I have a very different relationship with uncertainty today than I did several years ago. That doesn’t mean that I always love it, but I see now that uncertainty is basically a constant in leadership. Now if I feel discomfort in uncertainty, I recognize it, and I can take better steps to move things forward.

More in this series

This article is part of a four-part series by Patrick O’Donnell sharing his leadership learnings as a nonprofit CEO. Follow along with the series below.

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Patrick O’Donnell

Chief Executive Officer
About Making Waves Education Foundation

At Making Waves, we are committed to educational equity. Making Waves Education Foundation is a Bay Area nonprofit that supports Making Waves Academy – a public charter school with more than 1,100 5th through 12th grade students – and leads college and career programming with more than 430 college students.​
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Knowing the opportunities that come with a college degree, we partner with historically underrepresented and underserved students to help make college affordable and graduation attainable. Centering the journeys of our students, our personalized approach includes college and career coaching, scholarships, and financial planning.​
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Our alumni network includes more than 730 college graduates, who earn their degrees and land jobs at more than twice the rate of their first-generation, low-income peers, with 85% graduating debt-free.

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