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 think big and find sustainability
In my first few performance reviews, my board of directors gave me the same constructive feedback – my pacing was way too fast. My senior leadership team gave me the same feedback – we had too many priorities and goals for the organization, which was overwhelming, created burnout, diluted clarity and, ultimately, impact.
Yikes.
They were right. I could feel the intensity and see the burnout on the team. I was driven by “the fierce urgency of now,” the need for our team and organization to be great and to improve quickly and dramatically so we could meet the potential of our students; however, this wasn’t sustainable for the team.
I wasn’t sure what it looked like to both think big AND find sustainability, but I knew I needed to make some changes. Here are the three approaches I took.
1. Set a small number of focused priorities
After I received feedback around pacing, I was about to work with my senior leadership team to set our objectives and key results, or OKRs, for the next fiscal year. This provided the perfect opportunity to learn a new way of operating to set a smaller number of focused priorities
What can this look like?
Create spaciousness
- I worked with an executive coach to build new skills for setting organizational priorities. My coach, Therese Lenk, helped me see that yes, our work is important and urgent, yet if we’re going to achieve our goals, my team needs “spaciousness.”
- Spaciousness means moving away from the constant crunch mode and burnout that comes with tackling too many priorities at once. Instead, focus on the highest-impact strategies, plan in advance, ensure strong execution, and pivot along the way if needed.
Name your growth area
- My coach encouraged me to share with my senior leadership team this personal growth area, state what I was trying to do differently, and enlist their support.
- I told my team I was committed to breaking my past habits. We agreed to define a small number of big priorities and outcomes and throughout the process I’d pause us so we could reflect on the question, “Are we honoring our commitment to a small set of priorities that set the organization up for success?”
Take a multi-year approach
- My senior leadership team was all-in on setting OKRs in a new way, and I learned so much from them about how to do it well, including taking a multi-year approach.
- We don’t need to (and we can’t) accomplish everything we want in one year, so we worked together to a) get clear about where we wanted to be as an organization in three years and then b) define the goals we needed to drive toward in the coming year to get on that path.
The OKRs we defined that year were a huge win for our team. We entered the new year with clarity on what mattered most, we created alignment and coherence across the organization, we greatly reduced burnout, and then we made faster progress because we had the whole team focused on a smaller number of the same goals and priorities.
I have so much gratitude for this phase of my leadership journey.
I’m grateful to my board of directors for giving me feedback on what needed to change and for giving me the space and runway to learn and grow. I’m grateful to members of my senior leadership team for giving me the candid upward feedback, and then locking arms with me to make the changes happen. I’m grateful to my executive coach for giving me concrete tools and approaches that helped me learn and begin walking this new path.
2. Create consistent time to learn and think big
I cherish my weekly morning ritual. I head to one of my favorite neighborhood coffee shops, Le Cafe du Soleil, order coffee and breakfast, and do “big picture” thinking.
This often includes reading articles about the future of learning, the future of work, and leadership best practices; exploring ideas about my vision for Making Waves’ long-term future; and reflecting on big strategic questions and priorities we’re tackling on the team.
I didn’t always do this. About two years ago, I was told that an important part of a CEO’s job is to facilitate clarity of ideas and priorities across the organization.
To do this, you need to carve out consistent time to learn, sharpen your perspective, and do big picture reflection and thinking. Consider this as mandatory in a CEO role. We can’t be booked back-to-back in meetings and executing 100% of the time.
I also create space to do big picture thinking in other ways, like spending a lot more of my time meeting with and learning from other education and workforce leaders in the Bay Area and across the country who are doing innovative work to advance economic and social mobility.
I’ve created a running document where I capture notes from these meetings and have shared it with members of my team so they can be learning alongside me.
3. Prioritize a full life
Last fall, I lived out a lifelong dream of being an actor, making my stage debut in the play Significant Other at the Los Altos Stage Company. For two months, five days a week, I finished work and went to the theater from 6-11 p.m. to rehearse and perform. Heading into this experience, I assumed that these two months would be fun, but exhausting – spending my days as a CEO and my nights as an actor for two straight months.
It turned out to be the total opposite. It was so energizing.
For most of my career, I’ve had a tough time turning off work. In some ways, that’s great – I’m passionate about the work I do to expand educational opportunity, so I’m all in on working really hard. What I’ve learned though is that I’m at my best at work when I’m also prioritizing personal passions.
Throughout the year, I make time for activities that are important to me, like exercising, traveling, and date nights with my husband. And of course, there are moments and seasons when fitting it all in just isn’t doable.
But, I’m getting so much better at it, and I know that being at my best as a CEO means prioritizing both my personal and professional goals to create a full and meaningful life.
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.
How to build resilience in uncertainty
August 29, 2024
Patrick O’Donnell
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.
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.
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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