Lessons on Leadership from my live with Shannon Donnelly

I had a blast last week going live with Shannon Donnelly, the Robin to my Batman, the Thelma to my Louise—the #2 counterpart every CEO needs to help them keep things running smoothly and tackle the challenges of injustice together. Shannon’s personal brand is to “bring order to chaos” and it shows—she helped our growing school go from running based on people and their skillsets to running based on systems. You can catch the replay here or on my LinkedIn page—or below as an audio version on my podcast! Like all great conversations, this one has stuck with me over the last few days, and I wanted to share a few things I’ve been thinking about since we spoke.

At the Teach For America 25th Anniversary Summit, just before Shannon joined the team.

No one among us is indispensable. I remember vividly where I was in real life when Shannon shared this gem with me, and I was glad she shared it on our live. Someone on our team was going to resign, and I was full on panicking. She shared a story about early in her career, when she was about to go on vacation but felt like she couldn’t. Her boss said “Shannon, no one among us is indispensable.” Given that he was the author of the book they were working on, it really stuck with her. I took a deep breath, realized that we would get through this—and turns out, it was a crucial turning point for the better when this woman left. This has reassured me on countless sleepless nights when I was concerned about turnover, and in this age of the “Great Resignation”, I hope it reassures a few readers.

Hold routines sacred. While some of this might common from Shannon’s Discipline Strength (which craves routine and thrives on it), she shares this as one of the secrets to Managing Through Layers which resonated with me. Always have your meetings, check-ins, and quarterly stepbacks—or whatever cadence you’ve decided on—and even in the most hectic of weeks, have them. Shorten them if you need to, or talk about only the most important items, but she talks about how this builds trust in her team and lets them find order even in chaotic times. Shannon also talks about how her direct reports know that when they sit down in those check-ins, she’s going to ask about their top three priorities, and how they are going, as well as their direct reports priorities and how they are going. Because they know this, and know that their priorities should align with their annual goals, people come ready to talk, and she’s able to use that information to help her keep her pulse on her team.

Trust and verify. That said, Shannon talks about not only taking the manager’s word for it—she also gathers her own data on how things are going, from observations, team meetings, chatting with people and holding regular skip-level meetings (where she meets with the people who report to the people who report to her). I apparently gave her this phrase of “trust and verify”. You definitely want to trust your people, and you want to make your own assessment. So much of successful managing is about having an aligned vision of success, and that takes time to get to with someone and can vary by project or workstream. (For example, maybe your Ops Director is ON IT with lunch systems and it runs like clockwork in a very aligned vision, but when it comes to back-end finance work it’s a hot mess… so you still need to align on that.) Trust and verify is a huge part of how you align on a common vision of success.


Your job is to build people’s capacity. As we talked about moving from an individual contributor to manager of managers, she talked about how this advice really reframed her perspective on what her job was. So often we get promoted because we do a great job with our individual contributions and it can be tempting to keep doing that—because that got us to this place so it must be great, right?? Wrong. Shifting your focus as a manager to results and outcomes, and then helping build their capacity in their own way to reach that, is a game-changed.

There’s so much to reflect on but this is what’s top of mind for me this week. Leadership is complicated, managing through layers is complicated, but Shannon’s wisdom helps us all learn and reflect on sharpening the skills that allow us to lead successfully.

What are your takeaways from my interview with Shannon? Leave a comment-I would love to hear your thoughts!

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Five things about leading in large organizations I can’t stop thinking about after talking with Kunjan Narechania