PMP395: Embracing MESSY Leadership with Alyssa Gallagher and Jen Schwanke

A few words from William D. Parker

Hey everyone, William D. Parker here from Principal Matters: The School Leader’s Podcast. With over 1.4 million downloads and a decade of content for school leaders, our resources are always available for you at As we dive into May 2024, I’m reminded of the craziness this time brings. My wife affectionately dubs this time of year May-cember. It’s a whirlwind of activities and planning, so here are some quick survival tips: maintain a sensible schedule, accept what’s out of your control, prioritize tasks, lean on your team, tackle one thing at a time, and don’t forget to celebrate your wins. For more on staying sane this time of year, check out our 2016 archived episode, PMP014.

In other exciting news, Principal Matters is set to serve over 100 events next school year. We’re booking fast for professional development sessions, both in-person and virtual, covering a range of leadership growth opportunities. Interested? Let’s chat. Schedule a free 30-minute Zoom call with me to explore how we can collaborate. Reach out at or visit for more details.

This week, Jen Schwanke hosts a fantastic interview with Alyssa Gallagher, discussing Alyssa’s insights on coaching leaders and her new book “Embracing MESSY Leadership.” It’s a conversation full of valuable lessons. Thanks for tuning in, and thank you for doing what matters! –WDP

Embracing MESSY Leadership with Alyssa Gallagher and Jen Schwanke

Alyssa Gallagher started her career following a traditional leadership path. Based in California, she was a teacher, then served as a principal, and then worked as an assistant superintendent. These days, she is the Head of North America Programs at BTS Spark, a company that pairs school leaders with the coaching they need. She has co-authored two books with ASCD about design thinking, and a third book, co-authored with her colleague Rosie Connor, is titled Embracing MESSY Leadership. It will be out in May.  

In this episode, Dr. Jen Schwanke sat down with Alyssa to discuss what kind of things she is working on and how her perspective can help school leaders expand their thinking and improve their outcomes.

As part of her work with MESSY leadership, she asks principals to consider five mindsets: 

  • Meaning Making
  • Emotional Connection
  • Sensing the Future
  • Seizing Momentum
  • Your Presence

These five mindsets are the framework for her book about MESSY leadership. Extending them further, though, Gallagher took time during her conversation with Jen to outline several themes that might help leaders reimagine their schools and support other educators. These themes help Alyssa get to her root purpose—a purpose that was established when she was a school leader herself. That purpose includes staying committed to personalized learning for kids, individualizing the learning experience, and meeting people where they are. The themes also come from trends she has identified at BTS Spark, emerging through working with thousands of school administrators in a coaching environment.

A few of these themes include: 

  • Courage
  • Empowering Others
  • Confidence
  • Showing Down
  • Setting Boundaries
  • Seeing the Bigger Picture

Alyssa dives deeper into each of these themes during the podcast, and it’s worth listening to understand how we might connect with each of these to shift our mindsets and make our leadership a little less messy. Of course, as Alyssa points out, leadership IS messy. It’s non-perfect. It’s non-linear. Embracing the mess is, after all, part of the journey. 

Listen to the entire episode for more takeaways. You can find out more about Alyssa, and her amazing team at BTS Spark here.

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William D. Parker
William D. Parker