Episode 87: Making How Matter

With Julie Williamson

Available April 14, 2026

Leadership sometimes feels like a lonely job with lots of competing tasks, but few clear guideposts. Even with the most meticulous planning, we often know conceptually what needs to happen, but falter in articulating how all the pieces will come together. Author, strategist, and consultant/coach Julie Williamson joins host Debra Wilson to talk about the challenges and opportunities of leadership, and what it means to make “how” matter in our work.

Guest: Julie Williamson

Resources, Transcript, and Expanded Show Notes

In This Episode:

• “Changing how you lead means changing some deeply embedded habits about how you're showing up together as a leadership team. How you, as the head of the organization, how you're behaving and what you're doing in the organization to drive the strategy forward. If you're not transforming how you lead, you will not transform your organization, no matter how good the strategy is.” (7:31)
• “The hard things that you want to work on, whether you're a CEO or a head of school, the hard things you want to work on is how do we be in better service to our students, to our families, to our customers, whatever that looks like for you. You don't want the hard things that you're working on to be, got to go wrangle the board again, or I've got to go convince my team that this is the right direction to go. Right? That's not what you want to spend your time on. And that will cause turnovers.” (27:11)
• “So if a leader is feeling a real sense of anxiety or trepidation about meeting with the board in any way, in my mind, the board is failing. Because you should be creating an environment where whether it's good news or bad news, that person feels confident that they have a group of people who are there to support their success and that they are going to partner with them and hold them accountable, yes. You know, challenge them, yes, push them, yes, but make them feel small or make them feel anxious or make them feel unworthy of the role? No.” (31:53)

Related Episodes: Episode 77; 67; 65; 38; 25

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