CC#106: Navigating School Leadership (part 2) - Principal Panel w/ Simmons, Woolever, Cave, and Rogers

(part 2 of 2) In this episode of "Cool Coffee," host Rick Sola moderates a panel of four principals from Kansas, discussing their journeys into administration and the challenges they face. The panelists, including principals Midge Simmons, Dr. Jenny Woolever, Robert Cave, and Travis Rogers, share personal stories about their motivations for becoming administrators, the importance of authenticity and trust in leadership, and strategies for managing school culture and crises. They also offer advice to aspiring administrators, emphasizing the value of networking, being authentic, and taking risks. Questions to the panel came from Baker University Fall 2025 cohort of future administrators.

This is part 2 of a 2 part episode. Part 1 (CC#105) dropped on November 20, 2025.

Connect with the panel... Principal Midge Simmons - Grandview Elementary--El Dorado Schools USD490 Connect with Mrs. Simmons on X

Principal Dr. Jenny Woolever - Washington Elementary - Olathe Schools USD233 Connect with Dr. Woolever on X

Assistant Principal Robert Cave - Piper High School - Piper Schools USD203 Connect with Mr. Cave on X

Principal Travis Rogers - Wichita South High School - Wichita USD259 Connect with Mr. Rogers on X

 

 

The mission of the Kansas Principals Association, an organization committed to educational excellence and the lifelong success of all students, is to develop and support all principals through optimized learning, collaborative leadership, networking, and service. Read more about the KPA HERE.

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Episode TRANSCRIPT (AI generated, continues from the end of CC#105-part 1)

Rick Sola (29:25.312) what organizational methods or systems do you have for staying on top of all of the to-dos that you have and that you never complete at the end of any given day?

Jenny Woolever (29:36.985) I've had to learn that my to-do list is always a to-do list. I used to be able to get to-do list done. Yeah, you don't in this role. It is always there. You add to it, you bump things up depending on what's the need and sometimes you can't even get to the to-do list so you have to be able to accept that going in. That was probably something I really had to learn my first few years. I have had an opportunity within my 13 years I have been in different districts and also different buildings.

And so each building I found success in, first I understand what everybody's role is. So when I visit with the secretary before the school year starts, or I visit with assistant principals, maybe that's the counselors, I have them really define their role. So that way when we have the start of the year, we have our names and we know who they can go to for what. That really helps eliminate some of that, them going to you to ask, well, who does this? It's already in that plan. So I always kind of recommend.

empowering others, but also we have some clear plans in place ahead of time. And many a times we're working together anyways, but it's just nice to have that process already thought out. The other thing I recommend is a lot of committees with my, you know, sitting, we'll kind of talk about climate and culture, but having a social committee or during PLCs at the end of that, I always go back to, okay, let's review what everybody is doing. So it doesn't just fall on one person. you're going to send this email? Great. I'm going to contact the parent? Great.

TR Travis Rogers (30:44.419) you

Jenny Woolever (31:02.388) That just really helps come together. And the last bit of advice I had on there that I marked was, in passing as principals, we're always going through the hallways. Someone will be ta