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.

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Principal Midge Simmons - Grandview Elementary--El Dorado Schools USD490

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Principal Dr. Jenny Woolever - Washington Elementary - Olathe Schools USD233

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Assistant Principal Robert Cave - Piper High School - Piper Schools USD203

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Principal Travis Rogers - Wichita South High School - Wichita USD259

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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 talking to me about something. My go-to is, thank you for telling me. Be sure to email me that so I don't forget. Because there's a million things going on in our mind, and I was already going to do something else, and I couldn't recall. So then at the end of the day, I kind of jot those down on that to-do list so I don't forget. And that's important to go back and don't forget.

I'll even know if my response is late, I'll still get to it. It just is a way I keep track of everything.

Rick Sola (31:36 .96)

That's great. Any other tips and tricks from the other three of you here?

TR Travis Rogers (31:42 .48)

So we have Outlook email and so that schedule send and so when something's on your mind and you can schedule send it because you know it needs to come at a different time has been really helpful. And then the value of a great admin assistant. I have a great support staff here and so they have access to my calendar and we put protected times on there. And so if somebody's trying to find me but I'm in classrooms for that hour unless something's burning.

I am not called, you know, and so really truly sitting down with your trusted folks and building trust with them so then they get a feel for you is in the sense of what's important to you and what's not what could be pushed back via email You know, it's truly just having good people around you and having them know what's important to you

Robert Cave (32:35 .406)

Yeah, I can second the calendar part. That's, that's, you know.

Rick Sola (32:35 .617)

Yeah.

Robert Cave (32:38 .67)

I think what Jenny said to someone comes up to me, I say, send me an email right now. So I get to the top of my inbox so can see that that is definitely a tool I use for sure. But I also think having my calendar available and I, you know, have a counselor or someone needs, but even a student, can, you know, I'm the activities director at my school and I have a club president that wants to have a conversation and wants to plan something. I say, find a date this week, you know, when you have time and final on my calendar and make a calendar and I will accept it. And I, that's, I check my calendar.

You know, every 30 minutes I'm like, okay, what's coming up next? What's the next thing on my agenda? What's the next thing coming up? Because you will find yourself pulled. I mean, I will walk from one end of my building to the other, and I will have seven different people need me, you know, from that end to that end. And I'm heading towards the next meeting on my calendar. So I always am checking to make sure, but I think the email is great, but also that calendar can be really helpful as well.

Rick Sola (33:32 .369)

a good assistant cannot be overstated. And I've been in administration for 15 years and I currently have someone that is just incredible. what she does to help me be better at my job, I can't say enough about that and kind of the nail in the head from Travis there. Travis, I'm going to go to you here. What would you go back and tell?

your brand new principal self. Now, if you could. Kind of a what do know now that you wish you knew then.

TR Travis Rogers (34:09 .433)

That's a great question. I would definitely say to give yourself grace.

My wife tells me often that I am too hard on myself and so seek mentorship, education, it's a small world. Like you said, Rick, we were all in the same room at some point last week and I had no idea. And so depending on your district and your size, you never know the people that have come before you and you don't know the people that will come after you. And so seek out, you don't have to know everything. And so really truly lean into the people around

you and just celebrate the small wins and take time every day to be around kids. So even as a principal I have 1,700 students here at South High. There's lots of times where I'm just like you know what I need to go into a couple classrooms because I just need a break I need to see kids in action and that truly kind of kind of shifts my mindset from time to time.

Rick Sola (35:07 .852)

That's great. Any other advice you'd give yourself?

Midge Simmons (35:12 .631)

When I read the question, the first thing I thought of was networking. know, KPA in USA has been awesome. I mean, since COVID, I feel like it's just been incredible to be a part of. But I was a part of KPA years ago when I first started. I didn't get into it as much. And I just think the networking possibilities that you have through a program like that or, you know, here...

Jenny, you're at elementary, Yeah. So we don't get some of the...

You guys that are at secondary, your league meetings, you get to know some other principals, we don't get that at the elementary level. And that's always been a complaint I've had of being at the elementary