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.

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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 level. And so if you don't put yourself out there to gain that networking and meet other people that are in the same profession as you, you don't get some of those people where I can pick up the phone and call. I barely know a lot of you on this panel right now, but I automatically feel right now I could probably call Jenny up tomorrow and ask her a question about what's going on.

nurse goal and get some advice. know, it's important. That networking is so important. So important.

Rick Sola (36:28.276)
Yeah. I love that you brought that up because that's kind of been my experience. Sorry, Jenny. I hope I didn't cut you off.

Jenny Woolever (36:28.596)
Yeah.

Jenny Woolever (36:33.862)
No, I totally agree too. And I've been in both secondary and elementary and I really try to form that team in the elementary too. I may not have AP so it's my secretary, it could be my translator, it could be my nurse. We are the office team. Like we're in it together. I don't know what your role is or my role but we're all in it together. So really be thoughtful of that too. Sometimes you do have certain different resources and different individuals. Create that team for you too.

Rick Sola (37:02.656)
Yeah, I agree. think early on, I did not appreciate networking the way it just didn't. Maybe I was so busy with other things as an early administrator, but especially being part of the KPA. And just like we're sitting here, we're all in different parts of the state and having this conversation and being able to connect that way. It's really a big deal, I think. This next question, we'll start with Robert, but I love this question.

It was stolen from a stolen, sounds terrible. was, it was brought in from the new heights podcasts, which is what was your welcome to the NFL moment? So Robert, what was your welcome to administration moment that you had as a first year administrator?

Robert Cave (37:50.702)
So I came into a situation where, you know, my first day of school, was my first year as an administrator. It was my school's first year with a new principal that came from the elementary world that was now coming to the high school. And it was a totally new district for me as well. So I was felt like I was just barely, you know, getting my feet wet when on the very first day we had an incident on a bus that

I to take care of and that was throwing me completely into the fire, not only talking to a parent, but having a parent meeting on day one, you know, trying to navigate Skyward on day one and learn all about, you know, the systems of that, writing a suspension letter on day one and navigating all the legal ramifications of that. now, you know, that was just, luckily I had, like you guys said, a great support team around me to kind of help me do those things.

But it was literally my first day with students as a principal. We had an incident that I had to call a parent, suspend a kid, you know, do all that stuff on day one. And that was really, you know, just throwing me right into the fire with all of those things happening. So, you know, it taught me a lot. It started the year off on an interesting note, but that was kind of my welcome to administration moment, whereas, you know, checking cameras, you know, doing all the things that you do, do the investigation, due process.

all of those things and I was like, man, this is just my first day, you know, what is happening here. So, so that was pretty wild.

Rick Sola (39:23.596)
That sounds like a Baker scenario that I remember when I went through the classes up there. How do you respond with?

Robert Cave (39:28.056)
Yeah. Right. Yeah, exactly. know. Yeah, it was pretty textbook, unfortunately, from what they give you.

Rick Sola (39:36.916)
Yeah. So welcome to the administrator moment, Jenny.

Jenny Woolever (39:42.962)
It might happen before the school year actually even begun. We were needing a teacher and so I was interviewing and I was the only one in the building in the summer.

As I was letting the teacher in, I realized I left my key card on the desk. So her and I were both locked into the entry for quite some time, and it was probably a good 90, 100 degree day. I ended up hiring her she was the best one, but it really let me see when things like this happen, how do you get to really know someone? And so it was kind of embarrassing, but I had to contact buildings and they let me in. But I thought, yeah, you really hired me as your admin, but I made up for it in the long run. But you just kind of have to laugh those off. And again,

Everyone's gonna make mistakes, but that one I really told me, who are you again? I'm your new principal and I'm locked in the entry. But yeah, just gotta laugh it off, but it's still something I truly remember.

Rick Sola (40:24.812)
You

Rick Sola (40:30.952)
Awesome. Midge.

Midge Simmons (40:34.497)
for me, kind of a little bit along the lines of Robert is I can remember back on my first year having a very toxic parent who had gotten in the building. And I came from Garden City Schools as a teacher. And back then we did a lot with crisis and intruders and all of that. And the school I was at was not really up on that. So I immediately put the building in lockdown.

And this had to have been within the first couple months that I was in the role. And needless to say, I was able to get the toxic parent to at least step outside the door. And as soon as that door latched, I knew right then, okay, we're all safe, we're fine. And then all of a sudden a police officer comes and they knew a little bit of what's going on, but they didn't handle it very well because they tackled the parent right outside the door.

Rick Sola (41:29.9)
you

Midge Simmons (41:31.415)
It was quite a thing. I ended up going to court over the issue. The police officer ended up being fired. It was quite a fiasco. I don't remember what the issue was and why the parent was so toxic coming in and angry. I don't remember what that issue was with her child, but I do remember that all happening and me sitting back going, this really what I wanted to do?

But then the year was much better after that, so I don't know.

Rick Sola (42:04.394)
Yeah, that is that that kind of goes back to our question earlier about when things end up in the news and escalate quickly, that sort of thing. But Travis.

TR Travis Rogers (42:11.427)
Yeah.

TR Travis Rogers (42:15.023)
So I had a really good.

admin internship at South High as a teacher. But when I read that I reflected on at 30 years old, I'd left South High to go be an assistant principal at West High. So just up the street. And so they gave me freshman Academy. And so very first day, freshman orientation in front of 400 students, you know, all the staff, I'm doing a 30 minute presentation on the procedures, policies, expectations, never lived a day of my life at West High School. And so just talking

front of people and not just so much teaching but just...

you know now you're the person and now people are looking at you and just being able to present in the correct proper way and say the right things and so that was a truly a very nervous time. never really talked in front of 400 people at the time but again the more you do it the easier it gets and so that was my aha okay welcome to admin I'm 30 years old and I'm sitting here at West High and I'm in charge of all these kids now so.

Rick Sola (43:18.196)
Yeah, it's funny. so I'll give it my, my moment, which is so less than all of your examples, cause it was so minor, but it was over the summer and my office, an office staff person came in and just kind of leaned in. I was brand new a couple of days on the job and just, Hey Rick, I just want to let you know, we've got ants really bad up in the front office. And then she stepped out and I'm, and she left and I was thinking to myself, why in the world are you telling me this?

like deal with it. And then it hit me, wait a second. I'm the facility guy. I'm the, I'm the administrator that's over facilities. That is my job now. I got to, I need to deal with it. And so it was kind of like, yeah, like that's why you're telling me. So, all right, so we're, we'll wrap up here in a bit, but Jenny, you did a really great presentation at KPA, the conference last week on the intentional things you do to promote school culture.

Midge Simmons (44:01.738)
you

Rick Sola (44:15.9)
And we're really at that time of year where it's a grind, but there's a lot of really positive things to tap into for school culture. so talk about a couple of things you're doing or going to do here over the next month with Thanksgiving and the holidays coming that really taps into that.

Jenny Woolever (44:34.504)
Yeah, like Rick said, our jobs are hard, so anything I can do to make staff laugh or get to know them better, it is something I really enjoy and I constantly learn. With being in different buildings too, I've taken some different traditions and added it to mine or I respect what the building has done or some that have run their courses, we could say. And so it's kind of always nice to get a feedback and feel for what others are doing.

We actually just submitted our turkey disguises. So just like those fun hand turkeys, teachers are at home designing one with their families. And so the students all during lunch next week get a vote on which turkey is actually going to make it to the feast. And then they get a gift card to actually use.

TR Travis Rogers (45:00.719)
you

Jenny Woolever (45:15.136)
for their own Thanksgiving supper with their families, which is kind of a fun little artistic standpoint. We're gonna do a champions giving. I'm from Washington and we are the champions. And so each person brings a side and as the principal, we use our funds to get some turkey from Hy-Vee and kind of have our own little friends giving as you would say. December is another one when you come back, you have those three weeks. We've done different where you hide different snowmen throughout the building.

But I really try to make each activity a little different. Some may be where we're playing games, some could be that we're showing artistic side, some may just be socializing or gathering around a table. I just think it's important to embrace that and it gets you out there with others.

I may not participate in everything, but I do participate in a lot. This past Halloween, I was a little boo-boo and I had to explain a lot what that was. But all the kids knew. And you just got to pick and choose, but you got to get out there too. And it's a way that they get to know me besides just Dr. Woolover, the principal.

Rick Sola (46:15.818)
Yeah, climate and culture is so critical in being in tune with the undercurrents of a building. Travis mentioned that trust, trust his staff that you have having people that can come to you and kind of share, Hey, you need to be aware of this and just things to keep the morale high or, you know,

This is a good fun time of year. can be in schools. It can also bring a lot of stress for families, for our teachers and so forth. so, yeah, Jenny, have, and you've been on this podcast before sharing about that. And so for anyone listening and wants to know more, go back to this time last year and Jenny shared a really good, but that presentation last week was great. All right, so we're down to the last couple here. Thinking about...

Those who might be listening who are not yet an administrator, they're in classes that at this point they are considering it or maybe they're wholeheartedly ready to make that jump. What advice would you give to the aspiring building administrator who are not yet in that chair? What should they be thinking about right now? What do they need to consider? And this one's a little bit off script. So I'll just take a volunteer to kick us off. Travis, go ahead.

TR Travis Rogers (47:29.911)
I'll go seek out leadership opportunities and we talk often about your comfort zone and how growth usually happens outside your comfort zone. So whatever your comfort zone is, whether you're teaching or in a different role within a school, you gotta step outside of that and seek out, talk to people, get to know people, be a sponge and you're gonna continue to learn. And I think that's where the impact will happen for you.

Robert Cave (48:00.855)
I would say for me, what I've, what I would learned a lot and what my advice is to be your authentic self, even within this role and listening to Jenny, you know, it reminds me of just kind of myself too, is, you know, that was my fear is it, can I be myself? Can I joke around with staff the way I joked around with my students? Can I do those things? Can I, you know, you know, do those things and, it, and I have been able to, and that's been, you know, don't

Don't try to change for the job. to, you know, be your authentic self within the job and play to your strengths. You're not going to be good at every single thing. There's going to be other administrators, maybe even in your building, your other assistant principals that are, that have different strengths than you. Find what you're good at and lean into those strengths and be your authentic self and don't be afraid to build those relationships and, you know, be that, be the leader you want to be, but within who you are.

and I think I've seen a lot of administrators that, that think they have to change who they were as an educator is, or as a teacher when they get into the role. And I have found that the opposite is true. You should lean into the things that you were good at in the classroom, the things that you, you know, that gave you joy and fulfilled you in the classroom can still be some of the same things that you can do as an administrator. So lean into that and be your authentic self. That authenticity is so important.

not only with your staff, but with students. They will be able to see behind any false veneer that you put up. So be yourself, be who you are, and that's the way you will build trust with your staff and your students.

Rick Sola (49:40.876)
That's great. Jenny.

Jenny Woolever (49:42.281)
Yeah, Robert, I agree. And like you said, you learn from all the administrators you've had before you too. And so people know I spend a lot of time on my pre-service and my professional development because I don't want to be bored. And I said, I've been at all those stages too. And so that is like my classroom. And so I really try to do that. And anytime I can't sub in a class, I love it. And so sometimes even those best administrators aren't the ones that are ready to leave the classroom.

And so just know that you'll always have that. But what's luxury, you can go co-teach with anybody you want. I also agree with what Travis said. I kind of went to the math specialist role before I went to an administrator, and I was glad I did because I learned how to do professional development within large groups. I also learned how to work with teachers and running PLCs. It's different working with adults than it is children. But I also would say is relating it to you as a person. Sometimes when I do have to make those tough phone calls.

I say I understand your view as a parent, I'm a parent too, knowing that you do have a lot of roles and you can relate in all of those. So I think all of those are great and I would agree.

Rick Sola (50:44.46)
right, Mitch.

Midge Simmons (50:46.519)
Robert I really liked what you had to say about being authentic is that that is Yeah, that's just yeah, you hit it spot-on for me. you know it it's not just about building relationships with your staff, but it's also building that trust and And to me that I've learned over the years that that is just so incredibly important to build that trust and you can only do that by being authentic and I I would like to add that

I think it's important that it's okay to be vulnerable with some of your staff. And if you have that trust built, you can do that and it's okay. They need to see that we're human in these roles too. And then the only other thing when I think about this is don't be afraid to take risks. My husband always talks about, you know, it's okay to fail forward.

If you fail at something or if you are empowering a staff member and they fail, let them fail because that's how they're going to learn. But I think that holds true for us too, that it's okay to take risks, whether it's with your staff or whether it's just with the school in general and what you're leading. I just think that's so important because we're not gonna move forward if we don't take those risks.

Rick Sola (52:07.488)
That's great. Thank you all for sharing. Last question, 10 seconds or less. Excuse me. My voice is gone. I apologize. 10 seconds or less. Thanksgiving is a couple of weeks away and we all have some time off coming up. Much deserved. What is it you're looking forward to most to unwind for you personally over the Thanksgiving holiday?

Jenny Woolever (52:34.144)
We do a game night at the Wooliver household and it gets pretty intense. We're all really competitive. I really a lot of times have to be on the same team as Mr. Wooliver because like I said, but we enjoy it you got to laugh at it and my kids love it, but it's just a tradition that carries on in my family. So on Thanksgiving night, it's a game night as well.

Robert Cave (52:58.19)
Yeah, I would say for me, I have a sophomore music ed major at K state. And so he's coming home and so it's spending time. You know, it feels when you, when you have a family and one part of it's gone for a while, you forget what it feels like when you're all together and complete. So for me, it's, know, it's, it's easy to say, I love cooking Thanksgiving food. love eating Thanksgiving food. I love watching football. I love all that, but I love doing all of that when my family is all here and complete and together. So.

That's what it's really all about. And you'll find yourself, I think all of you know, especially those that work high school, how often, how many evenings you work and how often you are out of your family, where you're away from your family. So spending that time with them just feels even more valuable during these times, a time to refresh and get ready for those three to four weeks before winter break hits and we have second semester. So that's I look forward to the most.

Rick Sola (53:53.8)
Excellent. Midge.

Midge Simmons (53:57.09)
For me, this is going to be the first time ever in my career.

in education where I have full week. We've always had only the three days, Wednesday, Thursday, Friday. So to get a whole full week, feels like spring break is around the corner, but it's not going to feel that way outside, obviously. For me, I've got some family members that are actually not going to be there. I could do one of two things. I could be really bummed on that and ruin the week for myself and be negative about that, or I could also appreciate the time that both

my husband and I will have some quiet time together too. and being both of us being school administrators, you don't get a whole lot of that. We do a lot of talking. We have a 40 minute drive. We live in Derby and we both work here in El Dorado. So we do a lot of downtime in there, but.

you know it's gonna be nice to just say hey no we can not be principals for a week and maybe we can have some other conversations that are a little different and have that quiet time too but there will be time for family and definitely time for turkey and all of that too so I'm looking forward to it I'm sure you all are as well

Rick Sola (55:06.613)
Great.

Rick Sola (55:10.23)
Travis?

TR Travis Rogers (55:10.927)
Yeah, I would just echo what everybody said I mean spending time with family probably not checking my email for a few days And then we have a pretty intense Bingo night with the in-laws and so I'm excited to see that again

Rick Sola (55:27.82)
That's awesome. Well, I want to wish you all an awesome Thanksgiving, a good week before you get through without too much going on and that you are able to enjoy that time off and time together. the word authenticity has been brought up, and I just appreciate all of your candor and authenticity with answering these questions. I really appreciate you spending this Friday after school at a busy time to give back to the profession this way.

TR Travis Rogers (55:55.256)
you

Rick Sola (55:57.086)
and to this cohort who has given us these questions to discuss. So once again, thank you all. Have a great Thanksgiving and we'll see you around, I'm sure.

Robert Cave (56:08.278)
Awesome. Thanks so much, Rick.

Midge Simmons (56:08.332)
Thank you, Greg.

TR Travis Rogers (56:08.976)
Take care.