(part 1 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...
(part 1 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 1 of a 2 part episode. Part 2 will drop on December 4, 2025.
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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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FULL EPISODE TRANSCRIPT (Generated by AI)
Rick Sola (00:03.167)
Hello and welcome to Cool Coffee, a principals panel edition. We have four amazing principals here from across this wonderful state of Kansas. I'll have them introduce themselves in a bit, but today's panel will be served up some questions created by the Baker University's Fall 2025 cohort, which are all students working toward their building level licensure program. They are future administrators. Special shout out to Shelby Mouha.
from this cohort who helped facilitate the creation of these questions and with the aim of going beyond the surface level and into the nuts and bolts of administration. We know there are many ways to skin a cat, which is just really one of the most awful sayings. I apologize for putting that in there. So for those listening who are in their chair, compare your response with how our panel responds. There are often many right answers, perhaps even many more wrong answers, but still there are many correct answers. So with that,
Let's meet our panel today and they're gonna share their name, position, school and their number of years in the chair. Let's start with Midge.
Midge Simmons (01:10.551)
I'm Midge Simmons. I'm an elementary principal at Granville Elementary in El Dorado. I've been in the chair too long. All good though. I do feel like I'll be ending my career here in El Dorado, but we'll see how life takes us. But I've been in education for 29 years and 19 as an elementary principal. This is my third school, third school to be an elementary principal.
Rick Sola (01:39.433)
Awesome. Welcome, Edge. Jenny.
Midge Simmons (01:41.003)
Thank you.
Jenny Woolever (01:44.224)
you
Rick Sola (01:46.546)
I think you're on mute, Jenny.
Rick Sola (01:52.811)
There you go. You're all good.
Jenny Woolever (01:53.342)
Not a good way to start. Okay, I'm Dr. Jenny Willow. I am the principal at Washington Elementary in the Lathus School District. I've served as a principal for 13 years. Four of those have been in middle school and the remainder have been in elementary.
Rick Sola (02:07.711)
Awesome. Robert.
Robert Cave (02:10.286)
Hey, I'm Robert Cave. I have been a, an assistant principal at Piper High School in Kansas City, Kansas. I spent 23 years teaching in Olathe schools and was part of the Baker admin cohort in 2018 and finally got a job at Piper High School and this is my fourth year there. So I've been in education about 27 years, only four as an administrator, the rest is a teacher.
Rick Sola (02:39.977)
Awesome. And Travis.
TR Travis Rogers (02:43.151)
Hello everybody, I'm Travis Rogers, currently principal at Wichita South High School. This is my 19th year in education, 12th year as an administrator, and I'm just starting my fifth year as principal here at South High School in USD 259.
Robert Cave (02:44.32)
you
Rick Sola (03:00.669)
Awesome. Well, once again, I want to welcome all of you. And it was great because we're recording this the week after the KPA conference. And I was able to see many of you there. It was a great conference and it was actually neat. At one point, I think we were all in the same session. But thanks again for coming on to this podcast and being able to share specifically to our Baker friends out there in this cohort, but also to all who are listening. And so we're going to, we're going to kick it off here.
And so these questions again were generated from the Fall 2025 Baker University Future Administrator Program. And so I'm going to start here with a question that kind of applies to all of us. And Midge, we'll start with you, but we'll hear from everybody. going way back, why did you decide to become an administrator? And how has that why changed throughout the year or throughout the years?
Midge Simmons (03:59.828)
Well, I was ready to answer number one, Rick. You jumped us to number eight. You're good. You're good. You know, I probably will give an answer that not many would say. Honestly, I was bored. I was bored teaching. I think it was at the time I was teaching middle school.
Rick Sola (04:03.115)
I won't go out of order after this. I just thought that was a good kickoff. Sorry about that. little curve ball.
Midge Simmons (04:23.603)
and I had maybe one to two preps and I just needed something more and I always had aspirations of trying to make more of a difference than what you can in a classroom and trying to reach out to others with more of a difference and so I know that sounds kind of, I don't know what the word for that is, that most people would give that in an interview type question but it's the truth. I wanted to have a greater capacity of being able to
make a change or trying to make a difference. don't know. I think for me, I've learned that it's not always about the difference in pay in the education world or the administrative world, but it has a lot more to do with the support that you receive.
I've had some varying experiences being an administrator in three different districts at three different levels going from 3A to 2A and now I'm at 4A level. I just think that the support that you get from a superintendent and a board is huge. That to me makes the biggest difference. And I think I've seen that over the years. And I've left districts because I didn't feel.
that support, whether it superintendent or the board. And it's time to move on and try and make a difference somewhere else. so, yeah. You guys have anything?
Rick Sola (05:58.7)
Great. Yeah. Travis will kick it to you. Why'd you become an administrator?
TR Travis Rogers (06:04.333)
Yeah, so I had a really good experience. taught PE actually here at South High School and so about year four or five really started to reflect and think about what my next chapter was going to look like. And I was always interested in like the functions of a school and so I had about 150 kids throughout my PE classes. Again, was able to coach some things again had a really good experience, but I wanted to make a greater impact.
And I thought growing personally and professionally was very important. And so what's funny now in my 12th year, you're still coaching.
you still mentor, but now you're on a bigger scale. And so now you're involved, you know, with families, parents, you know, the staff. And so it's kind of like pieces of the puzzle. I say that often. And so you're trying to put all the pieces of the puzzle and depending on your school, depending on your situation, you know, depending on the day, you could have a couple pieces that you got to put together or you could have a lot. And so, it's really been impactful, but really truly serving your why is serving your people.
So it's all about that personal and professional growth and in this role it can happen every hour.
Rick Sola (07:22.859)
Great Robert.
Robert Cave (07:24.584)
you know, for me, I was in the classroom. I didn't know if I was ever going to be an administrator. That wasn't ever my end goal. you know, I thought I was going to be probably a lifelong teacher and I kept finding myself and kind of thrust into different leadership roles, whether it would be curriculum, whether that be, you know, writing different things or department chairs, BLT chairs, those sorts of things. And, kind of like what Mitch says, I found myself kind of yearning for a little bit of a different.
side of education for a different way to impact not only students, but to impact teachers and try to help support them and kind of be the, you know, the one to help lift them up and help students achieve. And found myself, you know, taking, getting another masters in the Baker cohort and just, and getting that school leadership and really finding a passion for that. And so ended up just kind of throwing myself into that. So, you know, my biggest fear was that
I would miss out on kind of the relational aspect that you have as a teacher. That was kind of why I still did it. I loved being with students. I loved seeing them grow. I loved all of those things. But you find that there's, you still get to have that as an administrator. It's just at a different level. Now you have it with the teachers. Now you can impact things in different ways and your scope and sphere of influence will grow in that way. So I found that to be still pretty powerful.
And it's kept me, you know, still wanting to be in education and be an advocate for educators instead of just the ones that we're educating.
Rick Sola (08:58.581)
Awesome. Jenny?
Jenny Woolever (09:03.092)
Well, I think others saw it in me first before I really wanted to come to fruition that I probably will be a principal. I went through my schooling and I actually started towards my doctorate. I didn't have any kind of educational leadership previously for that. I went into EdTech, did some other things. But the reason I was pursuing my doctorate, I was interested in teaching those that wanted to become teachers and become in education.
During that is when others saw it in me and said you really need to go back and get your certification in educational leadership and so I think with their encouragement is what drove me into this and just kind like what Mitch said too is that I actually went to a math specialist first because I was so worried about leaving that role like many of you guys said but the greater impact you do have as you kind of go through as a specialist and then as an administrator I really felt like I
could really impact not just my classroom, but a whole building.
Rick Sola (09:59.68)
That's great. I love hearing all of your, your whys and you know, think it highlights that there's no one road to this chair. And that's usually how we start this show is your road to the chair that I hear so often how kind of like what Jenny said, didn't necessarily think about it for myself. Somebody else may have discovered it. All four of you described a much different path and why, and you know, for those who are listening who
May be in a teaching role right now. I think that's important to realize like sometimes I think we feel like we have to emulate somebody who were with or near There's a lot of different ways to get there and in at different trajectories different timing as well we'll go into the the first question major I'll go to you as far as You know the the first one in order I guess we'll be back in order here Is perhaps one of the most important things if not the most important thing we do and that's hiring
And we hire candidates that we are hoping will be a good fit. But what does it mean that you are looking for in teaching candidates for your building? And then what do you tend to avoid?
Midge Simmons (11:09.783)
Well, for me, a lot of times my husband's also a principal. And so he has laughed at me over the years because when I am down to the wire, you've got it narrowed down to two candidates and you're trying to make some decisions and they all have great qualities and they all have some negatives. When you're trying to figure out which one to go with, he always says to me, what's your gut say? And he makes fun of me because he says,
when your gut is right, it's right, and when it's not, it's not, and you, nine times out of 10, are always right with your gut, and he's right. mean, all the hiring I've done over the years, it does come down to what do I feel in my gut? But the biggest thing, biggest things for me is going to be when I'm looking across the table at somebody that we're interviewing, it has everything to do with relationships. And...
I don't mean just relationships with kids, relationships with other staff as well. Do they fit the mission and the vision of our building and where we're headed in the future? Do they fit the mold of the teammate that they're going to work with, right? I mean, I have teachers that team, I mean, we all team teach on our grade levels at the elementary level. And if I feel like it's not the right fit, it's not the right fit. It doesn't mean that the teacher won't be good.
couldn't be a great candidate for us. It's just if the fifth isn't there, it's not. I feel like sometimes we think a GPA is everything, but a GPA to me tells me whether a student, whether a teacher is going to have a good work ethic. That's what a GPA tells me is whether they have a work ethic. If the person can't relate to others.
They could be a straight A student, have all these honors, but if they can't relate to others and be able to build relationships with kids and with staff, I'm not going to find them to be a coachable person to hire. And that's the other thing that I really look for is, you you find out what somebody's faults are through an interview, and I always ask myself, if they have that kind of fault, can I support that as a principal?
Midge Simmons (13:26.305)
Can I coach them through that and coach them up on that? And there are times when you interview teachers and you look at somebody and think, hmm, I don't know. I don't know if I can coach that. I don't know what supports I can bring in to help them. And maybe they're not the right fit for that. I laughed when I read this question because I was reflecting back to what did this look like 19 years ago when I started as a principal?
And I literally had, I remember sitting at my desk one time to hire an elementary teacher and I literally had two feet worth of files to go through to hire one position. And now we're lucky if we get one application at times, right? Especially you guys that are at the high school and middle school level. I know it sometimes gets worse than some of those, but it just.
TR Travis Rogers (14:10.831)
you
Midge Simmons (14:21.855)
It's amazing in the 19 years how much that's changed in our profession and it's sad. I want more for this profession that's given me a life. nowadays we're lucky. We want to find people that definitely have some sort of a license. We run into some cases where we try, I mean here at El Dorado we try and avoid anybody that doesn't have any license.
if we can, because we do get applicants that have no license. They're still working on it or whatever program that they have. And I think I feel like as a principal, I have to be more open minded for that coachable piece in hiring teachers.
Rick Sola (15:09.579)
So I really like that you brought up your gut and kind of looking at the panel here. And I agree with that. There's so many times where you've got to, you've got to go with your gut. Has your gut ever let you down in a hiring situation?
Midge Simmons (15:22.999)
It's funny because the last school that I left, I hired somebody before I left and my gut felt funny, but I didn't have any other applicants to fill the position and we had to go with it. And then I didn't plan on leaving. I hired them, I think late April and I ended up leaving in early June to come here and it was not a good situation. They ended up...
non-renewing and barely made it through the school year. So no, my gut failed me on that one, but I didn't reap the negative side.
TR Travis Rogers (15:55.695)
you
Rick Sola (16:01.013)
Well, you know, it can cut both ways. I'm sure we've all been burned by hiring. If you don't trust your gut and that fails, that's really hard to swallow, at least for me. Like if I go against my instinct because, know, so I think I'm glad you brought that up. think it's a really important piece. Robert, I'm going to kick it to you. How do you keep your cool when staff or students come to you with an issue that is a 10 on the emergency scale for them?
Robert Cave (16:28.577)
Ha
Rick Sola (16:30.773)
but it's absolutely not a 10 for you.
Robert Cave (16:33.944)
Well, I think, you know, the biggest thing is to listen. You know, I think that that can be so hard because we can be pulled in so many different directions and you can have five different things happening and someone comes to talk to you or someone comes to report something to you or, and you have to really be intentional about giving them the space they need and giving them the space to, to air their grievance or tell you what's happening. You know, I, I.
tell students and teachers all the time, know, thank you for coming to me. I really validate your feelings or you know, what's going on. And I just want them to, you know, I hope that I have built enough trust in them that they trust me to say, thank you. Let me take this burden on, you know, let me take this on now. Let me do it so that you don't have to worry about it. And I'll let you know, you know, when we have a resolution or what happens. So I think that the biggest thing is listening.
giving them the right, you know, in the mindset of letting them know that I will find a solution, I will figure this out. And then, you know, and that comes with having that relationship. You know, it takes a while to build that, I think, but you hope that you are, you know, reliable enough that you have not, you know, burned them in the past or whatever, that, you know, you have enough follow through, that they trust you to handle it and take care of those things. Right? The biggest thing is to not, we don't need to tell them, you know, hey,
calm down, this is not the right, you're not thinking about this correctly. It doesn't help to say that. I think the best thing to say is, okay, thank you so much. I hear what you're saying. Will you let me, do you trust me? Let me take care of it. Will you let me be the person that handles it? And if they say yes, then I think you just add that to your to-do list and the things you do and then make sure you follow up with that person. But I think it's important to listen and it's important to validate why it's important to them.
The choir teacher has to pass out. You know, they were so worried because their delivery for their cookie dough fundraisers is coming at two o'clock today and we had to have a plan to have our going to distribute the cookie dough. You know, and it's like to them, it's it's it's has to be done right now during their plan period. I said, let me handle it. I'll make the plan for you. I'll take care of it. I'll let you know what the plan is. I'll communicate that to the staff and we'll go from there. You know, and that just OK, they can take a breath now. So I that's important to listen, validate and then.
Robert Cave (18:57.238)
have follow through when you solve their issue.
Rick Sola (19:00.585)
You know, one piece that wasn't included in the question is the parent angle as well. You sometimes we get those calls from parents and it's a it's an urgent matter or you get the message like so and so need you to call back immediately and you hear it. And thankfully, maybe it's not as big of a deal, but for them, it's still gigantic. How how often have you find it that it occurs often that you just have to listen and by the time
especially a parent, by the time they get to the end of their, whether it's venting or sharing, it feels better and it's almost resolved itself just by being that listening ear. I see a lot of nodding heads, but Robert, have you found that?
Robert Cave (19:42.936)
Yeah, that's exactly right, Rick. I've really found that to be the case. A lot of times they just want someone to talk to, someone just to listen, to say, here's the issue I'm having. And a lot of times it's just, it's not even having a solution. Sometimes it's just, thank you so much for sharing. You know, we will work on getting better or thank you for sharing. Let me take care of this or, you know, here's what we're going to do about this. Here's our protocols. Here are the things that we're going to do.
So think a lot of times I think you're exactly right. They just want someone to listen to, like I said before, I repeat it a lot, but validate their feelings and understand where they're coming from. And sometimes you have to let them know, will get, know, here's the kind of the process we're going to go through to do this. might not be on your time, but here's the steps that we have to take. But I think you're right. Almost, I would say, you know, 85, 90 % of the time, once you have that discussion, by the end of the discussion, they feel better.
They are not as in a rush to get things accomplished as they were to start. So I think that is very important, especially when comes to those parents and those stakeholders.
Rick Sola (20:48.423)
One thing I've learned is when I get the email from a parent that demands a meeting ASAP that day, but let me know a time available, all those things. I never respond to the email. pick up the phone and 90 % of the time the phone call takes care of it and there's, there's no need for a meeting. And I find that to be helpful. But I have kind of discovered that there's
TR Travis Rogers (20:56.431)
and
Midge Simmons (21:06.519)
Thank
Rick Sola (21:15.145)
You just never know when people hear information. Sometimes it's an immediate respond, email or whatever. So yeah, that listening piece is critical.
Robert Cave (21:23.564)
Yeah. And that's something I would say to the cohort to listening is, is prepared just to be a conversationalist prepared. I always prefer making a phone call now. I would much rather call a parent than email a parent. I just like having those phone calls. And I think that, you know, I think it tones down whatever vitriol they may have, or that is coming through in the email when you reach out to them. So I would say, and I think parents really appreciate that too, you know, the time you're taking.
So I would say anytime you have a parent that's demanding a meeting with those sorts of things, I think Rick, you're, you hit the nail on the head, call them and just say, Hey, I just want to respond to what you're saying. And half the time they might still want to meeting. And a lot of the times you're going to say, thank you so much. And, know, I'll get back to you, you know, through email or whatever, if I can, when we solve the solution, the problem. But I think you're exactly right. Just prepare yourself to be making parent phone calls and be getting comfortable with making parent phone calls. You know, I tell, I tell my teachers, my counselors all the time.
Rick Sola (22:18.145)
Yeah.
Robert Cave (22:22.016)
If you need me to call someone, let me know. I will reach out. And that's just a big part of our job, I think.
Rick Sola (22:26.796)
Yeah, it's so much more efficient, I think too. It takes me a while. I, you know, I'm going to craft an email that I want to be really thoughtful about. And by the time I'm, you know, half an hour into it, perhaps. So, uh, Travis, I'm going to go to you here, uh, a little change of subject, but, also not a very pleasant part of administration perhaps, but how do you handle, uh, both practically and mentally and emotionally.
Robert Cave (22:28.866)
Yes, 100%.
Robert Cave (22:36.844)
Yep. Absolutely.
Rick Sola (22:54.44)
issues that pop up that escalate so quickly and they end up in the news. Whether it's handled correctly or not, in your control or not, how do you handle that as a building principle?
TR Travis Rogers (23:06.908)
The first tip I got is just take a deep breath.
And so anytime an emergency happens or a situation takes place, people are going to look at you, how you react, how you respond, your demeanor, you know, just the steps that you take. And so it's very important that you got to take a deep breath and stay calm. And truly the reality is, is we, whether you have a good crisis plan team, you got the communication set up, you're never fully going to
to be prepared for every emergency. And so you got to have the practice in place. That's why we have drills. That's why we have the communication chains. And then you got to be mindful of, you got to be transparent, but then you have to filter what you can say and what you should not say at that time. so emotionally, I mean, you got to take care of yourself. You got to reflect. I think it's very important to reflect whenever something happens.
what went well, what did not. We have found great value here at South that when a situation happens and it could involve like the police, teachers are still teaching and the kids are still in the classroom. And so we have found great value in, you know, social media is a rapid fire. And so sometimes it's not the truth or the right information. And so my staff really does appreciate if we have something big that pops off.
Hey guys, we're gonna have an optional staff debrief after school if you want to attend that is great And usually that kind of calms things down To where they hear it from me that these are the truth. This is what happens This is what we're investigating and so on and then as a principle You just have to be mindful of social media after the fact or if it hit the news Could be the truth it could not be very mindful of the comments if you're sitting at home at night and you're scrolling through all the comments
TR Travis Rogers (25:09.905)
and you know what the truth is and it's not, to me that doesn't tie into your mental health and so you got to be really careful of that.
Rick Sola (25:20.012)
How would you say for any of you, you've evolved over the time of being a principal, know, Travis referenced inaccurate information and perhaps it's critical of you or it's critical of the building or critical of a teacher and you know it's not accurate, but there's also only so much that we are allowed to share. Has that, is that something that you talk about having thick skin? Would you just?
put it up as over time you get thicker skin or is there something you intentionally do to really kind of help with that or things that you have found a strategy to say what you can say that kind of like Travis said earlier, you know, putting minds at ease.
Midge Simmons (26:04.2)
I'll start it. For me, like when Robert talked about...
social media or you you talked about, know, picking up the phone and calling the parent. We had that discussion. I was thinking in my mind, I do that same thing when I find out things are on social media, too. If something's being said out there that's incorrect information and I know who's saying it, I'll pick up the phone and call that parent and and just say, hey, I saw your post. I just wanted to clarify with you, you know, and have that conversation about it. And it usually that post will end up being deleted. And I think that's just to
make parents aware that you're mindful of this and you know that it's out there and you want to address it. Nine times out of ten, I'm finding out that people are receptive to that. But in a case of what Travis is talking about, if it's a crisis situation, that's a little bit different. For me, I also...
just to kind of piggy bank a little bit on Travis, to me when I read that question of yours, Rick, the first thing I thought of was you always go back to your policies and you gotta know your policies. So when you're in that heat of the moment and what can you say or not say, to me it just always goes back to that or what you say later on, right? Because if it's a...
If it's a newsworthy situation, it's probably something that's going to be ongoing. You're not going to deal with it for just that day. But just knowing what you can and can't do and backing yourself with your board policies or anything. I don't know. That's enough for me. Maybe somebody else can comment more about what Rick asked.
Rick Sola (27:43.66)
Heh.
Jenny Woolever (27:47.517)
Yeah, well, Midge, I agree with you too, is that the same concept like Robert was talking about, about listening, doing the same thing under a crisis as well, that allowing them to express how they're feeling, but also, now, these are our policies, this is what we have to follow, this is what I'm doing. Sometimes telling them the active plan that we have, and I may not be able to share what's happening with the other student, I may not be able to share this, but I know it, I'm on it.
and just reassuring them that way. I've done a lot of that too because just checking in with them and letting them know you received the message, you are aware of this issue, and you're handling it.
Rick Sola (28:25.3)
Yeah. Well, always, and there's no situation like that that is a cookie cutter from a previous situation. So I always keep any communications I put out. have a whole, whole file of them, but they're, they're never just copy and paste into a new situation. You can reference them, but there's everything so nuanced along the way.
Midge Simmons (28:47.903)
But yes, Rick, you have a thicker skin after so many years. 19 of them. Yeah, my skin's little thick.
Rick Sola (28:57.046)
And I think some of that comes with confidence too. You you think back to your first couple of years and a lot, a lot of questioning of, don't know, did I make the wrong decision here? If things are blowing up with experience, you start to have a lot more confidence. And I think that helps with the thick skin. So Jenny, I'm going to, I'm going to go to you here. There are so many to do's on a principal's list, on an administrator's list.
Midge Simmons (28:59.349)
Yes. yeah.
TR Travis Rogers (29:00.865)
sure.
Catch Part 2 of this episode on the next Cool Coffee episode drop.
