Ep 107 — Keeping Good Teachers is Simple with co-authors Jessica Holloway and Carrie Bishop

Teacher retention gets blamed on pay, policies, and “kids these days” but the truth we keep hearing is simpler and harder: people stay where they feel trusted, heard, and valued. We sit down with Jessica Holloway and Carrie Bishop, co-authors of Make Your School Irresistible: The Secret to Attracting and Retaining Great Teachers, to unpack what actually makes educators commit to a school and what makes them quietly start planning their exit.

We talk about the culture signals leaders send every day, from whether teacher voice is real to whether the workload feels sustainable. Jessica and Carrie share what surfaced in their conversations and surveys with educators: trust and value drive retention, while powerlessness, disconnection, and a lack of growth drive turnover. We also dig into the practical side: how to build simple systems that outlast any one leader, how social media and community events can support teacher recruiting, and why clear school identity helps the right people find you.

We explore the Invite, Invest, Inspire framework as a “teacher lifecycle” approach: invite the right-fit candidates with honest messaging, invest through strong onboarding and mentoring, and inspire educators to keep growing with purpose. If you’re facing staffing shortages, we also cover what to do when you have to hire quickly and how to help new teachers succeed without burning out.

Subscribe for more minimalist leadership and teaching strategies, share this episode with a school leader you trust, and leave a review so more educators can find the show. What’s one thing your school could change tomorrow to help great teachers stay?

Socials: @hollowayreader and @cbishop73

Other publications by Jessica and Carrie: 

• https://www.ascd.org/el/articles/why-good-teachers-leave
• https://www.ascd.org/blogs/4-ways-school-leaders-can-show-up-for-their-staff

This episode is sponsored by Plan Z Education Services. 

Transcript

SPEAKER_01 0:16

Welcome to the Minimalist Educator podcast, where the focus is on a less is more approach to education. Join your hosts, Christine Arnold and Tammy Musiowski, authors of The Minimalist Teacher and your school leadership edit, a minimalist approach to rethinking your school ecosystem. Each week, as they explore practical ways to simplify your work, sharpen your focus, and amplify what matters most so you can teach and lead with greater clarity, purpose, and joy.

SPEAKER_02 0:46

In this week's episode of the podcast, we are joined by Jessica and Carrie, who are co-authors of the book Make Your School Irresistible: The Secret to Attracting and Retaining Great Teachers. They're talking to us about all things teacher retention, and their pair-out pointer is Use the People in the Building to create an irresistible culture. Jessica Holloway is an instructional coach focusing on creative and innovative practices that provide transformative learning experiences for students. She's a 2019 ASCD Emerging Leader and a 2024 Google for Education certified innovator. Carrie Bishop currently serves as head of school at Point Christian Academy, a classical Christian School in Chattanooga, Tennessee. Previously, she served as an academic lead supporting school leadership teams at 19 schools serving students in grades K to 12 and as a school-based instructional coach.

SPEAKER_03 1:40

Welcome everyone to this week's episode of the Minimalist Educator Podcast. Christine and I are excited to talk to Jessica Holloway and Carrie Bishop today. They are co-authors of the book Make Your School Irresistible: The Secret to Attracting Entertaining Great Teachers. And it's super fun to have another set of co-authors on the show. So obviously, we're going to be asking you a little bit about that process too. But welcome to the show, Jess and Carrie. It's nice to see you.

SPEAKER_00 2:10

Thank you. Thank you so much for having us, Tammy. Yeah, we're excited to have a conversation this morning. Yeah.

SPEAKER_03 2:18

Okay. So of course, there's like always so many questions that we want to ask you. But let's start with maybe how did the two of you determine your writing partnership? So, like, how did you know each other and how did you determine this was the thing that you were going to write about? Loaded question. First thing. Jess, you want to start?

SPEAKER_04 2:41

Sure. Carrie and I have known each other for a while. First as colleagues at a middle school. Well, actually, I think I first started as a parent of your oldest. Yes, because she rescued me on parent teacher night when I ran out of copies. And I'll never forget. I was like, dear in the headlights. And she was like, Do you need copies? I know how to make copies. I'm a teacher. I was like, oh, yes, yes, I need copies. I don't know. It was, yeah, she saved me. I remember that. But I was first, I was her daughter's teacher. And then she came up from elementary school to teach at the middle school with me for a few years. We were colleagues in the ELA department. And then I moved into the coaching role there at the school. So I was her coach. And she taught my oldest when he got to the school. And then we have like developed a friendship over time. And then as we moved into different roles, I ended up being the coach while your daughter, her second daughter, was at the school. And then when she was out of middle school as a coach, my middle child was over there. So like we've taught or supported each other's kids in education, but also as colleagues and as friends. So that has just kind of kept us connected. And then, you know, as one of those we have a voice and we hear a lot of things being in a coaching role. And we have these conversations because Carrie and I kind of we're we're each other's safe space. So we have lots of conversations about, you know, the success and struggles of coaching roles. And we just kind of felt like there's a lot of things to be shared that sometimes isn't shared just because of either trust or opportunity. And so there were things that we were privy to that we felt like needed to be shared with the broader audience to give teachers a voice, also to give leadership some insight into some things that may or may not be happening in their schools and give them some thoughts about it. So I kind of asked Carrie if she was willing to go on this journey with me. And she reluctantly was like, sure, we'll see where this goes. Do you want to add anything to that, Carrie? Because I don't know if that really captures the whole spirit of your response.

SPEAKER_00 5:07

I mean, I think, yes, you hit on a lot of it. I think it was definitely Jessica's desire to write a book. And so she kind of had the vision and was like, I want to write a book. And I was like, Well, that sounds neat. Good. I I will support you. And I think I have had some crazy experiences. So I had some stories that I think she was like, well, I kind of want some of your stories in the book. I will say what really led me to say yes was that I care very much about people and relationships. And if I can do anything to help a leader more effectively shepherd the people in their care, if I can do anything to help a teacher have a better experience or for children and families to be better served, I'm definitely here for it, whether that's writing a book or anything else for that matter. So that was kind of what won me over.

Why Teachers Stay Or Leave

SPEAKER_02 6:05

I love that you were so very much a part of each other's community before you even started on the writing journey together. That's really special. So I love the idea, the premise of this book, like making your school irresistible, teach retention. It's such a really cool idea. Can you tell us a little bit about what you've discovered about what makes people stay versus what makes people leave?

SPEAKER_00 6:30

Well, I think that's definitely something we wanted to address in our book in an actionable way. We wanted to equip school leaders with strategies that are things that they can do that don't cost more money and that don't involve things that are outside of their realm of control or influence. And so honestly, I think that when teachers feel seen and heard and valued, I think when we listen to them, when they believe they have voice, when they can see themselves as part of a greater purpose, I think that leads them to say, I think that we do have to provide a work-life balance that they see as sustainable. And some of that comes from listening and figuring out what are the things that we need to change, what are the systems and structures that I have the ability to influence or change and how can I how can I do that in a way that still provides the excellence that I'm desiring. But I think when people stay, it's because they feel connected with their team and their leader and they're part of something and they want to continue being part of that. And when they leave, honestly, it's often as simple as I don't feel I don't feel connected here anymore. I don't feel like I want to continue investing. I'll let Jessica build on that thought. Mine's pretty simple.

SPEAKER_04 7:58

Yes, and I think that I think that rings true in conversations that we've had and we surveyed educators for an article that we wrote that specifically said what makes you want to stay and what makes you want to leave. And a lot of it on the stay piece was trust. Like, do they feel like they're trusted to do their job? And do they feel valued? Like those are the two, they might have said it in different words, but those were the two recurring responses. And as far as leaving, a lot of it was they no longer felt like they had a voice. So they were kind of felt powerless and didn't really have a place, kind of going back to that connected piece. Or they didn't see an opportunity for growth. And so they felt like they had to leave in order to move forward in their career.

Invite Invest Inspire Framework

SPEAKER_03 8:49

Yeah, that's really interesting, but also like not surprising, right? Like just kind of we all have a ton of years behind us in education, and I don't think I've ever heard anyone say they've left teaching because of the children. Honestly. Something that you two wrote about in this book was some three components to uh recruitment and retention. And we love some alliteration. And so you you two chose invite, invest, and inspire. So how did you land on those as your kind of big three ideas to recruit and retain teachers?

SPEAKER_04 9:44

So as we were talking out all the things that we wanted to say, we were kind of trying to figure out how to organize all of our thoughts. We're like, there's all the thoughts. How does this come together? And as we talked it out, it kind of ended up being like a life cycle of a teacher experience at a school. So, first, how do you invite them in and want them to be at your school? When you have them at your school, how do you invest in them? And then whether they're at your school or leaving to continue their journey, how do you inspire them to keep going?

Systems That Support Retention

SPEAKER_02 10:20

I'm just wondering, because we've been talking about, you know, the individual teachers about whether they feel seen and valued and and have a voice and things like that. I'm wondering whether you feel systems play into this as well. Like is it is it an individual thing or is it more a bigger systemic thing that goes on? And if if there are systems that play into it, what sort of systems are instrumental either in retaining or losing teachers?

Identity Fit And Honest Recruiting

SPEAKER_00 10:50

I definitely think we always rise or fall to the level of our systems. So we've talked a lot about even in our current roles and in previous roles, always wanting to put in place systems and structures so that the work will transition. It's not person-dependent. So we we definitely would would fall on that side of things. But I think there are systems you can put in place in terms of inviting people in to your school. And every day that you get up and speak, whether it's some sort of an event at your child's at your school that you're a part of, you can invite people there. There are probably parents there, grandparents there who are educators who they may know someone that wants to be at your school, or they themselves may one day decide they want to apply if you have an open position. So I think it is a mindset, but it's also there are systems you can put in place as far as attending teacher recruitment fairs. What are you putting on social media? And I think once you can get a system going and have some sort of like predictable cadence, then that becomes a lever that can be used by the next person who serves in your role, whatever that role is, whether it's a formal role or an informal role. I think I really do love a good system. And that's why we try to come up with actionable steps in our book. These are things you can put in place that can become the way we do things at blank school. And once that happens, it's like, well, this is a thing. This is a thing we do. And it doesn't really matter who does it, but once we know we've all seen it done well, it's easy to replicate. Because I do think it's important for teachers to see, to feel seen and heard and valued. But I do think systems can be in place that facilitate that. And when those systems are absent, you can feel their absence for sure.

SPEAKER_03 12:46

This makes me think about the piece where you you write about school identity. So how school's identity can really, I mean, social media helps with that, right? Like it helps relay your message to people. So how do you how did you see that or how did you through the the surveys that you did see that come out in some of the responses? Like, was that a big element where people were really invested in like this school really stands for this, and I really understand who they are versus like I'm not really sure what this school is about. What was that like?

SPEAKER_04 13:26

Yeah, I think it was it was clear in some of the responses that you know, passionate about supporting English language learners. And this is a school that was going to give me that opportunity and had support for that. So that's why I wanted to work at that school. Or this school had a focus in performing arts. And while I may not be a dance teacher, I am an English language arts teacher, and I want to give my students opportunities to perform poetry. And so this felt like a place where I could pursue that. And also the flip side of that, there were people that said, I thought this school was this. And when I got there, I realized that it's not what the school was, and I needed to leave because it was not a place where I was going to fit. And they almost almost virused remorse, I guess is what you could say, because they didn't feel like what they were told the school focused on and was about ended up being true. And so I think the clearer you are on what your priorities are, what your values are, what you're committed to do, will attract the right people. And sometimes we think this is the person we want. And so we try to sell it to them that this is the school they want to be at when you need to stop trying to like fit somebody else and know exactly who you are as a school and attract those people in that are gonna see the same vision and want to do the work that you're doing at your school. And it is an applicant's world out there, they have all the choices. And so I get the pressure to want to, you know, put yourself and say, here's where we do this for you, and this is what it is. But if you can't follow through on that, you're gonna end up losing them and then maybe even them walking away with a bad experience, and then they're gonna talk about that. So it's almost better to not even have hire them and just say that wasn't the right fit versus, oh, I worked there and this is not at all what it was supposed to be, and then have this bad narrative that's out there. So I I do think it helps you really know what you're about as as a school and then be able to communicate that, even if it makes recruiting teachers a little bit more difficult.

When Location Limits Choices

SPEAKER_02 15:54

I'm just wondering whether you came across any instances of people who like it's the only school option nearby. Like this is the only school in my area, this is the only school that speaks the language I speak, you know, something like that. Did that come up?

SPEAKER_00 16:10

We did interview, I know of one, I can think of one that we interviewed who there was really only one high school in their community, and she taught there for a long, long time. She did retire early when there was a leadership change, but she talked about some really happy years there and how close the faculty was and how it was a sense of family. And then her choice to retire at a relatively young age was or did stem from some changes that she just couldn't really uh feel like she wanted to support and be a part of anymore. And so I think that disenfranchised sort of feeling, I would say at the heart of it, when you read her uh interview, is a feeling that at one time she had voice and she was listened to. And then once she felt she no longer was listened to, that she no longer wanted to be a part of things. And I just think, again, I'm now serving in a head of school position. So I can I can say, I think it's with you have so much coming at you, so many decisions, so much to accomplish, but it is so important to slow down and listen. And if a teacher comes and shows up at your door and wants to tell you something, like really listen and really listen to what's being said, but then really listen to the maybe the bigger, like what's not being said, and the fact that someone took their planning time to come make sure they found you and maybe just be sure that people feel heard and follow up if you have questions, because that listening when you're busy and you have so much you're trying to do, it can be just so important as a leader. I I can't emphasize that enough.

SPEAKER_04 18:05

And I'll onto that back to the beginning thoughts about only in a certain location. We also know and have talked to people who are willing to drive to be at a place where they feel valued and where the they're in line with the vision of the school, and we're talking an hour one way. They're willing to do that because they they are happy and fulfilled, and that's where they want to be. So I think again, going back to like if you know exactly who you are, people will drive an hour one way to come work for you and work towards that vision that you have for your school. So it, you know, you could say if you do it right, the drive isn't an issue, the location isn't the issue. For some people it is. Some people you can't, they're just not willing or able to drive an hour to the other place. But for some it is.

Onboarding Mentors And Shared Practices

SPEAKER_03 19:00

I would think too, yeah, that's such an important point to make because sometimes that hour drive is someone's decompression time or just alone time to process. And so, you know, that's like a non-issue for people. I'm wondering about, and I don't know how how how you might respond to this because it's I feel like we're at this point in education, and I feel like we've kind of been at this point for a long time where there just isn't enough teachers to fill places. So sometimes schools will just hire people because they're bodies to have in spots and they need adults. And so how then what something schools could do that, you know, you have these all these new teachers, let's say, who've just graduated from a program and you got to make them fit into your building because perhaps they just didn't have a choice. They just needed a job, they had to fill spaces. So, what would you like if when working with schools or talking with school leadership, what direction would you point them to make sure that things work out?

SPEAKER_00 20:16

I think that falls under the investing and the onboarding process and making sure it always starts with like our core values, our mission. Let's make sure that we clearly understand what that looks like when we live it out day to day, but it's also making sure that they have access to the resources, the mentor that they need. There's so many questions. Whether you're a novice teacher or a veteran teacher, when you join a new faculty, you're gonna have a lot of questions about where do I put this? How do we do this? Even at my school, as we this year had some people join our faculty, calibrating around, you know, how we provide feedback on specific things. There's a lot of things that have to be considered. I still constantly am providing, you know, support around how we communicate with parents. And no matter how long you've been doing this, there's I think we're all better collectively than anybody in isolation. And that's where having those systems and structures in place can really pay off big time in terms of onboarding and assimilating people into your team. So I think that's true in any field. I think it's essential in education.

SPEAKER_02 21:34

I think we're just about at a point where we need to wrap up. And we definitely want to hear one last thing from both of you. We love to wrap up with a pair down pointer. So one little tip or strategy from each of you about how we can streamline things, make life a little bit easier.

SPEAKER_04 21:53

One thing that we've come back to a lot here recently is prioritize. The people that you have to solve problems. And when you do that, you realize oftentimes the solutions to your problems are already in your building. You just have to get the right voices in the room in order to develop the solutions. And sometimes the solutions don't cost anything. They're restructuring something, changing something, adding something in. And so, you know, that also when you prioritize the people who aren't directly involved or impacted by whatever problem you're trying to solve, it also ensures that they have a voice, that they're valued, that they feel trusted to help solve this problem. And then there's a shared ownership in it, you know, going through the iterations of did it work? Yes or no, let's try something else. And they'll walk through that journey with you if they're part of it, versus, well, boss, it didn't work. What's your next solution? You know, and so if you prioritize the people you have to help you solve problems, oftentimes you are more successful and it's more sustainable.

SPEAKER_00 23:09

Um mine's pretty simple. I would just say when we talk about making your school irresistible, what we're really talking about is the culture that you create. We talked a little bit about identity, but we know that culture each strategy for breakfast. And the reality is that you're building a culture. And as a school leader or even as a teacher who has influence, I mean, you get to decide what kind of teammate you're gonna be. We each get to have a hand in shaping culture. That is not something that someone who has a certain leadership role does. That's something we do together. We build a culture, and that's a big part of when we talk about identity. I think that's something that is extremely important and is going to determine whether people that you invite choose to join your team and whether people uh choose to stay.

SPEAKER_03 24:01

Those are powerful points. Thank you so much, ladies. It was so great to chat with you about your book. It's one that every school leader needs, and so they can find it in all the spots, and your links are in the show notes so people can find you if they want to grab that book. Thank you so much for being with us today. Thank you.

SPEAKER_02 24:27

This episode is sponsored by Plan Z Education Services, supporting educators with forward-thinking professional learning that puts both student impact and teacher wellness at the center. Driven by a vision to teach less, impact more, they help educators find purpose, prioritize what matters, and simplify their practice. Learn more at planzededucation.com.

SPEAKER_01 24:51

Thank you for listening to the Minimalist Educator Podcast. Join Christine and Tammy and guests again next time for more conversations about how to simplify and clarify the responsibilities and tasks in your role. If today's episode helped you rethink, reimagine, reduce, or realign something in your practice, share it in a comment or with a colleague. For resources and updates, visit planzeducation.com and subscribe to receive weekly emails. Until next time, keep it simple and stay intentional.