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#32 - Kevin Gailey: Midwest Academy, Education, Empathy, Leadership, Culture, and Vision

Kevin Gailey on Innovate Marketing

As the Head of School for Midwest Academy, and as a parent of a child with learning differences, Kevin's focus is keeping children at the center of his work. After being drawn to serve complex learners as a teacher over 25 years ago, he has developed a passion for providing progressive learning experiences to students with learning differences. Education, Empathy, and Leadership.


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And welcome to Innovate Marketing, where we are bringing you interviews with the people who are making waves in the world of marketing, branding, and business growth. I'm your host, Shawn P. Neal, and we are brought to you by MyPodcast.Media. If you're a brand and you're considering podcasting for your marketing and communications efforts, make sure you visit MyPodcast.Media.

Now we've got a great interview for you today. So without further ado, let's get into it.

I remember when I was in school, I felt like I had a really difficult time just keeping up with my peers, like keeping up with school and keeping up socially. And I never really felt understood. And then as an adult, I got a diagnosis - kind of later in life in my early forties - of ADHD.

And as I like really started to learn about ADHD and what all comes with it, my childhood started to make a lot more sense. This conversation today was really fascinating for me because I went into this wanting to dive into leadership in education. And that's where I met Kevin Gailey. He's the Head of School for Midwest Academy in Carmel, Indiana.

But it really became more interesting as I began to learn his philosophy on education and leadership and how this emotional component of understanding kids holistically. And then understanding people the same way, not just kids. So great conversation for you today. Before we get started. I want to take a minute to just let you get to know a little bit about Kevin Gailey and then we'll get into the interview


As the Head of School for Midwest Academy, and as a parent of a child with learning differences, Kevin's focus is keeping children at the center of his work. After being drawn to serve complex learners as a teacher over 25 years ago, he has developed a passion for providing progressive learning experiences to students with learning differences.

He believes that progressive education offers each student the ability to engage in their learning in a unique and fulfilling way. He enjoys spending time with his two boys, fitness, the outdoors, tinkering with tools, and reading.


So one of the things that has really fascinated me in our time of getting to know each other is your commitment to education and the emotional components that are severely needed for our kids. And I would love for you to just kind of talk a little bit about that and share, if you can, some of your thoughts on empathy and , you know, how that applies in, I guess, life and in the world of education


Our educational environment, we keep it small so that we don't make the mistake of losing the sense and losing sight of the human being. You know, when you're in a big space, it becomes harder to juggle everybody's needs. I taught second grade years ago, and I had anywhere from 9 to 14 kids at this school that I was at.

I then left, moved states, and I had 23 to 27 kids. And I tried to do the same thing with 27 that I did with 9, and it was so tiring and so exhausting and so difficult that you then think about, okay, that was before I had kids of my own. All the other trappings of life, because I was still in my late 20s, early 30s, and I was just sort of getting into houses and car payments and having kids and all those things.

Well, imagine now I'm 20 years later, and I'm with 27 kids. How worn out am I going to be? And so how do I keep doing that? And so part of our success, or secret to that, is that we keep things small at our school. And by doing so, we can see who the human being is. Now, we're still fallible; nobody does things perfect, but you also can see what's going on here. Is it the system we've developed? Is it the system the parents have developed at home? Is it what's the child choosing to do not choosing to do? What's what's going on that's causing a trouble. Let's just say that there's a challenge, but also on the positive side, things are going really, really well and a kid is fully invested - the systems at school, systems at home, they're all working. How do kids get excited and get interested in their education? How can they have ownership? How can they walk out the door at 18 years old with a sense of, "I really own who I am and own what I do?" And I think that comes in drips. You have a teacher that says, "Hey, you know what? You can choose one of these seven things" versus, " here's the one assignment that you're going to do." You know, those types of things. It makes a curriculum an eight lane highway instead of a tight rope that you have to walk. And then that humanity is built in. So positive or negative, whatever's going on, you can think of who the human being is.


Oh, it's such a good point. And, you know, I think that there is, from what I see anyway, a disconnect between. You know, parents and the educational system, there is a belief of what the educational system is supposed to be doing and then versus what they do. And I think that, to the point of what you're talking about here, is that the education system, oftentimes, you know, we have this imbalance. So I appreciate you bringing that up. Now, I know that your path to Midwest Academy has been kind of fun. Interesting. You've got a history in sports, which I think is pretty fun. Would you just kind of tell us a little bit about, you know, what put you in motion and how you ended up there at Midwest?


Sure. So I went to college and I thought I was going to get an education degree. Didn't really like the program. So changed my major, like, 3 times and ended up with a psychology degree. Clinical Counseling. And when I was at high school, I had done a 6 to 8 week project as a senior where I didn't go to class and I went and tried out different things. And I wasn't sure whether I wanted to go into counseling, teaching, or coaching. So I dabbled in all of it. So anyway, so I get this counseling degree and I work in outdoor education for a while. I work in a small college. I decided to get a Master's degree in education like that program.

(I) Go through and I'm an assistant teacher actually at the school that I graduated from as a kid and so I start this teaching degree and as I'm going along, I've always seemed to ask to do a little bit more here a little bit more there. I realize I want to get an administration degree so I do research and they're all geared towards doctorates in leadership, but to become a Superintendent in a large public school and that wasn’t going to be me and I had an interest in college athletics because I was coaching. I had coached since I was 18 years old, basketball, soccer, all kinds of different things. So I got a master's degree in Exercise and Sports Science with a concentration in Collegiate Administration from UNC Chapel Hill, worked in the athletic department, did anything and everything you could imagine.

I was on the field during games, I was working in the compliance office- just different things. So the path took me a little bit of a winding journey because then I started working in college athletics. So I worked in Indiana University, worked for the NCAA, and then while I was doing that, realized I'm not working with kids anymore.

Because I started working with kids in summer camps when I was 11 years old. And so that led me back to Midwest Academy where I thought I was going to be a volunteer, a tutor, or some sort of connection like that.

but I became an administrator in the school, counselor in the school. So it took lots of different pieces of the puzzle that I had and it put them together. And it was interesting for me because I had always had this desire to do that, but I couldn't figure out how to get there. Anything that I found in terms of opportunities, I would be doing one thing. People ask we do something else. But I never quite gelled and when I came here about two, two and a half years into my tenure here, I was asked to be the Interim Head of School and then what happened from there is all the different pieces came together.

And I was able to learn a lot more just through the experiences I had. That I even had any vision would come because that's a lot of what leadership is. Something presents itself to you and you have to make a decision as a leader, not as an individual.


Exactly. And, you know, you came in to this with someone else having been previously in this role.So, that person obviously had their own vision, their own priorities, things they were working on. And you came in with your own vision as well. And of course, one of the things that you wanted to focus on was the numbers and the enrollment. So can you talk a little bit about that for us?


So yeah, the school had vacillating enrollment. It would rise as high as 85 and drop back down into the sixties and up and down. And fortunately for me, I was here for two years under someone else while that was going on. And I was able to see the pros and cons because, without any criticism of my predecessor, you can see how things are being done and what's working and what's not any of the benefit of saying, I'll take that one.

Or I won't take that one. Or let's see if I can figure out how to prevent that thing from happening again. Which was really not under that particular leaders control, but maybe we could do some things to prevent it from happening again. So you're doing all of that. And so you're developing this experience while also you have a vision for a school based on your own experience. I had worked in progressive schools. I had worked in more traditional schools. I worked in a faith based school. And so I saw different pieces that I really wanted us to have. You also have to look at the personnel that you have. And so there were some changes necessary with personnel, but also you have to give people the opportunity to make adjustments.

So you're developing a vision. When you develop your vision, if you just start plowing forward, a huge piece that's missing from your vision is humanity. If you're so humane that you don't make any changes and you're so relationship driven that you don't accomplish tasks, you're too far on one end of a continuum.

If you just obliterate everything, throw people to the side, and don't think about those consequences, well, you're in the wrong spot there. And the reality is that you're not developing a space that meets the vision which you say you want, which is to have a foot in psychology and a foot in education so you're developing young humans.

You're not creating students who are going to be successful at getting into college. They will be successful getting into college or careers or whatever it is that they're going to do if you take that balanced approach. So the beginning for me of that vision is to figure out how to balance task and relationship and when you're out of balance, you're not going to be successful.

So, from there, the vision becomes about details of a progressive education versus traditional education, and then you're also looking at meeting the needs of the kids. Our kids need more counselors in the building than other schools. Now, other schools might not have the right ratio. If you have five counselors in a school that has 5,000 kids, you probably don't have enough counselors there. But if you have five counselors in a building that has 115 kids, you get a pretty good ratio, pretty good ratio.


That’s a good point. As you're bringing this vision, and I think one thing that I'm hearing that is incredibly resonant for me is that there is this balance of self-control that comes with leadership.

I mean, because we all know we, you know, it's easy to get in and be sucked into the moment. But to have the self control to step back, to learn, I think it's what I hear you really touching on. And then also kind of a question that forms out of that then is, you've got staff who have worked under different leadership who have supported and helped build a vision that was different than yours.

How do you start to bring people into what your future looks like and get that buy in that it takes?


Well, one of the 1st things I did was I met with every single person 1 on 1, asked about their questions or concerns relative to the transition, relative to me, relative to anything that they needed to talk about; everything was on the table and that helps with the beginning of that bridge.

I was also able to understand, this person really desperately wants to go in the direction that I would like to go in. This person is very, very hesitant because they're used to a different approach. And so I was able to understand each individual person's needs and then we were able to talk through.

But also one of the things that we did early on is we developed something that didn't exist, and that was the Midwest Academy Faculty Credo. And I wrote down in the middle of the night, laying down in bed - so writing upside down- about 20 different things that I thought mattered. It's as simple as being kind to the children, being attentive, what is it to be a good employee?

And so then I brought it to the, to the staff. And it's the faculty and staff credo, not the faculty credo, because it's kind of how I started,. But then you have to see where you expanded. And I've always had this thing where I say I'm going to do 85 percent of what I think should be done and then I'm going to come to everyone and say, this is where we are. Am I at 85 percent or more, or do I need to back it down? I'm only 70 percent of the way there. So that's what we did with the faculty credo. And that was one of the first things we really fleshed out together. And that document has become essential to anybody who's hired at our school because it says, in the name of kids, in the name of your fellow staff, in the name of parents, in the name of the institution as a whole, these are the things that we're going to do.

And so you understand the culture of the space, but also we developed it together. Some of the things that I wrote down that were taken off or the words were changed because it was like, that's not really the word that meets what we who we want to be. But then there are other places where, if there was a discussion and I said.

Nope, this has to be there because you have to be this to be here moving forward to climb the stairs that we need to climb together. And so I was able to set out expectations, but also be inclusive at the same time. And again, it comes back to balance. My grandfather, who was a very influential figure in my life, he always said everything in balance, you know.

Don't do too much or too little of this. Don't go exercise too much or exercise too little. Don't be too much of a health nut. Don't be too little. Don't drink too much. Don't let yourself not have any fun. I mean, that kind of thing. You have to find the balance. And so that's what I was looking for there: the balance of expectation with the balance of inclusion.


Well, and to your point, when you create that, because we know not 100 percent of staff, faculty, whatever your situation is, will be absolutely on board with whatever your plan is. But I think to your point, when you're creating those opportunities for people to say,”here is where I need some more from you, “or “here's where I need something changed,” you're going to get more flexibility. Is that a fair statement? More grace…’


You are, you are. And then we, you know, we talk about giving people grace. Having trust, benefit of the doubt, those kinds of things. Relationship- having a strong enough relationship with 30 staff members as a leader. It's not easy. I don't think you can do it if you have 200 staff. How do you know everybody with enough depth? But I know everybody with enough depth that I am aware of where their challenges are, and they know each other. And collaboration. But also when conflict arises, you have enough interaction that you've created enough emotional safety that you can actually have a real discussion most of the time when somebody has a conflict. It's not just the ”Professional interaction” because that really just creates a false sense of rules and a false sense of relationship so that when you do have a conflict arise, you may never really get to a true resolution. And again, it comes back around, you know, group dynamics.

Once you hit 12 people, once you rise above 12 people, you start to break down. So we have subdivisions as well. So that the subdivisions feel like they're close. There's a high school group, there's a middle and elementary group and there's a counseling group and they have their subgroups so that they have their teams and then they have representatives that are part of the leadership team.

The leadership team is about 6 people. But then I try to make connections with all and I visit all the different meetings and all of that. But all of that connectivity is how you get people as much as possible on the same page.


Yeah. So when you think about the future of education as an industry, and I hate to say industry. Education to me is so much more tied into the human component, but to use that term loosely, what excites you? What kind of things technology-wise that are emerging excite you about the future of education?


Well, I think the more technology that exists, the more that the technology is able to allow you to have information at your fingertips to be shaped and reshaped as you need to, the more you can get away from memorization.

And that means you could use information, you can analyze your research, you can discern. And that means that kids with learning differences have more and more and more of a shot at succeeding because in jobs where they have to regurgitate information, oftentimes that is not their skill. But I could be a lawyer and bring down information. I could be a lawyer who memorizes information. The reality is that the lawyer who can pull information together and develop those analytical skills,may be the one who has the learning difference. Also, may be the better lawyer 20 years in because they've worked so diligently on developing these higher level skills.

So, the kid who at 9 people thought, oh, my God, how's he going to get a high school diploma could be more successful in his career than the person who is an “A” student from 1st grade all the way through college because they're learning methodology is aligned with the current technology. I mean, that to me is pretty, pretty exciting.


You know, there are 2 things that stand out to me here. 1st of all, your use of the word differences, I think is fantastic. Because of stigma, we need to break that stigma. The other thing that I really am excited about here is the fact that you're telling people don't be afraid of what's out there, lean into it and use these as tools. And I think kids need to hear that because, yeah, I remember the days when “don't use a calculator in class. Are you going to carry one around with you for the rest of your life?” Yes, I actually am.


Yeah, you actually are. Where is it? Here's my little toy. My little toys got a calculator if I need it, right?


Exactly. And a million other things.


Yeah, absolutely. Well, you know, it's kinda comes back around to your question about leadership and all. Leadership should be situational and you should have a framework so that you have equity, that, you know, if Shawn's a great negotiator, he doesn't get $10,000 more than the guy who isn't as good at negotiation, has the exact same qualifications. But leadership is situational. And there's a great guy named Rick Lavoie who has written books on learning differences and all, and he came and did a speaking engagement here and one of the things he talked about is Fair versus Equal. And the example he used was if somebody fell down in the middle of class because they were having a heart attack and they stopped breathing. If you said, “oh, I'm sorry, I can't help you because it wouldn't be fair to everybody else.” You know, the situation calls for something different. And so the equity was that this person needed help and so you have to use that discernment and it comes back around. That's the thing that our kids can do and all kids can do. And so when you think about education, that's what we need to drive on. And these tests that we have that are regurgitating information, they tell us nothing, nothing at all. That's why a lot of people are dropping the SAT. And others, and I think more will.I think you will see over the next 10 years, by the time you get to 2030, I think the requirement for standardized tests to get into college will severely change.


Yes, I completely agree. I want to start to land the plane on the future, here. I know you and I have had conversations about where where does your future lead? What does Midwest Academy look like? If you could, just kind of future forecast a little bit for us, maybe 5 years in and and just give us some dreams, some things that you'd like to to see happen maybe for yourself personally and for Midwest as you go into the future.


So for Midwest, we are at the point where we're developing an endowment. So that endowment would be established and will have increased in size. We will have zero debt. That our building plans for this building, which are modifications to what we've already done, are complete. And the land behind us, we will own. That is actually all on target.

And then what's projected out from there. There are some other building types of things- a desire to acquire some land that's actually kind of diagonally across from us. If it still is available and if it's affordable. So all of that for Midwest Academy, but then also some things with maybe transition planning for graduates. A secondary business for them to get work experience in and we're developing a tripping program right now. We're going to take kids to Disney and see all the behind the scenes this year, which is a big trip for us. We've been to D. C. New York. We've done Alabama Civil Rights Tour. We're actually looking into Costa Rica right now.

But maybe all of those last few things are developed and interconnected. Think of kids who need a bit of a gap year but should do schooling. So maybe they're doing some school online through community college, but they're coming together several times a year. And they're doing some things like going to Costa Rica where they're rappelling down waterfalls, or they're going to Stonehenge where they're seeing these World Heritage Sites. And they're gaining all of this experience seeing the world and seeing cultures and understanding and being holistic. So then, the idea for me for the future is that I'm involved in that but also that it's promoting this sense of acceptance of others because you're seeing these other cultures.

That's what I would like to see for the world. I'd like to see myself be involved in that because there's too much conflict in the world, and it isn't necessary. It's something that oftentimes could be avoided if we had a collaborative, flexible mindset. And I'm not trying to say that all nations are going to work together perfectly and all that, but I think a lot of the conflict, especially within our nation, it's about being selfish, and it's about being one sided, and our mindset is that I'm not going to listen to you. There's a gentleman who is part of our school who has a very different view than I do on things; had very different on COVID, but it didn't matter what my view was on COVID, I was stuck- I was in a school. But his views on COVID were different, and some of his political views and all that. And we have conversations all the time and there's never a conflict because it isn't about arguing. It's about sharing “these are my thoughts. These are my ideas.” And then saying, okay, well, I can see that this is what I can see. And that's how you're going to get people to come together and you're going to prevent these future conflicts.

Things like what's going on in Ukraine. Imagine if people said, “hey, let's study the what happened in X revolution or X takeover of a country. And instead of having that conflict, let's talk about that to prevent this conflict.” Those are the things that I would hope for the future.


Yeah. And it all starts with a child in a place of education who is exposed to those opportunities to learn that way of thinking.


And being given the opportunity to learn too, because we have kids who are less than 10 years old have been taken off diploma track in public schools that end up going to college and it's because they can't handle that big space. But here they have a smaller space and they have that individualized attention and we get to know them and their acceptance and they start accepting themselves. And you just put all those pieces of the puzzle together and the ball starts rolling and it's like, think of like a tornado, but a positive tornado, right? I tried, I believed in myself, I succeeded, ooh, I'll try some more, I can believe in myself because I have more success, next thing you know, it's an upward spiral,. But it's a positive tornado whipping through the building instead of this downward decline, which is where they were heading.


Yeah. So if you will humor me, this is how I would love to wrap up our time. I remember you had shared a story, and I'll try to tie this all together, you had shared a story recently at a speaking engagement you did, talking about one of your students who had come in and you would, I believe, pass him, maybe lunchtime or something, and he was a little grumpy. A little grumpy, a little grouchy. And the reason I'm asking you to share this is because I think in the spirit of what we're talking about, every single one of us will encounter a grumpy person, and I would love if you would just share that story and how you kind of resolve that. And maybe that's something we can think about as we go forward.


Yeah. Yeah. I was walking through the hall and we have certain little pull out areas, and this 1 young man, he was in 1 of these pull out areas with his laptop. And I walked by and I kind of gave him a pat on the shoulder. And I said good morning to him.

And he said something similar to, “who asked you?” And I was like, whew! And I kind of turned and I tried to engage in a little bit of conversation and it was clear that we weren't going to have a conversation and I had to decide whether I'm going to pull the “listen, middle school child. I am the head of the school. You will respect me…” and engage in some sort of conflict. And I didn't. Instead, I found a way to step away from the conversation and make sure that it didn't escalate or anything with him. And I talked to teachers and we did a little more research and within less than a week, we realized that kid needed a snack every single day before 10 o'clock.

He was also playing hockey in the morning and he was doing cross country in the afternoon. He was burning like 8,000 calories a day, but only taking in three. So, we got him more food, and then we were able to access his abilities, and then he really connected with teachers. That one little thing of understanding him a little bit more, slowing down to understand him, then we started giving him successes, and once he believed in himself, his grades took off.

Because he wasn't doing really well in school with us either at that time. And so not only did his grades take off, they were just a reflection of him taking off as a human being. Well, he ended up going to Rose-Hulman. Graduated with honors, has a degree in bioengineering, and is starting to pursue that career.

And really it's because we had enough time to really figure out who he was as a human being.


Well, I, I appreciate the story and I appreciate in the spirit of, as you said, what a good future looks like for us. Next time we encounter that grumpy person, just remember there might be a backstory there. There might be something that we can do.


Patience, patience is a virtue that we all need to work on.


Kevin Gailey. Yeah. Thank you so much for being here. Absolutely. Enjoyed this conversation with you.


Thanks. Really enjoyed it. And, uh, look forward to seeing you again soon.


That brings us to the close of this edition of Innovate Marketing.

We're glad you tuned .Innovate Marketing is brought to you by MyPodcast.Media. MyPodcast.Media produces podcasts for brands, influencers, and nonprofits. Find us online at MyPodcast.Media. Your producer for Innovate Marketing is Beth Fried, executive producer, Shawn Neal. We'll see you next time. Be sure to tune in.

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