Episode 303: Facing the Storm - Leadership, Loss, and the Power to Overcome with Craig Woodall

Darrin Peppard (00:00)

All right, everybody, welcome into episode 303 of the Leading Into Leadership Podcast. You know, there's something I've learned over my many years as a school leader and now as a leadership coach. And that is every single person we encounter is carrying something. Sometimes we know what it is, and sometimes we don't have a clue. And that includes us as leaders. We all face storms in our lives, some are professional.

Some are deeply personal, and some are so significant that they change who we are, how we see the world, and ultimately how we lead. My guest today knows that better than most. Now, before we jump into this incredible conversation, I want to take a quick moment to thank the partners who helped make the Leaning Into Leadership Podcast possible. First, a big thank you to our friends at Hey Tutor. One of the things that I talk about

hear all the time is creating the conditions where students and teachers can do their very best work. And sometimes that means making sure students have access to additional support when they need it the most. That's exactly where Hey Tutor comes in. Hey Tutor partners with schools and districts to provide high impact in-person tutoring in literacy and math, helping students build confidence, strengthen essential skills, and experience greater academic success.

And what I appreciate about their approach is that they're working alongside schools and classroom teachers, providing targeted support that complements the important work already happening in our classrooms. If you're looking for ways to provide additional support for your students, I encourage you to check out my friends at HeyTutor. Go to heytutor.com or hit the show notes link. That'll let them know they heard about them here on the Leaning Into Leadership Podcast.

And I also want to thank our partners at the Curriculum Leadership Institute, or CLI. Now, this is an organization I know personally because I've worked with CLI both as a high school principal and as a superintendent. And one of the things that I really appreciate about their work is that they're not coming into your district with some one size fits all curriculum solution. They're coming alongside your leadership team, building relationships.

understanding your district's needs and helping you create a curriculum system that brings clarity and alignment to the work of teaching and learning. And they don't just help you build the system and walk away. They stay connected, helping your team through implementation so that the work actually becomes part of how you operate. That kind of partnership matters.

A CLI is also offering listeners of the Leaning Into Leadership Podcast a 5% discount on their first year of services when you mentioned that you heard about them here on the Leaning Into Leadership Podcast. Learn more about Curriculum Leadership Institute or CLI at CLIWeb.org. All right, let's get into today's conversation. My guest is Craig Woodall, a longtime friend of mine, a fellow University of Wyoming doctoral graduate.

And someone who spent 30 years servicing students and educators, including 12 years as the principal of Rocky Mountain High School right here in Colorado, Craig has written a remarkable book titled Overcome.

And while the book tells a deeply personal story of him losing his brother in the September 11 attacks and the grief and challenges that follow, what struck me most was how those experiences transform Craig as a person and as a leader. We talk about finding your purpose again when life knocks you down. We talk about the difference between being a leader who walks in the room and says, here I am, and the leader who walks in thinking, hey, there you are.

We also talk about something I absolutely love, the idea of facing the storm, just like the Buffalo, rather than spending our lives trying to outrun the storm. Now, this is a conversation about loss, but it's also about hope. It's about resilience, and it's about recognizing that sometimes our greatest leadership growth comes through the most difficult moments in our lives. It's a really awesome conversation and one that I am really proud to bring to you. So

Let's not waste any more time. Let's lean into leadership with my friend, Craig Woodall.

Darrin Peppard (00:00)

All right, everybody, welcome into the Leaning Into Leadership Podcast. real big treat today. sitting down with my friend Craig Woodall, and we're recording in person. So pretty awesome thing, Craig. Thanks so much for joining me. Yeah, thanks so much for having me. Yeah, of course. You know, we've been going back and forth about this one a handful of times. So glad we finally get a chance to sit down and do this. So full disclosure, folks, I will tell you that I've known Craig for

Man, a handful of years. we went through our doctorate programs together at the University of Wyoming. stayed in contact, you know, since then. but maybe instead of me telling people about you, maybe I don't know, give them a little insight into who Craig is. Sure. So retired a year ago after 30 years in public education, all at the high school level. 26 of them out here in Colorado, last 12 as principal at Rocky Mountain High School.

Now I'm kind of in your world trying to figure out speaking, coaching and and and writing and all those kind of things. So yeah, we'll see what the next step is for me. Yeah, absolutely. So what we're gonna talk about today, but we'll see just where our conversation actually takes us. But Craig does have a new book out titled Overcome. And man, this is a super, super powerful story. certainly I've seen your TED talk. We'll actually put a link to your TED talk down in the show notes so people can check that out.

talk a little bit maybe about how how someone who's a high school principal retires and decides hey I'm gonna write a book, but this isn't here's how to go be a a principal, here's how to do this, that, or the other thing. This is a completely different direction. So maybe take us to the origin story

So it was interesting because when I knew I had a few years left in my principal role, I started pondering a leadership book and started writing up little anecdotes, little things, and assumed that's what I would do. And the plan was when I was done, I would write a leadership book. And about a year before I retired, I just sat down one day and wrote a bunch of stories about 9-11, about my brother, about everything since then.

And it was about a hundred pages just of story. And I and I thought maybe that's all it was going to be. Maybe something to hand to my kids. And I'm like, you know what? Let me send this to a publisher and see. And they were very they said it was average. There was no personal feeling to it. It was just story. And so I'm like, I don't think I have anything here. So when I actually retired, I sat down and write the leadership book and my hands literally just were like, Nope, you've got another story to tell. And so

I wor I dug in a little bit on those hundred pages and just kind of put in some personal feelers and contacted another company and they said more of that, more of your childhood, more of your parents, more of all your relationship with your brother, and build that out. And then that's what took its form into what it is now. So it's much more memoir-y than I intended. I thought it would just be here's the story, but they for good reason pushed me in another direction than I'm pleased with.

How it landed, but yeah, the goal was a leadership book. Yeah. Well, that's where I ended up. But but in many ways, this is still very much a leadership book. True. there's there's some pieces in there about how and and really the book is about you, not so much about yes, there's there's the history of your brother, the losing your brother in you know with with 9-11, there, you know, in the Twin Towers, but there's this.

You overcoming your grief, you kind of making your way through that journey of losing someone so close to you and just finding a way to I guess regain some of your mental health, your focus, you know, just showing up a little bit differently. I know in your TED talk, you talk about very much the

story of the buffalo and and turning and facing into the the storm as opposed to you know running away from it. So and I know this certainly some of that is in here too. maybe maybe kind of take let let's maybe even go back a little bit and and in as as much or as little as you want to share, maybe you know, that story from nine eleven, but then how that kind of that grief kind of overtook you.

Right. So it was I mean a life-changing day in a in a lot of ways. And I soon realized I didn't have the capacity, I didn't have the margin to deal with it and be a dad. I had an eight-week-old daughter, and be a husband, and teach, and coach, and b I just I didn't have it all. And so I would compartmentalize different things, and usually we got pushed to the side was any kind of grief or dealing with that, and so

It was a a long journey of avoidance of just trying to I I I didn't know how to grieve. I'd lost a lot of people as a as a teenager and didn't just push that down. And so all that came back up and literally was a moment in time walking across the parking lot to bait to baseball practice where it hit me like enough. Like pick your head up. You're not defeated. It's time to get to work. And I was like, Wow, you're right. I just I am spiraling out of control.

If I don't fix this, if I don't write the ship. And that's when I decided to completely just shift my whole morning routine and start taking better care of myself and start digging into this grief, learning about grief, learning about myself, praying, reading, exercising, all those things just alone did nothing. But together, day after day after day after day, had an enormous impact on on me. And it certainly

Gone through grief knows it's like this. You know, it wasn't I was fixed, but it really it helped me build the capacity to carry what I was handed, whereas so I thought you just had to forget. What's unique about this, too, is about six years after my dad died, and he died largely from alcoholism, which was intensified after losing his son on 9 11. So they were connected in my mind.

And so he certainly was only 64. He would have lived much longer, I think, without 9-11. So once I felt like I was back on my feet a little bit, then my dad's in the hospital and he dies, and now I'm back, you know, into my bad habits. And then a few years after that, my mom gets diagnosed with Alzheimer's. And then she, that's a whole another journey. And then she passed away. And it's kind of like, you know, I

I I know how to do this, but I'm kind of tired of having to do this. You know, it's just a lot to throw on someone's plate. But yeah, completely shape me as a leader, as a person, as a husband, as a friend, as a fat as a father, all those things were shaped tremendously by the various losses in different ways. Yeah. Well, and I think not not in any way, shape, or form to diminish those losses, but maybe if we think about and this this to me is why Overcome is such a great leadership book.

We think about the leader. I mean, you and I are both high school principals. We we went through the day to day, the you know, just the the barrages behind the scenes that you just if you've never been a high school principal, folks the best reality show there is. man, no kidding, right? but I think about the day to day leader. I mean, like right now we're sitting down, it's October, it's National Principals Month. I I just did a

blog and podcast and a whole bunch of stuff on kind of like the hidden work, that behind the scenes stuff. And I think so often for leaders, and I'm speaking really about that principal role, but I think it's so much more

All that stuff that we continue to carry, in a lot of cases, it's other people's stuff that we're carrying. And you you let a massive high school, I let a really big high school. You know, you've got you probably had three, four hundred people on your campus that you knew to varying degrees. And there were all kinds of things that you got to carry as well. So where I'm going with this is so many leaders, leaders that are listening right now, maybe they're not having to overcome.

that kind of grief, that kind of loss. But what were some things that as you made your way through all of these things, when you go through those, you know, the last handful of years at at Rocky Mountain, you still had to carry all that other stuff in addition to this. What what are some things, what are some lessons you learned that can help leaders who are just dealing with that, not only the day to day, but then all the other things that are happening in their personal

Yeah, there's two things really that I thought of was one, I this completely wrecked my purpose. I just lost it. I just lost sight of it. I lost any kind of motivation, any kind of energy. And so I had to rediscover that. And for me, I rediscovered it by leaving education for a year. And so I literally just was fed up and left and and realized there's nothing in commercial real estate for me. There's no joy in that. It's just money and like I made a mistake. I gotta get back in. And so I had to

refine my purpose and reestablish my purpose. And I think that was the main the main piece of it. The other piece I would say is you have to be able to take care of yourself because we prioritize everyone else. You know, we prioritize everything else in the building. Then it's five o'clock, everyone's gone, now you're starting to check your email and then you're on your email until eight o'clock and and you wonder why you're so tired.

And so I had to learn that and and really how to take care of myself. And it completely shifted how I was as a leader. And I think there's two kinds of leaders. There is there's either a here I am leader or a there you are leader. And I was very much raised a here I am person. My brother, my dad were here I am people, these big, larger than life. You come in, you own the room, it's about me. I'm here, let's go. That's how I was a t as a young teacher, as a young coach, even maybe a young administrator of I'm in the room.

I'm to get what I need, listen to me. And it completely shifted that and just turned it on instead of no, I'm everyone's carrying something. Yeah, I'm carrying a lot. I say that a lot. Everyone has baggage, and my baggage is heavy, but everyone has something. And this really opened my eyes to that. And so I walk into a room now and I look, who needs a connection? Who needs what? How can I support you? What do you need? Did you f hear back from that parent? Did you and if you switch to that?

There you are kind of leader instead of a here I am leader.

That changes a lot how your staff responds to you.

So I think so much of of what you talk about there is relevant in a lot of different ways, especially that getting reconnected with your purpose. You know, I I go back to the COVID pandemic and how.

Every one of us as leaders had our purpose, our belief, our dedication challenged with what we went through. no matter no matter what type of community you were in, just everything to do with leading an education during that time was was tough. For me, it was very much something that really made me question: is that what I want?

keep doing. you know, so you talk about, you know, walking away for a year, going and and and doing something different in the real estate space and then coming back. for me, obviously this is this is where where where I've gone and found my space. I think when when we reflect on those really challenging times and and many of our leaders now actually were maybe still in the classroom or something like that during the pandemic. But

I I know you had some had some thoughts on on that and how that was just another one of those things that weighed on on school leaders. You know, I was an I was an athlete and I use this analogy a lot, and anyone who's an athlete understands that there's a there's a last day for everyone in in sports, and it's usually an injury that does it. It's a career ender. And so COVID was in essence my career ender, and that I

was really not able to pick myself up out of there. I retired at the end of 2025, so I made it a couple of years limping to the finish line, but it it just I you know, I joked that it was I've never said I don't know more in my job than over those two years basically. What are we doing next week? No idea. How are we supposed to I don't know. But if a kid doesn't I don't know what to tell you. I just hey it changed again. Hey the rules changed. Hey now we're back. You can have half your kids. You can have

It was just unbelievable. But what I actually appreciated about it is when you when you go through adversity, you go through challenges, all that's left is your core and it's your foundation. And our foundation was so strong that we were able to endure that. And I would say over and over, we are in the right place to deal with this. I can't imagine what other schools other are dealing with.

'Cause they don't have this foundation. We are solid and we are together and we will be fine. I even got pushed on that it was toxic positivity. And I was like, okay, I am anything but toxic positivity. I'm a realist at best. But it's like, no, that's I'm not ignoring this. I'm just saying we have what we need to do this. And we can do this effectively. And we struggled through it like everybody, but I think maybe we climbed out of it a little bit quicker than some other places. And I think a lot of teachers

became better teachers through it and having to how do I engage these kids. If I can get a kid engaged when they're sitting in their room on a video, I can certainly do it in person. And I think in a lot of ways really challenged us as leaders too and how do we lead and and and just like how much you took for granted being able to just walk down the hall and and see a teacher or s check in on a student instead I was driving all over northern Colorado delivering medications and you know computers and Wi-Fi and

Yeah, so thanks for bringing COVID up. That was Yeah, that was that was never the intent of what we were going to talk about today. But but I I think I mean that's obviously one of the ultimate examples of us truly as leaders having to face the storm. So maybe maybe where we'll go from that is is talk a little bit more about just that philosophy of facing the storm and how as leaders, as challenging as sometimes that is

That's that's ultimately what we have to do. And well, I won't connect the dots because I have a feeling you're going to. Yeah. So just in general, the concept of the buffalo is they're one of the only animals that when a storm is coming, they literally will turn and face the storm. And the analogy that's often used is the cow that just runs away. And Colorado is a unique place because we're one of the few places that have both those animals. And most of our storms come over the mountains and

And blow through that way. And so when you think about a cow running from the storm, they could end up in Kansas, they could end up in Missouri before that storm, you know, and it's just gonna chase them that whole way where the buffalo will unite and stand together and push back on things. And so that really resonated with me with my journey of grief, but also, you know, when I think of COVID, when I think of leadership, you know, I committed to a weekly staff meeting.

during the entire part of COVID. Like we are gonna get online. I have no idea what I'm gonna tell them. I don't know the rules. I don't know what just changed, but we are gonna face this together. I didn't even have the analogy of the time, probably the buffalo, but that's literally what we did. We just banded together as a staff and we locked in and I was like, I might have 10 people. It was optional. And I would have a hundred and twenty, one hundred and thirty staff members every single week. Just what are we doing? How are we gonna get through this? What are we gonna do?

And then I'd hear other schools and other districts saying, I I haven't seen my administrators in a month. I don't know. They're just everyone's doing their own thing. I'm like, that's not how we're gonna get through this. We're gonna band together. The buffalo rarely does it alone. They band together, they lock in with the herd and they push through it together. And COVID was a great example. But that's something our school always did. And that's what I mean when I say we were we were equipped and we were ready.

To handle COVID when it when it happens simply because of our foundation was so strong. Yeah, yeah, for sure. So so let let's let's get back to the book a little bit. they have so many just really powerful stories in there. I I'm gonna ask you to maybe maybe share one of your favorites from there or or one of the ones that'll maybe resonate the most with with our audience. I have one that a chapter that is certainly one of my favorites. We've we've talked about it a little bit.

before before hitting the record button, but I want to go first because because if if my favorite is your favorite, I'm gonna push you to have a second one. So the chapter on Gitmo. the I I was not aware until until reading the book that you'd had the opportunity, and now I know you've gone multiple times to Guantanamo Bay. talk a little bit about

that and maybe just some of the things that you learned, maybe about yourself or about leadership or just anything in general. That I just think that's such a powerful chapter. Right. So it's an organization that flies down family members to sit in the courtrooms. They just think it's important that that piece of the puzzle is represented. And I've known of it for a number of years, but it's you have to commit about 10 days to go.

You have to get to DC, you fly out of Andrews Air Force Base, you're there Saturday to Saturday, and you gotta leave from DC. It's just I never had the time to do it, and also gets canceled a lot. And so once I retired, I'm like, I'm going. And so I went right away. You can take someone with you. I took my second daughter, Ryan, the first time, and the second time I took my son Nathan, and it was an incredible experience. And this will sound odd to say, but I was told that we might not even see.

the the prisoners when we were down there because it was a unique week and I was frustrated by that. I like, that's what I'm coming down to do. I want to see these men. I want to see these men that supposedly are partially responsible for 9-11 and really killing my brother. And and when I saw them it was almost joyful. It was almost invigorating. Like I accomplished I got all the way down here to a courtroom to look at Khalid Sheikh Muhammad. I never thought I'd have that experience.

And and yet I did. And so it was it was odd to describe it that way. both times I went, we had an off day and we were able to go snorkeling in Guantanamo Bay. That is a unique experience that I will be honest, that's not very good snorkeling. It's probably great fishing. They say it is, but it's not great, great snorkeling. But man, it was a full circle moment for me and

You know, you have the opportunity to sit and talk with defense lawyers and the prosecution explains everything to you as well. And we're able to sit in there and challenge them. And they're they were just both sides are represented by amazing people who are very open and and sharing things very encouraging to us. And it's it was amazing to see my own kids step up and ask questions to the defense lawyers. And you know, I had a pretty unbelievable experience on the second trip where, you know, you're behind glass.

And that you know, everyone's in front of you, and at a break, Khalid Sheikh Muhammad, the supposed mastermind of everything, stands up and he kind of just turns back, kind of looks back to see who's there, and we end up locking eyes, and neither of us budged for a while. And it was an intense 10 15 seconds that made all those trips worthwhile to be able to look in the eyes of Khalid Sheikh Muhammad, one of the most evil men on.

on the planet who has beheaded people himself and just lock eyes like hey I'm here I'm not afraid of you we we are here to represent what happened and and and hopefully that be here by the end of the trial so as far as what I'd learned about leadership and all those things boy I don't know it just told me a lot about myself and that my journey because when I I stood at I stood next to ground zero a few weeks after 9-11 and I expected tears and I was angry.

And I was someone needs to pay for this and someone and to be able to go full circle and be sitting in a courtroom with some of the people who need to pay for this and be able to lock eyes with one of them and challenge them, man, that was I'll go again, I'll go a few more times 'cause it officially they haven't even started the trial yet. That will hopefully start in in twenty twenty eight, I think, which is which is ridiculous, but yeah.

It's an incredible experience that I'm so glad there's an opportunity for us to go and do that. Yeah, absolutely. so that one's that one's one of my favorites in there. there's so much good stuff in here. What's what's something that that we haven't talked about that's in here that you'd like others to know? I think probably my favorite story to tell of that whole book is the last phone call.

So my brother and I were competitive better more than close. He was a few years older than me, we were both athletes. He was even a bigger build than me. And so it was very one-sided competition in the yard. It was not a lot of fun, to be honest. And then as we grew into adulthood, we became better friends. I had a kid first, I was married first, I bought a house first, and so some of the older brother roles shifted to me, and that

kind of culminates in, you know, a f a phone call with my brother in early September. And he was calling to tell me that they were pregnant with their first child. Him and his wife are both on the phone. And the conversation was just awesome to be able to talk about sleepless nights and diaper changes. You know, how are mom and dad as grandparents, how'd you pick names and here's what we're thinking about names. And do you think our kids will know each other? Will they be athletes? Will they be artists, musicians, all that kind of stuff?

And the only term I can think of is it was a beautiful conversation between brothers. And that's not a term that I would have used, he would have used, anyone would have used about our relationship was beautiful. And I had no idea, of course, at the time that that would be the last time I ever spoke to him. But if I had to pick a last conversation that had that, there was no better. There was, I don't think we ever had a better phone conversation in our life. Maybe even any conversation in our life. And to have that be your

Last one is a tremendous blessing. It's it's heart wrenching at the same time, but it's such a good example of how far our relationship had grown, which is amazing and also terrible in that it we lost so much of our connection that day that we had built. So yeah, that's that's probably my favorite story there. And I love this, I love the parts about each of my kids coming back on the

On the anniversaries, those are some of my favorites, and just seeing their uniqueness and their strengths come out when I'm struggling and they're picking me up. And those are some of my favorite parts too. Yeah, for sure. absolutely an incredible book, folks. we're gonna put links down in the show notes so you can get in there and check that out. again, we'll have a link in there for Craig's TED Talk that's in there. last thing here that that we'll talk about on the show, it's the Leaning Into Leadership Podcast. So

I'm gonna ask you the same question I ask everybody. how are you leaning into leadership right now? So I'm trying to completely do something new. I'm I'm trying to get it more in front of people and just encourage them with messages of hope. I'm I'm meeting with a number of principals one-on-one, just trying to use some of the wisdom I have. My wife keeps telling me you can't just walk away from the education world without the amount you've learned over 30 years. And so I'm completely

leading into leadership different than I ever had. Because I would have two years ago I would have said, I'm working on myself. I'm working on this. I'm trying to develop some future leaders maybe. Now it's a hundred percent about others. And it's giving back to others and giving them the message of hope and and helping them through adversity. How do they challenge how how are they dealing with the ch their challenges and their own storms? And so it's it's fun to be on that side of it. I really enjoy it. And I and I think I'm making a difference with some people and

That's that's another thing I hope continue. Excellent. People are gonna want to get in touch with you, they're gonna follow you on social media, that kind of stuff. What's what's the best way for them to connect? Craigwoodall.com is the website, and so that's the best place to start. It's got all the it's got the TED talk, it's got the book, it's got anything, you know, podcasts, any of those things, blogs that you wanna see on there to to find out more. Yeah, there's multiple contacts on there to click and and reach out and yeah. All right, let me know what you're dealing with too.

Perfect. Yeah, we'll get that down in the show notes. Craig, thanks so much, man. I'm I'm really proud of you. I'm proud of the the work that you've done here and just really proud to call you a friend. Thanks, man. Appreciate that.

All right, awesome conversation with Craig. I really appreciate getting the opportunity to sit down in person with him. For those of you who watch this on YouTube, obviously you could see the two of us sitting together in the same room as we recorded this podcast. It was a lot of fun to be able to do that. make sure you get connected with him, get down in the show notes and take a look at all of Craig's stuff. Get yourself a copy of Overcome. It is an absolutely fantastic book.

And while you're at it, click on the link and check out his TED Talk. With that, it's time for a Pep Talk. And today on the Pep Talk, I want to be short and sweet, and we'll see if I can actually do that. Earlier this week, those of you who listen regularly know that I am a diehard Denver Bronco fan. And something that that has been taking place over the course of this season, early in the in the season.

The Broncos offense has really struggled. They have a new offensive coordinator, and there's been all this talk that the head coach was going to take back play calling duties, which he made that decision this week, and he's going to do that. But I also saw a story about the owner of the Indianapolis Colts being down on the sidelines taking notes about what's happening during the course and the flow of a game. And it got me thinking, it got me wondering.

At what point in time as the leader do you, without realizing, overstep? Or is it perhaps a gap in communication that leads to the perception that you might overstep? The challenge for you this week is to think about those moments as a leader where perhaps you're overstepping without realizing it. Maybe have a conversation this week with one of the people that you lead and

ask.

Are there times when I overstep when I should probably just take a step back, trust the people around me, and let them do their work? So often, as leaders, that micromanaging that we don't intend to do ends up happening because, let's be honest, most of us as leaders, we have this desire for control. We feel like we need to have control. At a point in time, we all do it. We all overstep. So this week.

Get out there, see if you can find one of those places where you're overstepping, and see if you can find a way to correct that. Your people will appreciate. That will grow more trust, and it'll help you be a better leader. Hey, that's what I've got for you this week, folks. Thanks so much for joining me here on the Leading Into Leadership Podcast. As always, rate, review, subscribe, and share this podcast with someone else. Get out there, have a road to awesome week.