Episode 253: A Look Back, A Look Forward, and Trends I'm Seeing for 2026

Darrin Peppard (00:00.686)

All right, everybody, welcome into episode 253 of the Leaning Into Leadership podcast. This is the final episode of Leaning Into Leadership in 2025. And as our calendar is winding to a close, I've been thinking a lot about pausing. Now, let me explain. I'm not talking about the kind of pause where we just stop caring. I'm talking about the kind of pause where we slow down enough to reflect.

Over the last couple of weeks for me, I have been doing a little bit less of the day to day stuff at Road to Awesome and allowed myself some time to focus on a home improvement project that my wife and I have been wanting to get done for a while. Part of that project involved doing some painting and we used our airless sprayer. Now, if you've ever painted a room using an airless sprayer, you probably discovered that

That can be pretty monotonous. It can be work that doesn't require you to be 100 % mentally dialed in. It's pretty methodical. By doing that work, I found that I allowed my mind to wander.

in that pause, I was thinking back on 2025. I was thinking about so many different leaders that I've had the opportunity to work with, to support, to learn from. But I also found myself thinking about what's coming next. Where am I going in 2026? And then ultimately thinking about kind of that sweet spot in between where reflecting and projecting

are important, but living in the moment is just as important. Look, 2025 has been a very full year. I don't know about for you as a family, was unfortunately a year of loss. It was a challenging year. As a business, an extremely successful year, a year of great growth, of incredible evolution. I'm sure for you as a leader, just like me, you have...

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been faced with lots of decisions in 2025. You were met with lot of expectations. You were met with constant demands. Demands on your time. Demands on your presence. Demands on your thinking. And if you're listening to this as a leader, there's a pretty good chance you're tired right now. But you're also probably pretty proud of the work that you and that your team have accomplished.

Look, I want to say right up front with this episode, it is designed not just for individual leaders, but also for leadership teams. If you lead with a team, if you serve on a team, if you support a team, this might be an episode that is worth listening to together with your team, or bring it back in a future conversation. Maybe it becomes like a homework assignment. Hey, everybody, listen to episode 253 of Leaning into Leadership, and then we're going to have a conversation.

Today's episode is about reflection, but that's not all. Today's episode is about clarity, but that's not all. Today's episode is about looking ahead into 2026 without rushing past the year and what it has taught us, both individually and collectively. Now, before we jump into today's episode, I want to take a moment and pause. I want to thank our partners, our friends,

and the sponsor of this episode, our friends at Digicoach. If you don't know, Digicoach is an easy-to-use mobile platform. It empowers school leaders to provide teachers with positive, actionable feedback tied directly to research-based instructional practices. It gives leaders real-time data that shows whether strategies are being implemented frequently and with fidelity. So decisions aren't based just on your gut feelings,

but rather on clear evidence that leads to better student outcomes. If instructional leadership and meaningful coaching conversations are priorities for you and your leadership team in 2026, Digicoach is a powerful tool that can support that work. Go to digicoach.com to learn more and tell them you heard about Digicoach on the Leaning Into Leadership podcast for special partner pricing. Once again,

Darrin Peppard (04:44.641)

That's digicoach.com and tell them that Darren set you. All right. Let's talk about what this year demanded of us, what I'm seeing coming our way in 2026 and how we can step forward with intention.

All right, I have been sitting with a lot of leadership teams at their tables lately. Tables where the conversation moves quickly because there's so much to cover. Tables where people show up prepared, committed, and deeply invested in their school or their organization.

And I've noticed something consistent across these rooms. Leadership teams are carrying far more than whatever it is that shows up on their agendas. They're holding the tension between instructional priorities and behavioral realities.

They're balancing support for their staff with accountability. They're navigating parent expectations, compliance demands, staffing challenges, and the ongoing work of culture, often all in the same meeting and being interrupted on a regular basis. I'm also seeing teams that are trying to take care of one another in the middle of it all.

Quick check-ins before a meeting starts. A glance across the table when a tough topic comes up. Quiet follow-up conversations after decisions are made. These teams aren't asking for more initiatives. They're not asking for grand solutions. What they're really looking for is alignment. Alignment around what matters most. Alignment around how decisions will be made. And alignment around how they support one another

Darrin Peppard (06:59.703)

when the work gets heavy. That's the context for this conversation. That's what I want to speak into. Because leadership isn't just about individual capacity. It's about how teams think and decide and lead together. How teams work toward a common goal.

To do that, I want to begin with talking about some trends that I'm seeing as we head into 2026. Now, here's the thing, the trends that I want to share with you here are not trends that I'm hearing on other people's podcasts, I'm not reading these in articles, I'm not getting these from reports or anything like that. These are simply trends I am seeing from the rooms that I'm in.

the leadership teams that I'm working alongside, whether that's in a boardroom, in a classroom, a conference room or a conference center.

The trends that I'm gonna talk about that I see coming our way in 2026 come from the people that I have been working with all throughout 2025.

five trends. Trend number one, leaders are tired. But that's nothing new. What's new and what's trending is that leaders are being a lot more honest about it.

Darrin Peppard (08:29.931)

I'm not seeing just the individual fatigue. I'm seeing collective fatigue. I'm seeing teams that are just exhausted. But what is really inspiring and what I think is going to make a difference in 2026 is that leadership teams are showing up for one another. They're feeling that cumulative weight of the work, but they're also being honest about it. They're naming it.

That's a huge trend right there. Just simply naming it and saying, yes, we are tired. We acknowledge that we are. Instead of just trying to work through it, to just overcome, overcome, let's just pour in harder, let's just work harder. I'm seeing leaders and leadership teams taking a step back and saying, wow.

I'm exhausted right now. Maybe I don't need to do this right this moment. And it's that honesty that to me is a first step toward meaningful change in leadership.

We're starting to see the end of just work through it, just work through it, just work through it. And instead, I'm hearing leaders say, something's got to change. There's got to be a better way. Simply acknowledging that, simply owning that, simply naming it and saying, we're tired, we're worn out, we're exhausted, and here's why. I think will be a big trend in 2026.

And I think it's going to help leadership teams and leadership individuals change the way they do.

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trend number two.

Yes, talk about clarity all the time. But I think clarity now is becoming not just a thing, not just a buzzword. It's becoming a survival skill. Not just for individuals, but also for teams.

The overwhelm, I heard this word so many times in 2025, the overwhelm of leadership.

It does not come from too much work. I'll say it again. The overwhelm does not come from too much work. Where it is coming from, and it's becoming abundantly clear, and I think this is a big thing in 2026, it's coming from unclear priorities.

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collective clarity is going to be an important thing in 2026 for leadership teams. Because when leadership teams are not aligned on what matters most, everybody feels it. Because everybody's working in a different direction or maybe somewhat towards the same goal, but not truly aligned.

But when leadership teams are clear, when they are truly in alignment, the work becomes a little lighter, certainly becomes more focused, and it definitely becomes more sustainable. If you've ever done work where you feel like every single day, it's the same thing over and over, and I'm not getting anything closer in any way, or form to what

The ultimate goal is you know what it feels like to work out of alignment.

Man, when you have that true alignment, when everybody's focused on the same outcome and they know what their role is and how they are contributing to that outcome, it gets a little bit lighter. I'm not saying you're not going to be exhausted. Don't get me wrong.

But when you feel that sense of accomplishment...

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That's when you're starting to really build towards something great. And it does feel a little bit lighter because it's more sustainable.

Trend number three, culture. Culture is no longer a buzzword. Culture is no longer a thing that you can overlook. Culture is no longer the thing that you don't spend time on. Culture is no longer built by one person.

Now, maybe you're the CEO of your organization. Maybe you're the principal of your school. Maybe you're the superintendent of your school district. And you say, yes, but Darren, it's my job to set the tone for the culture. Yes, absolutely. I heard it said recently that there's all these different definitions of culture, but culture can be simply boiled down to what is the absolute worst behavior where you willing to tolerate in your organization.

I thought that was pretty profound. You when you think about it, culture really is a collection of behaviors, a collection of expectations, a collection of how we do things, what we expect of each other.

how we are accountable to each other.

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And if we're okay with poor behavior, we're probably okay with poor culture.

I really think in 2026, the really great leaders, the leaders who are going to stand out in 2026, know that they have to focus on culture. They know that culture is shaped every single day by them and by their leadership team, modeling the behaviors, the conversations, the values that they expect to see throughout the organization. So yes, if you are the CEO, if you're the principal, you're the superintendent, you're the manager, the whatever title you have,

And you're saying, it's my job to build the culture. You're absolutely right. You have to decide what is it that you expect. You have to decide what is it that you want to see each and every day. And when people fall short, how are you going to support them to get to where you want them to be? And when people hit that mark or exceed that mark, what are you going to do to recognize reward and reinforce that so that you continue to build that culture up?

When you do that, you are modeling that for others.

when you model it for others, that's when they start to take it on. That is how you build the culture. And in 2026, you can't set culture aside. I don't care what walk of life you are in. If you're not thinking about culture, if you're not focusing on culture, then you are going to be faced with those dreadful things that so many of us are going to read about as trends in 2026, which is going to be things like retention.

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recruitment? How do we keep quality employees? How do we get quality employees? The answer is culture. That's a huge part of it.

Darrin Peppard (15:54.06)

How do we build a non-toxic environment? It's culture.

Those are the things we need to be focused on. And I really think in 2026 that culture is going to be no longer an afterthought for leaders. I think we have moved into a place in leadership where culture is king and leaders know they have to focus on.

It's not optional anymore.

Teams are seeing the cost of it. That cost neglect burnout turnover fractured trust. You can't survive as a leader. Your organization cannot survive when those are the words that are associated with your organization burnout turnover fractured trust lean into culture in 2026. That's going to be a big trend. Trend number four coaching not compliance.

coaching, not compliance. If you've ever worked in an organization that is all about compliance, you know exactly what I mean. Do it, do it my way or else.

Darrin Peppard (17:03.02)

Coaching. Not compliance. think that's a big, big piece as we go forward into 2026. I think we are seeing more and more and more these changes in leadership where leadership is no longer my way or the highway. Leaders cannot survive that way. Leaders cannot be sustainable that way. You have to grow and coach the people that you have. That shift moving away from compliance into coaching

Honestly, it changes how teams show up for one another. It changes how individuals show up. It becomes this, how do we get better together instead of my way or the highway? We start thinking about how we support the people we serve instead of how we get them to do what we want. It's a big shift.

But I really think we're going to see more and more and more of that focus on coaching versus compliance. We can't continue to think, well, they either need to do it my way or I'll go get somebody else. You've heard me tell the story before. I remember very well hearing Todd Whitaker talk about it. The first time I heard Todd speak his book, shifting the monkey had just recently come out, but he talked about how

If we're in a supervisory position and we have people not meeting our expectations, we can either go get better people or we can coach up the ones we have. Folks, we have to coach up the ones we have. And I'm seeing it more and more and more. I'm telling you, this is a trend heading into 2026, coaching over compliance. Finally, trend number five, the permission to simplify.

I'll say it again, the permission to simplify. Some of the most powerful moments that I saw during 2025 happened when leadership teams sat together and said, all right, we are doing too much or we are asking too much of others. How do we take stuff off their plate? How do we slow it down? How do we make it where it's something that's genuinely important?

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genuinely doable and will genuinely impact where we want to be.

That decision alone helps to create the alignment that I'm talking about, but it also gives everyone a sense of relief. I talked about it a few times here on the podcast and man, I did this activity so many times with leaders and leadership teams in so many different ways this year, but one of my favorite protocols.

Start, stop, continue, consider.

going through that protocol. I led so many leadership teams through that this year. What do you want to start doing? And think about it for 2026. Maybe it's a great activity. Do start, stop, continue, consider. What a great reflection activity, right? What do I want to start doing in 2026? What do I want to stop doing in 2026? What do I want to continue doing in 2026? And what should I consider in 2026? Great activity for you as an individual, but

If you are listening to this as a leadership team, if you lead a team, if you support a team, start, stop, continue, consider for 2026. Permission to simplify. Get it down to what you know and can focus on and that's doable and manageable and that people can buy into and believe in.

Darrin Peppard (20:49.567)

And by doing that activity, everybody has a voice. Everybody gets to be a part of it. Okay. So to me, five trends again in, 2026, just very quickly, I will just just remind you number one, leaders are tired, but they're being more honest about it. They're starting to actually name it trend. Number two, clarity. It's a survival skill. It is truly becoming a survival skill. Three culture. It's an absolute leadership team responsibility, right?

We have to set the tone for what it is we wanna see, then recognize reward and reinforce it. It's gonna be a big deal in 2026. Trend number four, coaching over compliance and trend number five, permission to simplify. All right, let's move into this next piece. This is a bit of a reflection and it's a reflection for me, but I wanna use this to challenge you to reflect on your own. I am not a New Year's resolution person anymore. I stopped doing that a handful of years ago.

And I started being a one word person. Actually kind of enjoy the one word. Clarity a couple years ago was my one word and I am telling you what crushed that word. In 2025, my word was evolve.

I wanted to really see how I could intentionally evolve. Not only as an individual, but also certainly our work here at Road to Awesome, our work here on the Leaning Into Leadership podcast. I wanted 2025 to be a year of evolution. And boy was it ever. It wasn't just evolving how I showed up. It wasn't just evolving my voice or my work. It was evolving.

as a business and as a person. Growth isn't always something that we see. It's not always loud. Sometimes it's some of the quieter decisions that you make or when you start to set some firm boundaries or you just simply trust in yourself and your team just a little bit more than you did before.

Darrin Peppard (23:01.565)

I would tell you that for me, evolution, the evolving here at Road to Awesome became not just about working and supporting leaders in the education space, but about growing and expanding that work into more corporate spaces. During 2025, we launched a brand new website.

Darrenpepper.com that focuses very much on keynote speaking, leadership workshops, leadership retreats, that work that I do in so many different spaces, but actually capturing it and bringing it into a space, a repository where people could come and find that specific work. That in and of itself was a big evolution. The podcast.

About to see a big evolution when we dawn into 2026, excited for when we open 2026 with some new episodes, you'll see and hear some changes almost right away. But it's also about how as an individual I've evolved. I mentioned at the top of the show how I allowed myself just a couple of weeks to just kind of shut it down and focus on a project here at the house.

something I normally would not have done. It's always difficult for me to take a day off, if you will, in air quotes. but I think that's, that's an area that, that I have grown, that I've evolved, that I've changed, that I've learned to maybe savor the moment a little bit more.

I also hear late in 2025 started a daily practice of gratitude. Something that has been on my list and then it's been on my mind. I knew it was important, but something I hadn't done. And I'm now just over a month into my practice of gratitude. And I will tell you, it is, it is shifting a little bit in my mind how

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I look at things, how I slow down in the moment. I think just that in and of itself probably had a lot to do with me being willing to take that time to step away and, you know, work on a project and not feel like I had to be working 24 seven.

I offer this this reflection for a couple reasons. One, it's very good for me to take a step back and reflect, but also it's not just about reflecting as an individual. Think about reflecting as a team. If you look back on 2025, how did your team evolve? How did your team grow and change during this calendar year?

Is there a word that would define your team? If you retroactively said, hey, you know what our word for 2025 was, what would that word be? What would other people say that word would be?

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I think taking the time to be intentional and think about what have you accomplished in 2025 is very important. I think that's why I love the one word piece so very much. And that takes me into this next piece, which is looking ahead in 2026, my one word. will tell you last year, it took me a long time to figure out what my one word was. I know very clearly.

in 2026. My word, my one word is fierce. As I look ahead, man, that word just keeps coming up. Just being fierce. Not loud, not aggressive, but fierce when it comes to being clear. Fierce when it comes to being clear about my priorities, about where I want to go, about how I want to show up, about how I want to help pour into leaders and leadership teams in

all walks. Being fiercely clear about that is how success will be defined here at Road to Awesome.

being fierce with my boundaries. You see here these last few weeks, knowing that I can set some of those boundaries around my work. And that by talking about them here on the show, I can model that for you because man, if you if you're like me, that's a struggle as a leader, setting the boundaries and saying, Nope, I'm done. I'm off the clock. I'm going home. I'm not available for a couple of days.

Being fierce with boundaries for me is going to be a big one this year. Being fierce with my commitment to what matters the most.

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I've worked with an incredible business coach and I'm part of an amazing business mastermind that have helped grow what we do here at Road Awesome, what we do here at Leaning into Leadership so very much. And I've been telling them for the last two months that there are pieces of what I do that I need to let go of, that I need to delegate to someone else. Now that we have a team in place, I need to start

handing some of those things off. I've talked about it here on the show a lot where as leaders, you need to delegate the things that other people can do. I have to now, you know, take my own advice. I have to follow through on that.

I need to be fierce, focusing on what matters the most, letting others do the things that don't necessarily need to be done by me.

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Think about this as a leadership team.

being fierce as a leadership team. To me, that would mean you are fierce in your alignment, that you're fierce protecting each other's priorities, and you're fierce about having honest conversations and supporting each other when things get tough.

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I'll be honest with you, five years into our Road to Awesome journey, being fearless is what got us here. But being fierce is how we're going to be moving forward. So I'm going to challenge you. Think about what is your one word for 2026. Let me know. Give me a shout out. I want to hear mine is fierce. I want to know what word are you going to use to be focused either as an individual or as a team.

Now let's talk about what's coming for Road Awesome. Man, everything that we have been building moving forward is centered on helping leaders.

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focused on helping leadership teams really gain that clarity together, really be intentional together and really walk in their collective purpose.

That work has been showing up in the podcast and the newsletter, my coaching, the blog, the speaking work.

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But as we move forward in 2026, here at Road to Awesome, we're going to see that work expand. I've mentioned it before, but really 2026 is where we are fierce about moving that leadership support out into more corporate spaces. The focus on education will not change. The focus on education will not be dampened. But now,

There are so many leaders in so many walks of life that need clarity, that need to be intentional. They need that support.

that perspective.

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that I can't not help them. I have to pour into that. And I cannot wait. I'm so excited about what 2026 is gonna bring for us here at Roto Awesome. You're going to see some changes in the podcast, nothing drastic, but you're certainly gonna notice some changes in January of 2026. If you read the blog, you're going to see some changes.

in the blog in 2026, still focused especially on those early career leaders and how early career leaders can find their footing and find success, gain clarity and be intentional.

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You'll see some things if you subscribe to our newsletter in how we now deliver content in that newsletter, focusing it much more on a teaching space and not just a delivery of content.

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2026 is going to be a great year here at Road to Awesome. We have some incredible books that we'll be publishing here at Road to Awesome. Some amazing books from some incredible leaders in the leadership space. Cannot wait to see those come out.

Darrin Peppard (32:58.728)

Alright, as we bring this episode to a close, and we bring this calendar year to a close, I want to leave you with one final thought.

Leadership doesn't reset simply because the calendar flips, but you and your team can choose how you step into what comes next. You don't have to have a perfect plan in January. You don't need to ever feel like I have to have every answer figured out from the word go. What you do need is to be clear, clear about what matters most.

clear about what your collective energy is best spent on, and clear about how you want to show up for one another as leaders. This past year asked a lot of you, and if you're tired, it doesn't mean you're failing. It probably means that you're doing the work that really matters. If you're part of a leadership team, I encourage you to bring this reflection back to your group. Create a space where you can ask, what did this year teach us?

What is it that we're proud of that we did together? And what do we want to protect as we move forward into 2026? For me, 2026 is going to be all about leading fiercely, fierce clarity, fierce boundaries, and a fierce commitment to what truly matters. Now, if you'd like to stay connected with us as we head into this new year, I would love for you to visit both DarrenPepper.com and RoadToAwesome.net.

you're at roadtoawesome.net if you've not already signed up for our newsletter, please do so. In 2026 again that space is going to be so much more intentional, much more reflective, and much more focused on teaching and helping leaders how they can gain clarity and lead with purpose. If the Leaning Into Leadership podcast has been helpful to you, whether this episode or others in the past, please consider subscribing, rating, and reviewing the show. And of course share it with others who

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are looking for some leadership, looking for a way to support their leadership team, and they may benefit from this message. That support truly helps this work reach others. Thank you for being a part of our community. Thank you for listening to the Leaning Into Leadership podcast, for reflecting with me, for continuing to lean into this space with intention. I am super grateful for each and every one of you, and I cannot wait.

to walk with you in 2026. Thank you. Get out there. Have a road to awesome week, a road to awesome new year. Take care.