Episode 274: If Everyone Was Pulling the Same Direction...
In this final episode of the 3-part planning series, Darrin Peppard shifts from planning and preparation to something even more important—what happens when your plan meets reality.
Through a candid story from his time as a superintendent implementing project-based learning, Darrin shares what worked, what didn’t, and the leadership lessons that emerged when execution didn’t match expectations.
Because the truth is—most plans don’t fail in the planning phase.
They fail in the implementation.
Key Takeaways
Planning Isn’t the Problem—Leadership Is
You can have the right plan, strong training, and full buy-in…
and still see inconsistent results.
The difference?
How the work is led once the year begins.
Same Plan, Different Results
Some educators:
- Collaborated and sought feedback
- Opened their classrooms
- Engaged students deeply
Others:
- Struggled to see the fit
- Defaulted to old routines
- Or simply didn’t follow through
Same expectations. Very different outcomes.
4 Leadership Moves That Change Everything
1. Make the Work Visible
If the work matters, it must be seen.
Without visibility, implementation becomes optional.
2. Build Ongoing Support
Training starts the work—it doesn’t sustain it.
Coaching and follow-up are essential.
3. Systematize Feedback
Don’t leave support up to initiative.
Build regular check-ins and feedback loops into the system.
4. Hold Leaders Accountable
Alignment doesn’t happen by accident.
It happens when leaders consistently lead the work.
The Big Lesson
Your plan doesn’t fail because people didn’t understand it.
It fails when you haven’t built the conditions for it to live throughout the year.
Series Recap
- Episode 270: Don’t wait until August—you’re already behind
- Episode 271: Do the work now to prepare for success
Sponsor Spotlight
This episode is sponsored by HeyTutor.
If improving student outcomes is part of your plan, don’t wait until the fall to build your support system.
HeyTutor provides high-dosage tutoring in Math and ELA—handling recruitment, training, and management—so your team can focus on impact.
Learn more at HeyTutor.com
🎯 Let’s Connect
If you’re working to move from planning to execution—and want to ensure your team stays aligned and focused throughout the year—Darrin can help.
Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.
Darrin Peppard (00:00)
All right, my friends, welcome back into the Leaning Into Leadership podcast. This is episode 274. This is the final episode in our three part series we've been doing here in the month of April, where we've been talking about planning for your upcoming school year. Now, if you look back, you'd see that episode 270 was the episode that we talked about why your plan might fail if you're waiting until August to get started with the work.
In 271, we talked about what the work is that you need to be doing between now and August to ensure that you are going to have success in your plan. And today I want to talk about what happens when your plan meets reality, because that's where the real leadership shows up. I want to tell you a story through the course of this episode about one of those times in my leadership career that we thought we had the plan.
but it didn't always go exactly the way we wanted it to. You see, in this case, we thought we did everything right. We really did. We had a plan, we had the training, we had a lot of excitement. I was in the training myself. I believed very much in this work. I knew it was going to be good for our students. And then when the school year started, not everybody followed through.
not everybody implemented in the way that we would have expected them to do. We had some who really leaned in and did the work, we had some who didn't. And it was that gap that taught me one of the most important lessons of my leadership journey. That's what we're gonna talk about today. Before we do, let me take a moment and pause and talk about our friends at HeyTutor, today's episode sponsor.
You know, when I think back on that experience, one of the biggest lessons that I take away from it is it's not just about having a plan. It's about putting the right supports in place before you need them. And that's especially true when we're talking about student support. If you already know that some of your students are going to need additional help next year, whether that's intervention, acceleration, or targeted support, why would you wait until September to figure that out? That's why I encourage leaders to take a look at HeyTutor.
You see, HeyTutor provides high dosage tutoring in math and English language arts, both in person and online. And they handle all the recruiting, all the training, and all the management of the tutors for you. Yeah, that's right. Your leadership team does not have to deal with that. Instead, you simply work with HeyTutor. They take care of all the work with the tutors. They give you wonderful reports that you and your teachers can use to track student progress.
So instead of scrambling in the fall, trying to figure out how you're going to build something, I would suggest you put that system in place right now. And then when the year begins, you already have it in place and it's ready to go to work. So if student outcomes are a part of your plan, this is a great way to start doing the work before the year begins. Go visit them at heytutor.com or even better, hit the link down in the show notes. That'll let them know that you heard about them here.
on the Leaning Into Leadership podcast. Okay, folks, let's dive into this conversation. And today, like I said, I want to share a story about one of those plans that I had and how it went well, but it didn't go as well as it could have. So when I was a superintendent, we made the decision to move forward with project-based learning across our district. We brought in really high quality professional development.
And we did it over multiple days. So I wanted to ensure my teachers had some flexibility. So I brought it one time during the summer and then one time right at the beginning of the year. And I gave my teachers the option. You can come to the one in the summer and if so, you can flex those days at the beginning of the school year when others are doing the training. If you want to not be there, if you want to just work in your classroom,
That's up to you. You have to do this two and a half day training. So you can either do it in the summer or you can do it when we start the school year. And honestly, we have about half at each of those trainings. It worked out really well. We had our administrators in the training. We gave them time to build and design their projects. And I'll be honest, I was so excited going into the year. I thought, man, this is going to be amazing. I really believed in it.
I thought it was exactly what our students needed. I really felt like for our context, for our size, that this was going to be amazing. It was going to give students an opportunity to demonstrate learning in ways that were different than traditional methods. And the truth is, I really thought we were ready when August came. And then the year started. And here's what happened. Some of my teachers
my gosh, they absolutely crushed it. They absolutely crushed it. And their students loved doing the project-based learning. See, my teachers who really got after it, they partnered up with their colleagues, maybe with a grade level at the elementary school, or maybe with a similar content group in our secondary. Many of them worked with our instructional coach. A lot of them asked for feedback along the way. Even
in their planning process. Many of them invited us to come into their classrooms while the work was in progress, not just when students were doing presentations. And the thing was, when we went in the rooms, man, their students were truly engaged, not compliant, engaged. Their classrooms just felt alive. And they were doing exactly what I had hoped that we would see happen.
But unfortunately, that wasn't true for everyone. Some teachers really struggled with seeing how it fit their context. And I understood that. I heard teachers also who said things like, I already do this. I just call it something else. Some of them made excuses. And some just flat didn't do it. And if I'm being honest, some probably realized that nobody was going to check on them.
and they went right back into their old routine. Same training, same expectation, but very different results. That is reality. When we bring something new into play, that's what's gonna happen if we're not really intentional.
And the truth is I remember how it felt. I was frustrated. I really believed in that work. I was disappointed, especially in some of the teachers who, man, I thought they were fully bought in during the training. They were excited, they were sharing what their ideas were. And then the year came and it just didn't happen.
And if I'm really being honest here, I was frustrated with one of my school leaders because that individual didn't really lead the work that we expected to be led. That individual just told people what they wanted to hear and they didn't hold anyone to a standard. And that mattered because when leaders don't lead the work, the work doesn't happen.
Now it might happen in certain pockets because teachers are excited about it, but if we don't have an expectation and hold to that expectation.
That's what happens. I was really frustrated with that.
Over time, think I've really come to a realization about it when I reflect on it. I really don't believe this was a planning problem. I really don't. I think the plan was extremely well laid out. We had done a lot of homework prior. I had taken a group of teachers from each of the buildings to see project-based learning schools.
I mean, they'd had the opportunity to be in the classrooms. They were excited about it. They were going to come back and lead it.
It certainly wasn't a training problem. We brought in very good training. And as I said earlier, we gave plenty of opportunity and even choice for the teachers to be able to still do the training, but have some flexibility in their schedule. I think the big thing that on reflection for me, especially as I prepared for this particular episode, I found myself reflecting even more.
This was a leadership problem. And not in the sense of pointing the finger of blame. That's not what I mean. I mean from a responsibility sense. We had a plan, but we didn't fully build the conditions for the plan to live once the year began. Like we didn't stop and think. When, when it all gets crazy, how will we respond?
did not do that.
We didn't have a system that would allow us to see the work. And by that I mean this. We didn't put together a shared calendar that would have allowed us to see when each individual was planning to utilize a project during that school year in their classroom. Now, I guess I should clarify here. The expectation wasn't that everybody launched a project on day one.
The expectation was everybody launches a project at some point during that particular school year. We were fine with it. I didn't expect us to be wall-to-wall project-based learning right away. Absolutely not. And I didn't figure we'd ever be wall-to-wall project-based learning. There's still great spaces for direct instruction for all different types of assessment and those types of things. I wasn't expecting everything to change on a dime.
But I probably didn't communicate that very
We also didn't really have a way to truly track that implementation. And I'm not saying we needed a visible scoreboard or something like that, but we definitely needed something in place where we could say, hey, these 11 teachers, they have done a project this year. We have these seven who have not or whatever, right? That would have been something that would have made a big difference for us.
We also didn't have in place, and I think this was one of the things, I don't want to call it an excuse because that's not fair, but at the secondary level, I think our teachers were reluctant sometimes to start a project because we didn't have a way to ensure that our students weren't being overwhelmed with too many projects at once. Now I will say this, we don't tend to worry about if our students are overwhelmed by too many tests at once.
I know that that's come up in secondary schools, but I don't think teachers worry too much about that. But nonetheless, we did not have a way to ensure that we weren't overwhelming our kids. So I guess I would say this, if the work really matters, it needs to be visible. And if it's not visible, that's when people have the opportunity to either choose
not to do it, to forget to do it, or to just simply fall back into their routine. I really think that's by far and away the ones who did not. I don't think they were obstinate. I don't think they were trying to be difficult. I think in many cases they just got back into the routine of a regular school year and it just didn't come up.
Essentially, if it's not visible, it becomes optional. That's a big takeaway for me from that. I think also too, one of the things that I wish we would have done on reflection would have been to ensure we had ongoing support. You know, we brought in two fantastic trainers for project-based learning. Our staff absolutely loved both of them.
And certainly they were available to us, but we didn't build into our plan to bring them back on site once or twice a year to provide some follow-up support, to build in some coaching cycles. None of us were experts yet. Our trainers were. If we had put that in,
it would have given an opportunity to reinforce and to bring back to the front, and the front of minds, this particular work.
So when I reflect on that, think that the training is what starts the work, but the training is now what sustains it. We have to have a system of ongoing support. So as you're looking at your plan and thinking through this coming year, what are you doing to ensure you have ongoing support built in? Just like we need to have
that visibility to the work.
We've also got to make sure we've got something for ongoing support.
third thing that I would do differently is I would systematize feedback.
The teachers who really succeeded, they wanted feedback. They asked for it. They sought it out.
But we left that up to the individual to take the initiative to ask for that feedback. And I know our instructional coach did a, she did a brilliant job. She was so, so, so good. I know she was intentional and reached out to everyone, but we didn't necessarily put a clear system and expectation around that feedback into play.
That was a mistake. I think if I did this again, if I had it to do over, I would build into the system regular check-ins. I would build in coaching conversations, and I would build in opportunities for feedback. Because support shouldn't depend on whether or not someone asks for support.
are ones who are going to struggle the most, who may back away from it, who may just say, hey, you know what, I just completely forgot about that. They're probably the ones who need the most support. And if we provide that support, if we kind of create that it's okay to learn as we go process, there's a higher likelihood they're going to lean in and actually adopt.
what it is that you want them to do. So make sure that you are doing something to systematize feedback. That's such an important piece when it comes to really creating that growth. Another thing, and this one is 100 % on me, I was the superintendent. I would hold leaders accountable for leading. I had lots of conversations with my leaders and I will tell you,
And I had one who was doing spectacular work. The project that person created in their training pertained directly to their building. You could see that that person, they were bought into the work.
This is so critical. If you're in a position where you have leaders you are counting on to lead the work, if you're a superintendent, an assistant superintendent, maybe you're a building principal and you have have a team of assistants, you have to hold your leaders to account.
If they don't lead the work, the work will not happen. It can't just be you. There has to be a team and you've got to hold them to that expectation. For me, I think again on reflection.
I would really, really ensure that my expectations were clear. Looking back, perhaps they weren't. I thought they were. I really did.
But the fact that we didn't live up to those expectations tells me I didn't do a good enough job ensuring that my expectations were clear. A second thing is follow through. If I say this is what we need to do, I need to be the one who's putting it regularly on my calendar to check in and follow through and ensure that that work is happening.
And I think I would be a lot clearer about what it really looks like to lead an initiative. You see, as the superintendent, I really wanted my building leaders to lead this initiative, not me.
And, man. And again, I feel like for the most part that's what happened, but I did have one that just, that's not how it worked. And it takes me back to my time as honestly an assistant principal and the work we did and then I got to lead with the implementation of our career academies. Now in this particular case, it wasn't the entire school. It was two.
very highly motivated groups that in a lot of ways we had handpicked to drive this work.
I knew what it felt like to successfully lead an initiative. But I don't think I was clear enough as the superintendent on what leading that initiative should look like in my buildings.
That's totally on me. It really is. This particular one really matters, folks. You've got to hold your leaders accountable for leading the work, no matter what their role is. Alignment doesn't happen by accident. It happens through leadership. Man, that's so important. I'm going to say it again. Alignment doesn't happen accidentally. It happens through leadership.
So here's the takeaway for this episode. Your plan does not fail because people didn't understand.
Your plan can fail because you didn't fully build the conditions for it to live successfully during the entire year. Don't just plan for the kickoff. Plan for when something unforeseen happens. Plan for the second half of the year. Plan for how you finish it strong. Because
Everybody can put a plan together to build excitement in August. But really clear leaders, really intentional leaders will ensure that their plan is executed throughout the entire course of the year. And they're going to do that with the four things I mentioned that I would do differently.
Number one, make the work visible. Number two, build ongoing support, not just one and done training. Three, systematize feedback. And four, hold those who are charged with leading the work accountable for leading the work. To me, that's what this is all about.
Okay, folks, thank you so much for joining me here on Leaning Into Leadership. Thank you so much for dialing into this three-part series during the month of April. This has just been fantastic. I've enjoyed it. I really, really appreciated the opportunity today to kind of go down that memory lane a little bit and share some things that maybe weren't so successful for me and ways that I was able to kind of modify that and through reflection, give you some guidance.
on how to make sure your plans are as successful as they can be in the upcoming year. Get out there. Have a road to awesome week.







