Episode 270: If Your Plan Starts in August, You May Already Be Behind
This week kicks off a three-part solo series focused on one critical question:
How do we actually plan for success in the coming school year?
April is a time when leaders are deep in planning—budgets, staffing, schedules, and resources are all coming together. But too often, we focus on what we’re going to do without fully thinking through how we set our teams up for success.
In this episode, Darrin challenges a common leadership assumption—that the work starts in August—and introduces a different way of thinking.
Because August isn’t the starting line.
It’s the reveal.
In This Episode
- Why so many leadership teams delay their real work until August
- The danger of treating the start of the school year as the starting point
- How lack of clarity shows up immediately when the year begins
- A powerful shift in thinking: “What must be true by August?”
- An introduction to backward mapping as a leadership strategy
- A simple exercise you can use right now to begin planning differently
Key Takeaway
Great leaders don’t wait for August to get started.
They use the time leading up to the school year to build clarity, align their teams, and create momentum—so when the year begins, they’re ready.
Try This
Pick one initiative or priority for next year and ask yourself:
What are three things that must be true by August for this to succeed?
Your answers will reveal exactly where your focus should be right now.
What’s Coming Next
Next week, we tackle a real challenge many leaders face:
What do you do when your team is in transition and August really is when everyone comes together?
Even in times of change, there are steps you can take now to set yourself up for success.
Sponsor Spotlight: HeyTutor
Strong leadership requires focus—and that’s hard to maintain when leaders are pulled into operational work that can be handled by the right partners.
That’s why Darrin highlights the work of HeyTutor, a sponsor of the Leaning Into Leadership podcast.
HeyTutor provides:
- High-quality, evidence-based math and ELA tutoring
- Full program management (recruiting, training, scheduling)
- Clear data tracking through an easy-to-use dashboard
Their support helps leadership teams stay focused on what matters most—leading people and improving outcomes.
Learn more: heytutor.com
Darrin Peppard (00:00.904)
And with that, welcome into episode 270 of the Leaning Into Leadership podcast. Coming to you a day late and completely honest, 100 % a planned thing. I wanted to give just a little bit of space to families on Easter Sunday. So I decided, hey, let's release this episode one day later. Next Sunday, don't worry, we'll get back to our regular schedule of dropping an episode every single Sunday.
So let's talk about today's episode and actually let's talk about what's coming up because over the next few weeks I'm going to be doing a three part solo series all centered around one idea. How do we actually plan for success in the coming school year? Because let's be honest it is that time of year. Budgets are being built. Staffing decisions are being made. In many cases your master schedule is either finished or you're working on it.
As you're listening to this podcast, you've started to allocate resources to make sure that the things you want to get done can get done. There is a lot of planning that happens in the month of April. That's why I'm choosing to do this series in the month of April. And here's another reason, because I've noticed something. In many cases, we're planning what we're going to do, but we're not doing the kind of backward planning.
that actually sets our teams up for success when the school year begins. So here's where we're gonna go in this series. Today, I wanna challenge your thinking around when the work actually gets started. Next week, we're gonna talk about what this looks like when you're dealing with turnover and transition within your leadership team. And then in our final episode, I'm gonna walk you through how we actually build alignment and momentum before the school year begins. Because,
If we get this right, we don't just start the school year strong, we stay strong throughout the school year. So let me ask you a question. When does your plan for next year actually begin? Because I've been having the same conversation over and over again with school leaders over the last probably month or so. And they're excited about next year. The leaders that I work with, they've got lots of really good ideas of what they want to do.
Darrin Peppard (02:24.856)
They've got good initiatives that they really want to roll out. Whether those are connected to culture or they're connected to instruction, relationships, they've got good ideas. But because I'm their coach, I of course ask the second question. The second question is, when does this work start? And almost always I hear the same thing. Well, we'll roll it out in August. Every time I hear that, I have the same thought.
That's not really a launch plan. That's a bit of a delay. Now, before we go any further, I want to connect this to something that I think is really important. One of the reasons that leaders do delay the work is that they don't have the space they need to really focus on it. They're pulled in a hundred different directions and they're putting out fires and solving problems, handling things that quite honestly don't always require their direct attention. That is why I appreciate the work.
of my friends at HeyTutor, a very proud sponsor of this podcast. HeyTutor partners with schools and districts to deliver high quality, evidence-based math and English language arts tutoring programs. But what really stands out is how they take the operational burden off of your leadership team. You see, HeyTutor handles the recruiting, the training, the scheduling, the program management, all while giving you
clear data on student progress through an easy to use dashboard. Here's why that matters in today's context. When leaders have the right partners handling the right work, it creates space. It creates space to think, space to plan, space to actually lead.
If your team is trying to build something meaningful for next year, as it relates to tutoring in math and English language arts, but they keep getting pulled into the weeds, I would encourage you to check out my friends at heytutor.com. Now go down in the show notes, there is a very special link that will take you to HeyTutor and let them know that you heard about them here on the Leaning Into Leadership podcast. All right, let's dive into this conversation now, folks.
Darrin Peppard (04:51.563)
I've seen the pattern far too many times to ignore it. And the pattern looks like this. Leaders are excited about next year. They've got this clear vision of where they want to go. They're thinking about culture. They're thinking about instruction. They're thinking about new initiatives. But everything seems to start in August. On the surface, that feels normal, right? Because
That's when the school year starts, right? That's when everybody comes back. That's when we kick things off. I mean, that's traditionally how it's been done. But here's the problem. August is not the starting line. August is the reveal. And what gets revealed in August is whether or not you've done the work leading up to that point. August doesn't create clarity. It exposes it. If your team isn't aligned, you're going to feel it.
Immediately. If your message isn't clear, it's going to get lost quickly. If your priorities aren't defined, everything is going to feel important and nothing is going to get done well. And before you know it, you'll be right back in the cycle of chaos. You'll be reacting, managing, and just trying to catch up. Before you know it, it'll be April of next year, and you'll be thinking, this time we're going to put a plan together that works.
So instead of asking, what are we gonna do in August? I think there's a better question that you should ask. What has to be true by August for this to work? And see, to me, that question changes everything because now you're not thinking about the event. You're thinking about the preparation. You're thinking about the alignment. You're thinking about clarity.
You're thinking about building momentum and that is where intentional leadership lives. Let me give you a very quick example. I had a conversation with one of the leaders that I support earlier in this previous week. And we talked about their instructional model that they are going to roll out to their staff beginning in August. Honestly, this is probably the fourth or fifth conversation like this that I've had in the last two weeks.
Darrin Peppard (07:15.135)
In this particular conversation, there are a couple of pieces that they've put in place to start laying the groundwork, but they're not giving any feedback. They're not really holding anyone accountable for doing that work yet. Here's the problem. By not setting that expectation now, when you still have a couple of months left, when you get to this other rollout in August, they'll wonder,
Are you really going to hold us to this? Because you rolled something else out in December and we really didn't do anything to grow in that area. We've got to make sure that our plan doesn't just start in August. We also want to make sure we don't give away the time we still have left. That's where backward mapping comes in. We'll go little deeper into this in the weeks to come, but I want to introduce the idea today. And I know you've heard the phrase backward mapping before.
But sometimes we don't think about it in the context of building our own plans for professional growth, student outcomes in our schools. So instead of starting with today and just moving forward, I want you to start with your launch. Whatever the day is, you already know what day your staff is gonna return, the day your students are gonna return. So go to that launch day and then let's work backwards.
I want you to define what success looks like when you roll this out and then work backward from there to where you are right now. You see, this gives you an opportunity to identify what needs to be true, who needs to be aligned, what conversations need to happen, and what communication needs to be layered over time. And you start building that now, not in August.
now. That is such a great way to get this process started now. You're not surprising anyone. It's not like a big surprise reveal in August. Instead, start building those steps now. And again, you do that with backwards mapping. Let me give you something simple you can do right now. Pick just one thing you're thinking about for next year. Just one.
Darrin Peppard (09:42.604)
and then ask yourself this question. Maybe do this on the whiteboard in your office, or if you're one of those folks like me who has to write everything down in a notebook or on your iPad, do this exercise first on your own and then with your leadership team. I want you to ask yourself, what are three things that must be true by August in order for this work to succeed? Write it.
down. I'll ask the question again, what are three things that must be true by August for this work to succeed?
whatever you just wrote, that is your work now through the end of the school year. That is what your team should be focusing on now through the end of the school year. Now, I know some of you are listening to this and you're thinking, know, Darren, that sounds great, but we're gonna have some turnover. We got some new people coming in. We have some people who are retiring. I've got a couple of leaders in different schools that are gonna be moving on.
We don't even have our full team together.
Yeah, you're right. That's a real situation. Honestly, that's probably true for a lot of people that are listening right now.
Darrin Peppard (11:06.839)
there are absolutely situations where August is when the full team finally comes together. So what do do then? Do you just sit and wait? Are you forced to start from scratch? That's what we're going to talk about next week. Because even in the middle of transition, there is still work you can be doing right now to set yourself and your team up for success.
Let me close with this pep talk. The difference I'm seeing right now in the leaders that I'm working with, that's not talent. It is an experience. It's timing. You see some leaders are waiting, others are building. They're creating clarity. They're aligning their team. They're having the conversations now that most people will push off until later. And when August gets here, they're not gonna be scrambling. They will be ready.
So don't wait. Start building. Because the leaders who get this right don't show up in August and hope that things go well. They're showing up now. They know they've already done the work that's going to make it happen in August. Hey folks, if this episode resonated with you, share it with another leader who's already thinking about next year. As always, rate, review,
and subscribe because when you do that, that's what helps spread the word even more about leaning into leadership. I appreciate you joining me today. We will see you next Sunday. As always, get out there, have a road to awesome week.







