Matt Alley, Associate Director MASSP
Let’s be honest. May is weird.
You’re not at the starting line anymore, but you’re definitely not at the finish either.
Seniors are halfway out the door. Your energy is somewhere between “let’s finish strong” and “we made it.” And your student leaders? They’re starting to coast just a little.
But here’s the reality most people miss:
Right now is one of the most important leadership windows of the entire year.
Because what you do in these next few weeks quietly determines how next year starts.
Not your August meeting. Not your first day back. Right now.
If you can lock in a few key things before everyone leaves, you don’t start from scratch in the fall. You start with momentum.
Here are the three that matter most.
1. Lock in Your Leadership Team
New officers are either already selected or about to be. And most of them are stepping into roles with one big question:
“What am I actually supposed to do?”
If that question isn’t answered before summer, you’ll spend the first month of school fixing it. Instead, give them clarity now.
What this looks like:
- Define roles beyond just titles. What does this actually look like in action?
- Establish 3 to 5 team norms. How do you communicate, show up, and follow through?
- Hold a quick expectations meeting before the year ends
This doesn’t need to be long or complicated. It just needs to exist.
What it does:
- Students leave with confidence, not uncertainty
- Advisers don’t have to reteach everything in the fall
- Principals see a student team that is ready to lead
2. Capture the Year (Before It Disappears)
Every year, it happens.
Great ideas. Lessons learned. Things you swore you would remember next time. Gone by August. Not because they didn’t matter, but because no one captured them.
Before your current leaders walk out the door, give them one job:
Leave the next team better than they found it.
What this looks like:
Run a simple 30 to 45 minute reflection:
- What worked really well this year?
- What didn’t go as planned?
- What should we absolutely do again?
- What should we never do again?
Then document it. Nothing fancy. A shared doc works perfectly. Call it your “Next Year Playbook.”
What it does:
- Preserves institutional knowledge
- Gives outgoing leaders a voice and a legacy
- Helps new leaders skip the learning curve
For principals, this is where student leadership becomes a system, not just a group.
3. Build a First 30-Day Plan (Momentum on Day One)
If your first meeting in the fall starts with:
“So… what do you guys want to do this year?” You are already behind.
Strong teams do not start with questions. They start with direction. You do not need the whole year planned, just a running start. Check out our “Back to School Agenda” template and steal some ideas that work for your crew.
What this looks like:
- Plan your first meeting. Agenda, tone, and expectations
- Identify one early win. Something visible that builds momentum
- Decide how you will communicate with your student body
- Map out your first 2 to 3 leadership meetings
That’s it.
What it does:
- Builds immediate confidence in your new leaders
- Creates visible momentum early in the year
- Sets the tone for your entire program
Principals notice this quickly because student leadership becomes visible right away.
The Plus-One: A Simple Summer Touchpoint
You do not need a full summer retreat to make this work. But if you can bring your team together, even briefly, it makes a difference.
A plan is good. A plan that students help build is better. Here is a quick “Summer Meeting: Working Guide” for Advisers to reference.
Here are three realistic ways to do it:
Quick Meet-Up (1 to 2 hours)
- Review roles
- Walk through the 30-day plan
- Align expectations
Half-Day Planning Session
- Build out your first events together
- Practice leading a meeting
- Finalize communication plans
Full Retreat (if you have the capacity)
- Team building
- Vision setting
- Preview the year
Even one touchpoint helps turn nervous leaders into prepared leaders and a good plan into a confident start.
Use Tomorrow: Run This in One Meeting
If you are thinking, “This all sounds great, but when do I actually do this?” here is your answer:
Block one extended meeting or split it into two shorter ones.
Part 1: Leadership Clarity (20 minutes)
- Define roles
- Set team norms
Part 2: Capture the Year (20 minutes)
- Run reflection
- Start your Next Year Playbook
Part 3: Build the 30-Day Plan (20 to 30 minutes)
- First meeting plan
- Early win
- Communication strategy
Done. No extra meetings. No extra stress. Just intentional use of time you already have.
Final Thought
You do not need more time. You do not need a perfect plan.
But if you want to shorten the learning curve for your entire leadership team, there is one move that consistently makes a difference.
Invest in how your students are prepared before the year even begins.
That is where Summer Leadership Camp changes the game.
In just a few days, students do what normally takes months:
- They understand how to lead, not just hold a title
- They practice communication, planning, and decision-making in real situations
- They return with confidence, ideas, and a clear sense of ownership
The impact is immediate. It is not just a camp experience. It is a head start.
If your goal is to build a team that shows up in the fall ready to lead, not just figure it out, this is one of the most effective ways to make that happen.
Because the schools that feel ahead in September are not guessing.
They are prepared.