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.

• 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

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.

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.

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.

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

In this episode of the Leaning Into Leadership podcast, Dr. Darrin Peppard takes on a challenge that quietly impacts even the strongest leadership teams: misalignment.

You can have talented, committed leaders who care deeply about their work—and still feel like something is off. Conversations feel unclear. Decisions take longer than they should. Initiatives pile up without traction.

That’s misalignment.

And while it may not be loud or obvious, it comes at a cost.

In this episode, Darrin breaks down:

• What misalignment really looks like in leadership teams
• The hidden costs, including decision fatigue, staff confusion, and lost time
• A personal leadership story that reshaped his understanding of alignment
• Why alignment doesn’t happen during the work—it must be built intentionally

Darrin also shares a practical tool you can use immediately with your team:

This simple protocol helps leadership teams:

• Identify what needs to be added
• Eliminate what’s no longer aligned
• Protect what’s working
• Think strategically about what’s next

Whether used in a leadership retreat or a focused team session, this process creates the clarity and shared direction teams need to move forward together.

Key takeaway:

Your team doesn’t need to work harder.

They need to work together—on the right things, in the right way.

• Blog: Start, Stop, Continue, Consider Protocol
• Connect with Darrin: darrin@roadtoawesome.net
• Learn more about leadership retreats and team development

Thank you to our Amazing Sponsors

This episode is sponored by DigiCoach, helping leaders capture real-time instructional data, provide meaningful feedback, and build clarity through strong systems. Go to digicoach.com and tell them you heard about them here on the Leaning into Leadership podcast for special partner pricing.

This episode is also brought to you by HeyTutor, delivering high-impact, research-based tutoring that supports students while reducing leadership overwhelm. Connect with them at HeyTutor.com

In this episode, Darrin sits down with Brooke Dukes to explore a challenge that many leaders face—but often don’t recognize:

Becoming the bottleneck.

We talk about how this happens unintentionally, why it’s so common among high-performing leaders, and how it ultimately limits both team growth and organizational success.

Brooke brings a powerful perspective to this conversation. As the founder of Success by Design Club and creator of OZ, an AI-powered leadership coach, she has spent over two decades working with leaders at the highest levels—including Fortune 500 organizations—helping them break free from burnout and lead with clarity and confidence.

Together, we dig into the dangers of “superhero leadership,” the hidden cost of control, and why stepping in to help can actually hold your team back.

Most importantly, we explore what it really takes to shift—from being the center of every decision to building systems and structures that allow your team to step up and thrive.

If you’ve ever felt overwhelmed, stretched thin, or like everything depends on you… this conversation is for you.

1. How leaders unintentionally become the bottleneck
2. The danger of “superhero leadership”
3. Why helping can actually hurt your team
4. The role of systems in scaling leadership
5. How to build trust, clarity, and accountability
6. Why burnout is often a systems issue—not a personal failure

Brooke M. Dukes is the founder of the Success by Design Club and creator of OZ, an AI-powered leadership coach designed to help leaders grow without burning out.

With over 20 years of experience in executive leadership, sales, and consulting—including work as a Fortune 500 executive and global strategist—Brooke helps CEOs, founders, and visionaries build businesses that actually work for them.

Her work blends behavioral science, Human Design, and real-world strategy to restore clarity, confidence, and calm in leadership.

She is also the creator of the GRACe™ Communication Framework and Culture Compass™ Diagnostic, a #1 best-selling author, host of the Burn On, Not Out podcast, and a sought-after speaker known for her honest and heart-forward approach.

1. Website: brookmdukes.com
2. Podcast: Burn On, Not Out
3. Social: @BrookMDukes

Get Darrin's weekly blog here

Thank you to our Amazing Sponsors

This episode is sponored by DigiCoach, helping leaders capture real-time instructional data, provide meaningful feedback, and build clarity through strong systems. Go to digicoach.com and tell them you heard about them here on the Leaning into Leadership podcast for special partner pricing.

This episode is also brought to you by HeyTutor, delivering high-impact, research-based tutoring that supports students while reducing leadership overwhelm. Connect with them at HeyTutor.com