Stop Managing Your Team Like a Play-It-Safe-Principal

"I feel like my team isn't positioned to win" - here's what happened next

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Here's what most principals get dead wrong about team leadership …

They think having a plan means success is guaranteed.

This week I had a 1-on-1 coaching call with a client. Here’s a rundown of what we discussed and how it can help you lead more effectively.

Let's call him Rick. He's a principal who had just presented his OKRs to the superintendent and felt confident walking out of that meeting. He had his frameworks, his quarterly planning, his entry plan blueprint — all the tools a Ruckus Maker should have.

But when we dug deeper during our coaching call, the real story emerged.

"I feel like my team isn't necessarily positioned to win," Rick admitted, looking at his team scorecard. Out of his key team members, only one was in the green. Everyone else was yellow or red.

Sound familiar?

The Hidden Truth About "Positioning Your Team to Win"

Here's what Rick discovered (and what most principals never realize): Having the right systems doesn't automatically position your people for success.

Rick had veteran teachers who were classroom legends — they could handle any kid, create structured learning environments, and get results. But when it came to leading their grade-level teams? Complete disasters.

• Marcus in 4th grade: Brilliant teacher, but colleagues complained he wasn't collaborative and did everything "his way."

• Jennifer in 5th grade: Incredibly structured and caring, but showed zero collaborative learning spirit with her team.

• Linda in kindergarten: Strong teacher, but so serious with adult colleagues that she sucked the energy out of every meeting.

The problem?

Rick was treating leadership development like a binder exercise. He assumed that if he just clarified roles and responsibilities, these veteran teachers would magically transform into collaborative team leaders.

That's Play-It-Safe-Principal thinking.

The Three-Part Framework That Actually Works

Here's what we worked through with Rick — and what you need to implement with your own team:

1. Stop Assuming and Start Asking

Instead of guessing what your team members need or creating elaborate job descriptions in isolation, try this powerful question:

"Given my priorities and vision for what we're doing, what's your dream for our campus and what are you willing to do about it?"

This question does three things:

• Forces your team to think like leaders, not just task-completers.

• Reveals who's actually aligned with your vision (and who isn't).

• Creates buy-in because they're co-creating the solution.

I told Rick about a time when I asked this question to my office staff. One person who I thought I'd have to fire actually fired herself the next day, saying she didn't want to be part of the culture we were building.

The conditions you create determine who stays and who goes.

2. Master the Art of Strategic Delegation

Rick's biggest trap?

He was operationalizing everything himself and then getting frustrated when his team expected him to have all the answers.

"I feel like they're expecting me to operationalize everything," Rick said. "I'll come up with something and it's how I would do it and they won't like it."

Here's the breakthrough: Stop doing their thinking for them.

Rick wanted his team to analyze walkthrough data and create meaningful professional development. Instead of creating the entire system himself, here's what I coached him to do:

Define the success criteria, not the process.

Give your team:

• The Why: Here's the outcome we need to achieve

• The Resources: Here's what you have to work with

• The Constraints: Here are the non-negotiables (timeline, budget, etc.)

• The Success Criteria: Here's how I'll know you did a great job

• The Check-in Schedule: Here's how often I want updates

Then say: "How you get there is up to you. If you want feedback, I'll give it. But I'm not making the plan because I want you to lead."

3. Address the Adaptive Challenges Head-On

Rick had identified that some of his team issues weren't technical (lack of clarity) but adaptive (mindset and emotional intelligence problems).

For team members like Marcus who weren't collaborating well, I recommended the book Emotional Intelligence 2.0 — it has a pre-assessment that shows exactly where someone's gaps are, plus simple activities to improve.

But here's the key: You can't just hand someone a book and hope for the best.

Frame it like this: "I see tremendous potential in your leadership. This resource will help you develop the external awareness skills that will make you even more effective with your team. Let's check in about what you're learning."

The Brutal Truth About Leadership Development

Most principals treat leadership development like a one-time workshop. They send people to a conference or provide a training and expect transformation.

That's not how humans work.

Real leadership development happens through:

• Consistent micro-moments of mentorship (those check-ins Rick was planning).

• Clear expectations with space to grow into them (the delegation framework).

• Honest conversations about performance (not just annual evaluations).

As I told Rick: "You've got to have patience because it takes time for everyone to grow into dreaming big as a leader, thinking beyond their current perspective."

Your Next Steps (Don't Skip These)

If Rick's story sounds familiar, here's what you need to do this week:

Week 1: Audit Your Team

Create your own team scorecard. For each key team member, honestly assess:

• Do they "get it" (understand the vision)?

• Do they "want it" (show genuine enthusiasm)?

• Can they "do it" (have the capability)?

This is the exact framework I discuss in The Breakthrough Blueprint 👇

Week 2: Schedule the Conversation

Book 30-minute one-on-ones with your yellow and red team members.

Ask the dream question: "Given my priorities and vision, what's your dream for our campus and what are you willing to do about it?"

Week 3: Delegate Something Strategic

Pick one important project you've been planning to do yourself. Use the delegation framework to hand it off to a team member who needs to grow.

Week 4: Address the Adaptive Stuff

For team members with collaboration or emotional intelligence issues, provide specific development resources and create accountability.

The Bottom Line

Rick left our call with clarity on his next steps. But more importantly, he shifted from thinking like a manager who needs to control everything to thinking like a leader who develops other leaders.

Your job isn't to be the hero who solves every problem. Your job is to build a school full of heroes.

The difference between Play-It-Safe-Principals and Ruckus Makers isn't the quality of their plans – it's how they develop their people to execute those plans.

Stop doing everyone else's thinking for them. Start positioning your team to actually win.

Ready to stop managing your team like a Play-It-Safe-Principal?

Book a call to explore how to get the support you need — whether that's one-on-one coaching or joining other Ruckus Makers building legendary campus experiences in our mastermind program.

The choice is yours: Keep doing everyone else's job for them, or start developing the leaders your school actually needs.