This…

Read more

This…

Read more

Year One Revealed Something She Couldn’t Ignore

She’s a high school principal who just closed out year one. She inherited her admin team rather than building it. Relational, observant, the kind of leader whose North Star is simple: are kids happy to be in this building? Year one was for watching and learning. Year two is for the gas pedal.

But before she can floor it, she has to deal with what year one revealed.

One Innocent Question Blew It Open

Graduation went beautifully. Smooth ceremony. No angry parent emails. A win by every measure.

Except one.

The admin team had planned to go out for drinks afterward. A team thing. Then a family emergency pulled her home, so she skipped it.

The rest of the team still went. Almost all of them. They just didn’t tell one AP.

It surfaced days later, by accident. She asked her APs an innocent question — did you guys end up going out? — and watched one face fall.

You didn’t text me?

Then came the tears in her office. Not about one missed night. About what it signaled.

When she talked to the others, their defense was ready: she excludes us all the time. We get it, it’s crappy. But here’s why we felt this way first.

An admin team that isn’t unified. Members who don’t all like each other. A year of quiet resentment, finally out in the open.

And the team stays together next year, so none of it can be waved off.

She Did the Right Things. She Still Felt Like She Caused It.

Guilt, mostly. She’s the one who asked the question. In her mind, the conflict came out because of her.

And she’d already made smart moves. She met with each person privately before they talked to each other. Helped each one see the other’s side. The conversations happened. They went well-ish.

The Question That Changed the Whole Story

The first reframe was about the guilt: don’t feel bad this came out.

For a team to perform at its highest level, buried conflict has to surface.

Was the moment awkward? Sure. But she didn’t create the problem by asking a question. The problem was already there, doing damage in the dark. A portion of the team made a choice, as adults, and that choice had consequences.

She just turned the lights on.

The second beat came from something she’d uncovered in those private conversations. The two who felt excluded all year (the ones with the ready-made defense) got a simple question from her:

“Have you ever told her she makes you feel this way?”

Well... no.

So they wanted her to be a mind reader.

A whole school year of feeling excluded. Zero attempts to say so. Then one night of payback, justified by grievances the colleague had never once heard.

And the standard she set for them is the one worth stealing.

You don’t have to be friends. You don’t have to be friends at all. But you have to have a positive working relationship.

No pettiness. No score-keeping. Talk to each other.

What This Means for Your Team

Surfaced conflict beats buried conflict. The awkward moment isn’t the wound. It’s the start of the repair. If your team looks harmonious because nobody says the hard thing, you don’t have harmony. You have a delay.

Read more

This…

Read more

She’s a first-year principal who is anything but new to her building. Five years watching. Five years taking notes. When she finally got the seat, she moved fast. Bold decisions. High expectations. “Guns blazing,” in her own words. The kind of leader who would rather lose positions than people, and who refuses to spend another year waiting and praying for things to change.

The boldness worked. The building is moving. The vision is landing.

But it came with a cost she didn’t see coming.

Her two assistant principals have had a hard year. Tough conversations. Real accountability. Some disciplinary decisions.

All of it necessary.

And some of it counterproductive.

Because now both of them hesitate to make decisions. They’re worried about the repercussions of choosing wrong.

One of them spirals for days after a single mistake. Sky’s falling. Can’t rebound. Replays it over and over.

She doesn’t want her team living in that space. She wants to spend the summer rebuilding the dynamic. Supportive. Safe to take risks. A place where mistakes are okay — as long as they’re not sloppy ones.

And she wants to do it without taking her foot off the gas.

What She’d Already Tried

She’d told them mistakes are okay. “A hundred times,” she said.

And she’d modeled it. Or thought she had.

Every Monday in their admin meeting, she names her own misses. Dropped balls. Things she’d handle differently.

Her APs respond by comforting her. You have a million things going on. You had the best interest in mind. You’ll bounce back.

They give her good advice. They just don’t take it themselves. One of them spirals for days after a single mistake.

The Coaching Conversation

The question that opened the door for her:

Read more

This…

Read more

The …

Read more

The …

Read more

This audiobook…

Read more

Read more

You’ve been reading about Selfmentorship.

This is the chance to practice it.

On Thursday, April 30th at 7 to 8pm ET, I’m running the first-ever Selfmentorship Sprint. A live 1-hour session where you stop reading about what it looks like to drive your own development and start doing it.

Our agenda:

• The Selfmentorship framework

• I model a live Digital Danny session

• You work on something real

• Debrief and wins

$100 for the Selfmentorship sprint. 30 days of Digital Danny access included.

That means you walk out with a thought partner trained on a decade of school leadership coaching conversations— available at 11pm before the hardest conversation of your week, available Sunday afternoon when you’re thinking through next month, available any time you need to work something through and your coach isn’t on the clock.

Play-It-Safe Principals accept 4 coaching sessions a year. They schedule them, wait for them, and manage in between.

Ruckus Makers don’t accept that.

The Selfmentorship Sprint is for the principal who has been reading this and nodding — and is ready to do the work, not just think about it.

Register today

See you Thursday.

Danny

This…

Read more

She’s a high school principal in her second year at a school that, on paper, has everything going for it.

National rankings. Strong AP scores. State recognition for college readiness. The week of this coaching call, she’d hosted the state Secretary of Education in her building to celebrate a counseling team that helped students land on-the-spot scholarships.

By Wednesday morning, she was spiraling.

The Situation

The district had handed her an impossible scheduling timeline.

Eight positions to cut. Teaching assignments due before approvals were even finalized. Her counselors sitting in a room, drawing conclusions she couldn’t officially confirm. She was side-texting her supervisor, managing the room with careful half-information, and watching her stress climb in real time.

She almost rescheduled the coaching call.

Instead, she paused. Asked herself where she could have the most impact right now — not next week, not in the next meeting, but in the next ten minutes. She walked the building. Checked room temperatures. Connected with teachers sweating through a heat spike. Small thing. Real thing. She walked back to her office feeling like herself again.

She kept the call.

The Real Work

The scheduling chaos wasn’t what she needed to talk about. What was underneath it was bigger.

For months, she’d been working with her Instructional Leadership Team on a vision reset. The school had carried the same core values for ten years — three words that mapped neatly onto the school’s initials. Tidy. Forgettable. The kind of values that could belong to a naval base or a Fortune 500 or a middle school two states away.

Her team knew it. She knew it.

So they did the work: sticky notes, honest questions, real conversation.

• What must be true about this school in three to five years?

• What do we want students to experience every day?

• What are we unwilling to compromise on?

She mentioned, almost in passing, that she’d developed those questions with Digital Danny — her Selfmentorship guide trained on a decade of school leadership frameworks. Not generic prompts. The kind of questions that cut through to the real work.

They filled the wall with words. Opportunity. Engagement. Responsibility. Empathy. Global awareness. Self-reflection.

Then she fed it all into ChatGPT.

The output was exactly what you’d expect. A long, technically correct, utterly hollow paragraph. Rigorous. Purposeful. Globally minded. Safe, inclusive, responsible. Every word true. None of it theirs.

Read more

Read more

Three school leaders. One AP stepping toward the principalship. One principal in year four, rebuilding from the ground up. One veteran closing out a 20-year career and asking how to finish strong.

Different stages. Same underlying question.

Who am I as a leader — and have I made that clear enough to the people I lead?

The Situation

The AP was sharp, curious, hungry. He’d just picked up a summer school principal role, his first crack at the chair. He came with the right instincts: don’t take in too much at once, learn from people who’ve made the mistakes, figure out the potholes before you hit them.

But the deeper question surfacing wasn’t about logistics.

It was about identity.

The principal in year four said it plainly. She’d come into a situation where a beloved predecessor had been the entire system. When the predecessor left, a faction of the staff made it their quiet mission to see the new principal fail. Two years of second-guessing. Two years of leading from doubt.

I’ve been leading from a place of fear.

And then — almost as a confessional — she said the thing that connected all three conversations:

If you don’t define who you are, your staff will define it for you. And it’s never how you want them to.

What They’d Already Tried

The AP was building relationships intentionally. Handwritten notes, $5 Starbucks cards, genuine recognition. Not transactional. Just deposits in accounts he knew he’d eventually need to draw from.

The year-four principal had been planting seeds. She quietly invited a core group to a conference on conscious discipline, never announcing it publicly. Word spread. Eighteen staff members signed up. Nearly a third of her teaching staff, and she hadn’t sent a single email.

Both were doing things right. But neither had fully named their leadership identity. Not out loud. Not on purpose.

The Coaching Conversation

The question that shifted things for the AP:

Read more

Read more

Top 3 Musical Artists

1. Kendrick Lamar

2. Bon Iver

3. Bad Bunny

Top 3 TV series:

1. Slow Horses

2. Paradise

3. The Residence

Top 3 YouTube Channels:

1. Conan O’Brien

2. Mike Birbiglia

3. My First Million

Top 3 Comics:

1. Daredevil

2. Something is Killing the Children

3. Batman

Top 3 Non Fiction Books:

1. Storyworthy

2. 48 Laws of Power

3. This is Strategy

Top 3 Business investments:

1. Working with Matt Dicks

2. Speaking on more stages and taking risks

3. Upgraded computer (Macbook Pro M5 + Studio Display)

Top 3 Personal Investments:

1. Started an IRL intro to improv 6-week class

2. Joined a new gym: health is the best yet

3. Working with a therapist

Top 3 Experiences:

1. The Moth

2. Improv

3. Plymouth, MA with Miriam / MSAA Keynote

Your turn, I’d love to hear what made your TOP 3 of 2025 list for you.

Keep Making a Ruckus,

Danny

👋 Welcome to a 🔒 subscriber-only edition 🔒 of Ruckus Makers — the newsletter for bold school leaders who Do School Different. Each week we drop fresh content across our signature styles:

• The Reframe → Mindset shifts in 90-seconds.

• Dot AI → Supercharged leadership prompts and custom gpts

• MEH → The Onion meets Education. What could go wrong?

• First in Line → Exclusive access to content before the bookshelf.

• The Automatic School → A system that moves you FROM bottleneck TO breakthrough

• The Hot Seat → Coaching calls turned into case studies

• Digital Danny → Your 24-7 AI-powered leadership coach trained on 4M words of content and ten years of coaching experience.

You can learn more about this premium newsletter here.

Subscribe now

You think keeping the peace means avoiding the hard conversation.

Wrong.

Every time you dodge that difficult talk with the teacher who’s undermining you, or that AP who never follows through, or that parent who bulldozes boundaries...

You’re not keeping peace.

You’re compounding problems.

Here’s what actually happens:

Read more

👋 Welcome to a 🔓 free edition 🔓 of Ruckus Makers — the newsletter for bold school leaders who Do School Different. Each week we drop fresh content across our signature styles:

• The Reframe → Mindset shifts in 90-seconds.

• Dot AI → Supercharged leadership prompts and custom gpts

• MEH → The Onion meets Education. What could go wrong?

• First in Line → Exclusive…

Read more

👋 Welcome to a 🔒 subscriber-only edition 🔒 of Ruckus Makers — the newsletter for bold school leaders who Do School Different. Each week we drop fresh content across our signature styles:

• The Reframe → Mindset shifts in 90-seconds.

• Dot AI → Supercharged leadership prompts and custom gpts

• MEH → The Onion meets Education. What could go wrong?

• First in Line → Exclusive access to content before the bookshelf.

• The Automatic School → A system that moves you FROM bottleneck TO breakthrough

• The Hot Seat → Coaching calls turned into case studies

• Digital Danny → Your 24-7 AI-powered leadership coach trained on 4M words of content and ten years of coaching experience.

You can learn more about this premium newsletter here.

Subscribe now

I was on a coaching call last week with a school leader who’d just made a huge transition.

Elementary to middle school. New principal. New team. And for the first time in years, they were finally working with people who wanted to lead.

They told me about their assistant principal – a genuinely nice person who’d been at the school for five years. The kind of colleague you actually enjoy working with.

But there was a problem.

Simple tasks that should take minutes were becoming recurring problems. Like sending a school-wide message through their communication system. The AP didn’t know how to do it. After five years.

So this leader did what most of us do ...

They walked the AP through it step-by-step. Showed them every click. Made sure the message went out. Problem solved, right?

Not quite.

Because halfway through explaining this to me, they paused and said something that hit hard:

“I know that you have to do it a few times. I’m not sure what would have made him not come to me again.”

That’s when I knew we’d found the real issue.

The Hidden Cost of Being Helpful

Here’s what nobody tells you about being a supportive leader: Your helpfulness can accidentally create dependency.

Every time you solve a problem for someone, you’re making a trade. You’re trading your time now for... more of your time later.

Because here’s the thing – if they don’t truly own the solution, they’ll be back. And back again. And again.

Meanwhile, you’re wondering why you can’t focus on the strategic work that actually moves your school forward.

You’re not building capacity in your team. You’re building a queue at your door.

The Two-Tool Fix

The solution? It’s embarrassingly simple, but most leaders never implement it.

Read more