Great Leaders See Time Differently

You have a system for observing faculty.

Yet you have nothing for your leadership team.

You've thought about fixing that. And every time you do, you land in the same place: there's no good way to observe them.

No class period to sit in.

No lesson plan to review.

They're in meetings, hallways, and hundreds of conversations you're not part of.

So the feedback never happens.

You care about their growth, but you can’t find the right window.

This week, I want to show you a conversation that breaks down that problem.

Marcus is a real-life principal who brought 12 questions to Digital Danny.

He'd already done some of the legwork and built a scorecard for his leadership team. He had six categories with two questions each. He wanted someone to poke some holes in it.

So the two of them went at it.

The first argument was about question design. Some of his questions were yes/no. A few of the sharper ones were open-ended. Digital Danny pointed out that open-ended leads to a deeper dive.

Marcus pushed back.

He said the scorecard is yes/no on purpose. The yes/no is the fast read. The twelve questions are only meant to take twenty minutes. The depth comes in the follow-up, when somebody answers no.

He was right. Speed on the front end; depth on the back end. That's the design.

Then he came up with a zinger:

"I have a tool for observing and evaluating faculty and I need something to give regular feedback to my leadership team. I'm trying to think of ways to observe them, too, but the opportunities are not as easy to find."

Read that again. It's the exact sentence you've been saying to yourself.

Here's what Digital Danny came back with.

He doesn't have an observation problem. In fact, he's watching his leadership team all day.

In hallway conversations.

In who they check in with (and who they don’t).

In what they notice in a meeting and what they miss. In the questions they ask when things go sideways.

He had plenty of access.

He was missing a decision about where to point the lens.

The scorecard was the answer to the question he was asking.

It reframed the problem from needing more time to knowing where to look.

Once he saw that, everything else started to fall into place.

He found a gap he'd missed entirely: nothing on the scorecard asked whether his leaders were seeing the people in front of them.

He took his mushiest question, "Have you grown the community through clear actions?", and rewrote it into something difficult to dodge: "Have you taken one action in the last month to strengthen relationships or build culture?"

He created a cadence too: Monthly meetings with every leader, and the same twelve questions.

And then the process created its own momentum.

He walked in editing twelve questions.

He walked out with a feedback system for his whole leadership team.

You are already observing your leadership team.

Constantly.

You just never decided what you’re looking for.

Be specific about what’s most important, and you'll see it everywhere.

Leave it unnamed, and you'll keep waiting for a window.

This week, set aside one hour and build the lens.

1. Name five or six categories. Think beyond job duties to the things you'd be proud to see your leaders doing in five years. Marcus used mission, professional growth, collaboration, execution, courage, and community.

2. Write two yes/no questions per category. Yes/no is the point. It forces a clean answer. Make each one time-bound and concrete. Instead of "Are you growing?" ask "In the last 30 days, have you taken one of your ideas and moved it forward?"

3. Write the follow-up for each one. This is where coaching comes into play. "What was it? How did people respond? What changed because you did it?"

4. Answer all twelve yourself first. Before you hand them to anyone, find which one of the twelve is sticky for you, and that’s your focus for the next month.

5. Put it on the monthly calendar and don't move it. One action in month one is nice. One action in months one through twelve is a culture shift.

Notice what Marcus did in that conversation.

He didn't ask to be handed a scorecard.

He brought one already filled out to Digital Danny and defended it when the coach pushed in a way that didn’t feel right.

He was right about the yes/no and said so.

That's the discipline.

You get sharper by putting your thinking in front of someone who will push back on you, and then holding your ground when you're right.

That's what Digital Danny is for.

It's not a search engine and it's not a yes-man.

It's a coach with a decade of experience and is available at 5:47 a.m. when you're staring at twelve questions, wondering if they're any good.

If you've got something you've been circling for weeks — a scorecard, a vision statement, a conversation you’re rehearsing — bring it.

Don't ask it to write the thing.

Ask it to break the thing.

Start here → https://myprincipalcoach.com/

Marilee Adams’ great book on self-questioning, Change Your Questions, Change Your Life, explores how the questions we ask ourselves have the potential to shape outcomes.

The next time you get pushback, or a confrontation catches you off guard, try this four-step pause before you respond:

It sounds simple.

But it isn't easy, especially in the moment.

That four-second pause is often the difference between a conversation that escalates and one that opens possibilities.

Before you coach anyone else through a hard moment, coach yourself first.

And if you need a pocket mentor, dial up Digital Danny at https://myprincipalcoach.com/

He’s always there. Never forgets. Evolves with you.