The Winning Leadership Playbook

The Winning Leadership Playbook Helping leaders turn the unconventional into practical, repeatable results. Winning Leadership Playbook™ by Mark Calitri.

09/01/2026

Saying no is easy. Finding a way to say yes takes leadership.

Not every idea will work. But the best leaders don’t start with all the reasons it can’t be done. They work with their people, collaborate, and find a way to say yes.

Before you say no, ask: What would it take to say yes?
Read the short Winning Leadership blog here:
https://www.markcalitri.com/2026/09/saying-no-is-easy-finding-way-takes.html

08/31/2026

I’ve been working on something new for Winning Leadership.

Four characters. Four different perspectives. One goal: tackle the real questions people wrestle with about work, leadership and life.

The first question is a big one: What are we really working this hard for?

08/24/2026

The Oscar Mayer Wienermobile stopped me.

That’s the lesson. You don’t have to be louder than everybody else. But you do have to give people something worth remembering.

What does 4,256 really tell you?On this day in 1986, Pete Rose collected the final hit of his career.You don’t get to 4,...
08/14/2026

What does 4,256 really tell you?

On this day in 1986, Pete Rose collected the final hit of his career.

You don’t get to 4,256 on talent alone. You show up, compete and keep coming back.

That’s one of the lessons behind **The Winning Leadership Playbook: The Pete Rose Way.**

Think you know Owensboro?    Next week I'm speaking Senior Community Center of Owensboro-Daviess County about what's cha...
08/13/2026

Think you know Owensboro?
Next week I'm speaking Senior Community Center of Owensboro-Daviess County about what's changing., what's coming, and why it matters to the people who live here.
Best part is I'm going to ask questions and hear what they think.

Let's Celebrate Our City! Mark Calitri, president and CEO of the Convention and Visitors Bureau, will share information about how the CVB works to promote tourism and visitors to our city – and how their efforts benefit those of us who live here - at 4 p.m. Tuesday, Aug. 18, at the Senior Community Center, 1650 W. Second St.! Come and learn more about the special events, conferences, conventions and tournaments Mark and his team bring to Owensboro!

This program is part of our Senior Class adult education series. Membership in the Senior Community Center is FREE to all residents of Owensboro/Daviess County age 60 and older. Register in advance for this and other great sessions by visiting our office at 1650 W. Second St., or call 270-687-4640, or sign up online at https://forms.gle/oaXSYqm41zxTFSCs6

Eat your own dog food.It sounds ridiculous, but it is one of the best performance lessons I have ever learned.If you exp...
08/03/2026

Eat your own dog food.

It sounds ridiculous, but it is one of the best performance lessons I have ever learned.

If you expect your team to be prepared, be the most prepared person in the room. If you expect hard work, they need to see you working hard. If you expect people to own their mistakes, own yours first.

Watch the video and read the full article:

https://www.markcalitri.com/2026/08/eat-your-own-dog-food.html

07/17/2026

One day changed baseball forever.

Wally Pipp had a headache and asked out of the lineup. Lou Gehrig took his place.

The rest is history.

The leadership lesson has nothing to do with baseball... and everything to do with being ready when opportunity knocks.

▶️ Watch the video.

07/15/2026

One question has guided my leadership for years...

Would you be proud if everything you did today appeared on tomorrow's front page?

That's what I call the Front Page Test. It's a simple way to measure integrity, build trust, and make better decisions.

Watch the video below. The full article is in the comments.

07/14/2026

Everyone loves the home run.

I've always believed championships are built with singles.

Babe Ruth changed baseball by swinging for the fences. Pete Rose took a different path, building success one hit at a time. That philosophy has shaped the way I lead teams, make decisions, and approach every day.

Small, stackable wins. That's how lasting success is built.

Watch the video below, and if you'd like to go deeper, I'll put the full Winning Leadership article in the comments.

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