What’s Behind a CEO’s Overbooked Calendar? It Might Be Leadership Shock

Business professional looking at a computer monitor trying to schedule a meeting

A few years ago, I was running a leadership workshop at the office of one of my clients, a medium-size global pharmaceutical company. 

The workshop went well. As I was chatting to people at the end of the morning, the CEO’s Chief of Staff, Alicia, who had been at the workshop, pulled me aside. She told me how much she had enjoyed the morning, which is always gratifying, and then she said, “Can I ask you a question? Have you worked with a leader whose calendar is fully booked? It’s Michael’s calendar,” she explained. “It’s booked solid.”

Michael was the CEO of the company. He’d been promoted to the role about one year earlier. I had met him, but we hadn’t actually worked together at that point. I wasn’t sure what Alicia meant. “You mean he’s really busy?” I asked, stupidly.

“Well, yes. But I mean he literally doesn’t have any time in his calendar. If you look at his calendar, it’s booked for six full months. We have meetings we need to schedule, and we’re looking at the back end of the year before we can even get started. Have you come across that before?”

I began to realize what Alicia was telling me. “I have come across that problem before,” I said. “I’m pretty sure I know what’s causing it, and that I can help. Would you like me to talk to Michael?”

A woman business professional being asked for feedback by multiple people, all at once

“I’d be grateful,” said Alicia. “To be honest…” She glanced around and lowered her voice. “To be honest, if things carry on as they are, I think Michael will kill himself with overwork, and it’s kinda my job to stop that happening, you know?” She looked at me and smiled wryly. 

“But it’s also not good,” Alicia confided. “Things are not running well.” She broke off and looked as if she was worried she had said too much.

“Can you arrange for Michael and I to have a conversation?” I asked. “Then he can decide if he’d like to work with me on this.”

“I’ll look at his calendar,” Alicia said without thinking.

“Good luck with that,” I said, smiling.

Alicia laughed. “Leave it with me,” she said. “This is top priority.”

Over the course of my career as an executive coach, I have come to recognize an over-full calendar as a classic symptom of a very particular leadership problem.

There are usually some other symptoms that go along with the calendar issue. It often becomes clear that the leader is not engaging well with the team. He or she may well be having regular meetings with key members of the team, but those key members don’t seem to be getting any clear sense of direction. 

A man in a suit outside of a high rise building stressed out

The leaders themselves feel overwhelmed and stressed out. They feel that they are not doing a good job and are not really on top of things. They seem to be constantly firefighting and getting tied up with issues that demand their time and attention, but they are not really moving the organization forward in the way they had planned.

Behind all this is often a sense of bewilderment. Things have always gone so well for them before. You don’t get to be appointed to a senior leadership role if you don’t have a track record as a successful operator. But the old tricks don’t seem to be working. Something seems to have come off the rails.

I call it “leadership shock.” I’ll tell you a lot more about it soon, because it is the subject of my first book, which will be published in Spring 2024. It outlines the warning signs of leadership shock and provides a proven methodology to overcome it. The prescription includes leading with authenticity to better navigate future challenges and lead the organization to success.

Coming soon in spring 2024 — Leadership Shock book by Pete Steinberg

I can’t wait to share more details about Leadership Shock with you and tell you what happened with Michael. In the meantime, sign up for the book waitlist to be the first to know when it’s published


Pete Steinberg is an elite rugby coach, leadership consultant, and author who can help you and your organization overcome challenges and achieve unparalleled success. This article is based on an excerpt from Pete’s soon-to-be published book, Leadership Shock. You can connect with Pete on LinkedIn and at PeteSteinberg.com.

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