CEO Leadership

How CIOs Keep Their CEOs From Quitting

CEOs are quitting. A major reason cited is because they don’t have the skills to lead their company into transformation. The problem is, people misunderstand transformation. CIOs don’t. And that is why the CIO needs to help keep their CEO from quitting prematurely.

Scott Smeester


April 20, 2023

Photo credit:
Milas Fakurian

We sat down with our coffees. The outside terrace was outlined by green trees and potted plants. The cool morning air was lit by a rising sun that promised a warm day and final break from winter.

“I’m thinking about quitting,” he said. 

My friend is a veteran CIO.

I paused, took a sip, and simply asked, “Why?”

“You know I’ve been working for years by my CEO’s side. He told me he is considering leaving. I’m not sure I want to work with anyone else.”

“And why is he leaving?”

“He doesn’t feel like he has what it takes to do what the Board wants him to do.”

“Which is?”

“Business transformation, to use their words.”

“Interesting,” I said. “Did you know that CEO resignation has increased once again this year? And the main reason cited is just that. CEOs don’t feel they have the competency set to lead “transformation.”

“Why did you say it like that?”

“Look, some CEOs need to resign, right? Their time has come. I get it. But most are leaving either because of personal pressures or over a misconception of transformation. And I think that more often than not the pressure is there because the misconception is there.”

“According to Deloitte, 70% of executives last year considered quitting”

“I didn’t know it was that high,” my friend chimed in.

“I know, it’s crazy. Something is in the water, and I can tell you what it is.”

“We are confusing change and transformation.”

“What do you mean?” my friend asked. 

“Transformation involves change. It is a thorough change from one thing to another. Our word metamorphosis is based on the Greek word for transformation. Caterpillar to butterfly, that kind of thing.”

“But not all change is transformation. Dramatic as it can be, change may be a different way of doing something, but not necessarily changing into a different state of being.”

“Think about it. Dysfunction to function, unhealthy to healthy, not profitable to profitable, keeping pace to setting the pace, follower to leader. Those are changes of being.”


“Or look at it this way,” I added. “YouTube started as a dating website. Play-Doh started as a wallpaper cleaner. I remember when Amazon came out as a bookseller and when Netflix sent me DVDs in the mail. They didn’t just change how they did things. They became something different.”

“Fun to know,” my friend said. “But how does that relate to us?”

I leaned forward. “Transform is better understood against the word conform, from which we get the word schematic. It’s the idea of following a pattern.”

“You know that I love change. But change can be taxing. We can implement a lot of change and all we are merely doing is conforming to what everyone is doing. We are just following the pattern”

“You can change and still be like everybody else.”

“Wait,” my friend interrupted. “Say that again.”  

I said, “You can change and still be like everybody else. And that is not executive leadership. And that is why CEOs are wearing down.”

“Because we are just keeping up with the Jones’ as my grandpa used to say.”

“Exactly. CEOs want to change their industry, right? They want to make a difference. Of course they drive to the bottom line, but I know few effective CEOs who don’t have a bigger vision.”

“I think my CEO would say that his vision is blurred, like traffic passing by at high speeds,” my friend said.

“I can believe that. And the thing for you to realize is that you are the best person he has to keep him where he needs to be.”

“Why is that?”

“You understand transformation. Your digital transformation was a huge success right?”

“I would say so.”


“Fun story. I had a mentor when I first came on. He left the company years ago but we have stayed in touch. He is a sweet ol guy. He came to visit the other day. At lunch, he said, ‘I don’t even recognize the department anymore.’ Then he started telling stories that started with ‘In my day.”

“That’s exactly right. The first sign of transformation is that you don’t even recognize what was.”

“His IT was providing tools. Your IT is building solutions.”

My friend nodded.

“But there is more,” I said. “Even the term digital transformation is giving way to the term business transformation. That’s the second sign. Language is different because the reality is different. Change has permeated, it’s expanded beyond a part to a whole.”

“I hadn’t thought of that.”

“Digital transformation and all that comes with it isn’t just a different way of doing, it is an essential way of being. How do we know? Because we think differently in light of technology.”

I let him sit on that for a second.

“Do you need another cup,” I asked. “Because I’m about to come in hot.”

He laughed. “Do you come in any other way? No, I’m good.”

“Alright then. Thinking-cap time.”

“The bridge between being conformed and transformed is in a renewal of the mind. As much as I would love to digress into the wonder of our brain, you get it - the brain can reorganize itself by forming new neural pathways.”

“Because of how I think, what once was can become a new now is.”

“That is mind-blowing.”

My friend chuckled.

Then I looked him in the eye and said, “That is why your CEO needs you. You have had to renew your thinking as a CIO or you would never have made it. You learned to think like the business. You learned to think like the customer. You changed the way your team works by changing their starting point and the way they evaluate success.”

“Most CEOs are being asked to increase the bottom line by keeping up with the changes. But that’s not transformation. Change is all around them. Economical. Political. Social. Generational. They are being tossed about on waves while being asked to keep the ship afloat and headed in the right direction while navigating storms and icebergs with crews that are coming and going.”

“No wonder they abandon ship” my friend smiled.

“Nice one. And the point is, they are abandoning ship because they are changing things without really changing anything.”

We sat in silence a bit.

“I feel like I live my life like that,” my friend whispered.

“Most do. And I want to talk about that. But what are you hearing that is helping you decide to quit or not?”

“Yeah. I don’t want either of us to quit. I’m going back to what you said earlier. Are we thinking differently or just being asked to do things differently?”

“Tell me more.”

“Scott, our company has been comfortable as a major player. We aren’t the biggest, but we are a great story. And I have had something to do with that.”

“But the Board is jittery. I think their mindset is that we have to keep up. Even with AI now, I’ve never had them coming to me like they are. And you are right, it’s in their questions. They are asking ‘What are we going to do?’ not ‘What does this mean for us?’”

“Good point,” I said. “In times of fear, boards manage back when they actually need to lead forward.”

“So what I am hearing you say is that the CEO and I need to step back and ask some questions.”

“Well, you know I love questions. Let me help you here if I may?”

“Please, that’s why I’m buying you this very expensive coffee.”

“It is good. This is for both of you:

  • Don’t change anything because of a new way of doing something. Change as much as needed because of a new way of thinking about something.
  • Think this way: What current states of being must change? How do we think about those things now and how must we think differently?
  • How is your e-credit? E stands for emotion and energy. Most leaders I know live on credit in those areas, and the debt is growing. Often, quitting is actually emotional and energy bankruptcy.
  • You are rarely reenergized by more of the same. And most change these days is just more of the same, like a new diet but the same faulty mindset behind it.

(My friend interrupted. “Hey.” I’ve seen him try several diets. I told him, “I love you, and I will keep telling you that if you don’t change your thinking about yourself and food then your diet will do little good.” I smiled. “You are conforming, not transforming.” He blew me an insincere kiss).

  • Your job as a CIO is to lead your CEO into right thinking. You did that. Your CEOs job is to lead your board into better thinking. 
  • Lastly, leadership is more acting upon than being acted upon. Leaders are quitting because the reverse is happening. Much of change is a response to being acted upon; transformation is acting upon.

(My friend again. “Ah. I was a little miffed at your diet reference. But I see what you are saying. I didn’t diet until my A1C was out of control. I was acted upon. But I’m having trouble because there is a bigger picture I need to see, something I need to be acting upon”).

“If your CEO is alone in this, if no one is willing to think about the issues and not just do things about the issues, it may be time to leave.”

“But if there is room for thinking, you both need to help the right people define the real conversation and ask the right questions.”

I asked my friend, “When CEOs leave, do you know what they do?”


“There is that. No, they go after things that could be different. They look for what they can transform.”

As we left, I noticed the sun felt warmer, and my friend looked lighter.

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