CIO Leadership

When CIOs Run Into Old School CEOs

Old-school CEOs need to be re-educated by CIOs who only know how to be lifelong learners, innovators and adaptors. The key is understanding the difference between mindset and mentality, between what they view and how they see.

Joe Woodruff


May 4, 2023

“You just took one in the jugular, man.” Old School movie

In the past few CIO Mastermind meetings, one phrase has come up more than others: “They are old school.”

Usually, it’s been in the context of dealing with remote worker policies, and specifically, the “everyone should be in the office” mentality.

But it isn’t limited to remote work issues. I have a CEO friend who is so old school he makes Southwest Airlines look progressive. 

I understand old. I’m in the latter part of my career. I date back to typewriters with miracle erase-tape. I used landline phones with cords that were forever tangled. Our kitchen appliances were avocado to contrast with the orange shag carpet.

I remember when dad brought home a color tv to replace the black and white. Exercise was dad telling me to get up and change the channel. President Nixon visited my hometown. 

Old can be nostalgic: I remember my Brady Bunch lunch box with fondness. Old car shows, antiques and collectibles are dear to our hearts. 

I recently stood in the checkout line at the grocery store (which is becoming an old way of shopping). I waited as the woman in front of me wrote out a check. Old can also be annoying. 

But old is not necessarily old school.

Mindset vs. Mentality

In psychological terms, a mindset is the combination of beliefs and attitudes a person possesses. Your mindset is what you view about yourself, others, expectations and circumstances. We talk about fixed mindsets and growth mindsets.

A mentality is how you think and a pattern of behavior that emerges from it. Mentality is a mode of thinking. I see it as coming in a mold, like those brightly colored jello molds my mom used in our avocado-colored kitchen.

When we talk about old-school, we are dealing with mentality, a mode of thinking reinforced by past effectiveness, proven patterns, and reliable, sometimes nostalgic, ideas and ways of doing things.

When how you think runs up against your CEOs old ideas and ways of doing things, you can take one in the jugular. It isn’t good. 

Remote work is a good example. I remember the day in which I could drop into someone’s office and see how they were doing and talk about what they were working on. Unplanned conversations were gold for developing leaders. 

I also remember impromptu lunch invitations or coffee breaks in which employees felt honored that I would take the time, and in which a staff member would go home and tell their spouse about the opportunity they were able to have with me. I was doing with them what bosses had done with me. I fit the mold.

I like being around people in the office. But that’s not the point. Mindset is focused on the priority of encouragement and development; how it happens is contextual. That it happens is non-negotiable.

Mentality is fixed on  ways in which one has previously developed and encouraged others; how it happens is non-negotiable. That it happens is negotiable. 

You could add so many more examples; how we hire, how we evaluate, why we promote, how we report, what decision making looks like, and so on.

School Is Out

When what was wise becomes what is foolish, you are in old school.

You have seen your CEO play the fool. You don’t want that for them, for yourself or for the company.

What do you do?

One, break the mold. You break a mentality by promoting a growth mindset. Remember, mindset is what you view about yourself, about others, about expectations, and about circumstances. 

It’s time for your CEO to have a new view. 

Leaders hopefully keep growing through four stages: Doer, Boss, Sage, Lover. 

You have seen this in renowned and respected CEOs. After the Boss stage, in which they made an impact and name, they become a source of wisdom with a heart to give back. But that is not the end. If they fully mature, they influence others by their presence, by their kindness, and by their generosity. They are usually a gentler version of themselves.

You have to remind your CEO that they have grown. “How are you different today from (a role they had, a time period, before a significant event in their life)?”

We live in our places of affirmation. That is why you and I get stuck. We are supposed to move into new places of affirmation. But it isn’t always a sure thing, so we hold on or go back to versions of ourselves that people applauded. 

Similarly, we talk about generational differences for a reason. It’s not enough to think we know people; we need to know generations of people. There is a line in Jewish history about one of their tribes: “They understood the times and knew what they should do.”

The CEO needs to be involved in conversations about why changes are taking place in generations, not just what the changes are. You get to lead that conversation. 

CEOs have an internal compass to lead forward and not manage back; it’s what has made them effective leaders. Significant change throws their ideas and ways of doing things off-course. They hold on when they need to move on. Helping them to set expectations based on current realities, and to respond to circumstances based on legitimate needs, is your part in helping them navigate change. 

Second, inspire rethinking. In breaking the mold, you are reshaping what they think. Here, you are rewiring how they think. Old school CEOs graduated from “teller” school; they were problem solvers who relied on persuasion, politics and presentation to get their way.

All of which they were prepared for. Catch them unprepared. 

Old school CEOs look for a good quote. If you say something they liked, you hear, “That’s good. I’m going to use that.” 

You want to engage differently. You want to hear them say to you, “That’s a good question.”

You rarely win trying to get your old-school CEO to change what they think; you will win if you can change how they think. Questions over quotes.

What is the outcome? What are the obstacles? What are the opportunities? What are the options? What is the one thing that will make the most difference now?

Every year, a small town I like hosts an event called Lost In The 50’s. Old car collectors ride into town to show off their classics; 50’s music is performed live; the community dances into the night. It’s a great and wonderfully nostalgic event.

I wake up the next morning and I am no longer lost in the 50’s. I’m back in the present. My phone is cellular. I still plug it in to charge, but the cord is not twisted. My kitchen is colored in soft tones. My carpet is finely woven. 

I don’t mind visiting the past. I have good memories. But I must lead in the present. Old-school will only make me an old fool. I have been taught better than that.

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