What it Takes to be a CEO: Adapting, Delegating, and Letting Go

This is the second part of a three part series. You’ll find Part I by clicking here

In his now famous 2012 Wellesley High School graduation commencement address, David McCullough Jr once said, “even if you are one in a million, on a planet of 6.8 billion, that means there are nearly 7,000 people just like you.”

Although McCullough isn’t wrong in the literal sense, his assessment of the uniqueness of human achievement is not altogether accurate. After all, someone always has to break the barrier. There is a “first person” on the moon, only one inventor of the lightbulb, and a “first” to summit Everest. McCullough’s statement speaks to the implausibility of human differentiation, not to its impossibility. The executives I interviewed in my exposé on the position of Chief Executive Officer are living proof of that conclusion. Extraordinary achievements are recognizable, even in a world full of them. How do you go about differentiating yourself? In the words of CEO’s: adaptability, delegation, and the ability to let go.


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Rarely, if ever, has there been a point in modern human history where CEO’s have had to adapt faster than they do today. Just look at the remarkable, albeit difficult to explain, exponential rise of cryptocurrencies, artificial intelligence, or robotic process automation. These rapid developments, in conjunction with the instability of the current geopolitical landscape, require an almost unprecedented level of adaptability.

“The CEO’s job changes so often, you have to be comfortable with change. Once you stop learning, you stop being adaptable,” said Tien Tzuo, CEO of Zuora, Inc., the Silicon Valley enterprise software company.

Which companies are the best at adapting? Often it is the companies that are run by their founders and the entrepreneurial culture they can provide. As “an entrepreneur when you are running a bigger and bigger company you have this, almost maniacal, desire to be nimble as a start-up. You are trying to inject that back into the culture of the company and I think there are a lot of positives to that,” said Tzuo. “That’s why you see some of these larger companies, like Facebook and Google, where they try to be innovative and create new things. These founder led companies have a little bit more of that founder innovative culture to them.”

That culture allows companies, and their CEO’s, to adapt quicker to macroeconomic or industry driven changes. It’s also why malleable tech companies, particularly those in the more mobile service-oriented space, have flourished in the fluid business state.

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 Delegation and Letting Go

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The ability to shift job roles vertically in order to further expand firm capacity, and to effectively prepare for a future without the CEO, is one of the primary distinguishers between good leaders and extraordinary ones. However, even great leaders face personal struggles in the difficulty of letting go.

“When a company is small you are used to dictating things and getting your hands dirty. You get involved in everything, but at a certain size you realize that doesn’t work. You are undermining folks and the company is bigger now. You are no longer the expert,” Tzuo said.

The process goes much deeper than simply transitioning job roles to subordinates, there is also a need to – at times – step away from a project entirely.

“You know the projects that you used to get involved with went well. Now the projects you care about, they don’t go well. Why? Why is it that every project I get involved with doesn’t seem to go well? All of the sudden people that have been in the company a long time start to resign. The realization that you are a big contributing factor to that, and how you are managing, is one of the keys. Once you can see the connection between the organizational issues and how you are managing, then you can start to find solutions to the problem. The nirvana is that you helped set up the organization where people can do their best work on their own volition,” said Tzuo.

A critical part of the delegation equation is the quality of the people a company hires.

“If you have done a good job as a CEO, especially something that has scaled, you have also gotten much, much better at hiring a senior leadership team made up of people that are super capable and people you can trust,” said Kevin Akeroyd, CEO of Cision. “Then you can delegate more.”

A CEO’s development is never really finished, some education coming at the latter part of one’s career, and other tidings even later.

Dennis Chookaszian, former CEO and Chairman of CNA Insurance, learned his lesson after retiring from his position as CEO.

“I stayed on the board for three years after I retired. One of my mantras is don’t do that,” he said. “After I retired, Jack Welch retired and he wrote a book saying when you are done get off and get out. Don’t serve on the board. If I had thought about it correctly I would have gotten off of the board.”

There are many great CEO’s, and inherent in a number of them is the drive to continue to control, to continue to lead. A core lesson is the difference between the words “control” and “lead”—two fundamentally separate actions that often lead in polar opposite directions. Even great CEO’s can fall victim to the need to control.

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“When I was younger I had all of the answers, but now I rarely do anything without consulting with somebody I consider to be a real expert,” said Michael Keeler, CEO of Lease Accelerator, Inc.

“Part of it is discipline, but part of it is humility. If I have a real decision to make that has very high consequences I want to de-risk that decision by getting as many different views as I can so I make the best decision that I can.”

In other words, lead.