Why Most CEO Time Management Advice Fails

Olenka Cullinan grew up the daughter of a serial entrepreneur in Russia. Her mom ran a manufacturing company and grew it to more than 300 employees, becoming a model for business success.

But when it came to successful parenting, that was a different story.

Cullinan remembers rarely seeing her mom, other than for a quick kiss goodbye in the mornings. It was her mom’s driver who often took Cullinan to school or to after-school activities. But Cullinan wanted more time with her mom. So, when she was 5 years old, she decided to find help.

She turned to the North Pole.

“I wrote a letter to Santa asking for my mom,” Cullinan says. “That should tell you how little time we were spending together.”

Cullinan’s plea didn’t work, but as she got older, she became more interested and involved with her mom’s company. She started working alongside her mom at the age of 14, and over the years, the two grew closer. But Cullinan told herself she would never be absent from her own child’s life the way her mom was absent from hers.

Fast forward to 2017, and Cullinan herself was a budding entrepreneur, often flying all over the country while her toddler daughter grew up at home. She woke up one morning to a text message recounting her daughter learning to ride a bike, and she remembered her letter to Santa.

“It was supposed to be different,” Cullinan says. “How am I in the same station where my business looks successful publicly, revenue is growing, and we are growing, but I’m now missing my own daughter’s milestones? That was a big wake-up call for me.”

The next year, Cullinan founded iStartFirst, a company built on CEO time management systems and fundamentals that help leaders transition from being a bottleneck to leading a company that runs without them. Her daughter is 10 now, and Cullinan proudly says she’s attended about 98% of her daughter’s volleyball, dance and other club activities over the years.

“I know what it’s like for so many CEOs who are trying to please everyone, who try to accommodate their business and their loved ones,” she says. “I am now the walk-the-talk kind of gal who proves that you can actually do both. You can run a successful business and also be a parent.”

Why Traditional Time Management Advice Falls Short

To get where she is today, Cullinan had to realize that most CEOs, including herself, aren’t necessarily bad at managing time. Where they struggle is allocating it effectively. Traditional time management advice — calendar hacks and encouraging inbox-zero practices — focuses on efficiency. However, time shouldn’t be about efficiency for CEOs.

Time should be about strategy.

“For CEOs, the goal is not zero tasks,” Cullinan says. “The goal is the vital tasks that actually move the company forward. The goal for a manager is execution. The goal for a CEO is more about vision and looking for people who can execute really well. Strategy and execution are very different things.”

Gideon Malherbe agrees.

“Few people become CEOs without first succeeding through the ranks,” says Malherbe, founder of Virtual Consulting International, a firm focused on strategic management, transformation, and innovation. “As a result, they generally have more confidence in tried-and-tested operational activities than in the ambiguity and uncertainty that comes with the CEO role. They are therefore prone to drift back into what they know best.”

Strategy work also doesn’t yield the immediate results seen in operational work, another reason Malherbe believes so many CEOs veer away from strategic responsibilities.

Malherbe remembers a two-time CEO he worked with who struggled with this dynamic. The CEO’s days were flooded with meetings, from breakfast get-togethers to evening commitments. As a result, his focus was often “in the business” rather than “on the business.”

“While he was successful in many ways, he failed to make enough space to really appreciate the game-changing opportunities available to those businesses,” Malherbe says. “He didn’t have the time to absorb the broader industry dynamics around him.”

The Hidden Cost of Time Misallocation

Time misallocation is a common problem for CEOs. Cullinan says she hears it firsthand whenever she speaks at conferences or sits down with a fellow CEO. On average, the CEOs she interacts with spend 65-70% of their time in the trenches doing busywork, or what she calls “$2 tasks.”

The reason for this, she believes, is that most CEOs fall victim to wanting to be everyone’s hero.

“They’re solving everyone’s problems, they’re carrying the company, they’re providing solutions, they’re everyone’s person, and everyone wants their time,” she says. “If we give that time to solve everyone else’s problems, we essentially have no time to solve things that are actually moving the needle.”

She believes that 65-70% of a CEO’s time should be focused on strategy — the big-picture thinking that can actually help propel a company forward.

Malherbe argues that the time a CEO devotes to strategy ultimately depends on the organization’s structure and managerial maturity.

“A company with weak policies and procedures will remain heavily dependent on the CEO for day-to-day decision-making,” he says. “That leaves very little time to reflect on external forces. A company with stronger systems and processes can focus more on efficiency and effectiveness, creating room for the CEO to spend more time on external industry dynamics and key vendor and customer relationships.”

Organizational maturity also requires CEO maturity, Cullinan explains.

“A lot of CEOs I’ve worked with are really great at delegating tasks, but they’re not good at delegating outcomes,” she says. “(Delegating an) outcome is when you transfer a decision over to someone else, and that is something that a lot of CEOs struggle with.”

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The Hidden Cost of Reactive Leadership

When CEOs don’t give themselves time to be strategic, it means their leadership becomes reactive. Reactive leaders end up overseeing reactive businesses.

“The current healthcare industry is built on reactive medicine — fixing damaged people,” Malherbe says. “Reactive leadership is the same. It is responding, in a positive sense, to what has already happened in an attempt to minimize damage or encourage success. Although experienced as contributing, it fails to build capabilities for future success.”

When CEOs complain to Cullinan about how busy they are, her guess is that they are reactive leaders — and she is almost always right. She calls this the firefighting approach to leadership.

“They only lead from current situations, solving problems and putting out fires,” she says. “They’re basically playing into what’s happening right now and dealing with situations as they’re already here. They don’t have time to future lead.”

How to Reallocate Time Like a Strategic Leader

So, how do you future lead?

Cullinan says it starts with a CEO’s calendar. In her experience, there are two types of CEO calendars: one filled with meetings and to-dos, and one completely blank.

That first calendar “looks beautiful and color-coded and coordinated, but I call it ‘Instagram versus reality,’” she says. “Their reality looks nothing like their calendar. They ignore things, and they push off their own doctors’ appointments, vacations, and time off.”

Leaders with blank calendars are “flying by the seat of their pants,” Cullinan says.

Being a proactive leader requires allotted time to be strategic. That means CEOs must reserve “white space” time on their calendars to think. Once the time comes, they need to be ruthless in protecting it and taking advantage of it, Cullinan says.

“This is your No. 1 most expensive resource in the company,” she says. “Just like you protect the dollars that you allocate in your budgets, this calendar space is exactly the same way.”

Malherbe believes leaders must use that white space time to plan for multiple potential futures rather than simply reacting to the past.

“Leadership is, in essence, crafting a picture of the future,” he says. “To shape that picture effectively, a CEO must invest time in developing the ability to craft relevant and credible narratives about what may happen next.”

Doing so requires a willingness to devote time and energy to thinking “outside the box,” according to Malherbe. That is exactly why the priority for CEO time management must be on strategy.

“The world does not deliver major shifts on a schedule,” he says. “It comes at us spontaneously and unexpectedly. That is why a CEO’s time cannot be managed only around efficiency. The CEO must also make room for awareness, reflection, and interpretation.”

The Role of External Perspective in Time Discipline

If you need time to think, plan, and strategize, Vistage can provide the space to do so.

Vistage peer advisory groups help CEOs step back from the day-to-day demands that consume their time and refocus on what matters most. Through peer advisory groups, executive coaching, and shared insights from leaders facing similar challenges, CEOs gain the clarity and accountability needed to make better decisions about where to invest their time.

The result isn’t just greater efficiency, it’s stronger leadership and more sustainable growth — without needing help from Santa Claus.

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