In 2006, after I'd written an article about outsourcing R&D, I received a reader email seeking sources for a book on mobile lifestyles. My correspondent, a guest lecturer at Princeton, wanted to know whether I was aware of any "employees who have 'outsourced' themselves to create more time in their lives? In other words," he wrote, "have you heard of any employees who have paid a freelancer to perform their job function unbeknownst to the boss?"

I had not, and I wasn't able to help this unknown person. Some guy named Tim Ferriss.

A year later, of course, Ferriss shot to fame with The 4-Hour Workweek, his have-your-cake-and-eat-it-ideally-on-a-beach-in-Aruba bestseller about upending the relationship between time and work. The book resonated powerfully with entrepreneurs, famously made twitchy by the word delegate.

Back then, startup entrepreneurs typically had no one to delegate to. Today, founding teams are no bigger: In fact, a growing number of companies have no employees. But now there exists a slew of devices, services, and platforms eager to unburden the core competency that is you. Productivity tools organize you, facilitate tasks, or--thanks to the gig economy--lift whole responsibilities off your plate. The dividend they pay is time.

In Ferriss's philosophy, freed time should be used for living: ideally buff and large. But for many CEOs, time--like profits--is best plowed back into the company. More time enables entrepreneurs to work, as the saying goes, on the business rather than in the business. As the company scales, that freed time creates opportunities to concentrate on complex, open-ended issues such as strategy, innovation, culture, motivation, and vision.

The earlier, blocking-and-tackling stage of entrepreneurship lends itself to traditional productivity measures. Many tasks required to launch a company typically fall under what Reb Rebele, a professor of people analytics and applied positive psychology at the University of Pennsylvania's Wharton School, calls "decomposable problems." Such problems "are best solved by breaking them down into constituent parts and tackling those parts one by one," says Rebele. "A lot of productivity tools are built around that."

By contrast, the high-level work of CEOs is less decomposable. Does that mean leaders pursuing the big picture must think differently about productivity? Yes and no, say the experts.

When an entre­preneur acts alone or as part of a tiny team, her individual productivity is essentially the same as the company's productivity. In a business's early days, the metrics are straightforward: "Today, I followed up on 10 sales leads and talked to three bankers and negotiated a lease for an office." It's a way of working that suits many entre­preneurs, says Peter Shankman, author of Faster Than Normal: Turbocharge Your Focus, Productivity, and Success With the Secrets of the ADHD Brain.

Shankman is an entrepreneur himself--he is the founder of Chicago-based HARO, which matches journalists with sources. The connection between attention deficit hyper­activity disorder--Shankman characterizes the condition as having a "faster brain"--and entrepreneurship is well documented. (Many founders claim it as a badge of honor.) "An entrepreneur's mentality is 'I can do everything! I can run everything!' " says Shankman. "And it works, because they have 12 plates spinning in the air at one time."

Entrepreneurs--like most people--also thrive on completion. "Checking things off a list creates dopamine in your brain," says Shankman. "You get a little rush. 'Excellent! I finished that!'"

As a business scales, however, the nature of the job changes. The founder's personal productivity no longer equals the company's progress. Instead, the founder must internalize the company's goals as her own. Those goals are bigger and take longer to achieve, and progress toward them is often harder to measure than anything one person can accomplish. Imagine putting a check mark on your to-do list beside "develop culture" or "formulate vision."

The slower, more deliberative approach that's required may appeal less to entrepreneurs, says Shankman. Fast-brained people, he says, "have two types of time: now and not now." Tasks that unfold over long periods with no defined deadlines qualify as "not now," and that can devolve into "never." Shankman recommends doing something--anything--to turn far-horizon responsi­bilities into present-moment work. "Open up a document and put down some words," he says. "It's a start. And you need to get something done and get that feeling of completion."

Entrepreneurs are also big on control. That impedes their ability to delegate--among the greatest determinants of CEO productivity, says Robert C. Pozen, a senior lecturer at MIT's Sloan School of Management and the author of Extreme Productivity: Boost Your Results, Reduce Your Hours. The CEO "may in fact be the best person to do a certain function, which makes it hard to give it up," says Pozen. "But it is no longer productive for the company or for them if they do it." The best question the leader can ask himself: "What can only you, as the CEO, do?"

At the same time, delegating means dealing with people, "and that is inherently messier than doing it yourself," says Pozen. In some cases, managing someone you're delegating to can itself take a toll on your productivity.

Pozen suggests that, rather than look to completed tasks, the CEO internalize indicators of his company's success as metrics for his own performance. "Is the company able to recruit and retain good people? That says a lot about how you are doing personally," says Pozen.

Once they have established their own productivity practices, CEOs should turn their attention to the practices of their employees. "Things like no emails between this hour and this hour, and this is the maximum number of people who should be invited to meetings," says Dan Ariely, a professor of psychology and behavioral economics at Duke University, and co-founder of the productivity startup Timeful, since acquired by Google. "The job of the leader is to make people better than they are naturally," says Ariely, "and that includes helping them with this."

If productivity were a comic strip, the supervillain would be distraction. More has been written about managing email and social media than about the meaning of life. A whole category of productivity tools corrals wandering attentions.

CEOs are certainly not immune to the social siren. But some suffer from the opposite problem. They are so consumed by their companies--their creations--that they become hyper­focused while the world around them recedes. And that can be detrimental. Great leaders have lively minds: They are curious and empathetic. Engaging widely with the world, not bound by an agenda, they think the big thoughts that produce genuine change.

In the '90s--before the universe coalesced at our fingertips--I visited a library-supply company in Wisconsin whose CEO practiced something he called "universal scanning." Staff members regularly pulled intriguing articles from a vast array of publications and pinned them to the walls of a room. Periodically, the CEO would enter and spend an hour or so simply browsing through the headlines. The practice, he said, broadened his frame of reference, inspired unexpected connections, and heightened his creativity. Distraction--or exposure, as he thought of it--made him better. "The enemy of productivity is that the world is really interesting," says Ariely. "Having lots to do and think about is a blessing."

And, yes, technology can create space to indulge that blessing. My onetime correspondent Ferriss's research on outsourcing eventually morphed into chapter eight of The 4-Hour Workweek, in which he recommends that employees hire remote personal assistants to handle scheduling, research, and online errands. Having someone in India handle the grunt stuff, he says, is not an expense but rather an investment, as it "frees your time to focus on bigger and better things."

There's another advantage to this tech-enabled outsourcing for any founder. The ability to "manage (direct and chastise)" your virtual aide, writes Ferriss, "is also a litmus test for entrepreneurship."

From the Winter 2017/2018 issue of Inc. Magazine