Why the Best Bosses Ask Their Employees to Work Less

Anthony Casalena, founder of Squarespace, recently gave a talk on minimalism and the process he uses to decide which ideas are worth pursuing, which should be tabled for later, and which should be thrown out altogether. The one part in Casalena’s talk that really resonated with me — and should for tech managers and executives — was this anecdote:

I remember…looking at the to-do list and going, "I don't want to do a single thing on this list. I don't care about this list anymore." I erased the entire list. So the whole board's gone. It's white. I think that what I was doing there was saying, “I just don't know if these things are really the most important things to work on anymore. If they are important, they'll come back, right?” I think the essence of this story is that it's very hard to reduce things. [...] If you're confronted with all these short-term priorities you can easily get locked into a path.

In other words: Reduce your to-do list.

These days, when most of us are plugged in 24/7 and being pulled in a hundred directions, that kind of advice can seem divorced from reality, or counterintuitive at best. It’s deceptively simple, and I’d argue it’s actually one of the most difficult things any of us can do. But, as Casalena discovered, it’s also incredibly important because one of the best ways to truly accomplish more is by doing less.

Work Less, Do More

Frankly, the approach Casalena used is one that I’ve been familiar with since my days as a consultant with McKinsey in the early 90s. Back then, Jon Katzenbach, one of my bosses, shared with me that he thought he could accomplish more in four days of work than if he worked all seven. Of course, in a highly competitive company like McKinsey, that would never fly. But Jon’s reasoning was sound — and his argument for working less was rooted in concern over the negative effects of working too much.

Specifically, when employees have the cushion of more time to do work, two things happen:

1. They procrastinate, which makes them less productive
2. They take on more work than is really necessary, which stresses them out and hurts their performance

In both scenarios, employees end up overworked and burnt out, and in extreme situations, they become totally demoralized. None of that is good — particularly for a growing company that’s desperate to attract and retain top talent.

A Different Way to Manage: Double Output by Cutting Workload

When I founded OpenView Venture Partners in 2006, I was fortunate enough to hire a lot of talented, super ambitious people. Without prompt, these people would put in late hours (often working nights and weekends) and accept every job thrown their way. As a boss, that might seem like a dream. But I knew better.

So, I decided to study my team’s productivity relative to their time worked and I began to notice a trend: for every hour they worked over 40 hours a week, productivity dropped. In fact, productivity peaked just under 40 hours a week. This led me to implement a new policy: No more working nights and weekends, and no more working on vacation.

At first, some were hesitant to actually work less. Some still worked weekends. But, they eventually got the message — sometimes because I would actually send team members home. The point I was trying to make was that working more hours wasn’t a sign of commitment, it was an indication that we had collectively failed to do three things: manage our time, prioritize the most important things, and see the bigger picture.

Prioritization and Focus Yield Productivity

The key takeaway here is that the best bosses push their employees to work smarter by working less. That’s what helped Casalena get past the lengthy to-do list that was keeping him from taking Squarespace to the next level, and it’s what helped my team at OpenView re-discover true workplace efficiency.

Now, culturally, this isn’t always an easy change to make. Your employees may think you’re bluffing or they may not fully buy into the idea that they can accomplish more in fewer hours. So, to help them get over these mental and cultural roadblocks, I suggest two things:

• Zero-base activities and focus on short-term priorities: The goal with zero-basing is to force people to scrutinize all of their activities and decide which ones really matter. This allows you to explicitly stop certain activities and create more time for the high-value activities that make a bigger impact. This works particularly well in agile environments for development, sales, marketing, and customer service. For more on that, check out this Slate post from Scrum founder Jeff Sutherland (disclosure: Jeff is an OpenView senior advisor).

• Force prioritization by overloading backlogs: If, for some reason, you can’t do the above, then you might try the opposite extreme — putting so many goals on everyone’s plate that they have no choice but to prioritize. When this happens, unnecessary activities will naturally shift to the bottom of the to-do list. As the boss, you can then work with your employees to eliminate tasks entirely or pass them off to someone else. This isn’t a perfect approach, but it works.

If you’re really desperate, you might also try Casalena’s approach: delete your team’s to-do list entirely and simply wait for the truly important work to re-emerge.

No matter the route you take, your ultimate goal should be to push your team to really hone in on the activities and goals that matter. And when this happens, employees will be happier, more productive, and more efficient — and you’ll be the boss they thank for it.

(Image credit: Andrés Nieto Porras & ihtatho)