4DWW Challenge: 4 leadership lessons from 4DWW

This is part of our series on IWT’s 4-Day Workweek Challenge, where we take you behind the scenes to show what it’s like for us as we test out a compressed work schedule. The post you’re about to read is written by Tony Ho Tran, a professional journalist for The Daily Beast and a former copywriter for IWT. Join us as we dive deep on the highs and lows of the challenge. 

Early in my career, I found myself managing a small team of writers for the first time ever—but it was completely unintentional.  

I was writing for a small arts and culture publication (now defunct) based in Chicago. Things went pretty well—at least, for a while. I was a young and hungry writer, and more than happy to work with other young and hungry writers to get published.  

But then, disaster struck: The website completely crashed and we lost a year’s worth of content in one fell swoop. To add insult to injury, it occurred the night before we were supposed to cover a massive music event in the city. 

On top of ALL of that, we also didn’t have an editor or content manager at the time. At this point, I had two options:

  • Sit back, shrug my shoulders, and say, “Not my problem,” while the website burned to the ground and the event went uncovered.
  • Take point—and try to do anything to help.
Decisions, decisions…

That’s how I found myself in the unenviable position of rallying the writers to not only send me what drafts they had of their old work to rebuild the website, but also to cover the event that we were supposed to without missing a single deadline. 

After a sleepless night, along with enough coffee to kill an adult elephant, my team and I were able to get the site back up and running with some of the content that was erased. We were also able to cover the event—and I’m proud to say no one missed a deadline. 

Why am I telling you all this?

Partly because I’m feeling nostalgic. Mostly, though, it’s to highlight a big lesson I learned that day—and a core tenet at IWT and something we’ve learned a lot in the 4DWW Challenge: Anyone can be a leader. 

4 leadership lessons for a 4DWW 

Throughout the 4DWW Challenge, IWT hasn’t quite reached the level of emergency that my publication did all those years ago (please knock on your nearest wooden object until your hand’s sore).

But this summer-long experiment has shaped the way that its employees have had to manage their own workload and each other to make things work.

That’s because at IWT, we truly believe that anyone can be a leader. It falls right in line with two of our core values: 

  • We practice extreme ownership. That means collaborating and communicating with intentionality—and making sure to deliver on all our commitments.
  • We come to the table with solutions. We don’t just shrug and think, “Well, that’s not my problem.” Instead, we use our creativity to solve problems with actionable solutions.

The insights learned in this transition are valuable—and they really can’t be learned in any other situation. 

That’s why I talked to IWT President Gretchen Leslie about what she’s learned over the past few months of helping lead the team through the 4DWW—and what she’s seen the entire team do to lead each other as well. 

If you’re considering a transition to a 4DWW for your own business, and regardless of whether you lead a Fortune 500 company or a bootstrap operation from your garage, these pearls of wisdom will be incredibly helpful for you in the future. 

Lesson #1: Success happens before you start

One thing that has surprised Gretchen and a lot of other IWT employees is the fact that work has been relatively smooth throughout the 4DWW Challenge.

While you’d expect there to be a lot of growing pains and difficulty adjusting, the team took to the challenge head-on and has been more than willing to remain flexible and nimble through a major transition.

A lot of it is due to the fact that the team is filled with top performers in the first place. 

“From a leadership perspective, it’s been absolutely seamless,” Gretchen says. “I don’t have to do a whole lot because this company runs itself. We hired great people and they just do their jobs.” 

When considering this for your own team, ask yourself: Are the right people in the right positions for success? If your team isn’t already primed for it, it’s not going to go well. If your company has cultivated the right folks for your business, then the transition to a 4DWW will be so seamless, you won’t see it disrupt the bottom line one iota. 

Lesson #2: Pump the brakes

One thing that we’ve talked about over the course of the 4DWW Challenge is how intensity has picked up when it comes to IWT employee workload—which makes sense. Instead of having five days to finish up work, folks now have to squeeze everything into four.

That includes meetings, answering emails, and all the admin work that needs to be done ON TOP of actual work. 

A more intense workload plus less time is a perfect recipe for the dreaded B word: burnout

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That’s why it’s so important to recognize these signs as a leader—and nip them in the bud.

“We have a very hyper-successful culture at IWT where nobody wants to disappoint anybody else,” Gretchen explains. “So I have to remind people that, while it’s not necessarily okay to just randomly miss a deadline, it is perfectly acceptable to say, ‘Hey, I’m really over-allocated today. Instead of delivering this today, can I get it to you next week?’”

Part of this requires an acute awareness of your team’s stress and happiness levels. If you’re not in tune with where they are with their work, you might end up missing the signs of burnout—and that could end up hurting everyone. 

A big part of addressing this boils down to communication… which brings us to:

Lesson #3: Normalize asking for help

Communicating this to your team is crucial. You need to make them aware that it’s not only okay to ask for help, but encouraged. This will go a VERY long way in fostering a healthy work environment—and a successful 4DWW trial. 

“Asking for help is not a sign of weakness. It’s a sound sign of actually being really self-aware,” Gretchen says.

She added that it’s vital that you’re able to instill this message into the bedrock of your company’s culture. If not, you might easily end up with dissatisfied and constantly burned out employees. 

It’s one thing to talk about it, though, and a whole other thing entirely to do it yourself as a leader. But, when you practice this value, they become more than just some hollow words about cOmPaNy VaLuEs written on a dusty HR document. They become real. 

“That’s a very powerful message when you see your boss saying, ‘I also am having a hard time with this and need help,’” Gretchen explains. “But I think that normalizes the fact that we’re all learning together and can rely on one another.”

Lesson #4: Embrace intentionality

While you want to make sure that your team is happy and not overworked, you also want to make sure that what time they are in the office is used to the best of their ability.

That starts with intentionality. Once you make it clear to them what the business’s goals are, they’ll be able to get a sense of how they should prioritize their work to achieve those goals. 

“IWT employees all have that intentionality before they just sit down to work every day,” Gretchen says. “They spend a moment and they think about, ‘What is my high-value activity? What do I have to get done today? And what if it doesn’t get done?’ They really are great at figuring it out, focusing on the high-value priorities, and knowing what’s inevitable and what won’t get done.”




One thing you might notice about all these lessons is that they can be applied to many facets of life beyond the 4DWW. That’s the beauty of this challenge. As Gretchen says, “There’s no silver bullet.” 

The things that make a business successful or unsuccessful at the 4DWW are the very same things that make it successful in any other scenario. It’s the same nuts-and-bolts lessons that every leader should have when leading a team. 

Remember: Anyone can be a leader. Luckily, the things that make you a good leader in good times are practically the same things that make you a good leader in tougher times

“It’s all the things that make you great at working well,” Gretchen says. “This is just a crucible for really refining those skills. Even if we stopped the 4-day workweek tomorrow, I think we would all be better for what we’ve learned from doing it because it makes us so mindful and thoughtful about how we work—and that was really one of my goals with the 4-day workweek. It really pushes you to be intentional in how you work.”

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