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4DWW Challenge: 5 mentorship tips for the 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. 

A few weeks back, I told you about how the 4DWW was way more popular than you probably think—and a reader named Brianne responded with an interesting observation that I just had to share:

“I can get my work done in 4 days, and am a proponent of work/life balance. The challenge is that if I compress my work week, I don’t have time to mentor the younger associates at my company so they end up being the ones that miss out.”

This is a VERY common concern when it comes to the 4DWW. After all, a shorter week means less time for meetings and the day-to-day grind of work—and even less time for the hands-on and delicate process of mentorship and training. 

It’s not something to be taken lightly either. We know all about the value of great mentorship here at IWT. Our founder Ramit Sethi credits his mentor Jay Abraham with putting him and his company on the path to where it is today. So, really, we all owe a lot to good mentorship at IWT.

Ramit chatting with Jay Abraham

How to create transformative mentorship in a 4DWW

Mentorship can get easily lost in the shuffle when your business is trying out a new work system like 4DWW. 

Mentorship is crucial though—and it isn’t made any less important just because you’re working with less hours in a week. In fact, the development of our employees is so vital to the future success of the company, that we made sure to double down on mentorship and training when we went through the 4DWW

Today, I want to prove to you that it can be done using the very same systems that we use here at IWT. 

For this, I made sure to get the very best advice from IWT’s president, Gretchen Leslie, who’s helped champion the careers of dozens of people in and out of IWT. Not only does she know how to grow the rich lives and work of her employees, but she’s been doing it for years. 

Here are Gretchen’s 5 pieces of advice for assuring the most transformative mentorship possible while doing the 4DWW Challenge. 

1. There’s no “one-size-fits-all” solution

No two employees are alike. Everyone has different styles of working, managing their time, and overall career aspirations.

So why would a manager ever approach two employees with the same mentorship style?

“Even before the 4DWW, we realized that we needed to evolve with mentorship,” Gretchen says. “We realized that it wasn’t a one-size-fits-all solution—and we had to get much more intentional about it.”

That means sitting down with your employees and figuring out exactly how they want to be managed and mentored.

For example, Gretchen compares two employees under her wing: One loves to have frequent half-hour check-ins throughout the month in order to ask her questions and get advice, while another would take an hour or so every other week to go deep on the issues that they’re having. 

Before, both would have received regular weekly check-ins—but that would have been doing one of them a huge disservice.

People have really different needs and desires,” Gretchen says. “As leaders, a lot of times, we don’t actually stop and ask questions. We’re just like, ‘Alright, here’s how we give feedback, everybody gets a check-in, and then you get your end-of-the-year performance review.’ That’s what we thought it was—but that’s not the case.”

2. Don’t sweat the small stuff (especially in meetings)

When it comes to the meetings you do have with a person you’re mentoring, they need to be well worth the time. 

One common theme with the 4DWW Challenge is that all of IWT’s agendas are now incredibly streamlined. There’s zero fat in meetings regardless of whether it’s a one-on-one to discuss someone’s career or an all-hands to discuss a big annual goal. 

Put it another way: IWT is strictly a no “this could have been email” meetings zone. 

“When it comes to one-on-ones, it is not a time for status updates,” Gretchen says. “That is a waste of meeting time when we talk about things that could be written down. When we’re spending time one-on-one, I don’t want to talk about your projects. It should be coaching.”

These meeting times need to be intentional. You need to come at it with the goal of helping develop your employee’s long-term success—not short-term. 

3. Streamline your agenda

When it comes to how these meetings are run, it’s actually a very heavily guarded secret—one that takes years to master and only after you’ve gained the utmost respect of your peers and leaders of your industry.

Lol just kidding. Here is the exact agenda we use.

Want to build a business, but have no idea where to start? Get my FREE guide on finding your first profitable idea.

Feel free to use this agenda in your next meeting. (Click File > Make a copy first.)

While it might look simple, this is the template that has helped us streamline our meeting process down to an exact science. Not only has this led to some of the biggest wins in our company’s history, but it has also helped our employees get the most meaningful and actionable developments in their careers. 

It’s also helped us keep our 4DWW Challenge on track without sacrificing our employees’ development. Since each meeting starts with a fresh agenda, it means that there’s a record of progress—or lack thereof—for us to keep track. 

“The agenda is a really good starting point,” Gretchen says. “Where we spend most of our time is when I ask them, ‘Where do you need help and what would you like to learn?’ If there’s nothing and they say, ‘I’m not stuck. I’m really good,’ then we’ll cancel that week. We don’t need to meet just to meet, and everyone gets more time back.”

4. Championships are made in the offseason

One of the biggest insights that we’ve gained from the 4DWW is that a compressed workweek isn’t a magic bullet for your company’s issues. It’s not like employee morale will immediately shoot up, you’ll triple your quarterly earnings and hit the Fortune 500 list. 

The 4DWW actually amplifies what you are already doing: the good…and the bad.

“If you were bad at something before, you’re going to be bad at it afterward,” Gretchen says. “If you were good at something before, you’re going to be good at it afterward. The 4DWW completely amplifies it. Wherever you have cracks in your organization, to begin with, it puts them under a microscope.”

That’s why sports teams love the old chestnut, “Championships are made in the offseason.” You don’t just show up to the big challenge and expect to be great right away. Instead, it takes time and effort—often years of work before you settle down and actually tackle your big goal. 

IWT already had a great system for mentoring and meetings in place well before we even decided to research the 4DWW. When we finally decided to test it out, we were more than prepared for the challenge. 

“The really nice thing for us about the 4DWW is that it took places where we were already being very intentional and it caused us to double down on refining our processes,” Gretchen says. “So if we were already good at it, now we’ve become great at it because we had to be.”

5. Trust the process

The last point is an important reminder that change—good or bad—doesn’t happen overnight. With the 4DWW, we’ve certainly had our fair share of growing pains. 

However, if you stick with the challenge and already have the systems in place that have allowed your company and employees to grow, then we promise you will see results

“I cannot emphasize enough the growth that I have seen from my team,” Gretchen says. “We did a quarterly check for one of my long-time employees, and we both agree that she had the best quarter she has ever had. She has shown so much growth, so much development, she’s taking on such bigger projects, and her development into her career has been astronomical.”

(BTW if you’re interested in running an optimal quarterly check-in too, here’s a complete and detailed breakdown of our check-in process — AND a check-in form template you can use.) 

Not only that, but we’ve seen employee sentiment skyrocket since the last time we checked in with how folks are doing with the 4DWW halfway through the challenge. 

Weekly team ratings

As you can see, our employees are feeling well-rested, less stressed, and positive about the 4DWW across the board. This is despite a few down weeks here and there at the beginning of the challenge and halfway through.

As we continue to wrap up our challenge, we can’t wait to share with you what we’ve learned and whether or not we decide to continue with it. 

No matter what, though, this experience has proven to be incredibly valuable in not only stress-testing our company’s values, but also gleaning lessons about the aspects of training and development that we aren’t willing to sacrifice.

Remember: The things worth doing in life are rarely easy. But then again, sometimes that’s exactly what makes them worth doing. 


We’re coming to the end of the 4DWW Challenge—and with it, this series.

But there’s a silver lining: Next week, we’ll be working on gathering our thoughts and takeaways from the 4DWW Challenge. As a team, we’ll be voting on whether or not to continue on with a 4DWW… or just leave it as a fun and challenging test that taught us a lot.

As always, we’ll keep you updated on what we do—so watch this space. You’ll be hearing from us again before you know it.

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