What’s The Worst That Could Happen? A Fun Way For Your Team To Face Their Fears… Together

David Horning
4 min readDec 3, 2020

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RIP to a true example of leadership (Source: KTNV Las Vegas)

What if everything — and I mean everything — that could go wrong did go wrong? When rolling out a new policy, adapting to new rules and regulations, or getting used to a new executive, there is bound to be just a little bit of fear. As we limp into 2021 after a 2020 that nobody — except for maybe a tiny bat in China who dreamed of world domination — saw coming, there’s going to be some battle-weary soldiers in the office, so when you announce another change, resistance will inevitably kick in.

Don’t resist the resistance unless you want more resistance. Instead, embrace it.

In 2014, online retailer Zappos decided to shift their management model to a holacracy, a management model where the traditional functions of managers are eliminated and job titles are replaced by roles that individuals acquire. The traditional pyramid of hierarchy is replaced by, according to Business Insider:

A series of “circles” dedicated to specific functions like marketing and customer relations.

It’s centered around self-management and requires employees to have high levels of engagement, meaning, and organizational buy-in to work. Say what you will about the management model, what I’m more interested in is how the employees and executives at Zappos, as well as outside experts, responded to such a seismic shift.

How did the employees respond?

When former CEO Tony Hsieh sent out a memo asking for full employee commitment to the new system, 18% of the company chose to take their severance packages. Yikes.

How did outside experts respond?

In the never-ending quest to prove that new ideas don’t work, publications like HBR, Inc, and Business Insider were quick to draw attention to the mass exodus from Zappos.

How did Zappos executives respond?

They made a video spoofing the idea of a holacracy. You read that right: Hseih starred in an employee-produced video where he falls asleep on the couch, and wakes up in a dream where the company has fallen into the chaos of anarchy, like the press predicted (watch the video HERE).

https://vimeo.com/139618687

This video was a fun, outside-of-the-box way of communicating to the remaining employees that even if the new management style didn’t work, it could always be worse. Though Zappos has gradually transitioned away from holacracy, the switch didn’t involve panic or a coup like the video portrays, and the company has maintained a positive, creative workplace culture that consistently shows up on best-places-to-work lists.

So what was the point of the video?

It served three purposes:

  1. It allowed for employees to work together in a creative setting, side-by-side with the CEO and one another, on a fun project they could look back on, be proud of, and share with family and friends that “My job and my boss are pretty cool.” Be honest: would your boss take part in a video spoofing his own decisions?
  2. It gave employees a shot of perspective. When faced head-on with change, humans have a bad habit of gravitating to worst-case scenario situations. One way to ease this stress is to take that worst-case scenario and manifest it in the form of a fun project like this that delivers the subconscious message, “Relax — that worst-case scenario is not only implausible, it’s kind of silly.” Using humor in this way is a great tool for level-setting perspectives, so instead of stress and fear, people begin asking the question, “What can we do next?”
  3. It delivered a message to outsiders: this is a fun and engaging place to work. Imagine you’re looking for a job and you’re deciding between the “business-as-usual” company and the “we don’t take ourselves seriously” company. Though the former is consistent and you’ll feel safe and secure, the latter is one of the biggest online retailers in the world because it takes risks, has fun, and is willing to take an occasional L. Would you rather work at a company that takes work seriously, takes its customers seriously, and takes itself seriously, or a company that takes its work and customers seriously, but doesn’t take itself seriously.

If you’re a leader, making a short video to poke fun at your own ideas is one way to help your team want to get on board with new ideas, instead of making them feel like they have to get on board. Added bonus: the video that Zappos made cost zero dollars and was put together exclusively by team members. Sure, the editing, sound, and writing isn’t award-worthy, but it’s okay because the people who made it aren’t professionals. Because of the fundamental shift of workplaces we experienced in 2020, we need to find new ways to generate buy-in from our teams, and making a video where you communicate that “Yeah, this could go wrong, but with you by my side, we can make this thing work… and if it doesn’t, then at least it won’t be as bad as what happens in this video,” is just one way of many to do it.

Note: I wrote this in response to the loss of a visionary risk taker and leader whose legacy will live on in all those he inspired through working for him, reading his book, watching his interviews, and so on. If more leaders modeled their behaviors after Tony Hsieh, we’d fundamentally change the meaning of what it means to “work:”

“I think when people say they dread going into work on Monday morning, it’s because they know they are leaving a piece of themselves at home. Why not see what happens when you challenge your employees to bring all of their talents to their job and reward them not for doing it just like everyone else, but for pushing the envelope, being adventurous, creative, and open-minded, and trying new things?” — Tony Hsieh

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David Horning
David Horning

Written by David Horning

Teaching leaders to develop their sense of humor and make work more human.

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