4 Ways to Motivate a Team Through Failure

On an average day in Ottawa, scoops and cones and happy customers would all pour out of popular frozen treat spot Moo Shu Ice Cream. Business was good. Then, the pandemic hit. Before local mandates officially closed Moo Shu’s doors, owner Liz Mok did it herself, to protect the safety of her staff.

From supply chain woes to pandemic shut downs, any number of worst case scenarios can do serious damage to team morale. Keeping staff or partners motivated through the low points of your business growth can be challenging. But it’s a challenge worth overcoming—together.

What’s the worst that could happen? It’s a question many new business owners ask themselves as they take the leap to entrepreneurship. We spoke to Liz and several other entrepreneurs about their lowest moments running a business and how they stepped up as leaders to put people over profits, build trust, and ultimately keep their team motivation high.

Putting employees’ needs first: Liz’s story

As news of the spreading pandemic reached Canada in March 2020, fears among the Moo Shu Ice Cream team began to rise. “We have a larger percentage of Asian staff, who are more in touch with what’s happening in Asia,” says Liz. Like many places in the world at the time, Ontario was receiving vague or conflicting information from government leaders.

“To me, dragging out halfhearted measures will cost more than just sacrificing one week of sales,” she says. Rather than guess how to make the work environment safer, Liz closed the shop.

I’m doing literally everything that I can to make sure that working here is worth their while.
Liz Mok, Moo Shu Ice Cream

Since then, Liz made the choice to shut down three separate times during periods with high case counts. “I think people underestimate how stressful uncertainty is,” says Liz. In closing her doors, she hopes that she is sending a clear message to her staff: "You are more important than making a sale."

None of this strategy would have worked to keep morale high if Liz wasn’t already the type of leader who prioritized people over profits. What’s a non-negotiable when it comes to team motivation, according to Liz? “Better wages and better benefits.”

During closures, Moo Shu paid out any shifts that were already on the schedule. And, she worked individually with employees over the course of the pandemic to ensure that each person could balance hours and government benefits to make ends meet.

Paid breaks, paid sick days, and guaranteed hours are standard fare at Moo Shu, right alongside the handmade ice cream, pies, and dumplings. “I’m doing literally everything that I can to make sure that working here is worth their while,” Liz says.

Rolling with the punches (and leaks): David’s story

David Gaylord is Shopify’s Entrepreneur in Residence and the CEO of Bushbalm, a brand selling “skincare for everywhere.” After starting his career at Shopify right out of school, David entered an internal competition to build a business. Bushbalm started there with a $900 investment and has since grown to become a $10 million company.

From Bushbalm’s new headquarters (a space the company is already outgrowing), David shares that the journey hasn’t always been easy. In the business’s early days, an order of 10,000 bottles started leaking. “At the time, it was just the two of us,” he says. “It was like being painfully sad by yourself.”

If I jumped in and was like, ‘Here’s how we’re going to solve it,’ it would come across probably wrong. Because they probably know more than I do now.
David Gaylord, Bushbalm

Since that first major disaster, there have been others, including another batch of leaky products—but Bushbalm is a 10-person team now. More recently, an issue with the brand’s logistics and fulfillment partner caused an influx of more than 200 support tickets for a one-person customer service team. “Orders were actually getting lost in fulfillment in our partner’s warehouse,” David says.

Solving challenges at Bushbalm is a team sport. As always, they put their heads together to come up with a solution. “We slowed it down and then everyone chipped in to work on it,” says David, who himself was sorting Zendesk tickets to help ease the burden. But ultimately, he leaned on the support team who know their craft best to propose the solutions. “If I jumped in and was like, ‘Here’s how we’re going to solve it,’ it would come across wrong,” he says, “because they probably know more than I do now.”

Taking a team approach has helped Bushbalm’s staff stay motivated. “If there’s stress in the air, we just get together and talk,” says David. The team also syncs at the beginning of every week to reinforce the brand’s mission—and at the end of it to bond and blow off steam.

Learn more about how David and his team built Bushbalm from a $900 investment. 🎙 Listen to our 6-part podcast miniseries

Focusing on your Ws, not your Ls: Adam and Ash’s story

Designer Ash Edmundson and developer Adam Doeler are the minds behind Wrapped, an app that enables Shopify stores to add gift-wrapping options to product pages and shopping carts. The duo launched the app just in time for BFCM (Black Friday Cyber Monday) and prime gift-giving season. “We saw this insane amount of growth that went past the numbers we initially set,” says Ash.

While the couple expected a tapering off as the holidays approached, they didn’t expect sales to stop dead in their tracks. “Our growth completely flatlined for two months—no growth whatsoever,” says Adam. “That was super tough to wrangle with, mentally.”

Though Adam and Ash were only a team of two, the team dynamic had potential to implode under the stress. “We knew that we still needed to push through,” says Adam. The approach to team motivation? Shift focus away from the lack of sales and toward other wins. “One awesome thing we discovered was, even though we weren’t getting new merchants, we were retaining merchants,” he says. “And they were still processing orders with gift wrap.”

What we’re trying to do is find new data points. What are the things we can celebrate, if not sales?
Adam Doeler, Wrapped

They also reached a milestone in early January, crossing the 10,000 mark in gift-wrapped orders processed by their clients. “What we’re trying to do is find new data points,” says Adam. “What are the things we can celebrate, if not sales?”

The experience, while stressful in the moment, helped the pair learn about the business. They saw that gift wrap was still being used by customers after the holiday season. “We realized maybe it’s more of a marketing thing," says Ash. “And that’s a win for us.” Wrapped is working on positioning itself as more than a seasonal app. “We saw a good little bump right around Valentine’s Day,” says Adam.

Now that they know Wrapped will ebb and flow, they’re motivated to work hard so they can use this year’s post-BFCM downtime to take an actual vacation.

Building trust as a leader: Michael’s story

Serial entrepreneur Michael Perry is no stranger to hardship. He struggled to get investors to believe in him while pitching his first startup, but eventually built a company that would be acquired by Shopify. His current endeavor, Maple, a household management app for families, introduced him to a new set of challenges.

“You’re either fighting wars externally or you’re fighting wars internally,” says Michael. “I actually have now experienced both.” He admits that the latter is much more difficult to navigate.

There has to be a level of authenticity and transparency from the leader. It’s important to own that and really solidify trust.
Michael Perry, Maple

This time around, Michael had no trouble convincing investors. He did, after all, have a solid track record in the app space. It was team dynamics that put him to the test as a leader. After growing his team to eight people, it became clear that two of those hires were negatively impacting the happiness of the whole team.

“In hindsight, I made a series of really bad decisions and put up with the cancerous behavior for the sake of moving the business forward,” Michael says. Ultimately, the two people departed the company, but Michael was left with a morale problem. “A quarter of my company was unhappy,” he says. “I was doubting myself and doubting my ability.”

Getting team motivation back on track relied on Michael owning his mistakes. “There has to be a level of authenticity and transparency from the leader,” he says. “It’s important to own that and really solidify trust.”

What Michael also learned from the experience is that keeping a team motivated starts in the hiring stage. Now, he prioritizes hiring people excited for his mission and drawn to the all-hands-on-deck dynamic of an early startup. “Those people, in the hard times under good leadership, they actually really rise up,” he says.

Motivating a team by example

You can’t always predict what the next quarter or year has in store for your team. It might bring dizzying highs or frustrating lows. What you do have control over is how you lead and how you motivate your team throughout the ride. As these stories have demonstrated, it’s during these low moments that you really need your team to show up. And making that happen means showing up for them first.

Illustrations by Dan Page

Keeping Morale High Through Business Lows: 4 Stories of Perseverance

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