Harry’s Billion-Dollar Deal Went Bust This Year. But Covid Held Even Bigger Leadership Lessons

While Harry’s co-founder and co-CEO Jeff Raider has led his New York City-based company through industry disruption and landing–and then losing–a $1.37 billion aquistion deal, the Covid-19 global pandemic has been one of his biggest tests of leadership yet.

“I think we underestimated the importance of personal connection,” Raider said about working remotely this year in conversation with Tom Foster during Inc.‘s latest Your Next Move stream event. “It was just hard. We felt people really struggling on a personal level. We weren’t there to support each other.”

Not being able to connect in person has been the most difficult of all his challenges this year, Raider said, noting that a leader’s job is to find the time to connect with employees directly. For him, that meant meeting with employees one to one whenever he had a 30-minute opening on his schedule to ask questions like, “What’s bothering you?” or “What support do you need?” After all, asking directly is the most effective way to find the answers you need to be a better leader and a successful founder.

Raider, who has been a trailblazer in the direct-to-consumer retail category as co-founder of Warby Parker in 2009 before founding Harry’s in 2012 with Andy Katz-Mayfield, said that Covid-19 was only one of his worries as a leader this year–there was also racial inequality and a heated presidential election to address. And, there was the anti-trust lawsuit from the Federal Trade Commission in February, which scuttled Edgewell Personal Care Co.’s acquisition. All said, the company still is finding success with its e-commerce business, in-store sales in Target and Walmart, and its women’s razor line, Flamingo. The diversified product lines and sales strategies, Raider said, helped keep the company going through unpredictable times.

Here are two other tips from Raider on stepping up as a leader in 2020.

Telling your team it’s OK to take a day off to avoid burnout is one thing, but it’s another to require it. Raider said that the company introduced required mental health days this year, including a week off in August and days off around the presidential election. They then monitored online activity to make sure employees were truly staying offline.

“Giving people time and space to process has been really helpful,” he said. “Happy employees are more productive, more inspirational, and more innovative employees.”

Raider said a key to creating happy employees is his own attitude in meetings, and that’s true for any leader. Giving the example of a leader who walks into a meeting frustrated from external problems and asks only critical questions of a team’s project that they spent an entire day working on, negative attitudes will only demotivate an otherwise productive team. 

“I write myself notes,” Raider said. “Like, ‘This a time for you to be positive and inspire creative thinking.’ There’s a great turn of phrase in improv: ‘Yes, and.’ As in, yes, and let me build on your idea this way.”