Season Two, Episode 9: Leading Through Change: Doug Howe on Curiosity, Culture, and the Future of Retail

Doug Howe didn’t set out to build a career in retail. But more than three decades later, he’s leading one of the industry’s most recognizable companies through an era of constant disruption. 

As CEO of Designer Brands, parent company of DSW Designer Shoe Warehouse, Doug has learned that successful leadership isn’t about having all the answers. It’s about staying curious, protecting a company’s culture, and helping people move forward together through change.

What began as an unexpected career path has become a lifelong lesson in adaptation, stewardship, and never standing still.

The Tailspin

As a business major interviewing during his senior year of college, Doug wasn’t looking for a lifelong profession. A visit to the renowned management training program at May Department Stores, however, changed everything.

“They shared the amount of responsibility they had, the autonomy they had, that no two days are the same, changing priorities all the time, always looking forward,” he recalls. “And I just went from being mildly interested to being like, ‘Wow, this job is created for me. I love it.’”

That decision launched a career spanning department stores, television retail, product development, design, big-box retail, and ultimately the CEO role at Designer Brands, the now parent company of DSW.

Along the way, Doug discovered that the greatest lessons didn’t come from formal training alone.

“You learn by observing, through osmosis,” he says. “I always say I formed my leadership style as much from people you don’t want to emulate as those you do.”

His career wasn’t built by following a straight path. It was built by embracing new experiences, learning from different industries, and becoming comfortable with constant change.

The Work

When Doug stepped into leadership at Designer Brands, the timing couldn’t have been more challenging.

The company was emerging from COVID, consumer behavior was shifting rapidly, and the retail industry was entering yet another period of disruption.

“There has been no ‘normal’ since COVID,” he reflects. “The only thing that’s been constant has changed.”

Rather than searching for stability, Doug learned to just expect uncertainty.

“What it has taught me is, never rest in your laurels. Always be looking around the corner for what’s coming and just being very, very curious with regards to the need to continue to adapt and focus on what’s ahead.”

That philosophy has shaped both strategy and culture, arguing that curiosity is the defining characteristic of effective leadership.

“People ask, ‘what do you think is the most important skill of a leader or most important attribute of a leader?’ I think it’s to be curious,” he says, “always watching what’s happening in the world, where the customer’s moving.”

For Doug, that curiosity means spending time where the work actually happens. 

“Ninety-nine percent of the time I don’t announce when I’m going to go into a store, because I don’t want it to be a presentation. I just want to experience the store as a customer.”

It also means surrounding yourself with people who know more than you do.

“I’m a big believer in this theory of T leadership,” he explains. “You have to fly at that level of altitude where you know what questions to ask, but then you need to know when to go deep on that vertical as well.” 

For Doug, great leaders don’t need all the answers. They just need to know the right questions to ask while empowering experts around them to succeed.

“Getting more comfortable being a little less comfortable in the details,” he admits, “is a tough challenge. You want to know everything about every single topic and that’s just not humanly possible.”

As Designer Brands continued evolving, Doug remained focused on one idea above all else: alignment.

“Once you start to see the momentum, celebrate the wins with the team. Get everyone rallying around that single idea,” he offers. “When you have everyone aligned and focused on your priorities, it’s an incredible tailwind.”

The Tailwind

Doug’s perspective on leadership isn’t centered on transformation for its own sake. Instead, it’s rooted in stewardship.

“I have made different decisions based on what’s happening in the world, where we’re focusing, versus my predecessor,” he says. “We’re going to evolve the business and we’re going to make changes, but you want to be respectful of the fact that there is a culture, there are values.”

“But as a CEO or as a leader, while you’re a steward of the company’s values, you don’t get to change those values.”

Doug believes every leader inherits something worth protecting.

“There’s DNA and there’s positioning, a culture and there’s values that you need to respect. Those are the differentiators of the company and you want to maintain those.”

That same philosophy shapes how he develops future leaders.

“For the first 90 days, just listen.” 

Learning comes before changing. Listening comes before leading.

And when difficult conversations happen within the executive team, Doug believes unity matters once decisions are made.

“Divided together, but united apart,” he describes it. “Let’s agree we’re going to disagree and have those candid conversations as a leadership group. But then when we leave the room, what’s the united message that we’re going to be sharing with the rest of the team?” 

Looking ahead, Doug doesn’t hope to be remembered simply for financial performance or business growth.

“I think just to be remembered as somebody that operates with high ethics and high integrity and also having fun along the way.”

For a leader whose career has been defined by constant evolution, that may be the greatest lesson of all: adapt relentlessly, lead with curiosity, protect what matters, and never lose sight of the people who make the work worthwhile.

To hear more from Doug Howe about retail leadership, navigating disruption, building resilient teams, and leading with curiosity, watch or listen to the full episode of re:Purpose with Buddy Teaster.