Leadership Lens: Peggy Williams-Smith on selling Milwaukee and leading as an optimist

Apple Podcasts


VISIT Milwaukee president and CEO Peggy Williams-Smith joined Marquette University president Michael Lovell and BizTimes managing editor Arthur Thomas on Leadership Lens, a monthly podcast that dives into the leadership styles of Milwaukee-area business leaders.

Peggy Williams-Smith
Peggy Williams-Smith

The conversation, recorded in mid-April, touches on how Williams-Smith navigated the COVID-19 pandemic, which hit just after she started in her role, landing the Republican National Convention, selling Milwaukee and addressing its challenges, leading as an optimist who doesn’t want to say ‘no’ to things, and much more.

See excerpts from the conversation below and listen to the full episode in the podcast player above:

On her background in the hospitality industry:

“I started as a bartender and a waitress and I think anyone who starts out in those capacities has the heart of hospitality, if you love doing it. That’s why I ended up in this career, I love making people happy. It is an amazing thing to be able to see someone smile,” Williams-Smith said.

“It is something that has shaped who I am as a leader,” she added. “I don’t say ‘no.’ Sometimes you have to find a way to get to ‘yes,’ but it is what we base our organization, how do we make sure that we are connecting people in the community.”

Selling Milwaukee while addressing its challenges

Williams-Smith pointed out that VISIT Milwaukee’s work of bringing visitors to the city means talking with people from the suburbs, around the state or around the world.

“When I’m talking to a meeting planner from all over the world, the subject of crime comes up very rarely and I have to keep that perspective when I’m talking,” she said.

While someone from a trade association in Washington D.C. may not be familiar with day-to-day issues in Milwaukee, a potential visitor from elsewhere in the state may be acutely aware because of coverage on television. Williams-Smith said the reality is every major city has its challenges and it’s important for her to communicate with honesty and authenticity.

“We tend to focus on the negative and as I said, being a glass half-full person … there are things I have seen the leadership in our city do, both public and private come together in ways they never have before to figure out how to solve some of these things,” Williams-Smith said.

When the city began having issues with large gatherings and some violence, Williams-Smith said it wasn’t an issue she would talk a lot about publicly, but she made a point to be involved in discussions with other city leaders to find solutions.

“It’s behind the scenes work that allows me to go out and talk about the positive things, because I know that work is being done to help make those changes,” she said.

Making decisions

Williams-Smith also discussed the kinds of decisions that make it to her desk and the ones that don’t.

“I have an incredibly inventive group of people who want to try new things, so when it comes to expensive things, they have to cross my desk,” she said.

At the same time, VISIT Milwaukee has a robust and active presence across social media. Williams-Smith said she was asked recently how she goes about approving all the various posts.

“I don’t,” she said. “I trust my team to speak in the voice of Milwaukee on behalf of Milwaukee and they do a really good job. If I was looking at every single one, it would not be the same social media presence. I am not who we are trying to attract. I do try to empower the team to be able to make the decisions they need to make.”

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Arthur covers banking and finance and the economy at BizTimes while also leading special projects as an associate editor. He also spent five years covering manufacturing at BizTimes. He previously was managing editor at The Waukesha Freeman. He is a graduate of Carroll University and did graduate coursework at Marquette. A native of southeastern Wisconsin, he is also a nationally certified gymnastics judge and enjoys golf on the weekends.