Skip Dillard didn’t choose radio. Radio chose him. From the time he was a kid he said he was “was addicted to radio,” comparing the pull to alcohol or drugs.

One Lesson, Every Market

Dillard has programmed in Detroit, Buffalo, New Orleans, San Francisco, Washington D.C., and for the better part of his career New York City. Today he is Program Director for 94.7 The Block in NYC and holds a national role overseeing the Rhythmic and Throwback formats at Audacy. When asked what traveled with him across every city and station he’s programmed, the answer comes fast.

“Radio is at its very, very best when it touches people,” Dillard says. He calls community “the most important aspect” of the job. “Figure out what listeners need and try to give that to them day in and day out,” he says. “That’s been the secret to my success.”

Two Brands, Two Battles

Dillard spent over a decade protecting WBLS, a legacy New York institution. Then he built WXBK, 94.7 The Block, from the ground up. I asked about the difference between protecting a heritage brand and building a totally new one. “Both have their unique challenges,” he says.

WBLS meant guiding a storied brand through the shift from diary ratings to electronic measurement. “There were a lot of problems going to the PPM methodology,” he says, and some of the station’s biggest talents struggled at first. The Block presented a different fight entirely: “getting your niche in a market full of heritage radio.”

His team built The Block’s throwback Hip Hop sound on research. “We looked at the [older] playlists from those [heritage] stations, and then did music tests based around when those records broke in New York,” he says. Stations and DJs often pushed “the B side of what was actually being worked” as a single and then those records ended up becoming the bigger hit in the city.

But the real differentiator wasn’t the music. “A partnership with the community you serve, whether it’s New York or Des Moines, Iowa, is crucial, and that was part of the plan here,” he says.

Get Up From Your Desk

“Look at your zip codes, where your listeners are coming in from,” Dillard says, advising young programmers where to start if they’re new to a market.

Reach out to local organizations, he says, because “they’re always looking for an opportunity to have a mouthpiece for things they’re doing.”

But most importantly, “get out from your desk. Read all the data and research you have access to, and then get up and go outside,” he says. “I learned more at a festival, or weekend gathering, or networking event about what’s going on in my community than I will ever find out from any kind of research data.”

Walking the Political Tightrope

Urban radio brands handle politics differently, and Dillard thinks that’s exactly right. Some stations, like Audacy’s in Atlanta, lean in. “People have come to respect that from V103 in Atlanta,” he says. “They just expect to be informed about what’s going on.”

Other markets call for restraint. “Politics has never been more polarizing,” Dillard says. “Listeners are beat down with it every single day on their phones, on television.” His guiding question: “Is it better that I inform rather than become another source of polarization?”

He’s also realistic about lanes when it comes to strategy for The Block. Nobody beats The Breakfast Club at its own game. “That would be crazy if you had a morning show and someone say, hey, I’m gonna be as political as they are,” he says. “It’s where they put their tent pole.” His advice for everyone else: give listeners the facts and trust them to decide. “I think people are a heck of a lot smarter than we often give them credit for, and we have to realize that,” he says.

Bridging the Generational Gap

The Block trades heavily in nostalgia which would lead one to believe that the audience would only be older. Instead, younger listeners have been showing up, and Dillard sees that audience growing. “What’s nostalgic to us is very fresh and new to them,” he says.

He credits sampling for the bridge. Modern pop and rap lean hard on those same originals, sending younger ears back to the source. “People are looking back to the 90s, the early 2000s, and finding and reacquainting themselves,” he says.

A recent college consulting project reshaped how Dillard sees that generation. The students he spoke with about what’s important to them never once mentioned money. “They wanted to be relevant, and they wanted to make a difference,” he says. “They don’t want to be a cog in a wheel.” That conversation left him hopeful. “These young people, if you really listen to them, they can give us hope, they can give us strength, because they’re moving beyond the divisions, they’re moving beyond race.”

Juneteenth, Black Music Month, and America 250, All at Once

This year’s calendar stacks Juneteenth, Black Music Month, and the lead-up to America’s 250th anniversary into the same narrow window. Dillard doesn’t see a scheduling headache. He sees an opening. “Black people played a crucial part in the development and success of this country, and continue to do so,” he says.

He’s blunt about the alternative. “We have an unfortunate situation where, in some aspects of our present day politics and society, we want to marginalize the contributions of Black people, and other ethnic and religious groups,” he says.

Dillard’s own family history sits underneath that belief. He’s stood inside a house in Danville, Virginia, on land his grandmother’s people once worked, a property descendants of the enslaving family still own today. “It left me with an emotional understanding of where we’ve been, a very bloody and hard and painful past,” he says. “There were a few tears I shed, but when it was all said and done, it filled me with a sense of purpose. It filled me with a sense of belief.” His conclusion: “If we could get through slavery, the civil rights movement, world wars, 9/11, we can get through anything. We just have to work together, not fear each other.”

A Different Kind of Patriotism

Dillard isn’t asking stations to paper over the complicated relationship some Black listeners have with patriotic messaging. His suggestion for Urban stations programming around America 250 is more specific. “Celebrate your local Black heroes,” he says, pointing to Benjamin Banneker in D.C. and Senator Raphael Warnock in Atlanta as examples worth airtime.

“There are so many local leaders, past and present, that helped and continue to build this country and change America for the better,” he says. “Let’s salute them and make sure that for America 250, everybody’s in the mix.”

Looking Ahead to the Barrett Media Audio Summit

Dillard heads to the Barrett Media Audio Summit on July 2nd for a Hip Hop panel alongside Funk Flex, Angela Yee, Devin Steel, and Damizza. He’s genuinely excited, partly because music finally has a real seat at a summit, but also because a lot of surviving conferences today are solely sales focused. “It’s really nice to be around content people for our business,” he says.

That makes a room full of talent and programmers, swapping real challenges, feel rare. “What I most look forward to is shaking the hands of many of my colleagues,” he says, “and discussing the real life challenges we face every day in our radio stations, working to make them better, working to make them more relevant and connected with our listeners.”

“It’s going to be a lot of fun,” Dillard says. For a programmer who’s spent three decades chasing what makes radio actually touch people, that’s about as good a note as any to end on.

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