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Arts / Leadership / Workplace culture

‘The show must go on’: 5 lessons on leading like a creative

These executives are also an actor, an opera singer and a musician. Here's how they bring an artist's mentality into business.

Matt Silva, Jonathan Whitney, KerriAnn Otaño and Renarde Hill discuss the "Power of the Arts" at MILLSUMMIT 2023. (Photo by Holly Quinn)
What do the opera, a jazz festival and a Shakespearean play have in common? In Delaware, they’re all run by creatives who could teach even the most corporate-minded business executives a few things about leadership.

That’s because arts organizations’ execs are business people, too: Instead of software or finances, their products and services are music, theater and art.

Yet arts leadership often comes from a different place. These execs are likely to have followed a creative path before becoming the boss, including years on stage. And sometimes, as with Jonathan Whitney, they actively work as an artist. Whitney is the 2020 recipient of the Delaware Division of the Arts Established Artist Fellowship for Jazz Composition, as well as owner of Flux Creative Consulting.

“Jazz is about an individual’s voice coming together with other individuals’ voices,” Whitney said as a panelist on MILLSUMMIT’s “The Power of the Arts — How it Made Me a Great Leader” panel on Aug. 9. “As the band leader, I consciously step back, and before I give instruction on a song, say, ‘Let’s see how it sounds today.’ And we run it down, and what that person brings without me trying to dictate what they do can be the freshest, dopest thing that we could have come up with.”

You may be prepared with numbers and metrics, but that pause — allowing other members of your team to first offer their ideas — can lead to great things, whether you’re leading a band or a boardroom.

The show must go on

One of show business’ most tried-and-true sayings, “The show must go on,” speaks to the unpredictability of live arts and entertainment. It’s something Kerriann Otaño, VP of engagement for OperaDelaware, brought to her leadership position after years as a professional opera singer.

“There’s never a moment when you’re performing that you’re not entirely present so that you can interact with the other performers,” Otaño said. “You have to be wholly present, and you have to be ready to improv if anything goes wrong. I find that that’s been a huge asset in managing when things things take a turn. There’s always a way to improv your way out of it.”

Listen empathetically

Matt Silva, executive and artistic director for the Delaware Theatre Company, often uses lessons learned from his time as a young stage actor now that he’s an executive.

“In the arts, something that I’ve really learned that’s helped me be the leader of teams is to be an empathetic listener,” Silva said. That includes “hearing and considering before responding, because when conflict arises, the first thing you want to do is settle everyone. They need to know that the heartbeat can slow down a little bit and we can keep ourselves rational. And we can actually genuinely listen and respond to one another, because oftentimes conflict is resolved when you’re really, actually letting things sink in.”

Collaborate to revolutionize

In the arts, it’s not uncommon for the material to be something that has been done many times over many years, whether it’s an opera, play or classical piece of music. How do leaders take something that’s been done before and make it into a successful product?

“I would say that collaboration is the most important thing about the arts — it leads to art that is transformative and not art that is just a repetition of something that’s already been created,” Otaño said. “We see this a lot in opera, that we could just recreate something that was successful 100 years ago. The only way for us to revolutionize it and to take it to the next level is to collaborate. And the only way to collaborate is to give not just a shared power, but a shared ownership.”

Be authentic

In the arts, people are often expected to bring their authentic selves, even if they’ll be playing a part on stage. Authenticity and transparency matters for leaders as much as anyone else, Whitney said.

“I think if we expect our teams to bring their whole selves, we have to bring our whole selves,” he said. “It could be even, when I talk about authenticity, coming into the meeting and saying, ‘Let’s take five because I’ve had five back-to-back meetings and I know my mind can’t focus on you right now in the way it needs to.’ That’s authenticity and it’s OK. That is not weakness.”

Bring your ‘moment before’

Similarly, before an actor enters the stage, they have to know their character’s “moment before” — what was happening in the character’s life the moment before the acting starts, where they were physically and mentally.

Translated into the workplace, the “moment before” is a team member’s life and the aspects of it that they may turn off when in work mode.

“I always encourage my teams to bring their ‘moment before,’” Silva said. “That’s what I think about in terms of authenticity, it’s not about weakness. It’s about bringing that weakness that might exist into the room and finding strength together in it.”


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