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40 Under 40 - Class of 2019
Business Observer Thursday, Oct. 17, 2019 7 months ago

Shane Costello, 36

Shareholder, Hill Ward Henderson
by: Brian Hartz Tampa Bay Editor

Lawyers, along with doctors, are often stereotyped as having big egos. Not so for Shane Costello, a shareholder at Hill Ward Henderson, a Tampa-based law firm whose practice focuses on litigation related to real estate and land-use issues, complex commercial matters, and trust and estate disputes.

Costello says the type of business law he practices is nuanced and doesn’t always result in all-out victories. So he strives to keep the needs of his client at the forefront at all times while letting his desire to win take a backseat.

“It’s not like from day one you say, ‘OK, let’s litigate and burn everything to ground,’” he says. Instead, “let’s figure out what the best plan is for you, given your business and your goals with the respect to the litigation.”

The key is to develop a clear but realistic picture of what a positive result would look like, Costello says. “If we could win on two issues but lose on the other three, we’ll take that all day long — that kind of thing.”

That approach also helps Costello keep courtroom wins and losses in perspective. “It goes back to the idea of putting yourself in your client’s shoes,” he says. “I think, ‘OK, well, if I owned a business, and this happened to me, what would I want my lawyer to do?’ I’d want my lawyer to tell me straight, tell me like it is and advise me on what to do.”

Costello describes his courtroom style as “even-keeled.” He adds, “I’m not into histrionics and that kind of thing.” However, he says it helps to be a “chameleon” who can read the room and adapt the style and delivery of his presentation accordingly.

“If you're in front of a judge, it can depend on what you know about your judge and what he or she might like or dislike, as well as what your opposing counsel is like, how they act and also the facts of your case,” he says. “Like, do you need to show more indignation about what happened, or are you going to be more effective by just taking a matter of fact approach?”


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