Lawyer by Day, Comic by Night: What Stand-Up Taught Hyatt's Stephanie Weiss About Work

Hyatt lawyer Stephanie Weiss took a stand-up class on a whim two years ago. Now she's on stage most weeks, and the lessons are showing up in her day job (no punchline required).

Lawyers have a reputation for being a little stiff. Stephanie Weiss is doing her bit to fix that.

By day, she's Senior Counsel at Hyatt Corporation in London, handling the legal side of marketing: sponsorships, promotions, agency deals, and making sure that when an influencer raves about a hotel, you know they're being paid to do it. (Yes, that #ad is her territory.) By night, she's on a stage somewhere in London with five minutes and a microphone, talking about getting older, receding gumlines, and the less glamorous realities of being a woman.

It started with a gift card. Friends gave her a voucher for classes she could spend however she liked, and stand-up caught her eye. "I was like, oh, why not?" She signed up for a course at City Academy in London, a few classmates wanted to keep going, and she went with them. Two years on, she's one of only two from that class still performing.

Ask whether she was always funny and she jokes that she still isn't. Was she the class clown? "Definitely not. But I have always been a pretty good storyteller." She did some school plays as a kid, but never aspired to be a comedian.

Here's what an open-mic habit has taught her about work, and some tips you can steal. And who knows, maybe it will inspire you to try comedy, too.

1. After a comedy club, the conference room is an easy crowd

The obvious win is public speaking. Once you've told a room of strangers about your most personal material, presenting a PowerPoint to colleagues feels like a breeze. "I'm way less nervous," she says, "because you sort of get comfortable with the fact that it's pretty unlikely you're going to say something crazy."

And the good news for the rest of us? The corporate bar for funny is low. "Nobody is expecting to laugh," she says. For a conference icebreaker, she offered a prize of two free nights at the hotel, with one catch: you had to use them by tomorrow. Silly, she admits. It worked.

Stephanie’s still working on projection ("I'm pretty quiet"), but she's far more conscious of her voice than she used to be.

Try this: Test one new minute. Comics only try out about a minute of new material per set and keep the rest proven. Do the same with presentations: one new idea, story or joke each time, built on what you know works.

2. Clarity beats clever

When you're performing for strangers, nobody knows who you are or where you're coming from. "So you have to just be exceptionally clear," she says. When a comic bombs, more often than not the audience just didn't follow. "It's not because they're not funny or because the concept isn't funny. It's because we didn't totally get what they were saying."

Stephanie has always been concise, but stand-up sharpened something different. "If I'm telling you something, I'm clear on why I'm telling you, and I'm making sure you have all the relevant information that you need to make it make sense to you."

That, it turns out, is what makes her more convincing in negotiations and with clients. People are more likely to take your advice when they understand where you're coming from.

Try this: Before your next pitch or presentation, answer two questions: why am I telling them this, and what do they need to know to follow along? Then do what she does: record yourself on a voice note, play it back, and listen for the spot where a stranger would get lost.

3. Read the room, then change tack

Stephanie once did a gig to a crowd who could not have cared less about her bit on dry cleaning. "I was like halfway through, and I just stopped," she says. She switched to other material, and the second half went much better.

The same instinct works in a meeting. If the threat of a big lawsuit isn't enough to get a client to change an ad, she'll try a different angle, like whether it will actually land with consumers. "You have some arsenal in your back pocket," she says, so you're less stuck if your first approach falls flat.

Try this: Steal her rule for punchlines: if it doesn't land after a couple of tries, cut it. The same goes for a presentations and pitches. Always have a backup idea.

4. Flip the frame

One classic joke structure takes a common feeling and turns it upside down, and she's started using it at work. "Oh my God, how annoying that I have 17 competing deadlines," becomes, "Isn't it a treat to have 17 competing deadlines?"

It's unexpected, and it takes the sting out.

Try this: Next time you're spiraling, say the stressful thing out loud as if it's a gift. Sarcasm can be surprisingly good for perspective.

5. Only say what you believe in

She took a few joke-writing courses and found the formulas counterproductive. Squeezing something funny into a rigid structure, she says, "sort of loses it for me." Worse, a formula can lead you to a joke that's technically right but that even you don't find funny. When the audience agrees, "you're like, why did I put us both through this?"

When she tells a joke she truly believes in and it falls flat, it stings far less. "If you believe in what you're saying, it matters less what other people think."

Try this: If a point doesn't convince you, cut it from the deck. If it does, keep it, even if it might not land.

6. Care less, share more

Stand-up is, in her words, "all dudes." And she's noticed plenty of men on the circuit who get on stage with very little practice and no visible nerves. Her reaction: wow. Okay.

Stephanie also thinks her mom has gotten much funnier over the last decade, because she no longer worries about what anyone thinks. "There's so many funny women, and usually they're a bit older because until a certain age, we just care so much," she says. "I think it's helped me shed that a bit earlier, which I'm grateful for."

Caring less is what lets her get vulnerable on stage, and her material is about as personal as it gets. That openness, it turns out, is how you connect with a room. "I think we all have tough feelings and tough moments, and finding a way to laugh at them is something that everybody wants to do," she says. "So it's a pretty good way to gain camaraderie." The less buttoned-up you are, the easier you are to relate to, on stage or in a meeting.

Try this: Next time you're over-preparing or second-guessing, picture the guy who'd get up there with very little practice. Just borrow a little of his nerve. And share the messy bits. A story about something that went wrong, told with a laugh, builds more trust than a polished one.

7. Do something just because you love it

Here's the simplest lesson of all: she loves it. Stand-up makes her happy, and that happiness doesn't stay behind at the open mic. It comes with her to the office, into meetings and onto client calls. A night on stage leaves her lighter, more relaxed and, frankly, a happier person to work with.

So would she recommend other women give it a go? "Totally."

Try this: Take the class. Stand-up, improv, whatever you've always quietly wanted to try. Her entire decision-making process was "oh, why not?" Borrow it, and book before you talk yourself out of it.

Emily Goldfischer and Stephanie Weiss in London

How she does stand-up

• The set: Five minutes, with a laugh roughly every 20 to 30 seconds.

• Rehearsal: Records herself practicing while doing the dishes.

• Getting stage time: Easier than you'd think in London. Beginner nights often require you to bring a friend, so "I called in a lot of favors at the beginning." These days she performs about once a week, mostly at a friend's show.

• Off-limits: Work. She has no jokes about her job.

• Comics she rates: Whitney Cummings, Taylor Tomlinson, and Gianmarco Soresi.