61. Selling Without the Mask: Authenticity, Improv, and the Inner Game of Sales

On this episode of Thoughts On Selling, I’m joined by the fabulous Stacy Bishop, and wow, we cover some ground. From Midwest values and fintech sales to improv comedy and why your brain should zip it sometimes—we’re bringing the laughs and the lessons.

If you’ve ever wondered whether you’re selling—or just waiting to talk—or struggled with how to pivot in a sales call without face-planting, this one’s for you.

Here’s a taste of what we dig into:

🎯 Authenticity over ego

• Stacy shares how growing up in the Midwest shaped her career in banking and fintech sales—and how being real beats trying to be someone else.

• I confess to the times I tried on other people’s “sales personas” like ill-fitting suits. (Spoiler: It didn’t work.)

• We talk about dropping the mask and just being you—even when you’re the only woman in the boardroom.

🎭 Improv wisdom for sellers

• Why every statement in a conversation is an offer, not an objection.

• The magic of “Yes, and…”

• How I learned from improv (and my dog) that being present changes everything in sales.

🧠 The inner game of selling

• Why you can’t think your way through a tennis swing—or a sales pivot.

• “Go slow to go fast”—what racing, parenting, and selling all have in common.

• Stacy and I bond over how little time salespeople actually get to practice their craft—and why it’s killing deals.

🚀 Practical tips you can steal right now:

• Ask your customers why they’ve stayed with their company for 25 years—you’ll open doors you never expected.

• When you hear “no,” remember—it’s an offer, not the end of the road. Pivot like a pro.

• Don’t assume how people will react. Give them the chance to surprise you.

• When the customer starts nodding and saying yes… STOP TALKING. Zip it!

Stacy leaves us with two killer reminders:

✅ Be your authentic self—even (especially) in sales.
✅ Follow up. And then follow up again. Because today’s “not now” might be tomorrow’s “hell yes.”

Find Stacy on LinkedIn here — she’s all about helping other sellers figure out how to navigate this wild world of sales without losing their sanity.

Key Takeaways:

• Sales is human-to-human. Authenticity wins every time.

• Improv teaches incredible sales lessons: be present, pivot fast, and say “yes, and.”

• Practice isn’t optional—it’s how you go from “good” to “unconsciously great.”

• Go slow to go fast. Seriously.

• Drop the mask. Be yourself. It’s way less exhausting.

Quotable Moments:

“Give me the opportunity to surprise you.” — Stacy Bishop

“Are you being of service… or serving your ego?” — Lee Levitt

“Every statement is an offer, not an objection.” — Lee Levitt

This episode is a blast. It’s full of laughs, real talk, and enough practical nuggets to fuel your next dozen sales calls.

Thanks for tuning in, friends—and as always, go out there and sell like yourself.