Most business podcasts follow a script.

A host asks a question.
A guest gives a polished answer.
Everyone sounds smart.
Nobody says anything new.

This is not that conversation.

In this episode of Possibilities with Monique de Maio, we introduce a new format:

Business Q&A: In the Room

Two leaders.
Real decisions.
No theory.

Monique sits down with Stephanie Baker, former Chief Commercial Officer, COO, and CMO, for something different:

A real-time business debrief between two operators with 50+ years of combined experience.

No scripts.
No polished talking points.

Just two people who have been in a lot of rooms…

processing out loud what they’ve actually seen, what they’ve gotten wrong, and what they now recognize immediately when they walk into a company that’s in trouble.

In this episode, we explore:

→ Why “we need more sales” is almost never the real problem
→ How to spot a broken org chart in the first 30 days
→ When a rebrand request is actually a symptom
→ What changes first when leadership teams stop being honest
→ Why fighting your way to the top is the wrong strategy
→ The role of value alignment in building teams that actually work

If you’ve ever sat in a room where everyone agreed in the meeting and nothing changed afterward…

If you’ve ever been handed an org chart that looked fine but felt completely broken…

Or if you’re navigating growth that isn’t landing the way it should…

This conversation will feel familiar.

TIMESTAMPS

00:00 Introduction: A Different Kind of Business Conversation

01:53 What 50+ Years of Experience Teaches You to Spot in 30 Days

07:22 The “We Need More Sales” Problem: Why It’s Usually Not the Real Issue

11:43 When the Org Chart Looks Fine on Paper

14:14 The Role of the Consultant vs. the Insider

19:03 When a Rebrand Request Is Actually a Symptom

25:59 Brand Promises You Haven’t Earned the Right to Make

29:51 What Changes First When Honesty Leaves the Room

33:37 Value Alignment: The Non-Negotiable Foundation

36:58 What People Don’t Know About Stephanie (Bikram Yoga for 20 Years)

38:21 What She Now Questions About Leadership

40:26 On Helping Each Other: Why Women Can’t Do It Alone

45:51 Worst and Best Career Advice (The Job in Amsterdam)

50:51 Closing: If This Sounds Like Your Company, You Know Where to Find Us

ABOUT OUR GUEST

Stephanie Baker is a senior executive with more than 20 years of experience leading commercial strategy, operational transformation, and growth across travel, entertainment, and consumer sectors.

Most recently, Stephanie served as Chief Commercial Officer at EBG, one of the largest privately held travel and entertainment companies in the U.S., where she led product strategy, corporate sales, business development, marketing, digital customer experience, and partner development. During her 14 years at EBG, she also held the roles of Chief Operating Officer and Chief Marketing Officer.

Earlier in her career, Stephanie held senior leadership roles at Madison Square Garden Entertainment and Feld Entertainment, where she drove marketing strategy, production growth, and international expansion across Europe.

She currently serves on the Iron Eagle Advisory Board, is a board member of Thrive Women in Travel, and is a member of Chief.

This podcast is part of our mission to amplify women who are redefining work, life, and leadership.