Gillian Waters
Quick Facts
- Role: Co-protagonist; buyer for Smith & Banks Pet Supply; single mother to Bo
- First appearance: Chapter 1 (meeting with Jackson Hill)
- Core goal: Win the “Corner Office” promotion to Senior VP of Distribution by landing Jackson Hill’s “Angels Clothed in Fur” as an exclusive account
- Mentor: The Coach (George Henshaw)
- Outcome: Resigns from Smith & Banks to become managing partner of Angels Clothed in Fur
- Defining image: “Ms. Gray Flannel Suit”—impeccably dressed, poised, and guarded
Who She Is
At her core, Gillian Waters is a high-achieving, tightly controlled professional whose polished exterior covers the strain of doing everything alone—closing deals by day and raising her daughter by night. She begins as a classic “go-getter,” treating negotiations as contests to be won and people as pieces on a board. What makes her compelling is not her initial sharpness but the way she learns to relax her grip: to see people, not targets; to choose partnership over pressure; and to define success by value created rather than territory claimed.
Personality & Traits
Gillian’s strengths—discipline, intelligence, and grit—initially skew toward manipulation under pressure. The story peels that back to reveal her capacity for empathy and authentic leadership.
- Ambitious and mission-driven: Her promotion is not vanity; it’s a means to “put Bo in that school she wanted… And buy her a horse. And give her the world” (Chapter 2). Her ambition has a human center.
- Image-conscious, poised, and protected: Introduced as “Ms. Gray Flannel Suit,” she’s “decked out in an immaculate suit, silk floral scarf, crisp cuffs, and classy pumps” (Chapter 6). The meticulous look is armor—authority that hides economic strain and emotional fatigue.
- Initially manipulative: She arrives at her first meeting late, mispronounces Jackson’s name, and holds her cards tight—textbook tactics that align with Genuine Influence vs. Manipulation. These moves win initiative but cost trust.
- Tough-minded and prepared: “She was smart, and she worked hard,” and she does her homework on Jackson’s company (Chapter 2). Even her manipulations rest on thorough research and sharp observation.
- Skeptical yet teachable: She doubts the Coach and his “Winning Strategy,” but curiosity and an honest hunger to do better keep her listening. Her openness, once engaged, becomes the lever of her transformation.
- Protective mother: Bo is her why—and her barometer for choices that create safety rather than scarcity. The story of Bo and Cleo reframes “influence” as the creation of trust, not control.
Character Journey
Gillian begins by treating the Jackson Hill deal as a zero-sum contest that will make or break her career. Her early tactics—deliberate lateness, misnaming, leveraging power—earn her momentum but erode relationship. When the Coach introduces the “Five Secrets of Genuine Influence,” he doesn’t just offer techniques; he exposes the emotional price of manipulation and points her toward a different scoreboard: value, trust, and long-term alignment. Meeting Elizabeth Bushnell (“Mrs. B.”) gives her a living model of abundance and gratitude rooted in The Go-Giver Philosophy of Value Creation. The real test arrives in the final negotiation. With leverage to force a deal, she instead steps into Empathy and Perspective-Taking, searching for a “third option” that honors both sides. Choosing partnership over pressure—Collaboration over Competition—she turns down the promotion she once craved and builds something better: a business and life aligned with the values she has learned to trust.
Key Relationships
- Jackson Hill: Initially “the account” she must capture, Jackson is treated like an obstacle, not a person. As Gillian shifts from tactics to trust, she begins to honor his standards and mission. Their relationship evolves from brink-of-walkaway standoffs to a partnership grounded in mutual respect and shared purpose.
- The Coach (George Henshaw): He is less a strategy dispenser than a mirror, revealing how her methods sabotage her goals. By reframing influence as service, he helps her swap control for connection—and shows her that courage often means letting go of leverage.
- Bo (daughter): Bo’s needs give Gillian urgency; Bo’s story with her cat, Cleo, gives Gillian understanding. The Coach uses it to illustrate that true influence creates safety. Gillian’s career choices ultimately align with the home she wants to build for Bo.
- Elizabeth Bushnell (Mrs. B. / Aunt Elle): Mrs. B. embodies grace in action—feeding children, leading with gratitude, and redefining wealth. Observing her shifts Gillian’s metric of success from corner offices to contribution.
Symbolism & Significance
“Ms. Gray Flannel Suit” isn’t just a look—it’s a worldview: crisp, controlled, and transactional. As Gillian sheds that armor, she doesn’t become softer so much as stronger, redirecting her drive toward value creation and genuine connection. Her arc personifies the book’s thesis: real success flows from what you contribute, not what you can coerce.
Defining Moments
Gillian’s turning points are negotiations—with others, and with herself.
- First meeting with Jackson (Chapter 1): She arrives late and mispronounces his name to unsettle him.
- Why it matters: It signals her reliance on control tactics and sets the mistrust that later must be repaired.
- Meeting the Coach (Chapter 5): She encounters the “Five Secrets of Genuine Influence” and hears a critique of manipulation.
- Why it matters: Plants the idea that her approach is self-defeating—winning moments while losing relationships.
- The “Collision” (Chapter 10): A disastrous second meeting where both sides posture and nobody connects.
- Why it matters: Clear, painful proof that tactics exhaust value; it propels her toward a different playbook.
- Visiting Elizabeth Bushnell (Chapter 11): She witnesses philanthropy grounded in gratitude.
- Why it matters: Offers a felt experience of abundance-thinking and redefines what a “win” looks like.
- The final negotiation (Chapter 13): With leverage to force the deal, she opts for a “third option,” resigning to join Jackson as managing partner.
- Why it matters: The culmination of her transformation—choosing alignment and partnership over a hollow victory.
Essential Quotes
She didn’t just want Jackson’s line. She needed it. Not only would it be a great account to win. It was an account that could make her career.
— Chapter 2
This frames Gillian’s urgency: the deal is a life-changer, not a trophy. It explains her early overreliance on control—and the stakes that make her later relinquishment of leverage so meaningful.
“Manipulation might sometimes win the game, but it never wins the game.”
— The Coach, Chapter 5
The paradox names Gillian’s core problem: short-term victories that produce long-term losses. It reframes “winning” as sustainable influence built on trust, not tactics.
Way to go, Jill. You certainly slammed that back door, didn’t you.
— Chapter 10
Her self-reproach after the “Collision” exposes her awareness that she shut down connection. This is the hinge from defensive competence to reflective growth.
“I’m just thinking,” she said. “Maybe there’s a third option.”
— Chapter 13
The moment she moves from either/or to both/and. It captures the mindset shift from force to creativity, from scarcity to possibility.
As of today, she was managing partner of Angels Clothed in Fur, LLC.
— Chapter 13
A simple sentence with sweeping implications: she rejects the old scorecard and builds a future aligned with value, trust, and shared mission.
