Career Coaching​

The Bailey Difference

Ellen Bailey leads Executive and High-Potential Development for McKesson, a Global 10 company. In this role, she drives innovative learning strategies that elevate leadership performance across the enterprise.

Previously, Ellen spearheaded the development and execution of Harvard Business Publishing’s first enterprise-wide strategy for inclusion and belonging—aligning organizational culture with customer engagement and business outcomes.

She is also the founder of The Bailey Difference™, a platform committed to providing career coaching that equips leaders with the tools and confidence to drive their own career success and advancement.

Objectives

One-on-One Coaching is tailored to meet the unique needs of each individual, with a focus on enhancing advancing career development, leadership skills, improving communication, and/or strengthening executive presence. We will use my methodology and templates to guide you through your journey that drives both short- and long-term impact. We do this through a series of hourly coaching sessions that can be conducted virtually.

Engagement Model

  • Introductory session to discuss the area of focus and ensure there is a workstyle match. (complimentary)
  • Package: NASP rate of $95 per session (standard rate is $150 per hour)
  • Minimum of 3 live sixty-minute zoom calls (monthly or bi-weekly)
  • Brief self-assessment
  • Homework
  • Resources (thought leadership, tools, etc.)
  • Package enhancements
  • 30-minute impromptu calls can be added at a rate of $30 each
  • Additional 5% package discount if a minimum of 4 sessions is purchased to be charged monthly
  • Introductory session to discuss the area of focus and ensure there is a workstyle match. (complimentary)
  • Package: NASP rate of $95 per session (standard rate is $150 per hour)
    • Brief self-assessment
    • Homework
    • Resources (thought leadership, tools, etc.)
  • Package enhancements
    • 30-minute impromptu calls can be added at a rate of $30 each

Cheryl Mills Coaching

Cheryl Mills is an ICF-PCC certified executive and leadership coach with 25 years of senior experience in financial services, including roles at BNY Mellon, Pershing, Broadridge, and Chase. She coaches mid-career and senior leaders to strengthen their leadership presence, navigate complex workplace dynamics with confidence, and make intentional career moves. Cheryl’s style is warm, direct, and grounded in deep listening and insight.

What You Can Expect

As the founder of Cheryl Mills Coaching, Cheryl helps leaders get clear on what they want, build the skills to get there, and show up with greater impact. Her coaching is practical, motivating, and focused on real results — from improving communication to preparing for the next step in a career or leadership journey. Clients walk away with clarity, confidence, and tools they can apply immediately.

Client Experiences

“Cheryl helped me go from feeling stuck and discouraged to landing the job I had been working toward for years.”
Shadava, Finance & Compliance Manager

“Cheryl helped me become far more intentional in how I lead, and the shift strengthened my executive presence.”
L. Jobson, VP of Product, Extend

Engagement Model

  • Introductory Session:

  • Complimentary chemistry call to establish goals and ensure coaching fit.
  • Structure
  • Sixty-minute virtual sessions (monthly or bi-weekly)

  • Light homework or reflection

  • Practical tools and resources

  • Optional brief check-ins as needed