Ann Bailey

Founder & President at The Bailey Leadership Group, LLC

Member since November 2025

Leadership

Education: Colby College - Boston University
Alexandria, VA, USA

Biography

Ann is a speaker, coach, leadership advisor, and facilitator who helps people and teams realize their full potential by breaking through barriers, solving problems, and making a lasting impact personally and professionally. She brings 30+ years of leadership experience coupled with expertise in executive coaching and conflict management to help unlock the capabilities that drive success for individuals and teams. Ann has experience as an individual contributor, a leader of teams and as a consultant in the human experience and in high performing teams. She held positions at Press Ganey, Vizient (formerly VHA), McChrystal Group and the National Health Service in England. She's experienced the good, the bad, and the ugly of the professional world and knows what it’s like to be a part of and to lead a great team, and what it’s like to feel like you’re not in the right place professionally. Like many women, she's faced the challenges of navigating a man's world and brings that expertise to her engagements. Through lived experience with multiple twists and turns, Ann has carved out a path to success and personal happiness.

Throughout her career, Ann has presented to both large and small audiences, designed & facilitated workshops, and delivered small group coaching programs both virtually and in person. Ann brings her vulnerability, curiosity, authenticity, humor and experience to all her engagements to the delight of participants. Clients engage Ann for her practical, interactive sessions and workshops that blend concepts, stories, activities, and tool practice.

Ann holds a Bachelor of Arts from Colby College and a Master of Business Administration from Boston University. She is a certified Executive Coach (Center for Executive Coaching) and a certified mediator (Southern Methodist University).

Passion

I have multiple passions:

1) I'm passionate about supporting women in their quests to understand and shift behaviors that while well intentioned, often get in the way of their professional and personal goals.
2) I'm passionate about driving teams to functioning as high performing teams (not simply a group of individuals) through productive conflict, psychological safety and aligned goals.
3) I'm passionate about helping others, particularly those who are less privileged, find their voice and build their confidence in today's competitive workplace.
4) I'm passionate about empowering mothers and fathers to claim their power when navigating challenges with children with special needs.

Best Story

I was steadily building my career on the leadership track at a large U.S. healthcare company. I felt challenged, supported, and genuinely optimistic about where things were heading. Life had a rhythm to it—two kids in elementary school, work I enjoyed, a sense that things were really clicking. And then one evening my husband walked in, took a breath, and said, "I got offered a job. In England.” England. Wonderful for him. Complicated for me. He asked what I thought, and suddenly the trajectory I’d been shaping for years had a plot twist worthy of its own theme music.

I’d moved for his job before, and my company had always found a spot for me. But they were strictly U.S.-based. This time, if we moved, I’d be giving up a role I loved with no clear path on the other side. Add two kids who would have to start over in a new school system, and you can imagine my internal monologue: Is this wise? Is this nuts? And why did he get the exciting international job offer first? And honestly? A part of me felt disloyal—to myself, and to every woman who’d fought for her career. Was I really going to step aside so he could step forward? But when I got quiet with myself, I realized something uncomfortable: I wasn’t hesitating because I didn’t want change. I was hesitating because I was scared. I had always relied on luck, timing, and relationships to guide my next career step. I hadn’t often paused to ask: Is this what I genuinely want? Does it align with my values? Is this the kind of culture that fits who I am? (Thankfully, my current role did—but that was more serendipity than strategy.)

Underneath that was a deeper truth: I wasn’t confident I could adapt to a completely new country and culture. The uncertainty felt huge, and I wasn’t sure I had the courage for it. But I also knew this: I valued learning. I valued new experiences. And—I’ll admit this—I’d always dreamed of living abroad. Not the “visit for a week and come home with too many photos of old buildings” kind of experience, but truly living somewhere else. Plus, I wanted my daughters to see the world up close, not just in textbooks. And if you’re going to uproot your life, England is at least a place where I spoke the language - more or less! When I looked at it through that lens, the decision shifted. This wasn’t just his opportunity. It could be mine too—if I was brave enough to claim it.

So we leapt. And it turned out to be one of the best decisions of my life. Professionally, I joined the National Health Service, led a diverse team, and learned socialized medicine from the inside. Personally, we lived in one of the most international cities in the world, traveled all over Europe, and watched our kids become confident, resilient global citizens. But the biggest change happened in me. I learned I could take a risk without being reckless. I learned courage is all about moving into uncertainty. And I learned that staying comfortable might feel safe—but it won’t take you very far. Those insights have stayed with me every time I’ve reached a crossroads. Because stepping into the unknown didn’t just take me to London. It took me to a new understanding of who I am and what I’m capable of.

Origin Story

For someone who had planned her career path as a college sophomore, my actual professional journey can only be described as meandering. Despite the best laid plans, life sometimes has other things in mind - a husband's job offer in another country, a child born prematurely with multiple health issues, a loss of a job at age 62. Each opportunity along the way has provided me with incredible experiences - an opportunity to work and live in another country, an understanding of how to navigate the powerful force of health insurance and school systems that I can share with others, and the opportunity to forge my own path as an entrepreneur doing what I love the most - speaking, facilitating, teaching and coaching. And because I have worked for the most part in a man's world - sometimes definite "bro cultures" - I have learned how to thrive by shifting some habits while maintaining my authenticity, because I've realized we can't wait for the systems to change.

Example Talks

Against All Odds: Navigating the Healthcare Maze as a Parent and Professional

When a child is critically ill, parents expect the healthcare system to be a source of support. Instead, many discover a confusing, bureaucratic maze where every decision feels high-stakes. In this talk, I share my journey as a working mother - ironically in the health care world - whose prematurely born daughter spent six months in the hospital and required four years of in-home nursing care.  We saw the best and the worst of healthcare.  We experienced doctors and nurses who rallied to save our daughter and give her wonderful care - care our insurance provider attempted to take away despite her need for 24-hour support.

Without a law firm willing to take our case, we represented ourselves in court. We faced the system head-on and ultimately prevailed. Today, my daughter is a thriving 28-year-old—but the lessons learned along the way have shaped how I lead, advocate, and support others through high-pressure challenges.

This talk blends personal storytelling with practical guidance for anyone who find themselves navigating complex systems when the stakes couldn’t be higher.  My clear message is:  when the system says "No," don't give up.  

Key Takeaways:

  • How to advocate effectively when you're up against a large institution—and why courage, clarity, documentation, and persistence matter more than perfect expertise.

  • Strategies for staying grounded while juggling work, caregiving, and crisis decision-making.

  • Common pitfalls within the healthcare and insurance systems and how parents and caregivers can anticipate and navigate them.

  • What leadership looks like in real life, not just the boardroom—especially when courage and resilience are required daily.

  • Why storytelling and self-advocacy are powerful tools, and how sharing your voice can change outcomes for those who come after you.

The Power of Productive Conflict: What High Performing Teams do Differently

Did you know that your conflict style is rooted in your family of origin? We bring our conflict styles to the workplace, and many times the clash causes us to shut down or avoid discussion in the name of harmony. High performing leaders and teams do the opposite. Conflict when rooted in trust is anything but destructive. It's a vital source of innovation, accountability and team cohesion. This highly interactive session is designed for all audiences seeking to understand conflict better, get comfortable with conflict and embrace its value in driving higher performance. 

Key areas of focus and takeaways include:

  • Explore the 5 different conflict styles, each style's strengths and weaknesses, and identify our own preferred style
  • Examine the elements of productive conflict and its importance to high performing teams
  • Learn the skills of connective listening and perspective taking
  • Identify the ways leaders should foster productive conflict on their teams

Gravitas: The Elusive Edge for Rising Leaders

In every room of decision-makers, there’s an intangible presence that sets certain people apart. It’s not just expertise. It’s not just confidence. It’s something deeper, subtler, and often described in one word: Gravitas. If you’re a individual advancing into leadership, you’ve probably heard the feedback — directly or indirectly: “You need more executive presence.” “Be more assertive.” Or the most nebulous of all: “You need gravitas.” At its core, gravitas means a certain weight, seriousness, or credibility that makes people listen — and trust your judgment. It’s the quality that helps a leader command respect without demanding it. Technical skills and expertise get you to the table. Gravitas keeps you there and moves you to the head of the table. This interactive session is designed for professionals at any level of an organization.

Key areas of focus and takeaways include:

  • Understand your own gravitas with an individual self-assessment
  • Discern what true gravitas looks and feels like, and its benefits to your work situation
  • Learn practical ways you can cultivate your gravitas and expand your influence

Female Ambition, Unburdened: Smarter Habits for Achieving Your Professional Goals

There's no doubt that women have made great strides in the workforce. And yet, for all that progress, we still know the story isn’t complete. We’re still navigating systems largely built on a male model—frameworks that weren’t designed with women in mind, coupled with systemic bias, conscious and unconscious. While organizations have evolved, they continue to carry the weight of their origins. Unfortunately waiting for the system to catch up simply isn't a strategy. Women need to claim their agency—to recognize and shift the patterns and behaviors that while well-intentioned, keep us stuck. This interactive session is designed for female professionals and anyone who is stuck in their professional life.   

The areas of focus and key takeaways include:

  • Recognize the habits that keep us stuck and get in the way of our professional objectives
  • Understand where these habits originated
  • Learn practical strategies to shift behaviors to achieve our professional objectives
  • Determine where to start for yourself and the tools you need to sustain behavior change

This program can be customized for specific audiences and is offered as an interactive presentation or a workshop.

Topics/Keywords

womens leadership high performance teams accelerating career growth executive presence for women build confidence managing productive conflict workshop facilitator program design overcoming challenges building trust communicating with confidence health care human experience organizational change management empathy in leadership strategy alignment gravitas patient stories psychological safety
I am willing to travel more than 100 miles
Yes
Everything is negotiable

Speaking Engagements

2026 LifeSpan Network Annual Conference and Expo

Ocean City, MD, USA, 09/22/26

Best Story

I was steadily building my career on the leadership track at a large U.S. healthcare company. I felt challenged, supported, and genuinely optimistic about where things were heading. Life had a rhythm to it—two kids in elementary school, work I enjoyed, a sense that things were really clicking. And then one evening my husband walked in, took a breath, and said, "I got offered a job. In England.” England. Wonderful for him. Complicated for me. He asked what I thought, and suddenly the trajectory I’d been shaping for years had a plot twist worthy of its own theme music.

I’d moved for his job before, and my company had always found a spot for me. But they were strictly U.S.-based. This time, if we moved, I’d be giving up a role I loved with no clear path on the other side. Add two kids who would have to start over in a new school system, and you can imagine my internal monologue: Is this wise? Is this nuts? And why did he get the exciting international job offer first? And honestly? A part of me felt disloyal—to myself, and to every woman who’d fought for her career. Was I really going to step aside so he could step forward? But when I got quiet with myself, I realized something uncomfortable: I wasn’t hesitating because I didn’t want change. I was hesitating because I was scared. I had always relied on luck, timing, and relationships to guide my next career step. I hadn’t often paused to ask: Is this what I genuinely want? Does it align with my values? Is this the kind of culture that fits who I am? (Thankfully, my current role did—but that was more serendipity than strategy.)

Underneath that was a deeper truth: I wasn’t confident I could adapt to a completely new country and culture. The uncertainty felt huge, and I wasn’t sure I had the courage for it. But I also knew this: I valued learning. I valued new experiences. And—I’ll admit this—I’d always dreamed of living abroad. Not the “visit for a week and come home with too many photos of old buildings” kind of experience, but truly living somewhere else. Plus, I wanted my daughters to see the world up close, not just in textbooks. And if you’re going to uproot your life, England is at least a place where I spoke the language - more or less! When I looked at it through that lens, the decision shifted. This wasn’t just his opportunity. It could be mine too—if I was brave enough to claim it.

So we leapt. And it turned out to be one of the best decisions of my life. Professionally, I joined the National Health Service, led a diverse team, and learned socialized medicine from the inside. Personally, we lived in one of the most international cities in the world, traveled all over Europe, and watched our kids become confident, resilient global citizens. But the biggest change happened in me. I learned I could take a risk without being reckless. I learned courage is all about moving into uncertainty. And I learned that staying comfortable might feel safe—but it won’t take you very far. Those insights have stayed with me every time I’ve reached a crossroads. Because stepping into the unknown didn’t just take me to London. It took me to a new understanding of who I am and what I’m capable of.

Origin Story

For someone who had planned her career path as a college sophomore, my actual professional journey can only be described as meandering. Despite the best laid plans, life sometimes has other things in mind - a husband's job offer in another country, a child born prematurely with multiple health issues, a loss of a job at age 62. Each opportunity along the way has provided me with incredible experiences - an opportunity to work and live in another country, an understanding of how to navigate the powerful force of health insurance and school systems that I can share with others, and the opportunity to forge my own path as an entrepreneur doing what I love the most - speaking, facilitating, teaching and coaching. And because I have worked for the most part in a man's world - sometimes definite "bro cultures" - I have learned how to thrive by shifting some habits while maintaining my authenticity, because I've realized we can't wait for the systems to change.

I am willing to travel more than 100 miles
Yes
Everything is negotiable

Example Talks

Against All Odds: Navigating the Healthcare Maze as a Parent and Professional

When a child is critically ill, parents expect the healthcare system to be a source of support. Instead, many discover a confusing, bureaucratic maze where every decision feels high-stakes. In this talk, I share my journey as a working mother - ironically in the health care world - whose prematurely born daughter spent six months in the hospital and required four years of in-home nursing care.  We saw the best and the worst of healthcare.  We experienced doctors and nurses who rallied to save our daughter and give her wonderful care - care our insurance provider attempted to take away despite her need for 24-hour support.

Without a law firm willing to take our case, we represented ourselves in court. We faced the system head-on and ultimately prevailed. Today, my daughter is a thriving 28-year-old—but the lessons learned along the way have shaped how I lead, advocate, and support others through high-pressure challenges.

This talk blends personal storytelling with practical guidance for anyone who find themselves navigating complex systems when the stakes couldn’t be higher.  My clear message is:  when the system says "No," don't give up.  

Key Takeaways:

  • How to advocate effectively when you're up against a large institution—and why courage, clarity, documentation, and persistence matter more than perfect expertise.

  • Strategies for staying grounded while juggling work, caregiving, and crisis decision-making.

  • Common pitfalls within the healthcare and insurance systems and how parents and caregivers can anticipate and navigate them.

  • What leadership looks like in real life, not just the boardroom—especially when courage and resilience are required daily.

  • Why storytelling and self-advocacy are powerful tools, and how sharing your voice can change outcomes for those who come after you.

The Power of Productive Conflict: What High Performing Teams do Differently

Did you know that your conflict style is rooted in your family of origin? We bring our conflict styles to the workplace, and many times the clash causes us to shut down or avoid discussion in the name of harmony. High performing leaders and teams do the opposite. Conflict when rooted in trust is anything but destructive. It's a vital source of innovation, accountability and team cohesion. This highly interactive session is designed for all audiences seeking to understand conflict better, get comfortable with conflict and embrace its value in driving higher performance. 

Key areas of focus and takeaways include:

  • Explore the 5 different conflict styles, each style's strengths and weaknesses, and identify our own preferred style
  • Examine the elements of productive conflict and its importance to high performing teams
  • Learn the skills of connective listening and perspective taking
  • Identify the ways leaders should foster productive conflict on their teams

Gravitas: The Elusive Edge for Rising Leaders

In every room of decision-makers, there’s an intangible presence that sets certain people apart. It’s not just expertise. It’s not just confidence. It’s something deeper, subtler, and often described in one word: Gravitas. If you’re a individual advancing into leadership, you’ve probably heard the feedback — directly or indirectly: “You need more executive presence.” “Be more assertive.” Or the most nebulous of all: “You need gravitas.” At its core, gravitas means a certain weight, seriousness, or credibility that makes people listen — and trust your judgment. It’s the quality that helps a leader command respect without demanding it. Technical skills and expertise get you to the table. Gravitas keeps you there and moves you to the head of the table. This interactive session is designed for professionals at any level of an organization.

Key areas of focus and takeaways include:

  • Understand your own gravitas with an individual self-assessment
  • Discern what true gravitas looks and feels like, and its benefits to your work situation
  • Learn practical ways you can cultivate your gravitas and expand your influence

Female Ambition, Unburdened: Smarter Habits for Achieving Your Professional Goals

There's no doubt that women have made great strides in the workforce. And yet, for all that progress, we still know the story isn’t complete. We’re still navigating systems largely built on a male model—frameworks that weren’t designed with women in mind, coupled with systemic bias, conscious and unconscious. While organizations have evolved, they continue to carry the weight of their origins. Unfortunately waiting for the system to catch up simply isn't a strategy. Women need to claim their agency—to recognize and shift the patterns and behaviors that while well-intentioned, keep us stuck. This interactive session is designed for female professionals and anyone who is stuck in their professional life.   

The areas of focus and key takeaways include:

  • Recognize the habits that keep us stuck and get in the way of our professional objectives
  • Understand where these habits originated
  • Learn practical strategies to shift behaviors to achieve our professional objectives
  • Determine where to start for yourself and the tools you need to sustain behavior change

This program can be customized for specific audiences and is offered as an interactive presentation or a workshop.

Speaking Engagements

2026 LifeSpan Network Annual Conference and Expo

Ocean City, MD, USA, 09/22/26

Topics/Keywords

womens leadership high performance teams accelerating career growth executive presence for women build confidence managing productive conflict workshop facilitator program design overcoming challenges building trust communicating with confidence health care human experience organizational change management empathy in leadership strategy alignment gravitas patient stories psychological safety