“I absolutely love what I do because I get to uncover the unique strengths and leadership potential that already exist within people and teams,” Rooted Cultures Founder Lindsay Bailey said.
The primary tool the team uses is the Enneagram, a personality typing model that helps people understand why they think, communicate, and respond to challenges the way they do. While many assessments focus on what people do, the Enneagram helps uncover why they do it. Bailey has found that when people understand what motivates them, they become much more intentional about how they lead and relate to others. Using the Enneagram with leaders helps them become better equipped to understand what motivates their employees, how different people communicate, and how to bring out the best in the people they lead. It also helps team members better understand one another and appreciate perspectives that may be very different from their own.
In addition to workshops and coaching, Bailey partners with organizations to connect insights into their culture. Through fractional consulting, onboarding, leadership development, and coaching, she helps companies create a shared language that supports growth long after a workshop is over.
AZF: What is your “life motto”?
There is a saying in Proverbs that guides me in every area of my life: “Do not be wise in your own eyes.” It reminds me that we need sources of wisdom outside of ourselves. I rely on the wisdom of God and the wisdom of others to help develop wisdom within myself. When we only rely on seeing life through our own lens, there is so much we can miss. Some of the greatest growth in my life has come from being willing to listen, learn, and consider perspectives that are different from my own.
I often tell leaders that most teams are already in the boat and rowing hard. The challenge is that they are often rowing in different directions. Using the Enneagram to build trust and create a shared team language helps people understand both their own gifts and the gifts of those around them. When team members bring their unique strengths to the boat, they learn how to row in the same direction. The result is a team that is aligned, effective, and moving forward more efficiently.
AZF: Did you always know that you wanted to be an entrepreneur? If not, when did you realize that it was the right path for you?
I was raised in a family of entrepreneurs, so owning a business always felt like a possibility. My mom, who raised me as a single mother, encouraged me from a young age to think independently, create opportunities, and not be afraid to build something of my own. She often reminded me that depending entirely on someone else for your livelihood comes with risks, and that lesson stayed with me.
AZF: How do you feel best supported?
I feel most supported by wise mentors who are willing to share their experience and lessons learned. I often say that I stand on the shoulders of very generous people. Throughout my career, I have had mentors who invested their time in training me, challenging me, and helping me refine my coaching process. Their investment has shaped both who I am and the work I do today.
AZF: What motivates you to keep going amidst the challenges that come with being an entrepreneur?
What keeps me going is people. I never get tired of meeting new people and hearing their stories. I have an unlimited amount of energy for learning about what drives and motivates people. The bigger challenge for me has always been the day-to-day operational side of running a business.
Those organizational tasks require a different kind of energy and can consume a lot of mental bandwidth. One of the things I am most excited about right now is how AI is already helping alleviate many of those responsibilities. It allows me to spend less time on administrative tasks and more time doing the work that energizes me most: developing people and helping leaders and teams grow.
AZF: Describe your perfect Saturday.
My perfect Saturday morning is sitting on a restaurant patio with my husband and kids, enjoying breakfast and taking our time. No agenda, no rushing, just good food, good conversation, and being together.
AZF: What’s one piece of advice you’d give to a young entrepreneur who is just starting out?
One piece of advice I would give a new entrepreneur is to invest in self-awareness as early as possible. Building a business will expose your strengths, blind spots, motivations, and stress patterns faster than almost anything else.
I recommend starting with a quality Enneagram assessment that includes both Type and Subtype, then using AI as a personal growth tool to help you identify patterns, create a growth plan, and better understand where you excel and where you need support. The sooner you understand yourself, the sooner you can spend more time in your zone of genius and delegate the areas that are not.
AZF: What excites you most about being an entrepreneur?
What excites me most about being an entrepreneur is the freedom to build a business around work that aligns with my own personality strengths. I have always considered my creativity to be relational. I am endlessly fascinated by what drives and motivates people to do what they do and how their beliefs about themselves shape the way they show up in the world.
Entrepreneurship has given me the opportunity to channel that passion into meaningful work. Whether I am working with a leader, a team, or an organization, there is something rewarding about uncovering strengths, challenging limiting narratives, and helping people recognize potential they may not see. That is what excited me about starting Rooted Cultures, and it is what continues to excite me about the work today.
Learn more about Rooted Cultures by visiting rootedcultures.com or following along on Instagram @rooted.cultures
About the Foundress
The Foundress is a creative community of female entrepreneurs established by Coley Arnold. The women-led networking group currently has over 120 members who receive exclusive access to mentorship from experienced female entrepreneurs and industry leaders; community gatherings that feature expert speakers and the opportunity to connect with like-minded women; as well as monthly Mastermind Groups where members can brainstorm and collaborate together. Learn more at foundress.co.
