Some conversations leave you with a simple feeling: clarity. In this episode, Alexis speaks with Ashley Freeman, founder of Flourishing Work, about purpose, trust, and the kind of leadership that helps people grow.
Ashley's story begins in medical research, where she experienced both great and not-so-great bosses. That contrast sparked a question that stayed with her: what makes good leaders good? She went on to study leadership formally — but the real turning point came when she became a people leader for the first time. Within six months, she knew what she wanted to do for the rest of her life: lead, and help others learn how to lead.
They discuss Ashley's working definition of leadership ("taking care of people"), her Saturday-morning book club, the personal-brand work she does with leaders, why diverse teams produce better work, and her upcoming book The Path to Your Career Purpose.
In this episode, we discuss
- •From medical research to founding Flourishing Work — what good and not-so-good bosses taught Ashley about leadership.
- •Leadership is taking care of people (Simon Sinek) — and you don't need direct reports to lead.
- •Continuous learning, made real: a Saturday-morning book discussion club that has run for years.
- •Personal brand: everyone has one — managed or not — and you can shape the blank in "What a ___ they are."
- •Why clarity of values builds deeper trust than shared job titles or neighborhoods.
- •Myers-Briggs and team dynamics: similar teams move fast and share blind spots; diverse teams produce better work.
- •Handling conflict by helping each side see the value the other brings — efficiency and empathy as complementary strengths.
- •The Path to Your Career Purpose: everyone has a unique combination of passions and talents — and deserves good leaders when they arrive.
References mentioned in the episode
- Original blog post — The Path to Purpose with Ashley Freeman
- Flourishing Work — Ashley Freeman's company
- The Path to Your Career Purpose — Ashley Freeman's book.
- Simon Sinek — on leadership as taking care of people.
- Myers-Briggs Type Indicator (MBTI) — used in Ashley's team work.
Transcript
Alexis:
Hey Ashley, how would you describe your role to someone you just met?
Ashley:
I am the owner and founder of Flourishing Work, which is a company based here in the US that provides facilitation and coaching services to leaders of all walks of life.
Alexis:
Tell me more — what was the pivotal moment that led you to found Flourishing Work?
Ashley:
Great question. My background is in medical research, supporting the efforts of academic medical researchers, and through that experience I — like everyone — had good and not-so-great bosses. It just gave me a real passion for wanting to understand what makes good leaders good, and what makes those leaders that aren't as great. So I ended up getting an MBA in leadership to really study this topic further.
But it was really when I started managing a team for the first time, when I became a people leader for the first time, that everything completely changed for me. I was able to see that the lessons we were learning in the classroom and the theory could actually be put into practice and do some amazing things to help the team really flourish — and the business outcomes to match that level of productivity. About six months into being a people leader I said: this is what I want to do for the rest of my life. Not only lead, but more importantly share how to lead — and not just lead people literally, but also navigate things like difficult conversations. It's the best job in the world.
Alexis:
So you are a leader yourself, and you've worked with a lot of leaders. Among those you admire, what's the one trait that stands out to you?
Ashley:
When I think about what a leader is, I align with one of my favorite authors, Simon Sinek's, definition: taking care of people. The best leaders that I ever had were very invested in my development and giving me opportunities really before I even felt ready for them, and made sure I was okay and that I understood what my role was. It's just taking care of people, and that's why I say — in my opinion — you don't have to have direct reports to be a leader. You can lead anyone.
Alexis:
Taking care of people, in the way you describe it, is also about growing them, helping them grow, and identifying opportunities you believe will be good for them. Something along those lines?
Ashley:
Yes. The best boss I ever had brought me into a lot of meetings and projects that were well outside my immediate job description. I was actually just an administrative assistant at that time — and I say "just" because those projects and meetings had nothing to do with organizing his calendar and booking his travel and the things I was directly responsible for. Yet he brought me into these opportunities for the express purpose of helping me to grow, and I will never forget that.
Alexis:
How did you decide to develop yourself as a leader? What was the one action you've taken to develop yourself?
Ashley:
I have kind of a vague answer to that, because for me I really wanted to understand the theory behind what I knew about who a good leader was and who a not-so-good leader was, but I didn't understand why. So in my case, it really was a lot of studying. I read dozens of books — I still to this day lead a book club every Saturday morning. I never stop learning. I just wanted to have that knowledge so I could then apply it.
Alexis:
I need to ask a follow-up question on one thing you just said — a book discussion club every Saturday morning. Tell me more. Why are you doing that? I guess it will inspire people to do the same.
Ashley:
Absolutely — you don't have to have any experience, I certainly didn't. It started in the very beginning of the pandemic. We just picked a book and set out some dates, and when it was over we didn't want to stop. The first one I only had two participants, and then the group grew significantly — we had probably too many, eleven or twelve, which was a little difficult on the virtual mechanism to really have space for discussion. So we found our stride in the third book and hit around five to seven people, and that core group has been meeting ever since.
Why do we do that? Every week we have this core group of friends and colleagues we can learn together with — but more than that, we're not just reading a book. It certainly provides enrichment beyond what you might read in the book itself. We become friends and colleagues, we guide each other through the process of growing together, implementing and analyzing some of the concepts from the book in our everyday lives, and even hold each other accountable to improve our lives and our work.
Alexis:
I love it. It reminded me of the first book discussion club I went to. I was really taking notes about the book to be sure I'd have something to discuss, and the first person started to speak — and I thought to myself: "it seems we didn't read the same book." The things that were standing out for that person were totally different from me. Of course there were commonalities, but a lot of things I hadn't even seen, or didn't think were as important. So I learned a ton just by sharing what you think is important, listening to others, and saying: wow, that's the next level. And you remember the book and the learnings probably crazy well by doing that. That's what's really cool.
Ashley:
I totally agree. It's an incredibly enriching experience — almost doubling the learning and the content you're taking in. And even more than that, you know these people are counting on you to read this book, so you read a lot more books than you might otherwise. Can't recommend it enough. When I first started, I thought book clubs were for kids — and here I am years later still doing it every week.
Alexis:
I read on your website that you are helping people on their personal brand. Can you tell me more about that idea of personal brand?
Ashley:
Absolutely. We all have one. We all have a brand whether we're managing it or not — whether you're a leader or not, whether you work or not. You have some sort of brand, which is sort of how you come across to other people, and what you're known for. The work I do in that area is around managing one's brand, because you have a lot of control over how people think about you, and it's such a gift to know that.
It can seem like, well, we can't control other people's thoughts. But you really do have so many opportunities and touchpoints — places where you put information about yourself, meetings you attend — to showcase what you want to be known for, which can bring all kinds of opportunities. As an example, let's say you're in sales but you really want to be known more for marketing. Well, which meetings are you included on? Are you in the marketing meetings? If not, you probably want to get in on them, because people can't read your mind. You have to showcase what you want to be known for. Are you on the emails on that topic? If not, how can you be copied? How do people introduce you? What do they talk about when you're not in the room? If they say "oh everybody was talking about you the other day, they just said: what a ___ you are" — well, whatever the blank is, that's your brand. The blank doesn't have to stay where it is. It can be whatever you want, and there are so many opportunities to manage that.
Alexis:
Do you believe that when people know what their brand is, it helps them develop trust with people around them?
Ashley:
I do, and the reason why is because when we're clear on what we stand for and what we value, what we like and what we don't like, we naturally attract people who have those similar values. Just to be clear, I'm not advocating against diversity — particularly of thought, because I think that's incredibly enriching. But to develop trust, you can have someone who's very different from you and yet you both really value something like respect.
You can develop a level of trust with them because you know that about each other. Whereas if you weren't making that clear — or you weren't even sure yourself what your brand was, or what you cared about — then it's pretty hard to find other people who share those same values.
Alexis:
So showing who you are and being clear about the values that are important to you — that's building that trust, that relationship, at a deeper level.
Ashley:
Yes, much deeper than "we have the same job title" or "we live in the same neighborhood." It's: we care about the same things, even though we may disagree on many other things. The core of who we are and what we care about is very similar. And almost ironically, that actually opens up the opportunity to get to know people who are very different from you, who you might not naturally think you'd get along with, and yet you realize that at the core you actually do value the same things — and it becomes much easier to build trust that way.
Alexis:
You mentioned diversity, and the way you talk about the topic reminded me of a quote from Lincoln — I'll paraphrase: "I don't like that man much. I need to get to know him better."
Ashley:
Yes, I love that — I want to jump up and clap. I absolutely love that mentality. I see it a lot in the personality work I do. I'm a Myers-Briggs practitioner, and the research I've seen shows that when you have that completely different perspective on the same team working together, your work product is better.
Alexis:
I've used MBTI before, and other personality profile tools with teams, and it's incredible to see that with some teams everybody was nearly on the same side of the quadrant, and in other teams it was very well-balanced. You can see the result on what the team is able to do.
Ashley:
Any personality assessment is very helpful because it helps you understand yourself and how you're different or similar to others — those insights are incredibly valuable. Myers-Briggs in particular I find works best with teams because it looks at how clearly you prefer different ways of taking in information and making decisions about that information. And if you think about it, taking in information and making decisions with that information — is that not what teams do all the time?
Without fail, when I have a team that is more similar in thought and personality type, they have the same blind spots. They get along great, they enjoy each other's company, they get things done very quickly because they all agree on everything — but they also have the same blind spots. The teams that are less similar tend to come to me because they're having communication or conflict issues. When we break it down, it's a very touching moment, really, in a corporate setting where you wouldn't expect it to be. Once we get all the personalities up on the screen and start to see the bigger picture of how we're different and how we need each other, you just see the light bulb go on. It's not just "oh, I don't like that person because they're not like me" — you start to realize not only why they're like that, but how much you need that different perspective to do better work.
Alexis:
When you have those people in the room and you help them collaborate, I can imagine it can become really intense and could even reveal conflict. How do you handle conflicts and help the conversation move forward?
Ashley:
It really comes down to helping both sides see the value the other one is bringing. For example, in the Myers-Briggs context, I'll often see a dichotomy between those who are very efficient and effective versus those who are very people-oriented and empathetic — not to say we can't be both, but for whatever reason coaching clients tend to go into those buckets.
With the ones who are very efficient and effective, we start by saying: yes, that's incredibly important and what a gift that strength is, because the rest of us would never get anything done without you. At the same time, listening is really important, and developing those relationships actually becomes more efficient and effective in the long term, because the people you've built relationships with want to work with you and trust you. On the other side, if someone is really focused on building relationships and listening and being empathetic, they may not get as much work done as their colleagues would like — and then they get a perception, back to our point about personal brand: maybe a brand of "they aren't effective." In those conversations, you start to see that person is not just ineffective or hard-driving, you start to see what their strengths are and why you need them. You get an appreciation for why you need that other perspective to get the job done better. It's in the combination that we succeed, not in the collective blind spots where it's more comfortable and more fun to be.
Alexis:
I really like the way you frame all that. You have something very exciting coming — I need to speak about that. You worked on the book for the last two years, something like that, right?
Ashley:
Yeah, one year and a half!
Alexis:
And the book is coming right now?
Ashley:
It is. We are hoping to target a mid-July publication date.
Alexis:
Excellent. So tell us more about the book.
Ashley:
Absolutely. I'll tell you in the frame of putting the pieces together that we've talked about. The book is called The Path to Your Career Purpose. Finding purpose in one's work is something I'm very passionate about.
The way that connects to leadership and coaching and facilitation is that I have a couple of beliefs. One is that I believe we all have a career purpose — a set of unique passions, things we're very passionate about doing, and a unique set of talents or skills, our tools in our toolkit to carry out those passions in the world. No two people have the same combination of those two things. One of my passions is to bring whatever that is for any individual on the planet out into the world, because what I've seen in my work is that too many people are doing work that just provides for the family or pays the bills. That's very important — I'm not diminishing it. But what I've found in my journey is that you can do both. You can pay the bills, you can provide for your family, you can build the lifestyle you want, and do work that is incredibly fulfilling. That's what the book teaches the reader to do: go from wherever you are today to living a life of fulfilling work that I would call what you were meant to do.
The second belief I have is that we all deserve to have good leaders waiting for us when we get to whatever that dream job is. In the book I talk about how you'll have many dream jobs over the course of your career — they're just one point along the journey. But when you get there — whether that's being a stay-at-home parent, working in a corporate setting, nonprofit, retirement, whatever your job is — I think we all deserve to have good leaders who help bring out the best in us. That's how the pieces connect: I'm bringing out unique gifts and passions through this book, and then I'm teaching workshops and doing executive and leadership coaching to help people become those leaders. So when you get to that dream job using the methodology in my book, you have the supportive environment you need to flourish in your work — which is the name of my company.
Alexis:
I love it. The book is on my reading list. You convinced me. I love the energy, I love the passion. And I understand way better now where you're saying a leader is someone who takes care of people. I love it. Thank you very much, Ashley, for joining the podcast today.
Ashley:
Absolutely, it's been my pleasure.

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