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Courageous Authenticity: What It Is—And What It Isn’t
There’s a moment in every leader’s journey when speaking up feels more terrifying than staying silent.
You’re in the room. You feel the tension. You know you see something others don’t. But the voice inside says, “What if this backfires? What if I’m wrong? What if I say too much?”
That’s the crossroads between comfort and courageous authenticity. And for many women leaders especially, it’s familiar terrain.
In a recent episode of The Enlightened Executive, I sat down with Cindy Adams—executive coach, speaker, and co-founder of The Enneagram in Business Network—to explore what true courageous authenticity looks like in leadership today.
And here’s what we uncovered: It’s not just about being bold. It’s about being wise.
Why This Matters for Leaders
Leadership today demands transparency, but not at the expense of impact.
We’ve been told authenticity means speaking your truth. But unfiltered expression isn’t always useful, especially in high-stakes environments. When you blurt, broadcast, or bare all without context, you risk undermining the very influence you’re trying to build.
That’s why courageous authenticity is a practice, not a personality trait.
It means knowing:
- When to speak and when to pause
- How to frame truth so it can be received
- Why your authenticity serves the mission, not just your ego
And most importantly, it means aligning what you say with how you want to lead.
The Science Behind the Shift
Neuroscience shows us that the brain perceives social rejection as physical pain. That’s why speaking up, especially when your view diverges, can feel like a risk to survival.
For women leaders and underrepresented voices, that risk often feels even more real.
But here’s the paradox: leaders who withhold too much create disconnection. And those who overshare without intention dilute their influence.
Courageous authenticity lives in the balance.
It’s where vulnerability meets discernment.
This is where tools like the Enneagram offer such valuable insight. Because how we perceive authenticity, and how we express it, varies dramatically based on our type.
Your Enneagram Type Shapes How You Show Up
In our conversation, Cindy shared her personal evolution: how she once believed courage meant saying everything. But as her leadership matured, she discovered that wisdom often lies in the how and when, not just the what.
This insight plays out across all Enneagram types:
- A Type 2 (The Supporter) may hesitate to speak up for fear of seeming selfish.
- A Type 3 (The Performer) might share what’s strategic but withhold what’s vulnerable.
- A Type 6 (The Troubleshooter) may rehearse authenticity so much it loses its spontaneity.
Each type has its own reflexes—some help, some hinder.
The goal isn’t to suppress your natural instincts.
It’s to elevate them. To bring self-awareness to the front of the room.
Action Steps You Can Take This Week
If you want to build more courageous authenticity into your leadership, here’s where to begin:
- Map Your Reflexes
Notice what you do when things feel tense or uncertain.
Do you power through, over-explain, withdraw?
That’s a pattern, and it’s trying to keep you safe. Recognizing it is your first step to choice. - Use the Pause + Purpose Formula
Before you speak up, pause.
Ask: What’s the outcome I want? Who is this serving?
Courage without clarity can cause confusion. Clarity without courage can become avoidance. You need both. - Tailor Your Expression Through Your Enneagram Type
Your Enneagram type shapes your blind spots.
Use courses like our Enneagram Applied course to explore how your instincts influence communication, conflict, and collaboration. - Reframe What Courage Means
Courage isn’t always loud.
Sometimes, it’s the decision to wait until your message has the best chance to land.
Sometimes, it’s asking a question instead of making a point.
Sometimes, it’s being silent when your old pattern would speak to seek validation. - Reflect on a Time You Missed the Moment
We all have those moments.
What held you back? What would you try now with the awareness you have today?
That’s how you build wisdom. Not through perfection—but through reflection.
Final Thought: Authenticity Is Not a One-Time Act
It’s easy to think authenticity is a checkbox.
“I spoke my truth.” Done.
But courageous authenticity is a continual calibration between honesty, timing, and intention.
It’s the ability to show up fully, but also skillfully.
Because the most influential leaders don’t just share what’s real.
They do it in a way that moves things forward.
And that’s what we’re all after, isn’t it?
Want to understand how your Enneagram subtype shapes your courage, communication, and leadership presence?
👉 Take the Enneagram Applied Assessment
Episode Transcript
Susan Drumm: What if unlocking your highest level of leadership wasn’t about working harder, but evolving who you are at the core by leveraging courageous authenticity? Today’s guest has helped transform leaders at Pixar, Ro, Yale, and beyond. She’s built global businesses, authored books, and created one of the most influential leadership frameworks in the world. She doesn’t just teach leadership — she redefines it.
Hi, I’m Susan Drumm, and this is The Enlightened Executive, where your personal evolution sparks your leadership evolution. Each week, we spotlight cutting-edge strategies to help executives and entrepreneurs grow in leadership and in life. And today I couldn’t be more excited to introduce my friend and colleague, Cindy Adams of the Leadership Circle, who provides strategic training tools that I’ve been using in my coaching for more than a dozen years.
Cindy co-founded Full Circle Group, the consulting arm of the Leadership Circle, and is passionate about enabling leaders and organizations to build capability and capacity for creating what matters most to them. Cindy has extensive experience in leadership development, adult development, organizational effectiveness, and transformation, and utilizes a whole-system solution to help leaders achieve desired results.
In her early career with the U.S. Department of Education, she enabled and mentored homeless and disabled populations to acquire meaningful jobs and careers. In that role, she trained leaders to create second chances. That work ignited a lifelong commitment to enabling a world in which all people can thrive.
Well, welcome to the show, Cindy. I’m so excited to have you here. How we got connected was many years ago, through Bill Adams, who is also co-founder of the Leadership Circle, and it’s exciting to have you on the show. And you know, just for listeners, the Leadership Circle has been a really powerful leadership development model and 360 instrument that gives you feedback on how your leadership is being actualized in the world — with your peers, direct reports, boards, or CEOs — and you’ve been instrumental in bringing this to the world. So, I’m excited to have you on the show.
Cindy Adams: I am so excited to be with you in particular, Susan, and thank you for inviting me. I am thrilled to be here with you today.
Susan Drumm: Yeah. Great, great. So, you’ve had quite a journey — let’s start a bit with your journey. What’s your journey to more conscious leadership been like, and what’s helped you the most along the way?
Cindy Adams: Oh, it’s such a great question, and it’s a really thought-provoking one for me. First and foremost, I would have to say that it might be a reach to say that I am really that fully conscious leader, because I think we are all so human in it, right?
Susan Drumm: Yes, you’re a work in progress.
Cindy Adams: I am a full work in progress, and a piece of work. I have often referred back to Warren Bennis — I love his definition of leadership when he says the process of becoming a leader is similar to, if not identical to, becoming a fully integrated human being. So that level-sets it for me. I had a crush on, you know, Warren Bennis in terms of his work and his impact in the world, and I still fall back to that — that leadership is just a way of talking about the development process of becoming a fully integrated human being. And boy, do we need more fully integrated human beings. Now, we’ve always needed it, but wow.
So, my journey — just a couple of pieces I think that really—
Susan Drumm: Oh, wait — before you go into that—
Cindy Adams: Oh, yeah.
Susan Drumm: —maybe you can elaborate. What do you mean by a fully integrated human being?
Cindy Adams: So, when I think of a fully integrated human being, I think of a human being that is already complete and whole just as they are — like that internal soul. And yet there are so many pieces through childhood, and what got us here, that we kind of disown or choose not to look at. One for me was: as long as I look good — the looking-good part was really important — and that’s not integrated, that’s not radical humanity, that’s not being vulnerable.
So I took a lot of stuff out in a search for “make sure you look good, make sure that people think you’re competent.” So the integrated piece is to just accept the fullness of who we are, and to work on the fullness of who we are, to allow it all in.
Susan Drumm: Yeah, yeah. Great, great — that’s helpful. I see looking good as a typical place that people can go to. There’s others, right? There’s being in control.
Cindy Adams: Yes.
Susan Drumm: Being right.
Cindy Adams: Yes.
Susan Drumm: You know, that looking-good piece, and — or even being included. And what I find is there’s sort of, in those four, one that becomes more dominant. It’s sort of the dominant subconscious voice that is driving certain leaders, and it’s running in the background. They think — or we think — we’re hiding it, but everyone else can see it.
When it’s like, if you’re more committed to looking good than you are to the stated mission that you say you’re after, everyone can see that that’s actually what’s driving the show, versus what you say — “No, I’m really committed to doubling revenue and tripling profit,” or whatever metric or KPI you set out. And I think that a fully integrated human being understands that that might be underneath their actions, and is working on that and healing that need for others to see them in a certain way.
Cindy Adams: Yeah, I love that, Susan. And what you described is a little bit about the Leadership Circle model, and how we wire up our identity. Our identity is wrapped, early on, in a lot of ego, which keeps us safe and maybe got us here but won’t get us there — it helps us feel worthy in situations, but it’s such a big shield that we can’t see, necessarily, or we think we’re hiding it, like you said, and it has a costly impact on results — in ourselves and our families.
Susan Drumm: Yeah, yes, yes. So, let’s go back to where you were starting with your journey.
Cindy Adams: Yeah. So, I think, early on, for sure my superpower became “I am what I do” — and getting really good at outdoing pretty much everyone around me. Work ethic: I’m going to work harder, I’m going to work faster, I’m going to outdo — and looking good is the facade behind that. I do because I need to look good, and I need to have opportunities, and I need to be successful. If all of those things align, then I’m okay; if those things don’t align, I’m not okay.
So, what really helped me initially with some of that is — not only being in employment positions, but a couple of pivotal ones, and then also being a mom and getting a divorce. Those were big things. Early on I worked with the homeless population and the disabled population — I have an organizational background, around organizational behavior, and I started using that at the Department of Education, where I was working with how might we look at homelessness as a kind of community behavior, and how does that work. And I saw so many self-sabotaging behaviors that were triggered by such pain.
And of course, it was that — hurt people are hurt, and they’ve hurt people, and they can’t figure out how to get out, because they’ve had a lot of bad choices that have led to — some chosen, some imposed on them — that led to that circumstance. And it opened up a place of empathy for me that I didn’t have before. I started to think about what if we created a world in which all people could thrive, a society in which all people could thrive. So that’s just kind of one ambition that pulled through me.
The other side, of course, was all the ways in which I was failing — I mean, you wouldn’t call it total failure, you’d call it being human — but wow, did I have a first marriage that failed, spectacularly, for me, with two young children, thinking I had it all together, thinking that I was better-than because I was the one that was doing, I was the one that was on top of things, I was the one making the money.
And not recognizing, until after — some space in there — that I had a lot to look at. I mean, I really had a lot to look at. My daughter, this still kills me — I think she was about ten — she said, “Mom, I am the one thing that’s always in your way of you getting done what you need to get done.” And I just went—
“Wow.”
Susan Drumm: Yeah.
Cindy Adams: Just — you know, just — yeah. And it did, it’s just like, you know, the wisdom of children. I had no idea — we were talking about it earlier — I had no idea I was having that impact, but she was right. She was right. I was so busy in my mind, thinking about the task and the accomplishment, that of course she felt like I wasn’t giving her true resonance and being present, and investing in her feeling.
And all of that gets wired back from that initial — well, if I need to look good, then I need to perform and outperform, or overinvest, or overfunction — and then I lose sight of everything else because I have this belief.
Susan Drumm: I mean, I can so relate to that. I remember that it got hardwired in for me, on my first review in the working world — I remember on that review it literally said, “She appears young, and people don’t trust her.” Well, I was young — it was my first job out of law school, I was in consulting, I guess I would have been twenty-four or whatever — and so that stung, in a way. It’s sort of what you make it mean.
And then it became like, I’ve got to have the professional armor on at all times, and the looking-good looks like — I’m going to show you that I am not — I am serious, I am a businesswoman. And in doing that, it sort of put up this Teflon, because there’s this side of me that’s light and playful and fun — oh, she wasn’t coming out after that. She was no businesswoman, right?
And even to this day, I find remnants of it that will show up because it’s been so hardwired. So, I can still relate to that journey of really recognizing: what was that first commitment that you made, that you felt you needed to overcome to survive in the world, and how is it still running you today?
Cindy Adams: Absolutely. Yeah, I relate to your story a hundred percent as well. I mean, I looked younger than I was anyway. And so you wire up “a woman,” you wire up “younger,” and then you wire up some of those old stories. You can see how you would put a bunch of stuff in the closet — and I sure did.
Susan Drumm: Yeah.
Cindy Adams: I remember somebody saying, “You’ll like that when you’re older.” And it’s true — however, back then it just wasn’t so good. I don’t think that promise was as true as I needed it to be, though — now it is.
Susan Drumm: Yeah. Right, right, right, right. So, what has been most helpful to you — what tools have you leveraged in order to help you make some of these transitions, or help you along the growth journey?
Cindy Adams: Yeah, I’ve been really lucky in that way. I would say I started out with kind of a sole desire to learn about growth, and a belief that we are built to grow as human beings — I fundamentally believe that. And so when I hit rock bottom with some things, I still held a belief that this would be for my good if I took myself seriously enough to look inside and get underneath what was driving me, and also why I valued certain things and why I didn’t.
One of my biggest levers happened with a book I read — it’s an old one — by Robert Fritz, on the path of least resistance. He does the structural dynamics of getting what you want, and why sometimes you don’t get what you want because you don’t have the right structure. But he posed the question: what if you could create the life you wanted? Susan, I had never thought of that when I read that book.
I never supposed that I could. It was after my divorce when I was reading it, and I just tinkered around and took that seriously — what if I could? That fundamentally shifted something in me that was profound. And then, the other thing I had to let go of — I really had to let go of — was looking good. There was no way to look good in the situations I was in. There was no way.
And I had to embrace not looking good, and being vulnerable, which I’d had big problems with before that point — in a ropes course. Just a real quick story: I had a badass facilitator taking me through a ropes course as part of a program, and she didn’t even know me, and she put this label on me that said what I had to display that day was “vulnerability.” It bugged me so much having it in front of me, because the other side of it was you have to ask for help today. I threw it behind my back, and that moment, it kind of sunk in. I had to embrace that I couldn’t do this alone, and I had to be okay with putting away that costume that looked so perfect.
Susan Drumm: Right, right. And so how has that impacted how you lead today, and what you’re doing in the world?
Cindy Adams: It was an unlocking — those are unlocking moves that happen over time. I had to get courage in being a new kind of human being, and — seeking feedback, that’s another core piece — just seeking feedback. What’s my impact? With my kids, with my husband, at work. I had to get comfortable with hearing back what they would say. And that’s actually kind of hard, at first.
Susan Drumm: Well, yeah — there’s two parts to it. It’s also making it really comfortable for people to be honest with you.
Cindy Adams: Yeah.
Susan Drumm: Right. I mean, what I tell leaders — when they talk about 360 — is, I encourage you to ask for feedback, but depending on how good you are, you might get fifty percent of the truth, twenty percent of the truth. If you use a coach, you might get a little closer to ninety percent of the truth — eighty, ninety — but where are people holding back, for fear of damaging the relationship?
Cindy Adams: Yep.
Susan Drumm: Yeah. And so I think that’s what’s powerful about the Leadership Circle, because it’s anonymous, right? People can share, and it makes it easier, and gives you some kind of quantitative measure of where you’re showing up. But this idea of getting the feedback — you’ve got to make it easy for people to be as honest as they possibly can, recognizing that they’re not incentivized to be honest with you, to some degree.
Cindy Adams: Yeah, to some degree, that’s so true — that’s a good one that you bring up. And yet, you know, when you’ve created a space — this isn’t a once-a-year feedback, this isn’t a one-and-done feedback — this is a genuine, “Hey, what’s my impact right now, on how we’re approaching this work together?” My husband Bill has been so good for me, because we’ve been in a relationship where we were both kind of the controlling — let’s say power-against — in our model. What we affectionately called each other, when we first got married, was Thunder and Lightning. So, an equal response and a real willingness and commitment to learn how to have power-with versus power-over, which is the exact move we need leaders to make. It isn’t about my brilliance, or my power-over — the fact that I know the most, or that I don’t even need to listen to you because I already know — but the move to power-with, for breakthroughs that we can’t have alone.
That relationship with him has been foundational to — oh wait, okay, here’s when power meets power, here’s how this happens, and how do we work together and relate in a way that — we have tons of passion in the relationship, no safety in some ways, until we worked it out. And it was a big learning, like an evolutionary move.
Susan Drumm: Yeah. So, I love this framework that you have, of power-over versus power-with. I think you describe power-over really well — can you say a little bit more about how a leader shows up as power-with, versus based on my seat as CEO, or chief marketing officer?
Cindy Adams: Yeah. The power-with move is that I’m going to let go of my knower and be a learner. So, I have a voice — I don’t let go of my voice, I don’t let go of the fact that I may know some things — but I choose to be in relationship, so that we can collaborate. We can create safe spaces for feedback, so that I don’t have a fixed mindset about “I know,” but I can be a learner that can know more. Jeff Grimshaw, one of our colleagues, says, “I reserve the right to get smarter.” I love that phrase — I can always reserve the right to get smarter. And power-with is about collaboration, teamwork, diverse ideas, understanding that there’s wisdom in the system. I absolutely can’t be a leader that creates collective breakthroughs, and also societal change, if I think I can do that all by myself.
Susan Drumm: Yeah. I mean, at the end of the day, what we say is it’s about creating outcomes and capacity with others — that’s what being a leader is. Otherwise, you’re an individual contributor, right?
Cindy Adams: Otherwise, you’re an individual contributor, and you’re not scaling anyone, or scaling the organization, for outcomes that could be created — if you would only yield your voice, if you would only listen, if you would only truly appreciate this. This comes from a deep caring about people and what they care about. You can’t do that in that other frame.
Susan Drumm: Yeah, yeah. You can’t harness the collective wisdom of what’s there to build something that not one individual person could have done otherwise — that’s what a true team is. And yet I feel like, when you’re working sometimes with teams, it’s still, in their mind, about their individual contribution. You could make the same analogy, of course, to sports teams — you just look at how they operate.
Cindy Adams: And the feedback that we’ve gotten — you can take the best individual contributors and put them all on a team, but if they don’t play well together, you know, we saw that in the Olympics, that doesn’t work. It’s something about the magic of the interrelationship of the people that are there. And what does that require? Understanding what your superpower is, but it’s a limited range of vision — you have a central vision and a peripheral vision, and where you’re looking, that’s what you see, but there’s a whole other realm — what you don’t see, and other people could see. So, you’ve got to be open to that.
I think there’s a lot of work on first mountain, second mountain, first half of life, second half of life, reactive-creative — in our model, adult development. I think early on it’s important to find out what your superpower is, in terms of survival and getting to be a productive citizen in the world, and navigating. And then, the second half of life, it’s more about shedding all of that stuff away — and that’s hard. What I now know is my job as a leader is to enable other people to thrive, to use my voice when it’s needed but not just because I have a power seat, and mostly to be present to what is happening. That requires me to be in tune, even with the spiritual aspect — the universe is here, we’re living in an emerging future, the signs are everywhere around where we can participate and where we’re being called to. So if I can just be present for all of that, in the organization and in my life, that’s the most important thing.
Susan Drumm: So, we started talking earlier on about the importance of courageous authenticity, and how it’s been a linchpin for you. Can you share more about that aspect of leadership, and why it was so critical for your growth?
Cindy Adams: Early on, I worked with a partner who saw something that I didn’t see, for a moment, and he said, “You have a really good intuition — you need to trust that.” That was helpful to me, and it was also going to require a new level of courage for me to step into — especially as a young woman leader — to step into things I didn’t have data for. In the model, our first move is always to get an authentic relationship with myself — know my doubts and fears, know what I want, be clear about who I am in the world. I know the scientific fact that although we share DNA as a human genome, as human beings, there is only one DNA like mine, and that I have a unique gift.
So intuition prompted this idea of — okay, wait a minute, because I was always thinking, “I’m not good enough, I need to just pay attention.” And I got invited to boardrooms too, because I was a woman — you know, the bigger narrative.
Susan Drumm: Yeah.
Cindy Adams: “I’m not skilled enough, I need to get more of this, I need to get more of that.” And he helped me see that — wait a minute, you have really good intuition, you’re more than enough. I didn’t believe it, but that was one test. And I think, so, the first move is to get an authentic relationship with yourself — see your gifts, notice them, and experiment with them. The second is: how do I more authentically be in relationship with others? And that’s where I think courageous authenticity needs to really be well understood — you know this, Susan — the difference between critical and courageous authenticity are two very different things, and yet we all struggle with that, however we identify, because when we’re practicing courageous authenticity, sometimes it’s going to come off harsh, and we’re clunky with it.
I’ve noticed, in particular, that women struggle in this area, because when we’re in a brave moment, stepping into a brave moment, it’s really easy to just go hard, versus our soft startup, and ensuring that we’re coming from a place that is in service of the other and the organization. So for me, that was another big evolutionary move — learning to be courageously authentic without any edge, trusting my intuition, and coming from a clean place, an integrated human being, a clean space.
Susan Drumm: Yeah.
Cindy Adams: Does that make sense?
Susan Drumm: That makes sense. It’s also — what is the motivation behind the communication you’re about to give? Because it’ll be critical if it’s coming from a place of ego, identity, self-image — the “I know better,” power-over, all of those pieces. If it’s coming from a place of the mission that you’re out to accomplish, that’s outside yourself — that matters to you in service of that — I want to be courageously authentic because this mission over here matters so much to me, and it’s in service of getting closer to that. Or, is it in service—
Cindy Adams: Yeah — in service of me being triggered and annoyed by something you just did, which is all ego.
Susan Drumm: Right, right. And it’s hard to distinguish sometimes with that.
Cindy Adams: I’m coaching somebody right now that’s just having a really tough time distinguishing that. They are courageously authentic, and they also haven’t yet refined a way to give that gift in a way it can be received — which is nuanced, around really being present, really being compassionate, and really looking at the full spectrum of how can I be a translator in what isn’t being quite understood, versus the opposer to what is being said. Does that make sense?
Susan Drumm: Yeah. What’s one thing that you would suggest a leader do tomorrow — an action step that they could take to help themselves along this journey?
Cindy Adams: Hard to come down to one thing. I would say: start paying more attention to impact. Is what I’m doing actually creating what I think it’s doing, or what I perceive I’m going after? If those can get closer together, right off the bat, you’re a better leader.
Susan Drumm: Yeah. And part of that, then, is the action you can take is asking: what kind of impact am I having?
Cindy Adams: What kind of impact am I having right now?
Susan Drumm: Yeah. Even in simple things — like you delegate something, you could ask for feedback. How well did I describe that, delegate that to you, hand off that task? But hardly any leader ever asks that question.
Cindy Adams: Hardly anyone ever asks that question. And a delegator—
Susan Drumm: Right?
Cindy Adams: Yeah. How was that? Was that seen as an opportunity, or was that seen as a punishment? And did I give you enough clarity? Are you excited about the fact that that’s delegated to you? It’s just a few things — it doesn’t have to be a big deal. It’s just — just ask.
Susan Drumm: Yeah, for sure. Well, this has been a really enlightening conversation. Thank you for joining us today. Where can people learn more about you and your work?
Cindy Adams: They can go to leadershipcircle.com, or I’m available on LinkedIn for anyone — it’s Cynthia Adams on LinkedIn. I think you’re going to post that. Those are two great places to catch me.
Susan Drumm: Great. Well, thank you so much for being part of this. And if you like this episode, you’re not going to want to miss my interview with Allison Maslan, who uncovers ways to help entrepreneurs build a business that runs without them by leveraging the power of their team. Let’s lead the way.
Hope you enjoyed today’s episode, and I’d like to point you to the next important step. Hit the subscribe button and the bell to get notified when we release new content. I’ll see you on the next episode of The Enlightened Executive.