Understanding Your Team from the Inside Out: How the Enneagram Can Transform Your Workplace with Ashton Whitmoyer-Ober
Episode 50
What if the key to better communication, less conflict, and higher engagement at work wasn't another process, it was actually understanding the people?
In Episode 50 of The People Success Circle, I sit down with Ashton Whitmoyer-Ober, known as Enneagram Ashton, to talk about how the Enneagram at work goes far beyond a personality label. Ashton walks me through why understanding someone's motivation, not just their behavior, changes how we lead, communicate, and collaborate, and shares real examples of what happens when teams actually use it. Keep reading for practical ways to bring this into your own workplace.
In this episode of The People Success Circle, I explore the following:
I learn what the Enneagram is, how it differs from tools like Gallup Strengths and DISC, and why motivation matters more than behavior
I find out why personality tests are only about 60% accurate, and the better way to actually confirm your Enneagram type
I hear how one company dramatically reduced turnover within six months of implementing the Enneagram at work with their team
I cover why employee engagement jumps from 32% to 77% when people feel truly understood and valued
I ask how leaders can use the Enneagram to manage individuals instead of assuming everyone is wired the same way
I learn the right way to implement the Enneagram at work, and why a one-time workshop is never enough
I explore how entrepreneurs can use the Enneagram to understand their own strengths, blind spots, and even serve clients better
🎧 Tune in or keep reading to walk away with practical insights you can apply immediately—for yourself or the people you lead.
🔗 Helpful Links
🌐 Connect with Ashton Whitmoyer-Ober:
Website: enneagramashton.com
Instagram: @enneagramashton
The Enneagram Advantage Program: enneagramashton.mykajabi.com/advantage
Free Self-Assessment: truity.com/test/enneagram-personality-test
Books: The Enneagram for Relationships, The Enneagram Made Simple, and A Little Bit of Enneagram — available on Amazon
🌐 Mindy’s website for business consulting: https://www.limerockcareerco.com
🎧 Listen to the podcast on Spotify, Apple Podcasts
Episode 50: Watch or Listen
Key Takeaways From Episode 50
The Enneagram at Work Is About Motivation, Not Just Behavior
What sets the Enneagram apart from tools like Gallup Strengths or DISC is that it's tracking why someone does something, not just what they do. Two people can both say they avoid conflict, but the reason behind that avoidance can come from completely different places depending on their type. Understanding that "why" is what actually helps you communicate and lead differently with different people, instead of assuming everyone processes feedback or handles stress the way you do.
Why Tests Alone Only Get You 60% of the Way There
Ashton was refreshingly honest that most Enneagram tests are only about 60% accurate, partly because we tend to answer based on how we want to be perceived, not necessarily how we actually are. Her recommendation: take a test that gives you a probability across multiple types (she mentioned the RHETI), narrow it to your top three, and then sit with the descriptions that make you a little uncomfortable, not just the ones that feel flattering. The real insight tends to live in the parts that sting a little.
What Happens When Teams Actually Use It
Two examples stuck with me. In one company, a leader learned how their specific Enneagram type was shaping their leadership style in ways that worked for them but not necessarily for their team, and both sides adjusted once they understood each other's wiring. In another, a company dealing with high turnover brought Ashton in to help the team understand each other, and six months later, they'd only lost one employee. That's a direct line from "people feel understood" to retention, which hits the bottom line in a way leadership can't ignore.
A One-Time Workshop Isn't Enough
Ashton was clear that the Enneagram at work only works if it becomes part of ongoing culture, not a single training day people forget by Friday. That means weaving it into team meetings, onboarding conversations, and how you think about hiring gaps (not by asking for a specific type, but by recognizing when a team is missing analytical, detail-oriented thinkers versus big-idea generators, for example). The companies that see real results are the ones that keep bringing it back up.
🎧 Listen to the full episode of The People Success Circle for more practical insights and leadership strategies you can start applying right away.
Read the full transcript
Mindy: Welcome back to this week's episode of the People Success Circle podcast. I am excited to have Ashton Whitmoyer-Ober here as my guest today, also known as Enneagram Ashton. Ashton is an expert in the Enneagram, both in personal life and at work. I've been in the world of human resources for a long time, and I like assessments because they really help us understand not only how we're wired, but how our teams are wired. So I couldn't miss the chance to have Ashton with us today. Welcome.
Ashton: Thank you so much for having me. I'm excited to be here.
Mindy: I want to start by having people understand how you became an expert in the Enneagram. When did you first start using it, and what did you do before?
Ashton: I created Enneagram Ashton back in 2019, right after I graduated with my master's degree in community psychology. I'm a community psychologist by trade, and throughout my program I learned about different personality systems, but I was totally captivated by the Enneagram because you can use it as a tool to understand yourself and others, and figure out why you do things the way you do them, not just who you are. It's not about who you are, it's about why you do the behaviors — so if there are behaviors you don't like about yourself, you can use this as a tool to change them.
Before jumping into the Enneagram and my business, I was working in domestic violence and sexual assault prevention, helping programs and centers across my state develop healthy relationship programming. I really saw those two worlds combining, where the Enneagram can be used as a tool for healthy relationships, understanding your spouse, partner, friends, family members, and in my more recent work, colleagues, leaders, and supervisors.
Mindy: I didn't know there was a master's in community psychology — that's so interesting. So tell me what your business looks like today.
Ashton: Today I spend a lot of time speaking, traveling, and doing corporate workshops and retreats. My degree is technically in community psychology and social change, so I love seeing change, seeing those light bulb moments when people realize they're doing things because of a specific motivation, and then start to understand the people around them a little better. I have a couple of programs too, but I spend most of my days speaking, which I consider one of the biggest honors of my life, that people want to hear what I have to say.
Mindy: As a speaker myself, I totally agree. I get off stage and think, I can't believe I get to do this. So how do you train people inside corporations to implement or learn about the Enneagram, and what type of team or organization actually needs something like this?
Ashton: Every team and organization needs something like this, because we get so caught up in the day-to-day, are we being productive, are we meeting our goals, that we miss the people. The Enneagram, or any good personality tool, is a way of putting in the effort to understand the people you work with. When you understand your colleagues better, you communicate better, you have less conflict, and you actually increase productivity, because people are happier. When people feel understood and heard, they work harder.
Mindy: I totally agree. As an HR leader, I'm always coaching leaders on setting goals, giving feedback, all of that — and knowing more about the person helps you lead and manage on an individual basis instead of assuming everyone is the same, or assuming that if someone isn't like you, they're the problem.
Ashton: Exactly, because we all learn differently, communicate differently, and receive feedback differently. The way I communicate as an Enneagram Two is going to be different from the way you do as a Three, or the way someone else does as an Eight. What an Eight cares about likely isn't what I care about. We go out into the workplace assuming everyone's like us, and then get frustrated when we think we're communicating effectively, but we're actually communicating the way we'd want to hear it. A tool like the Enneagram removes a lot of that unnecessary frustration.
Mindy: I'm certified in Gallup Strengths myself, and as an HR leader I feel like I've done almost every tool out there at some point. Gallup's research says we have an employee engagement problem, not just in the U.S. but globally, currently around 32% of employees are engaged at work. That's about one in three people.
Ashton: Right.
Mindy: But the flip side, which relates to both the Enneagram and Strengths, is that when a tool like this is actually implemented and people understand each other, that engagement rate jumps to around 77%. People are far more engaged when they feel understood, valued, and like they're not just a number, when they feel like people actually care about how they're wired.
Ashton: Yes, and that people want to learn about them.
Mindy: Right. There's so much to learn — I'm not an expert in the Enneagram at all, I'd consider myself a complete beginner, but I've taken the assessment and I know I'm a Three. Even with that little bit of knowledge, I'm learning what I'm like on a good day versus not, what I need to let go of, and what's actually fueling my success. So if a company decides this is a tool they want to implement at work, how does that actually work? Is there one specific Enneagram test, are there different versions, and how does an organization implement it?
Ashton: People love tests, they want someone else to tell them who they are instead of doing the work, myself included when I first found the Enneagram. But the issue is that tests are only about 60% accurate, because we answer questions in ways we want to be perceived, even if we swear we're not, and because we're often answering based on our behaviors, when the Enneagram is really about our motivations. For example, a test might ask if you avoid conflict or face it head on. Two different Enneagram types might both say "avoid," but for completely different underlying reasons, and the test will score them similarly anyway. That's a huge piece tests miss.
So I always suggest starting with a test, that's a great place to begin, but don't just take the result and run with it. I recommend tests that give you a probability across types, like the RHETI, the Riso-Hudson Enneagram Type Indicator. Take your top three results and dig into those to see what actually resonates. It's not always going to feel warm and comfortable, sometimes it's going to feel a little uncomfortable, and that's often where the real insight is.
Mindy: That's so true. I love how they describe it as "on a good day" versus "not on a good day," because we all have weeks where we're acting like the less flattering version of our type. How helpful is it for a leader to know an employee might just be having an off day, showing behaviors that aren't typical for them?
Ashton: Very beneficial.
Mindy: So when an organization wants to implement this, is that assessment where you'd have them start?
Ashton: Yes. If someone comes to me wanting to bring the Enneagram into their workplace, I ask what they're hoping to accomplish, better team morale, better communication, high turnover, whatever it is. The first step is always getting everyone to take an assessment, then sitting down together to go over the results. But the key, and we talked about this before we started recording, is that it can't be a one-time thing. It has to keep being part of the conversation, whether that's team meetings, hiring practices, or onboarding. I've seen people use it not to determine who to hire, but to gather more information during onboarding. There are so many ways to weave Enneagram language into workplace best practices.
Mindy: I say the same thing about Gallup Strengths — when people say they've taken the assessment, my question is always, how are you implementing that? Are people aware of it, does the team understand how they work together, how do you actually leverage it, not to rate or review someone based on a personality assessment, but to get the best results and the most satisfaction at work.
Ashton: Absolutely. The best workplaces I've worked with are the ones investing the time to continuously bring it up, whether that's me or someone else coming back quarterly, or just making sure it stays top of mind rather than going in one ear and out the other. Those companies become known as ones that care about their people.
Mindy: A hundred percent. And it often spills into personal life too — someone will go home and want their spouse to take the assessment, or their mom, their siblings. So do you usually work with a leader, or HR, and what are the actual integration steps you recommend?
Ashton: It varies. Sometimes HR contacts me, sometimes a team lead or a "people manager" at larger companies whose role is specifically about strengthening relationships among their people. It depends on how the organization is structured. For integration, it's important to get everyone on the same page first, some people come in with prior knowledge, others have never heard the word "Enneagram" before. So we start with what it is and why it matters at work, then move to the individual level, this is who you are, then how your type connects with everyone else's, and from there, next steps for how to keep integrating it into meetings, systems, and procedures going forward.
Mindy: That makes a lot of sense. When I start a project with a team, I like to figure out how we'll leverage who we are to contribute, not just our functional area like marketing or accounting, but what role each person can play based on their actual strengths.
Let's talk about your books, since you're also an author.
Ashton: I have three books on the Enneagram. The first is The Enneagram for Relationships, focused on four kinds of relationships: romantic, friendships, family, and the workplace. The second is The Enneagram Made Simple, a great starting point if you want to learn the foundations and all nine types. The last is A Little Bit of Enneagram, part of a Barnes & Noble series of small-format books, a great pocket reference to carry around or use to understand people a little better.
Mindy: I didn't know Barnes & Noble had that series, what an honor to be part of it. Can you share an example of when you've seen the Enneagram really click in a workplace, and the results that team got?
Ashton: I can always tell the difference in workplaces where people genuinely care about each other, the room feels different, people are warmer, more productive, having better conversations, versus cold, sterile environments. My favorite companies to work with are the ones I get to go back to, because that's when I really see the change. One company I worked with had a lot of confusion around a leader whose specific Enneagram type shaped how they led in a way that worked for them, but at a cost to their team. Once that leader understood how their team needed to be led based on type, and the team understood why their leader led the way they did, it became a real give-and-take, not about changing who you are, but figuring out how to work better together.
Another company was dealing with a lot of turnover, they couldn't understand why people would start working there and then leave, and they were hearing chatter about workplace expectations people didn't like. They brought me in to get everyone on the same page and understanding each other, and when I checked back in six months later, they'd only had one person leave in that time.
Mindy: That's huge, because retention really hits a company's bottom line. What are you working on right now with a current client?
Ashton: One company I'm working with right now realized their team was missing "Fives and Sixes," the more analytical types. They're full of doers and creatives with big ideas, but sometimes the data behind those ideas gets missed. So we're working on two things: when they hire, they're not literally screening for "a Five or a Six," but they're looking for people who are logical and analytical to fill that gap, and internally, figuring out how existing team members can step into that role a bit more themselves.
Mindy: I love that, because when I coach people on hiring, I always say assess what you need first, then build interview questions around it, so you don't have to say "I need a Five," you can ask, "tell me about a time you analyzed a problem, what steps did you take," and start to see if someone has those tendencies. I also have a lot of entrepreneurs who listen to this podcast. How would you recommend someone who owns a business use the Enneagram to understand how they work and what support they might need?
Ashton: It's great for outlining your strengths and your growth areas, and your type can tell you why certain things are challenging for you specifically. Every type has a core fear and a core desire, and understanding what fear might be driving you to procrastinate or avoid something is the first step to actually changing that behavior. Depending on the type of entrepreneur, a lot of service-based business owners, coaches especially, are also starting to use the Enneagram to better understand their clients. Anywhere there's a relational dynamic, the Enneagram is useful.
Mindy: That's amazing, I hadn't thought about that, but it makes total sense, since I use Strengths with my own clients for exactly that reason. For me personally, I'm an Enneagram Three, I start a lot of things and move really fast, I put a lot into what I do, and I know I need someone who balances that out and reins me in a bit. I have someone on my team who does exactly that, and it's the best complement to who I am, I'm the creative, fast-moving go-getter, and she's the one asking, "is this actually realistic," and building the real plan instead of just diving in.
For someone who's never heard the word "Enneagram" before, how would you describe it to them?
Ashton: I call it an ancient typing system. It's very old, and it places people into nine different types, or nine different lenses through which they view the world. Within each of the nine types, you have a core fear and a core desire. The Enneagram is different from tools like Strengths Finder, DISC, or Myers-Briggs because it's about motivation, the why behind what you do, not just the behavior itself. So two people can have the same behavior for entirely different underlying reasons, depending on their type. Each type also has genuinely great qualities and some more challenging ones.
Mindy: When you look at the nine types, is it a pretty even spread across the population, or do some types show up more than others in certain groups?
Ashton: It depends on the space you're in. When you told me you were a Three, I wasn't surprised, entrepreneurial-minded people tend to lean toward Three. I'd say Four is probably the most statistically unique, though their core desire is literally to be unique and set apart, so maybe that's part of why.
Mindy: That's interesting, maybe how they answer the questions ties into that too. If someone listening hasn't considered using the Enneagram at work, or doesn't even know their own type yet, where would you point them?
Ashton: I'd obviously point them to me first, my Instagram, Enneagram Ashton, has a lot of free resources. The Enneagram Institute is also a well-established resource, and there are plenty of good books out there, including mine. The important thing either way is not to just flip to your type and stop, it's worth learning about all nine and actually doing something with what you learn.
Mindy: Is there a self-assessment linked on your Instagram?
Ashton: Yes, I have a free self-assessment to help narrow down what type you might be.
Mindy: I'll make sure we link that, along with your books and website, in the show notes. I know you have a program coming up on using the Enneagram at work, tell us about that.
Ashton: It's called the Enneagram Advantage, and it teaches people the advantage of using the Enneagram in their work and workplace. I'm training people how to use it and start implementing it in their own workplace or with their clients, a few entrepreneurs who've gone through it are already using it with their own coaching clients. It's a seven-week live virtual program, and doors open September 2nd.
Mindy: I'll include that link too. I just cannot stress enough how important it is to understand your employees for who they are as people, it increases engagement and helps people feel genuinely positive about their working relationships. I see that difference with my own team and clients, and I can absolutely see it playing out the same way with the Enneagram. Thank you so much for coming today and sharing your insight. If you're listening, you can find everything you need in the show notes. Ashton, thank you for your time and for sharing your wisdom with us.
Ashton: Thank you for having me, it was great to be her
