Ep 013

Using the Enneagram to Lead with Compassion, Strengthen Your Team, & Scale Your Business


Ian Cron

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Inside This Episode

One of the biggest hurdles for financial advisors who want to build a thriving business, is the transition from a one-person operation to leading like a CEO. Up until that point, most advisors only have to worry about themselves.

But scaling a high performing team requires a completely different level of leadership and self-awareness.

And to better understand how to get to that level, Brad’s talking with Ian Cron, all about the Enneagram—a personality assessment tool that can help you understand how you and your team are uniquely wired.

Ian is a psychotherapist, Enneagram teacher and best-selling author whose book “The Road Back to You: An Enneagram Journey to Self-Discovery” has sold more than 1M copies.

If you want to grow your business, you can’t do it alone. You need people. And if you don’t understand how people think or their motivations for how they act, it will be a constant battle trying to scale.

Ian’s going to show you how to leverage the Enneagram to discover areas for growth, identify your blind spots, foster deeper relationships, and communicate more effectively, so you and your team can grow together.

3 of the biggest insights from Ian Cron

  • #1 How to use the Enneagram to build self-awareness, see the world through your team’s eyes, and lead with compassion and clarity.

  • #2 How to strengthen relationships, navigate tough conversations, reduce friction, and empower your team, by understanding the 9 Enneagram personality types.

  • #3 Breaking down the 9 Enneagrams types and high-level ways to manage and motivate each group.


  • 00:00 A high-level overview of the 9 Enneagram types and the unconscious motivation of each type.
  • 06:57 Which Enneagram test is the most reliable?
  • 10:13 Why do people often dislike their Enneagram results?
  • 12:32 The number one characteristic of leadership and success as determined by a study that looked at 72 high-performing CEOs.
  • 18:28 A real-life example of how the Enneagram test can help solve business challenges.
  • 21:44 How can advisors use the Enneagram test to help with their transition from a small team to a growing practice?
  • 27:58 How understanding the interplay between your business partner’s Enneagram and your Enneagram can decrease conflict and increase growth.
  • 36:22 How Enneagram results can be just as destructive as they can be constructive.
  • 40:07 Understanding the three triads of the Enneagram test — and how to apply that understanding to become the best leader for your team.
  • 53:30 How self-awareness affects likability.
  • 55:57 How does Ian describe, “Do Business. Do Life?”





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  • One of the greatest mistakes a leader or business leader can make is to presume that their way of seeing the world is normal.” – Ian Cron

  • The Enneagram is so accurate that when you use it in a poor fashion, it will cause you more problems than it solves.” – Ian Cron

  • “Our work has to have meaning and purpose in order for it to feel satisfying.” – Ian Cron

  • “When people have self-awareness, they are better leaders, better team people.” – Ian Cron

  • “If you’re looking for flattery, the Enneagram is not a great instrument for you because it’s going to reveal that which is best about you and also what’s worst about you.” – Ian Cron

Brad Johnson: Welcome back to another episode of Do Business Do Life. Really excited today. Ian Cron, welcome to the show.

Ian Cron: Thanks, Brad. It’s great to see you again.

Brad Johnson: You too. I feel like between you and Michael Hyatt, I mean, I feel like you guys are competing for regulars on the show, so it’s always fun when we get a chance to have another conversation.

Ian Cron: Well, I’m a big fan of Mike, so I’m glad to be counted in that company.

Brad Johnson: He’s good company to be in, that’s for sure. So, as I was preparing, like we’ve covered a lot of ground on Enneagram and I’m going to say based on the last show because you came on there and that was still to this day, it was my number one YouTube video by views from downloads. It was one of my most downloaded shows of all time. So, I’m going to say, like, you’re definitely partially responsible for taking the Enneagram mainstream inside of finance. And what’s been really cool is that conversation was probably almost five years ago now and maybe more. And what’s been awesome is how the Enneagram has impacted me as a husband, as a dad, now as a business owner and a founder, as we incorporate that inside of Triad. We use it in the hiring process. There’s not a day that goes by inside of Triad we don’t talk about someone’s Enneagram number. So, it’s really become part of our language and how we start to have empathy and see through other people’s eyes. And so, I just first off want to start this conversation by saying thank you. I don’t know where we’d be at today without the work that you did that Michael Hyatt introduced us back in the days of Blackberry. So, thanks for all the work you’ve done to educate people on Enneagram. And I’m really excited because I want to continue down the path of educating those advisors out there that might be able to benefit them.

Ian Cron: Well, hey, listen, music to my ears. I’m thrilled that it’s been helpful for all of you.

Brad Johnson: Well, you came in to Lawrence, Kansas, and met with our team and that’s we’re probably about ready for round two. So, with that being said, I don’t want to rehash the very first conversation we had. We kind of did a deep dive into each of the Enneagram, each of the nine different personality types. So, we’re not just rehashing the same conversation we had last time. I know we’re going to dive a little bit deeper but for those that didn’t catch the last conversation, if you kind of had to 30,000-foot view, here’s what the Enneagram is for those that are not familiar, maybe a brief description of each of the numbers, how would you explain it to those that are unfamiliar?

Ian Cron: So, the Enneagram is an ancient personality typing system that teaches there are nine basic personality styles in the world, one of which we gravitate toward and adopt in childhood as a way to cope, protect ourselves, and to navigate the new world of relationships in which we find ourselves. These nine types, each of them has an unconscious motivation that powerfully influences how that type habitually and predictably acts, thinks, and feels from moment to moment on a daily basis. So, let me do this. Let me run through all nine types. I give you a couple of descriptors and then I’m going to tell you what the unconscious motivation of that type is. How’s that?

Brad Johnson: That’s awesome.

Ian Cron: Okay, here we go. 1s are called the Improvers, ethical, meticulous, detail-oriented, analytical, and full of integrity. They’re motivated by a need to perfect themselves, others in the world. They also want to avoid fault and blame and making mistakes, God forbid. Number 2s are called the Helpers, warm, caring, giving, motivated by a need to be needed by others. They have a profound need to be liked, appreciated, and approved of and that motivates their behavior in very particular ways. 3s, the Performers, success-oriented, image-conscious, wired for productivity. They’re motivated by a need to succeed, to appear successful, and to avoid failure almost at any cost. 4s, the Romantics, sometimes called the individualists, creative, sensitive, moody, temperamental, wildly imaginative. They’re motivated by a need to be unique and special to compensate for what they perceive as a missing piece in their essential makeup. 5s are called the Investigators, analytical even more than once, by far the most analytical number on the Enneagram, detached, emotionally detached, and very private. They’re motivated by a need to gain knowledge, conserve energy, and to avoid relying too much on others. These are people who use knowledge as a way to fend off feelings of inadequacy or ineptitude.

6 is the Loyalists. We think they’re probably more of these people than any other type on the Enneagram. These folks are committed, they’re practical, they’re earthy, they’re witty, they’re worst-case scenario thinkers as well who are motivated by fear and the need for security, safety, certainty, and support. 7s, gosh, the Enthusiasts, fun, spontaneous, adventurous, always thinking about a future filled with unlimited possibilities. They’re motivated by a need to be happy, to plan stimulating experiences, and really to avoid emotional and psychological pain. 8s, the Challengers, commanding, intense, notoriously blunt, at times confrontational. They are motivated by a need to assert strength and power over others in the environment in order actually to mask vulnerability and weakness within themselves. And then finally, 9s, the Peacemakers, pleasant, laid back, accommodating. They’re motivated by a need to keep internal and external peace and really to avoid conflict, again, almost at all costs. So, that’s a fast rundown.

Brad Johnson: That was impressive. I asked you before we went live, I was like, “Can you kind of free flow on each of the numbers pretty quick?” Impressive. This is why you’re so good at what you do. I’ve only witnessed one other, just as a complete aside, I’ve only witnessed one other free flow like that ever on the podcast episodes I’ve done. DLynn Proctor once graded wine like that. If you ever get the chance to meet DLynn, he’s awesome but he literally freestyle-flowed it like that. That was, I’ll put you guys neck and neck. You just did it with the Enneagram, so.

Ian Cron: I’m glad.

Brad Johnson: So, thanks for doing that. Cool. All right. So, now at least you’ve got the CliffsNotes or as the kids say it these days, the SparkNotes version of the Enneagram, by the way, does not do it justice. So, don’t just take this little bite size but I wanted, Ian, to give just a little context on each of the numbers. One of the things we are going to do, I’m holding it up. This is actually a tool we use internally that’s an Executive Summary on each number. Actually, Ian was the one that introduced us to this. So, if you want to go a little more in-depth, this is going to be an offer that we give to listeners to the show, and then we’ll probably also link to the… You can explain it better than me, Ian, but there’s like these free Internet Enneagram tests and the people that I’ve talked to that take those are like, “One time I was a 2. Another time I was a 6. Another time I was a 7.” It’s kind of like you get what you pay for. The one that we use internally at Triad is like super detailed. If you want to give a better explanation but it’s pretty thorough and has an extensive report on the back end. What’s the difference between the free Internet version of Enneagram and the one that you recommend?

Ian Cron: Well, so as a therapist, we are exposed in graduate school to what’s called the psychometrics, the construction of things like a personality assessment. There are PhDs who do this work. It is very, very complicated to come up with a test that gives consistent results, right? And I mean, a bunch of putzes don’t sit around and come up with the SATs. You can trust me that there are committees of PhDs trying to make that thing what it is. The same is true of the Enneagram test. If you go into some kind of magazine, “Here’s ten questions. Figure out your Enneagram type,” you are up to a loss. The best test out there at the moment is what’s called the iEQ9. It’s a test that’s offered on my website. It’s the only one I really trust at the moment. The validity and the credibility rate is very, very high because the sample pool is high. I will not bore you with all the statistical research. Just trust me when I tell you it also has a 22- or a 44-page report so it’s very, very robust. And so, people would just go to my website, IanCron.com, and find out about the iEQ9 themselves.

Brad Johnson: Cool. Appreciate that. This is an aha. So, we use this inside on our team and Ryan on the team. So, we coach a lot because, obviously, we’re working with small businesses and when you bring new people together, obviously, there’s a forming stage. Then there’s actually a storming phase where they get to know each other a bit and work out their differences. Then it goes to norming, then it goes to performing. So, we’ve been coaching on this for a year. Ryan busts out this report from his Enneagram and he goes, “Did you realize on like page 17 it actually says where you go in storming phase when you’re in forms of mental health?” So, it actually directly matches some of the coaching we do. So, this is a very thorough report. It’s the reason I share that. It looks at many different angles, the wings, where you go in health, where you go in unhealth. And so, if you want to get really detailed on how this stuff works, highly recommend the one that Ian just shared there. Okay. So, let’s talk. This is something I’ve seen. As people get familiar with the Enneagram, I took a few notes. I love that you said an unconscious motivation because I was trying to explain and it’s almost like your natural wiring, the natural lens you see through but you said how you act, how you think, how you feel.

So, on that note, the feel part almost universally when someone hears their Enneagram number the first time, they have like almost like a visceral response like, “Ugh, that one. I don’t like that one. I’d rather be this one.” Can you tell? Like, why does that happen? Like, why is that a common response?

Ian Cron: Yeah. Well, it’s very uncomfortable to feel like someone’s been reading your mail, right? Like, the Enneagram is uncannily accurate, right? It gives you a, well, no, I guess what I would call it is that it gives you a low-definition picture of the inner architecture of human beings but it is a much greater level of definition than the one most people operate with all the time. And when you get that level of clarity about yourself, it can be very uncomfortable, right? Also, the Enneagram, if you’re looking for flattery, it’s not a great instrument for you because it’s going to reveal that which is best about you as also what’s worst about you. It’s what’s worst about you is what’s best about you. It doesn’t pull punches. It’s going to say, “Hey, these are your areas of growth. Here are your blind spots. This is the stuff you got to work on.” Everybody like StrengthsFinders for the obvious reasons.

Brad Johnson: Yeah. Feel-good test. Feels great.

Ian Cron: Yeah. It’s a feel-good, too. Yeah, I love it. And don’t misunderstand me. I love it. It’s great. It has a place. But one of the reasons I love the Enneagram is that it gives you a real 360 view. And I think that’s important for leaders. I mean, I think it’s important for everybody to realize, “Okay. What is it I don’t know that I don’t know?” That’s really important.

Brad Johnson: Yeah. Well, what you just made me realize in that little comment, one of the core values at Triad is check your ego at the door. The Enneagram is a check your ego at the door sort of self-assessment. That’s really what it is.

Ian Cron: Yes. Yes.

Brad Johnson: Yeah. Okay. So, I want to start to dive in. I think the easiest place to maybe start here. We focused, I think, on the last couple of conversations is really the internal focus and I want to hit one thing because you shared this out in Nashville when you spoke to our members and you said the number one principle, I think, or the number one characteristic of leadership and success was self-awareness, I believe. And I forget which study you quoted. It was Harvard or one of the Ivy League schools that had done an in-depth study on this. So, if we look internally like you said, it reveals something maybe you’re not always aware of, blind spots, can you expand on that, just how you’ve seen this self-awareness, maybe specifically through the Enneagram kind of open the blinders for different leaders or different businesses that you’ve dealt with?

Ian Cron: Oh, man, absolutely. The study, by the way, for anyone interested was a study done by Cornell University and in cooperation with Green Peak Partners. And what they wanted to determine was they looked at the lives of 72 high-performing CEOs of companies ranging in value from $50 million to $5 billion. They wanted to figure out what’s the number one characteristic that accounted for their success. And they thought it would be grit, determination, strategic planning, you know, education, IQ, whatever, right? And then the conclusion of the study really upended all the researchers’ predictions. And the key line from the conclusion of the study, the key predictor of success among leaders and executives, is self-awareness. Now, what does that mean? Self-awareness, I think, is the ability to monitor and self-regulate the way that you’re acting, thinking, and feeling in a given moment. It’s to be familiar with your operating system, how you tend to, how you show up for life, and how the way you show up for life affects other people so that in real time you can make choices about the ways that you’re acting, thinking, and feeling to have the best kinds of interactions that you can have with other human beings. Let’s face it. In business, what is the number one challenge people have to face? Relationships. I mean, business is a friend of mine who’s very successful said to me very recently, said, “Business is all about relationships.” And you know this as a guy who’s been working with lots and lots of people and supervising lots and lots of people.

How much time do you spend doing personality management? A lot, right? So, to have self-insight and then as importantly, insight into the inner workings of other people gives you an enormous advantage. Right? Once you have that, there’s all kinds of things you’ll have to happen. One is employee retention. You’ll have people who feel like they’re understood and valued. You’re going to have people who know how to handle conflict better. You’re going to have less communication problems inside the house. I could just go on and on and on. You’re going to have more of a culture of care and humor, as you know. I mean, the Enneagram is just a great inside vernacular that people can use with each other, right? Give you just one last thing on this and sorry about my passion but Ray Dalio, who I know that you know, the hedge fund manager, was it Black…? What is it? Oh, gosh, not Blackstone. Anyway. BlackRock.

Brad Johnson: Yeah, he wrote the book, Principles.

Ian Cron: Exactly. And he uses personality. He uses multiple personality assessments with all of his people. And he says, “The reason isn’t because it helps with hiring or placement or that stuff.” He says, “Because it gives them an instant vocabulary to talk with each other about who they are inside and how they move through the world.” And to him, that’s invaluable like that’s part of the secret sauce that leads to success of a team. And I think that’s true. I’ve seen it over and over again.

Brad Johnson: Yeah. I think and I may be butchering this, he calls it radical, either transparency or radical, basically communication, some form of that but it’s almost like, yeah, we’re going to tell you what you don’t want to hear here but it’s for your own good.

Ian Cron: Yeah, that’s right. Yeah. He calls it radical transparency. It is a very innovative little cookie the way that it’s used inside the house there. But anyway, he does believe in the use of assessments and personality, things like the Enneagram. And I think he’s onto something really real. Like, when people have self-awareness, they are better leaders, better team people. To the degree that they don’t have it, they blow guardrail to guardrail through organizations and people’s lives.

Brad Johnson: Yeah. I’m just going to tie this together because that study and your example with Ray Dalio, it works in every form of leadership. We had Jocko come out to our experience in Austin in January leading a SEAL team. He said a couple of things that really hit home with me that kind of just reinforce what you’re sharing here, Ian. He said, “There are no bad teams. There are only bad leaders”. And he talked about just the accountability of being aware of how you show up as a leader, how that then obviously comes down to the team but he actually shared he’s got a new product coming out. You’ll appreciate this. Maybe you’ll buy one and use it but he’s doing a mirror and at the bottom of the mirror all that says is, “Problem identified.” Don’t you love that? But that’s like self-awareness, right? That’s like self-awareness in a product.

Ian Cron: Yes.

Brad Johnson: And we’ve all been, I think, around people that have a lack of self-awareness. It’s painful.

Ian Cron: It’s painful and it’s awful. Yeah.

Brad Johnson: It’s like, who’s going to tell them? Who do you want to tell them? Should you tell them? But like everybody’s standing around and trying to help the individual.

Ian Cron: You know, it’s so funny because today I was on a call with a woman. It was a coaching call and she is in a startup and she has an investor. They’re doing super well but they’re in that very fragile period and they have an investor on the board that is just a bully, I mean, a cookie bully. And we were talking using the Enneagram to try and figure out, well, this is a person who has no self-awareness and they are creating all kinds of problems. And in a company, the little company that’s doing really well. After three years, they’re already at $25 million in sales. I mean, they’re doing great, right? This person is just killing it. Anyway, I just was able to say, “Look, we got an 8 on our hands. We have a very unhealthy 8 on our hands.” And right now, you’re trying to interact with this person on the basis of diplomacy. And that is only reinforcing this person’s distrust of you because they actually need you to come at them with the same energy that they are. You know, they’re looking for you to stand up for yourself and this is where the Enneagram comes in for, really, it just can save you a lot of time is knowing and figuring other people out and how to be with them in a way that moves balls down the field with the least amount of damage or problems and with the most amount of joy, really.

Brad Johnson: Yeah. To your point, I’ve taken I won’t say every self-assessment. I’ve taken Kolbe. I’ve taken StrengthsFinder. I’ve taken DISC. I’ve taken Myers Briggs.

Ian Cron: Hogan, probably.

Brad Johnson: Yeah, I’ve taken a pretty good spill of what I’d say the most well-known personal development or assessment stuff. I’ll tell you, every single individual that takes the Enneagram because we’ve had every Triad team member, we’re up to close to 60 now and our community, when you came out, we had everybody take it. What was cool? We had husbands and wives next to each other and this is almost instant. You said, “Read my mail, reading my diary,” whatever it is. Like, that’s how I felt the first time I read your book, The Road Back to You, and it was like I took the test. And then I went straight to the Enneagram 7 section because, as Michael Hyatt says, it was about my favorite topic, you know, me. All of us, our favorite topic. So, I went straight to my section and I was like, “Oh my gosh, this is ridiculous.” But what’s interesting, that has been a very common response to every, say, 1 all the way to 9, all the way in between, everybody is like, “Wow, this is like crazy, scary, accurate like how it just expressed how I kind of show up or how I see the world.” And so, I want to go to now, once we start to understand the concept of the number, what are some ways because we focused a lot internally, kind of self-awareness. I wanted to hit that real quick but I now want to extend that externally. One of the things that I think is the biggest hurdle for a lot of advisors that start to have a level of success is they have to transition from financial advisor, me, it’s all on my shoulders to business owner/CEO.

Now, I have to grow and empower a team, very different skill set that takes people skills and self-awareness. And that for some is a pretty rough transition. It’s a new learned skills that they just haven’t used up to that point. So, if you were going to give this hypothetical financial advisor that wants to now become business owner, grow a small team, maybe 5, 10, 15, what would be some ways that you start to look through the Enneagram lens to assist that journey?

Ian Cron: Yeah. Well, let me just give one piece of advice that’s just in general. And that is when an organization grows, anxiety mounts, and as environments get more and more difficult, let’s say the market environments get more and more difficult, anxiety grows. And the tendency in those situations is to micromanage. Like, your first tendency is going to be, “I have to get down in the weeds because…” It’s sort of a panic response, right? And hopefully, if you have the right team in place, I always encourage leaders to resist that temptation. Got the right team in place. If you’ve got a COO or whatever is in place, just try not to go back to the same level of micromanagement that you’re used to in those moments. Try to stay up top on the thing because it’s the same principle on a boat. In a storm, you don’t want someone not in the helm, right? You know what I mean? Like, someone’s got to be high enough up while the rest of the ship is doing their job and not to get down into the weeds and start rowing and doing the knots. I mean, that’s something I’ve seen a problem that happens over and over again to people. I don’t know how your organizations are structured, but that’s certainly true in corporate settings with over large organizations where someone’s in that role. I would say that as that transition gets made, this is where self-awareness really is terrifically helpful. It’s the ability to self-observe, right?

Like, a lot of people just go through the day not observing themselves at all. They’re just like on autopilot, running on the same old patterns that either worked or didn’t work not for a long time. This is a tricky transition, I think, for certain types. We were talking earlier. We think that in your industry you’re going to meet a lot of 3s, Performers, you’re going to be a lot of 7s, the Enthusiasts, and you’re going to meet a lot of 8s, the Challengers. Now, this is not going to be as hard for 3s, right? 3s actually make very good CEOs. They have some risk aversion. So, they don’t upset everybody in the ecosystem too much with new ideas that scare everybody and they’re pretty good at managing people. For example, Hyatt, Mike is a 3, strong 3, and he’s fantastic in these sorts of situations. The other is 8s. 8s have to be careful about being autocrats that they can be, you know, they have to be very observing about rolling and bowling through people’s lives, being impulsive decision makers. That can work early in the face of an organization but when it gets bigger and requires management, it doesn’t work. There are studies that those types of leaders, challenger-type leaders work very well in the short term but if you maintain it over the long haul, it goes like that, right? The benefit is only good for a very set period of time. Interestingly, very self-aware leaders have this ability but the guy bullies in or the woman that bullies in is going to go, they’re going to tank after a – it’s going to be a very short-lived win.

7s, oh, boy. It can be problematic for some of them because they’re not necessarily typically, they’re not… It’s hard for 7s to be managers. In some ways, they are amazing entrepreneurs and those first three to five years, you cannot beat them. No one can get on a whiteboard and make more stuff happen. They’re charismatic. They are energized. They’re the first person you want to see when you walk in the office in the morning. They are just inspiring. They are so optimistic and they believe that anything is possible and everyone is willing to follow them. Amazing leaders, right? In my experience, particularly in those first three to five years of an organization’s lifecycle, the moment it starts to head into management, sometimes 7s need a little help alongside of them to continue to do stuff. Because the problem for some 7s is that there’s routine. If it starts to turn into routine, that’s a big problem, right? If they start to feel stuck, that’s a problem. If they get bored, that’s a problem. They have to just, you know.

Brad Johnson: Okay. Guilty.

Ian Cron: I know. And so, there are ways to work with this but the self-awareness you need as you make these transitions is super important. To always ask the question in the hallway between two open doors, what does this mean for me now? Who will I have to be in this moment to meet the requirements of leadership? Because it’s a different moment. And not to assume that what worked in that stage 1 is going to work in stage 2. It probably won’t.

Brad Johnson: Yeah. I’m going to get pretty transparent and honest here, which by the way, that’s what podcast is for is have real conversations. So, Shawn, my business partner, is a 3. I’m a 7. And for those of you listening in, first off, I know in finance, many of you have partners like we work with husband-wife teams. We work which sometimes one is kind of the advisor. One is kind of the op side. That’s pretty common. We work with a lot of partnerships for both our financial advisors. We’ve got partners up to three or four. And so, obviously, there are more variables, the more people. But here’s a real-life example, and I’ll just kind of play out and, Ian, feel free to add color commentary to this. I would say I’m pretty entrenched in a 7 and Shawn is pretty entrenched at 3. I think most people, if you would read it, you’re like, “That’s Shawn, 3. That’s Brad, 7.” It’s not like, “Ah, he’s kind of teetering between a couple there.” And here’s what’s really interesting, a real-life case study of what the Enneagram has done for business partners. So, I’ve known Shawn since college. We grew up in the business together. Our previous life, he was employee 9. I was employee 12. We literally worked side by side for almost 15 years. Same role. He’s building his book of business with advisors. I’m building my book of business. So, we’re doing like side-by-side things. I’m observing how he does it. We’re learning from each other, all of that.

And then you partner up in business and everything changes, right? And what I will say is the stress of partnership, the early days, lack of cash flow, the lack of having a partner before, it’s kind of like marriage. You do things as a single person, then you get married and somebody else has a different opinion on things. And I will say, had it not been for the Enneagram, there were some really, really tough conversations as we grew as partners, as we learn to work side-by-side and complement each other. As one of my friends says, “Don’t forget, your differences are a strength. Although it does not always feel that way in the moment.” But I’ll tell you what helped me. Here, that book I looked at pet peeves, and there’s a pet peeves section here. And I noticed when we would kind of get gridlocked in a big decision or, hey, a tug of war, I think it should be this way, he thinks it should be that way, oftentimes, a lot of my communication, I’ll just throw a few at you for 3. So, Enneagram 3 is about execution, right? They run up a to-do list. I think I’ve heard you share it, Ian, “Inefficiently run meetings when people block the path to their goal. People who don’t deliver on what they say they’re going to do. People who move too slowly when people waste their time.” So, these are just a handful of pet peeves that I just rattled off there but what I realized is how he processed and how I process information was different.

And without knowing that, it created frustration. With knowing it, it created awareness that actually helped us run the business better, where we kind of checked each other strengths and weaknesses. Anyway, I just want to share that because I know a lot of the advisors out there, like they’ve got great partnerships, but every partnership comes with its own struggles and communication and all of that. And I just found the Enneagram was incredibly important to help us grow together, to lead a company. And so, I don’t know, maybe you can dissect what I just shared or maybe use some other examples, but I’ll be seeing that play out in other partnerships or people that have to work together like really closely in business.

Ian Cron: Well, you’ve just articulated a principle that I operate with, which is one of the greatest mistakes a leader or business leader can make is to presume that their way of seeing the world is normal. Because if you do, when you meet someone who sees the world and processes the world differently than you do, you will feel justified in judging them abnormal, right? You’re going to be like, “That’s not normal.” Now, you’re assuming that your way is. Both the Enneagram is right, and I believe it is. There are nine normals, and if you don’t learn the normal of the person you’re working with, you’re missing out on the opportunity to take advantage of the way they see the world, the way they process life, the way that they make decisions, etcetera, etcetera, right? Let me give you an example of one. I’ve worked with a company in Atlanta, and I loved these two guys. The guy who was a founder is a 7. He is a classic 7 and he built a business that is big and it’s interesting. It’s a fascinating business that he has. And they in a very short period of time, absolutely crushing it. His COO, who also is his best friend, is a strong 6. Now, the 6 is the loyalist. Sometimes they’re called the devil’s advocate, as I mentioned earlier, for your folks, just by way of a reminder. These are people who are worst-case scenario thinkers.

Now, listen, Brad, when you tend to process anxiety with optimism, a 6 is going to deal with fear through manage it with pessimism. All right. Now, those two could be at loggerheads with each other, but let me tell you, they have the best dance in the world. Those two love each other and they laugh with each other about and here’s where the genius of it is. The two of them recognize they know each other’s types. They know each other’s blind spots. They have a sense of humor about it, and they can correct the excesses of the other. So, when the 6 becomes excessively pessimistic, the 7 can go, “Ah, now wait,” and then vice versa. That 6 can tap the brakes on an overly enthusiastic 7 who might be moving too quickly in a direction that requires more prudence and deliberation. And so, what you’re describing with Shawn is just the same thing I’ve seen over and over and over again in great corporate leadership is that when you have people on board who have self-awareness and they understand each other, then they can come to the table with complimentary gifts that, at the end of the day, only serve the best interests of clients and workers, right? And so, I’m thrilled whenever I hear people describe scenarios like you just did because it’s what you want.

Brad Johnson: Yeah. Well, so what’s funny, you just gave a 7, me, 6 example. My wife, Sarah, is a 6. And so, I shared this with you. So, when Michael Hyatt so, I mean, I look back, I’m like, “Wow. This is an incredible place to learn about the Enneagram. He took us all out to Blackberry and it was kind of like a marriage retreat. He brought you in as a guest. We spent a full day and then one day, one 24-hour period, I felt like I knew my wife better than I had and we’d probably been married a little over a decade at that point. But like, just to your point, to reinforce how this not only works in business but also family. All of these frustrations, Sarah calls it realism, by the way, instead of pessimism.

Ian Cron: Oh, I know. I know. I’ve heard that a million times.

Brad Johnson: But anyway, it is a good balance. I think we’re like the same coin, opposite sides, and we balance each other out. And sometimes I say, “Hey, the sky is not falling if this happens,” and sometimes she has to say, “Hey, it won’t always just all be good.” And I’ll say it just like it’s really cool because it’s given me awareness of one of her strengths that now doesn’t have to be conflict. It can actually bring us closer together to balance each other, joke about it, all of that. I want to say one other thing because you said something early on. You said the Enneagram is not about numbers shaming. Like, everybody has a little bit of every number in them and we talk about like in places of health and in place of unhealth. But what advice would you give so this doesn’t become like weaponized inside of a business? Because I think obviously that could happen if you let it.

Ian Cron: Yeah. I mean, as you know, part of my day-long workshop on the Enneagram in corporate settings involves a whole thing on Enneagram ethics. But one of the ones that I’ve always highlighted for people is you can never use the Enneagram as a tool or a weapon to shame or insult people. And I’ve seen this over and over again. The Enneagram is so, as I mentioned earlier, accurate that when you use it in a poor fashion, it will cause you more problems than it solves. And one of those ways is and I’ve seen it, “Oh, you know, Brad, gosh, you’re being such a 7. Stop it.” Or, “Oh, my gosh. Laugh, laugh, laugh. You’re such a 3.” And I’m like, “Please don’t.” Like the Enneagram, the purpose of this is a powerful instrument. Don’t use it for any other purpose except to help people advance on the journey toward becoming the highest and best expression of who they are and that they can become their, I don’t like to use the word best-self anymore, that phrase, but you get the idea, right? It’s like for them to become what they were meant to be and succeed in the way they were meant to succeed. And so, yes, you definitely want to be careful of ever using it as a way to dismiss somebody.

Brad Johnson: Yeah. I’ll tell you one thing that happened organically. And by the way, this is where back to the test and you said all that I forget what you said, psychotherapies, like all of the metrics they track. So, we took this test after we probably had 20, 25 team members that had already been hired. What is like eerie is how the numbers sorted out based on the positions they were in inside of Triad. So, Enneagram 2 is the helper. Both Shawn and I’s executive assistants were Enneagram 2s, a very much like servant-leadership sort of role. And as a reminder, in Enneagram like the way I kind of phrase it is it recharges their battery when they help others. Would you say that the decent way of just like high level?

Ian Cron: Sure. Sure.

Brad Johnson: So, an EA would do that all day. That’s like a very support role, right? Our director of culture was a 2, but a ton of these different what I would call servant-hearted leadership people, Enneagram 2s, and they’re literally in that role inside of our firm. Back to your 3s, 8s, 7s, Shawn’s a 3. Mik, our other coach is a 3. Ryan’s an 8. I’m a 7. Jordan, a 3. Collin, that’s on the sale side, 7. So it’s like crazy, like 3s, 7s, 8s all in like sales kind of front-facing advisor roles. Enneagram 1s, new business, like high attention to detail. I’m looking here at my notes. We mentioned 5s earlier. Super analytical. We have a CFA. He’s an Enneagram 5, so a very technical role. The head of our portfolio management, Enneagram 5. So, like once again, like you can’t make this stuff up. It tells me there’s a lot of truth in this test but let’s go back to the 3, 7, 8. So, if I’m an advisor/founder in the 3, 7, 8 role and I’m looking to my team that is probably comprised of 1s, 2s, 5s, 9s from kind of at least our cross-section of our teams we work with, what do they need to start to think about? And I know I’m like throwing a lot of variables at you but maybe you want to break that down by number or I’m just curious, like if I’m looking through that lens as an advisor, how do I start to make sure I’m leading, empowering, having empathy for my team?

Ian Cron: Number one is you have to become a student of your team members’ numbers. And you’ve got a great little document there, that booklet that we’ve provided for you there, the Executive Summary. So, get your team to take a test or read a book together or have me come in and do a daylong or a day-and-a-half long with your team. And so, we got to identify types first then that becomes students of other people’s types in addition to their own. If you want to know how to manage somebody, you better find, you know, you can’t just – it’s not enough to know your own type and that’s it. That is not going to be very helpful ultimately. And you’re talking about 1s, 2s, 5s, and 9s. It’s hard for me to do this entirely because 3s, 7s, and 8s are all going to have a different set of challenges with 1s, 2s, 5s, and 9s.

Brad Johnson: Well, here, let me.

Ian Cron: But I can answer.

Brad Johnson: Okay. Yeah.

Ian Cron: Well, I can give you a couple of answers. Whether you’re a 3, 7, or 8, first of all, let’s just talk about that threesome first. There are three triads in here, right? One is 3, 7, and 8. Another one is 1, 2, and 6. And the other one is 4, 5, and 9. So, I’m going to give you a very fast on this. They’re called stances. 3s, 7s, and 8s are in what’s called the assertive stance. That means that when you see something that you want or that you need, you will go and ask for it or take it. You don’t sit back. It’s like you’re a go-getter. Okay. Let’s think of it that way. Okay. Your 4, 5s, and 9s are withdrawing types. So, when they need something or want something, they tend to move inward or away from people to find the resources to meet those needs. If you’re a 1, 2, or 6, you’re going to move what we call you’re going to move toward people to get those needs met, right? You are aggressive types. That doesn’t mean bad aggressive but it just means you’re very proactive, assertive, often very socially confident. You know, you’re going to go get it. Other types are not that way. So, first of all, a little bit of self-awareness, realizing, “Oh, I’m moving, how should we say, moving against.” So, you have to keep that in mind that the other numbers that I’m about to talk about are not numbers that are assertive. 1, 2, 5, and 9, not assertive types. You are. So, you have to manage your energy with those people lest you become overwhelming to them with all that moving against energy.

What 3s, 7s, and 8s need to just remember about 1s is they don’t cut corners. And sometimes in business, it’s like, “I don’t care, I don’t need the details. Just do that.” You know what I mean? That’s going to drive a 1 crazy. Like, a 1 is going to be like, “There are protocols. There are guidelines that things have to be done like this. Things have to be done like that. I don’t like it when things are unpredictable or when you change things midstream. I don’t like it when you improvise in the moment about how something’s going to get done.”

Brad Johnson: Which, by the way, 3s, 7s, and 8s tend to gravitate towards.

Ian Cron: Yes, especially, 7s and 8s. 3s could be a little bit more measured than a 7 and an 8 but yeah. You know, with 2s…

Brad Johnson: Real-life example before we get off the 1 and I’m looking at the pet peeves. You said it. So, kind of like to your point on being put on the spot, I remember we had a 1 on our team and it’s like a live presentation and we’re like, “Hey, can you pop up real quick and just throw 5 minutes up and just kind of talk about this thing?” That’s like the number one of the top pet peeves for 1 is kind of being put on the spot without preparation because we had a couple of 1s and I ask them, I’m like, “How would you prepare for that?” They’re like, “I would have a bulleted outline and then I would run through that bulleted outline about five times practicing it, and then I would probably practice it about five more times and then I would feel like I’m ready and prepared.” And when you take somebody wired that way and like, “Hey, we’ve got 5 minutes for you. You want to just hop up and, like, wing it?” that will create frustration and friction, right? So, we experience that internally, like real life when we ask a 1 to do that. And once we understood how a 1 operates, we don’t do that anymore.

Ian Cron: Yes. And so, you’ve just saved a lot of heartache and time. You may have just held on to an employee that you might have lost because you didn’t understand who they were inside. Because if you have repeated violations like that, after a while, they’re going to think, “Crappy boss. Doesn’t understand me, doesn’t understand the way I see the world.” Now, by the way, there’s another number that even hates that more and that’s a 5. 5s, oh, golly, that would be an absolute nightmare. They have a thing called preview and review. They want to preview everything and then later they want to sit back and review what happened but they need time to prepare. They do not like especially, I think, even more than once, they hate it. It freaks them out. On the other hand, I could get you to do it in a heartbeat as a 7.

Brad Johnson: It would actually be painful to me. I mean, it depends on the topic, obviously. I don’t like to just go up and wing it in anything but as long as I’ve got like three to five bullet points and I feel like I’m fairly educated on the topic, cool. Let’s go. Let’s have a conversation. Yeah.

Ian Cron: Yeah. But understand something, your type tends to be socially very confident, number one. Number two, you tend to be very good upfront. You’re charming, you’re persuasive, and all of that can be put to really good use, right? People are deeply affected by your enthusiasm and also typically 7s are very they’re quick-witted but they’re also quick with words. They can put stuff together on the spot very, very quickly. There are other types that just doesn’t work. They have other gifts but that’s not one of them. So, with 2s, you know, this is sort of easy. You actually did mention something so interesting about 2s. They are, we call it, the power behind the throne. They are excellent at being powers behind the throne. They know that actually, generals don’t win wars. Sergeants do. And so, 2s are really great. Like, for example, if they’re a little concerned about their relationship with you, they’re going to go to the 2 and say, “Hey, you know,” and then the 2 is going to be able to say, “Don’t worry about it. I’ll talk to Brad.” And then he or she’s going to go to you and say, “You know, I was talking to Jim today and Jim is kind of feeling X,” and they know how to deliver the news to you in a way that doesn’t put your nose out of joint.

Brad Johnson: So, a real-life story on a 2. So, Kenzie, our Director of Culture is a 2 and he’s like all-in on a 2. And so, we were talking to Enneagram. She loves the Enneagram. I mean, she helps like bring this into Triad, into our culture. And I go, “Kenzie,” I go, “You kind of deep down think like you can make everybody like you no matter what”. And she, like, laughs and she’s like, “Yeah, I think so.” And what was funny, I witnessed this. So, there’s an individual in our building. Let’s just say they’re like maybe a little grumpy most days when you pass them in the hallway. The next thing I see, Kenzie just like they’re chatting, she’s smiling, and I’m like, “Oh, my gosh, Kenzie, you won her over.” And she’s like, “It just took me a week or two.”

Ian Cron: And that’s a long time. That’s a long time for a 2.

Brad Johnson: Yeah.

Ian Cron: When it comes to 2 jobs and 3 jobs, actually, the 3 jobs I’ve seen them shine and I can call it almost every time. One is like EAs, right, tremendous. Another one, customer service. You can’t beat them. These are the Helpers, by the way, for people who have forgotten what the 2 is. The third one is H.R. They are geniuses in H.R. And then event planning and execution. Those just off the top of my head I just know. If you got 2 in one of those jobs, chances are they’re killing it. But just remember, when you’re working with them, it’s a 3, 7, or 8. This is important. You guys, all of us need encouragement. All of us need to be told that our contribution is valuable, but, man, you cannot tell a 2 enough that they are valuable to the organization, that they are invaluable, that they are loved, that they are appreciated. You’re managing that type, for example, and we’ve talked about this sort of stuff but if an 8 is doing a 360 end-of-year review on a 2, if they treat that 2 like another 8, that 2 will be a grease stain on the floor by the end of that hour. Again, to have self-awareness and to know, “Oh, this is a 2. I got to sort of approach this differently than I would if I was talking to someone of my own type.” You’re going to save a lot of heartache. We talked about 5s. They’re private. They have lower energy than a 3, 7, or 8 any day of the week. And you all just need to manage your energy at them because you all would drain them faster than any other number in some ways. And they have limited resources, real or perceived. That’s how it is. And they typically are introverts. Not always, but I’ve met very few that weren’t, didn’t have a very strong introvert side. And you all tend to be extroverts or ambiverts, one or the other but lots of extroverts in the 3, 7, 8 category.

And then 9s, I think the thing that 3s, 7s, and 8s have to do when they’re working with 9s is not allow them to merge with the viewpoints of the group or the organization, but to constantly be asking them. “I want to know what you think. I don’t want you necessarily to agree with what the group thinks. I want you to tell me what you think because I believe your presence matters. I don’t want you to duck by merging into what everyone else says, by saying, ‘Yeah, I’m on board with what everyone’s here.’” Because when you really push a 9, sometimes they have brilliant insights that if you can just get them to assert themselves will be a real help to the organization.

Brad Johnson: Yeah, You made me think. One of my favorite guys, Keith, he’s a 9. We have a partnership there. There’s three partners. One partner is a 1, Derek. Another partner’s a 7, Matt. And Keith is the 9. And he’s like, “I’m the glue.” Like, I’m the glue because he’s like the peacekeeper because like a 1 and a 7, they process things very differently. And it’s really cool to see how that partnership really thrives with the three of them kind of coming together to make a better outcome. But that’s a real-life example of how I’ve seen a 9 play out in a three-person partnership.

Ian Cron: Yeah. Well, and the other great thing about them is, yeah, they’re also called the mediators, which is what you’re describing. And what’s so beautiful about them is they bring this calm presence to every situation, and they have this unusual superpower of being able to see the world through the lens of every other type. So, they actually do sort of intuitively know how that 1 sees the world, how that 7 sees the world, how to bring them to a middle of the table and to work well together, and also to make both parties, the 1 and the 7, feel understood. So, they really do bring such a wonderful dynamic to partnerships, and also because I’ll finish with this in 9, they are consensus builders. So, they have a way of getting everybody on board and moving in the same direction.

Brad Johnson: Yeah. I think of just a few 9s and it’s like 100%. I won’t say any number’s the most liked on the Enneagram but I feel like every number loves a 9 just because they have a way of just I feel like 9s are great listeners too from my experience like in back to speaking consensus they take like the input so to get that.

Ian Cron: So, let’s remind your folks of this that I think every number is beautiful, likable, whatever, to the degree that they’re self-aware. In other words, that they’re doing the work, they’re learning about themselves, they’re learning about other people. They’re doing all the things that we’re talking about. The more a number lacks self-awareness, the easier it is to dislike them. I promise you, they will give you plenty of reasons not to like them to the degree that they lack self-awareness.

Brad Johnson: And that’s like just humanity in general. It’s like unaware people, I’m not seeking them out to go hang out with them, that’s for sure.

Ian Cron: No, no, no, no, no. To me, that’s the greatest gift of the Enneagram is this whole piece of self-awareness.

Brad Johnson: Well, my man, I know we’re right at the end. I failed to mention this at the beginning, so maybe we’ll put it on the intro. But by the way, you’re an incredible author, too. The Road Back to You was the first book that I read of yours, which was kind of my introduction to the Enneagram. So, if you’re out there listening to this and you’re like, “This was cool. I want to go deeper,” definitely go get Ian’s book, The Road Back to You. And then you wrote kind of a second piece of that, The Story of You. What’s the difference between those two books? I know they both discuss the Enneagram, but how would you say it?

Ian Cron: Well, yeah, The Story of You is a great sort of different take on the Enneagram. It’s actually a great follow-up to the Road Back to You once a person knows their number and stuff like that but the Story of You helps us understand that each of our types, each of our personalities is built around a story that we tell ourselves about who we are and how we think the world works. It’s also a story we tell others about who we are and how we think the world works, right? And it’s really important for us in life as we grow into adulthood to make sure that the story we tell ourselves and others is accurate and it’s the one we want to tell in adulthood. Because if we just drag the old story from childhood into adulthood and continue to live by its constraints and dictates, oh, it’s not good. And the Enneagram helps us identify that child story and gives us tools to adopt a new and better story for ourselves.

Brad Johnson: Awesome. Who doesn’t want that?

Ian Cron: No, everybody.

Brad Johnson: Well, okay, so as we wrap here, I’m just going to close with one last question. Ian, first off, you’ve been out to our experiences. We call them experiences, not events. We don’t like events. Those are a dime-a-dozen experiences. These are life-changing. And so, you were kind enough to spend some time with us in Nashville at our very first launch event. Community loved it. You did this live workshop and then you’ve come in to Triad as well and met with our team. And if you’ll allow us to have you back, we’re probably due for another round of that because the teams more, I think, almost tripled since the last time you were here. So, this stuff works. I just want to say like for those of you that have listened to podcasts, I don’t just like throw endorsements around, like Ian’s work and the Enneagram stuff he does, it’s life-changing and I don’t say that as a cliche. It’s real. So, thanks for all the work you’ve done with us, Ian, and you know we are about do business do life. That is our mission here. How do we help people grow freedom in their business and grow the business, but also create freedom in life and obviously live that on their terms and live it with joy. So, if I get Ian Cron’s definition of do business to life, how would you describe that, Ian?

Ian Cron: Well, those are very complicated questions, man. That’s a little overwhelming to me to come up on the top of my head. You know, the first thing that comes to me is, you know, I think that our work has to have meaning and purpose in order for it to feel satisfying. It’s not enough to say, “I’m going to work to make some money.” You know what I mean? Or, “I’m going to go to work so I can afford to play golf and go to wherever for on vacation.” These are not very satisfying things over the long haul. So, for me, doing business means making a contribution to a better world to be able to bring resources to bear on things that we care deeply about, right? Business is a means towards something, but it’s not an ends. It’s a means toward other things. And when we see it as an end, I think it becomes a little, it actually can be very toxic. And we’ve seen that people have surrendered their whole lives of doing business and saw it as an ends versus a means towards something great outside of the corporate sphere.

And doing life, I mean, look, for me, doing life has meant working to, with all honesty and care and with great energy, to become a man and for others listening, a woman, that is, and I use this phrase again, living out who they are in the highest expression of themselves. And that means looking at character. It means looking at having to repair things from the past that need repairing. It means having self-awareness. So, for me, doing life is so intentional. And, look, it requires that you burn calories, man. You got to do some work to make life what life can be. And so, that’s about as good as I can give you. If I’d had, if you’d given me a couple of hours, I’d have come up with something incredible but that’s about as good as I can get off the top of my head.

Brad Johnson: Hey, I think that was well said, and especially for being off the cuff, well-put. So, I appreciate your version of doing business, doing life. And, Ian, as always, it’s been a pleasure. Thanks for all the value that you brought to whatever advisors or whoever else is out there listening to this. Once again, thank you and I look forward to the next time our paths cross in person.

Ian Cron: Yeah. Brad, I thoroughly enjoyed it. Thanks.

Brad Johnson: All right. We’ll see you, Ian.

Ian Cron: Cheers.


Compliance Disclosure: These conversations are intended to provide financial advisors with ideas, strategies, concepts and tools that could be incorporated into the advisory practice, advisors are responsible for ensuring implementation of anything discussed is in accordance with any and all regulatory and compliance responsibilities and obligations.

Copyright ©️ 2023 Triad Partners. All rights reserved.



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