Josh Elledge is CEO of Up My Image and host of the Thoughtful Entrepreneur podcast. Josh is an Enneagram Type 7 leader and his enthusiasm and excitement shine through in this conversation.  I am so impressed with Josh’s journey of self-awareness that allows him to surround himself with teammates who complement his style. He has done the work to understand at which activities he excels and which activities he needs to delegate and has built a team that ensures all aspects of his business are well served.

Josh is founder of UpMyInfluence.com and Chief Executive Angel at SavingsAngel.com.

Check out all Josh’s podcasts:

The SavingsAngel Show

Authority Confidential

Thoughtful Entrepreneur

#Team #Leader #Leadership #Enneagram #Entrepreneurship  #Podcast #EmotionalIntelligence #EQ

[Video Transcript]

Matt Schlegel:

Thanks for joining me in conversations with leaders who are using the Enneagram as a leadership tool, and a tool for personal growth and development. Today, I’m speaking with Josh Elledge, host of the Thoughtful Entrepreneur Podcast and founder of UpMyInfluence. Josh is a Type 7 leader, and he shares how the Enneagram is helping him and his team grow his business. And now for the conversation.

Matt Schlegel:

I’m excited to be speaking with Josh Elledge, host of The Thoughtful Entrepreneur podcast and founder of his firm UpMyInfluence, where he applies a novel approach to solving the problem of B2B sales, providing an endless stream of high ticket qualified customers using the go-giver approach to building relationships. During our recent conversation on his podcast, I discovered that he uses the Enneagram as a leadership tool at his firm. So, I’m grateful that he can share his experiences with us here today in his using the Enneagram. Thank you so much for joining me, Josh.

Josh Elledge:

Matt, thank you so much for having me.

Matt Schlegel:

Great. Well, we were having such a great conversation and when you said, “Oh yeah, I’m an Enneagram Type 7 and I use Enneagram all the time”, I was just delighted about that. We had a great conversation on your podcast. So, let’s just jump in here and I’d love to know how and when you discovered the Enneagram.

Josh Elledge:

Yeah, gosh, I had a client who was pretty proficient, talked about it quite a bit. I made some guesses about who I am and he said, “Oh no, now you do not filter the world the same way that I do”, because that was his and he said, “You, my friend, I’m just going to guess you strike me as a seven, but go ahead and take a…” he recommended a test. Went through it, sure enough, I’m a seven, I’m married to a six. My director of operations is, and you’ll have to forgive me here you have to let me know, very perfectionist, what’s that?

Matt Schlegel:

Type One. Type Ones frequently work together and work very well together. So that’s awesome.

Josh Elledge:

We are a great combo. My Six wife and I… I feel like she loves what I bring to the relationship. I love what she brings to the relationship. So I’ve got to tell you, I feel very lucky.

Matt Schlegel:

Yeah, very complimentary relationships in your life.

Josh Elledge:

Yeah. Listen, I think that this ain’t my first rodeo, I’ve been in business for myself for decades, and so this is my second seven-figure company. One thing that I’ve learned in terms of building a team is I absolutely recruit for my deficiencies. As a leadership team too, we’re very conscious about how people show up and we really think hard about, “Okay, this person’s coming across in this personality style, but I’m not sure that’s what we really want for that role.” and so we very… I mean, we hire for personality, that’s really important for us. I think that’s one thing that wisdom and experience will teach you as well, that if you aren’t cognizant of what people bring to the table in terms of their soft skills and just how they’re wired and how they filter, you’ll learn it eventually, hopefully. Otherwise, it’s going to be a big costly, expensive mistake, time and time and time and time again.

Matt Schlegel:

Right, absolutely. Well, that’s so great that you are using the Enneagram in that very powerful way to build a complementary team and then lining up the right style and dynamic for the roles that you’re recruiting for. That is a great application to the Enneagram. As you were first learning the Enneagram, what did you discover about yourself that you hadn’t appreciated before?

Josh Elledge:

I also feel like because I’ve been highly, highly focused on personal development, personal growth, recognizing my weaknesses, and if I go through and I’m really kind of reading articles and books we talk about what are the fail points. Fail points, this isn’t a good, a good term. But where does Sevens need to be very conscious about their own shortcomings and maybe how they might show up in a relationship in a way that you need to be aware on this. I feel like I’ve worked on those quite a bit. But, I also, when someone says, “well, aren’t you going to work on that?”, I said, “No, no I don’t really enjoy accounting for example, or the details, or dealing with customer service issues or whatever”. I very intentionally delegate and promote to solve those issues. Because here’s what I know is that if I get stuck doing roles that I know that just it’s not fun and in cases makes me feel bad about myself, or it demotivates me or something like that. I could evolve to like that stuff, but I kind of don’t want to and I’m okay with…

Matt Schlegel:

There’s other stuff to do.

Josh Elledge:

Yeah. Like asparagus, I’m sure some people love it. I just don’t and I’m okay giving other people the asparagus. I cook it, I’ll make it, I just don’t want to eat it. Right. And so, all other people eat my asparagus.

Matt Schlegel:

So what I’m hearing is that you really appreciated that your style is much more big picture. It’s much more looking at novel things and not necessarily diving into detailed work, grinding, detailed work that you’re just fine demotivating. And rather than just force yourself to do that, “Hey, let’s find somebody who likes doing that work because there’s plenty of people who like doing that work,” have them do that. Then you can focus on the work that motivates you and encourages you and just makes you feel better. That….

Josh Elledge:

Yeah, I feel like I have a moral obligation on behalf of my team. I have a moral obligation on behalf of my family if I want to grow this company and I want to provide for my family. I have a moral obligation to being conscious about my strengths and weaknesses and certainly, I have a moral obligation to serve my audiences and my customers in the way that I do best. In fact, one thing that I’m very clear on with them, as I said, listen when you get in I’m going to give you to better hands in terms of deployment ,and build out, and that sort of thing. You wouldn’t want me doing that work. It would end up being… Because a lot of times, and here’s the thing. I want to talk to like business founders and CEOs and stuff right now, if you are working in account-based services like if you’re an agency owner, you’re a consultant, you’re a coach but you’re at the point now where you have a team.

Josh Elledge:

A lot of times your clients will make investments because they really like you, they believe in you. They really resonate with you and your philosophy. We have to let our clients know coming in. I know it sounds like it would be a lot of fun if we were to be on all these calls together, but I just have to tell you I’ve tried that. It ends up being really frustrating because I’m just not the… I love being on a call. I love coming up with lots of other ideas, but I love having somebody else on the call with us so that they can make sure to execute on everything and they don’t let anything fall through the cracks. If you’re relying on me, it’s going to strain our relationship. So if you don’t mind, I’m going to bring some key team members that they are the best in the world at this very nichey, nerdy, specific thing. You cool with that? Yes. Great.

Matt Schlegel:

So, and that again, allows you to be kind of freewheeling and talking and sharing ideas, and then you have somebody else just following up and making sure that everything is being tracked and monitored and taken note of so that you can have great follow up later.

Josh Elledge:

That’s it. Listen, I am just so grateful. To the person who’s listening to our conversation right now, you know this stuff and I got to tell you there are major weaknesses and threats as you’re doing your… that you will be able to better overcome as a result of your awareness of how these personalities, the dynamics of these personalities, how they mesh together, work together, recognizing your own weaknesses, and being okay with working around that. Again, it would be the same thing. There’s certain aspects of taking care of my car I’m good at, I can do, and other aspects, I just trust the hands of other people that are much more, better equipped to do that stuff.

Josh Elledge:

Don’t let your ego get in the way of a greater impact in the world, because I only do, let’s say maybe overall within my company at this point, maybe three to 5% of the total work that gets done week to week to week. I want to be the best in the world at that three to 5% and that’s why I talk about this moral obligation. Again, particularly I’m talking to my leader friends out there. Don’t get in your way. Don’t get in your own way because of your arrogance or ego. Let it go.

Matt Schlegel:

Well, you’ve brought up already a couple of really great applications of how you use the Enneagram One in recruiting and then also just in your working day to day, just figuring out which style is going to be the best in a certain situation. That’s just two excellent ways to use the Enneagram. Just as we wrap up and feel free to jump in, if you want to ask something else, but I do want you to give advice for other leaders of Enneagram Type Seven. Specifically, what advice would you give to them as they’re on this journey of self-realization and self-awareness?

Josh Elledge:

Yeah. This is important for me as a Seven. So Sevens love their variety. They can get bored. What I want you to do is I want you to treat your work almost like a game or a challenge. What we know, and I’m a big fan of like atomic habits, James Clear kind of, where the difference between a champion and an amateur is that a champion just does it longer. They just do it more. Well, you might listen to that and say, “Ooh, I don’t know how a Seven’s going to do that”. So, we want to look at what is the thing that we can do that gives us… For me, again, I like variety. So what do I do professionally? Well, as a CEO or a founder, listen, we go back to Michael Gerber, E-Myth, I have one job.

Josh Elledge:

I got to grow this company. I am responsible for growth so how can I do growth in a way that meshes with my personality? What do I do? Here’s what I chose. I am a very avid podcaster and while I do use the same mechanism, day in, day out, I have about seven to 12 interviews with seven to 12 different people every single week. I am constantly learning from new people and I get to ask them any question that I want to ask and I have made that a part of how we grow our company. For me, podcasting is the ultimate networking tool, so I have a business justification to do the thing that me, as a Type Seven, can excel at. I’m generally pretty good at connecting with people in rapport and I love it. I love people.

Josh Elledge:

Sometimes it’s going to take a little bit of mind mapping. You’re going to need to work with someone who can really help you identify your strengths, weaknesses, and “okay, well, how could we do this in a way that works well with your personality type?”. I got to tell you, Matt, I am very grateful, very grateful. I mean, I’m the founder, so I mean I had some say in this, right. But I’m very grateful that I found a way to make it work. For those leaders out there that you know that your current role is just not meshing with your personality type, again, I would find a coach who understands this, and you’re going to have to do some serious mind mapping exercise where you can think about “what are some ways that I can tailor my responsibilities, or I can accomplish the things I need to accomplish that are absolutely going to be in alignment with my ability to show up day in, day out”.

Matt Schlegel:

Right. Oh, that is such great advice, Josh. Just a couple of things. One, just as you point out, you have built into your week lots and lots of variety meeting new people, which is just right in the sweet spot of the Seven, something they love to do. I noticed that you keep using that word, “learn”, “learn from,” and what I found is that people who are growing in their careers will tend to move along their path of integration towards that integration point. For the Seven, it’s the Five which is the epitome of learning all the time. You are actually building in that growth right into your daily or weekly activities by just learning from other people all the time. You really have wrapped up a lot of healthy dynamics in what you’ve situated yourself in and I applaud you for that. Just really sounds like a super fit and I could just tell it from your enthusiasm that you love it.

Josh Elledge:

Yeah. Matt, thank you so much and thank you for the work that you’re doing. Again, leaders like me really appreciate being able to just make those big discoveries about ourselves and, most importantly, to take action on those discoveries. Again, it’s one thing, “Oh, I know the Enneagram. Oh, I know my personality”. Okay, great. So day to day, what are you doing to go along with that? It’s like knowledge without action. I feel it’s like if I give you a big sack of cash and you go bury it in the backyard, it’s worth nothing. Matt, the work you do, you’re handing out big sacks of cash. Okay folks, go spend that money on stuff that really is meaningful to you.

Matt Schlegel:

There you go and you just handed our audience a huge sack of cash too. So thank you.

Josh Elledge:

There you go. Cash everywhere.

Matt Schlegel:

Thank you for sharing your stories and your wisdom and your experiences. Best of luck to you growing your business. Sounds like you’re just on a perfect track for you. I do look forward to having a conversation in the future. Let’s check in and just see how it’s playing out and how the Enneagram is playing in that.

Josh Elledge:

Matt, you’re awesome. Thank you so much for having me.

Matt Schlegel:

All right. Thank you, Josh.

Matt Schlegel:

Thanks for watching. Wow, I love Josh’s energy. You can feel that Type Seven enthusiasm shine through. Clearly, Josh is very thoughtful and he’s well named his podcast The Thoughtful Entrepreneur. I very much appreciate his insights. That Type Sevens can frustrate themselves by doing things that aren’t a fit for their style and recognize that they can partner with people who complement them and can fill those roles, leaving the Seven to excel at connecting and learning. Things that the Seven are masterful at. He also identifies two types that are very complimentary for the Type Seven, the Type Six and the Type One who are masters at the details, planning, organizing, and follow-up. Things that the Type Seven would rather not do. If you like this, please click on the thumbs up and subscribe to the channel to get notifications of upcoming episodes. If you have any comments, please leave them in the Comments Section and I’ll respond as soon as I can. Thanks again.

 

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