#006 Revolutionizing Success with Jonathan Gregory

Navigating Growth, Roles, and Mastery

Guest & Host

Jonathan Gregory & Steven Morell

Welcome to Speak Revenue, the podcast where we emphasize that revenue is not just a goal; it's a result. In this show, we shift our focus from the output to the inputs. We engage in conversations with sales leaders and entrepreneurs about their remarkable journeys. Our mission? To uncover the true root causes of success. In this episode of Speak Revenue, host Steven Morell engages in a thought-provoking conversation with Jonathan Gregory, a Fractional Chief Revenue Officer and Revenue Consultant. They delve into the importance of internal and external aspects of personal and organizational development using frameworks like the Spider Model. Discover how to unlock individual and collective potential, prioritize personal development phases, and achieve growth, roles, and mastery.

September 18th, 2023


Steven Morell: Welcome to our new episode of Speak Revenue. Remember, revenue is not a goal, it's a result. But a result of what? In this show, we turn our eyes from the output towards the inputs. We speak with sales leaders and entrepreneurs about their journeys. Join us in our quest to uncover and learn the root causes of success. Let's unpack what works for them. And what didn't today with our guest, Jonathan Gregory, Jonathan, so nice to have you here. Thank you so much for taking the time and coming into our show.

Jonathan Gregory: Great to be on board, Stephen, looking forward to the conversation.

Steven Morell: I'm excited, Jonathan. We know each other. That's how I managed to get you into the show, but for our audience real quick intro, who are you, what do you do and why are you so successful?

Jonathan Gregory: Great. Thanks. I'm a Fractional Chief Revenue Officer and a Revenue consultant. I work with different organizations, startups mostly in the series A series B stage, some bootstrapped and manage everything around commercial leadership, a high performing organization. Those are the topics that I'd love to address, to address background in consulting, seven years in consulting, five years, different startups before that it was three years, three years, even in insurance. wide range of topics I covered and yeah, now since, yeah, at the beginning of the year, I would say I'm doing the fractional thing. And it's been great to work with different organizations and see how they progress and how they develop.

Steven Morell: I always think when you get into the fractional part, into the consultation part, you get to see what you love seeing just more of it. Right now…

Jonathan Gregory: Absolutely.

Steven Morell: I know from our personal conversations that you have. Certain topics that you're very focused on. And one is about development, personal development, as well as company and team development. Can you expand a little bit on that?

Jonathan Gregory: I think it comes maybe a little bit from my family background. My mother is an organizational leadership coach. So people talk at dinner tables about how I don't know how school was. We talked about what development models work with the company and how you can take the next step as a person. It's very much in the family, in the blood. And so this is something that's close to my heart and I've been learning about it for the better part of… 

Steven Morell: I have to ask. Did she apply this to the family? Did you, was Tuckman sitting at the table with you?

Jonathan Gregory: Not in that sense, but it's like, she's a coach and obviously that translated a lot into how she built the relationships with her children and how she helped us make decisions and all the like.

Steven Morell: Very nice. Fascinating. Fascinating. You mentioned in our pre conversation, you mentioned the four quadrants. I think you brought something that we can look at to explain to us how quadrants help me to grow my business, but my sales organization.

Jonathan Gregory: Yeah. Yeah. Awesome. It's a great question. Should I go ahead… 

Steven Morell: Yeah, go ahead. share your screen. We've never done this before. So this is the first episode where we actually have something that our listeners cannot see because they are listeners and not viewers. That's another reason to also follow us on YouTube, but we'll try to describe what we are seeing. I'll try to describe what you're showing us. I try to describe what I'm looking at. I'm looking at a quadrant that has internal and external on one axis, and individual and collective on the other. Internal individual reads consciousness, but I let Jonathan explain that.

Jonathan Gregory: Awesome. Thanks, Steven. Yeah. So this is not my model. This is A model developed by Ken Wilber that highly recommends his books. It's a bit difficult to get into. He's very dense in his writings, but I think he's one of the most progressively thinking philosophers of our time. And so internal external. Individual and collective. Those are basically the dimensions that we get in touch with when we are in any form of organizational environment. And so the internal individual dimension is really around who I am and what are my worldviews, values? And how do I approach the table? So in an organizational context it is really about how do I show up every day? And what do I bring to the table in terms of my inner self, right? The external part of the individual is really my behavior, my skills, the way that I communicate, my habits. And a lot of people, when they talk about personal development, they talk about that part. They talk about how to improve my behavior and how to, how can I increase my skills? That's, it's a very, it's in a very important part but it's not the only part and then when it goes a little bit further than that, it's about the collective and that has two parts as well. It's the internal part and then the external part and the internal part is around what we commonly call culture. The shared values, the shared purpose that we're that we're following. So you might have heard the term, purpose driven organization, for that has its roots, this quadrant and it's about like, how do we all come to the table? How do we show up as a team? What is our shared? Value systems for the internal part, and then the external system, those are all the topics that, you know, we talk about every day when it comes to structure processes, agreements, and metrics. For example, your company jaxx.ai they fall very much into that, external systems. It can help us improve our processes and it there, so you can have different tools and different systems or different views on all these four quadrants and improve on all these quadrants, what my experience is. Is that a lot of times people start with the external

Steven Morell: Yes.

Jonathan Gregory: In fact, I think a lot of the external is driven by the internal. I think a lot of times it makes more sense to start with the internal part, which is the harder part And then the external will come from it. And I wanted to show this quadrant because whenever I work with people and they say, Hey, Jonathan, how can I develop, how can I develop as an individual contributor to become a head of sales? How can I develop from a head of sales to a VP, to a CRO? How do I get there? A lot of times to say, what skills do I need to learn to get to the next level? And I think a lot of times it makes a lot of sense to say, what can I do internally? What's my attitude? What's my subconscious bias? What's my fear, and work on that too, to strengthen your inner. And then go and translate that into the outer self, into your behavior and into your skills and the same with companies and saying, Hey, what are the structures, processes, agreements, and metrics that we need? And how does that conform to the culture that we want to build and the culture that we actually have, so there's a development part in the culture and you can go through different, development stages and say, Hey, let's build our culture and each different. Level of culture or development in that sense needs different systems as well. So that's why I think this is very powerful in terms of saying, 

Steven Morell: Let me ask you, let me ask you this. So while I was listening I was thinking, how do I start? And probably it's good advice to start with yourself. And with the internal individual segment of that with your own consciousness, with what worldviews, with what values, with what purpose and with what skills do you show up as. A founder, an entrepreneur, a sales leader, a team leader. Let's start with yourself. How do I use this? Step me through the steps. How do I use this to grow my team on a personal and on a company level? Do I use this in the monthly review? Do I use this in the hiring process? Hands on, down in the trenches, how do I do this?

Jonathan Gregory: I think any topic that you want to address a lot of times has all 4 aspects. That you need to address. So when you say, Hey, we have an issue in the company. So let's say our revenue is not high enough. Where do we, where should we do? And then you can use this and say, Hey, is this an issue of our behavior? Is this an issue with our systems? Is this an issue of our culture? Is this an issue of our consciousness? And it might be all four. It might just have its end or like its root in one of those. And can drill 

Steven Morell: Let me jump in here. Is the main utility of this to analyze problems?

Jonathan Gregory: The main utility of this is basically a framework to think about things and not miss the parts that are not visible for me. That's the main utility of it and saying, Hey, maybe I should focus on another quadrant. Even though the problem appears in another quadrant.

Steven Morell: That's fascinating. Another guest on my show recently. Made me aware that companies only have three types of problems. Not enough revenue, not enough profit, or not enough time. Do you think this could be applied to all three categories of problems?

Jonathan Gregory: The problem then the question is always what's the root cause of the problem, right? And you don't like not enough revenue. There is no action that you can take for not enough revenue. Per se, you have to think about why we do not have enough revenue? And then you go down and then you can think about, what aspects do I need 

Steven Morell: You almost said it was the motto of this podcast. Revenue is not a goal. It's a result, but a result of what and this can help you to figure out. What is the root cause and how can I improve? I'm loving this, by the way. I really feel I just learned something and it feels great. You mentioned in our preparation that there was something with the spider model. Talk to me about the spiders in the system. 

Jonathan Gregory: Cool. Yeah. I, it's a tool. I don't know who showed it to me. And I don't know if I, if it has a name, I call it a spider model. Because the end result is like a spider net of different dimensions that you can look at. And it's a very great tool. Like I used it the first time that I became a manager for the first time. I was like, Hey, now I have employees. And now I have to talk with them about where they want to go? And what can I do as a manager? What can they do as a manager to develop and to be fulfilled in their job? And so someone showed me that model and I've been using it ever since. And it's, I've gotten great results from it. And it's very easy. That's why I continue using it and I'm happy to share it as well. So let me just share the screen here. And it's basically what you can do if you can, pull up an Excel sheet, or you can do it on the whiteboard. And you basically take your team members. Into a room and said, Hey, I just wanted to know a lot of times I do this in interviews too, by the way, in a shorter form, but I want to know what is important to you in your job. What makes you happy? And the question I ask a lot of times is. If you could bake your ideal job cake, what ingredients would you need for that?

Steven Morell: A beautiful way of putting it. 

Jonathan Gregory: Yes.

Steven Morell: And for those who the for the listeners you're scaling this on a scale from one to ten. And the cake ingredients are here. Teamwork, interesting responsibilities, team leadership opportunities, compensation, and it looks like there could be more added.

Jonathan Gregory: Yes. So it's as many as your team member wants to put down. It's the ones that they want to put down the ingredients. So you don't give them any. Like prefabricated dimensions or something. You just ask them what's important to you. And a lot of times they will say three things and then you're like, okay but isn't money important to you as well? And they're like, Oh yeah, money is important to me as well. What about the environment, the working environment? They're like, Oh yeah, that's important to me as well. And then suddenly they start thinking about different things. So sometimes you can help them think about dimensions. Mentioning a couple of examples and saying, Hey, other team members mentioned this and this, how is this important to you? And the goal is really to flesh out usually like 10, 10 or so dimensions saying, Hey, this is important to me. And after roughly 10, they usually say, yeah that's a pretty good picture. If I have all of those topics in my job, I'm really happy.

Steven Morell: And…

Jonathan Gregory: And then the question.

Steven Morell: Go ahead.

Jonathan Gregory: And then the question becomes, like ranking it and saying, how important is 1 of those aspects versus another? I just use a simple scale of 1 to 10, which makes it a lot easier for them to do it. But you could also just say, hey, what's the most important? And we rank that at the top.

Steven Morell: And I see here on the spreadsheet, you're looking at what is important to them and where it is now. And probably where they want to develop a plan from this? 

Jonathan Gregory: Yes, that's the next step then. So 1st, I want to, I Usually dive down a little bit deeper on the aspect and ask them, why is this important to you? So why is money important to them? 

Steven Morell: Hmm. 

Jonathan Gregory: of times it's hey I want to have a good living standard or I want to have prestige because this is a number that I Define myself by or teamwork is great because I just love you know Bouncing by ideas back and forth and so why is this important and how will this make you happy long term a lot of times, especially if you're talking to junior people, they are not very clear. They just say something. And then they're like, and then if you ask them why. Then a lot of times they rethink. So one example is when they say, Hey, I want to be a team lead. And then this question, why do you want to be a team lead? And what makes that part of being a team lead appealing to you? And a lot of times when you drill down, you actually find that it's different things that they're, that they want to achieve with that. And the team lead role might not actually be what they want. But they connect the things that they want. With that role, right? So I think it's helpful to drill down and ask them, what is actually going to make you happy there. And then the question becomes, where are you now? Usually when you start working with someone, they're like, Hey I'm at a 5 out of 10 in terms of my individuality. I want more responsibility, but I'm also. Not totally unhappy with the responsibilities I have, and then you can say, okay let's pick out the ones where we see the biggest gap. I'm saying, Hey, if you're already at a 10, a lot of times there are no actions needed, but if you're either like a 5 or even a 3, then obviously there's some room for improvement. And then the next question I usually ask them, and I don't show them all of it at the same time. I go through it step by step because.

Steven Morell: Because it… 

Jonathan Gregory: In my experience, it's better to ask that question after they've written everything down, then asking the responsibility question is what can you like, you as the employee or as the team member can, what can you do to achieve this? And then it becomes a framing of, Oh, It's not just about, I want something it's, I might have to do something to get it. And that's very powerful. And then they become in a, they come into a state of personal responsibility and saying, hey, I'm responsible for my personal development in this job and in this role. And so what can I do to achieve this? And it might be. Just asking your manager for something. 

Steven Morell: I think you're touching on another important topic that I believe is not valued enough, or it's taken too lightly. And this is the actual title we give people. When you spoke about why do you want to be a team lead? Team lead, I think is a very good example. Team lead is if you ask the team lead what they think. What their job is, and if you ask the team what they think the job of the team lead is, and if you ask the other team leaders from the other teams what they think their job is, and if you ask the people who are they're reporting to about their expectation, you'll come up with very different results. And so you're set up for failure the moment you accept a title team leader without defining and knowing what it actually is for everybody around you. And I believe we should not even use those titles. We should be very careful with titles because you will have exactly this effect. You will have young people who strive to become team leaders without really understanding what they want and why they want that. And not everybody can become a manager. A huge problem in a company is that not everybody can grow in the management role. There are managers and there are makers, and it cannot be that being a manager is more appealing than another pathway, not everybody can grow into this role else you have that I think it's called Peterson effect. That everybody is promoted till they reach a position where they're utterly useless, and they don't get promoted from there anywhere, and you have only people who are in everything over their head. So I think titles and the expectations. Behind those titles are a big part of this or do you have a different opinion about that?

Jonathan Gregory: I agree on the title part. I think it has its downsides. I like the term role. More than I like the title. 

Steven Morell: So…

Jonathan Gregory: So saying, Hey, what's my role in the company and what does that entail? So what are my responsibilities? And I like a system called sociocracy 3.0. It's a great source of patterns that sources from different other systems. And They always say, you can have job security, but not role security. And I think a great way of putting it and saying, you have the role for the time where it's right for you the company to have that role. And once stuff changes in the company, you might need a different role and it might be adjusting to the existing role. It might be just using a different or, fulfilling a different role altogether.

Steven Morell: And you're also going through different stages in your personal development. I recently reread the book from Kim Scott, radical Candor. And in that book I got reminded of that. We are not always in growth mode. Sometimes we are just in stability mode. I just spoke to somebody yesterday who is looking for a new position because the company is growing on a risky path and he has three kids. And he thinks it's a great product. It's a great company. It's a great team. He's enjoying being there, but he has three kids. He doesn't want to take chances. So he's looking for something that is not as advanced, more stable, he's not in a growth mode right now. That might change in 10 years. In 10 years, he has three teenagers, and he might feel like, yeah, I take chances again, and be more in growth mode. But you have people alternating between stability phases where they need to, now I need... A time where just things stay stable and now I have a time where I want to learn, I want to grow. I'm ready to take risks. I'm ready to be promoted into a more responsible role where I might fail and be demoted again or change roles. People alternate between those. It's not something that is a characteristic of a person for a lifetime.

Jonathan Gregory: And then I would add to that. The question is always what does grow mean, right? So you could grow if you're in a family mode and saying you could grow all immensely internally and with your family and shared value system. Even though you might not grow in terms of the role that you're fulfilling, you might grow internally a lot. And in my experience, a lot of my growth happened in the downtimes. And I only realized that.

Steven Morell: Yeah, you might, you might grow your Your role in the company, but you might also roll the mastery with which you do your job, become better at it, become an expert in it. And this should be, by the way, and I know we spoke about, we need to do a different podcast of this should reflect on compensation models. Compensation cannot be tied only to hierarchy. It should also be tied to mastery and skills that you're growing. And I think it's, I'm stealing this from Kim Scott, who says you need rock stars because you need rock stars who are people who show up every day and do their work. Solid like a rock and you need superheroes who are growing and you are finding new opportunities for those rock stars to come in and be solid as a rock. So it's a combination of having both parts.

Jonathan Gregory: That's a nice definition of a rock star. I heard that… 

Steven Morell: Yeah, I'm totally using her vision. And this is how I've started using the term rockstar superheroes and rock stars are very different types of people in different phases. 

Jonathan Gregory: and Steven, when since you mentioned radical candor, I think like one of the most important parts of radical candor for me was the Relationship part, yes, being honest, but, building the relationship and having The emotional connection with the person that you're talking to is basically the foundation of That radical honesty, making that possible. And I think going back to the spider development model, that's also very important, just like the framework, how do I go into this conversation? Is around, hey, I want to help you. Be fulfilled and happy in your job And let's work on this together. So the next step in terms of the The, any like finishing the framework is really what can I, as a manager help my team member? How can I help them to achieve this? They're part of the cake, And then you go down and you say, okay, this is an agreement. This is what we're going to do. And we're going to revisit this in three months or in six months and see, okay, what changed? And what other actions can we take for the next steps to go?

Steven Morell: Let's iterate real quick, tactically. Where can I use this? So we said companies are struggling with three types of problems, not enough revenue, not enough profit, not enough time in all three. They can look at the problem through the lens of this quadrant. They can use the spider model and help me out here. When I hire, when I Review. Where else? When do I have this conversation? What triggers this conversation?

Jonathan Gregory: Usually I have it as one of the first conversations when I get a new team. Like me being a fractional executive at the moment, I consistently have that go into a company and have a new team. So it's one of the first actions that I take. And it…

Steven Morell: Let me jump in here. Do you review yours, your SPIDER model?

Jonathan Gregory: I do share some aspects of it, but I haven't actually. Created one for me in a long time.

Steven Morell: And do you share this before your sales rep shares it with you or do you share it afterwards? Do you go okay, and this is mine and you lift the curtain and it's totally different?

Jonathan Gregory: Oh, you mean how I think I, like how my personal…

Steven Morell: Yeah, You, you talk to you, you talk to your team member about how do, how important is teamwork for you? How important is having interesting responsibilities and they scale all this and rate this and so forth. Fine. Do they ever get to know how your rating is for yourself? They're giving you a deep insight into their lives. Intimate, personal thinking. Do they get the same view of you?

Jonathan Gregory: Usually they don't, but they never asked, so I don't know if it just never came up but…

Steven Morell: It might be totally oversharing. they might totally be going like…

Jonathan Gregory: It might be… 

Steven Morell: Man, I don't want to know that.

Jonathan Gregory: Steven, I think a lot of times. They're the same for me, right? I'm focused on myself a lot of the time, and so I don't always need to know other people's view or like what they need if I'm not responsible for it, right? As a team leader, I'm partly responsible for how my team members are doing and how I can help them develop. It might be more the role of my boss than to do… 

Steven Morell: Me. Yes. That makes a lot of sense. 

Jonathan Gregory: But I would be totally open to sharing this with my teams. I think I'm a very open person and it's not something that I would hold.

Steven Morell: I would probably share this super early on. Like even before they get to talk to me, I would like to give them, and I do this regularly. I give them a manual. 

Jonathan Gregory: Yes.

Steven Morell: As Steven manual, how I answer emails, I don't. And if then I answer, text style, if it's more than five words that I'm upset about, it's easier to get me over Slack than over email and this type of thing. And I would put that and I will. Start putting this in, in, into my package of this as the Steven manual.

Jonathan Gregory: Cool idea. Yeah.

Steven Morell: All right, everyone that brings us to the end of this episode of speaking revenue. I want to thank our guest Jonathan for joining us today and sharing all this knowledge and the reading tips. The reading tips will be on our website. So a huge shout out to our listeners. Your support means the world to us. Remember to check out our website at speakrevenue.com for a full transcript. And we'll put the visuals there and we're gonna put all the book tips there. Everything that you need to get started. If you enjoyed the show, please leave us a review on Apple Podcast and Spotify or wherever you go for your listening needs. Visit us on LinkedIn. Follow us on LinkedIn, like us, comment on us, reshare us, do all the engagement things. We love this. It really helps to get the word out. Also follow us on Instagram and YouTube. And we'll be back soon with other great guests. Until then, stay curious, keep growing and see you soon. Thank you.

Copyrighted © 2022-23 Jaxx Technologies, Inc.

Copyrighted © 2022-23 Jaxx Technologies, Inc.