Scale Like a CEO
Join host Justin Reinert as he sits down with founders who’ve navigated the jump from do-it-all entrepreneur to strategic CEO. Each episode uncovers the key milestones, hard-won insights, and practical tactics you need to build a high-performing leadership team, overcome decision fatigue, and scale your business with confidence. Tune in weekly for quick, actionable conversations designed to accelerate your path to CEO mastery.
Scale Like a CEO
Leadership, AI, and Building High-Performing Teams with Rich Cannon
What does it really take to build genuinely connected teams in today's technology-driven world? Rich Cannon brings extraordinary perspective as someone who's lived in all three worlds of business leadership—founder, senior executive at Microsoft, and "hired gun" CEO.
The revelation at the heart of this conversation might surprise you: despite all our technological advancement, the fundamental challenge facing organizations today is human disconnection. "People really are disconnected at the senior levels of many companies," Rich explains, "which impacts people's ability to change together." In a refreshingly honest moment, he shares how being identified as "the highest ranking yellow energy person" at Microsoft brought him to tears, validating his struggle of leading with relational energy in an environment that prized different qualities.
Rich takes us through his practical approach to transforming team dynamics, starting with self-awareness and creating shared language through personality assessment tools like Insights Discovery. Unlike conventional wisdom that minimizes conflict, Rich advocates for healthy confrontation: "Conflict in a team is healthy," he asserts, explaining how constructive tension ultimately creates stronger connections when teams work through it together.
Perhaps most compelling is Rich's counter-intuitive perspective on remote teambuilding. Having transformed an entire company culture during COVID without meeting his team for five months, he firmly believes connection doesn't require physical presence—it requires intentionality and the right framework. His formula? Combine growth mindset with connected mindset: "We first, me second."
Looking toward our AI-driven future, Rich offers an optimistic view that technology can actually enhance rather than diminish our humanity. Connect with Rich on LinkedIn to continue the conversation about creating more connected, high-performing teams in your organization.
Everybody. If you're not doing AI every day, you're missing out, and so, for me, I'm really working on. Okay, what does the next generation systems really do for us? I think they make us more human.
Speaker 2:Welcome to Scale Like a CEO, the podcast where we dive deep into the strategies, challenges and insights of successful business leaders. Challenges and insights of successful business leaders Each episode, we bring you authentic conversations with CEOs and executives who share their real-world experiences in scaling organizations. Whether you're a current leader or aspiring to grow in your career, you'll find valuable lessons and practical wisdom in every discussion. Today, we're joined by Rich Cannon, a seasoned executive with fascinating insights into leadership and team building. Let's dive in.
Speaker 3:Rich, thank you so much for joining me on Scale Like a CEO, just to get us started, if you can give us a view on your business.
Speaker 1:Yeah, great, I just came off of a role as CEO of Rally you can see it at wwwgetrallycom a change experience platform where I worked with business experts who mostly work with executive teams, and the big question was how do you expand what is done for the senior teams out to the field where you actually impact the customer and the customer experience? And so that was my last role. Prior to that, Immediately prior to that, I was the senior go-to-market lead for the one commercial partner group at Microsoft, being a technology executive, and immediately prior to that I did an e-commerce website development startup which ran for a number of years. Many different experiences.
Speaker 3:Yeah, great, I'm excited to get some of that experience into the conversation. What do you see as the biggest problem in your industry and how are you solving that?
Speaker 1:That particular book has sold millions of copies, but people really are disconnected at the senior levels of many of these companies, which really impacts people's ability to change together. And in a world where AI is influencing everything and technology now affects every role, not just the IT roles or the programmer roles I really think that we have to get back to is our just basic connectedness as humanity and being aware of our own strengths and weaknesses. Not trying to be heroes, not trying to make villains out of people, but just really us being people who come together for a cause.
Speaker 3:Yeah, I think that pervasive anywhere and everywhere is a lack of connection, a lack of community, and I think we need to find creative ways to solve it. It's interesting because we see a lot of these like return to office mandates, but I don't think they're done in the spirit of that it's more about.
Speaker 1:You're just making you know it's just again. It's an authority structure that doesn't work, and it doesn't work whether people stay at home or whether they come into the office. You know, what? What are you doing to create a connected and high-performing team? So, to that end, I have a book coming out next year called Make Great Teams, and it'll be all about, but it starts out with your own lack of understanding of yourself in order to be able to create a connected team.
Speaker 3:That's great. I look forward to reading it. I absolutely agree. Self-awareness has to be the beginning and that's, you know, in my book Creating Belonging. It starts with self, you know when really understanding who we are, all of our identities. So I think that self-awareness is huge.
Speaker 1:I love that title by the way.
Speaker 3:Thank you, you know. I'm curious what makes you unique in the way that you help others?
Speaker 1:Well, this is a good question, justin, I told you in the preamble I thought that question really made me think for a second, and not too many people were founder of a company, then went and did a very senior executive role and then went and became a hired gun CEO, with working with founders etc. And so again working with all across that. I'm about change for the company, change for the individual. What's going on with the way in which that company is going to market with its customers, but also what's its employee experience? I can really connect with a woman, tiffany Bova, who has an employee experience and customer experience. She calls it the experience mindset. But how do those two blend together?
Speaker 1:Because you could be creating great customer experiences and employees are unhappy because they're overworking, or employees can be really happy and they're not really paying attention to the customers, and so that balance is this connectedness, is this self-awareness, is this ability to really relate to others, and so I think that's the unique perspective I bring.
Speaker 3:Yeah, that's great. So you worked across in different ways leading businesses. So you worked across in different ways leading businesses and I'm curious to hear a little bit more about, in these conversations, scale like a CEO. What I'm really trying to get at is understanding what it takes to scale companies, to scale teams, and so I'm curious in your experiences, as you've looked at scaling teams in these different environments and coming into the business in different ways, what are some of the critical aspects of building and scaling a team?
Speaker 1:That's a softball, justin, because as a CEO, if you can't build a team, you can't succeed. Your success is highly dependent on the team you create. I'll give you a story, maybe as an answer. When I came in the rally, it had spent tens of millions of dollars, did not have a lot of revenue traction, had not really solved the product market fit, but it had a team of people who had been working there for some number of years and when I got there, the first thing that struck you was everybody. It was a hub and spoke management style. Everybody worked through the founder or the CEO, but they didn't really have relationships with each other. But as a result, because they had spent a lot of money, not have a lot of traction, everyone was blaming each other. Everyone was a victim, basically, of the system.
Speaker 1:And you're like for me, I start with the idea of how do you get the right people on the bus. Basic idea, and for me that's number one are these people who really want to grow a company? Are they willing to tolerate 100% growth In order to be a person who tolerates 100% growth? Back to that point before you got to be a person who wants to grow. And then, second, can you relate that with other people so that you can really build a connected team, or do you have to be the hero if you will and to really just change the culture? I use personality testing as one way of doing that to get everybody thinking about each other in a different way and really asking people to grow.
Speaker 1:And it's amazing how in a few months time, the people who don't want that leave, which allows you to bring in additional DNA into the team because you only have so much money, et cetera that are all that way and pretty soon, your culture in about six months time and this is in the middle of COVID, when I didn't even meet the people for the first five months. You can do this online. I don't believe people need to physically be together. I personally was 14 years remote at Microsoft and I only had the team in once at the company I was at, so I think this can be done. A culture can be done in person, but it can also be done remotely.
Speaker 3:So what I'm hearing is part of it is this talent selection piece of making sure you've got the right people that are kind of rowing in the same direction and then people that are willing to develop themselves go into self-awareness. I love that. That's one thing that I have for many years when I'm interviewing folks to add to teams. Growth mindset is one of my number one competencies, because that's where people get stuck. If you don't want to grow and learn, then we're going to have a hard time working together. If we're in growth mode and for me the way that I operate is I let people be very autonomous and kind of run with things, but you've got to be willing to learn and grow.
Speaker 1:Well, the only thing I'd add to that, justin, is it's growth mindset with a connected mindset. Growth mindset with a connected mindset, it's us together. If it's a me versus we, you can be a growth-oriented person, but it's me against we. A lot of founders end up in that, for example, it's got to be a we, it's got to be a we first, me second. You know, growth Like I'm growing, as me, which is affecting the we and the we is affecting me, like I'm growing as me which is affecting the we and the we is affecting me. And to me, it's that connectedness that then kind of gets the team going, in addition to the individuals.
Speaker 3:Yeah, I agree with that. You talking about kind of shifting the culture during during COVID lockdown and not being in person. I also I have a great story that I had joined a company. One of my last kind of full-time roles before working for myself was I joined the organization in August of 2019 and was kind of figuring things out and then it was time to start building and hiring my team, and I hired almost the entire team without ever meeting in person. And the interesting thing and this is I always come back to this when people talk about needing to be in person to build relationships it was actually one of the strongest teams I've ever worked on and we still have unquote team meetings to this day where we will get together and just catch up on what's been going on, and we haven't worked together formally as a team for at least three and a half years well, and that's it right.
Speaker 1:You're driving. You're driving your connections as opposed to your career, because Because, honestly, the more senior leader you are, the more your connections are your career I mean the ability to attract talent and bring people in who really can accomplish things at a high level is the critical factor. As a CEO, you're not doing the work, you don't have the time to do the work, so I love that. I mean people who do that, I think are going to succeed over the long term.
Speaker 3:I'm curious to hear a little bit more about this culture shift that you made, and you mentioned the personality testing. But I'm curious what other kind of, what other specific interventions did you use to transform the culture?
Speaker 1:interventions. Did you use to transform the culture? Great question. So we used personality. The one that I used is Insights.
Speaker 3:Discovery. Sorry to interrupt Insights. Discovery is my favorite. I've been an accredited practitioner for 17 years.
Speaker 1:I have been since 2012. So quite a while as well, have been since 2012. So quite a while as well. And the red, yellow, green, blue language gives everyone some language to understand what's in, decode a relational situation and to have a shared engagement. So I really believe that that helps. But then what that does is create a lot of conflict, because now I say you're not taking care of my feelings or you're not hearing my thoughts or these kinds of things, and just listen with your blue energy, if you will, so that I can be heard. So it usually then requires conflict styles and understanding different conflict styles, and it increases the level of conflict, but not in an unhealthy way.
Speaker 1:Conflict in a team is healthy to me. And then the last piece of that is are you going to do hub and spoke management or are you going to do leadership team management? Is the leadership team leading or is the leadership team under a leader? Who's leading? And to me, I really learned that the leadership team is leading and I play the role of CEO, which is the spokesman to the investors, and speak on different things, but I took a lot of the power I had and put it in the leadership team, which then made them have to carry the responsibility of knowing things that maybe in some other companies they don't know, and that to me also, though, expands then the transparency that you can have both with the leadership team and with the larger group. If you can get people who can stomach the responsibility, if you will, and if you don't, again you don't want those people on your leadership team.
Speaker 3:I like that. You called out conflict as being a good thing, and I've talked about conflicts in so many different ways in teams. But one of the most simple ways that I like to talk about it is there's constructive and destructive conflict, and conflict can be good and we can make most conflict constructive as long as we have a positive intent in the way that we're handling it. But it's when conflict becomes destructive that just tears apart teams.
Speaker 1:Well, interestingly, there's another book and group that I have worked with at Rally. They call it the beauty and pain of conflict. But they would even say you can take the destructive energy and use it as creative energy in the team if you can move through it. If everyone just separates, obviously what you've done is maybe irreparable damage to the organization. But if the team stays together through it, you know and it survives the ups and downs of you know, even if a conflict becomes personal. But to actually say hey, someone else on the leadership team says hey, that was really personal, you know what else is going on for you and to keep at it as an organization you really can create a deeply connected, high-performing team. I believe that and I've seen it in teams over the years.
Speaker 3:I want to dig a little bit into you know it is. It is rare that I've seen you know a CEO or you know business. I hate saying business side because our talent professionals are in business, right, but like a business leader who has gotten accredited in a tool like insights discovery and I'm curious going back to 2012, what was the impetus to drive you in that path?
Speaker 1:Great question. I actually got a call from Insights because I lead with Yellow Energy on their thing, and for me it's yellow, red, green, blue. And they called me and they said Rich, we're trying to figure out how you're working inside of Microsoft as a senior director, because you're the highest ranking yellow energy person in the company and so every day must just be painful because it's a company full of blue and red energy leaders. I literally started crying, justin. I started crying. I was like I felt very seen by that comment. It was very difficult because I lead with a relational energy in a company that doesn't value it. You know essentially, and so that's what led me to be the practitioner and to you know, just help everybody become who they were, rather than trying to stick everybody in the mold that management was trying to do. Why can't we each be ourselves? And that again part of this whole thing that I'm sharing with you on fully being yourself and leading. You don't need to be someone else.
Speaker 3:That's so great. I love that they would do that, and it speaks to I mean, I just love my relationship with Insights over the years and so it speaks to how they are genuinely interested in helping people do work better and become more connected with themselves. That's so great. So, rich, i'm'm curious what's next. So you've got I think you've got some plan. What are you up to now, ai?
Speaker 1:ai, ai, everybody. If you're not doing ai every day, you're missing out, and so so for me, I'm really working on okay, what does the next generation systems you know, really do for us? I think they make us more human, and some people may think they steal our humanity. And you know, those people tend to live in Silicon Valley and in Seattle, and I like to make fun of those places a little bit, because you see people in a coffee shop sitting by themselves drinking coffee with headphones.
Speaker 1:In Atlanta, where I'm from, no one goes to a coffee shop to sit there by themselves. Generally, they go there because they're going to meet with somebody and they're going to connect, and so I want the culture that I live in to really use this stuff, if you will, to help people connect even more effectively in their organizations, with their communities, and to become even better connected as a result of the use of the technology. And I see some ways you can use it with things like insights, as well as getting to other people who can help you grow, because technology can't help you grow. It can just give you feedback, and the feedback is really valuable, but you got to use the feedback to get to a person, we'll see. Can you make AI that does that and really makes organizations better and communities better? I think so.
Speaker 3:AI that does that and really makes organizations better and communities better? I think so. Yeah, I think one of the things that we have to do is just embrace it. It is generative. Ai is a part of my life and I use it to help me every single day. I love it.
Speaker 1:Well, I think that's the whole world that we're living in now. Right Is that the experts aren't so expert as they made themselves out to be, aren't so expert as they made themselves out to be, and there's a lot of ways to leverage that expertise for normal people living normal lives but who have maybe been given extraordinary responsibilities. And let's all just be people and let's talk about these things that help make the world a better place.
Speaker 3:Yeah, that's so great. Well, Rich, thank you so much for joining me today. If people want to reach out, what's the best way for them to get in contact with you?
Speaker 1:Yeah, I think the best way is to go on LinkedIn and message me. So that's at LinkedIn, slash in slash, rich Cannon, and message me. I'd be happy to connect with you.
Speaker 3:Great Well, thank you so much, rich, okay, thanks.