Reagan Cannon: Lead like an Executive - Why women fail to scale
Jen Porter (00:00)
Hey, lioness, welcome to the show, Lioness Conversations, where we help women be brave, to lead with confidence and joy, and to find the path to the most meaningful work of your life. I'm your host, Jen Porter, leadership and empowerment coach for ambitious and heart-centered women. Today, I have a very special guest, Reagan Cannon. Welcome to the show, Reagan.
Reagan Cannon (00:24)
Thank you for having me, Jen.
Jen Porter (00:27)
So Reagan and I met through a mutual friend and we had a quick zoom call. Then we had dinner and we've become fast friends and you were in for a real treat today. So before we jump in, Reagan, I just want to give people an understanding of who you are. So I'm just going to share a little bit about your background. So Reagan Cannon is an international leadership speaker and coach with proven tactics and insights from over 20 years of experience.
at Fortune 15 companies, including executive roles at Amazon and AT &T. As a true global thought leader, she has delivered keynotes, coached global leaders, produced a TEDx talk, and conducted development workshops for thousands of people in more than 20 countries on six continents. So, Reagan, we're so glad that you're here. There's so much that I think women and girls are going to get out of this episode.
The thing that struck me when you and I met was how bright your light is. You have such incredible energy and it's contagious. It's so much fun to be around you. And the other thing that really has struck me as I've gotten to know you better is that you not only have all of this experience and expertise, but you actually want to transfer that to others. You want other people to elevate. You want to teach them
Reagan Cannon (01:50)
Absolutely.
Jen Porter (01:56)
the tricks and the tools and build that confidence to be able to get to those levels. And that's what is so exciting about this conversation that we're gonna have today.
Reagan Cannon (02:06)
Yes, absolutely. doesn't, it really, I started leading people when I was 19 years old, but even before that I was in roles where I was in leadership and What I like about leadership is exactly what you just said. If I can take what's made me successful, turn around and make you successful. That is awesome. So that is exactly what I'm trying to do. So I'm glad that that's apparent.
Jen Porter (02:34)
So you're a speaker and a coach now, but you have not always been. I mean, you've been in these leadership roles. You've been inside companies and organizations before you went out on your own. So tell me a little bit about where you started. You mentioned leading as a 19-year-old, how did you sort of find, what were your first steps into your career?
Reagan Cannon (02:37)
Mm-hmm. Mm-mm.
So when I was very young, knew like, I knew two things about myself. One, I wanted to be a speaker. That was absolutely from 12 years old. I knew that I wanted to be a speaker. I remember the exact moment that I knew that I, that was like my ultimate calling. I also knew I wanted to work in business. I loved business. was one of those, when I was 16 years old, Jen, used to tell people,
I want to be a retail management consultant and I want that was me as 16 because I worked in retail, thought I was good at and thought, well, I could teach other people to do this. And so really for me, I was that kid who never changed their major was very, very focused, knew what I loved doing because I just loved, I love business. Makes sense. My dad is an entrepreneur. My mom is an HR. So I kind of always had this sort of root of wanting to be in business.
And so when I was in college after being in, you know, after being in college for about three years, I knew I needed an internship. So I actually drove across town in traffic in LA to the UCLA summer internship fair. Cause I went to a small private school. We didn't have like big companies coming up and being like, would you like to be an intern for us? Like that was not happening. So I had to go to the big companies. And I remember I got to the UCLA summer internship fair.
And I walked up and I'm like, hi, I'd like to come in. Our career center said we could come here and come to the they're like, no, this is only for UCLA students. And I was like, I just drove almost two hours across town in traffic, like LA traffic, like in my suit, ready to go. And you're not going to let me in. they're like, no.
So I walked away and then I did what anyone would do, which was I just grabbed my notebook that had my folio, that had my printed resumes. And I just walked in like I was supposed to be there. It was the 90s, so there was no scanner or anything like that. was like, the non-technology was in my favor.
Jen Porter (05:12)
Just fit in.
Reagan Cannon (05:17)
And I walked in there and I walked around and handed my resume out and many people were like, no, you don't go to UCLA. We're really only recruiting the big four in California. You don't go to one of those schools. And then I got to Pacific Bell, the phone company, and I handed my resume and he's like, wow, you drove all the way across town. You're already in a management position. You're really impressive. Now, unfortunately, we're recruiting from the big four.
but if there's a spot, I'm gonna hold your resume off to the side. I was like, okay, great. It was the only positive feedback I got. And I waited and waited. And luckily there were people who were like, yeah, I don't wanna work at the phone company. And I was able to get an internship, which led to me getting into leadership development program, which catapulted my career at AT &T. So I spent 17 years at AT &T and really rotated around, got different experiences, worked in.
Jen Porter (05:58)
You
Reagan Cannon (06:12)
all different parts of the company. And I came to a crossroads where I had been in Southern California this whole time. In fact, when they launched an entertainment product, I worked in entertainment. mean, there was all kinds of experiences. And then there was a crossroads where everything was happening at the company was happening in Texas. And I was like, my gosh, as a Southern California girl, I was like, I'm going to die.
going to Texas. Like there's no way, like I don't have big hair. I don't say y'all. I don't ride a horse to work. Like I was like, how am I going to survive in Texas? my gosh. Like I was like, it's like death, I, I, I got an opportunity to move to Texas. And honestly,
I, if my house had not been upside down, I had lost so it was 2008, 2010, by the time I finally got an opportunity and I had lost my home had lost so much value, but because I was going to move as a chief of staff, got executive relocation and it allowed me to get out of my house. Um, and that package included some help to get out of your house and move and all this stuff. Honestly, Jen, without that, I would not have moved to Texas and it ended up being the best thing for me.
So moving to Texas, I made amazing friends. As it turns out, they drive cars, not ride horses to work, very helpful. It is a very unique place, Texas, but I did love it. I did meet a lot of amazing people. My career really moved up very quickly there because that was at the hub, the center, everything happening. And at one point, it had taken me a long time to advance from direct.
from associate director to director. Director was a big jump at the company and I just couldn't make the jump, could not make the jump. Finally took this chief of staff role, which think about it, Jen, like, you know me well enough now that behind chiefs of staff work is very detailed behind the scenes supporting someone else. Not exactly the definition of Reagan cannon. I was like, this is memory, but I got tutoring.
Jen Porter (08:24)
true.
Reagan Cannon (08:32)
of what it meant to lead a large organization. I got a front row seat for three years under these amazing leaders, learning from amazing leaders. And so when the opportunity came, and I talk about this in my Ted talk, when I finally got the opportunity to interview, to be promoted, I was really ready. I was really ready. I went for it. And then by next thing I know, I'm leading teams of 5,000 people, leading huge organizations.
And that was an incredible opportunity. And eventually Amazon, friend of mine went to Amazon and got connected to someone at Amazon and moved back to the West Coast to Seattle to work for Amazon. And that was really incredible because that's just the hub of tech and what was happening and to be at the epicenter of an amazing company. And there's so much tech in Seattle and I learned so much. grew so much.
leading large operations, technical teams, global teams, such, such, good tutoring, but I always knew I wanted to go out on my own. so eventually after having a great career at Amazon, I decided, you know, eventually it was time and I had been working towards it for many years. And I know we may talk a little bit about that journey of going out on my own and finally making that step. And so for now, the last two and a half years,
I've been out on my own and being a full-time entrepreneur and that's...
Jen Porter (10:05)
There is a whole
other story within that that we'll get to about that path. So what I'm noticing in your story is that there were these both decision points and opportunity points where what I notice about you is that you had resilience and courage. So how did you, as a, let's call it a teenager,
Reagan Cannon (10:08)
Yes!
Hmm. Hmm.
Jen Porter (10:32)
how did you know that you had it in you to lead, to take on a management role at such a young age? And then follow-up question, when you were turned away at that UCLA career fair, what made you persevere and continued? I think I would have turned around and left. There's a part of me that's kind of a rule follower. So what was it about you that
Reagan Cannon (10:59)
and yeah
Jen Porter (11:02)
that gave you the gumption to go for some of these things.
Reagan Cannon (11:08)
You know, I attribute it to a few different things. think sometimes you think you're going to go from. I've never, you know, I've no management experience to leading all these teams right away. Well, I had a lot of steps in between, you know, I volunteered at clubs, at school, at youth group, at church. I stepped into leadership roles. Even when I was in high school.
working at the Limited Too which if you remember the limited to is very like all the tweens shopped at limited to is like so cool to shop at limited to because I could buy my scrunchies and my chokers and like my fuzzy sweaters like very 90s but it was one of those moments where I noticed that when they had new people starting they would have them work with me.
so that I could learn from me. And so I would just say, sometimes we think it's, women we've kind of followed to the trap of like all or nothing thinking. And I think I just sort of inched my way in. Like, first I'm going to lead a club and then I'm going to kind of be a mentor person at work. And then I'm going to, and so really just kept stepping into roles of leadership and influence. And then eventually when there was an opening for me to be formally a manager,
What I realized, and this is my framework always, is if you look at my career, like, wait a minute, first you were in telecom and then you were in it then you kind of transferred to the entertainment department. Then you transferred to the wireless department. Then you moved to e-commerce. you, you know, how did you do this? For me, instead of thinking about experience, I think about skills and capabilities. And so it's about an inventory of skills and capabilities.
So if you can inventory your skills and capabilities and then try to work to build those skills and capabilities, well now you can transfer those skills and capabilities and leverage the confidence you have in that skill and capability, not the confidence you have in experience.
Jen Porter (13:15)
So that makes sense. My curiosity
though is were you really that strategic, that young? Or are you this hindsight looking back and seeing like, this is actually what I was doing. Was it really intentional?
Reagan Cannon (13:29)
It was a little bit of both. think what I realized early on was I did have this notion of I need to be, want to, I am multifaceted, I've always been sort of multifaceted. Even in high school, I was cheerleading. was also in musicals. I was also in choir. I was also in a bunch of different.
electives, and I had a bunch of friends from all different kinds of groups. Like I've, I've always been sort of multifaceted. So I think the concept of not trying to pigeonhole yourself, but really trying to be multifaceted and collecting up friends and collecting up different hobbies and collecting up different things, that sort of pattern was there early. Was I really like, I'm going to make a list of skills.
Jen Porter (14:16)
Yeah.
Reagan Cannon (14:21)
at 16 and work my way through them. Probably not that like I was pretty strategic, but probably not that strategic. But the pattern was there.
Jen Porter (14:22)
Find them and develop them.
You were probably following your intuition and your areas of passion because that would have been enjoyable for you to have your hands on a lot of different things, right? So some of that was just like, ooh, that looks fun. Let me try that. What I'm thinking about is most of the women that I work with are already fully in their careers. And now they're trying to figure out
Reagan Cannon (14:40)
You got it.
Jen Porter (14:53)
Do I want to do this for the next decade of my life or do I want to make a significant transition and do something more meaningful, more fulfilling and something more fun? But as I hear you talk, I'm also thinking about the younger generations. Those that might be girls still, maybe they're in high school, maybe they're in college, maybe they're young professionals.
Reagan Cannon (15:08)
Mm-hmm.
Mm-hmm.
Jen Porter (15:17)
And these are some really good tips to keep in mind that, you know, because it feels impossible to go from where we are in an entry level role to leading a division of a company or leading the company itself. And so these are some ways that I'm hearing you say, get involved, you know, take on some of these like club leadership roles, know, civic leadership opportunities.
Reagan Cannon (15:27)
Mm-hmm.
Mm-hmm.
Jen Porter (15:47)
volunteer work, internships, because that's how we explore and learn and really begin to understand ourselves and what we have to offer because we have no idea what our superpowers and strengths are until we use them. And then we get feedback that like, wow, we want to send everybody to Reagan to get trained because she's really good at her job and she's really good at training others to do it. But you wouldn't have known that if you hadn't been in that situation.
Reagan Cannon (16:14)
I think we want to deal with trees when we really need to deal with seeds. You know, we want to be, we want the tree like, well, I need to be fully baked and have all the education and have all the experience and have all the things. We want to be a fully fledged tree before we do anything. And I'm like, how about just throw out some seeds, you know, try some things.
Jen Porter (16:38)
Mm.
Reagan Cannon (16:40)
have more of that experimental mindset versus that perfection mindset. Let me experiment. Let me try it. Let me dabble in, like you said, just let me just try joining this club and let me try raising my hand for a small leadership position or let me try this other thing or let me try this other thing. And I think that's where I think find a lot of particularly women, get paralyzed because we want to be a tree. We really need to be a seed, you know, that's.
Jen Porter (17:07)
Such a great analogy and
a great point. And I'll tell you what the kind of vulnerability that comes up when I think about this, but It makes me also think about how women often feel that they need to have 100 % of the qualifications before they'll go for something. Right. And this is exactly what you're talking about. They want to be the full tree. They think they need to be the full tree before they can step into the next level. And it's not true for anybody. Nobody has it all.
Reagan Cannon (17:30)
Mm-hmm.
Mm-hmm. Mm-hmm.
Jen Porter (17:36)
And
yet when you talk about the seed, what I think about is just how uncomfortable that those phases of growth are. There's insecurity, right? There's truly vulnerability because we don't have our roots. Our roots aren't deep yet. And so we can be blown over really easily. And there's a lot of stages of growth when you think about from a seed all the way to a tree.
Reagan Cannon (17:46)
Mm-hmm. Yeah.
Mm-hmm.
Jen Porter (18:06)
That's a lot. There's a lot of patience that's required in that. And there's also some hope that's required that someday if I put in the work, then I'll get to be those, I'll have the fullness of my branches to be able to offer to the world.
Reagan Cannon (18:06)
Yeah, there's a lot.
Mm-hmm.
Yes. Yeah. And I think, you know, even like, when I moved to Colorado, we bought a fairly new home that had the trees that had still had the sticks on them that supported it. Right. Because we get pretty extreme weather here in Colorado. So, know, Jen, like we can get some blustery winds and we can get, you know, there's a lot, so they have the sticks. And I think the other thing that we make the mistake of is, while I'm growing, I has to be me.
And I have to be able to support myself. And that's totally not true. Like my, my path has been littered with all kinds of amazing mentors and friends and books and advice and things along the way. Okay.
Jen Porter (19:05)
Yes.
Okay, let's talk about that.
There are women who are behaving as though they're alone. They're operating alone, isolated and feeling the enormous weight on their shoulders, feeling like it's totally up to them. And what we're not always good at is engaging, know, creating a team around us. Sometimes I call it a board of directors.
Reagan Cannon (19:17)
Mm-hmm.
Mm-hmm.
Mm-hmm.
Jen Porter (19:34)
Like just a
Reagan Cannon (19:35)
Yeah.
Jen Porter (19:35)
life board, like who are your specialists around you that can help support in all of the areas of life and work? So that's a really great point because we wanna strengthen our foundation and have literally other people help hold us up, especially on days when we feel like we're gonna fall over, right? Crash and burn. So how did you discover those mentors and resources and
Reagan Cannon (19:54)
Mm-hmm.
Jen Porter (20:04)
that you wanted to like, you know, lean into.
Reagan Cannon (20:10)
So some of them found me. One of my most important mentoring relationships is Dr. Eileen Beshton. She was the dean and eventually the dean of the school of business where I went to school. But when I started there, she was a professor and I literally, old school, paper on the wall, signed my name.
next to a time slot and she became my academic advisor. And she is still to this day, one of my critical mentors. She pulled me at, she coached me all the way through school. And then when I was at a point where I wanted to go back and get my master's, she supported me coming back to the school and getting my master's. And wouldn't you know it right when I was getting ready to contemplate leaving and going and starting my own business, I happened to have a couple of opportunities.
in Charleston where she's located now and could actually sit with her. And she just looked, just coached me right up and is like, you can do this. You've got this. You can, know, and so there's some lifelong mentors like that. I mean, I could not have cultivated that. That was just, you know, that was amazing. And just providentially getting connected to her by signing my name on a, a flyer for like the 9 45 to 10 o'clock academic advising slot, you know,
Jen Porter (21:16)
Wow.
Reagan Cannon (21:36)
so some of them found their way like that. And then I would say, you know, I've gone out of my way to try and find people when I'm in different phases of life. So there's like long-term mentors like that. Then there's kind of situational mentors. And really when I'm in a situation going and finding someone that I can then talk to, mean, one of my mentors, I just met with a woman, you know, that is a,
tremendous Pat Myers. She's an incredible partner and support for me. And I had a really difficult client issue. We sat down and we actually hammered through the client issue together because she's a coach and I'm a coach. We can kind of like talk through what was her technique. What would she do? So sometimes I think sometimes we put a lot of pressure. So it's like, I've got to find a mentor. They're gonna be my life mentor. This is like true. You know, there are people who are going to be your life mentors and there's going to be people who you just got to call situationally.
and say, hey, I got this challenge. Can you help me work through this challenge together? What I would say is I always work to cultivate relationship, genuine relationship. When I mean cultivate, I don't just mean I'm nice and friendly, which I'm not that nice. I'm really friendly. I'm more fun than nice, but I'm like, you know, I try to like build relationship and then you've got to maintain that relationship. And that's the part where
Jen Porter (22:58)
you
Reagan Cannon (23:01)
I think sometimes we let relationships lapse and we're disappointed when we don't have, we, we don't have someone to reach out to, but we were just so busy and we didn't have time and we didn't follow up or when we were in town, we didn't want to bother them. So we didn't text them to tell them that we were in town, you know? So it really is intentionality. And I think if we can cultivate relationships of intentionality.
Jen Porter (23:13)
Mm-hmm. Yeah.
Mm-hmm.
Reagan Cannon (23:30)
When you get in that situation where you really do need someone to call on, you have that equity to do it.
Jen Porter (23:38)
I want to talk about relational courage, but before we do that, I want to share a tip with the listeners because, and it's related to how to build this strong cohort around us to help us when we need it. One of the things that I, I felt really alone in my leadership path, my journey. I felt like I was stepping into these,
bigger roles, felt bigger than me. And so I really had to grow into them and my confidence, you know, was being stretched. That's for sure. And so whenever I would go to a new organization as a leader, as a new leader, I would seek out a mentor, somebody that had been in the company who was on the executive team, who would be willing to pour into me. And I just humbled myself and asked, you know, I would ask those around me, particularly my manager.
Reagan Cannon (24:06)
Mmm.
Hello. Good day.
Mmm.
Jen Porter (24:34)
and say, really want to mentor, this is what I want to develop, who in this organization do you think would be good for that? And here's what I'm thinking. And then we would kind of narrow it down and then ask the person. And they always said yes, because people tend to want to share their expertise and they're pretty generous. They want people to be successful in their company. that's a...
Reagan Cannon (24:36)
Mm. Mm.
Yep.
Jen Porter (24:57)
It isn't always gonna happen organically. Sometimes you literally have to raise your hand and say, would you help me? Would you advocate for me and be on my side?
Reagan Cannon (25:07)
Mm hmm. You're so right, Jen. my very first job, I did not know how to be a sales leader. was, I was leading a team of 17 people right out of college. I had never let us say, I really had no idea how to lead this call center organization. And I just looked at the scorecard and I said, who is at the top of the scorecard? And it was Jamie Clay. And I went and met with Jamie. came.
Jen Porter (25:20)
Wow.
Yep, that's right.
Reagan Cannon (25:36)
bounding up to Jamie's desk because at that time I was really high energy and I would go up to his desk and I was like Jamie, will you teach me? I will be my mentor, will you help me? And that took some boldness. I think you were more strategic Jen asking who in the organization you should meet with and getting a recommendation. But Jamie's like, of course.
He taught me so much, but if I had waited and wallowed and worried and I don't know what I'm doing, floundered and whatever, I would have lost a lot of time. And very quickly, he taught me how to be a good call center leader, a great manager, great lead with integrity and how to lead well. And I learned so much. So you're right.
Reagan Cannon (26:29)
Go find them. Like there's people that are awesome in the organization. And if someone tells you, right. And if they tell you no, then say, you have someone you'd recommend? You know, you're awesome. So who you recommend is probably going to be good. And a lot of times they would have, you know, those people who might say, I'm too busy or I can't, I've got a full load. then say, who would you recommend? Who are the people you think are great?
Jen Porter (26:34)
And the worst thing I can say is that...
Mm-hmm. Mm-hmm.
Yeah.
That's right, keep going down that path until you find what you need. So I remember from our conversations and some of the work that you do that one of your biggest strengths is peer relationship, right? Is this sideways relationship. We're always thinking about like leading up and then of course leading our team, but sometimes we forget about this crossway relationship.
Reagan Cannon (26:56)
That's right. That's right.
Mm-hmm.
Mm-hmm.
Jen Porter (27:23)
Talk to me about that. What does that mean? Help people understand what that is? And how did you do that? Because that sounds like a big part of what made you successful in your roles.
Reagan Cannon (27:34)
Absolutely. think, you know, what I realized is I realized this Jen from a negative story. It was like crystallized for me. There was a, there was a woman who wanted to get promoted and she would have been promoted to be my peer. And the way my boss used to do interviews was say, Hey, I want those of you who are going to be peers with this open position to interview first.
And then if you all agree that you like this person, I'll do the final interview. So I was like, okay, that's cool. Cause you know, my boss at the time realized y'all are going to work together much more closely than, you know, like I want you all to be a team. And so you need to make sure this person is going to be a fit for the team. So I interviewed this person on paper, Jen, amazing leadership adored this person adored them. Like they were great, awesome, had great results.
And their team members, even their team members were like, oh my gosh, they're amazing. Their employee engagement scores were outrageously high. They were so good. Everything looked great. And then I thought, you know, I'm going to call some of her peers because she's going to be my peer. So let me, you know, let me call them. And I called them and I, you know, I reached out to a couple of them and I said, Hey, would you recommend that this person
get promoted and they said, let me be really clear. If that person gets promoted to be my boss, I'm leaving the company.
And I was like, okay, tell me more. And they were like, yeah, she's successful. She never shares anything with us. She never shares any tips. Like we're floundering, we're stuck and she won't, all she does is manage up. We reach out to her, we ask for help. She'll never return any of our calls. She won't share with us. And we understand it's competitive, scorecard.
And maybe at first you kind of want to hold a secret to yourself and we get that. But like we're struggling and we're asking her to help us be a peer mentor to help us. She won't help us and she's rude to us when no one's looking. She's not supportive. And at the end of the day, I did not endorse her to be promoted and neither did others when they heard the feedback. And so what dawned on me was I was like, dang, peer management.
is a critical part. And I had sort of been doing it naturally at that point, because I'm pretty relational. I don't know if you know this, Jim, but I'm an extrovert. So that's like natural for me to like to build relationships, but I had just sort of done it haphazardly. And then I started doing it intentionally. And I started being very, very intentional that when I got into a role, I immediately tried to reach out. And so many women I coach at senior level leaders,
Jen Porter (30:22)
Okay.
Reagan Cannon (30:33)
Senior level positions, I ask. They'll say, well, this or that, or I'm trying to get exposure, I'm trying to this, or they won't call me back, or I can't get anything done. And they quickly come to some conclusion like it's because I'm a woman or because I'm this or because that, and maybe that's true. It could be very true. But I ask one question. When was the last time you went to lunch with that person? Well, I was just in an update meeting with them. Not an update meeting, not an email chain.
Not in a staff meeting, lunch, or virtual coffee, or some sort of coffee or happy hour or anything, any personal connection with them. And so many women say, I never have. And part of what I like is the no like trust model.
Jen Porter (31:28)
Yeah.
Reagan Cannon (31:28)
And that's the kind of the scaling of relationships, right? You have to know someone that's just a basic like LinkedIn version. This is what Reagan's about. Here's what her experience is. Like is you get to know me personally. So then you don't just have head knowledge, you have heart knowledge. You know my interests. You know about me personally. You know what I like, what I don't like, you know, and you have humor, my humor and my background and my personality, my beliefs. And you start to get to know each other personally. And then after time you have trust.
And so what happens is a lot of times where I see a lot of women's careers derail is they don't manage their peers. They, and then they need to get things done. And the first time they're reaching out to a peer is when they need something or when something's gone sideways and they're like, well, Reagan, you know, we're professionals here. They should just call me because I'm, we're peers. I was like, okay, well they're human and you're human.
And so let's all like deal with the human-ness instead of the, should be this-ness and recognize that they want to be connected to respected and they want to have a relationship and they're going to be more likely to build trust that no like trust if they have gotten to know you and you've taken the time to invest in them. And so.
Jen Porter (32:46)
And this is some of
the content that you teach, that you speak about, that you train on. Is this peer management?
Reagan Cannon (32:53)
That's
exactly. So my keynote, Conquering the Competence Complex is all about peer management because my platform is really about managing your boss, managing your peers and managing your team and really thinking about the three relationships that fuel your career. And so what I've done is because peers tends to be the one we think of the least.
I put together a keynote on this and it's a keynote and a workshop and it really brings to light for women, wow, I don't think I'm investing. I'm so worried about what my peers think about me. And I'm so afraid of looking stupid in front of my peers or I'm so afraid they're going to think I don't belong here that we're so worried about ourselves that we're not worrying about them. And really it's turning the tables.
and techniques to build those deep relationships. And it's actually a lot safer to like think more about them than yourself. But we're just so fearful that the competence complex tells us, are you really good enough? Are you competent enough? Do you belong here? You probably don't know everything. You know, don't let your peers, don't ask them for help. Don't look stupid. Don't raise your hand. Don't make an idea because what if it's wrong? And that voice is in our head and it,
Jen Porter (33:54)
Yeah.
Yeah.
I
Reagan Cannon (34:20)
alienates us from the relationships. We actually build worse relationships because we're so afraid.
Jen Porter (34:25)
Totally,
totally. So give us an example, make this come alive. When did you use peer management to help you on your path?
Reagan Cannon (34:34)
So I had a peer when I was a global leader, I sat in Seattle with Amazon and I was a global leader. And I had peers in, that meant I had to work with the North America team that included Latin America. I had to work with the EMEA team, which is Europe and the Middle East. And I had to work with the Asia, the APAC team.
And there were leaders over those three areas. And so was really important if I had a global initiative, it's like, cool, that's interesting. We're kind of busy here in Europe. We don't really want to use your global idea. And I realized very quickly that my job, like most senior leader jobs, you think when you get more senior, you're going to have this authority because it's this outlined authority. But then you realize so much of the way you get things done is through influence.
Jen Porter (35:18)
Yeah.
Reagan Cannon (35:28)
And so I really was like, I recognized I needed to build good relationships. So I built relationships with the North America team. Oh, great. Leader, great. We're laughing. We have inside jokes. It's awesome. The Europe team member was in town one day on one of his birthdays and we went to dinner and my husband and I and him all hung out and it was wonderful. We built a great relationship. What was left was a pack. And I was like, I tried everything, showed up. I'm like, hey, I don't know.
Most people think I'm going to see if they like me. I'm going to assume you like me until you show me that you don't. Like I just decided I'm just going to do that because it's cleaner. You know, I'm just going to do that. And so, but this was not working. This is not working. It was not going anywhere. It was very professional, very strict, blah, blah, blah. I could tell it was not in the inner circle. It was not in this person's trust circle. And then somebody told me, he,
loves scuba diving.
Okay. Ask him about scuba diving. Perfect. Got on the call. We had like quarterly touch bases or whatever. I said, Hey, I heard you. I heard you like scuba diving. And when I say Jen, his face changed. mean, completely changed chatterbox 20 minutes later, but every tropical fish under the planet. And from then on,
We had a great, I mean, it was already a very professional working relationship. was, was nothing wrong with it. It was wonderful. From then on, I think we moved more towards that no like trust. And I have to say that that individual became a huge supporter, a phenomenal peer, uh, gave me tremendous insight. Didn't always agree with me, but we would have, we had very respectful debate. I, I still respect him as a tremendous leader and colleague.
Jen Porter (37:07)
Yeah.
Reagan Cannon (37:26)
And it really was, you know, important. And I had to get a lot of things done as a global leader. And it was, it was so critical. And so I would just tell you, sometimes we've to inventory those critical relationships and then really go work towards intentionally building them. And it is amazing what it unlocks when you have that deeper relationship. And sometimes it's easy. Sometimes you got to work at it.
Jen Porter (37:55)
Sometimes you have to work at it. Yeah, I'm noticing your perseverance again in this example, because I think when, and I work with mostly women, so I'm gonna use that as an example, a lot of women will give up in those relationships because they are offended. They can't figure out a way to get this person to like them and work with them.
Reagan Cannon (38:10)
Mm-hmm.
Mm-hmm.
Jen Porter (38:21)
You know, that imposter syndrome shows up, so we make it about ourselves, and it's usually not about ourselves, it's about them. And so you kept persevering until you could find that entry point into that higher level of relationship.
Reagan Cannon (38:23)
Mm-hmm. Absolutely.
Mm-hmm.
Yes. Yeah, that's.
Jen Porter (38:40)
And it's
probably frustrating, right? Along that path until you could figure it out. And, you know, sometimes people just are going to be difficult individuals to work with. Like you may never get there, but you still have to find ways to get to the shared vision and mission.
Reagan Cannon (38:54)
You mean it. That's right.
That's right. And I think that's where we are so afraid of, and I don't like it. mean, I don't like it when someone doesn't want to be connected to me and want to reach out to me or, or, you know, I don't, I don't like it when there's awkwardness and whatever, like there's, there's no secret formula. You just got to go through that, you know, there's, there's some of that, that's just going to happen. I do love that you highlighted perseverance though, because
What happens is we often are so worried about rejection and we, and we do, we, you know, one of the things I, I really think about is I, I'm a natural catastrophic thinker, you know, on the Myers-Briggs I'm an STJ. We, STJs are, we, we are so good at catastrophic thinking. I mean, what's the worst that could happen? I can tell you 29 different ways. It could be the worst thing that could possibly happen. I mean, I, I've got it.
Jen Porter (39:49)
Thank
Reagan Cannon (39:55)
and then this and then this and then this and not, do this as women, right? We have these imaginary scenarios. We have these imaginary conversate, then I'm gonna say that they're gonna say, and then they're gonna hate me and this, you we go all these and I'm just catastrophic thinker, right? What helped me with my catastrophic thinking was learning curiosity. And that curiosity started to creep, crack the door open instead of saying, what's the worst that could happen? They'll hate me, they'll be rejected.
Jen Porter (40:13)
Mmm.
Reagan Cannon (40:25)
You know, they already kind of didn't like it or what was that word in that email? What did that really mean? I don't think they really want, I don't think they really want to get to know me. you know, I don't think they really want to, and I don't think this, you know, we kind of go down this catastrophic thinking and it's to protect ourselves by the way, our neurons, brains, you know this, our brains are just trying to protect ourselves. So we're trying to like get away, get away, you know.
leave, leave, leave, report, report, this is not the right thing. Like leave, leave, leave, like red button eject, you know, like we, kind of like want to do all this, is, know, what, what one of my employees taught me, which is what's the best that could happen and moving towards a curious mindset of, you know what, if I'm going to be that bad on the EEC on, on what could have go wrong? Well, then I think it's only fair that I think of what could go right. And what's the best that could happen. And then
Jen Porter (40:48)
board.
Yeah.
Reagan Cannon (41:17)
Let me go find out and allow the curiosity, the questions and the trying to lead me there versus already making an assumption it's going to fail before I've even started. Or this person isn't going to like me or they're so different than me or that's probably not going to be some of my best friends at work. We're people who work complete opposites of me. And we are, there's still some friends I have. I haven't worked with them in years and I'm still very close to them and they're total opposites of me.
And it's because I said, what's what's the worst that could happen? Well, what's the best that could happen? And let's try.
Jen Porter (41:52)
It reminds me of the experimentation mentality too that you use. So what is, confidence is a huge deal for everyone, whether or not they admit it. There are things that we are insecure about that we try to hide, it stands in our way and it holds us back. So a lot of the women that I'm working with want to get on that path of confidence, right? And confidence requires,
Reagan Cannon (41:58)
Yes.
Mm-hmm.
Mm-hmm.
Jen Porter (42:20)
preparation, right? We just have to be courageous and try things before we can actually build the confidence in it. But the courage and confidence has been a big part of your story and it's how you help people now. tell me about what is relational courage and what, I guess advice, what advice do you have for women who are listening about confidence?
Reagan Cannon (42:32)
Mm-hmm.
Yes. So we want to be confident before we move. So before I try something, I want to be confident I can do it. This feels great. This is an amazing proposition and completely unrealistic.
Jen Porter (42:55)
Yes.
Totally.
Reagan Cannon (43:08)
So what I like to say is confidence is an emotion. Courage is an action. You can have courage right now when you are afraid. You can move when you're afraid. In fact, courage is moving forward in the face of your fear. You my friend Ryan is a firefighter and he's the one who's like, Reagan, courage is moving towards what you're afraid of. And you would know, right? Like he was a firefighter for a decade.
Jen Porter (43:19)
Mm-hmm.
Mm-hmm.
Reagan Cannon (43:38)
He went out there and like ran, when everyone was running away from a fire, he was running towards it. That is courage. What everyone, what you're afraid of, you're moving towards it. And I think what I have found in my research is that oftentimes what we're most afraid of is it found in the context of relationships. We're afraid of being rejected. We're afraid of being let down. We're afraid of being disappointed.
We're afraid of upsetting someone. We're afraid of bothering someone. We're afraid like a lot of it is in the context of what we might do or not do to someone else. And so really it's relationships. And so what I found is over and over again, when I did my research, I interviewed, you know, senior leaders, I hired a researcher, phenomenal researcher. We went out to these in-depth interviews to try and figure out why aren't women getting promoted to senior leadership roles.
And what we found is that it really was not capability. It was not talent. It was not education. It was these strange beliefs that had gotten in our head and been reinforced by society that showed up in the way we interacted in relationships. And so there are ways we're conditioned to act and they might even help us to a certain point, get to a certain level.
and then they work against us when we try to break through to senior leadership. And so we have to change the way we interact in relationships, which means we've got to change, even though our brain is telling, screaming at us, they may not like you, they may not like you, don't reach out, don't do this thing, right? Woo, woo, right? Telling you this, you got to move when you're afraid and interact differently in your relationships.
Jen Porter (45:25)
think
this point in someone's career is so helpful to have a coach. Because those shifts are so difficult to make, because you're going upstream, you're going against your natural tendencies, and the tools and tricks that you've been using for decades are no longer going to work in getting to those higher levels. And so this is where having an objective third party advocate can be super helpful. Because it really is a...
Reagan Cannon (45:31)
Absolutely.
Jen Porter (45:55)
a rewiring of how we operate.
Reagan Cannon (45:58)
It's so true. it's, we have these instincts that tell us to do certain things like perfectionism. This is a great one, right? I do things to a super, super, super high quality. That sounds tremendous on the surface. Nothing wrong with that. Like I do things to a really, really, really high quality and then I'm all about quality and turning in great work. And like when we're more junior, we get rewarded for that and told how great we are. We go above and beyond and you're,
Going the extra mile and all this stuff is so good. So good, so good. Well, here's the problem. When you get more senior, the aperture of what you're responsible for gets wider and wider and wider and wider and wider. And all of sudden you have a lot on your plate. More, you're managing managers or managing managers of managers.
Jen Porter (46:46)
Mm-hmm.
Reagan Cannon (46:51)
All of a you've got all of this on your plate and you've got all these different areas and some of the areas you know really well and some of them you don't know as well. And all of a sudden you've got all this on your plate and you're trying to be perfect at all of it?
high quality at all of it. High quality, by the way, is just code word for perfect. We're so afraid of failing that we're just gonna do it all and be in all of it and manage all of it and have our fingers in all of it. And what people do is they say, know, Reagan's not quite ready for senior leadership. She's not scaling. And so that belief that's rooted in this women can't fail, I can't fail.
Jen Porter (47:25)
Right.
Reagan Cannon (47:34)
I can't be allowed to fail this belief, which catapulted us to a certain level to the point you made, Jen, breaks us when we get into senior roles.
Jen Porter (47:45)
That's right. This is a huge point.
because you did this and this is a part, this is part of what you teach others to get from those, you know, management director level, VP level to executive. You help them make this leap What is it that, that women can do to let go of, you know, kind of even maybe I'll even use a stronger term of break those habits in order to rise.
Reagan Cannon (48:11)
Mm-hmm.
Jen Porter (48:14)
What is, what's the, what are the secrets?
Reagan Cannon (48:17)
Well, what I'll tell you is, I cover a lot of this in my TED Talk. So that would be a good place to start. I would be remiss if I didn't say that, like, start there to hear.
Jen Porter (48:26)
And I'm gonna share the
link because people need to check this out. They need to see this.
Reagan Cannon (48:30)
The first thing we need to do is get an accurate rubric. See, we're grading ourselves. My husband's a teacher and he's, we're grading ourselves on the wrong criteria. So the first thing we have to do is get the correct criteria. And that's one of the things I found in my research is the criteria. I'll give you an example. We think if I do what my boss tells me or the senior leadership tells me to do, and I do it really, really well, they'll notice
and I'll get promoted.
Jen Porter (49:01)
It's logical, right? It's a logical thought.
Reagan Cannon (49:04)
People are like, and, right?
Very logical, very logical. Also not true. Because what happens is when you're in a junior level leadership, this doesn't necessarily hurt you too much because you are more doing, you're doing someone else's strategy. You're living someone else's goals. You're fulfilling someone else's KPIs or performance indicators or deliverable, what they're looking for. When you become more senior,
Jen Porter (49:10)
Mm-hmm.
True.
Reagan Cannon (49:34)
you are the person who has to generate the strategy. You have to generate the KPIs. You have to generate the criteria for success. So all of sudden you go from receiving to sending. And what happens is they're looking for, senior leaders aren't looking for phenomenal doers because phenomenal doers are used to receiving direction instead of giving direction. So one of the ways to demonstrate that you are ready for senior leadership is to actually engage
in some sort of challenge, right? So if your boss says, hey, I want this idea, I want some ideas, I think this is a good idea, and you know it's a terrible idea, you don't just go like, hey, yeah, great idea, I'll go get it done, I'll go be the workhorse, I'll go do all the boxes, I'll be the project manager. It's to come back and say, you know what would, what I'd like to do is build on that, or I'd like to experiment with this and this, or I've got another idea to enhance that, I'd like to take that and.
add this to it and really become an iterative thought partner where you're kind of challenging that you're not just taking what comes, you're actually challenging and adding to it. They have to see that originality and that thought and that challenge and that pushback, or else they just think you are an order taker, not an order giver. And that's, you have to be able to demonstrate you can do that or you can't get to the next level. So here you've got this criteria of I am
Jen Porter (50:39)
Yeah.
Reagan Cannon (50:57)
Getting an A plus in the school of order delivery and following the rules and checking all the boxes. And they're like, cool. Yeah. You're in the wrong school. got to go over there. Yeah. Right. And so you're grading yourself. So that's what I try to really do is help women have the right criteria as to what senior leaders are really looking for. And then really help them think about how do you shift that? And you've got to get the right rubric. And by the way,
Jen Porter (51:02)
It's an old rubric. It's outdated. Yeah.
Yeah.
Reagan Cannon (51:27)
The new rubric looks scary. Back to that courage. Speak up in a meeting, tell my boss I've got a way to make his idea better or her idea better. Are you crazy? They're going to hate that. And there are some bosses who are unhealthy bosses. Okay, we're not dealing with the unhealthy bosses, but you know, there are some people out there, brilliant jerks that get into roles. know, Peter principle, you get promoted to the highest level of incompetence, right?
Jen Porter (51:31)
Mm-hmm.
you
Right.
Reagan Cannon (51:57)
But
for the most part, people want people who can bring original thought to the table.
Jen Porter (52:02)
And I'm gonna
circle back to my point about coaching is imperative at that stage because it is such a shift and it's like learning a new way of walking, a new way of behaving, a new way of speaking, even new language that's needed to operate at those levels. So let's shift and talk about your entrepreneurship journey. know that you've, so let me.
Reagan Cannon (52:15)
Thank you.
Mm-hmm.
yes.
Jen Porter (52:30)
Let's start with, because a lot of the women that I work with are literally transitioning out of a system, a corporation or an organization that they are no longer thriving in and they want to do something different and man, is that a scary leap. is, have a, know, part of the work that I do is help them clarify what is it that you want to do next? How do we create a roadmap for you to get there? And then, and then being with them in the transition.
Reagan Cannon (52:44)
We're here.
Yeah
Mm-hmm.
Jen Porter (52:59)
on those super scary days. So I know that that's a fear. mean, we were so held back by our dreams because we don't understand the how and we don't know how to make that leap. Really it's financial. I'm here at this level of, this is my quality of life. I wanna be here. How do I do this?
Reagan Cannon (52:59)
Mm-hmm.
Mm-hmm.
Yeah
Jen Porter (53:26)
not that easy. not linear. It's more complex than that. how did you do? How did you make that leap? You always knew that you wanted to make a leap. And that's a big piece of this for your story. But what was it that you did to prepare yourself for moving into that entrepreneurship journey?
Reagan Cannon (53:36)
Good night.
So, you're right. I always like to say you can try and exit the freeway elegant off ramp. It's so easy. And then you pull into the parking lot of entrepreneurship. And when you show up, you already have a salary and you already have, you know, all these things. That is not how it is. It is more like you're on a,
Jen Porter (53:58)
You
Reagan Cannon (54:13)
super highway and you turn on your left turn signal and you cut across traffic and you know, it's not elegant, right? There's, but there are some things you can do. So I think some of the things that were most helpful for me was I started thinking about, I mean, I, I kind of knew what I wanted to do, but when it, when I've seen women do this successfully is start thinking about, what are those seeds of experimentation? Try that, try that while you're still working.
Jen Porter (54:18)
You
Reagan Cannon (54:42)
I got a coaching certification while I was coaching or I was still, well, I'm sorry. I got a coaching certification while I was still leading. And that gave me a toe dip into coaching and learning what it's like. I wrote a book while I was still working. And I don't know if I'd recommend that because it's very difficult, but it did put me a little toe dip into what being an author was like. So maybe start with like a short story or a blog post or things like that.
Jen Porter (54:42)
Mm-hmm.
Sure.
Reagan Cannon (55:10)
Start thinking about the problem you're passionate about solving that you can also get paid for doing. Start with the problem you're passionate about solving. I think what we want to do is look at business models. And this is where a lot of companies go wrong, right? They think of a product or a technology and a business model instead of thinking about my customer and what problem they're having and how can I help them solve that problem.
Jen Porter (55:35)
Yeah,
that's right.
Reagan Cannon (55:39)
So you can start thinking about what problems are you most passionate about solving. And I'm part of a group where I've heard the founder, there's co-founders of the husband and wife, but AJ and Rory Vadin, one of the things they say is, your best position to serve the person you once were. And so you can look back in your history and say, what problem did I overcome? Did I face that I would?
I helped solve that I was able to kind of solve or make progress on. And I want to help other people solve that same problem. So I think if you can get really passionate about the problem you're going to solve and then put those seeds of experimentation out there to start learning, that's a lot of it. I think the third thing I'd say is,
It's all about relationships. When you leave and start your own business, it really is about relationships. You're going to need advice from people. You're going to need referrals from people. You're going to need role models that you can be mentored after and learn from. You're going to need all kinds of different people. And so there is nothing stopping you other than maybe your own mind.
Jen Porter (56:53)
you
Reagan Cannon (56:54)
from starting to cultivate relationships and really be intentional about going out to lunches and coffees and chats and joining events and attending a conference and putting yourself out there to meet people because those relationships were the most important thing when I started my business.
Jen Porter (57:06)
Such a good fight.
Yeah, I hear just lean into it. You don't have to tell everybody what you're doing, but just lean into those relationships because you're going to need them. What would have happened, Reagan, if you hadn't made that leap into entrepreneurship?
Reagan Cannon (57:16)
That's right.
Jen Porter (57:32)
I just want to set the stage for what happens when we don't follow our dreams. But if you were still in a company leading an executive level, what would the impact be to you?
Reagan Cannon (57:48)
So I think...
I was really at the stage where...
I had gathered up so many of those skills and capabilities that I needed. And I remember trying to leave at lots of different points in my career. And my husband who has been so supportive, he's like, so supportive, team Reagan, cheerleader, leave when you wanna leave, we'll figure it out financially. If we have to downsize and live in a box, we'll downsize live in a box, whatever we have to do.
But he later told me, Reagan, had that gut, that pit in my stomach because you weren't ready. You weren't ready. You didn't have the seasoning, the skills, the capabilities, the relationships, even the financial, like I had been saving intentionally, right? Even saving intentionally and really being intentional, you didn't, he goes, you just weren't ready. And he said, I would have supported you and we would have figured it out and got you ready, right? But.
Jen Porter (58:38)
Hmm.
Reagan Cannon (58:59)
I think there is a sense of we could never be ready, right? We could never be ready. And we could always wait till it's perfect timing and perfect whatever. And it wasn't when I left, know, it wasn't all whatever, but I do think finding that balance of it's never going to be perfect. And what else do I need to know or learn or experience? And I think I found, and by the way,
Jen Porter (59:07)
That's right.
It's true though.
Yeah.
Mm-hmm.
Reagan Cannon (59:30)
It's 2020 that I had found that perfect equilibrium. but, but I think that's the good gauge is like, okay, I am staying and I think the biggest thing Jen is if you are staying because you're afraid, question that. If fear, I don't like being driven by fear. I don't like fear. Like fear.
Jen Porter (59:50)
Mmm.
That's right.
Reagan Cannon (59:58)
is invited to the bus, it's not allowed to drive. It could sit on the bus, helps me, it informs me, keeps me out of trouble, fears a good thing, but it can't be driving. And that's where if you are staying because you're terrified, or if you're just getting another job because it's the right thing to do and the safe thing to do, question that. Because you're equilibrium, you could be past the point of where it's really right. And that means it's time to go.
Jen Porter (1:00:02)
Yeah.
Yeah.
So good.
Yeah.
Reagan Cannon (1:00:28)
So.
Jen Porter (1:00:29)
And I find that it's
a head and a heart thing. It's trusting our intuition and not just the logic of, I make this work? What is the analytical path to this? But really engaging our heart in the decision of how do we wanna spend our life? And I love that about questioning our fear. Hey, fear's gonna show up, no doubt, but look at it in the face.
Reagan Cannon (1:00:49)
Mm-hmm.
Mm-hmm.
Jen Porter (1:00:59)
Confront
it, have a conversation with it, and then get back in the driver's seat if you're in love. Yeah.
Reagan Cannon (1:01:02)
Mm-hmm. That's right. Let
it on the bus, don't let it drive. That's the biggest problem.
Jen Porter (1:01:10)
So who are your favorite clients to serve and favorite organizations to work with and favorite speaking engagements? Tell us what you love to do.
Reagan Cannon (1:01:22)
So I, my why is to use my words in a meaningful way to help people change their life. That is my, my find my why. and so I love to do that in a few different platforms. First of all, I love coaching women who are on the precipice of becoming a senior leader and need to transfer really need to become, because a lot of times in the reality is
Women are still promoted on performance instead of potential. And so women really need to be performing at a senior leadership role, oftentimes be given that role. So I like helping women become, build their executive acumen, let go of those beliefs that are holding them back and then allow them to transform into that. What does it mean to lead a large organization or lead at scale?
and help them release to do that. So either women who have been promoted and are trying to make sure they do that well, or make sure the women who are trying to cross over. A lot of people say, well, don't men need that too? Absolutely. I coach men on executive acumen and scale a lot. have almost half my coaching clients are men because once you get into that executive leadership role, how do you lead at scale? How do you lead through others instead of trying to do it all yourself? How do you have
lead at that executive acumen and executive level. that's, those are people I love to coach. I love attending women's conferences. I love partnering with organizations that are trying to really lean into specialized research driven coaching and, and leadership development for women. And, I, I love doing executive development where I come in
Jen Porter (1:03:09)
Hmm.
Reagan Cannon (1:03:16)
and work with a team of executives, helping them understand how to scale, helping them understand how to lead, let go of some of what's holding them back. Of course, for women, it's slightly unique, but really a lot of my teaching goes for men and women. And then I just love partnering with organizations that want, this is what I think most executives, when they become executives, they want to be a
good leader. And I help leaders become the executive they've always wanted to work for. And that is, you know, that, that leader you've always wanted to work for, maybe you did work for at one point in your career, you don't want to be that leader. Nobody wants to be that leader. You know, the one that everyone's like, Reagan's email pops up or I have a meeting with Reagan later or like, kind of mood is Reagan in today? You know, nobody wants to be that.
leader, especially senior leader. And so I want to help you become the leader you've always wanted to work for. And so that's really my passion is organizations who say, I want to bring you in Reagan to work with us, to help us be that staff, that executive team, that leadership team that, that people have always wanted to work for.
Jen Porter (1:04:36)
Awesome. So good. So I'm going to share with people how they can find you. And I highly recommend your TEDx talk. It's called The Real Reason Women Aren't Promoted. We all need to know this. And then you have a monthly blog on your best executive leadership tips. So people can sign up for that and they'll find you at ReaganCannon.com, right? ReaganCannon.com.
Reagan Cannon (1:04:57)
That is correct. ReaganCannon.com.
Jen Porter (1:05:00)
So thank
Reagan Cannon (1:05:00)
You got it.
Jen Porter (1:05:01)
you so much for being here today. Thank you for all the tips and just sharing your story. What a joy to get to hear you. I really hope people will check out not only your website, but this TED Talk and share it with other women and girls around you that need these same tips because this is essential stuff. This is research-driven data that can help women in the marketplace. So thanks for being here.
Thanks for being on Lioness Conversations and we'll see you next time. The lioness in me sees the lioness in you.
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