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Managing vs Leading | Executive Advisor Dr. Keith Dorsey

Boundary Breakers · 2026-03-26 · 1h 8m

0:00--:--

Key moments - from our scoring

Substance score

68 / 100

Five dimensions, 20 points each

Insight Density14 / 20
Originality12 / 20
Guest Caliber16 / 20
Specificity & Evidence13 / 20
Conversational Craft13 / 20

Dr. Keith Dorsey's path to becoming a turnaround specialist reveals the power of deliberate skill-building and mindset. Starting in the Air Force where he ranked 19th nationally on his first staff sergeant exam, Dorsey carried his "student of the profession" approach into corporate sales, buying $500 in cassettes from sales gurus and combining their lessons with company training to outperform 49 peers in his first year. His early success as a manager came from doing the work himself - being the "cape-wearer" who closed deals and high-fived team members - until a sabbatical in his 40s revealed he'd created dependency rather than capability. The turning point came when his Southern California team's performance collapsed after he left, forcing him to recognize the difference between short-term heroics and sustainable leadership. This insight - teaching people to fish rather than catching fish for them - became foundational to his approach when managing managers. Moving into senior management, Dorsey focused on promoting people motivated by teaching and helping rather than ego, teaching them to listen twice as much as they speak, and crucially, helping them understand that what made them successful as individual contributors or frontline managers won't work at the next level. His later work with executives transitioning to board roles mirrors this: the skills that built a career in operations don't translate directly to governance. The episode explores why leadership books proliferate yet true leadership development remains rare - suggesting reflection and self-awareness are prerequisites that no instruction manual can provide.

Key takeaways

  • →Being a superstar at your old role while in a new role is actually enabling bad behavior and creating dependent teams, not building sustainable organizations.
  • →The transition between leadership levels requires fundamentally different skills - what got you promoted won't get you promoted again, whether moving from individual contributor to manager or from executive to board member.
  • →Effective leaders listen twice as much as they talk, meet people where they are, allow them to fail with support nearby, and spend their time removing obstacles rather than solving problems.
  • →Leadership books and instruction proliferate because people want a formula, but leadership development requires personal reflection about who you are before any external instruction can take root.
  • →Promoting people into management should prioritize those with the desire to teach and help others succeed, not those seeking to be heroes or wear the cape themselves.

In this episode

  1. 1Early career development and sales expertise
  2. 2Transitioning from individual contributor to management
  3. 3The lesson about teaching versus doing
  4. 4Leading leaders and developing middle managers
  5. 5Building sustainable teams and organizational culture
  6. 6Third chapter portfolio career and board governance work
  7. 7The difference between executive and board member roles

Mentioned

Dr. Keith DorseyUS Air ForceFortune 1000 companyFortune 500 companyUniversity of Southern CaliforniaPepperdine UniversityPacific Crest Trail AssociationHarvard Business ReviewMIT Sloan ManagementForbesBoardroom JourneyBrandon

Guests

Dr. Keith Dorsey

Topics in this episode

Air Force promotions and staff sergeant examinationFortune 1000 sales division turnaroundSales training cassettes and self-directed learningSouthern California and Midwest regional sales teamsTeaching people to fish versus catching fish for themLeadership transitions between management levelsCorporate board governance and board member rolesBoardroom Journey book and companyExecutive search and CEO/board services

Questions this episode answers

Why did Dr. Dorsey's Los Angeles sales team stop performing after he left to manage the Midwest region?

He realized he'd been catching fish for them rather than teaching them how to fish - closing deals himself for the high-five moments - which created dependency on his individual performance. When he left, they lacked the sustainable selling skills to succeed without him.

What was the key difference in how Dr. Dorsey managed his Southern California team versus his Midwest team?

In Southern California, he was the superstar salesman hiding behind a manager title, solving problems himself. In the Midwest, he started teaching people how to fish, listening twice as much as he talked, and letting them do the work with support rather than solving it for them.

How did Dr. Dorsey rank on the Air Force staff sergeant exam his first time taking it?

He placed 19th out of hundreds of thousands of people Air Force-wide on his first attempt, which led to being called in front of the base commander to share his study methods with people who had taken the test up to seven times.

What does Dr. Dorsey say is required before someone can truly develop as a leader, beyond reading leadership books?

He emphasizes that reflection and self-awareness - understanding who you are - must come first; you can read every leadership book, but until you understand yourself, that knowledge won't translate to effective leadership.

What specific mistake did early-career Dr. Dorsey make that required him to change his management approach?

He got his high from being the superstar salesperson under the guise of being a manager, helping close deals and getting high-fives, which created a team dependent on his skill rather than a self-sufficient team.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

14 / 20

The episode contains several substantive ideas about leadership transitions, the distinction between teams and work groups, and the risks of unconscious competence, but much runtime is consumed by lengthy personal anecdotes and throat-clearing that could have been condensed. The core insights - teach people how to fish rather than catching for them, understand your starting point before seeking mentors, and the danger of becoming unconsciously competent - are valuable but somewhat familiar to experienced operators.

I didn't teach them how to fish. I caught the fish for them. That's not great leadership right there. That's building a lot of enabling bad behavior and building a lot of people who are dependent on your skill set.
People don't take the time to figure out their starting point, point, and oftentimes don't really even know where they want to go or if they do know where they want to go, they don't know why they want to go there.

Originality

12 / 20

While the unconscious competence framework and the teaching-to-fish metaphor are useful, they are well-established in management literature. The distinction between teams and work groups is standard organizational behavior theory. The guest offers competent synthesis but limited fresh or contrarian thinking; most frameworks discussed have circulated widely in leadership development circles.

work group, you got a bunch of individuals who report up to the same person, but they're not interdependent
teach people how to fish. When I moved into senior management, I made certain that the people that I promoted from sales into management were there for the right reasons.

Guest Caliber

16 / 20

Dr. Dorsey has genuine operational credibility: 40+ years leading at multiple organizational levels, turnaround expertise at Fortune 500/1000 companies, a doctorate in organizational behavior, service on five boards, and ongoing executive advisory work. He has actually done the thing at significant scale. However, he now operates primarily in advisory and board roles rather than leading core business functions, which slightly limits direct relevance to operational B2B founders and front-line leaders.

I ended up retiring in 2019, January of 2019. I was the executive vice president and global head of sales for this large company.
I got my doctorate in organizational change in leadership. And all my research was around the lack of gender and ethnic ethic diversity on corporate boards

Specificity & Evidence

13 / 20

The episode relies heavily on anecdotes rather than named examples, metrics, or data. Dorsey references taking over sales teams in LA and the Midwest and describes outcomes (21 months quota attainment in LA, hockey stick growth in Midwest) but provides no specific numbers, timelines, revenue figures, or measurable KPIs. His research on board diversity is mentioned but not detailed with findings. The lack of concrete evidence weakens operational utility.

took over a team in Los Angeles that's never hit his quota... in a 24 month period we hit our quota 21 months in a row
he congratulated me on uh, what was going on in the Midwest. And he said, Keith, I know you're a great leader because since you left Southern California their production has gone down.

Conversational Craft

13 / 20

The host asks solid opening questions and genuinely engages with tangential follow-ups (the team vs. work group discussion, the authenticity question), but the episode often devolves into long, uninterrupted monologues from Dorsey lasting 5 - 10 minutes. The host rarely pushes back, challenges claims, or asks for metrics and proof. Most follow-ups are affirmative or exploratory rather than investigative. The conversation feels more like a friendly mentoring session than a rigorous exploration of claims.

Walk me through how you got that badge.
But it isn't just having that policy that you don't need to do that or that I don't expect that. But you can't do it yourself either because of the sort of unintended consequences

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B74%
  • Speaker A26%

Most-used words

team33sales24leaders22back20started18leader18leadership17question17first16learn15career15brandon15board15care15didn14executive14

Episode notes

What’s the real difference between managing and leading? Most people think they know. Few actually do. Dr. Keith Dorsey breaks it down simply: management is execution, leadership is direction. But the implications go much deeper than that. In this episode, you’ll hear how leaders unintentionally hold their teams back, how culture shapes performance, and why clarity of role matters more than motivation. If you’re building a team - or trying to step into leadership - this will give you a clearer lens on what the job actually requires.

Full transcript

1h 8m

Transcribed and scored by The B2B Podcast Index.

Speaker A: How did you become an expert in fixing any teams? Walk me through how you got that badge.

Speaker B: I was a young dad, newly married, and we were broke. I went to this conference and I spent $500 on many different cassettes from many different sales gurus. My wife said, uh, you spent money we didn't have because you think you're going to learn more so that you can sell more. And I said, yes, I do. And I did. Whatever you're going to do, become a student of your profession. I started managing salespeop and I became a turnaround specialist. I, uh, would move my family from place to place, taking over the worst sales teams at the time. I would lift the hood, I would make the necessary tweaks and then move on to the next problem child. My career just continued to take off from there. I got my high from being this superstar salesperson. I was helping them close their sales. We were high fiving each other at the end of every cell and they were happy. Took a sabbatical. I'm in my 40s. I wanted to get a feel for who I wanted to be when I grew up. When I left, I realized I didn't teach them how to fish. I caught the fish for them. That's not great leadership right there. That's building a lot of enabling bad behavior and building a lot of people who are dependent on your skill set. I started teaching people how to fish. The way that you excel is to stop doing the thing you did in your old role and realize there are new things you're going to need to be good at in your new role.

Speaker A: One of my favorite subjects to talk about is team dynamics, leadership, and how all of that interrelates in business. What a treat. Today's conversation is Dr. Keith Dorsey. He's got a doctorate in organizational behavior, started his career in the Air force and spent 40 years at every level of every type of manager. Eventually became the one that everybody looked to to fix broken teams and to advise struggling leaders. One of the best in the world when it comes to what makes a great leader, what is leadership, and how to be one. You guys are going to love this one. Boundary breakers is brought to you by Carter and Clark. Dr. Dorsey, sincere thank you for joining us today. We are fortunate to have you. I'd love to hear a little bit about sort of your origin story, your background, you know, where you, where you grew up.

Speaker B: Great question, Brandon. And Brandon is the name of my middle son, as a matter of fact. So I will never forget your name.

Speaker A: Fantastic. Fantastic.

Speaker B: I. I grew up in the Washington D.C. area. And then, and I went to high school in the Pittsburgh area. Quite honestly, I went to a high school that all my family members from my grandfather uh, on graduated from the same school in a small town just south of Pittsburgh. And so we moved from Washington D.C. i and went to that same school. Then I jumped into the military from there I was in the Air Force. I actually enlisted in the Air Force the summer between my junior year of high school and senior year of high school. So I knew before my first day of my senior year which day I was leaving for basic training. And so that that was outstanding. I had a, a short career in the Air Force. I ended up serving a year longer than my original enlistment. But then I was hungry to actually because my career in the military, I got promoted below the zone. And I said if I can be this successful in this large corporation called the US Air Force, imagine what I can do in a actual corporation. And so I, I got out of the Air Force and I immediately went into sales. And in my second chapter I was a first a sales executive and then I got promoted into middle into and so I started managing sales people and I became a turnaround specialist within m this Fortune 1000 company. I will move my family from place to place taking over the worst sales teams at the time. And I would lift the hood and actually figured out whether or not they were having a people product or process issue or combination of the three. I will make the necessary tweaks and, and then move on to the next problem child. And I also incubated opportunities and sales teams within the organization. And we grew and I was all. I became a strategic growth expert and a turnaround specialist. I got promoted into senior management in the late 1990s and my career just continued to take off from there. After 17 years with that Fortune 1000 company, I took a sabbatical. Supposed to be a six to 12 month sabbatical. I'm in my 40s. I wanted to get a feel for, you know, who I wanted to be when I grew up. And uh, two months into that 6 to 12 month sabbatical, I was driving my wife absolutely crazy being at home. I was running 10 miles a day and, and she said, you gotta find something else. And she was right. And I went to work for, for what became a Fortune 500 company. And I started a brand new sales team with that Fortune 500 and grew that sales team. I started taking over troubled sales teams as well and turning those around similar to what I did in my first 17 years and I ended up retiring in 2019, January of 2019. I was the executive vice president and global head of sales for this large company. And I entered my third chapter, Brandon, which I call my portfolio career of doing a little bit of this, a little bit of that. I do executive advisory work. I started serving on boards. Today I serve on five corporate boards or uh, five boards, two private companies, SAS company boards, one municipality where I with their financial advisory commission of my city. And I serve on um, Pepperdine University's business school board and then one non nonprofit which is the Pacific Crest Trail Association. That's that trail that goes from Mexico to Canada through three states. And so those are the five boards that I serve on during this period of time over the last seven years. I went back to school. I went to the University of Southern California. I got my doctorate in organizational change in leadership. And all my research was around the lack of gender and ethnic ethic diversity on corporate boards, corporate board refreshment, corporate board governance and uh, and once I got my degree there and uh, my doctorate, a global executive search firm found me and said Keith, with your strategic growth experience coupled with your research around corporate governance and corporate board refreshment, we think you would be excellent. And professional search. It wasn't anything that was on my bucket list but after many conversations I actually ended up going that direction. I became a managing partner with them and I also led their U.S. practice of um, um, CEO and board services. And in addition to my board service work and my executive advisory work. So this portfolio career started to take off like you wouldn't believe. And what was supposed to be a little bit of this and a little bit of that became a lot of this and a lot of that. And I was also writing for Harvard Business Review, mit, Sloan Management, Forbes, FAST Company directors and boards and others. And I was wrapping up my book that came from out of my dissertation called the Boardroom Journey. And all of those things made up this third chapter that I'm m currently in called you know, you know, my portfolio career. And since then I stepped back from my duties and professional search. No, um, longer a managing partner. I'm a senior advisor with them still with that same CEO and boy board services practice. But I started my own company called Boardroom Journey based off of my book where I have two remits. I help businesses or boards really analyze where they are and where they're trying to go and do they have the right makeup or composition of their board that to have the right functional expertise and and competencies on their board. Board to best align with their, their, uh, strategic mission moving forward then. So that's one remit and the other is I work with executives and senior government officials that take off their, I'm going to say consciously competent executive hat and learn how to intentionally put on their consciously competent governance hat and really show up differently when they're making that career move from being an executive to actually being a board member. Because what got you here won't get you there. So that gives you a, uh, update as to, you know, throughout my adult career, the three chapters that I have actually had, you know, in the military and corporate America, and now in this port portfolio career. And it's been absolutely outstanding.

Speaker A: Yeah. Gosh, well, congratulations. What a career. And that was a great synopsis. I would love to come back to your comments, some of your comments about board members and the difference between being an executive and what's expected in the boardroom. But I really, I want to go back and dig a little bit on, I mean, I'm interested in this role where you would go and just sort of walk in and be introduced to a sales team and somebody to say, okay, fix it. So first of all, how did you become, I'll call it an expert. How did you become an expert in fixing any teams? And I'm just, uh, I'm fascinated. Just walk me through sort of how you, how you got that badge.

Speaker B: You know, it's interesting. I believe in becoming a student, whatever you're going to do, become a student of your profession and, and really, you know, try to learn, have that learning mindset and realize that there's really no finish line, that it's a dynamic world that we live in and because of that we should continue to learn as m much as we possibly can. And, and with that sort of mindset, I remember being a young mid 20 year old year old. Well, I even started in, in the military. I, I told you I got promoted below the zone in the air Force. And because I took that whole process very seriously. And the first time I tested for my non commissioned officer rank at that time, I actually passed that test. And I remember being called into the base commander. I was stationed in the United Kingdom, him. And um, when you're a lonely sergeant, you don't get called into the base commander's office. We have 5,000, you know, airmen on that base. And I went into the office and they said, you got to report to the base commander. Okay. And I went in and I met up with, you know, his chief of staff. And she led me into this large conference room. I walked in the conference room, Brandon, and there were people, long conference table, people lined up all against the wall, standing room only people sitting around the table. And the base commander at the head of the table, he said, uh, you know, Sergeant Dorsey, I called you in one. I wanted to congratulate you. You passed your staff sergeant's examination. You, out of the, you know, hundreds of thousands of people that took the test, you were number 19 in the air Force, and it was your first time taking the test. And I, I said, well, that's outstanding. Thank you for letting me know. And he said, and the people in this room have taken the test many times, some up to seven times. You can only take it once a year. And, and he said that, um, I want you to, to tell the people what you did in order to pass the test. There was no warning, there was no nothing. I was just called in and all these people were in this room and I, I shared, I share my secrets to success with that. I took those secrets to success over to corporate America when I got out of the Air Force. And some of the things I talked about was becoming a student of your profession. I learned how to take, take tests. I read books on how to take tests, and then I studied all the material they gave us to do well on that test. So it wasn't only learning the information, it was also learning how to actually take tests. But nevertheless, I, and, and so that's what I took into corporate America. So when I became a, a salesperson in corporate America, I, the first year I ended up, it was the first year of a brand new division at this Fortune 1000. And there were 50 new salespeople. And these 50 salespeople, I was one of the 50 that year. Only two people hit quota that year out of the 50 in our inaugural year. And, and I actually smashed the quota year. And so they called me up to Rochester, uh, New York, where we were headquartered. And it was at the same time, I don't know if you remember this, Brandon, of uh, the Clarence Thomas Anita Hill hearings.

Speaker A: Oh yeah.

Speaker B: Remember walking into this large conference room yet again, and there was this table in front of the, this U of executives. And, and, and I sat at this table by myself. And for six hours they grilled me as to, they started off by saying, keith, congratulations on smashing the quota. And uh, and you were one of two people that hit quota this year. Clearly we got the quota wrong. But what we want do to hear what you did in order to get there. And so I sat there and what made me mention Clarence Thomas, Anita Hill. I remember those hearings with, with them just sitting and being grilled by many people. That's how I felt for six hours being grill. But I shared with them what I did. And once again, becoming a student of my profession, uh, I was a young dad, got newly married, and, and we were broke. But I, I went to this conference that cost 500. That cost a good percentage of my, uh, good. A bit of money. And I spent $500 on many different cassettes. Wow. From many different sales gurus. And, and I came home that evening and my wife said, what do you have here? I have stacks of cassettes. And I said, I listened to these people on stage. I love what they had to say. Um, and I want to study what they did. And she said, you went there, you spent money we didn't have because you think you're going to learn more so that you could sell more. And I said, I do. And I did. And when I went to a week's training with this Fortune 1000 company, they taught me how to sell what they wanted me to sell. But I took all those learnings from those many different cassettes back then, and I incorporated that into what I learned from the company. And I did it my way. And I sat there in front of them and I explained, I say, you all taught me to do this, but I learned from these cassettes to ask questions these ways, and to care more about helping them than telling them how great we are. And they said, tell us more. Give me examples, and, and so on and so forth. We did this for six hours. And when I was done, they said, this has been helpful. You, we are immediately promoting you to a field sales management position. And we want you to teach people in Washington, dc, Mid Atlantic area, uh, Philadelphia, and Cherry Hill, New Jersey, how to do what you just told us. And that was the beginning of my turnaround career. You asked the question, what would I do? Well, I would go into a city, I would sit back, and the saying is, God gave you two airs and one mouth for a reason. And I would listen twice as much as I would talk and really hear where they are, what they're doing, why they're doing it. And, and then I would tell them m. What their job actually is. Then I would show them how to do the job. And then I would let them go out there and do it, listen and, and, and then debrief with them after that. Uh, and so eventually what it became after multiple Days of being in the field and curbside critiquing. What it became was tell them what their job is, show them what their job is and how to do their job, and then spend the bulk of my time after that removing obstacles by letting them do what they needed to do. And, and then I would teach them. If I chime in, think about what was said before I chimed in, think about what was said after I chimed in and begin to emulate that. And next time I'm going to expect you to do that, and I'm going to shut up. And so the, and, and that's how we will begin to tweak the things that were necessary in order to be successful. And, uh, I would just do that location after location after location. But as I can't continue to get. As I got promoted, I would just do it at a higher level, teaching the managers, of the managers how to do the things that they needed to do without doing someone else's job. So I'll pause right there. And hopefully that lengthy story helped.

Speaker A: Yeah, it does. And you know, highlights something, uh, that. That's very, very fascinating to me that I spend a lot of time thinking about, you know, I, My first leadership experiences were, you know, growing up in sports, and then I graduated from the Citadel. I didn't, I did not take a commission. Uh, they wouldn't let me. But the, you know, I learned so much about leadership from that military education. And one of the things that I learned while there that I still run into as a CEO today, that I don't think is. Is talked about enough or recognized enough or discussed enough is, is that it's the point that you, that you made just there with your last statement about what you had to do, that there's a, in my opinion, a huge difference between leading a team that's, you know, trying to execute something or sell or perform or, or mechanics, whatever, like leading a team, a frontline team, compared to leading a group of other leaders who, who then either they have their own team or they have leaders below them that have their own team. And I'm curious, what, what about, you know, because in your example, right. It's not. You can't just tell the sales leaders, oh, you have to go out and you got to buy cassettes and you got to work harder and you got to be a student, right? Because they're like, well, but I'm not selling. Right. So I'm curious about the, uh, sort of the leap or the step between coaching or being a leader on a team versus Leading other leaders and if you ran into any challenges there, what the differences are.

Speaker B: Another great question, Brandon. And um, you know, there are several points that I can make around that and I can give you an example. One was learning how to help people by not doing it. And let me back up for a little bit. I took over a team in Los Angeles that's never hit his quota whether it was their monthly monthly quota and def. Of course because they hit their monthly quota here and there but never hit a quarter and never hit their annual quota. And so I took over that team and, and in a 24 month period we hit our quota 21 months in a row and, and we were high fiving each other, just loving life. And they asked me to take over a team in the mid and the Chicago area and it was Chicago, Milwaukee, Minneapolis. And when I moved my family from Southern California to the Midwest, I, I remember how the things I had to do with this new team in the Midwest and I remember going to a huge national meeting and the executive vice president of sales made me stand up in this meeting and he congratulated me on uh, what was going on in the Midwest. And he said, Keith, I know you're a great leader because since you left Southern California their production has gone down. And what you're doing in the Midwest there is a hockey stick. And so I know you're, you're the key component to this success because when you were in the Southern California was successful, now you're in the Midwest and the successful. And I stood uh, up and I apologized to the EVP and said what I'm about to say may disappoint you. I appreciate the praise that you're giving me but I learned something that uh, I did in Southern California that I'm no longer doing in the Midwest. The reason why Southern California is not performing in my absence is because I got my high from being this superstar salesperson under the guise of being the manager and I left. From being a number one salesperson to being this Phil's sales manager, to being this district sales manager now in Southern California. And I was helping them close their cells and we were high fiving each other at the end of every cell and they were happy and we were performing. When I left I realized I didn't teach them how to fish. I caught the fish for them. And that's not great leadership right there. That's building a lot of uh, enabling bad behavior and building a lot of people who are dependent on your skill set. And what I immediately changed in the Midwest was that I started teaching people how to fish. And I was the problem. It was my ego that caused that situation in Southern California because I needed to be the person that wore the cape. You know, I came in here, I come to save the day, you know, and that was good. And I'm getting high five. Everybody's happy, everyone's making money. But I, I didn't create something that was sustainable. And, and it died when I was there. It went downhill. It didn't die, but it didn't perform at the level that it should have. And that's what I changed. So one of the things I learned in middle management was to teach people how to fish. When I moved into senior management, I made certain that the people that I promoted from sales into management were there for the right reasons. I wasn't just promoting people who needed to be a hero. I was promoting people who wanted to help, who wanted to teach, who wanted to lead. And, and so that was step number one. Then step number two was teaching people, people to do the things they need to do. To use their ears twice as often as they use their mouth to gather data and do something with the data, Meet people where they are and help them progress, Allow people to fail, allow people to scrape their knees but have bandages ready to help them, help them get back up, help them not get imposter syndrome, but realize that failure was a mechanism that can propel their growth. And that's where I started teaching leaders of leaders to do. And, uh, let them know no differently what than what I said about helping executives take off their unconsciously competent executive hat and then put on a consciously competent governance hat, because what got them there won't get them there. I had to do the same with middle managers and senior managers to get them to realize their new role that they're going in. That the way that you excel is to stop doing the things you did in your old role and realize there are new things you're going to need to be good at in your new role. And don't just try to be a superstar in your old role under the guise of your new role. And so that was a process. And hopefully those examples, Brandon helps.

Speaker A: Yeah, absolutely. Absolutely. And you know, you're not giving yourself, I don't think, enough credit about, you know, how you were so influential on some of those teams. And I know that a lot of it you're, you're shortcutting for the, for the purpose of the story. But, you know, it's interesting to me that probably in every Business across the world, you run into people who desperately want and have the desire to be a good leader, some even to be a great leader. And you can go on Amazon.com and type in leadership and buy, you know, you were talking about $500 worth of cassettes. You could buy every book by, you know, the, the whoever they consider to be that their 10 ideal leaders. Um, and they all will tell you how to do it right. But it isn't like a diet or a math equation where here are the four things. If you just do these, then you're now a great leader. Why? Why do you think that is? Why? The why? The disconnect between the people that want it and the unbelievable amount of instruction that's out there. But yet the common disconnect I share

Speaker B: with people that I coach who are making that transition from being an executive to being an independent director on a corporate board, a paid board, uh, I share with them. Step number one is you have to reflect. You can learn as much as you want to learn about corporate governance and you really understand the job of a board member. You could read up on all these things. But until you understand who you are, how you show up, what your secret sauce actually is, what are your superpowers, the value prop that you bring to a scenario, and you find your sweet spot. Until you are able to do those things, it doesn't matter what you learn. Because you're going to learn something that worked for someone else, and because they said it worked for them, they're going to teach you how to make it work for you. But it may be apples and oranges, it may be asking you, in an example, you know, on, uh, the sales side, to pick up the phone and cold call everybody, or to go to mixers and hand out your business card to everybody, where you are absolutely horrific at small talk. Well, I don't care how much it worked for the person that wrote the book or the mentor that told you to do it. You, if you're horrific at small talking, you haven't solved that. It's never going to work for you. So those four or seven points that the author or speaker you know, professed may not be a great fit for you until you understand how, what makes you you, what are your strengths? What are your weaknesses? Which strengths do you want, want to double down on? Which weaknesses do you want to ignore and try not to ever do a job that incorporates those weaknesses or what weaknesses do you want to enhance, improve on and begin to figure out those things, Figure out what brings you Joy. And when you spent the time to reflect on those things and actually truly understand what makes you tick, then you could figure out what type of book, what type of leader is going to be a good fit for you, and is it just one person? Brandon, A lot of people go out and they seek a mentor, and they think this mentor is going to be their panacea for all their ailments. And what I, you know, some of the research that, uh, I've done, one of the big things that came from out of the research was, you know, several people said they had many mentors. And I said, tell me more. And I said, how many mentors do you need? Said, it depends on the things you want to work on. I said, tell me more. And, and basically what they were saying is, if public speaking is something I need help on, I don't seek a mentor that is great at everything, if that even exists. I seek a mentor that can help me with public speaking. If finance and financial acumen is something I want to work on, I find a different mentor that's strong from a financial acumen standpoint. If writing effective appraisals is important for my next promotion, I find someone that excels there. And so, but you have to know where you are and ultimately where you would like to go, and then find the, the books, the mentors, the sponsors and allies or whatever that might be able to help shore up those areas. But if you don't know where you are, how do you know where, how to get to where you want to go? And so I think that's the difference. Brandon People don't take the time to figure out their starting point, point, and oftentimes don't really even know where they want to go or if they do know where they want to go, they don't know why they want to go there. So they may be going somewhere that isn't a good fit for them and then wondering why they hit so many roadblocks around along the way.

Speaker A: Do you, do you think that based on your experience, do you think that anybody can be a great leader or do you feel like, in other words, is this, is it a hundred percent learned behavior or is it, is there some sort of prerequisite that of tools and, you know, mental capacity, emotional intelligence? I mean, is there some sort of natural or, uh, nature that has to be there?

Speaker B: I think there's a combination of things that people have to have in order to be a great leader. There are leaders out there that excel in certain parts of their job and extremely are uh, fail in other parts. They may not ever be a great leader, but they're still a leader. So can leadership be taught? In my opinion, yes. I think those unicorns that we call great leaders innately bring components from an EQ standpoint that makes them great leaders that they may double down on and they focus on their strengths and they become even greater. And then there are areas that they're weaker in that need improvement. They may double down on those to get better up to a point, and then they're fine with where they stand.

Speaker A: Yeah.

Speaker B: You know, I, I talk about Shaquille o', Neal, who is great, you know, ah, up close and could drive to the rim, but his foul shots were horrific and people said, why doesn't he just practice the foul shot? Or should he just double down and focus on his strengths and become even better? And I, uh, think great leaders realize where their strengths are and they double down and they continue to improve in those areas. They look at the areas that need to be shored up to a certain degree and, and then there are some areas that they say, um, I'm not even going to bother. Like that foul shot.

Speaker A: Yeah.

Speaker B: I'm trying with a bother because in the whole scheme of things, the return on time and investment isn't really there. But if I double down here, the return is going to be threefold. And ah, I think great leaders are able to do that. So in my opinion. Can leadership be taught? Absolutely. The military has proven that and many other world, you know, industries, uh, have proven, and vocations have proven that. But great leaders do bring some innate things to the table. And I think the saying there is people don't care how much you know until they know how much you care. And great leaders do care and they know it well.

Speaker A: So I mean, you have a lifetime of experience, you have a doctorate degree. I mean, you're, you, you place leaders on boards and with companies. Are there. You mentioned certain EQ components. The great, the great ones have, have you been able to identify, you know, common threads? What, what are the, what are those EQ components that the greatest of the great leaders bring?

Speaker B: I. Going back to. They care.

Speaker A: Yeah.

Speaker B: I, I really think caring is important, not only professionally, but personally. Those that truly care about someone's personal motivations as well as their professional motivations, and they're in a leadership role. Those people that report up to that individual typically would do anything for them.

Speaker A: Yeah.

Speaker B: Because they know, they care. My mantra was if I would let people, you know, the first 15 minutes of every one on one I spent my time really just getting to the check in from them. Tell me what's going on. Uh, you know, last time we talked about, you were talking about the bar mitzvah for your kid. Tell me about that. How did it turn out? And then eventually 10 to 15 minutes later we start to get into business. But I genuinely care and they know that. And, and so that's one component recognizing in our culture that we're workaholics. And people who only care about the professional side of things may expect you to work like crazy 24 7. I know that's impossible, but you get my drift. And on the weekends and everything else. Well, I had a policy that by 6pm on Friday to 6:30am on Monday, I sent no emails whatsoever. I may have crafted something on my own, but I didn't hit send until then because I didn't want my direct reports checking their email box or BlackBerry back in the day and different things like that. I wanted them to rejuvenate throughout the weekend so they came back strong on Monday. And I figure if they didn't have to look over their shoulder on the weekend wondering if I needed something from them, then for their direct reports they would do the same. And I would tell them this isn't, this is intentional and I want them to do the same. And for their direct reports, those people to report to them, I wanted to make certain they weren't sending messages, messages out and, and to create this subculture. And because of that subculture, our engagement scores were often higher in my divisions than the companies because people were able to relax and rejuvenate. And uh, you know, I think those components are, are important from a leadership standpoint.

Speaker A: You know, the I, I learned that lesson the hard way early in my career. The. I'll never forget it. I think about it often actually. And so it's funny that, or it's interesting that you bring that up. I had a. Somebody on my team say bring up the. Well, emailing or, or staying in touch over on the weekends or late. For me it was, it wasn't as much on the weekends as more as like I would send it, I would be thinking about something or I'd send an email at 9 or 10 o' clock at night and, and I said what do you mean? I don't, I would never expect any of you guys to send an email after, you know, 6:00pm Right. And they said yeah, but you do it. And so you're leading by example, right? Yes. So I, I had to check myself and have a similar policy now for that very reason. Right. I would, uh, Like I said, I would never expect anybody to do it. But it isn't just having that policy that you don't need to do that or that I don't expect that. But you can't do it yourself either because of the sort of unintended consequences or the appearance. Right?

Speaker B: Absolutely. Is a saying, do as I say, not as I do. I remember parents with the cigarette in their hands.

Speaker A: Yeah. Ah, smoking. Smoking kills.

Speaker B: Yeah. Do as I say, not as I do. But I think as leaders, we have to lead by example. I remember in the early mid-90s, bragging about the fact that I worked 70 hours a week. It was a badge of honor that I worked 70 hours a week. That was a cool thing to do. Wall street movie was out. You know, you just drive and you work your tail off. And I was bragging and someone sat me down, said, keith, I know you talk a lot about the fact that you work 70 hours a week. If you're working that many hours, is your job beyond you? Oh, wow. Wow. I never really thought about it that way, but everyone around me worked that much. My boss worked that much. And so she was leading by example. And I wanted to be like her. And so I did it. And the people working for me did it. And that's when I learned. And I immediately, like, almost overnight, went from 70 hours to 50 hours almost overnight and was better. And that's when I. I, uh, learned the power of rejuvenation and the beauty of that. The Europeans have it right. You know, we have a ways to go in our society here in the US Even to this day.

Speaker A: Agreed. Agreed. You know, uh, something that. That may triggered or I was related to hearing your answer about wanting to be like your boss or that you had other people wanting to be like their boss. Something that I find all the time is. And we. Throughout this, throughout, uh, most of your answers, you've talked about finding mentors or finding, you know, other people can coach you, other people can teach you. I think sometimes I'm curious of your thoughts on this. I think sometimes, while that's great because you get to learn from other people, it breeds this mentality or. Or thought process that you gotta. You gotta act like that person or you gotta copy that personality or that thought pattern. Uh, and what, what's so. What I think is so counterproductive about that is authenticity I found in being genuine is one of the most powerful traits in a great leader. And if you're imitating somebody else. It is, like, definitionally impossible to be authentic, right? Yes. What does that square with your experience and your expertise?

Speaker B: It really does. And that's where you got to be careful about your cultures and your subcultures that you create. And, you know, as a healthy culture, we had a saying, you know, we would recruit people that were a good fit. And, you know, when we're interviewing people, we've measured three areas. Attitude, commitment, and fit. Fit being the most difficult and the most important part. But you got to make certain that you define what fit is. And. And fit, in our case, mistakenly, was act like us, be like us. And in those scenarios, you really don't get authentic people. You get people who you encourage and compensate them to do things only your way, like you. And. And you end up missing a true opportunity for growth because you got a bunch of people doing it your way without being. Bringing in fresh ideas in this dynamic world based on their lived experiences. And we end up, you know, running into reputational issues, risk issues. We don't properly disrupt ourselves in those scenarios because we're all in this group think, sort of mindset. So fit is important, attitude's important, commitment's important, fit important. But make certain you define what fit is. And fit might be around a value system, not emulating people, uh, the way we meant it.

Speaker A: Yeah, yeah. But, you know, the. As. As I asked that question, I realized you. I think you actually answered it probably earlier in our discussion, because, you know, I asked the question, well, look, there's essentially 5,000, 30,000 books on Amazon that'll tell you how to be a great leader. Why can't everyone just do that? And your response was, well, they don't, because they got to figure out where they are, right?

Speaker B: Yes.

Speaker A: And so, you know, to your. To highlight that or to underline your point just because, yeah, that person may have been a great leader, and they can tell you all about how they did it.

Speaker B: They did it. Yes.

Speaker A: So how do you coach people who they. They. You know, we talk about, when hiring, people get it. Do they get it? Do they want it? And do they have the capacity for it? Like, so somebody that. That is. That is maybe early in their career and wants to be. They really, really. I mean, I don't mean want. Like, yeah, it would be nice. I mean, they are on fire for it. What. What do you. How do you coach somebody like that? Given what seems like you, uh, know all these crazy dichotomies out there, you got to find yours. But this is what, you know, this is how so? And so Jack Welch did it or whatever.

Speaker B: Yeah, yeah. And when you mean they're on fire for their next promotion, they're, um, on fire for leadership. They're on, yeah.

Speaker A: And I mean genuinely, like they want to be able to impact and influence even their peers or colleagues or they want to be a positive good leader and influence, but they don't know how, but, but they have all these books that supposedly tell them how, like how do you navigate all that?

Speaker B: And so what I would do in those scenarios is, you know, become more interested than interesting. Because in these coaching scenarios, people try to ask you a bunch of questions, uh, being the mentor or the coach, and they, they want to hear your story because they want to get to where you are and that's being more easy interesting than interested. If we pause and be more interested than interesting, we're going to turn it around and ask them more questions. Tell me about a time that you worked for someone and it just brought you joy to work for that person. What was it about them that made you wake up the first time the alarm clock went off instead of hitting the snooze button five times and then conversely, tell me about a time where you did hit the snooze button of five times. What was going on in your world? What were you experiencing, what did you like, what didn't you like and why? I'm forcing people to reflect, to get a feel for three things. Where they were, where they are and where they would like to go, and why. And, and when you can get people to really start to think and, and what you're doing is priming the pump by being interested in asking thought provoking questions and not just questions and moving on to the next one on the list, but listening to those answers, their answers, and asking a second level question, a third level question, a fourth level question, to dig deep. And then you'll find people will start to look up and they're like, huh, that's a great question. And then they're thinking about their answer and they're learning about themselves. And I think that's the difference is to really get people to understand who they are and where they like to go and why they would like to go there. Are you trying to go there because your parents told you that's what's next? Are you trying to go there because your mentor went there? But when you ask that second, third and fourth level question, you get past those things and they can begin to realize, I only wanted to be a lawyer because my mother talked to me about it for 10 of my 18 years at home, and I really don't like it. So I understand. You got your jd. What do you want to do about that now? What do you like? I don't know.

Speaker A: I gotta stop you. I have to. I have to stop you there because you're not going to believe this. You're not going to believe me when I tell you. But you just told my story.

Speaker B: Wow. Wow.

Speaker A: Really?

Speaker B: I've heard these stories before. I've lived them myself. And it takes guts and intestinal fortitude to say pause and, and, and let's re. Evaluate.

Speaker A: Yeah, it's. Well, yeah, I mean, I wouldn't change anything, but I just, I would love to put that on repeat and blast it from the top of every mountain. I think if you could get inside the, the hearts and minds of all the adults in the US and, and ask, you know, evaluate where they are and really, really find out why they're there, I think we would be astonished by how much outside influence, whether it be parents or society or peer pressure, had to do with getting where they are as opposed to what they really enjoy and what they want to do.

Speaker B: And life's no dress rehearsal, Brandon. You know, tomorrow's not promised and you can't relive yesterday. And so, uh, you know, people get this wrong. They often say it's time to make a 360. No, 360 will put you right back where you are right now. It's time to do a 180, though, and, and, you know, no better time than the present. I, uh, don't care if you're 63, do it. Tomorrow's not promise. If there's something that's going to bring you joy, first of all, figure out whatever that is and then go do something about it.

Speaker A: That's inspiring. It's inspiring. I just got a couple more questions. This happens every time. The. I get somebody fascinating on here and then all of a sudden like an hour goes by and I, and I haven't even, you know, feel like I haven't even gotten to talk about half the things I want to talk about. But the, you know, the, we, we focused a lot on the. What make, you know, the individual.

Speaker B: Right.

Speaker A: Like what, what. How to become a great leader from an individual perspective. I'm also very fascinated in sort of group dynamic. And I, every time I think about this, I think about the Boston Red Red Sox World Series winning team that, where I think Johnny Damon was one of sort of the media darlings on that. And uh, they called themselves a bunch of idiots or whatever. Right. Like they're point was we don't have any world class superstars. You know, we're a bunch of like average players, but we play really well together. Yeah. And that, that creates something really special that lets us go collectively to a level that others can't. What? You know, I mean, I think this is the. I'm going to ask you an impossible question because if you like, this is sort of the genesis qua of the whole, the whole deal. But what is it that, what is that X factor on or in a team that just sort of catapults certain groups to the stratosphere where others just can't for the life of them get halfway there.

Speaker B: I love that question. I remember when I first started my MBA program at Pepperdine University and was a president and key executive MBA program. And in order to get into that program you had to be a key executive either at your own company or, or some other organization. So it was like the executive MBA on steroids.

Speaker A: Oh, wow.

Speaker B: And the average age of each student in your cohort. In the cohort was 45. So. And instead of reviewing Harvard, you know, case studies with the NDA almost, we were reviewing our own organizations that we let. And then, um, and the discussions were amazing. But one of the first things we learned in the behavioral science track was teams. And in our society we use teams probably incorrectly. And so the question that the professor asked, give me an example of a team, uh, at work, one of your teams. You all are saying my team this, my team that. But is it really a team or is it a work group? And so work group, you got a bunch of individuals who report up to the same person, but they're not interdependent, they're not behaving in an interdependency sort of way. That's a work group. Whereas a team truly as, uh, they are interdependent. They understand each person's role and they make certain that everyone understands and that they know the value of doing what they said they were going to do, when they said they were going to do it, and how they said they were going to do it, and how that if they alter that in any way impacts everyone else. So when you think about Indiana University's, you know, national championship that they just won in football, perfect. They did have a star Heisman Trophy winner. But would he have even won the Heisman Trophy if the team wasn't behaving like a team? You know, and, and so I think your Boston, uh, example, Red Sox example is the same thing when people care about each other to the point where they understand their personal motivations, each other's and professional motivations and they really care about helping each other in those areas and they understand what they're role is in the company at every level. And that answering and dealing with that customer service issue impacts this in so many different ways. I'm um, not just reading a script. It makes a difference when everyone understands their role and understands the people around them, their personal and professional motivations. It's only then that you begin to put a team together and otherwise it might just be a functioning or non functioning work group.

Speaker A: Yeah.

Speaker B: And that's even though we think it's synonymous. It's not. So that's my response to your question. How does that resonate with you?

Speaker A: Brandon? I think that's unbelievably well said. I mean I'm still reflecting on what I think is a very, very insightful comment that maybe we're misusing team. We're very, very frequently misusing team. Because I mean, I suppose that's exactly right. Because if there isn't, I mean if there's only sort of common measurements like uh, if, if you're on a work team and you're only measured by how well you, you do and there isn't a common way for a team to, to, to win, then I guess it could be, it should be considered a work group. A work group? Yeah. And you'll get broke.

Speaker B: I mean it doesn't mean it's bad, but it's not a team.

Speaker A: Right, right.

Speaker B: Can you get different levels and get to a, A uh, different level of growth and expertise and if you turn it into a team and what will it take?

Speaker A: Yeah.

Speaker B: And, and people support what they help create.

Speaker A: Yes.

Speaker B: And so instead of the leader trying to come up with all the answers, his or herself, to get that work group together and say here's where we are aspirationally, where do you think we can go? And then put them all up there. There are no bad answers. And what do you think we need to do differently as a work group that has an ah, aspiration of being the team in order to get there, what do we need to do and how can we go about doing it? And sometimes some of the cost cutting measures that we put in place as leaders, actually the unintended consequence is you may be taking what is a team and unintendedly moving them to a work group because you got them so single mindedly focused around one Metrics, and they don't even understand how that one metric applies to everything else. And that what we thought was great leadership and direction ends up unintentionally creating some other issues within organization.

Speaker A: Good stuff. I love it. Well, so, last question, I suppose I wish I had had time for a whole lot more. I have to have you back.

Speaker B: Happy to be back.

Speaker A: Brandon. Yeah. Management versus leadership.

Speaker B: Do you.

Speaker A: Do you think those are different? And if so, how?

Speaker B: Uh, I do. Management, in my opinion, is the ability to understand what the task is and really understand how to actually do the task and then the executable things that needs to be done and how to hold people accountable to doing those things. So you reverse engineer and then you execute and you hold each other accountable. You know, I put that under the management side of things, that leadership is more around the vision and, uh, the vision of it all. Here's where we are, and from a vision standpoint, here's how, where we're going. And that via our management is around the how, which is the mission. This is how we're going to get there via our great execution. But here's ultimately where we're going. And I forget which author and speaker said this. I, uh, think it may have been Kim Blanchard. He said, if you're out and you're leading and you stop and turn around and no one's there, you're just. No one's behind you. You're just taking a walk, you know? And, um, so leading is where you have that vision and you surround yourself with the right managers, the right people that execute, and you look behind you and they're still there because they believe in your vision. That's leadership.

Speaker A: Yeah.

Speaker B: Yeah.

Speaker A: I love that. I. I don't. I don't. I have no idea if there's a right. I mean, if there's an answer to that question. I was just curious what sort of. What, what I get a chance to peek into your mind. It's a lucky day for me. So I'm just curious.

Speaker B: That's the way I think about it. Yeah, that's the way I think about it.

Speaker A: That's. That's fantastic. Well, Dr. Keith Dorsey, I can't tell you how much I appreciate you taking an hour out of your day to spend time with us at Boundary Breakers. And I took a note here about halfway through that I've got to have you come back for round two. So hopefully it's not as far out as we had to schedule this one.

Speaker B: You're a hard person to sit down with. Oh, Shoot, that's a compliment to you.

Speaker A: Well, I appreciate that.

Speaker B: 11 months. This was booked 11 months ago.

Speaker A: Well, had I been able to get a glimpse into the future for, you know, what these things have been like, I would have moved you way up the list. Well, thank you. I mean, I say that because the. A lot of your. What you've been successful in and what you know about and your expertise and knowledge are things that I am, um, intensely curious about, and there's a whole bunch of questions about.

Speaker B: So I truly look forward to coming back. You let me know when Brandon and I'll be here. Uh, fantastic conversation. This has been just fun to reflect back to that. Reflecting. Reflect on some of these things that we unfortunately sometimes think are table stakes. And in the osmosis, just by talking about it again, I feel rejuvenated and stronger.

Speaker A: That's a really good point. You know, I mean, I suppose that the. It's almost counterproductive. If you're around a group of great leaders or people that are. That you feel like are really talented, then I suppose that the natural tendency is to feel like all of these, uh, you know, lessons that we've all learned or experiences we've all had are just sort of cost of doing or table stakes, like you said, as opposed to really getting to celebrate how, uh, meaningful, whether it be what it was like in the Air Force to what it was like your first, you know, first couple of roles.

Speaker B: So I, I got one more example, if you don't want.

Speaker A: Please, please.

Speaker B: You know, just by talking about these things, it, it forces you to. To become consciously competent. I. I would have my top sales executives or top sales leaders eventually start to fail. And I'm wondering why they're failing. And it's because they became so unconsciously competent that they unintentionally stopped doing some of the things that got them to that unconsciously competent state where they are peak performers and they. It, uh. I liking it. Brandon, to you driven home on the same commute for several years in a row, and it's scary now because you pulled in your garage, and I don't care how much you think about it, you can't remember the last 15 minutes of your commute. That's dangerous. That's dangerous. And why can't you remember the last 15 minutes of your commute? It's because you're unconsciously competent. And sometimes we need someone or something, hopefully in a positive way and not a negative way, like a car crash. The move us from that unconsciously competent state back to A consciously competent state. And what I found from my top salespeople and top sales leaders was when they started to fail is because they stopped asking the right questions. They knew the answers that their prospects or their clients or their direct reports were going to give, so they stopped asking. They just started telling. And when you tell people you can't teach the student until the student's ready to learn. And so it's the question whether that's the prospect, the client, or the direct report that when a person doesn't have the answer and they realize they don't have the answer, now the student's ready to learn. But if, uh, you just tell them, like your child, your. Your kid, you just tell them, Tell them, Tell them you can't teach the student until student's ready to learn. And because of that, they became so unconsciously competent, they stopped asking questions and they started telling. By forcing them to go back to that consciously competent state, they stopped telling and they started asking. And the student was ready to learn because they realized they didn't have the answer. Now tell. Now tell me my cup is no longer full. My cup is now empty and can take the knowledge you would like to give me. But if you just are telling someone all the time and their cup is already full, they think it's full. What you're telling them is just spilling over onto the ground. And they didn't get any of it. Yeah, I think that's the big difference. And in these situations, you emptied my cup. By getting me to reflect and think about things to the point via osmosis, I was ready to learn again and move from unconscious to conscious. And that, I think, is the secret to knowing how to regulate and help people as a leader. Sometimes you gotta scare them back into the conscious state or. Or remind them, because unconsciously competent seems like a great thing. But it might not be if you can't remember the last 15 minutes.

Speaker A: Yeah, yeah. Gosh, I'm gonna have to think about that. That.

Speaker B: That.

Speaker A: That's. There's a lot of layers to that, which I appreciate. I appreciate the gift. That's a gift. The pearl.

Speaker B: My pleasure. Just something I thought about because we don't think about that being a dangerous situation. But if you can't remember the last 15 minutes of your commute, you might be too much on autopilot. Right.

Speaker A: That was the word that kept coming to my mind was autopilot. And yeah, it's also, you know, where a lot of the mistakes probably happened. Right. Was where there's people let their guard down. They're not thinking. So, uh, that's a great one for the. For, uh, both myself and the audience to. To leave so they could. We can all reflect on it. So. You got it, Dr. Dorsey. Thanks again. I really, really appreciate it. I hope you have a great rest of the week and a, uh, great weekend. And we'll talk soon to schedule round two.

Speaker B: Likewise, Brandon. Thank you.

Speaker A: All right, take care. Don't forget, everybody. You can find Boundary breakers in a lot of places. You can watch our episodes on The Boundary Breakers YouTube channel, where you can listen to each podcast on Spotify, Apple Podcasts, or any of the other major podcasting platforms. Thanks for listening.

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