Coach as Entrepreneur

In this episode, we sit down with Rob Ott, former co-founder of a global pharmaceutical powerhouse that scaled from zero to over 5,000 employees. Today, Rob is an executive coach helping leaders navigate a rapidly changing world, where AI isn't just a tool—it's shifting the very fabric of leadership and management.

We dive into Rob’s entrepreneurial journey, the hard truths he learned about himself through his first experience with executive coaching, and why he believes we are looking at the "last generation of leaders that will only manage humans." We also tackle the realities of running a coaching business, the fear of selling, and how to reframe marketing as a responsibility to help others.

Key Takeaways:
- [00:01:10] From the garage to 5,000 employees in the pharma space.
- [00:08:52] The brutal feedback that reshaped Rob’s leadership style.
- [00:33:07] Why this is the last generation of leaders to only manage humans.
- [00:47:58] How AI will expose the "lazy leader" and close the performance gap.
- [01:05:45] Reframing marketing: If you can help someone, you have a duty to let them know.

Connect with Rob Ott:
- LinkedIn: https://www.linkedin.com/in/rob-ott/
- Website: www.ottmgt.com
- Substack: The Spark of Leadership

Connect with David Chung / KyberFive:
- Website: https://kyberfive.com
- LinkedIn: https://www.linkedin.com/in/davidchungk5/
- Growth Gap Diagnostic: https://kyberfive.com/growth-gap-insights/

What is Coach as Entrepreneur?

You became a coach to help people — but no one told you how to build the business behind it.

Coach as Entrepreneur is the show for coaches who want to go beyond referrals and create a real business that supports both their clients and their family. Each episode explores the systems, strategies, and stories that help coaches simplify marketing, attract the right clients, and grow sustainably, without burning out.

Whether you’re just starting or looking to scale, this is your roadmap to running your coaching practice like a business… and doing it with heart.

Build the system. Serve your clients. Support your family.

# Rob Ott - Jan 22, 2026

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[00:00:33] **David:** Now Rob's helping leaders [00:00:35] navigate a world where AI is going to expose every lazy leader in the [00:00:40] industry. Let's talk about the future of leadership conduct. Rob.

[00:00:44] **Rob Ott:** welcome. Oh, [00:00:45] thank you David. It's great to be with you.

[00:00:46] **David:** So, Rob, I'm, excited because I love to [00:00:50] talk with coaches about how they got into this world of coaching, but [00:00:55] also, you built your own business. You're an entrepreneur you understand the [00:01:00] struggles of. Starting out with, Right?

[00:01:04] **Rob Ott:** [00:01:05] absolutely.

[00:01:05] **David:** Why did you even start in the garage? Why not take a traditional route?

[00:01:09] **Rob Ott:** [00:01:10] Well, you know, the business that we had was, uh, [00:01:15] pharmaceutical services business, you know, for the folks that are in that industry. It was contract research. [00:01:20] And, you know, we ended up being at a company in the nineties, uh, that [00:01:25] went through, I guess what I would call, I think it was three or four major reorganizations in five [00:01:30] years.

[00:01:30] It was just that time. There was a lot of, you know, consolidation. Uh, [00:01:35] and what we realized is once we were on number four, it was the same as number two [00:01:40] structurally. And it was just exhausting. And so, you know, [00:01:45] also at the time, we were coming out of a, an experience where, uh, [00:01:50] the team that I worked with got the first monoclonal antibody for breast cancer, uh, [00:01:55] approved with the FDA, it was drug culture, Herceptin.

[00:01:57] Um, it was a really exciting time. [00:02:00] Uh, and it opened the door for a lot of other therapies that, and that was really what we were passionate and animated about, [00:02:05] which was the treatment of cancer patients, um, and offering new, new therapies for them. And so, you [00:02:10] know, we started out consulting, so I can't even say we actually started building a company.

[00:02:13] We started consulting [00:02:15] because. At the time, in the late nineties, uh, there was a lot of [00:02:20] difficulty in the industry where the pharma companies that would hire a company like mine, [00:02:25] uh, were talking past each other. And so I really honed a lot of skills in being [00:02:30] almost an interpreter and a harmonizer and a communicator.

[00:02:33] And so we found that we were able to [00:02:35] insert ourselves to explain to the, you know, to the vendor, uh, the contract research company, [00:02:40] what the pharma company wanted. And we also were able to explain to the pharma companies and the [00:02:45] biotechs what the CROs could do. And so there was, there was a [00:02:50] space for us in there and really, you know, just through, I I'm gonna say a lot of hard [00:02:55] work and a lot of luck.

[00:02:55] I mean, I, you know, I think you have to attribute them to being in the right place at the right time and [00:03:00] serving your customers well. Uh, but we turned around a few times and we had, you know, we had [00:03:05] great word of mouth business development, and we kept hiring people and expanding our projects, and then we were [00:03:10] off and running.

[00:03:10] **David:** Wow. I, I mean, it kind of sounds easy, I know it's [00:03:15] not easy and it's, it's a struggle. Were there any times, like when you're [00:03:20] going through that process, you're kind of wondering like, what am I doing?

[00:03:22] **Rob Ott:** Oh, all the time. I mean, you know, like [00:03:25] there, imposter syndrome is a real thing. Like you si you kind of look back at yourself and Yeah, I [00:03:30] mean, I guess I can make it sound really smooth, but you know, there were days where we were [00:03:35] trying to make, um, you know, we were trying to solve some really gnarly scientific problems [00:03:40] and operationalize some really challenging relationships and, you know, [00:03:45] meeting our deliverables and that wasn't always fun.

[00:03:47] Like that was, that was work. Um, [00:03:50] you know, we had a lot of, uh, a lot of high pressure. So, you know, there was always [00:03:55] relationships that we were managing and that was really where my strength was, was. You know, I was able to get a lot of [00:04:00] things done. Uh, but at the same time, I was able to bring people along with me, uh, [00:04:05] and communicate and like I said, harmonize and, and serve as that interpreter.

[00:04:09] But, you know, there were [00:04:10] days like, I mean, we, we were starting this very early on. We were in the middle of the, [00:04:15] the financial crash in 2008 and 2009, and that was the, you know, that was a shock to the [00:04:20] system because. Our business relied on investment. You know, the small biotechs that [00:04:25] we were working with all relied on investment and all that froze up.

[00:04:27] So we had to really scramble and figure [00:04:30] out what we were gonna do. You know, and I, I, if I'm, if I may, I mean, one of the other things that [00:04:35] was really interesting for us at the time was that we focused so much on building our business [00:04:40] around our people that, um, we, you know, we were a [00:04:45] remote company in, in 2000.

[00:04:47] Like we were completely remote. We never had to, well, we had like [00:04:50] one small headquarters. Where we had like maybe two or three offices, but for the most [00:04:55] part, if you had a laptop and at that time an air card, um, it didn't matter where you were in the [00:05:00] world. Like we were just happy to have you. And so what that did though, it liberated us to say, [00:05:05] let's put our dream team together.

[00:05:06] You know, if our best quality person is on the west coast, [00:05:10] then let's hire him. You know? Um, I, I feel bad for our, my poor, you know, [00:05:15] HR leader because, you know, it was like, oh, we're hiring somebody in Indiana. You gotta learn the [00:05:20] local, uh, local regs for her, you know? So, but it, it gave us a lot of freedom.

[00:05:24] **David:** [00:05:25] Yeah. So through that process as you're, you start out, the two of [00:05:30] you, you're growing the business, it's building and growing. Did you [00:05:35] know about coaching when you started your business? ex executive leadership coaching,

[00:05:39] **Rob Ott:** [00:05:40] Not when I started, but I did get introduced to it fairly early. I mean, you know, one of the [00:05:45] nice things about some of our clients is that they did have some progressive for the time [00:05:50] learning and development parts of their organization. So I came across coaches. I mean, it wasn't, you know, probably within the first [00:05:55] five years was my first exposure to it.

[00:05:57] **David:** Okay. So did you, as [00:06:00] you were a leader, trying to navigate. Growing Right. And developing and all these [00:06:05] different nuances of, you know, the pressure, the, the work you're [00:06:10] doing and, and learning to manage like, accelerate, growing team. Right. [00:06:15] you have to bring in a coach or how, what was your experience with coaches

[00:06:19] **Rob Ott:** my [00:06:20] direct experience was, is that I kind of hit a plateau. Um, you know, strategically, you [00:06:25] know, you get to a point where you move from, you know, just managing by catastrophe [00:06:30] or just by, you know, reactivity to really thinking in [00:06:35] systems and being strategic. And I had kind of like, I guess maybe about 10 years into this, I had [00:06:40] kind of hit a strategic plateau where I had always filled the role on my [00:06:45] team as the devil's advocate.

[00:06:47] So I was always the worrywart, I was always the person, like with the [00:06:50] contingency plans. And I, I thought at the time I was awesome, you know, like I had everything [00:06:55] covered and I was thinking of things. And, you know, it, by that time we were probably, [00:07:00] you know, over a hundred people and, and the leaders that I was working with that we had brought in, [00:07:05] you know, I was starting to develop a reputation for, uh, being, you know, the, [00:07:10] the, you know, the wet blanket.

[00:07:11] Like every time something was coming up and we were dealing with it, like it would be Rob, kind [00:07:15] of, you know, bringing everybody down. And so there, they, I started to get a little bit of a [00:07:20] reputation for not being as strategic as I could be. The, the remedy for that was to hire a [00:07:25] coach. And that's where I met my coach, who I still work with today.

[00:07:29] [00:07:30] Um, and that's, you know, this is like now a dozen years later, um, that, uh, he and I [00:07:35] still stay in touch and connect. But that was my first experience with executive coaching.

[00:07:38] **David:** Mm-hmm. [00:07:40] obviously that was a pretty positive relationship because you're [00:07:45] still connected 12 years later. what were some of the things that you had to work on [00:07:50] as a leader to, to grow for that company?

[00:07:53] **Rob Ott:** I think, you know, [00:07:55] it's, a lot of it, like I said, is you, you, you start out with skillsets and you know, just [00:08:00] as we were talking earlier, like I was a generalist, you know, I was always able to talk to, you know, [00:08:05] the operations teams and tell 'em what finance was looking for. 'cause I had a, I had a really wide [00:08:10] understanding of a lot of different concepts, but I wasn't very, you know, deep.

[00:08:13] I was, I wasn't a specialist in any [00:08:15] area, you know? And what I think I ended up having like learned through all this [00:08:20] is. That, my experience was, I, I, I, like I said, I hit a plateau. I really [00:08:25] needed to like, expand that, and most importantly, I needed to own it. Like, I think that [00:08:30] was the first key step in, in developing.

[00:08:32] It was, at first I was like, I don't, I, I, I [00:08:35] didn't believe the feedback, you know what I mean? Like, there's a part of me that's like, but wait a minute. I'm trying to do the right thing for the [00:08:40] team, and I'm playing that role of devil's advocate or the contrarian. And it [00:08:45] wasn't until I really like owned it and absorbed it as part of my own development [00:08:50] that, uh, I was able to unlock and, and grow.

[00:08:52] And my coach really worked hard on me. I mean, he, [00:08:55] I remember there was a point, I met him at a Dunking Donuts and, you know, I think it was like our second or third [00:09:00] session and he hit me right between the eyes with. You, you've got a [00:09:05] choice. Now you can, you, you have the feedback. You can, you can absorb it and grow.

[00:09:09] Or we can [00:09:10] stop and you know, and I mean, it probably wasn't that harsh, but it felt like a, [00:09:15] you know how your whole earth moved like three inches to the right? You felt everything lurch. And I was like, [00:09:20] okay, you know, game on. I gotta get into this.

[00:09:22] **David:** Yeah, interesting, [00:09:25] right? Because we understand our motivations, right? And we understand why [00:09:30] we're doing things in a certain way. Most of the time, at least we think that to ourselves [00:09:35] then. When we start to get feedback from other people doing like a 360 [00:09:40] assessment, then kind of re reality hits because it's always, it's a question to [00:09:45] me of the, the process of coaching, right?

[00:09:47] Because do you work on you [00:09:50] becoming a better you or if you're in like, leadership, if you're being coached for leadership [00:09:55] development at, at like the top level, right? do you work on becoming a better leader [00:10:00] for your business, right? For the people you, you lead. And [00:10:05] so when you get that feedback, it's hard because you have such good intentions about [00:10:10] growing the business, being there for the people. You're like, I thought I was doing everything [00:10:15] right.

[00:10:16] **Rob Ott:** It was jarring. Yeah, it was. Absolutely. And I'm, I'm sorry I broke, broke in, but [00:10:20] you're, you a, you hit it right on the head. It was, you know, there is a level of [00:10:25] acceptance that comes with a person who is coachable. Um, and I didn't know, I was like, I, you know, you [00:10:30] can't draw this up. It's not like I was thinking this was gonna happen in my mind.

[00:10:33] But,

[00:10:34] **David:** Yeah,[00:10:35]

[00:10:35] **Rob Ott:** in order to really grow, you have to, you have to be willing to take that feedback and, you [00:10:40] know, process it and, and like I said, own it. I mean, really.

[00:10:43] **David:** That's hard, right? [00:10:45] Because you have to accept that you are not perfect and that [00:10:50] have, and be humble about it.

[00:10:51] **Rob Ott:** The degree of professional maturity,

[00:10:53] **David:** that

[00:10:53] **Rob Ott:** you know, it's a, the [00:10:55] maturity that comes along with that. I'm sorry, I didn't mean to cut in.

[00:10:57] **David:** No, no, you're, you're a hundred percent right, [00:11:00] right. Because you have to be. The people who are mature enough to understand and [00:11:05] separate the emotion from it. And if you're really there for the business and for the people [00:11:10] in the business, it's like being a father, right? You, you have

[00:11:14] **Rob Ott:** Yes, I do. [00:11:15] Yep. Three kids.

[00:11:15] **David:** You wanna be the best dad you can be for them.

[00:11:19] [00:11:20] Right? You don't wanna be the jerk. Right.

[00:11:22] **Rob Ott:** Yeah.

[00:11:22] **David:** And so I mean, when you're running a [00:11:25] business, you're a leader in a business, it's kind of like being a parent. And if you wanna be [00:11:30] there to separate the, the familiarize, but you like, if you want that business to grow and to do the [00:11:35] best and to be high performing, you need to be the best [00:11:40] leader for those people.

[00:11:41] And I think that is, it's hard, but when you realize that [00:11:45] it's not really about you, it's about either the business or the people that you're working with, then [00:11:50] you can accept that, okay, for them I need to do these things so that [00:11:55] we as a organization, as a group, make that pivot and really like launch.

[00:11:59] **Rob Ott:** [00:12:00] I think, you know, one of the other things that I benefited from was, uh, my mentor, [00:12:05] um, and my, you know, direct supervisor for years, you know, in, in the hierarchy of the company. Uh, in time [00:12:10] we brought in a really experienced COO. She was a coach as well, and, you know, [00:12:15] she, she actually was very encouraging for me to take this on when I was, you know, starting to figure out what I wanted to [00:12:20] do in after, after the business.

[00:12:22] But, um, we always traced it back to [00:12:25] value. So very, very, uh, similar to what you're saying, we sat down as a company and really [00:12:30] figured out what was most important to us. I still have 'em hanging on my wall, actually. I'm looking at 'em right now. [00:12:35] Uh, but ultimately all that came back to like, we, you know, it wasn't a family [00:12:40] business, but it was really collegial and it was really focused on, you know, how do we, [00:12:45] if we unlock the human potential and we give people as much as we can to support them, [00:12:50] the magic happened and that was really important to us.

[00:12:53] And so, yeah, there was a very. [00:12:55] Paternalistic and not only male paternalistic, I mean like a, a parental kind of [00:13:00] overview, familial kind of feel to that company. Yeah. Our culture was great like [00:13:05] that.

[00:13:05] **David:** I love it. The way I see, you know, companies today, I [00:13:10] wish that the cultures of company were, you don't need to be families. Like, I disagree. [00:13:15] Like now that you wanna make the company feel like a com, like a family, [00:13:20] because there's other.

[00:13:21] **Rob Ott:** You need boundaries. Boundaries, yeah.

[00:13:22] **David:** that, but yeah. [00:13:25] But you wanna make it so that yeah, people enjoy being there, that you wanna, like, [00:13:30] you are excited to be there, to be working together you spend so much [00:13:35] time, like you spend more time with your coworkers than your families most of the time. Uh, I mean, [00:13:40] and traditional right?

[00:13:42] **Rob Ott:** I, yeah. And if I can comment on that, I mean [00:13:45] we, you know, you get perspective from time and distance and you know, we [00:13:50] were like, we built the company up and then we were acquired in 2016, so it's been almost 10 [00:13:55] years since the acquisition. I mean, wow. When I really think about it. That's wild. I just wanted people, you know, I think I [00:14:00] take great pride in when I see people that I used to work with or come across 'em in different settings [00:14:05] and I get the comments that this was the best place I ever worked.

[00:14:08] You know, this was, this was a [00:14:10] great field. Like, so, even though it's not a family business, it was really important to,

[00:14:14] **David:** Yeah.

[00:14:14] **Rob Ott:** to, [00:14:15] to create that culture in that environment. And that's something that I, you know, even with my coaching and the, you know, the [00:14:20] advisory that I do now, I'm always focused on like, how can you, how can you improve that [00:14:25] culture?

[00:14:25] And it's gotta be natural, but it's, it's something to strive for for sure.

[00:14:28] **David:** Yeah. [00:14:30] And that's what I was gonna ask is how has your, your experience as a leader, your [00:14:35] experience being coached, informed the work you do now as a coach?

[00:14:39] **Rob Ott:** [00:14:40] Yeah. Um. I, I think I understood it was really interesting. Like I [00:14:45] understood the value of coaching and I understood the process from a, like a standpoint of going [00:14:50] through it, um, and having been coached. So I think that was really invaluable to me in a lot of ways. And, [00:14:55] and there are tiny ways. It's just the way feedback's gonna be received, you know, the way that you could [00:15:00] deliver it, when to, you know, when to, you know, what we call honest label, something like, and that's, that [00:15:05] hit you right between the eyes with something really important.

[00:15:07] But you gotta work to that. You gotta build that relationship. So those [00:15:10] are all, you know, really con, you know, critical and important components to that. I think that, [00:15:15] I didn't realize that at the time, but the cultivation of self-awareness. You know, being able to [00:15:20] accept that feedback that I was talking about, being able to,

[00:15:23] Process it, that, [00:15:25] that, that really unlocked a lot of different things.

[00:15:27] So I'm always looking for that moment. That's what I start with when I, [00:15:30] when I'm coaching a, a leader, is I want to get a sense of how self-aware they are and [00:15:35] you know, how they can build that up. Because once you can unlock that, I mean, that, that doesn't solve every [00:15:40] problem by any stretch or even, you know, help them address every, ch, every opportunity.

[00:15:44] But [00:15:45] knowing what, you know, going in about yourself really does, you know, shape the future for [00:15:50] you.

[00:15:50] **David:** The man who introduced me into coaching, his name is Will Linson. He called it [00:15:55] is the leader coachable? Like what's their coachability assessment? Like, are they, are they humble enough? [00:16:00] Will they take action on on these changes? Will they be disciplined to, to do this thing? These [00:16:05] things, I think most coaches, I don't know, like it's, it's 'cause it's about client selection. If you [00:16:10] as a coach can choose between like 10 people [00:16:15] you know, some of them are not humble, like, would you wanna work with them or [00:16:20] should you like, and, and this is kind of goes into the a a little bit your client selection, [00:16:25] like how do you go about client selection? I, I know a lot of coaches out there [00:16:30] too desperate for work, and so they don't, they don't [00:16:35] even think about it. But the problem with that is like, end up in a, [00:16:40] business relationship, right. With somebody who is just one, maybe [00:16:45] just not excited to be in that relationship with you, but two is just gonna be like a [00:16:50] soul sucking vampire in

[00:16:52] **Rob Ott:** Yeah.

[00:16:52] **David:** ways.

[00:16:53] **Rob Ott:** know, some people drain [00:16:55] energy and some people radiate. It's just, you know, the way that the world works. Um, I think that [00:17:00] I struggled with that when I first started because. You know, there's a component to some of [00:17:05] the certifications. It's like, you gotta get hours and you gotta get time with people.

[00:17:08] So you're out there like, [00:17:10] you know, I'll coach anybody and that's just not a really good recipe for [00:17:15] success. Um, you know, you asked, I guess, how I do it and, you know, my [00:17:20] main component is really all about the chemistry call that I, you know, I call it a chemistry call in the beginning, or at least the [00:17:25] meeting so that we can sit down and.

[00:17:27] Understand what that person's looking for. [00:17:30] Um, understand, like, you know, again, I, I do, I don't have a formal coachability [00:17:35] assessment. Like I don't put them through a questionnaire or anything like that, but I will sit down and, and like, if I [00:17:40] connect with them and I'm able to understand what they're looking for and it's in my skill, you know, [00:17:45] skillset to help them, then sure.

[00:17:46] But I will, you know, in a, you know, it, it comes with [00:17:50] confidence, but at this point, if there's somebody that I know is not gonna be a good fit for me, I will [00:17:55] beg off or refer them to a colleague. And, you know, that's one of the beau and we can talk a little bit about [00:18:00] that. But the beauty of being in a coaching community is that I've got so many connections that I know that [00:18:05] people specialize in all different modalities and all different, you know, uh, types of [00:18:10] coaching.

[00:18:10] And sometimes it's a better fit and, you know, like, I'll finish with this point, but [00:18:15] it's the, it's the confidence that you get to know that you're not, like you, you, there's things that you just [00:18:20] have to say no to or, or should back away from and not, not feel like you should coach everybody.

[00:18:24] **David:** Do you [00:18:25] feel like it's your experience as a, business owner, business leader, [00:18:30] because like, I imagine you had to make a lot of hard decisions, right? And you had to, you [00:18:35] went through those experiences. Do you feel like that helps with your ability to, [00:18:40] to say no to clients?

[00:18:42] **Rob Ott:** It does. Um, I think, you [00:18:45] know, one of the things that I drilled into when I was kind of starting my coaching journey and really getting [00:18:50] serious about it was, you know, I spoke to somebody and they were like, what's your superpower? And it took me a little bit, I mean, [00:18:55] the question took me back. Like, I was like, oh, and my superpower to, to, to kind of bring [00:19:00] it to your point is that I have 25, 30 years of experience of living this life.[00:19:05]

[00:19:05] You know, I know what entrepreneurs are going through. I know what it's like to deal with hypergrowth. I know those [00:19:10] tough trade-offs and those decisions. You know, I, I tried to, and you know, I did this with [00:19:15] varying degrees of success, but I think most people would, that you talk to that worked for me, would probably, or worked [00:19:20] with me, would say that, you know, I did my best to explain why I was doing things, [00:19:25] you know, why, like, I, I had to make decisions about whether, you know, I'll give you an example.

[00:19:29] Like, you [00:19:30] know, I used to manage a, uh, a triage call, a sales triage call where, you know, [00:19:35] the sales teams would bring in these opportunities and some of them were just not fits. Whether it was a [00:19:40] resourcing opportunity or it didn't fit the overall strategy. And, you know, [00:19:45] sometimes I would have to say to a business, you know, a hardworking, you know, business development [00:19:50] person, we can't do this project.

[00:19:51] We just don't have the staff. We're not gonna deliver with quality. [00:19:55] You know, it's a problem. And that was, that was a tough call. I mean, I, I don't shy away from [00:20:00] 'em because I think somebody has to make that decision, but I always explained why, you know, they may not have [00:20:05] liked it, and I'm sure, and I know, you know, I, I have some friends still that, you know, didn't like it.

[00:20:09] But, [00:20:10] you know, generally speaking, I, I tried my best to help them understand.

[00:20:13] **David:** Yeah. [00:20:15] In my perspective, like the more experience you have, the better you can do anything, right? [00:20:20] So if, if you're a carpenter, the more, the more things you build, the better you just get over [00:20:25] time. And I think for coaches too, it's, it's very similar. Like the more life experience you [00:20:30] have, the more coaching experience you have, just can make you better at doing that [00:20:35] thing. And so that's why I was, I was curious how that informed your ability to do [00:20:40] that, of, c selecting your clients that you work with.

[00:20:42] **Rob Ott:** You know what the biggest challenge in that was? And I'll [00:20:45] just share this real quick and then, you know, we can pivot off of it if you want. But, I, in, in my [00:20:50] role, I was very decisive. I had to, you know, I had to make a lot of decisions. I had to give a lot of [00:20:55] recommendations and a lot of advice.

[00:20:56] And I think one of the biggest adjustments for me as a coach [00:21:00] was, you know, the methodology of I'm not telling you what to do anymore. You know, I could, I could [00:21:05] solve this problem for you. I mean, like, that was naturally my, my skillset. I want you to solve it. I [00:21:10] want you to do the work. I want you to do the growth.

[00:21:12] You know, we always use the analogy, at least the group that I worked [00:21:15] with, which was I'm walking on the path with you with a flashlight. I'm not in front of you. I'm not leading [00:21:20] you. I'm just showing you some things that you may not have seen. Um, and hopefully you're guiding you [00:21:25] along that way.

[00:21:25] **David:** I'd love to hear your view of what coaching is and [00:21:30] your approach to it, because you, you brought up this point of like, I could tell you exactly how to solve this [00:21:35] problem, right? Or am I guiding you, shining the light for [00:21:40] you? in your definition of what is coaching, like What? What is coaching for you?

[00:21:44] **Rob Ott:** I think, you [00:21:45] know, for me, I come outta the school of, uh, from Columbia, the three CP program, [00:21:50] uh, the Columbia Coaching Program. And we look at it as total person coaching. I mean, like, [00:21:55] it's, it's really surfacing their issues and helping them see things in a different [00:22:00] way. You know, uh, if anybody from the Columbia program's listening, they're probably gonna laugh at me because I'm not gonna [00:22:05] articulate it as nearly as well as the, as the folks do.

[00:22:07] But it's, it's really, you know, [00:22:10] like understanding that the solution's in them. It's my job to help them reveal [00:22:15] that. You know, I always look at it as I have to build trust so that they, you know, that I have permission to [00:22:20] advance and, you know, I can't just give them the answer. Some of 'em don't want the answer.

[00:22:23] Some of 'em really want, you [00:22:25] know, it, it fluctuates. Sometimes they're just like, just tell me what the answer is. And I'm like, well, you know, if you really wanna [00:22:30] know, okay, we'll talk, but I want you to do that work. But my idea is, my philosophy in [00:22:35] that is I'm here to blend my experience so that, you know, [00:22:40] however long our duration of our engagement is, by the time you end it with me or [00:22:45] we, we kind of come to conclusion, you're better skilled to handle the things that you're gonna be dealing with in [00:22:50] life because of the work you did.

[00:22:51] Not because I, I solved problems for you. That's, that's a consultant. Like, [00:22:55] that's, that's a, that's, you know, that's, it's a totally different animal.

[00:22:57] **David:** yeah. 'cause sometimes, like in the [00:23:00] conversations that I've had with other coaches, it's, it, there's a blend of coaching and [00:23:05] mentoring,

[00:23:05] **Rob Ott:** Mm-hmm.

[00:23:06] **David:** And so obviously you, you can consult and that's, [00:23:10] that's pretty, I think that's, that's understandable. But when it, [00:23:15] of coaching and mentoring, and let me know your experience, right?

[00:23:19] Like the [00:23:20] clients who select to work with you, part of it is, I would assume factors in your [00:23:25] background as. Who, who exited and [00:23:30] who's been there, right?

[00:23:31] **Rob Ott:** Yeah, they come to me for a specific reason, and more often than not, [00:23:35] um, I think what I found is there is that subset, there is that group of people that [00:23:40] are like, you know, in C-Suite emerging, you know, developing, developing senior leaders. [00:23:45] Um, and that's a very straightforward, like, they're coming to me because of my [00:23:50] experience.

[00:23:50] You know, I've done some pro bono work. Um, I've done some work with, you know, [00:23:55] young, like I call them emerging professionals because they're just coming into the [00:24:00] industry. They need more mentoring. So I will modify my style because they just don't have [00:24:05] the life experience. I can't draw on their experience to help them solve their problem.

[00:24:09] So we [00:24:10] have different kinds of conversations. I'm still not telling them what to do, but I'm giving them [00:24:15] more of a sounding board than I would say for like a C-suite or a, you know, like an emerging [00:24:20] leader kind of thing.

[00:24:20] **David:** Okay. Makes sense. I wanna go back to the [00:24:25] topic that you brought up, which was about community, because this came up in a another conversation as [00:24:30] well. It's, you know, the coaching community. so what does your [00:24:35] community look like? How do you guys interact with each other?

[00:24:38] How do you guys work [00:24:40] together or collaborate? What does that look for you look like for

[00:24:43] **Rob Ott:** Yeah. And you know, I think [00:24:45] that probably the overarching component that I would say in my community is like [00:24:50] my desire for networking. And I'm not saying this is part of my community. I should, maybe I shouldn't frame it that way, but you know, when I [00:24:55] left my, my company and made my exit, I realized that I had led a lot of [00:25:00] my network wither.

[00:25:00] Like I knew everything that was going on in the business, but outside of it I [00:25:05] was, you know, I was really like looking around saying, oh my gosh, you know, like I haven't kept up with a lot of the things that I want [00:25:10] to. So I committed when I started. Did this, this new endeavor to really [00:25:15] build a network. Um, and so, you know, I had, uh, you know, I think there were [00:25:20] 35 of us in the Columbia cohort that I went through in, in, uh, in 2023.[00:25:25]

[00:25:25] And we've all, you know, I can't say we've all stayed close and in touch, but we have like a, you know, [00:25:30] we have a, a WhatsApp chat room that we all kind of chime in on every once in a while. Um, I [00:25:35] will make a point to reach out to some of my closer colleagues and we just [00:25:40] kind of sound, you know, you know, bounce things off each other, sounding board style.

[00:25:43] We have like a monthly [00:25:45] meeting where we get together, but we drive those so that we have the ability to, you know, just to connect. [00:25:50] And, through that, through those folks I've made connections with other coaches. Um, [00:25:55] I've kept in touch, like I said, with my coach who's now, I guess, pretty much retired at this point.

[00:25:59] Um, [00:26:00] but he and I still talk about, you know, he's actually been a great mentor to me in helping me [00:26:05] develop my business and, work in my confidence. You know, it just is. I mean, 'cause like you're, it's [00:26:10] almost like starting over, but building that community was really important. And I've stayed in touch with the folks at [00:26:15] Columbia.

[00:26:15] I'm fortunate, I live in New Jersey, so I'm only, you know, 45 minutes outside of the city if I need to get [00:26:20] up into New York. Um, and we just had an amazing event [00:26:25] in, uh, October where, you know, there was 500 of us that were on a, it was [00:26:30] a, a conference, uh, run by Columbia that was focused on hybrid, uh, intelligence for [00:26:35] coaching.

[00:26:35] And it was an amazing event and I got to reconnect with a bunch of my old instructors and [00:26:40] you know, that group. So I, I think that the communities are there, but the [00:26:45] other component is, is you gotta work to work to build your community too. So, and that's something, like I said, [00:26:50] I really focused on this time around.

[00:26:51] **David:** Do you have, Like a small community that you, [00:26:55] you guys kind of collaborate with, like as, as you're saying like, this, this person doesn't fit me, [00:27:00] but I know somebody who they would work well with. Do you guys kind of have like a, not necessarily [00:27:05] necessarily, not necessarily like a formalized group, but like a informal, like, here's my short [00:27:10] list of

[00:27:10] **Rob Ott:** Yeah. And, and I would say, and I'll give you an example. Like there's one [00:27:15] coach that I work with. Um, she is, she was in my cohort. She, you know, [00:27:20] she and I like really hit it off. She, based on the west coast, I'm in a little bit of a sticky [00:27:25] wicket with one of my, you know, potential clients. And, you know, I [00:27:30] didn't do anything unethical or anything like that, but I'm like, I don't know how I would handle this and I need an objective [00:27:35] viewpoint.

[00:27:35] So I texted her today and I said, Hey, can I get 15 minutes with you tomorrow? I just need like a, a [00:27:40] laser, laser session real fast to like go through something. And, you know, I'm looking forward to catching up [00:27:45] with her regardless, but, uh, she's gonna help me out. So we do those kinds of things for each other [00:27:50] where, you know, the, one of the women that I worked with that is a coach, he's an internal coach.

[00:27:54] She had [00:27:55] a bunch of AI questions and so she knows that I'm involved in that. And uh, you know, was, [00:28:00] you know, asking me just systems thinking, how, how are you, working with my [00:28:05] clients on some of those things? So, you know, it, it's, it's a, it's a village, you know, it's, and, [00:28:10] and you bond with people and you, you know, you, like, I'm thrilled that we've stayed as, as close [00:28:15] in, in touch that we have because you're always worried.

[00:28:17] You have these great experiences and then, [00:28:20] you know, the groups dissolve the purpose to find, like, finishes up. When we were having our [00:28:25] last night together, I looked around and I'm like, this is the last time we're all gonna be in the same [00:28:30] room together. And it was kind of like a poignant moment. But, you know, it was, we, we do our best to stay in [00:28:35] touch where we can.

[00:28:35] **David:** I, I love that. I would say that that's probably one of my biggest [00:28:40] regrets is like, 'cause I'm from the states. I, I was born in Chicago, uh, I [00:28:45] went to university and then I moved out. Uh, so I, I live, I'm living that [00:28:50] expat life, right. But when I did that, I kind of, there are a few people I stayed in [00:28:55] contact with, but not a lot.

[00:28:56] And so like, I really, again, like, kind of like you said, like my [00:29:00] network kind of withered because I just, got busy with the work that I was [00:29:05] doing out in Asia and then life happened in kids and then working kids and then it's [00:29:10] hard to like try to stay connected.

[00:29:12] **Rob Ott:** You know, one of the ways, and, and I don't know, maybe this is something to [00:29:15] think about. I, I'll offer this up to you and you can make of it as you wish, but like. You [00:29:20] know, when I started coaching again four years ago, seriously, um, I went out and reintroduced myself to [00:29:25] a lot of the people. I used it as an opportunity, not so much to sell the business.

[00:29:28] Like, I mean, there was always that, [00:29:30] you know, there, that ancillary effect. But I just wanted to reintroduce myself to folks like, Hey, what [00:29:35] have you been doing? So, you know, we always, we always talk about that thousand cups of coffee. One cup of coffee [00:29:40] leads you to somebody else, to another person. So you're always out, like, you know, talking to people and networking and everything else.

[00:29:44] [00:29:45] So, um, I, I, you know, we were talking a little bit about kids. My son's, um, gonna go to [00:29:50] college in a couple next week, actually. He's leaving in New Zealand and, you know, so [00:29:55] going from New Jersey to New Zealand, he's been there before. But I'm like, really spend some time building up [00:30:00] your, like your support network, your friends, your, you know, it's a great time to be there, but it's, [00:30:05] it's, he's gonna be really far away from, you know, what he's used to.

[00:30:07] So it's really important to have [00:30:10] that people around you.

[00:30:37] **David:** That's gonna be a great experience. 'cause I [00:30:40] think any time, any opportunity you can go and, you know, be in a different culture, [00:30:45] uh, and just open yourself to learning is, I didn't [00:30:50] realize, like, as a Korean American, like I thought I was pretty like open [00:30:55] and understanding of the world. And then as I left America and [00:31:00] spent almost a decade and a half in Asia, [00:31:05] like, wow, the way the world per perceives, like what's [00:31:10] going on and the way we think in America are so, so

[00:31:13] **Rob Ott:** Yeah.

[00:31:14] **David:** [00:31:15] Um, and, you know, culture, society, all that stuff is, plays into it, but I think it's, it's great and [00:31:20] like we should all try to spend time outside of normal, like [00:31:25] social context. I kind of wanna, I want to jump into the, the, the ai because [00:31:30] AI is such a big, see elephant in the room, right? So [00:31:35] what's the situation for you? How are, are you coaching people who are doing like AI [00:31:40] development or are they, are they worried about ai? What is, what is the thing [00:31:45] that, what's the cross section between your coaching and

[00:31:47] **Rob Ott:** Yeah, so there is a, um. [00:31:50] This is a work in progress. So I like, you know, I don't wanna sit here and ever explain to you that I have it all figured [00:31:55] out. Um, I'm doing a lot of work, first of all. I mean, I think where I come from [00:32:00] in, you know, I've always been like, tech curious, tech, fillic, whatever you want to, whatever [00:32:05] adjective you wanna put on it.

[00:32:05] So I, you know, like I was saying, we were building air cards and, you know, [00:32:10] running people with laptops 25 years ago before, you know, uh, before anything like that [00:32:15] was even normal. Um. But ultimately, like what I'm doing, so I, [00:32:20] part of my advisory and and consulting is working with a, um, trade [00:32:25] organization that focuses on the life sciences here in New Jersey.

[00:32:29] And so [00:32:30] I run their AI digital health team, um, that's put me in contact with a [00:32:35] number of, you know, incredibly smart, thoughtful leaders from, you [00:32:40] know, all the way from small startups that like, you know, like our vibe coding and building, you know, crazy [00:32:45] apps that are just solving things that I was like, I didn't even know that was a problem.

[00:32:48] Um, and then, you know, they're [00:32:50] brilliant all the way up to like enterprise level people at like IBM and Johnson and Johnson that are just, you [00:32:55] know, really looking at drug development in an entirely different way. And it's an exciting [00:33:00] time. I think where I'm focused in on it is that I [00:33:05] recognize that, um, there's a couple of things.

[00:33:07] So I'm gonna throw out some data points or some, you know, some [00:33:10] information, you know, this, um, this is probably the last generation of leaders [00:33:15] that will only manage humans. Um, you know, the next generation are gonna have to deal with, [00:33:20] agents, multi, multi-agent setups, robots, whatever it may be. [00:33:25] You know, and they may even be managed by any, I don't know.

[00:33:27] I mean, like, the future is wide open on a lot of these [00:33:30] things. So some of this stuff is really, you know, there's gonna be new skills that are gonna be needed. I'm doing [00:33:35] a lot of reading on, you know, like when you think about what work is and where value is [00:33:40] created and the systems thinking changes, you know, everybody talks about AI's gonna take your [00:33:45] job or it's not gonna take your job.

[00:33:46] Like, I don't know what the answer to that is. I think what, what I do know is that there's a lot that's gonna [00:33:50] change and there are a number of leaders that really need to [00:33:55] become. You know, I guess I'll call it data fluent or AI savvy, they don't [00:34:00] necessarily need to code, they don't necessarily need to be on the front lines with it, but they need to [00:34:05] understand it enough to, to run an organization that's gonna be impacted by it.[00:34:10]

[00:34:10] **David:** Yeah.

[00:34:10] **Rob Ott:** And so what I'm trying to do is help them on ramp to that. And there's also a lot of fear. [00:34:15] I mean, you know, when you think about the, you know, the, the leaders that are in their forties and fifties [00:34:20] that are too young to actually retire, but are gonna like, be in that leadership [00:34:25] role, they're, they gotta catch up.

[00:34:26] You know, like they have to really

[00:34:28] **David:** Yeah.

[00:34:29] **Rob Ott:** like, make that [00:34:30] transition and it's gonna be a hard turn for a lot of people. So that's where I'm trying to insert myself [00:34:35] and help them, you know, I don't wanna, I don't wanna undersell the AI component. It's a big component, but, you know, [00:34:40] there are a lot of change management transformations, like those [00:34:45] foundation fundamentals.

[00:34:47] Those are what, what, you know, a lot of the work has to be too.

[00:34:49] **David:** [00:34:50] Yeah, because, you know, there's a lot of, as you, as you said, like, uh, [00:34:55] there's a lot to cover, but as you said, there's a lot of fear about the ai. [00:35:00] Taking your job. And so the leaders you work with, like as you're [00:35:05] coaching them, is that an underlying fear that they have or is it just like, how do, how do we [00:35:10] leverage and use this technology for the business? What are you, what are their concerns about [00:35:15] AI right now?

[00:35:16] **Rob Ott:** I mean it's, it's probably a little bit of all the above, you know, of the things [00:35:20] you just said, but you know, ultimately what I'm seeing is they're going [00:35:25] through a technological change that is going so fast. You know, you'll hear people say they [00:35:30] can't read fast enough to keep up, you know, they don't know what it means.

[00:35:33] Like the stuff that they thought they [00:35:35] understood yesterday is gonna be different next week, or it's already changing. So the speed [00:35:40] and, you know, their ability to make that turn, because I think a lot of people are just worried that they're gonna be [00:35:45] left behind. And so that is, that's, that's a primal fear.

[00:35:49] I [00:35:50] mean, like, you know, the, the slowing down the, you know, life is passing you by, [00:35:55] that's a, that doesn't, I mean, AI is doing it at hyper speed, but that's a real [00:36:00] transition for anybody. And, you know, so these, these guys

[00:36:03] **David:** Yeah.

[00:36:03] **Rob Ott:** and women, like, they're, [00:36:05] they're in that stage of their career where, you know, you can't coast, you know, like nobody's, and [00:36:10] I'm, I'm not saying that they're want to coast, but like they're being challenged in ways that they probably never [00:36:15] have at the, at speed and scale, you know?

[00:36:17] **David:** Well, yeah. The speed at [00:36:20] which technology is moving right now is every week. If not every [00:36:25] day something is being released and developed. [00:36:30] is just another, like, step forward. But if we're taking a step forward every [00:36:35] day, where we, it used to be a step every, like six months, every, every month, you [00:36:40] know, we're accelerating at such a pace that you know, it's exponential growth, right? And, [00:36:45] and development in, in so many different facets. I was just, yesterday [00:36:50] I listened to, uh, one of my favorite podcasts is Diary of A CEO, with Steven [00:36:55] Bartlett, and he was interviewing, Tony Robbins. [00:37:00] And it, it's a great PO episode. Like because it, it just dropped just, [00:37:05] uh, a, maybe a few days ago, but he was, Tony Robbins was saying like, you gotta learn, look for the [00:37:10] patterns, right? And he was saying, you know, uh, back in the 18 hundreds, [00:37:15] the Luddites and the Thrashers, so they started bringing in technology [00:37:20] that replaced the human workers, what they were doing. And so. The [00:37:25] problem that happened was the workers, their identity was so wrapped up in the [00:37:30] work that they did, that when these machines could come in and do [00:37:35] their work, one, they lost their job. Two, they lost their identity. [00:37:40] And then the, the outcome or the, the reaction to that was [00:37:45] outrage, and then destruction of Of property and [00:37:50] rioting.

[00:37:50] **Rob Ott:** Great. You know, and, and that, that is a, [00:37:55] um, that is something that is primal. Like I said, it's real. It's, it's, you know, people are gonna lose more than [00:38:00] just their livelihoods in a lot of ways. You know, like their identity is important. You know, you can go all the way back to [00:38:05] even Queen Elizabeth. Like, you know, they, they, the development of the mechanical [00:38:10] loom was just starting at that stage, and she wouldn't sanction a charter for them [00:38:15] to, to develop that technology because it was gonna up, you know, all the cottage [00:38:20] industry, I don't even know what you call loom loomer.

[00:38:22] I don't, I don't know, like whoever was a weaver, like whatever [00:38:25] they were doing, uh, was, they were, they were out of, they were gonna be outta work or out [00:38:30] of, out of a, out of a livelihood and out of a, out of an identity. I think you, you hit it on the head there.

[00:38:34] **David:** [00:38:35] Like this is all fresh to me and I'm just, I'm processing it. Um, [00:38:40] right now one is like, it's a very real possibility, right? Of like, [00:38:45] I mean this is why like Elon Musk is talking about UBI, right? Or universal, [00:38:50] uh, income, right?

[00:38:51] **Rob Ott:** Yep.

[00:38:51] **David:** Um, universal basic income, right? Because [00:38:55] there's gonna be a whole lot of people out of the job. but you know, as you're, you, you've got kids. [00:39:00] I've got a 10 and a 5-year-old. This is their life is gonna. If they're gonna [00:39:05] walk right into this, where they might have an an AI agent managing them, or, or [00:39:10] they're gonna be managing ai. Right. I mean, obviously no one knows the [00:39:15] answer, but how do we prepare for that?

[00:39:16] **Rob Ott:** I think it's different. I mean, like, you know, again, this is, this is [00:39:20] one, one angle, you know, 'cause there's, you know, I've learned anything, like, life is all about [00:39:25] perspective and complexity and nuance. But, um, I, I'll, I'll share another story and this is [00:39:30] from a book that I would reading called Reshuffle, which is really an excellent book.

[00:39:33] Um, I'll share it with you [00:39:35] after the, after, uh, later on. You know, when you think about like, and I reflect on my [00:39:40] career, like when I first started and I was doing work even before my company, [00:39:45] uh, I would literally go out into the field and hand write a report. I would bring that [00:39:50] report back in and hand it into the word processing pool, and then they would type it.[00:39:55]

[00:39:55] And they were the people that were working in the word processors because we didn't have computers on every [00:40:00] desk at the time. You know, I'm really dating myself now.

[00:40:02] **David:** Yeah,

[00:40:03] **Rob Ott:** They were kind of the evolution of [00:40:05] the typing pool. And you know, when you think about it typing, you know, we had a [00:40:10] typing pool where, because all of our document creation was constrained by the typewriter, [00:40:15] you know, formatting, typing, it was all limited to that, you know, the word [00:40:20] processor.

[00:40:20] Basically reorganize that work because those people could then work [00:40:25] on the computer and they didn't have the same constraints. And in time, you know, by [00:40:30] the time I was, you know, not too long after I started that word processing group went away because [00:40:35] everybody had a computer and a laptop. But the bottom line is, is that everybody was still [00:40:40] typing.

[00:40:40] Now, typing may go away one day. I mean, like, I think that that's the case, but the work was still [00:40:45] there. It was just being done in a different way. So I think one of the things that I, I'm trying to get [00:40:50] people to think about when I coach them is what, where did the value extraction from [00:40:55] the work? Like, what is being reorganized and where do you need to be a part of it?

[00:40:59] You know, the [00:41:00] health, the health industry is highly regulated. Um, and it's something we're really looking at [00:41:05] because, I don't wanna say doctors are gonna go away, I mean, but the value that you place on a doctor's [00:41:10] knowledge. Knowledge is being commoditized by ai. So you don't know where that's gonna

[00:41:14] **David:** [00:41:15] Mm-hmm.

[00:41:15] **Rob Ott:** change the system.

[00:41:16] And so the people that can predict that and can really analyze [00:41:20] that or coordinate and reorganize that, that's where I think it's gonna go. And, and, you [00:41:25] know, I mean, you, you, UBI may be a thing here for our future. I, I don't know the answer to that, but I do know [00:41:30] that there's gonna be stuff that needs to be done, you know, and it's just a question of how do you, how do you [00:41:35] envision that?

[00:41:35] And that's where creativity comes in, you know, like systems thinking. Like I said, [00:41:40] it's, you know, it's, it's, it's really, and for me, I'm fascinated by it. Like I'm in, like, I really want [00:41:45] to, I want to see where it goes. And I, if I can help people be comfortable doing that, [00:41:50] even better.

[00:41:50] **David:** For me, like one, I, I'm always, I've always been interested in the [00:41:55] technology, I've, I've learned over the years, I, I am a systems thinker. I like to look at the patterns. I like [00:42:00] to see how things are, are working and fit together. as a parent of young [00:42:05] kids, like, I wanna learn this thing because I need to learn this so I can help them so that [00:42:10] they can be successful because future is gonna be, I mean, it's, it's changing [00:42:15] fast now.

[00:42:15] I can't imagine in 10 years what it's looking like,

[00:42:18] **Rob Ott:** Yeah, yeah,

[00:42:19] **David:** And [00:42:20] so they have to be adaptable, they have to be resilient to that [00:42:25] change, and they have to be lifelong learners because right now we can't [00:42:30] even keep up with the things that are changing. So,

[00:42:32] Oh yeah, I, so I put it this way for my son because [00:42:35] he's doing a, a project right now for school, and I was saying, like, right now, the [00:42:40] differentiating, I think, I think that separate people are, [00:42:45] are these three things, right?

[00:42:46] It's your ability to learn, your ability to apply [00:42:50] how much effort you're gonna put into all of those, those two things.

[00:42:53] **Rob Ott:** Totally. I You're [00:42:55] spot on. I agree completely. I mean, I think that that's, you know, so what, what I am [00:43:00] really paying attention to is what the schools are doing. You know, I do some work, you know, in just [00:43:05] in the, my traveling around the state, like I'm very interested in some of the workforce development [00:43:10] that's, that's going on.

[00:43:11] You know, both because it's a coaching opportunity for me, but it's also, you know, I'm thinking [00:43:15] about my kids and what do they need to learn. And I mean, you have the, you have the one extreme that says it's [00:43:20] rotting their brain, and they're never gonna be critical thinkers because they're gonna rely on the AI and [00:43:25] they're gonna, the people that don't know how to use it are gonna be left behind on the other extreme because they never touched it, [00:43:30] and they have no idea how this magic box works and makes things happen.

[00:43:33] So, somewhere in [00:43:35] there, as with everything, there's a, there's a balancing point of, you know, the, I used to call it the [00:43:40] goldilock spot, where everything's just right. Like you, you've got the right balance of risk and you know, [00:43:45] you're learning and you're, you're hustling and applying things so that you can work on 'em.

[00:43:49] So, [00:43:50] yes.

[00:43:50] **David:** Yeah. the way I was talking to somebody, uh, so [00:43:55] this, this is, this is the way I, this is my metaphor. have a hammer, right? [00:44:00] And if you've never seen a hammer before, you've never interacted with one before, you [00:44:05] might use it properly. grab the handle and you hit the nail on the head, [00:44:10] but you might use the handle to hit the nail. might not even use it to hit a, [00:44:15] hit a nail, right? Like, you don't, you might just throw it like [00:44:20] never seen it before. It's something brand new. And that's how I view, view like ai. [00:44:25] 'cause it's so brand new. People are just, we're literally all experimenting with how do you [00:44:30] use this thing? With like the stuff that I've been doing and I'm looking at my kid and I'm like, [00:44:35] I don't want you to be, you know, rotting your brain just scrolling all the time. [00:44:40] and so my approach was how do you [00:44:45] use it to learn to surface what is like priority for you? [00:44:50] Right? And I think that's, that the same thing is, is applicable to leaders, [00:44:55] right? There's way too much information, a hundred percent. what is pertinent to [00:45:00] you? What is gonna actually help you in your one as your business function, [00:45:05] but also as you as a leader?

[00:45:06] Like, what are the things that you should be watching out for?

[00:45:09] **Rob Ott:** Finding that [00:45:10] on-ramp though is what I'm, what is what I think, you know, for everybody it's a different way, whether it's just [00:45:15] learning a prompt or learning how it's gonna transform their business or writing a better email. I don't know. I mean like, but [00:45:20] you know, getting that exposure is really important.

[00:45:22] **David:** Yeah. You have to play with it, start to, [00:45:25] to learn about it and then try to apply the things you're learning. Like it's this [00:45:30] learn apply cycle,

[00:45:31] **Rob Ott:** Multi loop. Yep.

[00:45:32] **David:** Because, but yeah. But if you don't do it, [00:45:35] then you're gonna let get left behind. And so just, I think the most important thing is to start with a [00:45:40] simple, something simple. Apply that, it. And then [00:45:45] once you start that cycle, it, it just keeps going.

[00:45:47] **Rob Ott:** Totally agree. Yeah.

[00:45:49] **David:** But [00:45:50] so I, I wanted just to say. Before we get back into the, the coaching stuff was that for my [00:45:55] son, I, I wrote a, where I created a writing app and basically I wanted it [00:46:00] to help him become a better writer.

[00:46:02] So that was my intent because all these people are [00:46:05] using it to write their papers for them. Writing your paper for you, [00:46:10] like you might as well just pay somebody some money to do it. It, it doesn't, it doesn't help you to grow, [00:46:15] to develop or to, to expand your thinking. Right? And so the way I [00:46:20] approached it was, what's good about what you wrote? What should you have [00:46:25] done differently? Here's the grammar mistakes. And then, um, [00:46:30] you know, talking with some other people, like looking at like, is this logical? Does it actually answer the question that was [00:46:35] trying to be answered? so the output then is not like, [00:46:40] here's the better paper. It's the output is like, this is how you should improve yourself.

[00:46:44] **Rob Ott:** [00:46:45] You know, there's a lot of models that I've heard, uh, and you know, it, it's funny because you can tell [00:46:50] that we're not settled yet, because you'll hear the exact opposite. You know, some people say Write it ugly [00:46:55] and just, you know, use the AI to polish it, you know, use it for the first [00:47:00] draft.

[00:47:00] Don't use it for the first draft. I tend like when I, because I use AI to help me with my writing and, [00:47:05] and, you know, not to write for me, but I will come in and say, here's my concepts. This is my first [00:47:10] draft. I, I like to write at ugly and just

[00:47:12] **David:** yeah.

[00:47:12] **Rob Ott:** something out, like get my ideas out. [00:47:15] And then, you know, I'll go through and reorganize maybe with it or, you know, [00:47:20] look to say, you know.

[00:47:21] **David:** Yeah.

[00:47:22] **Rob Ott:** Read this and tell me what you think, you know, [00:47:25] where's it weak? You know, where does it not make sense? I like having that kind of feedback. Um, but I don't, [00:47:30] I don't sit there and use it. Like, I don't tell it to write me an article about blah, blah, blah, and, [00:47:35] you know, just see what it comes back with and then put my name on it.

[00:47:37] Like, that's, that's not, that's, that's lazy. [00:47:40] Like, that's lop Like, that's not, it could be a good article, but it's still lazy. You know, like, it's still, you're not doing the [00:47:45] work

[00:47:45] **David:** Yeah. And I think I, I think there's a fine balance right between, and, and this [00:47:50] will be, you'll see, uh, you know, I think, what was it for you? There is a [00:47:55] term, right, that the AI is gonna expose the, every, the lazy leader,

[00:47:58] **Rob Ott:** Well, yeah. [00:48:00] I think that what you're gonna see, it's gonna expose a lot of laziness. It's also gonna close the [00:48:05] gap between the really high performers and the mediocre performers, because the high performers are [00:48:10] not gonna get super charged.

[00:48:12] They will get incremental benefits and they will get better, [00:48:15] you know, through using the tool. But I think what you're gonna see is a lot of people that are in that kind of [00:48:20] middle performance tier, they will close the gap with the higher performers by using ai. [00:48:25] And I, there's, there's, you know, McKinsey has a, a, a study that showed this.

[00:48:28] I think Gartner has a [00:48:30] study that kind of has also supported that. And again, we're early in the, in the [00:48:35] process of, of, of learning these things, but, you know, it's, it really is interesting of what it's gonna [00:48:40] do to, you know, to work expectations. I just think that, you know, it can be a really [00:48:45] powerful tool if you use it the right way.

[00:48:46] **David:** We're learning how, how to, how to do that, how to use it the right [00:48:50] way.

[00:48:50] I, I was just gonna say it's a lot of really interesting challenges for, for [00:48:55] leaders today, right? How do we use this the right way?

[00:48:58] **Rob Ott:** Yeah, and I, [00:49:00] I honestly believe that, you know, regardless of whether an AI bubble [00:49:05] bursts, um, or, you know, we dramatically change or we find a different balance point, the [00:49:10] technology's here, it's not going away. You know, like, we're not gonna go backwards. So, like, I, [00:49:15] I even like, and, and again, going, bringing it back to the coaching.

[00:49:18] We have to [00:49:20] encourage people to, to, you know, to, to learn, to try to, to [00:49:25] engage and to, like I say, it's on-ramping. It's like finding out how you can [00:49:30] start the process so that you can get more comfortable. And, you know, I I, I know one of your [00:49:35] guests said something very similar, uh, you know, get comfortable being uncomfortable, which is [00:49:40] something that I've lived with my entire life.

[00:49:41] It's like, but one of our, uh, one of our professors at [00:49:45] Columbia would always say that there's no comfort in the learning zone, and there's no learning in the comfort zone. [00:49:50] And so, you know, working through that, you just, you gotta, you gotta be, I guess it was less, I [00:49:55] think it was, he was, it was a really great pod that you guys did.

[00:49:57] It's, it's true. You just gotta, you gotta [00:50:00] kind of jump into the cold water and eventually you'll figure it out. Which is, again, if we're gonna bring it back to our [00:50:05] kids, like my, you know, I, if anything, I'm hopeful and I have total confidence. My [00:50:10] daughter is like, my youngest is amazing with, you know, technology and, and I think that she's gonna [00:50:15] do like the things that I, I was always good at tech, but the things that [00:50:20] I feel like, like, she's gonna pass me, you know, I, I, I mean, like, we're, we're hyper competitive [00:50:25] with each other, so I'm not sure I'm ready to concede just yet.

[00:50:27] But, um, I have confidence and hope and, and, [00:50:30] and faith that these, these, you know, this next generation is gonna do some pretty amazing things as I'm sure [00:50:35] our parents felt about us,

[00:50:36] **David:** that's. Yeah. I mean, that's what we wanna do is we, we don't want to [00:50:40] like push our kids down that next generation.

[00:50:42] **Rob Ott:** right.

[00:50:43] **David:** them up and leave them in a better place [00:50:45] so that they can go further and far further than what we've been [00:50:50] able to do. I was just thinking, in university, I used to work for a bank as [00:50:55] a, as a teller. They went through a software update. Okay. [00:51:00] Not even like a software changed, just an

[00:51:01] **Rob Ott:** Right.

[00:51:02] **David:** But the update was significant [00:51:05] enough that like some of the UI changed, some of the, the processes changed all, [00:51:10] all for the better, obviously. Right. But it was like, [00:51:15] a lot. Complaining about, like, oh, why can't we go?

[00:51:19] Why do we have to [00:51:20] upgrade? Why do we have to change? Like, I don't like what happened where I could do this [00:51:25] before, and now I have, it's all changed and I, [00:51:30] I'm just, I, I can kind of see you smirking a little bit. I you know, you've seen that, right?

[00:51:34] **Rob Ott:** Yeah, I [00:51:35] mean, that, that's a natural change function. And it's the, there's a, there's [00:51:40] a process that you go through and there's this really great infographic that I use when I'm trying to coach people [00:51:45] because there is a rear facing, you know, I guess, [00:51:50] mentality of what you're losing. And when you're at your worst and you're most challenged in a change [00:51:55] process.

[00:51:55] It. The only thing that can get you out of that is the focus on what you're [00:52:00] getting, where the future's gonna take you, and really kind of changing your orientation to be forward [00:52:05] thinking as opposed to what I'm losing and what I'm giving up. And that's cl, I mean like you're describing [00:52:10] a classic experience.

[00:52:10] Nobody wants to like, it was easy. I just knew where everything was. You know, [00:52:15] I could click here, click there, and boom, I'm more, I'm running now. I gotta click, you know, there and here instead [00:52:20] of, you know, so it's a little bit different. And when, and like you said, the ui, it was [00:52:25] probably different, but it was probably better.

[00:52:26] You know, I don't, I don't know the details obviously, but

[00:52:28] **David:** Yeah,

[00:52:29] **Rob Ott:** was an improvement. [00:52:30] You don't upgrade because you want to make people's lives miserable. Like, I mean, you're trying to make an [00:52:35] improvement and getting them on that orientation path to see that is really, [00:52:40] is that critical change component.

[00:52:41] **David:** And that's, and that's of also the concern, right? [00:52:45] Because again, organizations you have. IBM and you have all these [00:52:50] massive organizations like, you know, any, any large, large organization, right? [00:52:55] you're gonna have people who don't want to adapt and learn. And I was listening, I forget [00:53:00] who I was talking to, but they were saying like that there's been so much, so many companies have thrown so much money [00:53:05] into adopting ai, but the actual output [00:53:10] of like the investment into AI and, and what the re ROI on [00:53:15] that hasn't been significant. My, my assumption is like, [00:53:20] oh, it's, these people just haven't either one been taught how to use it. Like there's [00:53:25] no, like good onboarding training on how to use and apply the ai they're just [00:53:30] unwilling to. To learn that. And I wonder if, [00:53:35] if you are facing that with some of the leaders in that, the organizations, they're trying to bring it in, [00:53:40] but they're, they're having difficulty, like pushback from, or like just [00:53:45] the, a lack of comfortable where I am, I don't need this AI [00:53:50] thing.

[00:53:50] **Rob Ott:** I mean there, you know, it's, it's, it's kind of a stew of all the things you just said. I [00:53:55] mean, you know, there are people that are comfortable and that don't wanna make the change, you know, and that's, that's human nature. [00:54:00] Um, I think that, you know, there was the, I, I don't know if this is what you were citing, but there was a [00:54:05] McKinsey study.

[00:54:06] From early 2024 saying, you know, there was all this [00:54:10] investment and their boards were saying, Hey, we're not getting any ROI on this, it's been 18 [00:54:15] months. What's the, you know, what's the, what's the deal? And, and you know what a lot of that was, was [00:54:20] that was the leadership failure. And, and what I mean by that, and I, I know it sounds a little bit on the harsh side of [00:54:25] things, but they didn't prep their people, I don't think.

[00:54:27] So what we really saw was a [00:54:30] tremendous amount of personal productivity gains. Like I'm writing better emails, you know, I'm organizing my, [00:54:35] you know, I've got this thought partner. They didn't look at their organization, they looked at it as a [00:54:40] tool that I'm just going to buy and put into play and it's gonna make everything [00:54:45] faster, you know, more cost efficient, whatever your metric is.

[00:54:48] And I don't think they looked at, [00:54:50] again, going back to what you were saying, systems thinking like what are we, how are we working now? What is the, what [00:54:55] is the change in work that is, and how do you extract value and ROI from that? So [00:55:00] that's what I think you're gonna start hearing more and more about in the coming Yeah.

[00:55:03] Year. I mean, you're probably [00:55:05] hearing about it now, but. That's the, that's where we're gonna get changed. And, and all those [00:55:10] pieces, like, you know, I've, I've seen a couple of companies do this really well, [00:55:15] where, but the, they didn't even really touch the, the technology for the first, like three to [00:55:20] six months they were building up like a resilience reservoir for their people to get them [00:55:25] ready for this massive change in transformation that was gonna go on.

[00:55:28] And I'm studying a [00:55:30] little of that now, so I can't really articulate it. But like, that's really what I think is the big [00:55:35] component of it, because then when you put the tool in and you've re rethought work and you've [00:55:40] reorganized your systems, then like, that's when you know, like two plus two makes 10. You know, you're [00:55:45] really jumping ahead.

[00:55:45] **David:** I, I was just picturing like driving like a little Honda [00:55:50] Civic and then suddenly, suddenly someone dropped like an F1 engine into [00:55:55] that thing just like, what the heck do

[00:55:57] **Rob Ott:** Yeah. Right, right. You're growing [00:56:00] fast, but man, you know, you're gonna crash into something.

[00:56:02] **David:** So this has been really fun [00:56:05] conversation, but I wanna bring it back a little bit to, to the business side of coaching. [00:56:10] Right. So you said four year years ago you kind of, you kind of got back and [00:56:15] gonna take on like coaching more seriously. Right? What, what does that mean or what did that mean [00:56:20] for you?

[00:56:20] **Rob Ott:** Well, I'll tell you, and you know, I'm gonna tie it back to the identity [00:56:25] question that we were talking about. So when I stopped working and I left the corporate world, so to speak, [00:56:30] um, you know, I went through an identity crisis. I was like, who am I? Like I spent 24 years at [00:56:35] that, like, with that same group of people, you know, building that up.

[00:56:38] And I was like, who? Like [00:56:40] we used to joke. I like, I, I could, I could say something and we could get people moving in [00:56:45] direction. I couldn't get my kids to empty the dishwasher when I got home. So I was, and I'm not a command and control kind of person, [00:56:50] but I was like, this is a weird place to be. Like, you know, I didn't like, so [00:56:55] I went into the proverbial wilderness and said, what do I really love to do?

[00:56:59] [00:57:00] And, you know, I, I, I spent some time really thinking about it. You know, fortunately I had really good [00:57:05] self-awareness skills and, and what I settled on was the through lines in my career were solving [00:57:10] problems and, you know, uh, developing people. And so that's why I launched my [00:57:15] business as a strategic advisory for entrepreneurs and people that are building their business.

[00:57:19] So I do [00:57:20] consulting and then also, you know, my true love, which is really helping people [00:57:25] identify their, uh, you know, opportunities, problem, challenge, whatever it may be, and helping them knock 'em down. [00:57:30] So I knew that I could coach just because I spent my career developing leaders, [00:57:35] but what I didn't realize was, you know, there is an orthodoxy that goes [00:57:40] along with, you know, the, uh, the coaching, like the, the techniques, the, you [00:57:45] know, the different, the neuroscience involved with it.

[00:57:47] And, you know, people come to coaching [00:57:50] usually from two different directions, either the school of hard knocks and experience. You know, like a true [00:57:55] academic leader, l and d type of, you know, organizational development background. I was [00:58:00] never gonna be that second group.

[00:58:01] I was the first one. So I was like, how do I build that out? And so I'm [00:58:05] taking the experience that I got through my certification at Columbia. I'm gonna, I'm in the process of [00:58:10] ICF certifying right now, and that's really teaching me a lot of the organizational stuff that, um, [00:58:15] you know, that, that really helps me.

[00:58:16] I, I will go back. You, you mentioned earlier that you're, you're a le you were a [00:58:20] Lego person. You know, I, I can tell you, I know enough about myself that I [00:58:25] was, I was the kid who built Legos by basically reading the instructions, [00:58:30] putting all my pieces into their color piles, really organizing it.

[00:58:34] Even when I [00:58:35] cook now, I always have like, meal, like, I always have the spices prepped and everything else. It's just like, it's just the way I'm [00:58:40] wired. I knew that I was gonna have to learn about this before I really kicked off and went, [00:58:45] and so I took a little bit of time, you know, like learning about what I was good at.

[00:58:49] You know, [00:58:50] who I, who my, you know, ideal customers are. I went through the whole marketing, you know, [00:58:55] like building my customer profiles, outreach. Um, and then just, you [00:59:00] know, kinda launched from there. But you gotta just go and, and it just was in the last six to eight months that I [00:59:05] was like, I, I, I, all my Legos are set.

[00:59:07] I know where I gotta go. I just gotta, I just gotta get out [00:59:10] there and do it and, and not block myself or say I need to read one more book or, so [00:59:15] if I'm gonna give any, like, again, I'm not, I'm not one that likes to like necessarily lean on advice, but I [00:59:20] would just go with the go, just do it guys. If you're out there looking to get started, figure go [00:59:25] and, and paint the plane while you're flying a little bit.

[00:59:26] It's always a lot, a lot of fun when you're doing that too.

[00:59:29] **David:** I [00:59:30] think that

[00:59:30] **Rob Ott:** Mm-hmm.

[00:59:31] **David:** like one of the hardest things for some. For many [00:59:35] coaches, uh, I think you're, you're a little bit of like an edge case because you, you came up [00:59:40] a entrepreneur, right? So you, you've gone through those [00:59:45] paces and you understand like what it takes to build the business. But a lot, often, a lot of [00:59:50] coaches are coming from more corporate or more traditional backgrounds, right? [00:59:55] And so think that often what I hear, and I'd love to understand [01:00:00] if you hear this as well, is like, marketing. I don't like marketing. [01:00:05] Like I don't wanna be salesy. I don't want people to think I'm, I'm doing that sales [01:00:10] calls like, that was great, but you know, just whenever you're free, [01:00:15] just get back to me.

[01:00:15] Right? And so I, I think that one, [01:00:20] there's a fear of, of putting yourself out there and we often mask it as, know, I'm [01:00:25] not gonna be salesy, I just. They're afraid of actually just being in public [01:00:30] and, do, do you hear the similar things in, in the circles that you're in about those things?

[01:00:34] **Rob Ott:** I'm less of [01:00:35] an edge case than you would think. Um, totally resonates with me. Uh, you know, when [01:00:40] you, when you go from a really small outfit to, you know, being involved in three, [01:00:45] 3000, 5,000 people, you kind of lose that. That, that, you know, drive [01:00:50] to be the salesperson. You know, like even though that there's an entrepreneurial spirit to it, like I, and, and [01:00:55] to be honest with you, like I was always really good at being the guy behind the guy or the guy behind the [01:01:00] gal that made the stuff happen.

[01:01:02] So I didn't want to go out and sell. I was never, like, I, [01:01:05] I'm, you know, one of the worst things about me as a coach at times is there's, and I hope my clients don't [01:01:10] listen to this and hear this, but, you know, if you bought me a beer, I'd probably sit and, and do a lot of what I would [01:01:15] do as a coach, even if we just were talking and hanging out.

[01:01:17] That's always been my personality. So [01:01:20] making that transition to having a structured conversation, even if it feels na, like [01:01:25] to make it feel natural, but still have a call to action and try to get them to, to a sale, [01:01:30] um, that's, that takes work, you know, and it, it takes practice and it, you just gotta, again.[01:01:35]

[01:01:35] Like, get comfortable with that. Because it's not a comfortable spot for me to be in. I don't like to [01:01:40] necessarily go out. I like, I, I don't like to be a salesperson and I'm not knocking salespeople. It's [01:01:45] just the, it's, people have preferences and that's not one of mine. It's, it's, but you have to [01:01:50] cultivate that.

[01:01:50] Like, and, and I do go back to, so here's where I am, Ben. I do have a benefit, like [01:01:55] the entrepreneur spirit of, Hey, this is, you know, I know what the problem is. I gotta solve it. [01:02:00] Do I go out and hire somebody to help me do lead gen? Maybe do I, [01:02:05] you know, just knuckle down and do it myself, you know, that was my preferred path.

[01:02:08] I mean, I know enough [01:02:10] that I don't wanna pay necessarily to have somebody, but there are plenty of coaches that I know that are like, Hey, I'm gonna go [01:02:15] work for, you know, coaching like BetterUp or one of those, you know, organizations that does that and [01:02:20] handles that for them. Because if you, you know, if you, let me, if you ask me, [01:02:25] and I'm gonna be completely honest, I, I would love, I just love the coach.

[01:02:28] I love to just sit down and [01:02:30] talk to somebody. That's where I'm happiest. That's, you know, the other stuff is, is a [01:02:35] necessary evil. I mean, I don't want to like, maybe that's too dramatic. I mean, but you gotta do it to run a [01:02:40] business. But, but it's, it, it really is. It does require that. And, but [01:02:45] know that going in, you know, know what your strengths are.

[01:02:47] **David:** I, I would say that 95% of the coaches I've [01:02:50] spoken to exactly the same thing. They

[01:02:52] **Rob Ott:** Mm-hmm.

[01:02:53] **David:** They just want [01:02:55] to people and I that, and that's what I love about [01:03:00] coaches, right? They want to just help people. problem is that with. You [01:03:05] can only help so many people until you run out of money.

[01:03:09] **Rob Ott:** And so this is,

[01:03:09] **David:** [01:03:10] have to build a

[01:03:10] **Rob Ott:** so this is where the entrepreneurial piece comes in. And this is where I'm gonna lean back on my experience [01:03:15] because the, the company that we had, I loved being there and we [01:03:20] always, you know, we talked about every meeting, like I was very transparent with the finances of the company. And, you [01:03:25] know, you can't be completely a hundred percent transparent with everything but.

[01:03:29] We [01:03:30] wanted everybody to draw a through line from the work that they were doing to the revenue we were generating, because we [01:03:35] wanted to keep the lights on so we could come back and do what we love tomorrow. And that was a, [01:03:40] that sticks with me is like, yes, I love to coach, but I want to coach for the next [01:03:45] 10 years.

[01:03:46] And if I want to do that, you know, there's a part of me that's [01:03:50] gotta build the business. And, you know, even just feed the client bases, [01:03:55] like to keep that building and going. Because to be honest with you, coaching has a, you know, I don't [01:04:00] hire, people don't hire me to like, as, as lifelong coach. Like, you know, there's a, there's a, you [01:04:05] know, there's a transaction period.

[01:04:06] It's like, 6, 9, 12 months, whatever it may be, if I'm doing my [01:04:10] job right, there's an ending. You know, like, and yes, I love to stay in touch with my clients and my coaches, my, [01:04:15] my folks. But you know, if I'm still doing this two, three years later, [01:04:20] then you know, either we're recontracting and changing.

[01:04:22] Or we're not getting it done. There's [01:04:25] a trade off there that, that comes into play.

[01:04:27] **David:** yeah. The one pushback that I'd like [01:04:30] to give is you, you brought up like perspective, right? Like [01:04:35] talking about perspective, how you're looking at AI and business, right? I would say [01:04:40] your perspective on marketing and sales might need to, to have a [01:04:45] shift. And why I say that is because I, I realize it for myself [01:04:50] because same thing I like. To be the background guy in high school, I, [01:04:55] I liked to be on the wall

[01:04:57] **Rob Ott:** Mm-hmm.

[01:04:58] **David:** else, right? I [01:05:00] was the observer. I was the guy tinkering in the background doing, [01:05:05] the business and systems and processes. And what I realized for coaches is that the [01:05:10] mentality that you have about marketing is, now I have to go and sell myself.

[01:05:14] I gotta [01:05:15] be out there and be visible, and I have to like, and it's all this stuff I, I, I don't [01:05:20] like to do, which is true enough. But the fact is that even talking with you right now and talking [01:05:25] with every coach I've spoken with for this podcast, I could say that if they [01:05:30] were to work with somebody for six to 12 months, the people that they work [01:05:35] with, I would say probably 95%, 90% of the people would be changed through that [01:05:40] interaction for the better. Right. So if you take that premise of what you're [01:05:45] doing is gonna change somebody's life for the better. And I, and, and now I'm, I'm putting it in [01:05:50] this way, which is, so your ethical, you believe your work that you do helps [01:05:55] people. If you think that the work that you do helps people will improve their life, is [01:06:00] it not your, Responsibility then to try to help as many people as you can,

[01:06:03] **Rob Ott:** I like the way you're framing [01:06:05] it.

[01:06:05] **David:** Right?

[01:06:05] **Rob Ott:** I, yeah, it's, it's absolutely true. I mean, uh, and I'll tell you this, [01:06:10] like. I am a better marketer today than I was yesterday, and I'm gonna be a better one [01:06:15] tomorrow because I'm learning. And you know what I'm saying? And what I was mentioning earlier is that I just, [01:06:20] A, I, like, I, it's not, it wasn't a natural process for me.[01:06:25]

[01:06:25] So I'm in that uncomfortable, like zone of like learning right now.

[01:06:29] **David:** Yeah, so my [01:06:30] point is that if you turn the perspective of I'm just trying to like make money and get new [01:06:35] clients to, I'm trying to help people and the way that I help people is creating more exposure for [01:06:40] myself by talking about how I help leaders. That naturally leans into the [01:06:45] marketing that you can do if you, the way you approach it is from that perspective [01:06:50] of, wanna help as many people as I can. The way I can help many more people is by [01:06:55] creating more awareness about the work that I do. So I'm gonna go shout it from the mountain [01:07:00] toss and be like, Hey, you may not want this, but I wanna help you. This is how I [01:07:05] help you. And so then you just, you just start talking about it. you talk about it to [01:07:10] anybody who will listen. Because, you know, if you see a guy on the side of the road who's got a, you know, [01:07:15] who's bleeding, you are gonna be like, let me help you. But might be like, no, no, I'm [01:07:20] fine. I'm fine. Like, I'm okay. And you're like, but they don't know you're a doctor, [01:07:25] so they, they don't wanna accept your help. Most people don't know about coaches or coaching. [01:07:30] They don't, they don't know they need your

[01:07:31] **Rob Ott:** Yeah.

[01:07:32] **David:** So you have, part of it is you have to go out there [01:07:35] mark and, and talk about what you do so that they understand how you help [01:07:40] them.

[01:07:40] **Rob Ott:** Good point. And you know, that's, that's the gem I'm gonna walk away from with this [01:07:45] because, you know, like I said, I'm, I'm gonna be better tomorrow than I am today. I can't wait for tomorrow. Like, [01:07:50] that's a Joe Namath quote. Like, I, you know, I'm, I'm kind of flipping it on a ted a little bit, but at the [01:07:55] end of the day, you know, that's a really good frame for me to start to [01:08:00] shift my, my thinking into.

[01:08:01] And I, I appreciate that. I just wanna say that for sure.

[01:08:04] **David:** For [01:08:05] me, like I've been working in, in some form or manner in the this [01:08:10] coaching space for. 12 plus years, and I've just seen [01:08:15] many wonderful coaches and people after two, [01:08:20] three years are gone. They're not coaching anymore and they couldn't figure it out. And [01:08:25] so that is like, why not? Because the whole business thing, are [01:08:30] certain activities that if you set yourself and discipline yourself to do and you [01:08:35] approach it, then you should be able to, in most situations, be able to build [01:08:40] your business. The problem is that most coaches they don't want to do the marketing or [01:08:45] sales. They, they're not really sure what the roadmap is of how to do it, and [01:08:50] they're too busy doing the coaching to figure out the business development side of that.

[01:08:54] **Rob Ott:** You know, listen, [01:08:55] I've, I've seen it. You know, I've actually. One of the sadder parts of watching [01:09:00] my, my cohort in my, my circle. Like there have been people that have, have stepped [01:09:05] out, you know, or have gone back and have, you know, and I don't, I, I don't say that without any [01:09:10] judgment. I mean, maybe it was the best opportunity that came along that they left and went back to corporate world.

[01:09:14] But, you [01:09:15] know, I, I've seen people, you know, leave coaching and, and you're right, it's, it's [01:09:20] sad because every one of 'em brought something really amazing to the, to the cohort and to [01:09:25] their, I'm sure, to their clients and, and to the work. So, you know, I I, you are gonna [01:09:30] gimme new ways to think about this as far as even just ways I can tweak the stuff that I'm doing.

[01:09:34] I, I [01:09:35] will say that, you know, I like, I, like I mentioned, I'm not thrilled doing it, and it's, [01:09:40] it's a preference, not a, not a, like, you know, I'm never one to shy away from [01:09:45] something that's going to challenge me and help me grow because I, like, I, I, I do believe that that's, [01:09:50] you know, coach, coach Hill myself kind of thing is, I mean, really what, you know is, is the important thing.

[01:09:54] [01:09:55] So I appreciate you sharing that with me. I thank you.

[01:09:57] **David:** Yeah, no, I am, I'm happy to do it. I think [01:10:00] that that's, this is probably one of the things that will define the [01:10:05] work that I do with Mike, with other coaches, is helping [01:10:10] them to realize that is if you wanna help more people, you need to [01:10:15] build your business. And the way that you look at the business is, is really important.

[01:10:19] Like [01:10:20] you're not gonna do the marketing when you just hate the marketing, but if you can change your perspective on it [01:10:25] and to find the, the way to like, pull you forward,

[01:10:28] You're gonna be more motivated to [01:10:30] do it. and so, yeah, coaches are, they're not in it for the money, but they're in [01:10:35] it to help people. way you help people is only way you can help more people is by [01:10:40] telling them you're there, how you help them so that they can find you.

[01:10:44] **Rob Ott:** [01:10:45] Yeah, you're, you're absolutely. I, I, I really like that, you know, and I'm gonna, I, I, like, tomorrow is a [01:10:50] little bit of my marketing. I've got a couple hours devoted to marketing, and so I'm gonna, you know, bake [01:10:55] this in and, and see where it takes me.

[01:10:57] **David:** Just so to your business, [01:11:00] uh, how do you, like, do you separate then your, your time? Do you set like [01:11:05] specific days and, and blocks of time for your business development, like marketing and, [01:11:10] co contacting people, things like

[01:11:12] **Rob Ott:** It's played around with this. Um, and you know, again, [01:11:15] it all, it, like I, what works for me may not work for everybody else, but I kind of segment [01:11:20] my week and the first couple hours I, I have found through trial and error that the [01:11:25] first couple hours on a Monday are some of the best days for me to start engaging with leads, [01:11:30] doing any kind of social media like prep posting that I want to do, so that I can, you know, [01:11:35] drop them out, breadcrumb them out over the, the course of the week.

[01:11:38] Then, you know, then [01:11:40] I go, and by Monday afternoon and into Tuesday, Wednesday, Thursday, I'm usually [01:11:45] working on my, you know, serving my clients, doing my, you know, my meetings, [01:11:50] um, having my coaching engagements. And then Friday I really kind of close the week by [01:11:55] doing some AI learning. I, you know, I spend the first three hours on, on like, whatever, even if it's reading [01:12:00] or you know, just podcast, article, whatever, you know, whatever catches my attention.

[01:12:04] I [01:12:05] spend the first three hours just like, you know, I call that personal development for me. Uh, and then, [01:12:10] you know, Friday is by the end of the day on Friday's, like my reflection time and like, what did I learn this [01:12:15] week? What am I gonna apply? What am I taking forward? Does it always follow that schedule?

[01:12:18] No, I mean, like, [01:12:20] life, life has a way of getting in the way, but, um, and I'm in a customer service focused business, so [01:12:25] sometimes I'm coaching on Fridays, but generally speaking, I find that I'm better in structure [01:12:30] and, um, I like setting it up like that. I have to devote time to business development.

[01:12:34] Otherwise [01:12:35] it'll like, it'll just gravitate towards the, towards the other. I'll gravitate towards the other stuff.

[01:12:39] **David:** [01:12:40] Yeah. I love it. I think that discipline and structuring it makes it easier. You know, there's [01:12:45] the Atomic Habits book where it's just like if you set it up in a structure, then you don't [01:12:50] really need to think about doing it. You just, you have your time, you just do it right. [01:12:55] And that's probably one of the other things that is a lot of coaches don't do is [01:13:00] necessarily set that time regularly to do it.

[01:13:02] **Rob Ott:** Yeah. And I, I think a big function for [01:13:05] me, uh, you know, David, to, to kind of, you know, like really also add to that like a [01:13:10] yes and is to really understand where my energy was. 'cause that's what I'm, I was trying to do those on, on the business [01:13:15] development on Fridays and knowing that it wasn't something that I naturally fell into [01:13:20] and knowing that I was gonna have to summon energy, like Friday midday was not like the best time of the [01:13:25] week for me to, to tackle.

[01:13:26] And that's, that's me. So that's why I said I'm shifting this to Mondays [01:13:30] 'cause I'm gonna eat the frog or whatever the, you know, whatever the saying is is like, I'm going to, I'm gonna do [01:13:35] it, I'm gonna commit to it, I'm gonna get it outta the way and then I'm gonna, you know, and then if I wanna do more on Friday, [01:13:40] that's great, but I'm not like doing it when I'm, my energy's outta low E.

[01:13:43] **David:** yeah. No, I, I, [01:13:45] I love it. I think that's super important. We've been talking for a lot longer than I expected. [01:13:50] Um, so before we close, uh, I'd love to ask, I have a couple of questions [01:13:55] I asked before closing. First is what have you learned about yourself, uh, [01:14:00] through this process of becoming a coach and coaching?

[01:14:03] **Rob Ott:** I have learned, I think I'm [01:14:05] probably gonna go to a callback to what I was saying earlier is that, I am an not, uh, I'm not an [01:14:10] experiential learner. I am more of a book and process learner. So like, when I'm [01:14:15] in that and, and, you know, I went through some, got some assessments done and, you know, understood how my [01:14:20] brain works and processes just through the use of that.

[01:14:22] Like, I like to have things organized [01:14:25] and I know that I'm at a point where I've gotta jump and go when I've, when I've read [01:14:30] enough. Like it's a confidence building thing. And so what I realized is I gotta build the [01:14:35] time in to give me that, and then also kick myself in the butt to get me outta that safe zone.

[01:14:39] [01:14:40] Because, you know, again, there's a, there's a diminishing return on every book and article you read. Like at some [01:14:45] point you know it and you just gotta do it. So that was something that I did learn going through this.

[01:14:49] **David:** [01:14:50] Um, and what's one piece of advice that you'd give to somebody? Somebody who's [01:14:55] just beginning their coaching journey?

[01:14:57] **Rob Ott:** Wow. There's a lot. I mean, I think it's, [01:15:00] it's be a friend to yourself. Don't be too hard on yourself, like give [01:15:05] yourself the space to learn. Um, it's an organic process and you just, as you [01:15:10] said earlier, you're gonna do a lot of good for people. You know, generally speaking, coaches come in with a [01:15:15] good, great intentions and good heart and, be patient with yourself as you're learning this process, especially if it's [01:15:20] a new transition you're making in your life.

[01:15:22] **David:** Rob, thank you so much. Uh, [01:15:25] before we close, how can people get in contact with you?

[01:15:28] **Rob Ott:** Uh, you can reach me on LinkedIn. [01:15:30] That's probably one of the best places to, to find me. Um, you can also connect with me on my [01:15:35] website. It's o tt mgt.com. So www.ott [01:15:40] mgt.com for op management. Uh, and then, you know, that's, those are probably the two [01:15:45] easiest places to get a lot of info about me. And then there's links that you can directly connect with me through both of [01:15:50] those places.

[01:15:50] **David:** You also have a substack.

[01:15:52] **Rob Ott:** I do, I do. It's the spark of leadership. Thank you [01:15:55] for bringing that up. Um, and that's where I do some, uh, writing and exploring on leadership and [01:16:00] ai.

[01:16:00] **David:** Right. Very cool. We'll have all those links in the show descriptions. [01:16:05] thank you so much for this, uh, conversation. It's, it is [01:16:10] really a lot of fun exploring AI leadership and to know you

[01:16:14] **Rob Ott:** [01:16:15] Yeah, it was a thrill. I really appreciate it. And thank you for taking the time for me and I love the work you're doing, David. And [01:16:20] keep it up. I.

[01:16:20] **David:** All right. Thank you, and we'll see you guys next time.

[01:16:23]