The Career Rule That Took Him From Bagger to 3-Time CIO | Ep. 405 with Harrison Allen Lewis Founding Partner at Jacob Meadow Associates

8 Jun 2026 · 36 min · 16 chapters

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In short

Harrison Allen Lewis (founding partner at Jacob Meadow Associates) shares how he rose from grocery “bagger” to a CIO, and argues that leaders should create clarity and accountability, match people to roles through strengths and training, and communicate outcomes/strategy/plans—not just tasks.

Guest background

Lewis worked multiple grocery roles through college, later moved into management, then leadership/consulting and CIO roles. He’s led major technology transformations (e.g., moving an entire data center to Google Cloud; rebuilding reporting on AWS) and has advised organizations as a consultant.

Key claims

Fear is not a reason to say no; opportunities require saying yes. Organizations fail when they “do things with people” instead of “to people,” and when they promote without aligning strengths or providing retooling. Leaders must understand outcomes/strategy/plans to avoid owning failed execution.

Notable examples

a bomb-threat incident where a manager handed him keys to handle a crisis; being promoted without training and having to replace misaligned managers; entrepreneurship differentiation (“X factor”) and value creation; worst CIO days when initiatives were not feasible or outcomes were missing.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Lessons from Management Experiences

0:10 to 0:40

Harrison shares impactful lessons learned from challenging managers.

“I've learned some of my best lessons from dealing with horrible managers and being observant.”

A Critical Lesson from a Bomb Threat

0:40 to 2:38

Harrison recounts a pivotal moment involving a bomb threat and accountability.

“So Harrison, I was just thinking about this recently.”

Promotions and Proper Roles in Management

2:38 to 5:45

Harrison discusses the importance of matching skills with job roles in management.

“So I really felt like this guy, that this person believed in me.”

Engaging Employees and Responsibilities

5:45 to 9:48

Harrison emphasizes the importance of engaging employees in their roles.

“So I tried to help all these people get into other roles.”

The Secret to Success in Business

9:48 to 14:00

Harrison discusses the strategy needed to stand out in a competitive market.

“I'm going to do everything in our power to ensure that you are successful, but it is up to you, right?”

The Importance of Differentiation in Business

14:00 to 16:43

Learn why identifying your unique value proposition is crucial for entrepreneurial success.

“what's the environment of entrepreneurship?”

Understanding Tools for Creating Value

16:43 to 17:49

Discover how understanding the tools at your disposal can enhance business effectiveness.

“I think the other thing is, is that understanding the tools.”

Common Pitfalls for Businesses

17:49 to 20:02

Explore common mistakes companies make and how collaboration can help overcome them.

“Like I know so many people that have gone out of business because the problem that they had, no one was willing to pay for that problem.”

Navigating Challenges as a CIO

20:02 to 22:34

Insights into the toughest days and lessons learned from experiences as a CIO.

“And so a lot of what we do is really about bringing all of that together.”

The Loneliness of Leadership

22:34 to 24:24

Understand the unique challenges and emotional burdens faced by leaders in the C-suite.

“And it's like, I just need you to execute.”
Show all 16 chapters

The Role of Mentorship in Leadership

24:24 to 26:04

Learn how reciprocal relationships and mentorship shape effective leadership.

“You can't tell your employees, I would think, everything, of course, right?”

The Balance of IQ and EQ in the Future

26:04 to 28:00

Discuss the evolving importance of emotional intelligence over traditional IQ in leadership.

“And, you know, and I don't, and I think that will always be the case.”

The Butterfly Effect in Career Choices

28:00 to 29:43

Explore how pivotal moments shape career paths and life decisions.

“and the thing is that it it has that information and so as a result i'm able to call pull on that pull on that information and readily available and it allows me to then be able to kind of gauge at a much higher level.”

From Bagger to Management Training

29:43 to 32:40

Learn about the journey from a bagger to exploring management training opportunities.

“And the thing that, that, that really was that, um, I, I ended up, uh, I started off and I was working in a, in an ice cream shop.”

Embracing Opportunities and Overcoming Fear

32:40 to 34:58

Understand the importance of saying yes to opportunities despite fear.

“I went through and I went into the corporate office.”

The Power of Belief

34:58 to 35:23

Discover how others' belief in your potential can transform your career.

“Because the reality is someone believed enough in me to be able to say Harrison is capable.”
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Transcript

Automatic transcript. May contain errors.

0:00Doors are going to open, opportunities have been opened, and you have to say yes, unless you have a good reason to say no. Fear is never a reason. Harrison Allen Lewis, founding partner at Jacob Meadow Associates, from fearless bagger to fearless CIO. I've learned some of my best lessons from dealing with horrible managers and being observant. The store manager comes up to me and he says, Harrison, someone called in a bomb threat. And instead of me dealing with it, he said, I went over and I handed you the keys. But the thing was I learned from that was about accountability and taking responsibility and being put in a situation where you've got to make tough decisions.

0:40That changed my entire life.

0:50So Harrison, I was just thinking about this recently. I had this experience when I was an assistant manager and my store manager I had was the worst manager. He was terrible and never believed in me. I remember he went on vacation. I wanted to prove him right that he'd made the right choice in me. So I did amazing results. He came back and he just berated me on why I didn't do paperwork. And I'll never forget that. The lessons I learned from him and these horrible managers, I think maybe stuck with me even more so than the managers I had that believed in me more. Why do you think that is? And what has been your experience around lessons from horrible management?

1:37Yeah, I've learned some of my best lessons from dealing with horrible managers and being observant. And, you know, I've had quite a few, but one that really sticks out to me is that I had a manager that I was working throughout college in a grocery store. And, you know, and I was doing I'd done all the different roles in the store. And one of the managers, the store manager comes up to me and he says, Harrison, kind of looked kind of he looked strange. And he came to me and he said, Harrison, I'm going to go down the mall for about about an hour. and I'm handing you the keys. Take care of everything.

2:16Oh my goodness. I was so, so incredibly excited, right? I thought this guy believed in me. So I go and I take the keys and I clip them on my belt and I'm walking around the store and I'm making sure everything's in order and everything else. And it was great. So then about an hour later, he comes up and he says, how's everything? I said, everything's fine. And so he says, okay, can I have my keys? I gave him the keys and walked off. So I really felt like this guy, that this person believed in me. So about, uh, about six months later, he was terminated and they had, you know, they, the way they terminated their district manager would show up and he asked the store manager for the keys and they would take the keys.

2:56And then another store manager would show up. So this guy was terminated. So about six months later, I'm in the store and I'm working and I was going through college and this manager comes to me and he comes up and he says Harrison how have you been I said I've been doing well I how have you been he says uh he says fine he said I've got something to share with you and I said well what is that he says you remember that day that I came to you and I told you that I uh I had uh you know I had to go down to the mall and said yeah I said I was really you know I was really you know I really felt made me feel really good about that he says He said, well, you know, I'm an alcoholic and I'm in AA now.

3:37And I have to kind of make things right. So I got to tell you what happened. I said, well, what is that? He said, well, what happened was someone called in a bomb threat and said a bomb's going to go off. And instead of me dealing with it, he said, I went over and I handed you the keys. And I went down the other side. I went on the other end of the mall. Right. That point, I was completely, completely deflated because all this time I thought that I had one view of it. But the thing was I learned from that was about accountability and taking responsibility and being put in a situation where you've got to make tough decisions and owning it.

4:19And I remember that for this very day. And so just like every other situation when I've dealt with bad managers and I observe and I've learned from them and I think it's benefited me in ways that it would be impossible had I not had that experience and only been working with good managers. It reminds me of a time when I took over a new state when I had been promoted. I was a store manager now being promoted to regional manager. I didn't really get any training and I was quite young. I come in, there's all these managers who are older than me who have been in the market for a long time, think they deserve the position over me.

5:03right and then i realized that over like as i analyzed them they were not even in the right positions and so now i'm tasked to basically fire them because that's kind of the corporate way right like you go in you clean something up if it's failing you fire people and it got me thinking at that moment like i probably wasn't suited for the job because i didn't know what the heck i was really doing. They weren't suited for their job. But instead of people looking at what is your strengths and skill sets and putting you in a job that fits, they just throw you in these positions or put you in these roles.

5:42And it just got me wondering, like, there has to be a better way. So I tried to help all these people get into other roles. And they were always mad at me, because I didn't promote them within, I moved them to a different department. But the whole point was, I'm like, they didn't know that I was about to fire them. How do you what do you think about companies that are so hyper focused on on this, like promoting people, moving people, but not putting them matching to the actual strength that they have or even teaching them the skill that they need? Yeah. You know, I think about it and I've got I've gone into a lot of situations, you know, as you know, as a consultant in the business, as well as as a as a CIO and other leadership roles.

6:31And you're going to the in these situations. One of the things I've learned is really that it's being putting people in a place where you're doing things with them as opposed to to them. And so it's really about being able to have them have a clear understanding of where we're going and why, right? Without kind of thinking about it in terms of their current roles and things like that, right? Because people are really, really able to make tough decisions, right? And I mean, they're very resilient. Right. You think about that in their personal lives, they're making decisions about, you know, their mothers and their fathers and about children and about purchasing homes and cars and, you know, death and life decisions.

7:17They're making those decisions. And so the idea that they can't, they're incapable of making decisions and dealing with problems at work is I think is very flawed. And so what I do is I think about it as saying, OK, this is where they are. I'm going to say this is where we're going, where we need to go, and here's why. And then engaging them in terms of making it very clear to them in terms of what that is and what they represent in terms of the roles and responsibilities. Right. And then engaging them and saying, OK, let's talk about the things that you have an interest in and are the things that you don't have an interest in.

7:55And what is the gap and what is going to be necessary for you to be able to transition into those roles? Ultimately, what happens is and what I've seen is that people will make that decision. They say, you know, look, I'm not interested. I'm not interested in being retooled. and I'm, you know, thank you, but I'm going to leave. You have others that say, you know, I'm going to be, I'm interested in this, and boy, I don't know if I'm going to be successful. And what I say to them is that if you're interested, and I'm going to do everything, and you're interested. If you've ever watched this show, you know I travel constantly, and here's something nobody warns you about.

8:33The internet you have at home is not the internet you get on the road. I'll be in another country trying to get on a site we use for media interviews, and it's blocked or I want to unwind at the end of the day and my favorite shows won't load because of where I am. The internet isn't nearly as open as we think it is. That's why I started using ProtonVPN. It lets me change my virtual location so I can get to the sites and the content I need no matter where I am. And just as importantly, it keeps what I'm doing online private, which matters when you're on hotel and airport Wi-Fi as much as I am.

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9:54We're going to identify the gaps. It's your responsibility to bridge those gaps. And when you do so, we're going to let you know along the way and we're going to celebrate your successes here. And then you have others that kind of say, I'm going to do a wait and see, you know, and see whether this comes to pass. I've had situations where, you know, some people have come to me, where I've had people come to me and they left the organization after they kind of did the wait and see. And then they said, they came back to me and said, you know, Harrison, when you said this is where you're going as an organization, I thought you were crazy.

10:33You know, I didn't think you'd be successful. I didn't think that, you know, that you as the team would be successful and you were, right? But it is really about being able to do things with people as opposed to doing, you know, to people, you know? And I think that's where organizations, they're making a mistake now, you know, in the way that they're approaching these. And so people are surprised. There's so much uncertainty and things like that, you know, and I'm upfront with it. I deal with clients. I did that just today with a client. And I said, here's kind of what that looks like. Here's what we're recommending.

11:14And the client, one of the individuals in the client says, whoa, whoa, whoa, whoa. What does that mean for me? I mean, right there, but among all these people, right? Well, what does that mean for me? Well, let's talk about that. and, you know, leaning into that and talking about it. And then this person said, you know, yeah, I get it. And now the responsibility is an elevated role. Here is what that looks like, you know. And everyone could hear that and understand that. But it is really being very, very, I think about it in terms of being transparent. I think in terms of being authentic, being candid, and coming from a place that people are resilient and very capable.

11:59It reminds me of this phrase I heard that your employees or people want to feel celebrated, cherished, and embraced. And that resonated with me for a long time. Basically going off what you said, you mentioned that people were surprised of the success that you would have Because you have this sounds like a grandiose vision where many people don't. Right. They're kind of like siloed in a box tunnel vision. They can't see the huge, giant picture that you see. What do you think was like the secret sauce to the successes that you've had? Well, you know, I think that it is something very often that there is situations where there is the grand vision, but it's not being communicated.

12:43OK, because they because they can't handle it. Right. I think there's also where, you know, it's not a matter of thought out. And so I think about it in terms of, you know, what is the outcome? What's then is the strategy? What then is the plan? And then, you know, and you're walking that through. And so being able to kind of craft that all the way through, okay, what is the outcome? What's the strategy to achieve that outcome? And then what is the plan? And then, you know, clearly about, you know, then what are the kind of the capabilities that are necessary to unlock, you know, that outcome, right?

13:25And then you got into it. And then the technology is the piece that all kind of follows. But it really is like thinking about that from a standpoint of strategy, you know, and then the outcome, strategy and plan. And I think what happens is, is that very often people will think about it purely from a standpoint of plan. And you have a plan that's not anchored in strategy. That's a problem. And if you have a strategy that's not anchored in outcome, then that's a problem as well. And everyone needs to understand all of those pieces in order to be able to engage. Someone just yesterday was asking me, how do I feel about entrepreneurship now that there's so many converging technologies, but not just converging?

14:09They're at such an advanced place. what's the environment of entrepreneurship? And I told them, it's like everyone can create an app very cheap or they can create things. They can build things, create things. They can do a lot of things within a business for very inexpensive, leveraging the million AI tools. At the same time, everyone can do it, which then creates, I think, a massive amount of competition. And I was telling them the number one thing you have to do is what makes you different. And I know you talk a lot about companies finding their X factor, which makes them different. How can someone right now figure this out?

14:52Because I think it might be the single most important thing that people do for their business. You know, I do think that it is about being able to think about it as a business. And a business ultimately needs to be creating value, you know, and it needs to make money. And it needs to be something that people are willing to value more than their money. So if what you come up with that it's valued to the extent that someone's willing to say, I'm going to give you cash in exchange for this thing, that's what you want. And so I think it's important that entrepreneurs really think about it from that standpoint is, what is that thing that's going to create the value, what's going to create value?

15:43What is missing yet needed? And I think that in this day and age, it is really, really great because you can do a lot of the things that represented impossibilities in the past, right? And so it's really about, you know, and a lot of these jewels are in these areas that, you know, people have looked at and said, well, that's impossible. You know, that can't be done. And they set it aside. Right. This is the opportunity to really rethink all of that and say everything's on the table, you know, and really think about, you know, what are the things that are going to create value? and then how do you then leverage what we're capable of today and what we will be capable of in the future.

16:30When we talk about future, it is not, you know, in a matter of years. We're talking about in months, you know, of how this is happening. But it is about, you know, being able to identify that and it really comes down to the differentiation. I think the other thing is, is that understanding the tools. And, you know, very often, you know, it is really understanding the tools. And so I think about it, you know, an analogy would be, you know, a painter, right? And a painter has, you know, brushes and they've got paint and they've got canvas and everything else. But the thing is, is that someone behind them created those, the paint.

17:11Someone created the brushes. Someone created the canvas. And each of those, the brushes and the paint and the canvas all have unique properties. And it's important to understand those unique properties in order to be able to be the most effective as a painter. And the same thing goes true for entrepreneurs that are living in this age today. It's important to understand the tools and then being able to then leverage those in terms of identifying those areas that are going to create value that people want to pay for. Oh, my God. I don't think people understand how important that is. Like you're saying, I might have a problem that I'm solving, but if no one is willing to pay me for that problem or more than the problem might cost, like if it costs me$10 to solve the problem and I sell it for$5, then I'm negative, right?

18:05Like I know so many people that have gone out of business because the problem that they had, no one was willing to pay for that problem. And they didn't think that through in the beginning. So it's critically important. What else do you find? You've worked with so many companies. What else do you find is like a gigantic miss that these companies have that's might it might be a common thread? And then how do you solve that? I mean, I think that if if you bring people together and they are able to kind of work together onto a common problem, and it's not necessarily from a standpoint of, you know, that they are coming forward as as as as business people, you know, to solve a problem.

18:48But so often what happens is everyone walks in and they're wearing their hat, their area of responsibility. And so that is the thing that leads. And so what will happen is, is that they either are excluded from the conversation and the opportunity to be able to engage in that problem or helping the organization realize on the opportunity. They're excluded because either they're carrying that badge, this is who I am, and they're walking into there, or they're excluded because this is the badge that they hold, right? As opposed to saying, I'm a business person first. I care about this business. I understand this business.

19:35And then I can engage in this level. And then what I can do is to then take the discipline, my knowledge, my experience, and things like that, and engage in this problem, this opportunity, and be able to also defer to others is important as well. Uh, and, uh, I think that's, that's, I think that I see there's a, is a, is a big missing. And so a lot of what we do is really about bringing all of that together. You know, we, we come forward with a lot of, you know, best practices and, and, you know, methodology and all this other stuff. But the fact is, it's about being able to bring people together and collectively kind of understand what the outcome is, understand kind of what the strategy is, understand the plan, and then be able to engage in that in a way that is aligned.

20:33And I think that is so incredibly powerful and important. So you've done things world first, such as when you moved an entire data center to Google Cloud, swapping out POS systems, rebuilding reporting on AWS. Obviously, things I'm guessing worked out well, but they might have not. You're doing things that could potentially almost destroy the business if it goes wrong. What was the worst day you had as a CIO? Well, I've had a few. I had one where I had gone into an organization and they brought me on and they said, hey, here's where we are and everything else. And this happens to, I think, a lot of people.

21:23And they said, well, here's where we are, here's what we're doing. And what we need to be able to do is execute that. right and i looked at it and i i was there about two weeks and i said there is no way i mean they've been working at this for you know a year year and a half saying they're ready and so on so forth and i looked at it and and i said there's no way and in order to be able to to address it it was going to take, you know, time and it was going to take a lot of money. I turned in a new person in the organization. I was, I had probably in a matter of about a month there, I probably became the most, the most aided person there because they, you know, everyone was like, you know, you made this happen, right?

22:14I'm like, it wasn't going to happen regardless. I just basically, you know, called it as it is right and now here's what needs to happen and so we were able to you know engage and everyone engaged and and you know for their first thing was okay well you fix it you know you tell us how to fix it it's okay well here's what the strategy and the plan and so on and so forth and then people kind of you know got engaged and everything else and then and then and we were fine um the other is is that you know you i've stepped into situations where you know the play The strategy and the plan has been set.

22:47And it's like, I just need you to execute. And that was a huge lesson learned for me. And like, no, under no circumstance. Because I have to understand the outcome. I have to understand the strategy. I have to understand the plan. I have to understand how we got here and not be in a situation where I'm asked to execute because at that point you own it, right? And you own it and you're held at, you're accountable for it. And so those are, you know, really, really tough, you know, those are tough times and tough days, you know, when you're having to do that. And then also being in a situation where you are asked to execute something that in itself, the outcome was absolutely, absolutely not there, you know, even after asking the question, well, what is the outcome?

23:43Well, no, it doesn't matter, right? We're just doing technology upgrade, right? Okay. Sometimes you got to tell people the uncomfortable truth. Right, right, right. But it tells them what they don't want to hear because everyone else is yesing them. That's why you're hired in the C-suite, I imagine, because they need this different perspective. So I think when you're in that position, it could be a lonely place. Just like many people say, you know, being in business can be very lonely because you don't really have a lot of people around you or people that even really understand. When you're in the C-suite, you kind of have to put on this persona and face.

24:24You can't tell your employees, I would think, everything, of course, right? Like, you have to be the shining light. You have to be the guide. In the moments when you had fear or doubt, who would you call? You know, I've always kind of surrounded myself with colleagues and mentors and people that, you know, it was reciprocal. It wasn't one way. But understanding that, you know, and being able to have people that you can call on that have been in that situation, others that are kind of calling on you. And so it is all very, very reciprocal in being there. You know, I think about it in terms of giving back, you know.

25:06So for me, it is, you know, where I am and who I am is as a result of people, you know, that they invested in me. Right. And so as a result, I have a responsibility to give back. It's a responsibility. It's an obligation. But it's also then surrounding myself around people who think in kind, that think the same way, that where they are is because someone invested in them and they have a responsibility to give back. And so that's what I try to surround myself with, as opposed to those that have other motives. And it's important to be able to have that audience. Very often, it's a sounding board.

25:57I can tell that you are very intelligent. And you have a lot of experience with technology. there's a big debate now around is iq gonna even matter in the future is eq more important or do i don't does none of these even matter but what do you think around the does will iq really matter in the future well i think that that eq absolutely matters and even even more so but i think also and you know this this whole thing around you know it's it's so much about people. It is so much about people. And, you know, and I don't, and I think that will always be the case. I think that we got into this thing with COVID and some of these other things that gave us this impression that it really wasn't the case, but it really is about people.

26:46And I think that will always be the case. And it's so incredibly powerful when you bring people together and they're relating. I think the other side of it in terms of IQ, with so much of this happening in terms of what's capable in terms of technology. I find it actually, personally, it's a relief because I'm able to then leverage the tools and the tools are doing a lot of the things that are the repetitive and kind of the heavy lifting. And then I'm able to kind of elevate up. I'm able to spend more time on more things that are more significant, right? And so I think it actually has made me much more intelligent.

27:39You know, I'm not having to remember kind of the minutia. You know, we do this thing. We have this thing called the ledger, which is our knowledge base, right? And it's on this rag. but you know we commit all these things to it and the thing is is that i don't have to remember all these things i you know i do i can remember but there's things that i don't necessarily remember and the thing is that it it has that information and so as a result i'm able to call pull on that pull on that information and readily available and it allows me to then be able to kind of gauge at a much higher level. So I think it gives the perception maybe that I'm more intelligent, you know?

28:27But I do think I'm able to spend more time on things that really, you know, really matter as a result of leveraging the tools. People sometimes think I'm really smart. I'm like, I'm probably like 85 IQ. I don't know. I think I was like, you know, 200 or whatever. I'm like, it's AI. Believe me, it's AI. I like to really ponder on the butterfly effect in my life. Like I can go back 30 years and say this moment in my life, that moment led to this moment to like, you know, like I could go all the way up. It's like, wow, if that moment didn't happen, I would not physically be here. And something for me was dropping out of college.

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29:08And I could even go back to high school. I failed miserably in in classes in high school, I did poorly, which then led me to only getting into this crappy college, which then led me dropping out after a year and a half because I was miserable, which led me to working in a mall. And in that mall, I met someone who I then moved to another state and opened up my first business. And I think back to like, if I did it too poorly in high school, I never would have been there, which then I met my wife and then led me to here. What was the moment like that? trace back in your life when you think back to maybe one or two moments where you're like wow this moment put me on this path i never would have thought possible and that's why that that's why i am here right now you know i was in uh i actually have gone through this i did this exercise for uh a uh a group that i was presenting to uh about two months ago um and um and uh of these students and I was kind of telling them kind of my, you know, the, the, the breadcrumbs.

30:10And the thing that, that, that really was that, um, I, I ended up, uh, I started off and I was working in a, in an ice cream shop. And I was doing that as I was a Baskin Robbins ice cream shop. I was a super scooper. And I went through and I was, or I was working there and I was in, in high school. And a manager comes into the store. He was a Kroger manager. He comes in the store and he hands me an application. And then he says, hey, I'd like for you to work for me. I kind of put it in my pocket. I didn't throw it away. I put it in my pocket and I left it. I ended up not, I lost it somewhere. So he comes back again.

30:49He says, hey, I've got this application. I'd like for you to fill out this application. I'd love for you to work for me. So I took the application. I filled it out. I took it over to the store. I got the, you know, I got the job, started out as a bagger. I did all these different roles in the company. They paid part of my scholarship throughout college. I worked through the college and everything else. And then I decided, you know, it's time for me to leave. And then they told me, hey, we'd like you to think about the management training program. So I thought, no way. You know, I've been a part of the union and I was a shop steward at one point.

31:31It was this dreaded manager thing. And I said, look, I've got this offer from CNN. I graduated with MIS. And so I said, I want to go. I'm going to pursue the job consistent with my education. And they said, well, look, why don't you just do this? I mean, just, you know, it's great training. It's a great training program. And you think about it, that it would just be resume thought of. I mean, you know, it's just not going to help you. It's not going to hurt you. You're early in your career. Now, I remember something my father told me. And what he said was, you know, that he said, doors are going to open.

32:17Opportunities are going to open. And you have to say yes, unless you have a good reason to say no. And fear is never a reason. In fact, fear is the thing that should tell you that there's something here, you know. And so I thought about that and I said, yeah, I'll do it. That changed my entire life. It gave me the ability to be able to understand the business. I worked in the business. I worked in managing stores. I went through and I went into the corporate office. I, you know, moved from, you know, then I had this thing where I moved from Atlanta to San Antonio. with a completely different company, completely, I didn't know, had no idea who they were.

32:59I was in Texas. Again, one of those situations where there was this fear, right? And I, in spite of it, I said yes. And I, and I took that and had great, great opportunity. It was a wonderful, wonderful opportunity with, with H-E-B. And then, you know, but everything has been that, that way, you know? And so it's about, it's been a series of things building on one another. And it's about this fear and these doors that open and then saying yes to them, you know, and not being so rigid, you know, on it. I did this thing a while back as a part of the Society of Information Management. I did this career path and I was going to go in.

33:40I was going to be, at that point, I was an enterprise architect. I wanted to be an enterprise architect, you know, being able to do a green field. I want to then go be a CTO. And then I wanted to be a CIO. I was interviewing for a enterprise architect position in New York. No one would hire me. No one. And I was asking, well, what's going on? Why? And they said, we think you're overqualified. You won't do it. You won't stay. And I said, well, what do I do? So I had a recruiter that told me, he says, look, start interviewing for a CIO position. And I said, well, but I'm not ready. He said, well, but at least you'll learn what they're looking for.

34:17Right. And I was like, okay, I started to be in for a CIO position and I get an offer. Right. And I'm looking at this. I'm like, hold on, hold on. This was my career path. And I'm, you know, I'm supposed to do this, this and this and this. But the reality is, is that I get this offer and now I'm in a CIO seat. And now I'm thinking, okay, well, what, what the hell, what do I do now? What's, what's next? Right. And so the thing is, is that being so rigid about these things is a problem. And these opportunities that present themselves, being able to see them as an opportunity and then being able to then out of that fear, being able to step into those opportunities.

34:58Because the reality is someone believed enough in me to be able to say Harrison is capable. There's not anyone walking around saying, I have something here that I need to accomplish, and Harrison is incapable, and I want to watch him fail. I want to put him in this situation, but they can fail. No, it's not the word. They saw something in me that I had not yet seen in myself. It's powerful. From fearless bagger to fearless CIO. That's a good one. Harrison Allen Lewis, founding partner at Jacob Meadow Associates. Harrison always great to talk to you I learned a lot I learned a lot and I and I love a lot of good quotes in there fear no fear saying yes I mean how many opportunities do we miss because we say no but I really like I'm gonna dig in when I have fears in the future I'm gonna say what would Harrison think I'm gonna dig in there's something like you're saying there's something here that's why I fear it there's something here that's why I fear there you got just made up a quote by Harrison.

36:03This has been great. Thank you for joining us inspired by your journey. And I'm so grateful that I got to hear it today. Well, thank you very much. I so appreciate it.

From the publisher

Daniel and Harrison Allen Lewis break down why the best leadership lessons often come from terrible management, and why clarity beats charisma in modern organizations. Harrison explains his operating model for transformation: define the outcome, anchor a strategy to that outcome, then build a plan that the business can own. They also explore career leverage, mentorship, fear as a signal, and why great CIO work is less about tools and more about aligning people, incentives, and accountability.

Key Discussion Points

Harrison shares the grocery store story that stuck with him: he thought he was trusted with the keys, then learned later it was an escape during a bomb threat, which taught him accountability the hard way.
Daniel and Harrison discuss why many companies promote or place people without matching strengths, and why the better approach is doing change with people, not to people.
Harrison explains the transformation chain: outcome first, then strategy, then plan, and why starting with a plan creates chaos.
They unpack differentiation in the AI era, where tools are everywhere, and the edge is understanding value, willingness to pay, and the unique properties of your tools.
Harrison calls out silos as a major failure point, where people show up as their function instead of as business owners solving a shared problem.
He shares his worst CIO moments: being asked to execute a doomed plan, or being the new leader who tells the uncomfortable truth and becomes the most hated person for a month.
Harrison describes the loneliness of leadership and how he leaned on reciprocal mentors and peers as a sounding board.
He argues EQ will matter more, but AI can increase effective IQ by offloading minutiae into a knowledge base so leaders can operate at a higher level.
Harrison closes with his butterfly effect story: a Kroger manager handing him an application changed everything, and his father’s rule became his compass: say yes unless you have a good reason to say no, and fear is not a reason.

Takeaways

The best leaders are transparent and candid, and they treat people as capable adults who can handle the truth.
If your plan is not anchored in strategy and your strategy is not anchored in outcome, your transformation is already failing.
Silos destroy momentum, and alignment happens when teams solve one business problem together instead of defending their department badge.
Fear is often a signal that an opportunity is real, and saying yes can create the career path you never could have planned.
In the AI era, differentiation comes from value creation and tool mastery, not from having access to the same software everyone else has.

Closing Thoughts

This episode is a masterclass in practical leadership, the kind built in stores, boardrooms, and crisis moments, not in slogans. Harrison Lewis shows that transformation is not a tech upgrade, it is a human alignment problem anchored in outcome, strategy, and accountability. If you are leading change right now, this conversation will give you a cleaner playbook and a better mindset for the hard days.

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