Reaction to Inaction with Jack Jackson

Scott Kinka: 

Hi, and welcome to another episode of The Bridgecast. This is gonna be a fun episode. My guest is Jack Jackson. He’s right here on the screen with the seasoned tech exec, currently serving as the SVP of Sales & Marketing at Aratum, where he’s been for a little under a year. Think more importantly, he’s been in tech, and I’ll let him tell his story for 20-plus years. The reason why we’re getting together is Jack reached out to me. As a fan of the pod, I hope you don’t mind me saying that Jack is about to release a book, which we’ll talk a little bit about, but I feel the story, the title, and the idea are just super applicable to our listeners who are largely technology executives, which we’ll get into. So, with all that said, Jack, welcome to the show.

Jack Jackson:

Thank you, Scott, I appreciate it. I am definitely a fan of the show. I love the value add of the show, and I love what you’re doing for the tech executive community. So, thanks for having me.

Scott Kinka: 

Of course, it’s a little out of the ordinary for the kind of episodes that we do, but when you hit me, and you were like, hey, I wanna talk about this framework for business, given what I’ve heard on your show, I was like, okay, well, this could be interesting. Before we get into the book, though, Jack, here is a little bit of background. We usually like to start with a little bit of background on who we’re talking to right now. Just give us a little bit of information about you.

Jack Jackson:

Yes, Scott, I appreciate it. You know, I’ve been a tech executive for probably 20-plus years for multiple companies through successful acquisitions and hyper-scale. I’ve worked with the biggest kind of Fortune 100 companies in the world. I’ve worked with both public and private companies and spent my whole career really trying to bring some strong value to customers. And so that’s really kind of me. My story is about building businesses for companies.

Scott Kinka: 

And where are you located?

Jack Jackson 

I mean, I’m located in the Bay Area. Silicon Valley kid, right? Born and raised in Silicon Valley. I’ve worked for a bunch of Silicon Valley companies and then all the usual suspects out there, right? Kodak, HP, and all the usual companies are out there. 

Scott Kinka:

Got it. Family? What do you like to do on the weekends? Just give us a little bit about you personally.

Jack Jackson:

Yeah, yeah, man, a happily married husband of four. And I’m a big believer in the outdoors. My wife is an integrated nutrition coach. She just did her first podcast yesterday, talking about offering advice to professionals on making smart, healthy decisions on food and nutrition on the road and how to do that. I’ve got four beautiful kids, man. We’re all outdoors folks. We’re an entire family that trains Jiu Jitsu. I’m happy. Everybody, from my oldest to my youngest, who’s 11, trains jiu-jitsu. So, you’ve got a house full of folks trying to tap each other out, which is kind of funny, man, even my wife. And so we’re a run-bucket group, but yeah, man, we’re big outdoors folks, big fitness folks.

Scott Kinka: 

I love it. Sounds like, by the way, you and your wife could work together on the companion book for this first one. Maybe that’s the next one. So just give me credit in the forward on that book for the idea when that actually happens.

Jack Jackson: 

Yes. Absolutely done. I’ve actually offered it up to her. I said it’d be a great idea, a great collaboration.

Scott Kinka:

Love it. So tell me, what would you consider to be your business and executive?

Jack Jackson: 

Yeah, that’s a great question. You know, I think leadership. When you go to my LinkedIn and look at my network of folks who reach out to me and who I collaborate with, I think it’s leadership. I think leadership is about managing people. A lot of people think that leadership is about managing people. And it’s really about inspiring people and getting people in a position to be successful. I think that would really be when I look at my career, the folks, and the feedback that I get from people in my organization, counterparts, and partners. They always say, Jack, your leadership is exceptional. And I really try to find the best and bring out the best in people. Having a strong moral compass, having values, understanding really what their strong skill set is, their superpower is, and really trying to bring that out of them and give them that empowerment, that purpose, that value, and that trust to go do those things. I’ve had so many relationships in my organization where folks have come to me, both individual contributors and leaders in my org and say, Jack, I want to do something different. I want to move to finance. I want to move to product. I want to move to marketing, whatever that is. Walking through those harder conversations and saying, like, let’s understand that you’re not alone, that you do have a passion, that you have a skill set, that you could really do something wonderful with. Then, three, six months, and a year later, they’re just like the happiest person in the world. They’re like the best in the world. So, I like to pride myself on leadership and really try to help.

Scott Kinka: 

So that’s, I mean, maybe that’s the segue into the book, right? You’ve been writing it, I think you said, for 20 years. I guess every piece of writing is generally a collection of experiences, but you’ve chosen to title your book Reaction to Inaction. I think the subhead is how organizations, employees, and customers lose when people fail to act. Tell me a little bit just about the book itself. What were you trying to solve, and what’s the main message?

Jack Jackson:

Thank you. Yeah, Scott, it’s interesting. Now, I think it took 20 years because I wanted to get that one question right. I think it’s because I’ve spent 20 years building something of a reputation and dedicated my life to really building businesses and organizations and helping people. And the reality is that’s the one question I wanted to get right. So I named this book about 18 or 19 years ago, and I talk about in the book and just saw the frustration on his face that he couldn’t help the customer, he couldn’t solve a problem on his own, had to go through these processes and the bureaucracies and all these things. And he really loved the company. He really wanted to be wiped by the customer. And so I named the book in the hallway. 

The Importance of Leadership

Scott Kinka:

Jack’s book is titled The Reaction to Inaction and How Organizations, Employees, and Customers Lose when People Fail to Act. You told me that you’d been working on this for 20 years in the pre-show. You said you named it quite a while ago. Like what were you, what happened, and what were you trying to solve that prompted you to write this?

Jack Jackson:

Yeah, I think it took so long to actually get the book out because I thought it was most important to get that answer right. About 18, 19 years ago, I was in the hallway. I had started just as a lonely sales engineer at a company, and I watched somebody who really loved the company. He really was proud to be part of the company. He loved the customers. He had invested a good portion of his young life a number of years at the company. And I saw him just frustrated trying to help one of our largest customers solve a problem. And when I went to him with the common sense solution, he’s like, I can’t do that. I’ve got to go here. I’ve got to do this. I’ve got to these questions. I’ve got to go all in, and we ended up losing that customer. We ended up taking a big hit. And I talk about that in this in the book. And I immediately in that hallway said this is the reaction to inaction. And that employee ended up leaving and then going off and having an amazing career. But it was definitely something that stuck with me. And so, over the last few years, I don’t know how many years I’d have had two notebooks. I’d sit in a board room. I’d sit in a meeting. I’d sit at my leadership conferences at those big retreats. I would listen to people talk, and I would keep notes on the business. But then, I would take notes that were applicable and that I thought would add value to people in different organizations. What gaps do I see? What frustrations do I see? Everywhere from processes and operational things to just helping people solve problems and their frustrations. And throughout my career, I can tell you, man, there’s been dozens and dozens, and I’m sure your listeners can relate to this. You, your audience, are gonna feel this when I say this. You know, how many great, wonderful, amazing, dedicated employees have left organizations because of that type of frustration? And so I said I think it’s time and our place with the advent of AI and the advent of new technologies, people are feeling that more. How do we build the organization of the future? How do we build the AI organization for the future? A living, breathing, dynamic organization where people feel empowered, people are high performers, and trusted, but they’re also all that red tape and bureaucracy are cut down to a minimum so they can be dynamic and innovative. And you read in the news every day about American businesses slowly becoming smaller, losing market share in the world. I think China has just sold out American cars, predictably, in the world for the first time ever. And I think Elon Musk made a comment about that. And so I said, it’s time to propose this framework that I think might be really, really valuable. And I’ve been applying it over the years of my career and seeing just amazing results.

Scott Kinka: 

So we’re going to get into the framework in a minute, but let me equate it to something that our listeners hear me say: you talk about that inaction, and both internally and on the show, I have said like, don’t be in the business of being in business. If you kind of get where I’m going, it is an applicable statement. Am I kind of hitting what you were, where you were chasing on this sort of inaction story?

Jack Jackson:

Yeah, a little bit. Now, my quote was always that everybody wants to sit around and talk about business, and nobody wants to do anything. And that’s another one. You know, I’ve sat in the room so many times with people just fighting over airspace to sound like they’re the smartest person in the room. Well, I’m saying to myself, where’s the customer today? What are we doing today to bring that customer experience to the best possible place it can be? So yeah, I agree, Scott. Absolutely. 

The Framework for Dynamic Organizations

Scott Kinka: 

Interesting. Let’s start with the framework. Obviously, the book’s coming out. So, to some extent, asking you to give us the trailer, right? But what can you tell us about this sort of structurally about the

Jack Jackson: 

Yeah, I think we’re doing it wrong. Organizations are doing it wrong. It’s antiquated. It’s old. It’s not the way of the future. And the framework addresses that. I’ve said this on a few different media platforms. It’s the consultant killer. It’s the coach book killer. The CEO walks into the boardroom and says, read this new great leadership book. We’re all going to do it, killer. We’re doing it wrong. You know, I’ve gone to these big expensive retreats, leadership retreats, where you spend $50,000. We all sit around, eat great food and talk about all these brilliant ideas. And then you go back to your organization, and you say, I learned how to communicate. And your team is like, what are you talking about? I don’t understand what you’re saying. I know we’re going to do things differently, right? As the big kickoff, we’re going to do something different this year. And it’s all the same stuff. You go back, you spend a hundred grand on a kickoff or half a million dollars on a kickoff in some cases, you go back, and everybody goes back to exactly what they’re doing. There are no innovative ideas, no new products, no pushing the envelope, no streamlining, and no more high performance. The quotas continue to go up, and the performance continues to go down. The product continues to be stale. What are you looking to like? What is the next idea? And you’re looking outwards instead of inwards. And so there’s all those kinds of things. It’s very, very tough. This book addresses everything from operations to human resources to culture. I mean, you guys are amazing, right? You guys are amazing experts in procurement. You guys are an amazing group of people. I mean, you care. You have insight and guidance. I know that about you. So when you look at what you do on a daily basis and how you like it, try to give the best experience you can to your clients; that’s what this book focuses on. This book is focused on internally and externally delivering the same type of stuff, Scott, you try to do in your team every day.

Scott Kinka:

You’ve mentioned a couple of times in that, on the framework itself, that it is based around the concept of putting the customer first and kind of taking the company structure, almost, I don’t want to call them fake, but you know what I mean, again, being in the business of being in business, right? These things we’ve built up, remove them out of the way for a moment and then just kind of focus on customer obsession if you will. And I have two questions on that, right? One, obviously, is that our listeners are IT leaders. And in some cases, certainly they, their customers are end customers because maybe they’re in a technology business. But I think, in many cases, they’re not right. The end customer for IT is the employee. Do you know how the framework applies to those kinds of scenarios?

Jack Jackson:

Yeah, no, that’s a great question. So I think we should start at a slightly higher level. We’re going to dive into it. There’s a whole chapter on that because I think it starts there, right? These CTOs, these CIOs, these directors of ITs, these are all friends of mine. We all grew up together in the industry. All I was just telling you right before this was that I was talking to a Fortune 100 CTO buddy of mine. He’s very familiar with what I’m building, and he sees the value in it. So how I’ve developed this book really has spheres of influence for leaders, and it works with everything from, like I said, HR to legal to finance the product to IT, right? One chapter is dedicated to IT. And so you’re really empowering; obviously, the CEO has the biggest sphere of influence, VPs, directors, individual contributors down, but they’re given this fence around them that allows them to think outside the box, allow them to make decisions, allow them to think about using another framework inside the book called the one minute, the one hour and the one-day decision making formula process. So risk versus reward, time frame input. So they basically take this formula and say, hey, this is the better cybersecurity posture. This is a better procurement process. This is a better way to serve those internal stakeholders. And just that alone, we can all talk about how something on the IT side isn’t working correctly. And that CTO is never going to know about it, never really going to understand the frustration until he does him all hands and he gets a bunch of questions, and they say, hey, this is frustrating. Why don’t we do this? Or this is a problem, or that’s a problem. This allows those folks inside of his organization to have that fence around them, to be able to make those decisions and to have that obsession with customer experience, which are those internal stakeholders. And I would argue that it reverberates throughout the culture of the company, right? Those daily frustrations go away. Is there a better, smarter way? To do it. And one thing I’m famous for in my organizations is whether I’m in my org or outside of my org in a company, I always ask, how do we do better? How do we do better? And I mean that, and it’s a conversation. It’s not just a quote. It’s not just something, but how do we do better? And so I find directors of IT, CTOs, CIOs, tech executives saying like, I want to do better, but my team is not doing better. Well, do they feel empowered? Do they feel trusted? Do they feel like they can make a mistake?

Jack Jackson:

And not be reprimanded for it. So even down to the one-on-ones, there are templates and frameworks for the one-on-ones of how to have a real valuable one-on-one, not just what did you do today? How many tickets did you answer? What threats were there on the cybersecurity side? What are we worried about regarding the budget? But it is really true: how do we do better this week? One day, one hour, and one-man decisions. How were those evaluated? What did they do? And what was their impact? How do we move the ball a little farther up the field?

Empowering Employees while Managing Compliance and Risk

Scott Kinka: 

There are so many schools of thought and pieces of content out there around employee empowerment. Think in particular in the era of COVID where people are at home, and there’s let’s look over the shoulder and all that kind of work. But I wonder, in IT, how do you assess the idea of empowering an employee to get something and solve a problem while still dealing with the compliance and risk challenges that come along with it? I mean, you mentioned AI earlier. Right. And I could think of, mentioned cybersecurity earlier, like every one of these scenarios is one where the mistakes can be really big. Right. So it’s kind of the imbalance of empowerment and compliance risk. Tell me how you account for that.

Jack Jackson:

Yeah, fantastic question. These are all things that are at the top of the mind of every executive. They’re definitely at the top of every executive’s mind. So, within the framework, we talk about AI, right? This is about building the organization of the future and always say the AI organization of the future. So, the wonderful thing about AI is that it’s going to push us to brand new limits and to think differently about how we conduct our business, right? How do we serve our customers and build products? How you deliver services in the most efficient, most brilliant possible way. Well, you need an organization to match that DNA. You need an organization to match that framework. And that’s what this book does. This book does the exact same thing. You know, the fingers and the limbs of the body of the organization are all doing everything a lot better, and they perform well in that way. So if you look at it like a director of IT, and you look at cybersecurity, they’re empowering their employees to think on their own, to make decisions, to protect the organization and protect that. Customer data, compliance, risk management, and they’re given a framework to make those decisions on the spot, to make those decisions intelligently on the spot and to make sure that they’re providing. That gives them higher performance. And by the way, Scott, there’s just so much data around this. There’s so much data behind this. In the book, interview data scientists, interview psychologists, behavioural psychologists, cultural experts, and motivators. You know, I mean, there are people out there that I just absolutely love. I look at Rich Roll, Jaco, and all these amazing folks like that who talk about empowerment and strength and building and discipline, all those kinds of things. Then, there are these other behavioural scientists and psychologists in the book. The CEO of Gold Star Gamers is going to be in the book. She’s somebody that I talked to. I walked her through the book and gave her some context about what this is about. She’s obviously a psychologist and very well known. And she said, Jack, how I look at this is when you look at a school of children, and they don’t have a fence around the schoolyard, they stay very close to the building, and they don’t leave it. But when you put a fence really outside the schoolyard, they’ll go all the way to that fence because of trust and empowerment. So I’m building fences. I’m building great fences so these employees can think outside the box and do right by their internal stakeholders and their external stakeholders. And what a great way to look at it. She quoted these studies and all these years of data around that. That’s kind of how you look at it. Yeah. So kind of like, I’m going to paraphrase, but you know, the idea of taking the fence down and just saying, Hey, everybody goes innovate is, and there were some, mean, particularly in the nineties, right? It was like, we’re going to go do innovation today. Right? So, like, let everybody do everything. You know, your point here, cause it, it seemed a little bit like, kind of in competition with your general story where you’re talking about building fences, because you’re asking, you’re talking about empowering people. The idea is kind of pushing the goalpost out, right? Like you’re basically expanding the area in which somebody can operate. There’s still an edge, but you’re just giving them enough ledge not to get to the edge but not necessarily fall.

Jack Jackson:

Yeah, absolutely. And if they do fall off, that there’s safety there, right? You know, in the book, I talk about a particular case that I wrote down. Had like probably eight pages on the situation that happened where employees said, I had to make this decision. It was important. I called my executive. They wanted to call product. They wanted to call legal. And I said what? We’re going to go ahead and commit to this, and we’re going to move in this direction. It ended up being in the wrong direction. But what ended up happening nine months later was that exact customer came back and bought 10X what they would have bought before. And this employee was not let go. This employee was not reprimanded, but I applauded him for making that step of saying, know what? At the end of the day, his comment in the book was that I was thinking about what was best for the customer and then the company. And I’m like, what can, again, there are pages on this situation in the book and in my notes. And it came back to, okay, we’re in a holding pattern. We might’ve lost this. This might’ve been really detrimental to the company.

Scott Kinka: 

Let me ask you some questions if you don’t mind. We’re to have a little bit of fun. And to the extent that it’s in the book, you can talk about that. Great. You know, get down to some tactical stuff on this. Give me some advice from your seat. You’re about to put a book together, and a major publisher behind it. Obviously, the content’s good, right? Give me some advice for IT leaders that maybe you wish you knew 20 years ago. Something simple that they can take from this podcast and apply today.

Jack Jackson:

Yeah, don’t manage by the numbers. The best IT executives and leaders that I work with have to manage your P &L. We do, we all do, I do. We have to manage the numbers. But sometimes, we get so focused on that. I think that there’s 40 % left, as I would say, in the tank. To quote David Goggins, there’s 40 % left in the tank of performance that you can get out. If you can just take your eyes off those numbers for a minute and ask yourself, how do we do better? How do I widen those fences in my organization? How do I think about the business in just a different way? And I think that one of the big parts of this is how we do it.

Lessons in Leadership After 20 Years

Scott Kinka:

Okay. Yeah. Interesting. All right. Here’s what this would be: a funny one. Give me the most recent leadership lesson that you learned that you probably feel like you should have already learned. Like, what’s it? What did you just recently learn that surprised you after 20 years of doing this? Give me something that you’re like, man, that should have been in the arsenal.

Jack Jackson: 

Man, there’s so many. There are so many. I feel like I’m learning every single day. A good leadership management lesson. Man, you could just ask my wife. I’m sure she’s got a million of them. She teaches me every day. But I would probably say paying closer attention to these small things in your organization. I would say the feeling and the emotional aptitude, I think, in an organization when folks are feeling burned out. Recently, an employee came to me, very emotional, and said, I’m just burned out. I don’t feel like I’m making progress. I thought the employee was doing fantastic. And they conveyed something to me that was really interesting. They said I’ve been dropping hints throughout this that I’m not getting what I needed and not feeling like I’m getting the support that I needed. And I’m implementing this framework. I work for Aritum. I’m kind of an SVP and slash in a CRO role, right? And I’m thinking, wow, we’re building this great culture. Everybody seems really happy. The board, everybody seems really good. We’re a high-performance team a great product, and we’re doing great. And this kind of seasoned employee was like, I just don’t feel like I’m what I need out, and that was a big lesson for me, so I should pay attention to the smaller clues, right? And so that would probably be the most recent one that I’m like, why did I not know that? I pride myself on that. Should have done better.

Scott Kinka: 

Got it. Yeah. Well, what question could you have asked them that would have picked that up in your mind?

Jack Jackson:

I learned this from an executive recently. This question that I thought was brilliant was from an executive that I worked with, an instructor, and a gentleman named Chris Ball. he asked a question to one of us in our QBR, and I thought it was brilliant. He said, okay, what didn’t I not ask you that I should have? And I thought, wow, that’s, I’m going to steal that. And, shamelessly, I’m stealing it now. What a great question. Yeah.

Scott Kinka:

All right. I’m going to steal it also. That could be a quotable. Like that. All right. Just a couple, two more quick ones and then we’ll let you go. You’ve been super generous with your time. What’s on your end table right now? Who, who are you reading? I mean, you’re you’re hoping we’re all going to read you as this book comes out, but what are you reading?

Jack Jackson:

Yeah, I’m reading the Dichotomy Leadership by Jocko Wilnick. I’ve got three books I’m reading. I’m reading Lessons of the Bullfrog, which is an amazing leadership book by McRaven. Then I picked up a fun book that I just opened and started called The Continental Reckoning by Elliot West about the great expansion into the West United States. And I’m sure there are some lessons in this book to learn about.

Scott Kinka:

It clearly doesn’t look like light reading. Holy cow. You bought the hardback. That’s gotta be a thousand pages. No, all good there. Last one. I’m, we’re to have some fun with this one. I’m trying to pick which one. All right. In a dystopian future, robots will take over from AI, all the suits, and all the people who claim the end of the world is right. Only one app works on your phone for your survivalism. Which one is it?

Jack Jackson:

DoorDash.

Scott Kinka:

I mean, Jack, you got to eat, right? Maybe that’s the best business advice you’ve ever given right there. You got to eat. Appreciate it. Jack, just quickly tell us one, how people can track you and be prepared for the book, which is not out yet, but it comes out, I believe, in the fourth quarter, but how do they follow you and make sure they’re ready to get this framework?

Jack Jackson:

Yeah, you gotta eat nutrition. Yeah, Scott, first off, thank you for the time. This has been fun. I’m honoured to be on it. I reached out to you and said, I got to get on here. You guys add such amazing value to your audience. And I’ve encouraged my network of folks to tune in and to get to know what you’re doing as well. So, first off, thank you. Really appreciate it. And I am a fan. Yeah, the website is called thereactiontoinactionbook.com. Check it out; you know, pre-order it. I’m doing something special. We’re gonna be doing book signings and all those kinds of things all over. We’ve got Mexico City, London, the Bay Area, New York, and all these places, but you know, order it now. Order it now. It’s gonna come with an autograph and a little bit of a special gift for it. Everybody’s telling me that it’s going to be an instant bestseller. Everybody’s going say it’s going to be something on the bookshelf for a while to come. It’s just different. It’s groundbreaking. It’s innovative. It’s a fun read, but it’s not a read for the CEO. It’s a read for everybody, everybody in the organization, and anybody who wants to do better and have a better impact on the organization. It’s a framework, not a self-help book. So go out there and pre-order it. I promise you, you won’t be disappointed. It’ll be something really special. And the gift that’s coming with it will be really special.

Scott Kinka: 

Cool. Jack, do you have a publisher on this yet? 

Jack Jackson:

Yeah, we have one. I don’t want to give it away just yet, but it’s a big one, and then we’re working with a couple of different great distribution companies as well.

Scott Kinka:

That’s awesome. All right. So check the website out. Let me see if I got that right. The Reaction to Inaction book

Jack Jackson:

Yeah, check it out and then follow me on LinkedIn. We’re gonna be dropping little pieces and tidbits throughout the next three or four months, and we’re talking about publishers, talking about dropping it sometime in January, February and what specific week to do it, and I’ll be doing a bunch of media appearances here over the next few months. So please follow me, pre-order the book and Scott, and thank you again for all your time. I really appreciate it.

Scott Kinka: 

Perfect. Of course, IT leaders need a ready-made framework for decision-making inside your organization, or I think, as you call them, my notes, a framework for the organization of the future. Check out Jack’s book and follow him on LinkedIn, hit the website, and maybe do a pre-order at least to follow. And Jack, I’m looking forward to having you back in the first quarter of next year after the book is already a hit.

Jack Jackson:

Absolutely, Scott. Thank you so much. Appreciate it.

Scott Kinka: 

You got it. Thanks.