The Debugged Agenda | John Basso - What Actually Breaks Engineering Organizations - Part 1

In this first episode of Debugged Agenda, Jason Short sits down with John Basso for an unfiltered conversation about what actually breaks engineering organizations. Not the version that gets shared at conferences. The real one.

They get into the moments where leadership loses trust in the tech team, where communication breaks down before anyone admits it, and where the decisions that seem reasonable in the moment become the ones you are still cleaning up two years later.

If you lead engineers, work alongside engineers, or hire them — this one is for you.

What is The Debugged Agenda ?

We demystify what happens in the boardroom from a technology and C-Suite perspective.

Jason: 00:00

Don't you think those executive decisions that are happening in the boardroom will have, growth or separation between those companies that are embracing this technology versus those companies that are really cautious about, leveraging that?

John: 00:16

Definitely. Definitely. And I think it's gonna have dramatic consequences. Dramatic consequences.

Jason: 00:23

Such as what?

John: 00:25

Being in business or not being in business.

Jason: 00:27

Oh. Right. Yeah. Those are dramatic. That's right.

Jason: 00:31

Welcome to The Debugged Agenda, the show that highlights the leaders shaping the future of technology. I'm your host, Jason Short, and I sit down with today's top CTOs, founders, product leaders, and innovators to explore how they build teams, make decisions, and guide their organizations forward. These are thoughtful, candid conversations designed to inspire, not expose, and give you a rare look into how real decisions are made in the boardroom and beyond. Today, I'm joined by John Basso, who has built technology organizations from the ground up and then done it again and again. Additionally, John serves as a CTO for multiple startups, leading engineering teams through early product development, rapid growth, technical debt cleanup, and the inevitable, quote, we needed to scale yesterday, moments that every founder hits.

Jason: 01:29

John, you've done some amazing things. You're an entrepreneur, a consultant, a black belt, a snowboarder at my heart, a CTO, and published author. You are currently the CEO of Amazing Future. John, it's great to have you.

John: 01:44

Thank you for having me.

Jason: 01:45

So let's talk about what you're working on now. Give me a little bit insight on what you're kicking around.

John: 01:52

Well, so like everybody else at this moment, almost everything I have I'm working on has to do with the impact of artificial intelligence. And so all my clients are being impacted in different ways, but they're all being impacted. And it's a little bit about the AI, but it's also about what's the company's relationship to the AI. Like how are they going to adapt in this new world, which is exceptionally challenging because the uncertainty level is so high right now that people just really don't know how to react and don't know what to do. Right?

John: 02:29

So this is causing every conversation to be pretty long and convoluted as people trying to anticipate what's coming.

Jason: 02:39

Interesting. So what is frustrating about that?

John: 02:44

Well, I I in some ways, you know, my my, you know, I have a lot of biases because I've lived through a lot of these technical innovation cycles, right? Whether it be, computers with screens, faster computers, 16 bit, 32 bit, 64 bit, mobile cloud. There's just a series of these different events that have occurred over the decades. And in general, it usually takes ten years for these new concepts to be fully integrated into the ecosystem. There's early adopters of everything.

John: 03:21

I mean, we were I was working on mobile two years before the iPhone and Android. I mean, we were building mobile devices before there was even the popular platforms, but it takes ten years. But with AI, what I feel is that the genie got out of the bottle a little quick before enough of the foundational work was put in. And that just might be my bias and how I'm being impacted by it. But it seems there's a lot going on, but there's just so much confusion and there's so much change that because of that, it's very hard to do planning.

John: 03:58

And a lot of people, a lot of companies like the planning of three year cycles, and now they can't even plan in a one year cycle because things are changing so fast, and what's becoming possible is evolving so quickly.

Jason: 04:09

Yeah. So I just did a tech series on how AI is bringing back test driven development and how testing like, testing those results has to be now it's not it's no longer the, oh, it's good to write unit tests. Right? Now if you're doing pair programming with AI engines, you have to test those results because the you have to validate somehow that what you're getting back from those engines is what you're looking for to begin with, right? What you were looking for to begin And so

John: 04:42

I have the advantage. I work with several different companies and several different teams. And the teams are evolving slightly differently, even though they're all adopting AI. And those changes are fascinating to watch because they're truly transformational. Okay.

John: 05:02

And so I can give some examples of that. So for example, right now, people think of a team, they think of humans working in a group, right? And if you look all the way back to like the fifties when Drucker was starting to analyze companies and starting to get that business process, and then you look forward to lean and all these kinds of business organizational trends. It's always focused on the team of a group of humans rightfully so. But now what I'm seeing is a transformation is that teams are becoming hybrids.

John: 05:34

And some of the teams are human and some of the teams are AI agents. And we're in the very early days of this. So it's very hard to see how this will sort out. But normally you would say like a programmer writes the code, and then a tester tests the code, right? It's from the human first perspective.

John: 05:54

But what I'm seeing happen on my teams today is they're slowly, that's disintegrating around them. And so now the teams are composed of the humans and the agents, and sometimes the agents write the code and sometimes agents QA the code and sometimes the humans write the code. So for example, I have a team that when they're using their agile board to, plan out their work, they'll tag the tickets they want the AI to write. And then in the morning when they come into work and everybody's doing a standup, they'll go through and look at what the AI did and determine to accept it or reject it going back to your testing. And then they have, and that cycle isn't just a little agent rank code.

John: 06:35

It's an agent writes a code, and then another agent writes a code, then they compare the code and then another agent QA's the code. And then the code has gone through another set of tests. And then ultimately it's being reviewed by a human in this case, right? And so this is a pretty radical shift and people are trying to figure out how to adjust to these shifts. And it's just not a human kicking off an agent.

John: 07:03

Now agents can summon other agents to help them do work. They're collaborating like a team. And this is a pretty new evolution of the maturity cycle within AI, but this is definitely here today.

Jason: 07:17

That's amazing, that companies have taken that's that step. I mean, that's that really feels like not bleeding edge, but that really feels like on the forefront of being able to leverage these AI engines to take the scrum process through all its phases. And you've got engineers looking at that and just validating the results. Right?

John: 07:43

Right.

Jason: 07:43

Let's take that leap. Right? Let's take the leap from, okay. We're implementing AI into our company. How do we how do we as executives, start to plan for this?

Jason: 07:55

How do we as executives start moving this forward? Right? I think some companies are really kinda dipping their toes into AI in the engineering space. Right? And they're like, can I have AI write my unit tests?

Jason: 08:08

Okay. Great. And then you on your given your example, they're like, hey. Can I get AI in every facet of every phase of the scrum methodology and have engineers look at that and validate those results and and maybe discern where where we put engine where we put an AI engine onto and where we don't? And you've got everything in the middle.

Jason: 08:32

Right? You've got

John: 08:34

a company Including nonadoption. Including nonadoption.

Jason: 08:37

Yes. Right. That's right. That's right. Yeah.

Jason: 08:39

But those decisions, like the one company that I'm thinking of right now, their CEO basically said two years ago, if not three years ago, hey. Everyone in this company should be using AI on a daily basis. I mean, that was his stake in the ground. And from that point forward, they they launched into full, AI factoring of their procedures and their processes and their daily work and everything like that. To to some companies, that decision has to be made at the very top.

Jason: 09:13

Right? At that c e Correct. At the CEO level.

John: 09:16

Yeah. And and, you know, like everything else, there'll be rogue agents that will just start doing things. Let's think about where companies are and what they're doing. And there's these patterns that always repeat themselves. I see over and over that you can almost like plug and play whatever words you want or whatever current modern theories are.

John: 09:35

So when people adopted computers, they went through great pain, enormous pain of literally copying the exact process that was done on paper and a clipboard and putting it on the computer. I remember having a client way back in the beginning of the web where they were making them more JAP application form exactly the way it was. So people wouldn't have to, you know, learn something new. And and that form was like the most horrifically designed form ever if anybody's ever applied for a mortgage. Right?

John: 10:06

And they spent all this brain damage to put the paper in the computer exactly the way it was. Okay. So people tend to do this with technology. They tend to take their world today and they tend to kind of mimic it with the new technology. Okay?

John: 10:24

So what you're going to see in the beginning is companies are going to take their existing processes and their existing people and their existing tools and automate them. Without changing

Jason: 10:36

any of the processes

John: 10:37

Without changing a lot of things. And that's gonna be great in a lot of ways because we're gonna get rid of all what I call the toil. Okay? I have clients that it literally takes four hundred hours to do some compliant reporting, blah, blah, blah. And they're gonna get that down to forty.

John: 10:53

Well, the person who had to spend that four hundred hours is very excited to get that report down to 40. And you're still human in the loop and still review just automation. Forget the app, just automation. Sure. Okay?

John: 11:04

And that's awesome. But that's really the same thing just automated. Okay? That's right. Okay?

John: 11:09

That's right. Now, that's where we tend to start. Now, some innovative person is gonna say to themselves, why am I even writing that report? Why am I even assembling that report? Why can't that report just write itself?

John: 11:25

Or why can't whatever compliance thing that needs to be done, just be take care of itself? Right? And so instead of copying what they're doing today, there'll be some true innovation with the new capabilities and what can be done. Like right now we're talking about automating jobs. We're not talking about new roles and responsibilities in the company, but that will come as the tech changes and transforms.

John: 11:50

As we go through these different levels of maturity and adoption, people will get past just moving the paper to the computer. They'll get past just redoing everything they're doing now just faster, cheaper, better, more ease more easily, And they'll transform into new ways of doing things. Okay?

Jason: 12:09

Yeah. Yeah. Because it's hard to think about it until it shows up at your doorstep. Right? It's

John: 12:15

Right.

Jason: 12:16

It's like

John: 12:16

You know, you know, initially people had bicycles and carts and things like that and horses. But they couldn't imagine car. You can make Right. Yeah. You can make horses faster, maybe put horses punched together, you can pull stuff, maybe put an ox in there, whatever.

John: 12:29

But you still have the same primary function of, yeah, you could have a really healthy horse, you could have a couple horses, but that's radically different than inventing a car.

Jason: 12:37

Right. That's right.

John: 12:38

Or a plane.

Jason: 12:39

That's right.

John: 12:39

Or a rocket ship. Okay. Both or something. Yeah. What companies tend to do, and this includes the organization, is they tend to kind of hold on to what they have until they can reimagine the new structure.

John: 12:54

And so I think teams are going to become more important because in many ways the teams might shrink or the throughput might double with the same team, which is really saying the same thing. Right? Which means the roles are gonna switch, which is very hard for people to contemplate right now, which is adding to the uncertainty.

Jason: 13:15

So the one of the examples that you gave was back in early in your career when computers came out, you had email as something new. Oh, yeah. I remember. Yeah. I remember Lotus Notes.

Jason: 13:28

Tell me that story about how the executives would just hire people to

John: 13:32

Yeah. Yeah. Yeah. So I worked at I worked at, well, it's now called Accenture, you know. Right.

John: 13:39

It was Arthur Andersen back in the day. And they were early adopter of technology because they were at that point, I think the world's largest consulting company.

Jason: 13:47

Yeah.

John: 13:47

And we had whole skyscrapers full of consultants because there was nobody that could do that kind of work, technical work. And I remember we had the world's largest installation of Lotus Notes. And for the people who've never heard of that, that's the precursor to email. So, That's right. But there were partners, that's how it was structured in that company.

John: 14:08

Those are the people in charge. Those would be like the executives. And they literally wouldn't use the email system. They would have somebody type in their emails for them and print them out and they would read them. And then somebody else, they would dictate a response and somebody would put the email in.

John: 14:27

And so it's like, you know, adoption is not always come smoothly and willingly, right? It takes some time for adoption to occur. So, you know, that, those sort of things, we used have little baskets on our desks that people put the little memos in. That's how information would distribute. Everybody had a basket and we had a whole floor in a skyscraper dedicated to the printing room.

John: 14:51

They had high speed printing presses, and somebody print out a memo and you stick it in the baskets. And then Lotus Notes came, and then you stop the basket you did on the on the you know, for people lucky to have PC, you should it on your PC. And then after that email came.

Jason: 15:04

I think it's fascinating, in the sense of, like, time wise, and the evolution of computers and the things that it can do and that kinda just rips through years of, decades at lightning speed. You know, if we talk to my son who's 25, the concept of, printing notes and putting it in somebody's basket to tell them about, you know, a meeting that they might have is just, like, bonkers. Right?

John: 15:31

But but the interesting thing is if you go way back into the archives of when all this stuff was invented, what you'll find is there were literally demos, ten, twenty, thirty years of like MVP versions of really rough products that all became true decades later. But yeah, but so there's all this uncertainty in the tech, which is causing uncertainty in the business models, which is causing a lot of work in the boardrooms.

Jason: 16:04

And the the difference between a seasoned veteran software engineer that can look at the results given to him by the AI engine about code, and he can evaluate those and read those and look at that and say, merge this into the main branch and start QA the process. That differentiator between the junior developer that's looking at the code and was like, kinda looks okay to me, and I think that's the right unit test. Right? That that gap is gonna be much, much larger. Right?

Jason: 16:36

I I see that as like the same thing with these corporations, these executives that are willing to put themselves out there and try AI versus those corporations that are just kinda like dragging behind them saying, hey. Listen. We're gonna we're gonna ease into this AI thing. We're gonna dip our toe in, and maybe this year we might, you know, bring on or allow people to start using engines. Right?

Jason: 17:03

Like, that's totally different. Don't you think those executive decisions that are happening in the boardroom will also have the same, growth or separation between the senior engineer and the junior engineers? Those companies that are embracing this technology versus those companies that are really cautious about, leveraging that?

John: 17:23

Definitely. Definitely. And I think it's gonna have dramatic consequences. Dramatic consequences. Such as what?

John: 17:33

Being in business or not being in business. Yeah.

Jason: 17:36

Those are dramatic. Yeah.

John: 17:38

Mean, there's always there's always industries that are laggards that like lag way behind. There's always consumers that lag behind. So it's not like markets are going to vaporize overnight, but I see it already. I see kind of executives falling in a couple of different camps. So like one camp is, let's do business as usual and let's run this through review process because we're not quite sure yet.

John: 18:02

And this, that and the other, and they're going this very slow methodical way, which has served them very, very well up to this point. Okay. I don't a 100% know the impact. I sense, I intuit from my experience that this is gonna be a big deal. So a little bit how quick iterations developed in computer software releasing over the last couple of decades to get software out faster.

John: 18:29

Some executive teams are adopting that in their company like, Hey, listen, I'm not exactly sure how this all going to work out, but I believe the impact's going to be big. And I believe it's important for us to know, and the only way we're gonna know is to do. I don't know who said this quote, but I heard this quote once it always stuck with me is you can't learn how to swim from reading a book. Right. Okay.

John: 18:50

You gotta jump in the pool at some point.

Jason: 18:52

Okay. Right.

John: 18:53

I'm pretty lucky. I get to work with investors and private equity venture capitalists, that kind of stuff. Because I'm either helping the company prepare for a sale, or I'm helping the buyers evaluate the company on should they purchase a company. So about once every six months or so, I go through a deep dive of a whole organization including tech, but the organization at large and evaluate the company. Some kind of next generation companies that I call AI first companies.

John: 19:22

Okay. And an AI first company does not go through that very long blown out process. They very quickly figure out what their decision to be and they figure out what experiment they're going do, then they do it and they learn from it. And so you're not going to learn how to swim from reading the book. You gotta jump in the pool and maybe hold onto the edge so you don't drown, but you got to get in the game and learn it because this is a very esoteric conversation.

John: 19:52

And so for me, the companies I'm working with, I think the ones that are going to do the best are the ones that are adopting. They're being cautious, but they're adopting and they're doing different things to learn so they can figure out what they really need to do. Because it's gonna take a long time for the industries at large to get educated on what's possible.

Jason: 20:16

That's the thing. Right? Yes. That's the thing.

John: 20:19

I always joke. There's a scene in the Lord of the Rings, I forgot which movie, where the whole earth is burning down and they go to the trees and the trees are having this like long pontification about what language they're going to talk in to make the decision about what they're going to do. Some companies are going to be in that camp. But when I talk when I talk about this these changes, every conversation takes about an hour to start the conversation because there's no common language, there's no common understanding, there's not a lot of experts, people don't know what's possible, then they're trying to map it to old models and it's just different. And so it's very difficult for companies to navigate this because they can't even communicate about it.

Jason: 21:06

You say that the level of commitment to this from different people in the boardroom also adds to that problem?

John: 21:16

Yes. Yeah. Well, and and things are changing. Okay. So let me yeah.

John: 21:21

Let me just, tell you about something I noticed that's, changing recently. So everything's moved to the cloud. Okay? Mhmm. And that transformation has been going on for a while, started quite Right.

John: 21:34

Some time Okay. And so right now, if you were a normal company and you're saying, okay, let's go build out something. Nobody would raise their hands and Hey, I got an idea. Let's put that in the office next door. They'd be like, What are you talking about?

John: 21:50

Like that's those problems, we don't have to worry about power, cooling, storage, security. That's all been taken care of by this thing called the cloud. Okay, we're all familiar with that. Okay? Right.

John: 21:58

So here I am, I walk into the room and I say, Hey, listen, I have this really amazing architect. He needs some horsepower. Okay, I know you have him on this $800 laptop, which is great because most everything he's done is really been done in the cloud. Here's what I need from you today. I got a whole team of these people.

John: 22:15

Each one of those people need a $4,000 Nvidia Blackwell supercomputer that's sitting right next to them. They make these little things, right? If you can buy them, which you can't, but if you could, the little boxes. And they all need a thousand dollars of credits for tokens to do their job. They're gonna look at me like, wait a minute, you're raising my costs from $800 every four years for a piece of hardware.

John: 22:40

And now you want me to spend $5,000 on something I'm probably gonna have to throw away in a year or two? And I'm gonna be like, yes. And they're gonna be like, no. I'm gonna be like, yes. And they're gonna be like, no.

John: 22:55

So you know, it's just like you're gonna have this weird head bunny. And because we've moved away from people having superpower for computers because all that power was remotely hosted. Okay. So you're gonna have that conversation times a thousand as companies remap to this new world and what's gonna be required.

Jason: 23:11

Yeah. Yeah. Exactly. Yeah. Yeah.

Jason: 23:15

So what's one question every VP of engineering or CTO should be asking their CEO or their board? Like, what's one question that or one request that they should be making today?

John: 23:27

Yeah. I think it's hard to build the full plan out until you understand what's possible and what's needed within your organization. And so the real question is how do we start and how is each person, each team, each division going to begin this transformation? Not how they're going to end it, but how is each person going to start? Because it can be very different for different people.

Jason: 23:53

Don't you think, though, at some level that they need to be able to explain the benefits of of starting? Right? They have to kinda Yeah. Be able to paint a picture to the CFO, the CEO. Hey.

Jason: 24:04

Listen. With all this additional expense and this additional hardware, this is where we're headed. So we're used to being able to push out five new features a year. However, if we make this investment and we make this change in our process and we take the risk into AI, and as an executive team, we get behind this, instead of five new features a year, we're gonna be able to push out 25 new features a year.

John: 24:29

Correct. The real thing that's happening is there's a high amount of uncertainty and a high amount of change. And some companies are more prepared for that and some companies aren't. So if you have high performing teams, right? That have a high level of trust, which is, you know, one of the key indicators of the success of the team, not just from educational studies, but large companies like Google have done very complex studies about what makes a team high performing.

Jason: 25:04

I remember talking about this. Yeah. Trust is a big deal.

John: 25:07

Yeah. Trust is a really big deal. And so when you look at trust models, there's a lot of different models. Agile has the, you know, has a model. There's other models that have been in existence, but if you look at, you know, what, you know, what they like the course thing.

John: 25:29

If you look at the Agile one, it's form, storm, norm and perform. Those are like the stages you go through. Okay. And so that's when the teams, to do that, you could go through this transformation really fast. If you have what they call psychological safety or trust, right?

John: 25:43

Just kind of different angles of the same kind of concept. And so if teams are high performance and they have a high level of trust, they're much better positioned for earth shattering transformational events. Okay. Because they're operating at a higher level. And by the way, you can talk about people being like that.

John: 26:06

You can talk about teams, you can talk about divisions, whole companies, cause some hope, sometimes whole companies are like this, right? And so what's happening is we're getting a lot of change in a very short period of time. And so the companies that are better run, that have a higher level of trust within their teams are better positioned to go through the transformation. What I challenge people to think about is, when I think about a team, I have a much different view of a team. I think of a team as all the people and the resources required to deliver on whatever the shared goal is.

John: 26:44

Right. Okay. And so a lot of people think about teams as these are my five staff people that just team. Well, if you have a critical dependency on a vendor and you can't deliver unless that vendor delivers, well, you should probably expand your notion of a team to include that vendor and work them into your processes and get them in a high trust relationship, not just a transactional relationship. Because when push causes shove and a lot of changes need to be made, you're going to need your vendor to trust you and you're going to have to trust your vendor.

John: 27:16

And that takes time and effort to build that level of trust. Because trust tends to come in like four levels at the very lowest levels of transactional as you work your way up, you just like inherently trust a person.

Jason: 27:31

Okay? Right.

John: 27:32

If you have things like trust, and if you have alignment that better positions you for the transformations you have to go through. And going back to your comment, this is going to separate companies because the companies that are better run and are run with that alignment and that trust and that organizational skill and execution, they're going be able to transform better. They're gonna have less painful transformations.

Jason: 27:55

Sure. Sure. Yeah. So is that And

John: 27:57

so a lot of my time is spent on that with executives.

Jason: 28:00

Yeah. So I was just gonna ask, do you think that is the catalyst to being able to move forward? And is that only at the executive level? So for before like, I'm a change advocate. Right?

Jason: 28:11

So I come into organization. I look at the structure. I look at the executive. I look at the team from a development perspective. And I go, okay.

Jason: 28:20

How are we doing based on real results? And what can we change to get better results? Right? But before I do that, I I have to sit down with every individual. And this takes time.

Jason: 28:33

Right? And get to know them and talk to them and understand their point of view even though it might not be the other people's point of view. Right? Correct. So creating this trust is like a catalyst to being able to then implement change or new technology or a new vision or fill in the blank.

Jason: 28:54

Right?

John: 28:55

Yeah. And studies have been done on this. And, you know, what you'll find is in situations where people don't have time, because time is one of the critical elements of the building trust. What happens is people have to defer to something and in essence what they defer to is rank. Okay.

John: 29:11

So if you're in a situation where there's an auto accident or something's going on, right? And and somebody with a badge shows up from the FBI, okay? You're gonna defer to the rank of the situation or maybe somebody an EMT crew shows up and they're the experts. So you're deferring to like the skilled person or the highest ranked person, you just defer. And by the way, this doesn't happen in weird situations.

John: 29:35

Most cases when you go get operated on or have surgery, the people in there don't know each other. And how they make that work is they defer to the surgeon because he's the highest ranking person in the room. Because it's in a lot of cases, the surgeon is hopping in a room with other people who perform other parts of the procedure Right. Who they've never met before possibly, right? I know it sounds crazy, but that's how medical So space if you don't have time, you have to defer to something else like skill or rank, Right.

John: 30:07

But what you really want is time because if you're gonna make any significant change, you're gonna ask people to make a little bit of leap of faith, and they're not gonna know, they're not gonna really be engaged in that or wanna do that unless they trust you. The only way to get the trust is to build the trust. You have to earn the trust. Right. Yeah.

John: 30:26

So I do the same thing you do when I'm in with teams. I sit in with their stand ups. I sit in in stand ups. I don't talk a lot, but I just listen. I become like part of

Jason: 30:37

this The team. Part of it. Yeah.

John: 30:38

And then I start making recommendations. I start working. I start working with the team to get them open to change and then get them ready for the change. But what I'll tell you is when I walk into high When I walk into teams that are higher performing, some teams are really low performing. If I work at teams that are high performing, they are much more open than a change because I know each person's got each other's back.

John: 30:58

Right. If I work walk into a low performing team with a low level of trust, it could take a very long time to build that trust in that team to prepare them for the change.

Jason: 31:07

Yeah. Yeah. It's there.

John: 31:09

And maybe more time than they have.

Jason: 31:11

When you walk into a boardroom, right, who really has the authority versus who's just loud? Right? So, like, you talk about rank and you walk into a boardroom, you would think, oh, well, the CEO is the surgeon in this, right, analogy. Right. Right?

Jason: 31:27

He has rank. However, I've walked into tons of boardrooms where it's a even playing field and sometimes it's not always a CEO that has the rank.

John: 31:41

Correct. Yeah. So there's to understand that takes a little bit of experience, like what's there's the official org chart, and then there's how things get done in companies. Those are two different org charts. Okay.

John: 31:54

And so, but let me give some examples of how this can happen. Let's say you have a founder of a company and the company has grown so big that investors or the founder himself has brought in somebody to operate the company. Okay? And so there's a new CEO and maybe they've hired thousands of employees since that person started this thing in their garage. Okay.

John: 32:15

Maybe the founder is still involved. The CEO is in charge, but the founder is still involved. So is the CEO in charge or the founder in charge? Because what you'll see is the CEO might let the founder go, and then when it hits a topic that like is core to the founder's essence, it might be marketing, it might be finance, it might be product development, then it's going to be the founder's way. Because there's no amount of convincing that's going to move them because they're the founder and they know, right?

John: 32:40

And it's their company and is their idea. And so that's when you have the dual, okay? That's one example. Another example could be is there could be an individual in the room that holds a certain amount of leverage over the rest of the team. And the rest of the team is basically giving that person a lot of passes because of the leverage they hold.

John: 33:02

Okay? So an example of a way a person can hold leverages, maybe early on the company's career, that person made an investment that kept the company afloat, a personal investment. Maybe that person, they left would go to a competitor and empower and competitor and they just don't want to lose that person. The reasons don't always have to be good for that leverage to exist. They can actually be quite bad.

John: 33:28

So what you have is you have various levels of power structure in a room regardless of the org chart. And so you have to get a read on that, Right?

Jason: 33:37

Yeah. So for someone who's walking into a boardroom for the first time, what are the things that you look for to navigate that?

John: 33:45

Yeah. I look at everything. I don't wanna sound paranoid about it, but I look at where people are sitting, because people tend to sit certain places and certain things. I look at how engaged they are in the meeting. If they're participating or not participating, I try to understand how they think.

John: 34:06

And what I mean by that is some individuals can off the cuff, have a conversation. Other people have to go back and process a lot of the data. So a lot of people that are architects like the process I'm a processor.

Jason: 34:21

Yeah. You gotta get

John: 34:22

some time to process.

Jason: 34:24

If you

John: 34:24

do this like rapid fire thing, that's not very good for them. But Right. And so some people are processing. So it's it's it it is unbelievable to me how hard it is to create a good cadence in an executive meeting. Because you'll be going to a certain flow, and you'll be on topic three, and literally halfway into topic three, somebody will rewind you to topic one, and consider and continue this conversation about topic one that you thought you already decided.

Jason: 34:56

Right.

John: 34:56

And that's because they were still processing. But they didn't have any way to indicate that they were processing and people didn't pick up on it. And so they just kept moving because, know, as executives, you gotta move through a lot of topics. Right? And so so that happens all the time to me.

Jason: 35:13

So how do you navigate? Like, how do you what do you do in that instance?

John: 35:17

Well, it's very difficult to go to the next topic without wrapping up the previous topic because ultimately, people aren't listening and participating. There's thing very low.

Jason: 35:29

Yeah. Right. That's right.

John: 35:30

Right. So you have to finish the topic.

Jason: 35:32

So you have to put put a pin in it, go back to topic two or whatever. Yeah. Wrap that one up and then go back to topic four.

John: 35:40

Yeah. That that's one permutational problem. The other permutational problem I see all the time is people come in a meeting with an agenda. You know, some companies run better than others. They can stick their time.

John: 35:51

They can stick their agendas. Other companies are kind of all over the place depending where they are and their kind of maturity cycle. If they have an agenda, what sometimes you'll notice is you'll get through one item in the agenda and then the meeting will go off topic. Yep. Because there's some passionate burning conversation that somebody's just got to get off their chest and they can't go to the next thing.

John: 36:13

And I find this fascinating because sometimes they might even be right, it might be an important thing. It's just this isn't the right place to talk about it, or it's not the right level of things. Like if you're in a meeting and you're talking about Some in meetings sometimes and people are talking like $100,000,000 cloud spends, right? Okay, that's not the time to argue about should the person down the hallway get a new mouse or not. A $100,000,000 cloud spend mouse don't belong in the same conversation ever, Ever.

John: 36:44

And so you'll have these like hot button topics that people are kind of like viscerally worked up on. You can see them. So you have to figure out a way to get those on the table and either get them parked somewhere put in a parking lot, or let them go through a little bit of the vent and get it out of them, right? So you can return to business because otherwise that person is not going to be engaged. It's very hard to get full engagement in these meetings given the level of distractions that people face today.

Jason: 37:17

Thank you for joining us with John Basseau on The Debugged Agenda part one. Please join us for Part two as John and I talk about what happens behind the boardroom doors.