064 The "Culture over Code" Philosophy The Technology Trap: with Jesse Wilkins

Everyone is talking about AI, automation and the latest technology.

But what if the real challenge isn't the technology at all?

What if the biggest barriers to success are culture, behaviours, information practices and the way people work?

In this episode of Information Matters with Jacqueline Stockwell, I sit down with industry expert Jesse Wilkins for a thought-provoking conversation about why organisations often focus on technology before fixing the foundations that technology relies upon.

Together, we explore:

✅ Why technology alone rarely solves organisational problems

✅ The difference between culture change and technology change

✅ Why information management is critical to successful AI adoption

✅ The risks of relying on technology to fix process and people issues

✅ How organisations can avoid the "technology trap"

✅ What information leaders need to think about before deploying AI

This conversation challenged some of my own thinking and reinforced something I've believed for many years:

Technology can accelerate change, but culture determines whether that change succeeds.

If you work in information management, records management, privacy, governance, Microsoft 365, digital transformation, AI or leadership, this episode is packed with practical insights and real-world experience that will help you look beyond the technology and focus on what truly drives sustainable success.

Because at the end of the day...

Information Matters.

About the Host

Jacqueline Stockwell is an international bestselling author, speaker, CEO of Leadership Through Data Ltd, and a passionate advocate for taking information management and privacy out of the back office and into everyday conversations. Through Information Matters, Jacqueline explores the people, leadership, governance, technology and information practices that help organisations thrive in a rapidly changing world.

Connect with Jacqueline

🌐 Leadership Through Data Ltd

📚 Author of Blooming Good Information Management

🎓 Creator of the EMPOWER Accelerator Programme

🎙️ Host of Information Matters with Jacqueline Stockwell

Transcript

SPEAKER_00 0:04

Hello and welcome to today's show. I'm so excited to have Jesse Wilkins on with me today. He is an information governance consultant, trainer, and keynote speaker. But what I love most, he knows that technology is rarely the problem. You need the right people, the right disciplines, and the right strategy. So welcome to today's show, Jesse.

SPEAKER_01 0:26

Excited to be here. I can't I just can't tell you. I've been pushing this to my people all day.

SPEAKER_00 0:31

So let's talk about the technology trap. So you often say that technology is neither the problem nor the answer. So uh putting it into some context, if a client comes to you convinced that they just need a better SaaS tool to fix their data mess, how do you gently break the news that a call is coming from inside the house?

SPEAKER_01 0:52

You know, it's funny, I I literally got off a call this morning at my time about an hour ago where that came up. They said, you know, we we've got this, their particular issue was with email management. Their people wouldn't manage it effectively. Their email inboxes are approaching 100 gigabytes each, and they wanted a tool. It's like, well, guys, that the issue here is not buying another fancy email archiving tool or or this tool or that tool. It's how you use your email. The fact that you're not getting rid of anything, the fact that you're signed up for every newsletter in the world. You know, literally the call is coming from inside your own inbox because you're not taking the time to manage your information appropriately. So, what is spending a half million dollars a year going to do other than move the pile around, right? And so let's let's think about this pragmatically and let's approach this from a process perspective first. We can clean up the remnants of it once we've got a handle on the process and and what we're actually trying to use, be it email, be it SharePoint, be it whatever tool. Um, let's figure out how we're trying to use it more effectively, and then we can approach a cleanup or, you know, you can't fix somebody's broken arm by putting a band-aid on it.

SPEAKER_00 2:06

Or you can't get, oh, it's the shiny new, let me get the shiny new to hit my problem when actually my problem is underneath the shiny new tool.

SPEAKER_01 2:14

It's it's almost never the technology. And you know, there's this statistic in project management that X number of projects fail, right? It's 80%, it's 50%, whatever it is, however you define it. But those projects fail not because the technology doesn't work. The projects fail either because it's a mismatch, because nobody did the prior proper planning, or they didn't train their people on it and it doesn't meet their needs. And and now what used to take 10 seconds now takes 14 clicks and a couple of mouse drags. You know? And so changing that flawed technology for more technology, you're again, you're just pushing the pile.

SPEAKER_00 2:50

And there's focusing things on change management. People aspects is just fundamentally You talk a lot about organizational tempo. You emphasize fitting improvements into an organization's operational tempo. How do you assess a company's rhythm and what happens when information governance requirements move faster than the culture can actually handle?

SPEAKER_01 3:11

I've actually found that, well, a couple of things. First, there's a great quote that is often attributed to Peter Drucker, but is not his, according to his official library, and that is culture eats strategy for breakfast. And so what I have found over the years from all different kinds of organizations is that just as it's not the tool, you've got to have the process in place, you've got to have the right people in place, you've got to have them trained and motivated and understanding what is expected of them. And that takes time, right? Most organizations I have found move slower in most of their respects, depending on whether the particular topic in question is directly related to the bottom line, or if it's something considered more tangential, more second class on bottom line profitability or reducing costs and more on back office, right? So records management is considered back office. Information governance is considered back office. And those don't get very much attention. And so on the one hand, as you say, often IG requirements change faster than the organization can. And this is especially true in some sectors more than others. Banks are not noted for being at the bleeding edge of the cliff. That said, I think there's another issue that we're running into today, but I think anytime you do a podcast and you don't at least mention AI, people are going to throw up their hands.

SPEAKER_00 4:34

And so I was going to ask you a question about AI anyway that links into that design.

SPEAKER_01 4:39

Well, let me let me provide this, and then I I would love to hear that question and we can talk about that. AI is changing so quickly that it's almost the opposite problem, right? Every organization wants to do AI. They want, and that's part of the problem, frankly, that they want to do AI. Well, what does that mean? Does that mean you're gonna automate this process or that process? You're gonna automate classification, you're gonna automate finding personal or sensitive information. What does it mean to do AI? And too many organizations don't have that defined in part because AI is moving so quickly. Nobody had heard of GPTs before about four years ago. And so we get to this place now where everybody wants to do AI, there are no guardrails in place, and we have this incredibly difficult time understanding the risks, much less putting an actual governance framework and scaffolding around that to help us safeguard the organization.

SPEAKER_00 5:30

Yeah, and it's really interesting. The question that I was gonna ask you, I was speaking to a customer today, and they were saying that they that they want more AI training and they want to deploy AI around the organization, and I just said, it's not a training thing, it's not a technology or training thing you need. You actually need to focus on like you're gonna put AI over the top of already rubbish within the organization. All the things you said around the information governance, the records management, and then it's just gonna turn out garbage. And and that's kind of on the top of the layer. And people are like, I started saying the shiny new, buy the shiny new to fix what's underneath, and AI is the shiny new, but actually fundamentally records management, information governance, and privacy are the layers that actually make your AI effective so you can actually have the shiny new.

SPEAKER_01 6:18

Every single day I see multiple articles about this coming from my legal firm sources, from my SharePoint sources, from every everybody that I follow, and I follow a lot of people on LinkedIn, a lot of people in on newsletters, all of them are saying the same thing, garbage in, garbage out. What I found really interesting, and I'm actually going to be doing a presentation at the ARMA conference in the fall on this, is we're everybody's trying to do agentic, right? We're trying to create AI agents, we're gonna automate stuff, we're gonna give it access to our systems, access to our files, access to production databases in some cases, and have it do things for us. And again, that pace of governance just hasn't kept up. And so there's a great article that I saw about a software company who was using an AI-enabled agent. And the agent, despite all of the warnings and precautions and guardrails that had been set up, deleted their entire master database of source code, just wiped it. And when asked, the agent said, You're right. I shouldn't have done that. Great. What do you do now? Well, they had a backup from several months before that they were ultimately able to restore. And, you know, they they lost some work, but not all of it. But as bad as people's information governance practices are, our process governance is often even worse. You know, you ask five people what this process entails, and you'll get six different answers. Now you're going to let code run that in an automated and unattended way and make decisions. I'm real hesitant of that right now.

SPEAKER_00 7:47

Yeah, agreed. And I think one of the biggest things that I'm always sort of waving my flag for is the information governance, the records management aspects of the layers on top of AI technology. Because actually, if you haven't got a good information architecture, you haven't got good life cycles, you know, all those things that we are continuously talking about as a profession. Everyone's talking about shiny new AI. Well, actually, you should be talking about records management and information management, sorting out your information before you get shiny new because the conversation today was garbage in, gospel out, which I actually really liked. I really liked that analogy because you know you take from AI, you think, oh yeah, that's is that true? And a lot of people aren't cross-checking data that's coming out of AI, and then the AI's learning on the stuff that they've already churned out. So there's bigger pieces that we're gonna have problems going forward. But yes, get your records management sort in before you get shot. You do AI is what I'm saying.

SPEAKER_01 8:44

That's right.

SPEAKER_00 8:45

I digest, I I digress, sorry. Let's talk about the human element of that. What roles or disciplines are most often missing from inform from the information governance table, and who should be there that usually isn't?

SPEAKER_01 9:00

I think this is going to depend on the organization, but the one that I see most often is the business. Some some business stakeholder who is going to be impacted by whatever highfalutin information governance process we roll out. I think too often we write policies, we write retention schedules almost in a vacuum, such that we don't understand that by telling marketing that they have to keep this stuff for X period of time and then get rid of it, either they're going to do that and that's going to impact the the way they do their work, or they're going to try and spend some time to figure out ways around it. Right. And IT has the same problem in the sense that when you put IT structures in place, often they don't think about the impact on the actual people doing the work either. And so I I think in most organizations that have any level of maturity, you've got a steering committee or counselor, whatever you choose to call it. But we have the what what I like to call the usual suspects, right? We've got IT, legal, risk, sometimes HR. I just don't see enough with an actual business stakeholder who's able to say, and and by the way, how is this going to impact our customers, our suppliers, our partners?

SPEAKER_00 10:12

When I was um at the um National Health Service, we used to have a patient that used to sit on the board and give their impact and their view. And I often wondered if you we could form that as part of an information governance structure within organizations that you actually have somebody who's like a you know it doesn't have to be a patient representative or customer representative that can actually give those those service user feedback. Because I think that would be great because you then got a four-rounded view. In the UK we have additional ones onto your layer. So we have the Cold Cot Guardian, we have the data protection officer, and the senior information risk owner is it on those board.

SPEAKER_01 10:50

I I think we have some of that in uh more public sector facing, right? Government, as you say, healthcare to some extent, uh because there's so much potential impact for the public at large. But in the private sector, I'm not aware of many companies that have that sort of thing, and and when they do, it's generally for marketing or sales. It's not r or ideation, it's not really about uh information governance. And and I think that's a bit of an oversight.

SPEAKER_00 11:17

I d did a podcast today about the muddy waters of where we sit. We're in the muddy waters and everyone else's technology AI on top, and we need to come up on the top of the sea and actually say start listening to us because information is gold. Everybody wants information now and we're the protector. Let's talk about strategy and outcomes. So short term versus long term. So you offer everything from on-demand advisory to complex projects. What is the most common emergency question you get in those one-hour sessions?

SPEAKER_01 11:48

Where do I start? That question is where do I start? I've I've got a mess. I we just lost a lawsuit. We've got problems, we're paying too much in outside storage. Where do I start? That's actually the question. And obviously it depends on on what they're trying to do and what they're trying to accomplish. But I think that's both the starting point for any discussion about how higher anybody could help them, but also helps to frame the discussion so that you can get value from answering that question, right? Where do you I I have boxes of stuff everywhere? Well, start by opening one of them and figure out what's in it. And then start by opening the next one, right? How do you clean your house? Well, you start somewhere and you clean something. And maybe you don't do a full spring cleaning, but at least you put the dishes away. Or you put the dishes in the dishwasher, or you you do something. And so I think where do I start is the thing, the single thing I hear the most, and the one that potentially can be most impactful in a short session.

SPEAKER_00 12:48

What is the secret source for making information governance change stick after you leave the room?

SPEAKER_01 12:56

There's another quote that's often ascribed to Peter Drucker, which is what gets measured gets managed. And so I think a lot of it is first instilling accountability and ownership, getting people to understand that you're not doing this because you're mean, you're not doing this because you have nothing better to spend money on, you're doing this to make the organization better. That also means tying what information governance does to business outcomes rather than it's risk. The CEO will go to jail. The CEO never goes to jail. Records managers never go to jail. But if we can improve business outcomes, if we can have commitment to people and ownership of the process and an understanding of how that ties to better business outcomes, I think you've got a sporting chance of actually being able to instill meaningful, long-lasting change.

SPEAKER_00 13:42

And do you think the people layer on top of that, Jesse, would be around influence? So for information leaders, records managers, if they had better influence in the organizations to tie to what you've just said would actually be a really big impact as well.

SPEAKER_01 13:58

Yes. And and I think part of how they get that is again changing that story from risk and compliance and even to some extent cost cutting. Cost cutting is valuable too, but ultimately every organization and everybody in an organization has what I call a whiffum. The what's in it for me. And the what's in it for me for an organization is whatever its charter is, right? If you're a nonprofit, it's service. If you're government, it's service. If you're a corporation, it's to make money. Information governance should be a means to that end and a support of that outcome, not something we do because we have to or because we think it's nice. And telling that story, I think we empower people to be a little bit more proactive and have their message received a little more effectively.

SPEAKER_00 14:39

Yeah, absolutely. Tell stories, be authentic, use that instead, Carrot and Stabb. Very, very much so. Yeah. So you've done 400 presentation perspectives and you've been speaking on these topics since 2003. There's one piece of advice you'd give 20 years ago that is now completely obsolete, and what is the one that has remained timeless?

SPEAKER_01 15:04

I'm gonna go in reverse order. I think timeless is what business problem are you trying to solve? As I say in my presentations, the business is in the business of the business. And it goes back to that charter point I made just a second ago. If you think first and foremost about what it is your organization is trying to accomplish, everything flows to that. In terms of obsolete, I wrote a training course for AIM on how to manage email messages as records. And as you might expect, that has not held up particularly well over the years. I also wrote a social media governance course for them, and likewise, I'm surprised they actually employed me after those two duds. But we had we had an interesting conversation, a group of folks that I use as a sounding board about this very question. I was crowdsourcing. I didn't go to AI, I went to humans. And they said there's really not a whole lot other than technology changes that we weren't talking about 20 years ago. Metadata is metadata, records management's records management. A good policy is good policy. And so I I wouldn't be too quick to disparage something because it happened 20 years ago that it's obsolete.

SPEAKER_00 16:07

Nice. I love that. Let's talk about I talk about magic mistakes. So common mistakes. After you've delivered 200 plus workshops, what is the one myth about information management that you find yourself breaking down almost every single time?

SPEAKER_01 16:24

That there's a magic wand you can wave and everything will be better. And and this goes to the technology too.

SPEAKER_00 16:29

My magic mistakes. Love that.

SPEAKER_01 16:31

I I actually have a slide someplace. I I stopped using it for a number of reasons, but I used to have a slide that had an honest to goodness silver bullet. And I I would say there's no such thing as a silver bullet except on this slide. But everybody's, you know, what's that tool, right? As we talked about. What's that one thing I need to add to my policy? What's that one 20-second elevator conversation I need to have to magically get a seat at the CEO's table? There ain't one. You know, it it it requires doing the work, it requires getting people and training them. And and, you know, that's why they call it work, right? It's it's not I'm I'm grateful to go to my happy place today. It's like I'm going to work today.

SPEAKER_00 17:09

Oh, well, I love happy place. My work is my happy place. And I would definitely say that some of the things that I've learned is very much around influencing. So is that people relationship building? And I think a lot of information records management within our industry. We need to be spending more time building those relationships with, you know, senior leaders, stakeholders, the people that we actually want to help, you know, achieving the things that we need to achieve for the organization. And very much so move away, you know, change the story from the compliance and the legislation to the the benefits and the outcomes for for those people. Big service points. It'd be great if you had an information leadership program called Empower that you could do. Uh, what is the scariest basement or digital archive you've ever had to audit?

SPEAKER_01 17:55

I used to work for a municipal agency and they kept their records in the basement as one does. They kept them full in bankers' boxes stacked eight high. Uh, I don't have the math in front of me, but I think the burst cost for boxes is about five high. So we had rows and rows of burst boxes, all these traffic tickets spilled out onto the floor, and you would walk on them, including in winter through the snow, that you'd track water in there. What that also attracted was mice. And so more than once I opened a box and found mice in there, typically dead mice, because they don't last very long in Denver. It's so dry and arid here. But uh yeah, mice, mice nests probably is the worst. We also have a client right now who has a room called the Bat Cave. I'll I'll leave it to your fertile attent imagination what might possibly be in there because they don't let anybody in there, but it is owned by records. So the mind boggles at what might be in there.

SPEAKER_00 18:52

100% my mind boggles. I'm like, is it cobwebs? The bats live there, have these spiders there?

SPEAKER_01 18:58

It might be an underground lair for an evil villain. I don't know.

SPEAKER_00 19:01

100%. Or it could just be a man cave, maybe.

SPEAKER_01 19:04

That's where the records people go to get away from it. That's it.

SPEAKER_00 19:08

So if you could ban one buzzword from the information governance industry, what would it be?

SPEAKER_01 19:13

Governance.

SPEAKER_00 19:14

And what is the one book, non-technical, you think every information governance professional should read to better understand organizational behavior and information management compliance?

SPEAKER_01 19:24

I spent a lot of time thinking about this because I've got hundreds of them. I've got a bookshelf of SharePoint books, I've got a bookshelf of AI books, AI governance books. And so I have to say I couldn't narrow it down to just one. So I'm going to give you three in no particular order. The first one is a book I got fairly recently. And as you can see, I have read it. So thank you. And I do recommend that to people. This is a little bit more technical book. It's called Non-Invasive Data Governance by Robert Seiner. But his thesis is that people are already doing data governance to varying degrees, and you just need to kind of shave a little bit around the edges rather than saying, you know, thou art now an information governance professional and thou shalt do the things. And then I think everybody needs a good book on change management.

SPEAKER_00 20:12

Oh my god, that is such a good book. I've got that book. It's such a good book. Agreed. The first book was Blooming Good Information Management by Jacqueline Stockwell. Me. Very humbled that to be recommended by you, Jesse, because I hold you in really high respect.

SPEAKER_01 20:26

What the name of the second book was Non-Invasive Data Governance by Robert S. Siner.

SPEAKER_00 20:32

And the third book was Leading Change by John Cotter. Yes. Nice. Amazing. Thank you so much. Jesse, it's been absolutely sensational. It's been as fun as I wanted it to be and as informative as usual when we have conversations together. How can listeners reach out to you if they want to know more?

SPEAKER_01 20:48

I'm I'm kind of an old school guy. I'm hard to not be able to track down online, but probably the easiest way is my permanent Gmail email address, Wilkins13.

SPEAKER_00 20:58

Amazing. You are also on LinkedIn as well, and I would highly recommend people to reach out to you. Thank you so much, Jesse. It's been an absolute sensational.

SPEAKER_01 21:06

Truly my pleasure. Thank you for having me.

SPEAKER_00 21:08

Anytime you're a very good idea, you can't believe it.