Why AI upskilling fails, and how tech leaders are fixing it | What IT Leaders Want, Ep. 11

Keith Shaw Hi everybody.

Welcome to Global Tech Tales, where we hear stories by IT leaders and editors from around the world about the latest technology and leadership topics. I'm Keith Shaw co hosting along with Matt Egan. He is the global content and editorial director at Foundry, also representing the UK.

Hello, Matt, how you been Matt Egan I'm pretty good.

Thank you, Keith. How you doing today? Keith Shaw Good, good.

So we are tweaking the show a little bit. We are now going to be hearing from editors and IT leaders in some pre recorded segments, and we're going to show that a little bit later, but we are still starting the show off with some of the latest statistics.

And today we are talking about it careers, but specifically around the topic of upskilling employees so that, you know, they have the skills necessary to succeed with the technologies of tomorrow, especially AI.

So, you know, I dug around and found a couple of stats, and what I found interesting was that there is a big gap between companies that recognize the need for skilling up, Skilling and training, but they just haven't yet actually produced a lot of the programs.

For example, a survey by Pluralsight suggests that 75% of companies have experienced delays or pauses in at least one or more AI projects due to a lack of employee AI expertise.

35% said half or less of its employees have developed AI skills, and 38% of respondents said half or less of its departments have adopted AI skills as part of training programs in day to day use.

And then there was one other stat that I found that said a Microsoft LinkedIn Survey said 66% of leaders would not hire someone without AI skills, yet only 49% of employees using AI have been trained by their company, and just 25% of companies planned to offer generative AI training that year, I think that they are going to be offering more training as we as we move on.

But it still seems like there's a big gap here. Matt Egan

Matt, yeah, for sure. And who trains the trainers, right?

I think where that really interesting point of the, I don't know, high hype cycle, or the development of the AI age, you know, however you want to describe it, where, like, I'm not even sure lots of organizations fully understand what they mean by AI training or AI roles, and do they mean very specifically, working with AI to do specific things, maybe using an agentic box, or do they mean like, roles that have been impacted by the use of AI in the kind of internal structures and processes infrastructure of an organization.

There's just lots of unknowns, right? Matt Egan

I was gonna say even in the way we think about the impact that AI might have.

You know, you do hear some pretty smart people, I don't agree with them, talking about how everybody you know who's Senior is fine, because they're gonna be strategic, but there isn't going to be a kind of a junior tier, tier of staff.

Does anybody become a senior leader managing bots? I don't think so. Where does the next generation come from? What's the impact on culture future workspace, like, like, like?

The truth is, I don't think we fully know this, but it's really interesting and important to hear from people in industry who are doing this stuff and have some insight. Keith Shaw

And I think that there's also a bunch of stats I've seen where employees that are being asked about, hey, do you want these AI skills? And they're overwhelmingly saying yes, yes, we want the skills. Please give us the skills.

And I'm afraid of what might happen is if companies don't deploy upskilling and training that employees are basically going to take it on themselves to try to do this, and they might not get the same kind of training that an employee sponsored program might.

But also, I think, that they don't want to necessarily just have to, like, watch a PowerPoint to learn, you know, that the way that they're trained has to be, you know, better than what maybe, like, a security skills awareness, yeah, for Matt Egan example, yeah.

I was just thinking about that, like, or the or the very important, you know, fire safety video or whatever, like, where it's sometimes soap opera, like, like, 100% right?

Because this is because it's new and it's exciting, and it's about people being empowered to explore and develop new skills. I think several things, right? I think you have to give people actual time and resources to do the training.

I think a lot of organizations pay lip service to the idea of exactly what you're describing, right? Hey, we found a video on LinkedIn. Everyone has to watch this kind of thing.

And I think you made a really good point, which is, if you don't provide the space, the tools and the direction to allow people to experiment and try.

They're going to do it anyway, and that has an impact on the IP of your organization, because if they're just chucking stuff in chat, GPT, you are allowing information to walk out of your business. So I think this is a very tricky line for organizations to tread.

They have to do it. There's no option, right?

Have to do it in a way that that means everyone's aligned around a broader mission and maybe even a strategy, but they have the space and the the investment in knowledge to be able to develop skills, skills that were not very well defined at this point.

I think it's really interesting and challenging situation. Keith Shaw

Alright, so for our next segment, we're going to throw it over. Over to Valerie Potter, she is from Computerworld, and she had a chance to talk with an IT leader adopting a whole bunch of tactics in this upskilling and training areas. So over to you. Val Valerie Potter

With me today is Jeff Foster, he's the Director of Technology and Innovation for Red Gate software. Welcome, Jeff. Welcome. Thank you for having me. Yeah, pleasure.

Oh, I should also add that Jeff also blogs independently on sub stack, and I'll be referring to some of his his writings there during our interview. So for so let's jump right into it. Today.

We're talking about tech careers, and specifically developing tech talent, and as a as a director of technology and innovation, I think this is something that Jeff can speak to so so for years, we've been hearing it.

Leaders say they can't find tech workers with the skills they need to fill open roles, and the skills gap has only gotten worse.

As new AI technologies have accelerated the pace of change, so more and more companies are turning to upskilling our existing employees to help fill that gap. So what are some of the approaches reg gate takes to upskilling your tech workers? Jeff Foster

That's a great question. I think it's important to realize with technology that it's constantly evolving. Like upskilling isn't a choice you have to make. It's kind of an imperative organizations must upskill, otherwise they're getting left behind.

In terms of how Red Gate does that, I think one of the first principles we operate from is we always try and hire curious folks and and that means people who have a thirst for learning. And you might wonder, how you find such such people, right?

And you know that is hard. One of the simple filler questions we use is just to ask people, what's the last book they read, what's the last technology they played with? What makes them excited?

That can give you a great impression of whether someone has that curiosity and that mindset to learn and adapt. Another principle we try and put in place is before you need to, before you introduce a technology, you really need to understand the why of that technology.

You need to feel the problem that the technology is trying to solve. So for example, if you're trying to learn Kubernetes, a container orchestration framework, and you haven't felt the problem that Kubernetes solves, it's going to feel like an over complicated solution to a problem you haven't got.

The way you can create that space for people is to not run workshops treating things in the abstract is to give people a chance to play with that technology and run into those problems themselves, so they can discover those solutions and learn to put them into practice.

Some of the ways we try and do that. At Red Gate, we have this thing called 10% time, where we give up every Friday afternoon for people to embrace learning and development. And that might be through lightning talks.

It might be through trying to fix a particular customer issue in a new and novel way, or it might just be trying to get to grips with a new technology, with a toy application, a Slack bot that orders lunch for the team every Friday, something akin to that.

And the final way, I think is really important to upskill people is to expose expert thinking. And I think that that's really key to see the decision making process in action.

And again, one of the things we've put in place, and it's taken a long time to get this actually showing value, is architecture decision records.

So when we ask people to make or when people make changes to software at Red Gate, we ask them to fill in a short description of of why they're doing it, the options they considered and why they chose the path that they chose.

I think we put this in about five years ago. Now we've got a library of almost 500 architecture decisions that detail why we did something, and sometimes a few years later, why we were wrong about that. And that's brilliant.

It's that organizational repository of knowledge that new starters can look in to understand why the decisions were made. They might be wrong. We're still going to make wrong decisions. Everyone does, but at least you can see the thinking process underneath. Valerie Potter

And I would imagine that that prevents you from making the same mistakes again. If you understand, you know, the thinking that went behind a decision and then that didn't turn out to be the right decision, it would sort of steer you away from that path again later on.

Jeff Foster

That's part of that curiosity to mindset. It's that old adage, I think it's Chesterton's fence understand why the fence post is there before you remove it.

So if you understand why, why the particular technology choice is there, no matter how weird it is, at least you're not going to fall into that trap of removing it without understanding the consequences. Valerie Potter

Yeah, that makes a lot of sense, and I imagine that that 10% time to also maybe introduces problems that not necessarily introduces but makes you aware of makes.

Company aware of, maybe problems you didn't realize were there that the the employees have discovered and or that they're just curious about that maybe weren't on the radar, and then they become that way. Do you have any examples of those types of things? Jeff Foster

Oh, that's a good, great question. I guess some of the things that have come out for 10% time relate to the way we do our internal processes at Red Gate. The one example I can think of is the way we did continuous integration.

We had a really complicated process for building our software. We used to refer to it as build magic, and everyone put air quotes around the magic, because it worked, and it was magical, but boy, was it complicated.

10% time we had a new starter come in who took a step back at that problem, looked at why the magic was there, carefully understood the reasons why, and came up with something radically simpler.

Once we could see that kind of innovation in action, we were able to take that out and roll that across the teams.

And I'm sure there's millions of of little examples where people explore a problem from a different angle on a Friday and then take it into their work on a Monday. Valerie Potter Yeah, that's great.

So so you know, we're talking about developing tech talent which is helping them, but it sounds like it's equally as important to help your your team as a whole develop and the whole company. Jeff Foster

Yeah, if you're not keeping up to date with technology, you can bet that your competitors are, and the whole road is moving forward. You have to get on it. Valerie Potter Yeah, exactly, exactly.

And so you have, we've sort of hit on this already a little bit, but you've already talked, you've written in your blog about the need to help tech workers get past the expert beginner phase and develop a more holistic understanding of the technologies you're working with.

So can you talk a little bit about how you help them get there? Jeff Foster

So that expert beginner, there's a wonderful blog article.

I'll send you the link afterwards, and hopefully we can share it in the article, but it's a brilliant model of understanding the expert beginner is the person who gets themselves to a state where they realize or they think to themselves, if I understand all the rules of how software is written, I don't need anything else.

I just apply the rules and lo and behold, I'm an expert software developer. But the problem the expert beginner is making is they're confusing confidence for competence.

They've seen a little bit of the world, and they've made some rules because of that, and they're going to stay fixed in that mindset forever.

So I think the job of of leaders is to to push people gently on with the necessary level of support into situations where playing by the rules doesn't quite work.

So you've got to find those situations where glibly applying a list of rules from a textbook somewhere just just doesn't make software that works for our end users. And it sounds really hard like, how do you find these opportunities for folks to go into difficult situations.

But this is software. There's never a shortage of weird and wonderful occurrences to explore. So for example, at Red Gate, we deploy software onto our customers machines, and they use it in their environments. Their environments are weird and wonderful.

So we might our software with 100 databases, with 1000 databases, but we deploy it to a customer with 10,000 databases, and something will go wrong, not all the time.

I should, should add in case Emma's listening, but not all the time it goes wrong, but sometimes the weird and wonderful does happen. But that's a brilliant learning opportunity.

That's an example to find where your your carefully scripted rules of how you should design an architect software just breaks down when you get to a certain level of scale, and over time, the more you expose folks to those situations, the more you build up that that kind of pattern matching library so they can understand those different patterns.

They can understand when to break the rules, when to play by a new set of rules, and when when when to break the rules yourself if you're doing something truly novel.

So I guess I'd say the the key thing of of pushing folks past that expert beginner is to expose them to as many different situations as possible. That's great. Valerie Potter

And this may, may lead into my next question, which is, so you know, skills per se, are only part of the equation, but, but so how do you help them develop and pursue their career goals? Jeff Foster

That's a another good question, and this is going to sound like a really obvious answer, right? I think the first thing to do is really, truly understand what the folks on your team want to achieve that? Sounds, sounds like everyone should do that.

But I bet there are folks listening who've never asked their people that question or never been asked that question themselves.

Was one of the things that surprised me about Red Gate, was a conversation in the first week of joining the company about, hey, where do you want to go from here? Jeff, once you are. Understand where people want to go.

I think it's your job as a manager to help them get there, to determine whether it's the right path for them. And I think again, that's about giving people the opportunities to taste those roles before stepping into them.

So for example, if someone wants to step into a leadership type role, and they're currently a developer, maybe the first gentle step on that road is just having an intern over the summer so you can get used to the idea of managing a single person over time.

You might turn that into something more substantial.

For example, at op Red Gate, we run a yearly conference ourselves for red gators, by red gators organizing that is, is no small task at all, but we found that's a great task to give to someone who's looking to step into management, project management, to understand the complexities of running a complicated system.

And again, it's not just sort of pushing people off the cliff and hoping that they succeed. It's about giving them the support, and that support might come from mentoring. It might come from the line manager themselves, but it's important to create that kind of safe to fail environment.

If someone's managing the intern, there's always someone else to step into if it doesn't quite go right, it's not someone organizing the conference on their own. They got the support of experts.

So creating that right balance of fun, opportunity, slight nervousness about the complexity of it, and the support to go alongside it, I think that's the key. Valerie Potter

Excellent Well, Jeff, thank you so much for being my guest on global Tech Tales. I really appreciate your time and insight Jeff Foster Cool.

Thank you very much. Thanks for the opportunity. Keith Shaw

We are now joined by Valerie on the show to chat about what Jeff had to say. Welcome to the show, Val. Valerie Potter Hi, thanks.

Keith Shaw

So you know, when you were doing this interview, what was your biggest takeaway from the discussion? I think there were a lot of things that I thought were really interesting, but you know, from from your perspective, what was the biggest takeaway? Valerie Potter

I think it was the getting people to have real world experience. So as you're developing people, people's skills and understanding.

I mean, he one of the things he kept coming back to was actually understanding the technologies and you know why decisions were made, and and so part of that was, you know, tying it into real world situations. So it's not just learning.

He talked about something called the expert beginner, and that is somebody who knows all the rules, and so they know why, why software works the way it does, and why you know. So they think they know it all at that point.

And then when you actually get into real world situations, it gets a lot messier. Unexpected things happen.

And if you really actually understand the why of things, as opposed to the book learning about it, you're going to be able a lot better, able to deal with it in the real world. Keith Shaw

So and, and Jeff was from the UK, and he threw out this phrase. And I wanted to ask Matt about this. He met, he mentioned Chesterton sense, and so I had never heard that before. Is that something that that's common knowledge over in the UK, Matt Egan

no, but I really liked, I really liked the way he articulated that like, and what it sort of told us about. I mean, I think really that, and the whole conversation really spoke to something Val was just speaking to which really resonated.

Great interview about which really resonated with me. Was around, like, making real these concepts of upskilling, and that all comes back to the why, right? So I love the fact that when they was talking about tactics, like 10% time, it's not just saying it, right? It's doing it.

And like when they talked about sharing expert voices, I really like that one thing that really sang through for me.

And again, it is more tactical, but was this idea of from day one, understanding where the individual wants to go, which I guess speaks to the why, and then allowing them to test and taste those so whether it is using technology to get to the next level, or whether it is literally like managing someone like who might be an intern, but that idea of, if we want to upskill someone, we put them in a position where They're actually and actively doing it.

I thought it was a fascinating discussion. Keith Shaw

Yeah, I was really impressed by that 10% time concept, where they basically told the company, every Friday, you know, for a number of hours, this is the time where you, you know, either work on a project or learn about something, or, you know, there's a speaker who's attending, and so, you know, dedicated time during the week for training.

I think a lot of times, companies get into this mindset of, well, we're going to just do training, and we're just going to send out this video, and then you watch it on your own time, or working it, work it into your schedule, and that might feel like you're, you know, because employees have different thing.

But I. Did like that, carving out of of time just to focus on training any thoughts on that. Or, I mean, or do you prefer it where they just allow companies or employees to do it on their own time? Valerie Potter Oh, absolutely not.

Not make, make them do it on their own time. That's actually one of my bugaboos. I would say.

I think I've brought that up more than once that I really disagree with the thought that you just throw a bunch of materials at people and say you figure it out. Matt Egan

Yeah, well, not least because that tells you how much of a priority is for the organization. Right? Again, what really came through in the conversation was the why, to your point about like it like we're not just doing this to be good people.

We're doing this because it's critical to our organization that our staff are continually upskilling, therefore we're putting in place the resources and like, I say, yes, that might be the sharing of expert voices. That's a good cultural thing to do.

The yearly conference he spoke about, which that was really interesting, because he said, we have a yearly conference. It's not a small endeavor.

That's important, but at the same time, we may bring someone in and as part of their upskilling, they run the yearly conference, right so that is putting aside a lot of time and resources on behalf of that individual, and saying your focus right now is to build the conference, but in doing so, you're going to learn and develop your skills.

It all speaks to me about the idea that this organization has decided it has a sincere commitment to upskilling. And the why is because it's we need to do it. We're a software business. We need to keep developing great, simple, magical solutions kind of thing.

So is that kind of to use English idiom, and it's putting your money where your mouth is right is saying, Okay, we've said we're going to do this. We're now going to enforce in invest and resource to do it right. Keith Shaw

And even early on in the interview, Jeff said this thing that really resonated with me, where he said, we hire curious folks. And you know, Jeff, that's the first step.

Is if you are in an interview and you notice that someone is not curious, that they're only interested in doing one or two things that might, you know, hinder later training. So I think, you know, even just asking them, like, what's the latest book you read?

What's the latest, you know, technology that you've been interested in that can really show if someone is curious or if they're just interested in being an expert in just one thing.

I find that fascinating just as well, because I'm always looking to try new things in my own, you know, both work life and personal life. So I thought that was really cool. Valerie Potter

And one thing that I really appreciated, too, and maybe, maybe this is my biggest takeaway. I don't know, there were probably, like four biggest takeaways, so, because he said so many interesting things, but there's this is not they're not doing one thing for training and development.

It's It's the it's the orchestration, it's everything, right? They're hiring curious folks right from the get go. They're interviewing those folks soon. We know once they get started and they learn the ropes and how things are done, they're there.

They're talking to those people and and saying, What could we do better? They're recording everything every time they make a change to the software. And one thing I really appreciated a little aside, he said, when he said, this was we started recording.

You know, every time a change is made to a software, the developer or engineer says, why that change was made? All the all the things they considered, all the paths they considered taking, and why they went with this particular path, why they made this decision.

And he said sometimes we went back later and we were like, well, that was wrong, but now we know now that is in the record as well.

Yeah, so and then, and so the then, when the new people come in, they look around and go, you know, why should something be changed? Or Should anything be changed? What are we doing?

I may actually be, I interviewed him about a few other things, so maybe I'm actually bringing in something that happened from a later interview. I'm not sure, but, but it all ties together. So, so he, you know, a new person came in and he reviewed all the documentation.

Okay, this was why this software was this way. But I still think that it could be simplified. And so, so they very carefully, went ahead and simplified it. And it was, it was listening to the new people. Is what made them see that they had over complicated this.

Keith Shaw

There were a couple of moments where he was talking about an overall environment of not to fail or, you know, basically creating a safe to fail environment. And even when he was talking about, he was talking about the weird and wonderful, I love that phrase.

And he brings up that, you know, they, there was an instance where they were deploying the software to 100,000 you know, databases or something like that.

And a lot of companies, when, you know their their software might have a bug in it, or they break, they they immediately go to the, oh, you know, this is awful.

And they and they yell at someone, or, you know, they ask about like, they point the fingers, and rather, he was. Saying, Well, this is a training opportunity to figure out, you know, some more learnings and some more opportunities to train.

And so I feel like sometimes companies don't create that, you know, the environment where it's it's safe to fail. And so that also kind of resonated with me. Matt, any final thoughts? Matt Egan

No, well, I mean, I will, I will. Oh, yes, and that, and what Val was saying earlier, like, all of this stuff only happens if top to bottom, the organization has a sincere commitment to it, right?

So, like, and we only have his word for it, but it's a very successful organization. Like, and culture doesn't start top down, right? It has to be everywhere, but you have to put in place, like, the mechanisms, the rules, the the the processes by which these things happen.

So I thought that was a really interesting example, the safe to fail. The fact that, you know, when something, lots of organizations talk about learning from failure, but to actually actively do it, you need the things Val was just talking about.

You need to have the document, the record that the process of going back and learning, inviting new, maybe junior people to give their feedback. I thought was really interesting.

And I thought it was quite practical as well, because all of these things can be done within an organization, you just have to decide to do it and commit to it. So, yeah, again, great interviewee. Great job. Well, I really enjoyed it. Yeah, and Keith Shaw

Val, you also mentioned that you would talk to him, to Jeff, about some other topics. And so, you know, we have, we will have some bonus clips on the site in a couple weeks. But what other topics Did you talk to Jeff about around the IT career space?

Valerie Potter

Well, one of the topics was changing culture as an IT leader, so, and that was a really interesting discussion. And then finally, we went into the the elephant in the room, which is, which is AI and tech careers, and how that's going to talk.

I mean, so RedGate Software, is mostly about software development, of course.

So we first looked at it at the at the software engineer level, but then also pulled back and sort of, what does it mean for IT workers in general so, and those are both really interesting discussions as well. Keith Shaw well.

All right, so we're treating these like bonus clips on the DVD for everybody that remembers what a DVD was. All right, thank you Val and thank you Matt, always, as always. You know we're going to be back next month to talk about cybersecurity in the world of AI.

If you liked this episode, be sure to add some comments below. Check out other tech talk shows, such as today in tech. Cio leadership live first person and demo if you are looking for product demonstrations, I'm Keith Shaw, thanks for watching. Transcribed by https://otter.ai