Blake Tablak on the Human Side of Digital Transformation

"We can't save our way into the Fortune five hundred." — Blake Tablak

During a recent discussion, Blake Tablak, CEO of Trax Technologies, joined the conversation to talk about the human side of digital transformation and why so many technology investments fail to stick once they reach the people expected to use them.

Video Context

Tablak covers four related questions in this conversation: why the human side of transformation is often the hardest part, what leadership's role is in helping teams adapt, how organizations build a culture that welcomes rather than resists change, and what skills will matter most as AI continues to reshape how businesses operate. His answers draw on his own experience building AI adoption inside Trax, including the internal rollout of Claude to roughly ninety leaders, and on lessons pulled from military leadership history.

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Full Transcript

Host: Hi everyone and welcome to the Trax channel. Today I am here with Blake Tablak. Hi Blake, how are you?

Blake Tablak: Wonderful, how are you?

Host: Good, good. It's good here in South Florida, that's where I'm at, and it's a little roasty.

Blake Tablak: It's been hot here in Tennessee as well. We're starting to see a little bit of a sign of fall in the morning, which is nice.

Host: Oh, that's so exciting. Great for golf, great for just working out in the morning, even just because it is like a sauna here.

Blake Tablak: Exactly, yeah, exactly.

Host: So today we're talking about the human side of digital transformation, and the first question we have is: many companies invest in new technology but struggle with adaptation. Why is the human side of transformation often the biggest challenge?

Blake Tablak: So this is near and dear to my heart. I spent a bunch of years at Udacity, and we dealt with this problem with the world's largest technology companies, and non-technology companies, frankly. There's two things: education, so your knowledge about the subject, and second, trust. Those are really the two biggest inhibitors to any digital transformation.

If you take the first one, it's: do I really understand what it is I'm being asked to do? And the answer is probably no. You could have experts in your company. Right now, artificial intelligence is the digital transformation going on, and it's still early enough that there's probably not as many people who are comfortable with the various aspects of it, which, by the way, covers a broad swath of technologies. It's not just large language models. It's machine learning, computer vision. There's a broad swath that gets lumped into this AI thing.

So the first thing is education. Part of that is rolling out training. I mentioned Udacity, I worked for them for years, they've got a great product, but there are other companies as well you can send your people to. There's the old joke where the CEO says, "We've got to train these people," and the CFO says, "It's too expensive." It's like, well, what's more expensive: training them, or keeping uneducated people? Sending your people to boot camps and things like that pays a huge dividend.

The second thing is building trust: allow people to play with the tools themselves. We took our own advice on this. Early on, we rolled out Claude to something like ninety people. We looked at the leaders in the company and said, "Okay, you're all going to get a license, and we just want you to try some things out." Here are some guardrails, here are some things you can't do, you can't use customer data, that kind of thing. But we wanted them to play with some different applications and try some different things out. A lot of it was self job automation: account plans, communication strategies, and so on, which was very cool. And once people started using it, you start to gain some trust. So knowledge equals trust.

Everybody's had this panic moment in their life where they wake up one morning and think, "the world around me is collapsing." I talked to a friend of mine this morning, a very successful guy, and he said, about once a year, he wakes up in a sweat thinking, "what if one day I end up homeless living underneath a bridge?" It's pretty wild when you know who this person is, but it's a real fear for him. He says the way he talks himself out of it is he walks through all the steps that would have to happen for that to actually be true.

I bring that up because oftentimes people have this panic moment when new things happen: "This is going to get rid of my job," or "What if I do this wrong and I get the company in trouble, then I get fired." When we rolled out the education and started training people on how to use these things, and built our own internal training as well, with people sharing ideas, giving people access created excitement. Where once was fear is now enthusiasm. And now there's real pressure to move faster, to do more.

So I think education and trust are the two things every business needs for any digital transformation. That generally is it. It's not funding, by the way. Companies will spend billions on this stuff.

Host: I love that you built your own internal training for everyone and gave them the opportunity to become successful and continue their education in this really fast, ever-changing world. So what role does leadership play in helping teams successfully adapt to new technologies and changing business processes?

Blake Tablak: I think the big thing as a leader is to recognize the emotions of the people you're trying to lead. I was listening to a story about a commander, I believe from the Civil War, an Army commander, who got a great education prior to watching different leaders try to enforce discipline on people who were tired, in the middle of nowhere, hadn't seen their family in months. He said he wanted a result, not just discipline for the sake of process. He wanted a disciplined result, not just the process working well.

It'd be easy if you'd been around a bunch of bad leaders to think, "I'm not going to do that." The problem is most of us have been around good leaders, or at least enough good ones. So as a leader, your job is to create trust between you and the people you're asking to change. That means identifying with the emotional state they're in, because people act on emotion more often than not. That's what makes us different from a computer. Nobody logically decides, "let's go to the moon," there's no logical need to get there, but there's a lot of excitement in doing it.

So get your people emotionally invested in the outcome. Explain the outcome, tell them what you're trying to accomplish, and reassert that over and over. If you think you've said it once, you need to say it a hundred times before it gets through to everybody in the organization.

As a leader, be okay with things not working right. Edison used to say there are twenty-five hundred ways not to make a light bulb. The first time something doesn't go well, if you think it's going to go well and then you're disappointed, everybody else will be disappointed too, and think "we shouldn't do that again." If it rolls out and it doesn't go well, that's fine. At least you know one way not to do it. What did you learn? Let's not do that again, let's go do something else, continue forward.

As a leader, your job is to create trust in your organization. That trust translates to willingness to change, and that willingness gives you an unfair advantage in any transformation.

Host: Absolutely. How can organizations create a culture where employees feel empowered to embrace innovation rather than resist change? I've seen this with clients I've worked with, and it's not necessarily the executives, it's the other employees who are just so resistant.

Blake Tablak: It's not the conscious resisting you worry about, it's the unconscious stuff. "This is the way we've always done it." "We tried that before." Nothing agitates me more than, "we tried that twenty years ago and it didn't work," and I don't care if it was three years ago. People create a narrative and adjust their entire career around it, and you're like, don't do that.

The conscious people you can always talk to, because they're looking at it and saying, "I'm not doing that," and you can explain what you're trying to get out of the process, what you hope to achieve, what it means for them. It's the people who aren't vocalizing it, the subconscious ones, "we've always done it this way," "we're going to build the last product exactly the same way, just with cooler technology." No. We really need to think differently. The old Apple commercial, "think different," that was totally my generation, and it was such a good reminder. Great ideas don't come from thinking the same way we thought before.

As you work inside and outside your organization, that objection usually comes from fear, or from lack of understanding about a topic, or from people not trusting you as a person. That's okay, by the way. You don't need to feel awful because they don't trust you. Maybe you just haven't been clear about your expectations, or what you want the outcome to be. That's good feedback. You're a leader, so congratulations, you just found out a way that doesn't work. Now change.

Host: So what are some common mistakes you see companies make when implementing digital transformation, and how can they avoid them?

Blake Tablak: I often listen to and read military history, because it can tell us a lot about leadership. I used to be involved in a group that swapped civilian and military leadership for short periods, so you can really learn a lot. At the top of every battle plan is something called commander's intent, and I think this is something we miss a lot in the corporate world. We come up with a great plan every year. Right now we're wrapping up our twenty seven plan, and within a month it'll be complete, approved at the board meeting, and we'll be off to the races. But at the top of the plan is: what's the intent? You have a series of metrics you're shooting for, but what's the intent? Because some of what's planned isn't going to work out the way you thought. The best laid plans, right, of mice and men, they don't work out that way.

So what's the intent? Maybe revenue didn't come in as high as you wanted, so expenses can't either, that's an obvious one. But there are more subtle things too. If you think about commander's intent sitting at the top, you should always tell your entire company what you're after. I tell our company all the time: we can't save our way into the Fortune five hundred. My uncle Chuck says, "Blake, no one saved their way into the Fortune five hundred," and that's a really good point. We have to grow. Everything we're doing creates more throughput, higher quality, in every aspect of the business. If you think I'm doing this to cut costs, you are wildly mistaken, and I have to repeat that message every month, every week, every day, to somebody in the company, so everybody hears it. Our CEO isn't rolling out AI to cut costs, because that's what you read in the news. Our CEO is interested in throughput and quality. We're acquiring companies, landing new logos, expanding relationships with current customers, and the better we do at that, the faster we grow, and the more resources we have to do more innovative stuff. It's a virtuous cycle.

That commander's intent at the top, you should always explain to your people why you're doing this. Otherwise they'll come up with their own reason, and then build an operation behind that reason. If they think it's cost savings, they'll create a bunch of solutions to cut costs, and you may not want that. So just be clear what the commander's intent is at the top.

Host: I love that. Our last question today: as AI and automation continue to reshape industries at a very quick pace, what skills and mindsets will organizations need to develop to succeed in the future?

Blake Tablak: This is really interesting. Communication is one, and this is something people don't really consider, but go play with a large language model for a while. Your ability to communicate the problem you're trying to solve, and the information you're sharing with it, is directly correlated to the quality of the output you'll get. Most LLMs today are like a twelve or fourteen year old with a PhD's vocabulary. You can get confused and think you're getting the right information. Frequently, I'll be running an analysis or a forecast and say, "can you double check your work, because that doesn't quite look right," and it'll say, "oh, you're right, sorry, I missed that." You think, "but you're a machine, you're not supposed to miss that." Well, it turns out they do. So as we think through all this, I look at each aspect of what we're doing: what it's good for, what it's not good for. What you're trying to do is teach your people the best possible solutions for the best possible scenarios, and that's the best you can hope for.

When it comes to AI and automation, there's a lot of it out there, so be careful about which solutions you're using and how much credit you're giving them. Communicate clearly about using different solutions, try Gemini, try Grok, try many different things, they're good for different purposes. Same with machine learning or computer vision, try different things out, because the right tools will absolutely change the game.

So I think an understanding of the solutions, better communication, and the last one is deep business knowledge. If you're a developer, you can no longer just know how to code, you have to know how the business works. You can't just walk in and say, "I'm going to build a product." You have to understand the business at a detailed level. If you're a developer and you don't understand finance, or operations, or support, don't try to build products or design things for that part of the world, because you'll get it wrong. So: communication, understanding the tools, and really understanding the business. Those are the three things that are going to make people wildly successful in this era of business.

Host: Absolutely. And we're going to make a blog on this podcast, on this Live LinkedIn, so that people can read all of your tips and advice, because I think it's really encouraging to hear from a CEO what they're doing to support continuing learning when you have employees who could be resistant or not as excited about change. I think it'll be a really interesting read that people can go back to as a resource. It was so great to talk to you today, Blake, and we'll be continuing this conversation in the next few weeks with more Live LinkedIns.

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For more from Blake Tablak on AI adoption, leadership, and supply chain strategy, watch the full conversation, explore more insights from Blake, and follow Trax Technologies on LinkedIn for upcoming Live sessions.