The AI Leadership Gap Is Already Ridiculous
Why the executives who skipped their personal AI awakening are becoming rapidly irrelevant
I was sitting across from Henrik Järleskog last week, someone who was literally my first podcast guest way back when we started in English (before I realized this was going to be a Swedish podcast). We were catching up about AI, and something he said stopped me in my tracks.
"2025 will be a year of unevenness," he told me, quoting Ethan Mollick from Wharton. "Those who've had their AI awakening and jumped on the train will be in a completely different place by the end of the year than those who haven't. It will be noticeable. It will be felt. For some, it will feel unfair."
That's when it hit me. We're not talking about some future tech divide. The gap between leaders who are leveraging AI and those who aren't is already enormous – and it's growing wider every week as new capabilities drop.
Look, there are already a million AI podcasts out there. Most feature either technical deep-dives or Silicon Valley CEOs making grandiose predictions about how AI will transform everything. Yawn. What's missing is a conversation grounded in the reality of normal leadership teams in normal companies. What questions should we actually be discussing in management meetings right now? What competencies do we need to develop? How does AI impact our business models, risk profiles, and ethical frameworks?
That's exactly why I wanted to talk to Henrik. He's not from the tech world, but he's gone extraordinarily deep on AI anyway. He's the person in my network who's most passionate about applying these tools in practical leadership contexts. I find this fascinating because our target audience – senior leaders – often fall into the 50-65 age range. And let's be real: many of them are secretly hoping they can skip this whole AI thing, just like some folks hoped they could avoid getting email 20 years ago.
(Spoiler alert: they can't. And the implications of trying are far worse this time around.)
The personal awakening that changes everything
Here's what blew my mind during our conversation: The path to organizational AI transformation doesn't start with corporate strategy or technology projects. It starts with personal transformation. Both Henrik and I discovered that our AI journeys began not from top-down corporate initiatives but from individual curiosity and experimentation.
"Before you can mature the thought model to get into those technical project discussions, you need to make that mental pivot," Henrik explained. "Why am I doing this? Why do I need to upskill myself?"
For Henrik, his aha moment came when he realized how dramatically AI lowered the barriers to tackling difficult questions:
"I've had many challenging issues and complex problems that needed solving. They took time to process mentally, often to the point where I'd procrastinate because I couldn't move forward. That part of my process as a senior leader has absolutely changed the most – the barrier is now much lower."
This hit home for me. I've experienced the exact same shift. But here's the thing most executives miss: You can't understand the organizational implications of AI until you've personally experienced how it transforms your own work.
Without that personal awakening, corporate AI initiatives become hollow exercises that fail to deliver real value. It's like trying to create a digital transformation strategy without ever having used a smartphone. You're just not operating from a place of genuine understanding.
Your AI team (that fits in your pocket)
One of the coolest frameworks we discussed was thinking about AI not as technology but as team members with specific capabilities. Henrik has developed what he calls his "AI team" – a collection of six specialized AI collaborators he's personally trained for different aspects of his work.
"I follow the pedagogical model where you see AI as a colleague, not a piece of code," he explained. "If I'm wearing my strategy director hat and I have my strategy team, I might ask for a competitive analysis in Holland. In the same way, I ask my AI colleague for a competitive analysis."
Wait – colleagues? Yep. Henrik has named his AI strategy consultant "Magnus" after a former colleague who was one of the best consultants he's ever known. (I told you this conversation would get interesting.)
His AI team includes:
A strategy consultant that helps think through complex business problems
A PowerPoint producer that saves time on presentation creation
A video producer that combines different media elements
An executive assistant that handles meeting notes and follow-ups
A social media content producer for LinkedIn posts
An email assistant that drafts communications in multiple languages
I've developed a similar approach, with agents trained on my book and other materials that reflect my thinking. But Henrik's approach is more systematized than mine.
"How long did it take to develop one of these agents?" I asked him. "It varies considerably. The shortest took a couple of hours."
That blew me away – a couple of hours of investment to create a specialized "team member" that can transform how you work. And these aren't agents with their own agency (they don't take actions independently). They're more like highly specialized chat instances with extensive context about their role and access to relevant documents and data.
Henrik shared a fascinating example of how these tools changed his workflow. When asked to present at an industry conference on workplace trends, he took a completely different approach than his usual process:
"Normally, I would have started with what I know, created a consultant-style straw man in PowerPoint, written headlines, added content to those slides, spent time finding appropriate visualizations... it might have taken a week of work squeezed between other responsibilities."
Instead, he used Claude and ChatGPT to research industry trends, fed that into Notebook LM (which automatically generated a podcast discussing the content), used that audio to create intro and outro video clips with his AI video producer, and built the presentation content with his PowerPoint producer.
Total time? About 60 minutes.
But here's the kicker that most people miss: The quality was actually better than his manual process would have produced. Why? Because instead of relying purely on his anecdotal experiences, he was leveraging insights from hundreds of pages of industry reports – something he never would have had time to read thoroughly on his own.
This is the paradigm shift happening right now. We're not just talking about efficiency. We're talking about leaders having access to capabilities that were previously impossible regardless of how much time they had.
The unexpected side effect: rediscovering creative flow
What nobody tells you about integrating AI into your workflow is how it transforms your relationship with work itself. Many senior leaders (myself included) report spending more time in creative flow states, exploring ideas more deeply, and finding renewed engagement with aspects of their work that previously felt burdensome.
"I spend a much larger portion of my workday in creative flow processes," I shared with Henrik, who enthusiastically agreed.
"The engagement level just spikes," he said. "I can get caught up in evenings in a 'wow-data wave' where I understand more and more about something important with the help of my AI colleagues."
This level of engagement can be so intense that it blurs the line between work and passion. "Is it work? That's an interesting question," I reflected. Both Henrik and I found ourselves working weekends not out of obligation but out of genuine curiosity and creativity – exploring new possibilities that simply weren't accessible before.
Think about that for a second. In an era where burnout and disengagement are epidemic among knowledge workers, AI is actually making work more engaging and fulfilling for many leaders. That's wild.
But it raises fascinating questions about who benefits from the productivity gains. If you invest your own time and money in AI tools that make you twice as productive, who has the right to those additional hours – you or your employer?
For now, as Henrik points out, "It's up to the individual to decide: should I do more tasks, pick up the kids earlier from preschool, or go for a run?"
From "I get it" to "we all need to get it"
So how do you take this personal awakening and expand it throughout your organization? When I wanted to accelerate AI adoption within my company, I organized a kickoff conference centered not on theoretical presentations but on building practical AI agents together for different functions – sales, delivery, development, finance.
"I was very intent that it shouldn't just be a kickoff that was merely 'curiosity interesting,'" I explained. "I wanted to make sure we reached a conclusion so that when you left the room, you had at least two agents that might cover your major time-consuming tasks."
The results were immediate and kind of amazing. Our sales team now has agents that:
Identify target companies from our CRM
Research CEOs before cold calls by analyzing annual reports
Transcribe meetings and follow up on action items
Role-play our customer persona during internal discussions
Our marketing team uses AI for copywriting and SEO optimization, while our delivery consultants have tools that restructure unstructured documents and break down strategic initiatives into actionable milestones.
Perhaps most valuable was an agent I built to help our sales team with compliance questions. "When a CEO wants to buy something, eventually a CIO or security officer has to approve that the data is hosted in the right places," I explained. Now, instead of these questions always coming to me, salespeople can get well-written answers that reference all our policies with just a few clicks.
The key insight? Organizational adoption progresses much faster when leaders see personal, immediate benefits – when the value is tangible rather than theoretical.
Henrik's taking a similar approach with his leadership team. "Now it's six months later, and by the end of February, we will have trained 90% of the country management minus one and in certain cases minus two. So around 25 people will have personally gone through this 30-day training."
Wait – is the path to organizational transformation really through individual transformation first? It seems counterintuitive in an era of top-down digital strategies, but both Henrik and I have found this to be true.
Henrik used a perfect analogy: "I get this mental image. There's a YouTube video of some kind of rave party in a ski slope. It starts with one guy dancing by himself, completely crazy. People are just looking at him sideways. Then a minute goes by and someone else joins. Another minute passes, and suddenly the whole ski slope is having a party and dancing together and having a great time."
That's exactly how AI adoption needs to work. You need those first passionate adopters who look a little crazy to everyone else – but eventually create a movement that others want to join.
The talent dimension leaders are missing
Beyond productivity and innovation, there's another critical dimension to AI that many leadership teams haven't considered: talent attraction and retention.
"It's a talent question," Henrik asserted. "What kind of talents do we want to attract? Are they learning to use great AI technology at work? If the answer is no, then I think you're in really bad shape."
Just as companies now offer gym memberships or lunch subsidies as perks, Henrik predicts that AI tool subscriptions and training will become standard benefits. "If I had to choose between subsidized SaaS-AI or a gym membership today, I know I'd choose the SaaS-AI subscription immediately. And it's much more life-changing."
(And we both value fitness highly – that's saying something!)
The reality is that in many organizations, individual employees are already ahead of the corporate curve – paying for and using AI tools on their own initiative because they see the personal benefits, even when corporate policies lag behind.
"I saw a survey measuring these things," Henrik mentioned. "Sweden ranks very low in AI adoption, but we rank high when it comes to 'bring your own.' Apparently, people in Sweden are largely paying for their own AI because they've experimented themselves and realized they need to learn this. The individual is ahead of the companies on this issue."
So if talent is already adopting these tools on their own, what happens when they encounter corporate barriers? Most likely, they'll find workarounds – uploading work files to their personal accounts in completely unstructured ways. And then you have zero oversight of what's happening.
It reminds me of a story a security colleague once told me about a major leak at a Swedish embassy. They discovered that because the official email systems required so many VPN logins and tunnels and hoops to jump through, the embassy officials would just use their private accounts when they needed to send files to themselves. The security measures actually created the security breach.
The same dynamic exists with AI. Companies that prohibit tools because of vague security concerns may inadvertently create greater risks while simultaneously crippling innovation potential.
The practical starting points for leadership teams
So how should a management team approach AI once they've gained critical mass in personal "aha moments"? Based on our conversation, three starting points stand out:
First, look for friction points in your existing business model – places where customer experience suffers because of process complexity or inefficiency. These areas often present the greatest opportunities for meaningful innovation.
In my company, we build a strategy platform where one of the most critical success factors is getting leaders to step back and think about planning. This is difficult for several reasons – it's hard to free up time for long-term thinking when you have 4-5 urgent issues, it's intellectually challenging to break down long-term goals into actionable steps, and frankly, it's administratively tedious.
If I'm brutally honest, only about 20% of leaders do this planning process well in our application. That's a huge friction point! So we're focusing AI innovation on making it easier for leaders to create high-quality plans – autocompleting elements like definitions of done, suggesting better activities, and benchmarking plans against best practices.
The downstream effect is enormous – if enough leaders struggle with our application, the entire company might decide they're not getting value from it, and we lose the customer. So friction points directly impact the business in profound ways.
Second, identify tedious administrative tasks that consume leadership time and energy. These "low-energy" activities are perfect candidates for AI enhancement, allowing leaders to focus more on strategic thinking and creative problem-solving.
Finally, explore how AI can capture and enhance unstructured data within your organization. Henrik and I had a fascinating discussion about this – much of the valuable information in companies exists in unstructured form, scattered across thousands of PowerPoint decks or trapped in countless meetings.
"How much value is lost because things aren't coordinated – everything that's said, everything that isn't communicated further, that needs to be done over and over in the same kinds of meetings in different places," Henrik observed.
If you can begin capturing that unstructured data – particularly the conversations happening in leadership meetings across the organization – you unlock enormous potential value. And I'm seeing this with many of the AI companies I speak with (primarily in the US). The challenge isn't just transcribing meetings (that's rapidly becoming a commodity) but visualizing and extracting the relevant information in secure ways.
The real test of leadership adaptability
Let's be real for a moment. If you're sitting in a leadership position responsible for guiding your company through what's arguably the most significant technological transformation in decades, and you're not personally investing in your own AI upskilling... isn't that approaching professional negligence?
That might sound harsh, but both Henrik and I have come to believe it's true. The gap between leaders who have embraced these tools and those who haven't isn't just about productivity – it's about your fundamental ability to understand the strategic landscape of your industry going forward.
As Henrik put it, "Is your company still going to be relevant two or three years from now if we don't start making these investments now?" That's a profound question every leadership team should be wrestling with.
The AI revolution isn't just a technological shift – it's a profound test of leadership adaptability and courage. Those who embrace personal experimentation and learning will find themselves not just keeping pace but discovering entirely new dimensions of their own potential.
The challenge isn't implementing AI – it's embracing the personal transformation required to truly understand what's possible. Without that individual journey, corporate initiatives will remain superficial and ineffective.
The AI train has left the station. Some leaders are already miles down the track, discovering landscapes the rest haven't even imagined yet. The question isn't whether you should get on board, but how much ground you'll need to make up when you finally do.
