Upskilling Executives for the AI Era

In an exclusive conversation with Global Leaders Insights, Dominique Rose Van-Winther, Founder of Final Upgrade, explores how AI is redefining executive leadership and decision-making in today’s business landscape. She explains that while most leaders recognize AI’s potential, few truly leverage it to transform workflows, culture, and strategy. Emphasizing that “AI literacy is now a leadership baseline,” she urges executives to move beyond awareness to daily experimentation. By mastering AI fluency, leaders can unlock productivity, drive innovation, and secure their competitive edge in the rapidly evolving AI era. 

How well do executives understand AI’s impact on business and strategy?

Most executives know AI is coming. What many don’t realize is that it’s already here, and it’s drastically shifting what leadership and management look like. Obviously, AI boosts productivity. But there’s so much more that we see. It reshapes how decisions are made by looking at data in a much deeper way. We help companies use AI to dig into their consumer insights more, then develop personalizations that help sales and customer service.

The future of data in companies is generative. If you see how information flows, you can make much better decisions. For example, let’s say we miss our sales targets. We want to know why, so we ask the sales team, and they are down two sales staff, waiting to hire replacements. But that doesn’t tell a full answer either, you want to know why you don’t have those salespeople, why they left. You want an immediate option to query different data streams so you can find out why and fix the real challenge, rather than one of the symptoms. Then you go to the solution: you want to switch to your HR data and understand why we haven’t hired for the new roles yet. Is it a role we need to promote online, or do we have a backlog for interviews? Knowing the full picture of data in your company compresses timelines and challenges the hierarchy that once gave leaders their edge.

Executives don’t need to learn to code. But they do need to relearn how decisions get made, how to ask questions that pre-AI they wouldn’t dream of asking because they didn’t have enough resources or analysts to pull together the answer. AI changes the inputs, the context, and the expectations around leadership judgment.

Right now, too many leaders are stuck in what I call Genius Gridlock. They intellectually understand AI’s potential but remain trapped in outdated structures that prevent real adoption. That means they just need practice, but there are very few leaders out there that know the extent of what AI can do. They are using ChatGPT with 20-word prompts similar to what you could already search previously on Google… Where's the revolution in that…?

AI won’t just change the tools you use. It will change what makes you valuable. Leadership used to be about years of experience and knowledge. In the AI era, it’s about adaptability and the ability to use information available in the right way.

Also Read: The New Frontier of AI-Driven Commerce

Which AI skills are executives lacking, and how critical are they?

We’ve spent too much time debating whether AI will replace jobs and not enough asking whether leaders are prepared to lead in an AI-enabled world. So many people want an excuse why they don’t have to learn all this new tech: ethics, data privacy, compliance, regulation. But the tech is out of the box, and there are ways of addressing all of those once you get on board. So the time is now to move.

AI literacy is now a leadership baseline, and I believe leaders have to really demonstrate that they are using the tech. “My team is using it” just will not cut it. If you aren’t versed in the tech, you will be the bottleneck for transformation and change, and that means your boss, board, and leadership will see you as the weakest link when change isn’t happening fast enough. You don’t need to be technical, but you do need to be fluent in basic capability, how and where AI fits, what it can unlock, and how to get your team up to speed with the culture shift and transformation.

If you can’t confidently prompt, assess, or challenge an AI-driven recommendation, you’re not leading your team through the single largest workforce transformation that is happening (and has happened) in our history. The modern executive toolkit includes audio AI work, prompt fluency, thought partnership with AI, and basic AI automations.

AI doesn’t fail because the technology isn’t ready, actually, the tech is really quite simple. I see it all the time, executives who resist change because they believe it’s going to be complex. I ask them: “Do you use Excel?” Every one of them, without fail, has mastered this tool. But do you realize how many buttons and functions are in Excel? I mean, seriously. Now look at your average GenAI tool. We aren’t talking rocket science here, you have 10–15 buttons, all with highly intuitive UI/UX. And that’s where we are stuck? People are just fearful of change and having to learn when they are already senior. The key to overcoming that is simple, you just show them how to use AI on their own workflows. 

The only way to fail is to not try. And leaders who avoid learning will put themselves and their teams at risk of professional obsolescence.

How can firms balance AI knowledge with leadership in their upskilling programs?

In my opinion, most companies start their AI transformation at the wrong point. They try to educate the entire leadership team on machine learning, the tech fundamentals of AI. Hence, people get overwhelmed. I’ve found that since the current transformation and change is about first mastering GenAI and your own personal workflows and productivity, if you start with grassroots AI implementation on your own workflows and that of your team, you’ll learn so much more without getting overwhelmed. So many companies start with all the high-level conversations of how to build the infrastructure, platforms, data pipelines, and governance frameworks, and then the executive leadership is uninspired and uninterested, and the employees are disengaged.

The high-level and technical conversations are for the CTO to lead. The real workforce transformation at the moment is upskilling an entire workforce on an entirely new technology, and that requires them to rethink how they work on an everyday basis. We don’t need more CTOs, we need people who know the job and the challenges faced and can work with the tech to solve challenges and creatively think through new solutions faster and better.

The real challenge isn’t technical. It’s behavioral. My husband has worked in finance his entire career, and how he works in Excel is like magic, whereas I am a basic user. We both still say “we use Excel.” Everyone is “using AI,” but it is all at different levels, and no one knows their level of fluency.

People need to be empowered, not just equipped. They need to know how to use it proficiently, as most of the time I see people using GenAI at a very basic level, for very basic functionalities. If your transformation ends with IT turning on a few tools, you haven’t transformed much at all until that is backed with training and education based on your use cases for that team.

Training also needs to go beyond awareness. We’ve found the most effective way of teaching is to showcase entire workflows and tasks with AI and ensure teams develop the muscle memory of doing it differently. Otherwise, when they start to work, they will defer back to how “they always did it previously.” After you see that you can save 20–30–40% of your time by utilizing AI, you suddenly stop defaulting to your old operating system. That’s where the AI magic starts to happen, and people then start to drive their own deep dives into the tech, no training necessary.

Also Read: The Shift from Reactive to Proactive Employee Relations

How can executive AI upskilling influence culture, innovation, and competitiveness?

Culture changes when leaders and employees model new behavior, visibly, in real time. I meet executives all the time who say their teams are empowered. But you cannot lead a team or transformation unless you understand and use the tools yourself.

What I’ve seen fail miserably is that each function or team assigns an AI champion. This person is supposed to first learn everything about AI, then be able to teach it for a vast number of tasks and workflows within their team. Typically, this is an additional “hat” they wear on top of the other key roles they have. This means the job ends up forsaken, without real impact.

What works is to train everyone at once, as a team working together. Now you get everyone talking the same language, buzzing about it. Also, everyone overcomes the shame that is currently associated with AI usage, i.e., if it reads like AI, people think you didn’t do the work. So when you learn how to work strategically with AI alongside your team, you gain a new appreciation. Then it turns into a conversation if you don’t use AI, i.e., why aren’t you using this to work faster and better? 

We want to make it easier, even inevitable, for people to use AI in their daily work. We typically tackle AI upskilling across two pillars. The first is obvious, productivity. When you do significantly more, faster. The other piece is more interesting and tends to dawn on people after their first breakthrough. It’s all about competitive edge. You now become so much more valuable to your company, to your department. Your ability to execute and make decisions is, simply, better. 

Now you are the one getting everything done, but better. Your brainstorming and strategy accelerate because you have AI as your thought partner. And that’s the type of person that people want to lead the department, the function, the company. Your AI knowledge shapes your potential. And AI fluency is currently the most in-demand skill set among executives everywhere. 

Trust me, because I have C-suite execs asking me who I know of AI-enabled and AI-fluent leaders across marketing, sales, customer service, corporate services, HR, legal, finance, you name it. They are so few and far between that people struggle to find talent. By the way, if you are empowered, you can drop me a note.

What advice or resources help executives stay relevant in the AI era?

Staying informed isn’t the same as staying relevant. Informed is passive, and I’m asked all the time what channels to follow, how to stay up to date. Honestly, most of that is irrelevant.  Relevance in the AI era isn’t about what you know. Listen to all the podcasts, YouTube channels, and participate in Coursera courses, but it won’t make a difference. This is a behavioral change where you win by adapting fast and practicing consistent, daily experiments in AI.

The real power is trying. Build muscle. Experiment with your own tasks. Rewrite one report with AI. Run your next meeting with a copilot in the loop. Form your own internal AI agents that you ask for advice. Then start to get other super-users around you and share your experiences and wins. We learn from experience, not theory.

That’s why we built our Final Upgrade AI Primers. Executives don’t need more theory or to know the history of AI or why AI matters. They need muscle memory and experimentation. They need to lead by doing.

Also Read: Accelerating India's Shift from Tech Execution to Ownership

How will executive roles change in the next five to ten years, and what steps should leaders take now?

The executive role you hold today won’t exist in the same form ten years from now. The question is whether you’ll evolve with it or be replaced by someone who already has.  I also have two kids, four and seven years old, and my husband and I believe they’ll likely never go to university. The times are changing massively. I’m asked all the time how to prepare.

There is no answer to that other than holding on. In fact, I was involved in crypto from 2013 and loved the phrase HODL, which is “Hold On for Dear Life.” Now, over 12 years later, I repeat the same instructions. You don’t have to know where the tech will end up. In fact, Eric Schmidt, Elon Musk, and Sam Altman, none of them even know.

But when people panic over the future, they tend to see sapiens as still and unchanging. When was the last time sapiens didn’t adapt to new times and tech? Everything is in motion. So your only mistake can be to not move, not learn, not adapt.Don’t be that grandparent that isn’t cool with picking up an iPhone because it’s “too complicated,” because it isn’t, and that is just an excuse. You know better!

I remember starting to educate CEOs and C-suite in early 2023, back when I was explaining the importance of their AI strategy, but the common response was “It’s OK, our CTO will handle whatever is needed.” Now everyone is on board with AI and trying to figure out the right pathway. It isn’t hard as long as you are learning a little bit along the way. The companies who win are putting in structure and learning as a core pathway to AI fluency.

We’ve gone from having clients in 2023 that hired us for 2–3-hour workshops to now clients hiring us for full-day or two-day workshops, to now in 2026 having clients that are asking us to run kick-off workshops followed by one year of monthly virtual workshops on different topics. It isn’t about building, it’s about getting 30–40–50% more out of your team, and that’s the most important 50% because it’s the strategy, advisory, and thinking side, while you’re eliminating the grunt work.

The leaders who thrive in this are excited to see the results, and it moves so quickly. They start seeing AI as a core collaborator. Soon people will start to see AI as employee extensions. And those who lead their companies into the future will be the ones asking better questions, of both their people and their copilots.