What chess can teach leaders about AI enablement

In business, as in chess, we’re taught that success comes down to thinking multiple moves ahead, anticipating your opponent’s next move, and seeing the whole board. For a long time, we’ve viewed the ability to master that board as the ultimate symbol of human intellect.

All of that changed in 1997 when early AI, dubbed Deep Blue, defeated Gary Kasparov, the reigning world champion of chess. A machine outplayed the best player in the world, causing many to predict that people would lose interest in chess.

Was this “checkmate” for human chess players? Not even close.

The opposite happened: Chess is more popular today than at any other time in history. World Chess Championships attract tens of millions of viewers, while AI vs. AI matches draw a tiny niche audience.

Not only that, but today’s chess players are playing at a higher level than 30 years ago, with more than three times as many grandmasters. This is largely thanks to the analysis and training methods made possible by AI.

What AI has done for chess — elevating the game without replacing the players — it’s now doing for business at scale. When leaders embrace AI thoughtfully and strategically across their organizations, they can help every employee outdo themselves, becoming grandmasters in their own right, whether they pull insights from a spreadsheet, talk to customers, or present to the board.

Developing a dual-track strategy for AI enablement

To win at chess, you have to be good at the small, incremental gains as well as the sudden combinations that change the board. In chess we call the first capability “positional play” and the second “tactical play.” As a metaphor for AI enablement, this works well.

Positional play means equipping every employee with AI tools that make their daily tasks easier and faster. It’s about optimizing existing workflows and consolidating productivity gains. Examples of this are all around us. It might be a medical clinic using Gemini in Gmail to explain medical terms in patient emails, a global technology company using NotebookLM to make performance reviews 90% more efficient, or a fashion retailer reducing the time it takes to create engaging web product copy from 30+ hours to 30 minutes per month. All of these come from real-world use cases our customers have embraced.

These kinds of daily, incremental gains create a solid foundation for boosting productivity across the entire organization. They also boost employee confidence, satisfaction, and engagement, according to our recent global survey of knowledge workers and business decision makers. Organizations that are highly transformed by AI prove that the biggest gains from adopting AI aren’t about saving time — they’re about expanding potential.

Tactical play is about driving game-changing impact. It means reinventing how the company operates instead of optimizing existing workflows. A few years into the AI revolution, this is less common. In fact, in that same survey, only 3% of organizations have truly transformed through AI. But they’re seeing outsized results: they report more than double the innovation, creativity, and ability to accelerate new products and services to market.

So why aren’t there more tactical chess moves happening? Because that 3% figure reflects the limitations of the recent past, an era of siloed productivity gains driven by chatbots. We are now entering the era of the agentic workplace. Instead of just embedding AI into existing workflows — that email to a customer or slide deck for the CEO — entire workflows can be reimagined with agents.

Why shared context is key to agentic transformation

AI agents pursue goals rather than just answering prompts. Imagine an agent that aggregates customer sentiment across all your channels, recommends solutions, builds the strategy deck for your review, and projects the bottom-line impact. This represents a true human-AI collaboration at scale, fundamentally changing how we move across the board.

However, this vision is often held back by a lack of shared context.

When agents bounce between dozens of disconnected applications to find relevant data and act on it, they often hit a "context wall." They’re unable to travel with the context they need, grinding productivity to a halt. This affects humans too: if your email can’t talk to your file system, your AI-generated insights and outputs remain limited. To break through these silos, enterprises need a unified, secure platform where humans and agents can collaborate across all application boundaries.

Winning at AI adoption

To win at chess — and AI adoption — you have to be able to play positionally and tactically at the same time, and the two modes of play are deeply intertwined. It’s your daily, positional investments that actually create the opportunities for those tactical strikes down the line. Good tactics flow from a good position on the board. For the 3% of organizations that are truly transformed by AI, it’s no accident that 74% of them continuously refine AI frameworks to optimize workflows over time. Like any grandmaster, they’re constantly reassessing the board.