The Only Two Questions Every CEO Should Be Asking Today

There is no shortage of advice for you as a CEO right now. Everywhere you look, there are new frameworks, new tools, and new opinions on how to navigate the rise of AI.

Boards are asking about it, investors are asking about it, and your teams are experimenting with it across your organisation. As I’ve written about previously, the volume of information and speed of change is overwhelming for us all.

However, when you step back and strip away the noise, the situation becomes much simpler than it first appears.

In reality, there are only two questions that truly matter for any CEO today:

The first is how to make your company AI-native. 

The second is how to ensure your company remains relevant in a world increasingly shaped by AI. 

Everything else is secondary.

How Do You Make Your Company AI-Native?

Most companies today are approaching AI in the same way they approached previous waves of technology: They are layering it on top of what already exists. They are experimenting with tools, running small pilots, and adding AI features into existing workflows. While this creates the impression of progress, it rarely leads to meaningful transformation.

An AI-native company is not simply a company that uses AI. It is a company that is fundamentally built around it. This requires a different starting point. Instead of asking where AI can be added, you should ask what the company would look like if it were built from scratch today with AI at its core. This shift in perspective forces a much deeper level of thinking, and  challenges assumptions about roles, processes and even the structure of the organisation itself.

In an AI-native company, execution is increasingly handled by systems, while human effort is focused on judgement, creativity and direction. The result is a company that operates with greater speed, flexibility and capacity to iterate.

This is not a small adjustment. It represents a fundamental redesign of how the organisation functions. It is also uncomfortable, because it requires you to question parts of your business that may already appear to be working well. However, in a world where the economics of work are shifting rapidly, “good enough” is unlikely to remain sufficient for long.

How Do You Remain Relevant in a World of AI?

Even if a company successfully adopts AI internally, a second and more existential question remains. Will the company still be relevant?

AI is changing both how companies operate, and what customers value and expect. Products that were once differentiated can quickly become commoditised. Services that previously required deep expertise can be automated. Entire categories can shift or disappear altogether. This is where many CEOs underestimate the scale of change. They focus on efficiency gains and cost reductions, while overlooking the risk to their company’s relevance.

History suggests that companies rarely fail because they did not adopt a new technology quickly enough. More often, they fail because what they offered the market stopped being valuable. For this reason, you need to think carefully about how your company’s value proposition will evolve. Will your current offering still matter if AI can perform the same function more quickly, more cheaply or at greater scale? 

Ask yourself - “What unique value can we create that is truly difficult to replicate?”

In this new world, relevance must be continuously earned rather than taken for granted.

The Trap Many CEOs Fall Into

At present, many CEOs find themselves caught in the middle of these two questions. They are encouraging teams to experiment with AI tools, promoting internal adoption and running isolated initiatives across the organisation. While these activities are not without value, they can create a false sense of progress. They allow the organisation to appear active without addressing the more fundamental questions.

This is because both making a company AI-native and ensuring its long-term relevance requires making deliberate and often difficult decisions. These choices include determining which parts of the organisation need to be redesigned, which roles will evolve or disappear and where the company should focus its efforts going forward. They are not purely technological decisions, they are leadership decisions that are mentally and emotionally tough on the CEO.

This Is a Leadership Moment

It is easy to view AI as a technological shift that can be managed through tools, systems and incremental improvements. In reality, it represents a much broader leadership challenge. The CEOs that I’m working with are rethinking their organisations from first principles, and act decisively on what they discover. They are brave enough to challenge their own assumptions and in doing so redesign how their companies operate.

Final Thoughts

As you are trying to navigate this period of dramatic change, it can be helpful to simplify the problem. There is no need to chase every new idea or adopt every emerging tool. Instead, it is worth returning to the two questions that matter most:

How do you make your company AI-native?

How do you ensure your company remains relevant in a world shaped by AI?

If these questions are answered clearly and acted upon decisively, most other challenges become more manageable. If they are avoided, it is unlikely that success in other areas will be enough to compensate.

Image Credit: Stockcake