The Six Questions AI Can't Answer. Who, What, When, Where, Why and How?

26 years ago, on my very first recruitment training course, I was taught the importance of asking open questions to truly understand people.

Who. What. When. Where. Why. How.

At the time, it felt like a simple interviewing technique.

Today, in an era of AI-generated CVs, polished LinkedIn profiles and perfectly tailored applications, those same questions have become more important than ever.

A few years ago, I was told AI would replace recruiters.

At the time, the argument sounded convincing. Technology would automate sourcing, screen CVs, assess suitability and remove the need for human involvement in hiring.

Fast forward to today, and the reality looks very different.

AI has certainly transformed recruitment but not necessarily in the way many predicted.

Tools like ChatGPT and Claude now allow candidates to tailor CVs, optimise LinkedIn profiles and produce polished applications in minutes. The quality of presentation has improved dramatically. On paper, almost everyone now looks exceptional.

And that’s precisely the problem.

For hiring managers and internal talent teams, it has become increasingly difficult to distinguish between candidates who can present well and candidates who can genuinely deliver.

Experience can be embellished. Achievements can be refined. Applications can be engineered perfectly around a job description. The result is more volume, more noise and far more uncertainty around what is actually real.

Ironically, the rise of AI hasn’t reduced the value of good recruiters. It has increased it.

Because executive search has never really been about matching keywords to a CV. It’s about understanding markets deeply, building trusted networks and knowing how to properly interrogate experience.

The best recruiters don’t stop at what’s written on paper. They ask deeper questions:

• How was the result achieved?
• Who did this impact?
• What was their actual contribution?
• When did the biggest challenge emerge?
• Where did things go wrong?
• Why was that decision made?

People who have genuinely lived the experience answer with detail, context and consistency. Those who haven’t usually struggle once you get beneath the surface.

That’s the part AI still can’t replicate.

Technology can enhance communication and improve presentation. But credibility, judgement, resilience and authenticity are still deeply human qualities.

In many ways, AI is making candidates appear more similar than ever. Which means the ability to identify real capability, real leadership and real cultural fit has become even more important.

The future of hiring will absolutely involve AI.

But trust will remain human.