Deeper questioning for successful transformation

AI poses all sorts of opportunities and threats for organisations. So how should they respond?

The threats and opportunities are almost existential which means the response needs to be bold and brave. And that means asking good questions and really listening to the answers.

Organisations often ask questions based on what they already think matters.

  • Feature usage.
  • Account management
  • Delivery timelines
  • Workflow bottlenecks
  • Project deadlines.

Those questions generate useful operational insight.

But they rarely expose the deeper issues that determine whether an organisation will succeed. Companies like Kodak spring to mind. Kodak didn’t fail because it couldn’t see digital photography coming. It failed because the organisation struggled to question the assumptions that had made it successful.

  • A project can be on track while the team quietly loses faith in the strategy
  • Customers can appear satisfied while already considering alternatives
  • AI initiatives can show progress while solving entirely the wrong problems.

Peter Drucker put it well:

“The most serious mistakes are not being made as a result of wrong answers. The truly dangerous thing is asking the wrong questions.”

Wrong questions produce answers that optimise the wrong things.

That’s increasingly visible with AI.

Recent research from Ipsos Karian and Box found that while 55% of workers believe AI could significantly improve how their organisation operates, only 39% believe their organisation is applying AI to the right problems.

Why?

Because the hardest questions are often the ones organisations avoid asking.

  • What assumptions are no longer true?
  • What problems are customers or employees reluctant to raise?
  • Where has the status quo become more important than curiosity?
  • What risks are people afraid to surface?

Trust plays a huge role here.

The Ipsos Karian and Box research shows only 38% of workers say they feel confident they would be supported rather than punished if they failed to spot an AI error.

People don’t speak openly unless they feel safe doing so.

That’s one reason independent customer listening can be so valuable. External conversations often create the space for customers to say what they wouldn’t tell account teams or leadership directly.

The quality of insight an organisation gets will always depend on the quality, and courage, of the questions it’s willing to ask.

I’ve pulled together some of the principles that shape how we approach customer listening here 8 principles of effective listening.

And you can see the results here from our case studies.