Why AI Will Expose a Leadership Skill Most Organizations Ignore

AI has changed how quickly we can find information.

It hasn’t changed who is responsible for making decisions.

That distinction became the center of my conversation with Cheryl Strauss Einhorn, decision strategist, creator of the AREA Method, and author of The Human Edge. While much of the conversation focused on AI, it wasn’t really about technology. It was about judgment.

Leaders everywhere are racing to adopt AI. The organizations that gain the greatest advantage won’t necessarily be the ones with the most sophisticated tools. They’ll be the ones that make consistently better decisions while using them.

Apple Podcasts: https://podcasts.apple.com/us/podcast/how-to-make-smart-decisions-in-the-age-of-ai/id1262213009?i=1000767791085

Spotify:

One of Cheryl’s observations stayed with me.

Most people jump directly into prompting AI without first asking themselves what they actually think.

That sounds simple, but it’s becoming one of the biggest leadership challenges of the AI era.

AI doesn’t know:

• Why this decision matters.

• What success looks like for you.

• Which tradeoffs you’re willing to make.

• What context only you possess.

It only knows what you tell it.

The quality of its output is heavily influenced by the quality of your thinking before the first prompt is ever written.

This week:

Before asking AI a question, write down three things:

• What problem am I actually solving?

• Why does this matter?

• What would success look like?

You’ll likely write a much better prompt.

We’re conditioned to remove friction from almost everything.

Automate.

Accelerate.

Optimize.

But Cheryl introduced an idea I think more leaders need to adopt: strategic stops.

Not delays.

Not bureaucracy.

Intentional pauses that improve judgment.

A short pause creates space to ask questions like:

• What assumptions am I making?

• What evidence would change my mind?

• What might I be overlooking?

Ironically, those brief moments often save far more time than they consume because they prevent teams from solving the wrong problem.

One of my favorite parts of our conversation was how Cheryl uses AI.

She doesn’t simply ask it for recommendations.

She asks it to pressure-test her thinking.

Questions like:

• What am I missing?

• Where could this analysis be wrong?

• What evidence contradicts this conclusion?

• What assumptions am I making that deserve another look?

That transforms AI from an answer engine into a thinking partner.

The goal isn’t agreement.

The goal is better judgment.

Not every decision deserves the same amount of scrutiny.

If AI recommends a dinner recipe you don’t like, tomorrow is another day.

If you’re making decisions involving customers, employees, acquisitions, healthcare, investments, or long-term strategy, the consequences don’t belong to the machine.

They belong to you.

Cheryl offered a practical framework for recognizing when decisions deserve deeper attention.

Slow down when:

• The consequences are significant.

• The outcome is uncertain.

• The cost of getting it wrong is high.

Those moments deserve more than a fast answer.

They deserve careful thinking.

One idea I hadn’t fully considered before this conversation was that AI can narrow your perspective even when it knows you well.

As AI becomes more personalized, it naturally begins serving information it believes aligns with your preferences.

Helpful?

Sometimes.

Dangerous?

Potentially.

Leadership depends on seeing what others miss.

That means intentionally asking AI for opposing viewpoints, contradictory evidence, and alternative approaches instead of allowing it to reinforce what you already believe.

Confirmation feels good.

Better decisions often begin with discomfort.

I asked Cheryl what kind of companies she believes will win over the next several years.

Her answer wasn’t the organizations with the best AI.

It was the organizations with the best decision-makers.

I couldn’t agree more.

Technology has always accelerated work.

AI simply accelerates it faster.

The differentiator has never been the tool.

It’s the people deciding how to use it.

That remains true today.

AI can help you research faster.

It can summarize information.

It can generate ideas.

It can even sound remarkably like you.

What it can’t do is decide what matters most.

That remains one of leadership’s most valuable responsibilities.

As AI becomes increasingly capable, human judgment becomes increasingly valuable.

The leaders who strengthen that skill won’t simply keep pace with technology.

They’ll know how to lead it.

If this resonated, share it with someone who’s working to build AI into their leadership without giving away the one advantage technology can’t replace.

Tiffani Bova is Chief Strategy and Research Officer at The Futurum Group.

Ranked for the last six years in the Top 50 Business Thinkers in the world by Thinkers50, Tiffani Bova is a thought leader who Forbes says “reshapes our perception of growth.”

As both a practitioner and academic she offers a unique perspective and has helped lead the tech industry through several evolutions over her nearly 30-year career as Salesforce’s former Growth and Innovation Evangelist, and previously as a Distinguished Analyst and Research Fellow at Gartner and a sales, marketing and customer service executive for start-ups and Fortune 500 companies. She is the author of two Wall Street Journal bestsellers: GrowthIQ and The Experience Mindset.