How to Nurture Critical Thinkers in Your Finance Team

In a world of rapid automation and data overload, the true competitive edge for finance leaders isn’t sharper spreadsheets; it’s sharper thinking.

CFOs are drowning in data whilst starving for wisdom. Your team can run endless scenario analyses and pull reports in seconds. But when did someone last question whether you’re answering the right question?

In twenty years working with professional teams, I’ve noticed a pattern: the more sophisticated our tools become, the less we exercise our thinking muscles. We’re training brilliant executors whilst discouraging the skills that will matter most: questioning assumptions, spotting what’s missing and thinking laterally about complex problems.

The Question Crisis

Walk into most finance meetings and you’ll hear plenty of answers. What you won’t hear enough of are the questions that open up possibilities rather than defend positions.

Research shows three-year-olds ask about 100 questions daily. By age ten, most people have virtually stopped. Our education systems reward right answers over thoughtful questions. Finance teams amplify this tendency. The very things that make finance professionals excellent (precision, process, quantitative certainty) can become limitations when environments demand fresh thinking.

I recently worked with a CFO whose team spent weeks perfecting a cost allocation model. Technically flawless. A thing of beauty. But no one had asked: “What’s it for?” Once we paused to examine its purpose, the entire approach shifted.

Building a Questioning Culture

Creating a thinking culture starts with normalising curiosity. I teach finance teams the WWWWWWAAHH framework: ten diagnostic questions for examining any challenge. What problem are we solving? Why? Who’s involved? When’s the right time? What have we missed? What are our warning signs? What action have we taken? What attitude are we bringing? How might we proceed? How will we measure results?

One director implemented these at project starts. Her team caught flawed assumptions early, saving months of effort. Junior members felt empowered to surface concerns without fear. The real shift happens when questions become evidence of rigorous thinking, not weakness. When the CFO says “I’m not sure” or “Help me think this through,” everyone gets permission to think out loud.

Stress-Testing Assumptions

Every budget rests on assumptions. Yet teams rarely interrogate them systematically. As I note in my book, The Human Edge, we’re running twenty-first-century software on 50,000-year-old hardware. Our brains crave certainty and avoid discomfort, even knowing it leads to better decisions.

Before your next forecast, list every assumption underpinning the analysis. Then deliberately try to disprove the most critical ones. One CFO implemented quarterly “assumption audits” reviewing mental models about customer behaviour and operational constraints. Initially uncomfortable, these sessions uncovered blind spots hiding for years.

Beyond Binary Thinking

Finance teams often fall into binary thinking. Yes or no. Invest or don’t. But strategic insights live in grey areas. Instead of asking “How can we cut costs?”, try “How might we create more value with existing resources?” Same resources, entirely different outcomes.

I share mental models to help leaders reframe their thinking. First principles thinking strips assumptions to examine fundamental truths. Inversion asks what would guarantee failure. Opportunity cost thinking makes trade-offs explicit. These yield sharper insights from the same data everyone else examines.

Creating Space to Think

Most finance teams operate in perpetual delivery mode: month-end close, quarterly reporting, compliance deadlines. But critical thinking requires space. Research shows our best insights emerge when minds wander and make unexpected connections, not when actively grinding.

Consider “white space” sessions: just set aside an hour to explore questions without pressure for immediate answers. Topics like, “What would our competitors do?” to “What if our biggest customer assumption is wrong?” These can generate valuable insights.

The AI Catalyst

AI changes everything. It automates analytical heavy lifting. That’s precisely why critical thinking becomes more valuable. AI processes information brilliantly but can’t question whether we’re examining the right patterns, challenge premises, or integrate messy human context that determines whether analysis matters.

Teams that thrive use AI for routine analysis, freeing human thinking for higher-order questions: What does this mean? What are we missing? What is the ‘big picture’ goal we’re working towards as an organisation? How does this information help us move closer to it? One team I work with uses AI for initial scenarios, then spends time questioning AI’s assumptions and interpreting implications through strategy and stakeholder lenses. The AI makes them faster; critical thinking makes them better.

The Path Forward

Developing critical thinkers isn’t a quarterly initiative. It’s a sustained commitment. But returns compound. Teams that think critically make fewer costly mistakes, identify opportunities others miss, and adapt faster.

Most importantly, they elevate the entire conversation, moving finance from score-keeper to strategic partner.

Every CFO wants their team to be more strategic. But you can’t think strategically without thinking critically. You can’t challenge the status quo if you’ve trained people never to question. You can’t be great business partners if analysis matters more than insight.

Now AI handles more technical work, building critical thinking capability is the only sustainable path forward. The question is whether you’ll be intentional about creating conditions for it to flourish, or wonder why your technically brilliant team struggles to influence the conversations that matter most.

What if your next team meeting started not with answers, but with questions?

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About the Author

Bethan Winn is a critical thinking specialist speaker and facilitator, working internationally and based in Perth, Western Australia. Drawing from twenty years’ experience, she helps finance and leadership teams develop thinking skills to navigate complexity, uncertainty and ambiguity.

She is the author of The Human Edge: Critical Thinking in the Age of AI. Known for her practical approach, Bethan transforms complex concepts into immediately applicable frameworks.

Bethan can be reached at [email protected] or via Linkedin.