How to Coach Employees—and Yourself—on Critical Thinking

By Claire Meyer

26 December 2024

Western societies tend to place a lot of importance on decisive leadership. But those speedy decisions are often more impulsive than analytical, which can skew expectations and outcomes when situations are complex.

At the 2024 CSO Center Secure Horizons event at GSX, Professor Risa M. Mish, professor of practice at Cornell’s SC Johnson College of Business, guided CSOs through a series of critical thinking exercises designed to expand how they think about complex business challenges. But these exercises weren’t designed to just improve the CSOs’ skills—their employees can benefit too through coaching.

Fast and Slow Thinking

In his 2011 bestselling book Thinking, Fast and Slow, psychologist Daniel Kahneman outlined the two primary systems that govern how humans think. System 1 is fast, intuitive, and emotional. It relies on pattern recognition and past experience to help the thinker make a snap decision in the moment. This is a great tool for low-impact decisions (which are the vast majority of daily choices) and emergencies.

But over-relying on System 1 thinking can produce biased results because most of these decisions are based on prior experiences and aren’t built for complex or novel situations.

System 2 is slower, more deliberate, and logical. This is critical thinking, involving rigorous analysis and synthesized outputs based on multiple information sources to drive a more fairly evaluated decision.

“Synthesizing is what rockets a career forward,” Mish says. By collating information effectively, corporate leaders can bridge gaps between individual contributors’ knowledge and produce a more holistic recommendation to enable the business.

Coaching Through Analysis Pitfalls

A common trap in critical thinking is overthinking. Individuals can spend too much time either complicating low-stakes decisions or trying to get a perfect picture of a complex and changing environment before making a recommendation. Here, experienced CSOs can help their teams (and themselves) move forward with a few techniques from Mish.

10-10-10. If an individual gets trapped in analysis paralysis—where they cannot calibrate the stakes of a decision and keep circling a problem rather than moving forward—ask for a 10-10-10 analysis.

Close your eyes and imagine the decision has already been made, Mish recommends. Then ask: will the decision truly matter 10 hours, 10 weeks, or 10 years from now? If it won’t matter 10 hours later, decide, delegate, and move on. It’s time for that System 1 decision-making. If it will matter in 10 years, then it’s fair to give it some additional thought and shift to System 2 thinking.

Mish cautions not to make the decision for your employee, though. Instead, counsel them through the decision themselves to avoid fostering codependency.

“The only way to develop judgment is to exercise judgment,” she says.

Questions lend perspective. For fledgling decision-makers, it can be helpful for managers to ask follow-up questions during difficult choices.

To help identify catastrophizing behavior (fixating on the worst possible outcome and treating it as likely), ask what the worst-case scenario the individual can imagine is and ask the person to rank its likelihood from one to 10. Then, ask what the best-case scenario is and rank its possibility from one to 10. People who are catastrophizing rarely think about the positive, so even acknowledging that there is a potential best case is the goal here to help shift thinking in a different direction.

One final question: how reversible is this position? Almost every decision is reversible; it’s just a question of how easily, Mish says. This helps to lower the stakes in the employee’s mind.

The only way to develop judgment is to exercise judgment.

Follow up with support. The last piece of the puzzle to help individuals get over their fear of making a wrong decision is support. Remind employees that if the worst-case scenario they imagine does arise, you will be right there with them to help course-correct, Mish advises.

Coaching Through Information Gaps

“When you have a complex problem, you will always—100 percent of the time—have information gaps,” Mish says. It’s simply not possible to know absolutely everything about a problem; there will always be unknowns. Business leaders need to learn how to make competent decisions in the face of those gaps and be ready to shift direction as more information becomes available.

Sometimes those gaps come from other people—not everyone will tell you everything, either intentionally (to avoid embarrassment or to protect their own interests, for instance) or unintentionally (they don’t know what you’re asking for or they think you already have the information).

Early career professionals in particular fall prey to this trap frequently, going in circles looking for the complete set of information, Mish says.

But in most cases, business leaders can follow the same 70 percent rule that Amazon founder Jeff Bezos touts: when you have 70 percent of all the information you need, it’s time to proceed. Beyond 70 percent, you’re starting to lose benefits from a more informed decision by delaying action.

It can be difficult to know when you’ve hit that 70 percent threshold, and it’s often a matter of experience. So, being a sounding board and coach for others’ critical decisions can be a helpful professional development service.

If someone is struggling to finalize a decision or recommendation, ask what other three pieces of information they think would be critical to make the call and why or how that information could change their recommendation. This can help the individual weigh what they truly still need and whether it would change their current mind-set.