From Overthinking to Insight: Why Human Appraisal is Vital in AI Times

AI excels at drilling down into details, but it's terrible at stepping back to ask whether you're solving the right problem. That narrowing focus—what I call overthinking—is becoming the defining limitation of current AI systems. Meanwhile, the human ability to
overthinkingtoinsight

“We’re smart enough to invent AI, dumb enough to need it, and so stupid we can’t figure out if we did the right thing.”

This quote by Jerry Seinfeld on AI struck a chord with me because the rise, influence, and impact of AI in every part of our lives today leave me with mixed feelings.

On the positive side, I have seen powerful changes generated from applying Machine Learning and AI to solve complex real-world problems in the logistics sector. Game-changing outcomes that would have taken many years to resolve previously.

Witnessing the transformational impact and having an “up-close” view of how AI thinks and operates have been among the highlights of my career.

The overthinking risk posed by AI

On the flip side, the mainstreaming of AI over the past two years has also raised red flags, especially the rise of overthinking.

In AI terms, overthinking, in my view, refers to the gradual narrowing of focus on a topic to the micro level (which current AI models are built on). Put simply, AI systems today follow patterns learned from training data rather than from making situational judgements based on experiences, emotions, and observations that we all make every day.

Although AI reasoning models are improving, they are still a long way from having the cognitive flexibility of humans. For example, when an AI system interprets a question in a certain way, it struggles to reconsider its interpretation and keeps layering new patterns on top of the original misunderstanding.

For example, I used AI to look into flight details for a potential trip to Amsterdam next month. While I was provided a lot of details on available dates, direct and stopover options, and increasingly micro information on prices and times for each prompt, I was never asked: “Do you really need to fly to Amsterdam in January?” Is it urgent, or can you wait until the weather is warmer?

Widen the human lens to reframe and reset

Fundamental human questions that come from “widening the lens” by taking a step back to draw on personal insights, experiences, observations, and feedback.

Unlike AI systems today, we are self-aware and can hold multiple opinions and views simultaneously, seeking alternative perspectives and changing our minds.

Challenging assumptions and reframing situations are skills I hope we never lose, because they are tremendous human capabilities that AI cannot yet replicate. It is an approach that I apply in many cases where clients have a dispute or issues in the office or at home.

Recently, a client shared a dispute with a colleague over a staffing strategy that, while agreed upon, was changed at the last minute by the colleague. My client felt betrayed, and while I understood her anger, I asked, “Did you ask the colleague why he changed direction? He probably had a good reason.” Rather than taking a breath and letting the colleague explain, she let rage overtake rationale in this case.

Jerry Seinfeld has good instincts

Jerry Seinfeld’s take on AI chimes with mine because, although we are in a time of unprecedented change, the current situation reminds me of the dot-com boom, when the internet was seen as a savior (but came with diverse growing pains).

Two growing pains that catch my attention include organizations treating AI as if it has human-like reasoning (when it is a pattern-matching engine). Taken too far, this is likely to lead to poor strategic decisions in complex or nuanced situations, e.g., where social and cultural norms are essential.

Another concern is that employees, particularly those new to the workforce, become overly reliant on and trusting of AI (taking everything it suggests at face value) and afraid to challenge assumptions.

Optimizing the AI opportunity

This aspect concerns me because it goes against a key piece of advice close to my heart.

From an early age, my mother encouraged me to take chances by saying, “Being scared is what keeps you alive.” Or in other words, if what you are doing scares you, it is probably worth doing, and you are probably following your instincts, values, and beliefs.

Combining out-of-the-box initiatives and status quo-challenging ideas with AI’s vast information processing and sophisticated responses is one of the biggest balancing acts corporations and organizations face.

My coaching helps to bridge this gap. I help you view issues and challenges holistically — taking into account cultural sensitivities, near- and long-term impacts, and adjacent issues — to enhance your thinking, defuse your emotions, and make impactful decisions for the future.

If strengthening adaptive thinking skills to be a more flexible thinker — and a team builder who can combine AI’s processing power with human adaptability — is something you want to advance in 2026, please don’t hesitate to contact me.

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