Schemers & Spies: How we don’t know what we think we know

In the early 2000s, a New York financier named Bernie Madoff defrauded thousands of investors of over $60 billion dollars while claiming to be earning them stellar profits, remaining undetected for multiple decades.

Ana Montes, a senior analyst at the Defense Intelligence Agency in the United States, spied on behalf of the Cuban government, evading suspicions for 17 years and becoming one of the most damaging spies in US history.

These are just a few of the examples Malcolm Gladwell shares in his book Talking to Strangers where he asserts how little we know about the people we don’t know.

While these examples are worst-case scenarios and are less likely to happen in your day-to-day life, they demonstrate how wrong we can be about something assumed to be true.

I’m not suggesting your coworker is involved in espionage or your financial advisor is trying to defraud you, but what other assumptions do you make as you interact with others?

Have you assumed someone is doing well from their happy demeanor when they might be struggling?

Have you assumed someone aligns with your beliefs because of something they’ve done? Or maybe you’ve assumed the opposite, that there is nothing you both align on when there might be more values than you thought?

What the extreme examples (and everyday interactions) reveal is that it’s not always easy to read people, and we can’t assume we know what they are thinking and feeling.

The good news is we’re not helpless to this reality. We can acknowledge our misplaced confidence in our ability to analyze others and, instead, cultivate a posture of curiosity.

If you haven’t noted this already, I’m a big fan of curiosity. But not just the notion of curiosity. I’m interested in the actual lived out experience of it. I think there’s a big difference. It’s a nice sentiment that we should all be more curious, but what does this actually mean?

That’s my goal: To help people understand the subtle differences they can make in their conversations, in their leadership, and in their decision-making that are curiosity-infused. I believe when we can make these shifts, we can increase our capacity to engage and navigate conflicts effectively.

All the research I’ve done points to a fascinating but troubling reality: it’s not natural for humans to be curious. Our brains want certainty. Our minds find comfort in “knowing,” and there’s insecurity in the “not knowing.” Our brains defend against this state of “not knowing,” creating shortcuts to the most easily believed scenario. We want to believe the person is telling the truth, that how someone presents themselves is how they really feel, or that someone didn’t intend the negative impacts of their actions.

Our brains are trying to help us by saving us mental energy and filling in the gaps, but this doesn’t actually serve us well. Certainty removes the ability to explore the complexities of a situation, to explore what we might be missing.

Certainty denies us the chance to discover something new. I offer a challenge: the next time you find yourself coming to a quick conclusion or forming an opinion about something that happened, could you suspend your assumptions just enough to wonder, “what might I be missing?”

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The Problem of Proximity: Disrupting our Assumptions to Discover Something New

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When Leaders Disappoint and Why I Remain Hopeful