The Question That Won’t Leave Me Alone
I’ve been asking this question for years now—sometimes out loud in a meeting, sometimes to myself while brushing my teeth:
Why do smart people miss what later seems so obvious?
It’s not a rhetorical question. It’s not a dig. It’s more like a riddle I keep bumping into, especially in the places I spend my time—around boardroom tables, in one-on-one coaching sessions, and even leading my own team.
And I don’t just mean other smart people. I mean me, too.
That Time I Was Sure I Knew the Problem. I Didn’t.
Early in my career, I took on a project to improve student retention at a career tech college. The CEO—a thoughtful, mission-driven leader—was hearing stories from her team that students were dropping out just before graduation. She asked me to help figure out why and what we could do about it.
I didn’t question the framing. I dove in, assuming the problem was late-stage dropout. I mapped workflows, interviewed instructors, and built a plan around solving what we all believed was happening.
A few months in, a colleague gently asked: “Have you looked at the retention data lately? I don’t think our problem is late-stage grads.”
She was right. Nearly 80% of students were dropping out in the first half of the program. Close to half were gone within six weeks.
The numbers had been there the whole time. But we’d missed them—because the story felt true.
It Happens Everywhere.
Once I started noticing how often smart people miss the obvious, I began seeing it everywhere:
- In the early days of the internet, most media companies believed people would never pay for digital content. They gave it away for free—only to spend the next two decades trying to rebuild sustainable business models.
- In the lead-up to the 2008 financial crisis, ratings agencies gave mortgage-backed securities triple-A ratings… even as default risk quietly exploded beneath the surface.
- In early 2020, epidemiologists were warning about COVID-19, but major events like South by Southwest, March Madness, and Broadway shows continued—until, seemingly overnight, everything shut down.
- As recently as 2022, most business leaders dismissed generative AI as a novelty—right before it reshaped education, software, creative work, and more in less than a year.
The phenomenon is so common that it’s been studied extensively:
- A 2023 review in Trends in Cognitive Sciences found that experts’ prediction and decision-making errors are often driven by overconfidence, confirmation bias, and flawed mental models—particularly in fast-changing or ambiguous environments.
- A study published in Cognitive Science demonstrated that even well-trained experts tend to misjudge probabilities, often being poorly calibrated—meaning they’re more confident in their predictions than they should be.
And here’s one that hits especially close to home—because it involves people’s money.
According to Morningstar’s 2023 fund flow analysis, the vast majority of actively managed mutual funds—those run by professional investors who try to “beat the market”—continued to see withdrawals from investors.
Why? Because data consistently shows that passive index funds, which simply track the market, tend to outperform most actively managed funds over time.
In other words: even with deep research teams, market modeling, and decades of experience… the experts managing your money aren’t getting you any better returns (after accounting for their fees) than a passive index fund would.
As a consultant who is hired for her expertise, the astounding ability of experts to be wrong is obviously… concerning.
But it also clarified something for me.
The real value of a consultant—at least the kind I strive to be—isn’t expertise.
It’s curiosity, neutrality, and clarity.
Not knowing more than you, but being able to help you see differently.
Why We Miss It: The Pull of “Normal”
If this pattern shows up across industries, disciplines, and even Nobel-worthy discoveries… we probably need to stop thinking of it as an occasional blind spot. It’s more like a default setting.
One of the biggest culprits is something psychologists call normalcy bias—our brain’s tendency to assume that tomorrow will look like today. That the systems we trust will keep working. That if something were truly broken, someone else would’ve already raised the alarm.
The problem isn’t that we’re ignoring evidence. It’s that we don’t even notice it—because it doesn’t fit the story we already believe.
We make decisions based on assumptions that used to be true. We overcommit to the first version of a plan. We double down on strategies we haven’t questioned in years.
And the more experience we have, the easier it is to believe we’ve already asked all the right questions.
Why It’s Harder for Middle Management
If you’re in a middle management role, this is even trickier.
You’re often held accountable for delivering results on a plan you didn’t design. You’re asked to execute with precision, not poke holes. And over time, that makes it harder to speak up—even when something feels off.
It’s understandable. You don’t want to be the person who throws a wrench into the meeting. Or the one who’s always second-guessing the strategy.
But here’s something I’ve noticed: the people who do speak up—thoughtfully, respectfully, with real curiosity—they’re the ones who get remembered. And often, promoted.
They ask the question that no one else does. And suddenly, the room shifts.
Why People Hire Consultants (When They Don’t Really Need One)
Here’s a slightly uncomfortable truth about my job:
Sometimes, when a company hires a consultant, they don’t actually need outside expertise. They need permission.
- Permission to question a strategy that no longer fits.
- Permission to name the thing no one wants to say out loud.
- Permission to surface a “dumb” idea—without risking internal politics.
As a consultant, I’m not protecting my career in the organization. I don’t have a boss who needs to be right. I can ask the thing others are scared to ask.
The paradox is: people inside the organization often already know what’s wrong. But what they don’t have—yet—is the cover to say it.
That’s why I think we’d all be better off if more leaders learned to think like a consultant.
To ask questions that don’t score points. To make it safe for someone else to say, “Actually, I think we’re solving the wrong problem.”
You don’t have to be an outsider to see with fresh eyes.
But you might have to act like one.
How to See What Others Don’t
If you’re wondering how to get better at spotting what others miss, I don’t have all the answers, but here’s what I try to practice (and teach):
- Act like a consultant. Pretend it’s your first day on the job. What feels strange? What’s being taken for granted?
- Listen outside your lane. Who isn’t talking to whom? Who’s quietly frustrated?
- Ask the same question to five people. You’ll hear five versions—and learn where the confusion lives.
- Start with a Big Dumb Question (BDQ). Make it normal (and safe) to ask the “dumb” thing before diving into the “smart” ones.
And most importantly, don’t wait for a crisis to start questioning. Do it when things seem fine. That’s when it matters most.
What If You’re Missing Something Right Now?
I’ve come to believe that everyone is missing something obvious, most of the time.
The difference is who’s willing to pause, get curious, and ask the unpolished question.
Not to prove how smart they are. But to help the team get somewhere better.
So here’s the question I’m sitting with this week:
What might I be missing… right now?