From Insight to Oversight: Blinded by Experience

Watercolor of a diverse team questioning a strategy presentation in a meeting room.

What You’ll Learn From Emily’s Story

  • How past success can make leaders overlook new market signals
  • Why challenging assumptions early helps prevent blind spots
  • How tools like “red teams” and pre-mortems can turn experience into a strength, not a weakness

Experience is powerful—but paired with humility and open questioning, it becomes a tool for clarity, not bias.

When Experience Becomes a Blind Spot: Catching Bias in Business Decisions

Emily had always trusted her instincts. As Head of Strategy at IronSprout AgriCo in Redfield, Iowa, she’d spent over a decade making well-timed, smart calls in the grain markets.

Her confidence—and growing reputation—came largely from her success with corn. She’d steered the company through several volatile seasons and helped them come out ahead, even when others faltered.

At IronSprout, the harvest season buzz was in full swing. Spreadsheets filled the desks, coffee cups clattered, and the faint scent of grain dust drifted through the air.

 

The Warning Signs Were There

When the 2025 market reports hit Emily’s desk, they showed a spike in global demand for soy. She barely skimmed the numbers before pushing forward with her plan.

IronSprout had just finished its most profitable corn season in five years. Weather forecasts promised another strong harvest. Emily didn’t hesitate.

“Corn has always pulled through for us,” she told her team during the monthly strategy session. “We’ve survived three market swings by staying the course.”

Around the table, a few junior analysts shifted in their seats. Jenny, fresh out of grad school, had spent weeks analyzing futures and flagged early signs of corn oversupply.

Paul, from the international trade team, had picked up on growing soy demand—especially from Southeast Asia.

They backed their concerns with data, charts, and projections. But Emily waved them off.

“I get it, but experience tells me corn is still our safest play. We’ve built our name on it. I’m not changing direction over a few new numbers.”

No one pushed back. At IronSprout, like at many firms, senior leaders rarely got challenged. And Emily’s record made her word carry weight.

 

When Reality Hits

As fall turned to winter, the shift in the market unfolded just as Jenny and Paul had warned.

IronSprout’s biggest client, Heartland Grains Inc., called during their quarterly check-in. The news came fast.

They were moving away from corn. Consumer demand for plant-based foods was rising fast, and soy was the new focus.

“We’ve valued this partnership,” the buyer said. “But soy demand is up 40%. We need suppliers who can deliver.”

The loss wasn’t fatal, but it was serious—25% of IronSprout’s revenue gone overnight. An emergency board meeting was called.

The message was clear: they’d missed a major trend that competitors had already moved on.

 

The Moment of Recognition

That night, Emily sat alone in her office, staring at the reports she’d brushed aside.

The data had been clear. Market trends, shifting demand, global trade shifts—it had all been there. But she hadn’t seen it.

She realized her success with corn had become a filter. Anything that didn’t fit her winning formula was ignored or explained away.

“I Fell Into the Trap of Confirmation Bias.”

She later admitted this to her mentor, Robert, who’d recently retired. “I was so focused on proving I was right, I stopped listening to anything that said otherwise.”

 

Building Systems That Challenge Assumptions

Emily didn’t want this to happen again. So she made a bold change to IronSprout’s planning process.

She introduced a “red team”—a rotating group from across departments tasked with one job: challenge the strategy.

Their goal wasn’t to be difficult. It was to poke holes in ideas, find risks, and bring blind spots to light before they cause problems.

She brought in junior analysts, seasoned traders, even admin staff. Each offered a different lens.

“I Want You to Poke Holes in Every Plan.”

That’s what she told the red team during their first meeting.

“You’re not here to agree with me. You’re here to help us spot what we’re missing—before it costs us.”

 

Culture Change in Action

The shift wasn’t overnight, but it took hold.

In time, IronSprout’s meetings changed. No longer was Emily’s word final. Her proposals sparked questions, pushback, and new ideas.

Paul, once dismissed for his soy data, led a new task force on emerging markets. Jenny’s forecasting models became key to every strategy meeting. New hires spoke up freely.

Bias showed up in other areas once the red team took a closer look. One review found they were sticking with outdated vendors even when better options existed. Another uncovered faulty assumptions about customer preferences that hadn’t been tested in years.

 

Measuring Success

A year after the change, the results were clear:

  • Soy was now 35% of IronSprout’s crop focus
  • Forecast accuracy jumped 28%
  • Two new contracts were secured with major soy buyers

More importantly, the company became quicker, smarter, and more adaptable. Challenging assumptions had become part of the culture.

Emily’s mistake had turned into a transformation.

 

The Broader Impact

Today, when Emily speaks at industry events, she tells this story.

“Experience is priceless,” she says. “But the moment we stop questioning it, we start making mistakes we could have avoided.”

Other companies took notice. Red team practices spread through the network. What started as a gut decision gone wrong became a movement toward better thinking.

 

For Leaders and Business Owners

Emily’s story holds lessons for any leader facing tough decisions. Before making your next big call, ask yourself:

  • When was the last time I looked for evidence that challenges my plan?
  • Who on my team might see something I’m missing?
  • How do I make sure every voice gets heard?

The Most Dangerous Bias Isn’t the One We Know About—It’s the One We Don’t See Because We’re Too Confident in Ourselves.

 

Lesson Insights

Experience is only helpful when it’s paired with curiosity and humility.

Emily’s story shows a common trap: relying too much on what worked in the past. She wasn’t lazy or incompetent—she was caught in confirmation bias.

The takeaway:

Experience becomes a problem when it drowns out new ideas or ignores fresh data.

Strong leaders don’t just follow their track record. They stay open, invite pushback, and keep adapting.

Emily went from “sure she was right” to “eager to be wrong—if it meant better outcomes.” Her shift made her a better strategist and a stronger leader.

In fast-moving industries, the ability to unlearn may matter more than how much you already know.

Practical Moves to Catch Bias Early

Want to avoid falling into the same trap?

Try this:

  • Create a challenge culture
     Build red team-style processes that make questioning the norm, not the exception.
  • Separate data from ego
     Ask: “Would I trust this data if it disagreed with my plan?”
  • Invite different perspectives
     Junior staff, new hires, and other departments may see things you can’t.
  • Use pre-mortems
     Ask: “If this plan fails, what would have caused it?” Do this before launching.
  • Rethink old habits regularly
     Just because something worked before doesn’t mean it still does.

Watch for These Red Flags

Bias is sneaky. These signs mean it might be clouding your judgment:

  • You rely on the same playbook, no matter what’s changing around you
  • You dismiss input from junior or dissenting voices—even when they have data
  • You call ideas “risky” without digging into them
  • You trust what’s always worked without reevaluating it
  • You’re emotionally tied to past wins, especially under stress

Spot these? It’s time to pause and reassess.

From Insight to Action: Ask Yourself

Great leaders aren’t defined by experience—they’re defined by their willingness to learn.

  • When did I last invite someone to disagree with me?
  • Which “facts” do I treat as gospel—but haven’t tested in a while?
  • Who am I not hearing from—and why?
  • Do I have systems in place to catch blind spots?
  • Am I rewarding insight and truth—or just agreement?

Conclusion

Emily’s story isn’t just about a mistake—it’s about growth.

She shifted from instinct-driven decisions to a culture where questions were welcome. That’s real leadership.

In a world that moves fast, the leaders who thrive won’t be the ones who think they’re always right. They’ll be the ones who question, listen, and adjust.

Because experience is a gift—but only if you’re willing to challenge it.