Why Executives from Large Companies Struggle in Small Businesses

Have you ever mistaken the “system of a large organization” for your “real personal capability”?

While reading “Say No’s Teachings”, I once again faced an uncomfortable truth.

Why do executives from large organizations sometimes collapse easily in small companies?
Through 20 years of experience in one industry, learning through real trial and error,
I want to share what I learned about the meaning of “real hands-on work.”

I. After Leaving a Mid-Sized Company and Starting in a New One

1️⃣ The Belief That “I Understand Real Work”

I have worked in the inkjet field for 20 years.
At my previous company, I joined at the launch of a new business and helped grow it to 9.7 billion KRW in revenue within five years.

Attending more than ten overseas exhibitions every year,
I could roughly judge competitors’ technology just by watching their print demonstrations.

“How far have they come?”
“How far do we need to go?”

Naturally, I believed I was an expert in this field.
And people around me treated me that way.

As I gained titles and responsibilities,
I learned what I should and shouldn’t say inside an organization.

Still, I believed I never lost my sense of practical understanding.

But looking back now,
what I called “practical work” was simply:
sales, strategy, and reporting.

I rarely touched machines directly.
I rarely tightened a single screw myself.

I think I simply believed that I understood real work.

2️⃣ The Meaning of “You Grew Up Too Comfortably”

In a newly started small organization,
I continued focusing on sales and strategy work.

Occasionally, I helped with machine testing.

As similar tests repeated,
I started feeling irritated inside.

“Why do I have to do this?”
“This used to be handled by the AS team at my previous company…”

Looking back now,
I was separating hands-on technical work from “my job.”

Then the ink supplier’s CEO visited.
He was a legend in the industry.
He personally disassembled equipment and tested everything more thoroughly than I did.

In the end, he found the root cause.

Then he looked at me and said quietly:

“You… seem to have grown up too comfortably.”