CEO Failure Mode: Eeyore

The next in a potentially endless series on the pitfalls of the CEO role

A couple of years ago, my CEO-S cofounder, Sherif, brought me a stuffed Eeyore.

I laughed because I knew exactly what he was getting at. I’ve often admitted that I have Eeyore tendencies.

Over my career as CEO, if a salesperson told me about a great prospect, I would say, “Show me the order.”

If a salesperson showed me a great order, I would say, “Let's not celebrate until we get the check.”

When a check came in, I would say, “We knew that was coming. What does the pipeline for next month look like?”

I can trace my glass-half-empty outlook to my father. He was a very smart university professor and he expected his children to perform to very high standards. First was the only acceptable finish and all A's were the only acceptable grades. While this drove high performance, it also created a mindset where nothing was ever quite good enough.

The Eeyore CEO doesn't just see the glass as half empty. They assume it's going to spill, break, or be taken away entirely.

The Perils of Perpetual Pessi…