I was Punished for Thinking Outside the Box

Donna (“Dee”) Wylie
4 min readJan 5, 2022
Treasure those unique people who can think outside the box.

Thinking outside the box is a common piece of advice from bosses to their employees. It’s one of those phrases that is bandied about without any thought of form or function. Employees are just supposed to know what you mean. If an employee encounters a difficult customer and isn’t sure what else to do besides the standard approach, their frustration id often countered with that old standby phrase, “think outside the box.”

I was always one of those people whose thought processes were a bit outside the box to begin with. As an aide in a pre-school class, I used to lead the children in make-believe activities like pretend snowball wars or dinosaur battles. I also addressed tiny frustrations with the invention of “tattle-time” — a daily tattle roundtable where neither the tattler or offender was ever reprimanded. I often led the children outside, under a walkway where echoes abounded, to scream for a count of 3. Not sure about the kids, but that sure released my anger and frustrations!

As an employee, my unique reasoning ability often got me promoted to management positions. My method of dealing with a perpetually tardy but otherwise great employee, was to simply schedule her half an hour before I needed her. Of course I didn’t tell her what I was doing. She arrived 15 minutes late for her shift, but 15 minutes early for when she was needed so we were both happy. And it meant neither one of us had to deal with those daily dreaded scolding’s. It also avoided the need to discipline her or fire someone whose work was otherwise outstanding.

However, at one job, my ability to think outside the box made my supervisor angry. To this day I still don’t understand why she couldn’t appreciate what I still think was a brilliant solution to a problem. Maybe you can explain it to me. Here’s what happened:

We were having a team meeting and my supervisor decided to do some sort of “team-building” exercise. We were divided into two groups of about six or seven employees and given a task. Fill a pair of pantyhose as quickly as possible. We were allowed to use anything we had — cell phones, notebooks, purses. The object was to just fill up the pantyhose and the winning team was promised a “wonderful reward.”

We all huddled to discuss what items we could use that were bulky enough to fill the pantyhose. And that’s when I suggested what I thought was a perfect, easy solution. My teammates unanimously agreed. So we formed a circle to hide what we were doing from the other team, and implemented my plan. A slender young lady slid the pantyhose on over her jeans, thus “filling” the hose in one quick move! I announced we were done!

The other team was shocked. They barely had one leg of their pantyhose filled. But they all laughed when they saw our solution. My boss, however, got angry! She was stunned speechless for a few moments, then she declared, “you Cheated!”

I responded, “how did we cheat? You said we could use Anything to fill the stockings. You Didn’t say we couldn’t use a person…” I was truly shocked. I thought my creativity would be applauded. I thought my boss would be pleased. Not angry. She just looked at me and repeated the damming phrase — “you cheated.” Then she ended the meeting and sent us all back to our seats. I felt disgraced. And we never did get our amazing prize.

So, before you tell employees to think outside the box, do some thinking of your own. Consider what that phrase means to you, and what your expectations are. Think also, about how you will respond when you get someone who thinks differently. Will you be able to accept that they may have a better solution? Will you be able to put aside your ego and utilize their unique abilities? Will you consider their suggestions in relation to how they can benefit your business? Or will you get angry and tell them “you cheated”? Your choice can mean the difference between a reluctant employee and an active, engaged team member. Choose wisely. Stop for a moment before you respond. Breathe, step outside your own box and — Think!

Donna Wylie is an author and co-founder of ChiWow Media LLC. She is always willing to offer suggestions on how to get your employees (and You!) to “think outside the box”. She can be reached at chiwowmedia@gmail.com

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Donna (“Dee”) Wylie

Donna (“Dee” to friends) Wylie is primary writer at ChiWow Media, and author of 9 books on Amazon, including her popular denture series, The 7 Stages of Teeth.