In the go-go days of the internet at the turn of the millennium, I worked for DoubleClick, a pioneering internet advertising company based in New York City. Fun, sometimes irreverent, and always entertaining, DoubleClick had many time-honored traditions.  But none was greater than the tradition surrounding Halloween.

On Halloween, every employee was encouraged to come to work in a costume.  All day, engineers, salespeople, admin support folks, and C-Suite executives would meet, transact and carry on business as if no one was wearing a pirate patch or an Austin Powers outfit.  At lunch, there was a huge parade, and one business unit was bestowed the honor of most creative themed costume.  It was always a difficult choice.

But the kicker to the Halloween madness was the one simple rule everyone had to follow: If you had a client-facing customer meeting that day, you were required to go in costume!  The customers loved it and it always made for some lighthearted moments.   On one such Halloween, I threw in a fake set of teeth, slapped on a bucket hat, put a glassy look in my eyes, and slipped into a gas station shirt.  Not sure what I was, exactly, but it checked the box and people seemed to enjoy it.  But after the parade, I suddenly remembered I had a 4pm customer meeting with a new prospect!  After some deliberation, I decided to honor the spirit of our Halloween mantra, and headed out to the prospect (along with a “Spider Man” clad sales engineer) in a fully ridiculous getup.

The meeting was located at the residence of the new prospect, who had not yet secured traditional office space.  And it was like nothing I had ever seen.  A New York apartment with 15-foot ceilings, three floors, a small lap pool, a spiral staircase , and a fully glass media room in the center of the first floor living area.  L-I-V-I-N!  We were greeted at the door by an assistant, who could not contain her laughter about our outfits.  This was gonna be fun!  

As we waited in the media room, we could see the prospect slowly descending the spiral staircase.  We couldn’t believe our eyes.  He had on a robe, an ascot, an Irish walking cap, and a “putting on the ritz” cane.  Clearly, we both thought, he knew about the DoubleClick tradition and was trying to beat us at our own game!  He burst into the media room with enthusiasm, looked me in the eyes, and shouted:

“Good show!  I absolutely love your costume!”

I did not hesitate and gave him an equally enthusiastic greeting:

“And I ABSOLUTELY love yours!”

At that point, the joy immediately drained from the prospect’s face.  He cleared his throat and feebly sat down in his chair.  There was about 10 seconds of silence as I listened to the buzzing from the overhead lights.  And then it hit me like a ton of bricks.

Oh My Horror!  He doesn’t know it’s Halloween.  This dude was NOT wearing a costume!

After what seemed an eternity, I clumsily started the presentation.  As I stammered through the delivery, the prospect stared blankly with his arms folded.  C’mon, buddy, what did you expect?  You’re wearing an ascot!

But rather than power through the awkwardness, or hold onto my righteous point of view, I shifted gears entirely. I stopped the presentation, shut off the projector, and looked directly at the prospect.

“Let’s start over.  Clearly, I misunderstood the situation and I certainly didn’t mean to offend you.  It was an honest mistake and I apologize.”

The prospect hesitated a beat and then broke into a grin.

“Well, I never thought about it, but I guess I do dress for Halloween every day.”

We both had a good laugh and the presentation went smoothly from there.  And couldn’t we all benefit by being a little more open and disarming in our everyday lives.

Take the First Step Forward

Sometimes, we open our mouths and inadvertently offend someone.  Sometimes, we take ourselves a little bit too seriously.  But both sides have to be wiling to work together to clear up any misunderstandings.  It’s hard to apologize when we feel as though we have done nothing wrong.  But being “right” and powering through with blinders does not serve anyone.  At the same time, sometimes we have to look at ourselves in the mirror before taking offense to a statement or action.  Perhaps there is a grain of truth in the “outrageous” statement.  Digging in and silently harboring resentment is not the recipe for a resilient life.

Conflict, whether in our work lives or personal lives, often stems from a basic misunderstanding.  Both sides may know the answer, but it takes a lot of courage to overtly address the source of the strife.  When someone takes that first step toward reconciliation, it often unravels the tension and leads to a breakthrough.

Our lives are hard enough.  We can’t let petty disagreements and unintentional gaffes derail our resilience.  We need to give each other a break.  We need to step back and not take ourselves so seriously.  And sometimes, we need to address the elephant in the room.  Even if that elephant is wearing an ascot!