Five Most Embarrassing Moments Of My Career!

Rajasimha Karanam
6 min readSep 1, 2018

As managers, we feel pressurized to be at our best. We want to be the role models for our directs. Not just from a day-to-day execution of the business, but also from the personality and behavior – both inside and outside the workplace. But as every one else, we tend to run into embarrassing situations! When that happens, you are presented with two options! Sulk over it or laugh it off.

I too had many moments where I felt like kicking my back! Here are my top 5 from my professional career (so far).

#5 Tumbling, fumbling and mumbling

Long back, I was working for a start up. It was in the process of getting acquired by an US based MNC. We were all going through some anxious moments and the management felt it would good to organise a company outing to a resort, to cool the nerves.

Part of the program was a Town Hall. I was supposed to be one of the speakers (as I was helping with the technical side of acquisition). I was fully prepared to deliver my first speech on stage. In hindsight, I was probably a bit too confident of my stage performance.

When the actual time came, I just blacked out. In the excitement to reach the stage, I stepped on my colleagues’ feet. Almost tripped on the stairs. When I actually got on the stage, my throat completely dried up and my face was red. I completely forgot what I had to speak and cut a real terrible figure in front of my own team.

Instead of giving them the comfort of not to worry about the acquisition and that everything is going to be okay, I ended having them tell me not to worry about it and everything will be okay :)!

#4 A Formal Dinner In Pajamas!

I was working for a reputed Bank in Singapore. As part of expansion plans, I was made part of the team that flew down to Pune to help with the recruitment drive. After an exhaustive day of back-to-back interviews, we were asked to come down for dinner to debrief on the day long interviews and strategising for the next day.

It was a tiring day and wearing a formal dress with tie and blazer from morning till evening was quite choking. Without giving it much of a thought, I decided to change into a casual attire for the debriefing session and dinner. I didn’t feel the need to check with managers (my over-confidence at it again!). I went in pajamas and heavily printed t-shirt and slippers.

When I entered the dinner table, I was shocked to see all my colleagues, many of them who had even flew down from London & New York in perfect formals. Needless to say, I realised what a terrible situation I gotten myself into.

If not for my manager who put his arm around me and said “its perfectly alright”, I would not have had the courage to continue among them that evening.

#3 Singing was never my cup of tea, but drank it anyways

The stage fear is such a karma that it bites you in the most unexpected ways! I had joined back my previous company as a Director of Operations. Most of the team were my old colleagues who had witnessed my earlier on-stage bloopers (refer #5 above).

But from the time I had left and rejoined the company, it was a gap of 8 years and I was a changed person now (or so I thought). I had gotten better at public speaking (thanks to the various training programs I attended in the interim).

But when you had to get into an embarrassing moment, you loose all sane thinking.

There was a talent show event planned and I signed up to sing! I felt that I can pull it off with a bit of preparation and felt it was the best platform to experiment as the colleagues are well known (to take my on-stage histrionics again)! There was an inner voice that was constantly nudging me to back out even at the last minute before I started to climb up the stage! I did sing and it was so horrible that at the end of it, people started to pretend talking to each other rather than listening to me!

I ended up cutting yet another sorry face in front of the same colleagues and it was worse than ever before.

#2 Team dinner, traffic cops and expired documents

As part of the annual team event that year, we decided to go for a team dinner at an ultra posh restaurant.

Driving in Pune with a Karnataka registered vehicle was never a big deal. The cops were rather friendly and unless there was a traffic violation, you never get pulled over for a different state registration.

Until that unfortunate day, when I was driving to the annual team dinner with some of my directs. The traffic light was about to turn green, when we got pulled over for documents. I never paid road tax in Pune and my NOC had expired. We were getting late to the dinner and as my bad luck prevailed, the traffic cop was in no mood to let go. He threatened to seize the vehicle unless we pay the road tax and some hefty penalty.

I was supposed to be the role model for my team. I even prepared a “thank you and keep it going” speech for that evening. And there I was, trying to negotiate with the traffic cop for letting us go! I had to borrow money from my directs to pacify the cop and escape the bigger embarrassment of canceling the team dinner.

Though my team sympathised with me; "Is-this-the-kind-of-manager-we-are-reporting-into" expression was clearly evident on their faces.

#1 Being sober but still ramming the car into a deep pit!

This got to be the epic #1 embarrassment. It was gala dinner event again, it was Pune again. This time, the annual company outing was organised at Sentosa resort at Pune outskirts. Lots of drinks, loud music and free space to dance… The atmosphere inside the resort was super crazy, and equally crazy was the outside stretch which was dug up for some road maintenance works.

It was around midnight and after a thoroughly tiring evening at the resort, it was time to head home. I offered one of my colleague to drop him home. So, he and I sit in the car, take the car out of the resort and just while we are about to exit out, I ram the car straight into the pit that was dug up for maintenance.

The worst part of this incident was, I was the only guy who didn’t drink that evening. I was completely sober. But how do you make them believe, as I was the only guy who rammed his car after an alcohol filled evening!

The joke of that evening and the weeks, months and years to follow was that I don’t need to get drunk to ram my car into deep pits! My colleagues (managers and directs alike) had so much fun through out my tenure at that company that any new person joining my team would go through a mandatory orientation session by them not to drive along with me when I am sober!

I am sure each of you would have your own tales of embarrassing moments at work. My advice to you, especially when you are in a leadership role and carrying the weight of being perfect, is to live the moment. There is no better way to deal with the embarrassments than to just live it off and laugh it off.

Planning, preparation, situational awareness, having confidantes who can suggest you the right thing to do can all save you from getting into an embarrassing situation. But, being able to laugh at yourself is the greatest virtue that will come in handy when you are in the situation!

My sincere advice to all the budding managers is not to build boundaries around oneself (and act managerial). Rather, be the occasional subject of the team fun! Try it out & have fun!



Rajasimha Karanam

I like blogging about Indian Politics, Management and other interesting things in general. My political opinions are typically biased towards right of centre.