CEO Chronicles 2: Horrible Bosses

Here’s the next installment in my guide to navigating your liferaft through today’s corporate rapids.

A horrible boss is a cross we have had to bear, at one time or the other, during our career. We must take a bad boss seriously. He or she can derail our career and our health. We need to find practical ways to mitigate the damage. There are don’ts and dos that can help us survive, and even thrive, in a toxic situation.

All of us will have surely come across one or more of these cries for help:

“How do you deal with a boss like mine? He micro-manages me to the point where I feel I need to ask him before going to the washroom!”

“She is always derogatory, and never lets up a chance to put me down!”

“He shamelessly takes credit for anything any of us do, and has no compunction in throwing us to the wolves when it suits him!”

“She leers at me every time I walk into his room. I am scared to even close the door!”

“He always favours his suck-ups!”

“How the heck did he even get to where he is? He must be someone’s brother-in-law!”

“We can leave. Or, we can learn”

At every stage in our career, we need a supervisor who supports, protects, encourages and motivates. Having a ‘bad’ boss is akin to suffering from an endless toothache, which flares up at regular intervals, but never subsides.

It can suck out joy from our life, make us feel undervalued, and push us to seek options under duress.

In a career spanning junior and middle management, we are likely to have between three to seven bosses on average. Sadly, we are as likely to have at least a couple who can make our life miserable at work.

What can we do when we have a boss who doesn’t inspire and support us?

We can leave. Or, we can learn.

I have worked with great bosses, good bosses and not-so-good bosses. When I look back on my career, I realise that some of my steepest learning arcs as a manager and a leader came about during my time with bosses I despised. Why? Two reasons :

First, from my perspective, it was simple. I was not well-off, I was not connected, I had a family. I did not have many options. I could not leave. So, I set about learning how to ‘manage upward’.

Second, I knew that, in a career spanning 25-30 years, I would encounter similar situations more than a few times. I decided that it would be better to learn how to handle these when I was junior and the stakes were smaller. I did not want to be in the C-suite facing an unpleasant board member and not knowing what to do.

Never give in to despair

So, let’s start with learning what we should not do. First, do not paint with a black brush.

No boss is completely bad. Each of us is an amalgam of good, bad and ugly characteristics and qualities. It is important that we understand and identify the specific issues that the boss does or says which causes pain or discomfort, and focus on dealing with them.

Second, do not paint yourself as a victim. It is easy, when in an unpleasant situation, to believe that the world is stacked against you. That is not the case. Look around and count all the things that are worthwhile. You will be surprised. And strengthened.

Third, do not give in to disillusionment. Never let anyone else’s behaviour change you. Don’t feel that your losing interest or under-performing is a valid response to a bad boss. Remember, you are a lamp, not a mirror.

Fourth, do not show fear. Or anger. Fear encourages bad behaviour. Bad bosses, like predators, can smell fear, and that only exacerbates their tendencies. Stand firm, keep cool. Blows outs are counterproductive. Remember, there is always a space between stimulus and response. Use the space wisely.

Lastly, do not assume, or accept hearsay. When a relationship is fraught, it is easy to assume the worst in every interaction. It is easy to believe a co-worker’s insidious gossip. Don’t succumb. Only accept and believe what you see and hear yourself. Make your own decisions, don’t be influenced or manipulated.

Avoiding these common behaviours will tilt the situation in our favour. We feel more in control. We feel calmer and less stressed. We find we can manoeuvre better.

This will prepare us for the steps laid out in the next article, where we will discuss different kinds of bosses and the strategies that we can use when dealing with each kind.

Till then, I would love to hear from you. Did what you read so far resonate with you? Do you have insights that I may have overlooked?

Your feedback, commentary and suggestions are not just welcome, they are requested and will be deeply appreciated.

Venkatraman Sheshashayee

Venkatraman Sheshashayee (Shesh) is Managing Director of Radical Advice, a business transformation advisory based in Singapore. He has over 34 years of experience in manufacturing, shipping and offshore oil & gas. Shesh’s previous roles include CEO of Miclyn Express Offshore, CEO & ED of Jaya Holdings Limited and Managing Director of Greatship Global. In his new avatar, Shesh helps SMEs, start-ups and aspiring professionals achieve their potential.


  1. Quite constructive and productive suggestions for how not to give in to despair. What do you think about speaking frankly with this person. Not confrontational but letting them know the relationship is counterproductive and clearly pointing out behaviours you don’t appreciate, while also taking responsibility for anything you need to. Just basically putting everything in the open? Would that help with the Fourth suggestion about not showing fear?

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