November 18

A cruel or ruthless supervisor – what do I do?



Why are you asking this question? Because you know what the answer would be.


Yet you’re not, or at least you’re still considering if you should.

Can I share my own story? Here goes.

In December 2020, a client complained about me. I won’t go into the specifics of the complaint. My boss launched a formal investigation. There was an independent investigator appointed.

I was suspended from working with this client.

My boss didn’t call me.

He didn’t speak to me about what would happen, or the process of what would be happening. Or why this was even happening. It felt like I was guilty of the charge, when the findings had yet to be published. There was little regard for what I had done for the client.

You can make your own conclusions about the kind of boss I had.

personal problems at work
Some bosses can be complete drains on your energy.

In this article, I want to share about the myths that we have when dealing with cruel or ruthless supervisors.

Your supervisor may be making you depressed. Lose your passion. Lose hope of the value within yourself. Desperate to quit the sector.

Why start with myths? Because without knowing the myths, the how-tos will never work. Because you’re going in with a certain mindset of what will work. Without addressing your mindset, you will never get into the right heart-set for change.

Then I want to share with you the mindset and strategies you can use in working with such supervisors. Of course, I’m making the assumption that despite knowing the benefits of leaving your organisation (and consequently your supervisor), you’re still deciding to stay.

Myth 1: I can change my supervisor or my organisation.

I confess. I was a small junior employee, at the lowest rung of the organisation. But I was oh so optimistic. I thought I could change the world!

That’s what university teaches, doesn’t it?

You have to be the change you want to see.

I sent out emails about how we could better transit into our next leadership. Or how we needed to change the culture of our organisation. This was me – a small fry, talking about things that were outside my pay scale! Was it really something I could talk about?

I didn’t care. I still did. You can see below for one example of how pompous I seemed.

A snapshot of what I wrote about our people possibility
A snapshot of what I wrote about our people possibility

Don’t try. If you try to change the character and personality of your organisation, it will be smashing your head against a brick wall.


I hesitate to say,

You won’t succeed.

Because there are times when you may succeed. But there are other times when you wouldn’t. But with a cruel or ruthless supervisor, the chances are even lower.

The biggest thing you can change is yourself.

Don’t try to change your boss.

Myth 2: I need to change myself.

3 months after the incident with the complaint, I had the chance to leave. There was a great job offer on the table. Why didn’t I leave? Because I felt that I needed to change. That it didn’t matter where I went, because I would take the same problems with me.

You may think that way too. You may think that the comments of your supervisor, however cruel they are, are true. You need to adjust them before you even think about leaving your organisation.

No. Take the example of my friend, Faith (not her real name). She’s been working in a food production company. Her supervisor has shouted at her, screamed at her, and scolded her for being lousy and incompetent. Even though her job is done by 5 (yes 5, you didn’t read that wrongly) at the parent company abroad. She’s come to internalise the comments that are said of her from her supervisor, believing them to be true.

I’m lousy.

I should be better. I need to improve.

Believing what the other party says of you, however cruel it sounds to a detached party, is a phenomenon in toxic relationships. Your identity is intertwined with that of your supervisor, because who are you without your supervisor? He may even trip you up, saying,

You would never be here if I didn’t give you this job.

You don’t deserve this job, but I gave you a chance.

You stay, because you think you need to change.

This was the mistake I made. I thought that the problems my supervisor had raised were repeating patterns, rather than problems that related with the misfit in culture.

If you’re not sure if you need to change, think of it this way. Even if you do, you will probably change more in an environment that encourages you to change.

Not an environment that scares you to change.

If your supervisor needs to resort to cruelty to convince you to change, forget it. You’re better off elsewhere.

Myth 3: I have no choice.

You may be staying with your cruel or ruthless supervisor because you think you don’t have a choice. You may have even internalised what your supervisor has said about you, thinking,

I’m so bad. No one will want me.

I don’t think I have the energy to look for another job. I’m burnt-out. I will struggle in another change.

You have a choice. Choosing to stay where you are now is also a choice.

cruel supervisor
Wherever you are, you always have a choice to choose happiness. Always.

What can you do?

Now that you know this, what can you do?

Here are 5 things you can try.

Draw clear boundaries

This is okay. This is not okay. That’s what boundaries are about.

In Henry Cloud and Townsend’s classic book ‘Boundaries’, they talk about how boundaries are like fences with gates in them. It’s not about being cruel to your already cruel supervisor. It’s about being clear.

It’s saying,

I wanted to let you know that I feel hurt whenever you shout at me.

This is not okay for me.

You may say,

John, my supervisor is already so mean… and you’re expecting me to say,


Are you crazy?

Nope I’m not. I thought so too. I used to deal with a cruel supervisor who shared my misdemeanours with anyone who would listen. He would complain to my boss. Or he would write an email to the entire team talking about my behavior.

It was shaming, to say the least.

I stopped talking to him. But I realised that didn’t solve the problem. One night, after receiving yet another instruction from him whereby he didn’t ask me about what I had done, I wrote an email to him to tell him about my feelings.

I placed my boundaries clearly. I was worried about how he would kill me for them.

But I thought to myself,

It’s already so bad! Nothing can make it worse. What’s the worst that could happen?

They could sack me?

Ah go on then.

But it worked!

It improved our relationships and helped us to clarify what was okay and not okay for us. We were clear about how to move forward in our relationships from there on.

Manage expectations by doing clear intakes

The reason your boss may be cruel or ruthless, may be because you haven’t met his expectations. Meeting expectations is important for any boss-employee relationship.

If you can do that, you can ensure that you make your boss happy. A happy boss isn’t that likely to be a ruthless and cruel boss.

But if your boss asks you to do something, you can’t say no, right?

You can say,



‘Yes and’ is a concept from improvisation, where you don’t give an outright ’No’. But you explore possibility with the use of ‘Yes and…’’

In his book, “The Art of Being Indispensable”, Bruce Tulgan talks about how we can improve the quality of the ask.

Clarify the ask by clarifying these four questions on hand (Credit: Bruce Tulgan, in The Art of Being Indispensable)
Clarify the ask by clarifying these four questions on hand (Credit: Bruce Tulgan, in The Art of Being Indispensable)

As social workers in a family service centre in Singapore, we were taught how to do the intake. An intake is to understand what the issues are, before deciding whether to take on the client as someone we would be asble to help.

Similarly, in your own tasks, every ask should have an intake memo. You should clarify the questions listed below so that you’re aware of whether it’s something you can or cannot do.

Possible questions you can ask in crafting your intake memo (Credit: Bruce Tulgan, in The Art of Being Indispensable)
Possible questions you can ask in crafting your intake memo (Credit: Bruce Tulgan, in The Art of Being Indispensable)

Clarify what done looks like

Brené Brown, in her book, “Dare to Lead”, talks about this concept of asking,

What does done look like?

Because all of us have different conceptions of what done kooks like. Your boss may scream at you because your ‘done’ looks horribly different from his ‘done’.

Therefore, clarifying what your boss needs you to do, and what the completed task would look like in his (not yours) eyes, will ensure that he’s not screaming at you any longer.

Ask for the help you need

Have you ever said to your boss,

I need…

If you haven’t, go and say it now.

Come on, we’re adults. If you don’t ask for what you want, and you quit without knowing whether your boss could ever be more respectful, you’re not giving yourself a chance.

Sometimes, we make the mistake of thinking that a job change will give us a better environment, without thinking about whether a difficult conversation can improve where you are.

There are ways to structure this conversation that will make it more productive. Some guidelines include:

  • use ‘I’ statements
    • doing this helps your boss to feel less accused or blamed for what has happened
  • talk about what you feel
    • use “I feel… whenever I am scolded ….”
    • when you do this, you start being able to talk about the impact of what your supervisor’s actions have done to you, without blaming the other party


If you’ve exhausted all the above options, explore the ‘quit’ button.

It’s a big red button. Think of it as a last-option.

Don’t resort to it as the first option.

A month ago, I quitted my job without any idea of where I would go. I had no job offer, and definitely no idea how long this period of unemployment would last. But I left, because I had come to the end of my tether. I had no idea where I was going, but worse still, I didn’t think I would continue to go anywhere with the organisation I was with. I was confident that going further with them would involve me deteriorating even further.

I left.

Having a cruel and ruthless supervisor can be the last straw to your job. When your job is already difficult, knowing that you have a poor supervisor who can support you through that process makes it more impossible.

Some things to note before you hit this button:

1. You don’t have to know where you’re going.

Don’t make it a must for you to have a job before you leave. You may not have one. That’s okay. Quitting can be the kick up the proverbial backside that galvanises you to get a job.

Fear keeps us stuck. If you continue to stick with your boss, you may not have the headspace to deal with a job change. You continue to stay on the vicious cycle, never leaving…

But never really there as well.

That’s even worse.

2. Build a kitty.

You don’t know how long you will be without your job. It’s best that you have some savings to tide you over. On a practical note, what helped me was having a steady stream of freelance assignments that gave me a few hundred dollars a month. Whilst not comparable to the salary I used to earn, it gave me the security and helped me to push past the anxiety of leaving without a job.


I’ve found the beauty of leaving a cruel and ruthless supervisor behind. It is my hope that you will, too.


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