Whoops…I Just Pissed Off The Boss

Today I breakdown to you what to do if you did something that has really pissed off the boss. None of us purposely mean to do this, but it can happen.

I thought it was worth sharing a recent situation and how I chose to deal with it.

There are many different ways to approach the situation, but this is the path I chose and it may be applicable to you also.


I could just tell by the tone in his voice, HE WAS NOT HAPPY with me!

I had let him down, and the circumstances had amplified this.

I could just pretend it was a small glitch in our typically healthy relationship, but that is dangerous ground.


My boss is on holiday but felt compelled to dial into an important meeting on a matter where momentum needs to be maintained.

I had changed the meeting time to earlier in the day, and as a result the meeting was held without him. He texted me soon after asking “are we still on for 2pm?”

He rang me at 2pm saying “are we still on” to which I had to explain that the meeting was already held.

“What about my text, you did not reply?”

The question and tone in his voice said it all. He was pissed off with me. He was on holiday and had set aside a specific time to get involved. He did not want to be jerked around.

Now I’m not going to offer up weak excuses here, I let him down and I can understand his frustration with me.

This is (fortunately) a rare situation between him and I, so it has really put me on edge.

That’s the backstory. Now what?


I have to acknowledge that this is not just a small, trivial let down. There are deeper implications here.


I have disappointed him and I let him down. It will take more than one good deed to regain that trust.


I have lost credibility here. I now need to demonstrate over and above my normal track record that he can depend on me. I’ve got a lot of ground to make up and this will take consistency of application and output.


None of us are perfect and I am certainly no different. Some of us may be well-oiled workplace machines, and some of us are not.

I’m definitely not a dud, but I’m not a Ferrari either. Our CEO is the Ferrari, that’s why he is the CEO and I’m not.

I saw this quote in a recent article and it is worth sharing here.

The point is not to get better than others, it’s to get better than the old version of yourself.

That is my focus.


  1. Undertake some honest reflection, collect my thoughts and write them down.
  2. Talk it out with my boss when he get’s back from his holiday. I will do this on Day 1 of his return.
  3. Maintain the faith. I still believe I am a valuable contributor and asset to my employer so I can’t let this bring me down. If I lose my self belief at work, I lose my (work) identity. This could lead to an ugly downward spiral.
  4. Develop and execute my plan. I need to change something to claw back the trust and credibility. Just saying to him (or myself) “I’ll be better next time” is horseshit. I have some ideas on what I need to do and I will discuss these with him. I need his reality check and to be accountable not just to myself, but to him.
  5. Remain authentic. I am who I am. I can’t change who I am, I can only change my behaviour. Thus, I will focus on some specific behaviours that led to me pissing off my boss, but I won’t change me. I have plenty of redeeming features that are an advantage in the workplace so I will continue to leverage these.
  6. Continue to grow. As the saying goes “If you’re not growing you’re dying”. My spare time outside of work, family, friends and community is spent on this aspect. I read and I write a lot. Most, if not all of it is themed around self-leadership, workplace leadership, personal growth and happiness. I’m walking the right path, I just need to stay on it.

So wish me well as I commence my recovery journey with the boss.

Daniel T is the voice behind the blog Rockstar Leadership. If you want to be the best you can be at leading yourself and leading others, then click here to sign up and get your backstage pass to personal awesomeness.

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office workers all asleep in a meeting room

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A version of this article was originally posted on Medium