Bosspleasing sucks

Gareth from “The Office” – one of the great bosspleasers of all time!

Gareth from “The Office” – one of the great bosspleasers of all time!

Today, I commence a trilogy of posts that talk about one of the most dangerous and hurtful behaviours that occurs in organisations.


This post will go into the causes and consequences of bosspleasing. The next two posts will focus on what to do about it.

First, lets talk about what bosspleasing is. Bosspleasing is behaviour that sees people:

  • only tell their leader or leaders doing or saying what they think that their boss wants (even when it’s not what they believe to be true);

  • and avoiding things that they think their leader or leaders don’t want (even when it’s not what they believe to be useful)

As with most behaviours that are harmful, it’s easy to talk about changing them and much more difficult to actually change the behaviour. Clever, committed and resilient people fall victim to this. At some stage, most of us have and will for various reasons. The purpose of this trilogy of posts is to draw your attention to bosspleasing so that you can become more aware of it and make some decisions about how you choose to act. Please keep that in mind as you read this – this post is about awareness rather than judgement of bosspleasing.

It hurts almost everyone involved in the process (assuming that their goal is to do better work) and happens for a few common reasons.

One major impact of bosspleasing is poor decision making. This is because decisions are made with incomplete or incorrect information. Yes, for many of us, we know that we need to make decisions and take actions when the information available is almost never complete or 100% correct. This makes it even worse! If leaders are making decisions with incorrect or incomplete pieces of incomplete or incorrect information, what chance do they have of making a good decision?

If you can imagine that you are doing a jigsaw puzzle and your aim is not to complete the jigsaw puzzle, but to accurately describe the picture in the jigsaw puzzle, this is what is happening in most organisations.

Now, imagine that you now have 25% less pieces. That makes things harder because there are more gaps.

To make it even harder, each of those pieces is missing 25%! This is getting ridiculous, right? Not only are there gaps, the pieces don’t connect and there is almost as much information not available to you as is available to you.

Welcome to bosspleasing. Bosspleasing sucks.

Bosspleasing’s impacts don’t stop here. It can also lead to over-dependence on leaders, a lack of diversity of thought in teams and organisations, low engagement levels, groupthink, a lack of innovation and ultimately, a culture of compliance over courage. All of these are huge costs to organisations in very real human and financial terms.

Bosspleasing sucks.

If it’s so bad, why does it happen? It happens because people think that they are doing the right thing.

They are protecting themselves, their team, their bosses or their organisation. People have a very sensitive radar for their own safety and will almost always act in their own interests. So, bosspleasing typically happens when there is a lack of psychological safety. Psychological safety is a term that became popular through Google’s research into what makes the most effective teams. Read more about it here. The key message is that if people are not feeling safe in their role, in their status and that it’s OK to make mistakes, they are going to do what they think that they need to in order to survive. Establishing and maintaining psychological safety in a team or organisation is hard work. It’s also the antidote to bosspleasing.

So, questions for you to consider are:

  1. Have you experienced bosspleasing – as boss and/or as pleaser?

  2. If you think it sucks, what are some things that might reduce bosspleasing?

  3. If you don’t think it sucks, what are the benefits that you see in it?

I’ll be sharing my thoughts on this over the next two weeks, so please feel free to get in touch. I’d love to hear your thoughts.

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