Are you a People Pleaser?

As women, we all tend to start this way; I don’t know many women who are not people pleasers or mind being disliked, after all, I think that everyone wants to be liked don’t they?

We all know that there are downsides to being a people pleaser but what about in a business sense?

I had someone who reported to me for several years, a real people pleaser; we will call her Anna. Anna was an excellent employee, nothing was too much trouble, she did everything that was asked of her, and she stayed as late as necessary so she could to get the job done. The flip side was this; when I gave Anna work to do that she didn’t understand, instead of coming and asking me about it, she missed her deadlines, when I gave her too much to do, she just stayed late, which impacted her family, but didn’t tell me about it, when I asked her to make decisions, she couldn’t do it, nervous that she was going to get it wrong and that I would be upset with her.

What was happening?

For a few months, I couldn’t understand what was happening, I had conversations that I thought were clear, we agreed on this stuff and walked away with clarity, and then something happened, and we were in a mess again. I changed how I asked, where I asked, the time I gave to Anna, I talked to her about trust and told her mistakes were fine, I asked for feedback and didn’t receive it, and I gave the feedback, and she took it on. Something was amiss. It was like Anna was too scared to provide me with the feedback or tell me what she really thought, but the times when she told me what she really thought, were the times when the project she was working on, or the task she was completing was so much better – and I wanted more of it.

I knew given the circumstances I had to tread carefully

Knowing that women are people pleasers, knowing that Anna came from a traditional background and that she was juggling a number of things in life, I decided to tread super carefully but I knew in order for Anna to reach her full potential and to unlock her blockages, I had to step up and do something differently. So, this is what I did and what happened:

Prepped for an awkward conversation

I thought about the things that had gone well and why I thought so, and all of the situations where it had felt like a miscommunication had happened, or a deadline had been missed.

Grouped the feedback into key themes

There is nothing worse than getting hit with 20 pieces of feedback when it can be summarised, and if Anna wanted examples, then I would have them on hand. 

Took the conversation away from the office (and went for a walk)

I didn’t want to have this conversation in an office; it was important to allow a good flow of dialogue to happen and enable her and I to be side by side as we chatted. I find that when you get out into nature and take away the “office vibe” that people open up and the conversation becomes more about feelings and less about the task, which is what I wanted.


I opened up the conversation about what I had noticed and what I was seeing and asked her to tell me what her experience was and what she thought of what I was seeing and noticing, Did she agree? Did she have an opinion? Did she disagree but wouldn’t tell me? Could this be fixed? How would we work together in the future?

Gave Anna the opportunity to open up

Anna told me about her experiences and why she did what she did (pure ah-ha moments for me), she shared her back story, her previous employee experiences within the government sector, which meant that she did not want to make a mistake, had to check things off numerous times to ensure they were right, didn’t want to say no for the notion that she look incompetent, and we also discussed the fact that I was task focussed (this is so true) and she needed me to be a little more “human” in my interactions with her. She also shared the fact that her hubby travelled a lot, which meant she was the primary carer for her children a lot of the time and while I was flexible, she felt guilty for putting her family first.

Agreed on the next steps

We decided that in our catch-ups, we would spend the start of it talking about the relationship and how it was going, what was happening at home and how she was feeling and then we would focus on the task. I was open to trying something else as was Anna. This worked really well for both of us (of course there were times when we would slip back into our default modes), but for the majority it worked, and the fact that we had had the conversation allowed us to use language that was our signal to each other if we were going off the rails.

You never know what someone is going through, even when you think you know them well, you work with them daily, things change don’t they?

Unless you are paying attention, you can miss the changes, and you can let tasks go because you don’t have the appropriate amount of time to deal with them there and then or you don’t want to have that awkward conversation. Earlier in my career, I would have shied away from the conversation, but I also know that when you shy away from it, the problem gets worse or the relationship turns sour, so I make every effort to have the awkward conversation nowadays.

What about you? Are there conversations you do not have that need to be had? Do you feel like you do these well?

I’m Emma, and I’m a business and executive coach who believes wholeheartedly in the potential of women. My coaching philosophy is simple- taking action leads to results- and I love working with women in business and in corporate roles to take their passion and drive and transform their professional and personal lives.

Be enthusiastic, optimistic and energetic, every day.

Em x

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Emma also has a podcast.