Escaping people-pleasing: Transforming into an assertive and effective leader

People-pleasing will keep you busy and make you feel important, but it will get in your way of becoming an effective leader. In this article, transformational leadership coach Jeanette Mundy addresses two key qualities that potential leaders need to develop to go beyond people-pleasing and step into being the leader they can be: authenticity and assertiveness.

This post was originally published on Engenisis.

People-pleasing involves putting someone else’s needs before our own. A people-pleaser’s common observable behaviours are a tendency to be overly agreeable, helpful, kind and self-sacrificing. They can also be guilty of self-neglect. What they get from people-pleasing is validation and approval that they are useful and important. They have an underlying desire to establish their sense of self-worth, making them feel needed and giving them meaning and purpose. You may know someone who fits this description. Or perhaps you resonate with it yourself.

On the surface, people-pleasing behaviours might seem positive and even admirable. However, when those behaviours are manifested purely for the sake of pleasing others, they come at a cost for a potential leader. Why? Because a leader needs to build relationships and be present so they can effectively interact and collaborate with the people they lead. Sometimes this involves having difficult conversations around making and managing requests and ensuring people are held accountable for their promises and commitments.

People-pleasing can become a behavioural pattern that makes us feel validated for who we are and our capabilities. It makes us feel important and worthy. However, while people-pleasing can feel like an act of kindness, it is a symptom of self-doubt and not knowing who we truly are at our essence. Ultimately, it is a behaviour that prevents us from allowing our leadership greatness to shine. That’s because if we’re people-pleasing to seek validation and boost our confidence, we are unlikely to have effective conversations and build strong relationships and partnerships, both critical to becoming an effective leader.

People-pleasing impacts our self-worth because it causes us to seek validation externally rather than validating ourselves from the inside. Needing validation from others can stem from dominant narratives such as: ‘I’m only worthy because you say I am’, ‘I don’t know who I am without your validation’ and ‘when you validate me, I feel better about myself’. The question is, where are the people-pleasing behaviours rooted, and how can we reduce or eliminate them? 

A client case study

One of my group program participants shared that she’d been asked to take on a role in a not-for-profit organisation. The organisation was planning a large event to raise money to support women who had left domestic violence relationships, and my client was tasked with helping to organise and run the event with two others. Initially, my client was thrilled to participate in an event to raise funds for a cause she cared deeply about, as she had left a domestic violence relationship herself. However, her enthusiasm proved to be short-lived.   

During a coaching session, my client shared that she felt pushed around and overloaded with administrative tasks. She said she was starting each day feeling overwhelmed as she juggled running her empowerment coaching business with her role at the not-for-profit organisation. As a result, building her business was becoming increasingly difficult. She wanted to know how to ‘deal’ with this. What we uncovered during our first conversation was her pattern of people-pleasing that resulted in her jumping into the new role with very little clarity around what it would involve. She quickly discovered it entailed poorly worded requests and multiple demands. However, as a people-pleaser, she didn’t consider seeking clarification and requesting clear boundaries and commitments. 

It quickly became evident that rarely asking for clarification and not giving herself time to consider and respond to requests were habitual behaviours. Furthermore, deep down, it seemed my client didn’t believe she had the right to make requests such as establishing mechanisms for support, chains of communication and clarification of expectations. Taking a back seat to satisfy the needs of others left her feeling shocked and confused. Others in the organising committee had abused their power to delegate all the administrative tasks to her, and she wasn’t assertive enough to seek clarity or say no. 

When my client accepted the role she thought she would be given the opportunity to unleash her potential as a leader. It wasn’t until a couple of weeks later, when she felt the tasks were demanding too much of her time, that she realised she’d accepted the role too quickly, without considering what it would involve. During our first coaching session, she began to see her old pattern of people-pleasing had resurfaced because she just wanted to be needed. Her higher purpose was to be an empowerment coach who specifically supported women who had left domestic violence relationships. Administrative tasks would not support that dream.

In my coaching experience, I’ve found that no behaviour is best managed by trying to focus on changing the behaviour alone. That’s because every behaviour is rooted in deeper issues that can be more directly addressed. These deeper issues involve looking at how a person is being. Let’s explore two of these underlying qualities – or ways of Being – and how they play a key role in preventing people-pleasing behaviour: authenticity and assertiveness.


According to Ashkan Tashvir, author of BEING, and creator of the Being Framework, ‘authenticity is being consistent with who you say you are for others, and who you say you are for yourself. Authenticity is both being yourself and being with your Self. It is the congruence of your self-image – who you know yourself to be – and your persona – who you choose to project to others’.

Because people-pleasing behaviours are deep-seated and stem from self-belief and the need to please, it was important to look at my client’s persona (the conversations she had with the world about herself) and self-image (the conversations she had with herself about herself).  

From these perspectives, we were able to address the deeper drivers that were resulting in her people-pleasing patterns:

  • How she often felt unworthy,
  • Her dominant narrative of having to be nice, agreeable, helpful and kind, and why she felt awkward about spinning this into a more empowering narrative, 
  • Who she believed herself to be and why her current identity was tied to being a people-pleaser, and
  • How being a people-pleaser prevented her from being the authentic unique leader she had the potential to be.  


Once we examined the underlying drivers of my client’s behaviour, we could begin to work on her assertiveness, which would enable her to stand up for her point of view whilst also being respectful of others. The outcome was that she became resolute, straight and firm in expressing her thoughts and feelings – all qualities possessed by effective leaders leaders. Being assertive supported her in requesting clarity, putting clear boundaries in place and ensuring commitments were clearly articulated and agreed to. It also gave her the courage to ask to be considered for a leadership role at the organisation. Furthermore, she learned that she doesn’t always have to say yes. She could decline a request, take some time to consider it or even make a counter offer. 

Being assertive was very empowering for my client. Over time, she became more aligned with her authentic self, which enabled her to be the leader she had the potential to be. Instead of thinking of herself as an empowerment coach somewhere in the future, she moved on from the not-for-profit organisation and became the empowerment coach she desired to be, who now makes a significant contribution to others.   

People-pleasing has the potential to get in the way of expressing who you are at your essence – your Unique Being. It stops you from thriving, having self-agency over your decisions and your life, and finally stepping up to be the leader you know you can be. If you’re seeking clarification on how you can become the leader you can be and what it will take to drop your people-pleasing behaviours, please reach out to me so we can have a conversation.

About the Author

Jeanette Mundy

Jeanette is a transformational leadership coach, with 35 years of business, training, and leadership experience, who supports people to unleash their potential and develop their business as a self-expression of who they are and what they care about. She sees many leaders with unique skills and untapped potential who question their ability to lead. Many who operate out of the fear and judgement that who they are isn’t enough, and that what they do won’t be good enough. Jeanette believes that when leaders look to what is within them they can discover potential and uniqueness that was masked by their doubts, changing the conversation they have about themselves from “I’m not enough” to “I am enough”. As a result, Jeanette’s clients trust their decisions and powerfully choose their path forward.

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