People Pleasing Case Study


People pleasers thrive on maintaining positive relationships, making everyone happy, and avoiding conflict. This will manifest itself differently for everyone, but in its most basic form people pleasers tend to tell everyone what they want to hear:

  • Classic “yes” person – this could include people who are strategic and innovative, but when the chips are down they never say no or “yes, but I have conditions” to anyone above them in the company. Then they will do whatever it takes to deliver the yes.
  • Mentoring – these people are the ultimate cheerleaders, pumping mentees full of career expectations that may be unrealistic
  • People management – these people convince everyone who works for them that they are one slight improvement away from the next promotion, even if the numbers game will not allow it

Impact if Unresolved

  • Burnout of themselves and their team– Because people pleasers want to please those above them, they will take on any monumental task and practically break themselves and their team achieving it, often working incredible hours. Once management becomes aware of this, they will lean on this team even harder, causing a snowball effect. Because the people pleaser is so well liked, the team will be supportive for a while, but then eventually burn out. This behavior can even lead to personal and health issues.  
  • Unrealistic expectations – People who have been mentored by people pleasers, often have unrealistic expectations of where their career should go and how fast. They trust the leader explicitly, so when they don’t meet those career expectations they get disenfranchised and leave the company.
  • Favoritism – Team members who do get promoted on this leader’s team become favorites and are “stars” that get good exposure, but eventually they burn out, too, and take a lateral move to a less taxing area. Team members who do not get promoted feel like they are chasing a moving target.Every year, they clear their last hurdle and because the leader does not have tough conversations with them, they also feel stuck and leave the company. The turnover is costly and requires training new people to the leader’s plate, having a snowball effect. 
  • Taken Advantage of – Peers eventually take advantage of the people pleaser’s desire to avoid conflict and will push their own agenda more and more. Rather than finding win/win opportunities, the people pleaser ends up losing out over time.

Options For Improvement

People pleasing is unlikely to be viewed as a problem as the individual works their way into management because they are so willing to take on work. Eventually, the desertion of good people from the area will become apparent. Self-help options or external training seminars about working smarter not harder will likely be of some technical help to this type of person. Also, people pleasers might find training regarding crucial conversations or negotiation. But the truth is, until they explore why they are people pleasers, learn to identify triggering situations, and give themselves permission to stop people pleasing, the behavior will persist. 


Coaching is a superior option for people pleasers because changing this pattern of behavior requires self-awareness about why they are so driven to please others. Coaching will also help them understand how constant people pleasing can damage the organization. 360° feedback that includes current and past direct reports is likely to highlight the shortcomings of the approach. During 1:1 conversations, a coach will skillfully help these leaders focus on their past and what drives them to please and what it feels like when they are entering “people pleasing mode.” Together they will partner on a development plan for how they can strategically say no. Shadow coaching will allow them to get feedback on their execution of the plan real time. The coach can be there to support them but also challenge them to focus on their own work-life balance and that of the people who report to them. 

My Personal Anecdote

We recently worked with Anna, the VP of a Fortune 500 company. Anna’s role in the organization includes a large scope. She has the reputation of being dependable, especially during difficult times. Anna is loved by almost everyone, but she was taking on so much work for her team and working so many hours herself that she was struggling to find fulfillment. She began having a variety of physical ailments but refused doctor’s orders and powered through them. Her marriage hit very rocky times because of her lack involvement at home. Some productive and vocal members of her team started to leave. This all led Anna to have an emotional breakdown in front of her boss. Suddenly, the person that exuded positivity and optimism cracked. Anna’s boss was participating in Executive Coaching and suggested that she do the same.

In the first coaching session with Anna, she described how overwhelmed she felt. Her role was impossible for any human being. The coach let her vent, but toward the end of the session asked her when the last time was that she said “no” at work. Anna gave some examples, but she agreed to reflect about the topic. Prior to the second session, the coach collected 360° feedback about Anna. It was clear that she was well liked, but that several current and former direct reports were upset about having to do work that wasn’t in their job description while working for Anna. 

During the 360° debrief, the coach returned to his initial question. This time, Anna recognized that her original answers were weak and explained that she doesn’t refuse any request to perform a meaningful amount of work. This allowed Anna to explore why she acted this way. What we found is that Anna had been bullied while she was growing up, and it left a lasting impact on her. She said yes to everything and worked hard to deliver because she wanted to feel accepted. We were then able to go back to all of the great things that people said about Anna in her 360° and come to the conclusion that Anna was already well regarded and accepted. This realization allowed Anna to let herself off the hook and determine that for the good of her people and her health, she would find ways to say no. We created a plan that Anna executed, and we discussed the results. By the end of the engagement, she had successfully figured out when and how to say no while being authentic to herself. At the end of the engagement, Anna exuded positivity about her work situation.