The Risks of Working for a People-Pleasing Leader

  • 8 mins read

Working for someone who is a people-pleaser may seem fairly innocuous or even desirable, but such leaders pose daunting challenges for their organizations. If you work for a people-pleaser, you most likely see the inherent problems and confess to seeking ways to maneuver around them.
People-pleasing leaders have some beneficial traits, but their behaviors can threaten survival in todays highly competitive and responsive business climate: indecisiveness, lack of direction, inability to retain adequate personnel, low accountability and overall inefficiency.
People-pleasers have an excessive compulsion to be liked and appear likable. This tendency impedes their ability to influence results. Leadership coaching can help them learn several helpful approaches to combating the problem.
Are You a People-Pleaser?
People-pleasers focus on others reactions and are highly interested in building positive relationships and managing impressions and interactions.
They want to be liked by as many people as possible to meet their psychological needs and achieve success, according to Dr. Beatrice Chestnut, author of The 9 Types of Leadership: Mastering the Art of People in the 21st Century Workplace (Post Hill Press, 2017). People-pleasers endear themselves to others through three seemingly helpful communication tools: flattery, warmth and positivity.
People-pleasers need to be liked often seems dire and, as with most personality traits, is heavily influenced by childhood factors. Insecurities or fears manifest themselves in a variety of behaviors that are rarely acknowledged. When they please people around them, they feel a sense of well-being, Dr. Chestnut explains. This is both comforting and affirming, and pleasers hope its enough to bypass any potential rejection. By complimenting others, people-pleasers try to win over others by discerning what they want and giving it to them.
The Good, Bad, and the Ugly
Even though people-pleasers view their world through this warped lens, some positive behaviors often emerge. People-pleasing leaders:

  • Value people, are great advocates and facilitate connections
  • Serve selflessly, with a positive and inspiring approach
  • Value strengths and talents
  • Understand others feelings and needs

But there are many negative aspects, as well. People-pleasers:

  • Wear themselves out trying to please everyone
  • Take on tasks they could easily assign
  • Avoid taking charge and have difficulty making decisions
  • Sugarcoat responses and resist honest feedback
  • Portray a false image of friendliness
  • Overlook their own plans, feelings, and needs
  • Tolerate bad performance or behavior
  • Become resentful when things dont play out in their favor
  • Manipulate people to avoid asking for what they want

Its easy to imagine the organizational crises that can result from these leadership shortcomings.
A Personality Style
People-pleasers can be identified by some basic outward behaviors, none of which are alarming in and of themselves. But combine these behaviors, and youll find a leader whos likely to be a source of problems.
The people-pleasing personality is, in fact, a distinct leadership type, according to Dr. Chestnut. HR personnel and leadership coaches are trained to assess them and appropriately deal with the problems that arise with this leadership style.
This type of leader is exceedingly (perhaps unnecessarily) nice and relationally focused. They listen well and offer emotional support. They are recharged when harmony increases and drained when discord breaks out. Their feelings may be hurt when unity is disrupted. They are more drawn to the yes people than to those who challenge or raise opposing viewpoints.
Leaders who want to be liked have a hard time asking for help or assigning work. Pleasers are outwardly bothered by those who fail to reciprocate with relationship-building, unity, or harmony. They are visibly disturbed by people who dont share their priority of being considerate to others.
Leaders with these traits will also display resentment over being left out, having their suggestions ignored, and being taken advantage of for their generosity. We may hear them venting their frustrations, but never directly to the person who displeased them.
When we see these behaviors on a consistent basis, it means were most likely dealing with a people-pleaser.
Inner Workings
Understanding what goes on inside people-pleasers heads can help us work with them.
People-pleasing leaders are most comfortable when they receive approval, consensus, and mutual consideration. This makes them relationally productive, yet corporately productive only at the peak of harmony. They empathize well and feel the need to serve selflessly. They see the good in others and give them the benefit of the doubt.
Avoiding rejection is paramount to them, so they hide emotions that may upset others and suppress contrary opinions. This explains why they serve others with the hope that theyll be served in return, without having to ask other people to do so. They become adept at reading others body language and are sensitive to others moods and preferences, allowing them to shapeshift to the most effective position to win people over.
People-pleasing leaders can strategize impression management to look good, receive affirmation and be liked. Being upbeat is important to them. They generally have the skills to lift peoples spirits and focus on meeting the needs of those who work for them. They may resort to manipulation as a means to a desired end.
Pleasers also develop blind spots that prevent them from seeing their own needs going unmet. They cannot recognize their own neediness, resentment, desire to blame others for ruined plans and loneliness, even while theyre surrounded by friends. They repress frustration over the lack of social reciprocity or co-unity. This can, in the extreme, impair their perceptions, cloud judgment, and lead to poor decisions.
Blind Spots
Its difficult to deal with people-pleasing leaders who cannot see whats obvious to others. Colleagues and coaches can help guide them by asking several key questions:

  • Do you find it hard to say no to people?
  • Is it difficult to ask people to help you or take on a tough assignment?
  • Is being liked one of the most important things to you? Why?
  • Is cultivating positive relationships the most vital part of your job?
  • Do you struggle to meet everyones needs all the time?
  • Does positive feedback give you an incredible high? What about criticism?
  • What gives you the most emotional reassurance on the job?
  • How do you feel when you upset or disappoint someone?
  • What happens inside you when conflict arises?
  • How do you handle difficult performance discussions with subordinates?
  • Do you criticize yourself when rejected?
  • Do your own needs go unmet? Why?
  • Do you paint a positive picture for people, even when its not that encouraging?

Truthful answers to these questions can help people-pleasers see how their behavior negatively impacts their personal and professional lives.
Suggested Steps for People-Pleasers
It may be a struggle for people-pleasing leaders to identify their traits, so its important for seasoned colleagues or a leadership coach to employ tested approaches when working with them. The process begins with encouraging pleasers to step outside their comfort zones and establish healthy boundaries. Theyll need to observe their emotions and responses to uncomfortable situations and learn to grow more comfortable.
The following steps can help them improve self-awareness and build confidence:

  • Grasp what triggers undesirable reactions. What kind of reactions would better serve you?
  • Embrace each emotion and process it. Find a way to moderate reactions.
  • Make note of the benefits when you break old habits and adopt new ones.

People-pleasers need new guidelines and/or boundaries. They must learn that setting expectations and making requests of others are positive leadership behaviors. People are not as fickle as they may think. Leaders can learn to give critical, yet constructive, feedback, knowing it benefits everyone.
Pleasers should copy the following behavioral cheat sheet to their smartphones and tablets so its always within reach:

  • Its normal and healthy to say no.
  • Youre not responsible for how others feel. You can control only how you feel. Leaders cannot regulate their staffs happiness. People have their own issues, so be clear about boundaries.
  • Affirmation and confidence come from within, not from others.
  • Act from the heart, not from a strategy. Staged behavior is obvious and detrimental.
  • Make sure your own needs are addressed instead of playing the martyr.

Working for a People Pleaser
People-pleasing leaders can benefit greatly from their staffs supportive gestures and understanding. Show appreciation when pleasers share their feelings or try to be transparent. Commend them on decisiveness and setting direction. Provide safe but meaningful feedback, mixed with praise whenever possible.
We can help people-pleasing leaders through dedication, teamwork and being reliable partnerssteps we should take anyway. We can encourage delegating by suggesting action items or taking on tasks that need to get done.
As leaders leave behind their people-pleasing ways, everyone will see the improvements in organizational culture: productivity, direction, accountability, morale, team strength and true unity.

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