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Somehow I have always had “people pleaser” personality types in prominent places in my life. At the moment I would place three of my best friends in that category, two executives I am coaching, my foster son, and to some degree, my daughter. Yikes. What does that say about me? Another time….

In my younger years I eschewed people who got caught up into the various personality categories, finding they annoyingly went around defining people with those terms. You are an ENTP! You are an NF. You are a “driver”. It would often make others feel stupid if they didn’t have those categories on the top of their head. It was almost as annoying as those who would guess at people’s IQ.

Now that I’m older, and sometimes I really do feel old, I am continually struck by how much of life can be understood better with a handle on both personality influence and IQ ability. Perhaps it is most useful to the individual themselves, even more than for helping managers and relationships in general. Nonetheless, without grasping the tools such knowledge provides, people can be encouraged to do things that are almost impossible for them, while frighteningly easy for others. I am shocked by leaders and executives who have never applied this psychological “science” for the benefit of the business.

Some are sold on one particular personality categorizing system or another, but all of them provide some insights. They typically range from four to sixteen personality categories. My pondering has been on the one aptly called “people pleasers”. Somehow these people like me, yet that seems like the proverbial moth being drawn to the fire. They drive me nuts. I am tortured by watching their self destructive patterns that repeat and repeat and repeat. But, I like them. You like them. Everyone likes them, for a while anyway.

Are you a pleaser? How important is it to you that people approve of you? I know we all like to get approval and affirmation, but is it at the top of your list? Do you find that you will avoid dealing with issues that are bothering you because you don’t want to bother someone else or express disapproval? Will you end a relationship rather than deal with the conflicts inherent to it? Do you continue to choose short term peace over long term satisfaction?

The crazy thing about me is that I always believe that I can help the pleaser. I see how people are drawn to them. You want them at your party. They just make everyone feel good. I watch as others feel like they have found their best friend. Then I watch as the exuberance goes away quickly when they find the pleaser unreachable. The pleaser continually hears how others wish they were more available. Reality is that pleasers are forgiven for behavior that the rest of us would not be. Why? Because once you are with them, they are that pleasing!

One thing everyone should know about a pleaser is that down deep, they really don’t please themselves. Somewhere in time they came to believe that something about them was not good and this could be hidden from others if they learned to please well enough. Sure they may know that they are a good at some things, because they get a lot of affirmation, but in their own minds they realize that people just don’t see their fatal flaws. If others did, they would surely reject them… they are convinced.

Over the years I have come to realize that there are really only two things that can give the pleaser hope (avoiding the deep spiritual easy solutions here!). Those two things are: Truth and Short Term Pain.


Truth can be deeply uncomfortable. Expressing truth can be even more uncomfortable. Delaying and avoiding truth will be relationally destructive and damaging to both character and integrity. Unfortunately, these are all sentences that the pleaser doesn’t want to hear. If they really believed this, they would have to make some changes.

I happen to know something about truth from a very different perspective. My personality type drove me to care more about truth than pleasing to such a degree that I would run over people in the name of truth. Your friend may be fat or ugly or smell or be rude, but truth does not always need to be expressed. It took me a while to figure that out!

Any pleaser reading this is now trying not to laugh. They never would consider telling someone such things, even if they had to lie to avoid it. Unfortunately, sometimes we have to address issues about truth in order not to mislead or hurt a relationship. Do know however, there is a wide range of how truth can be expressed.

The real challenge for the pleaser is begin to grasp how much their lies and truth-avoidance has cost them in life. How many relationship have fallen at this alter? How many people cut off relationships with them because they don’t believe they are honest? How many good people in their lives got tired of feeling deceived? How much respect did they lose as they moved on to new relationships in order to avoid dealing with the tough issues?

Once the above is grasped, the pleaser won’t become a different personality type. They won’t suddenly become a bull in a china shop, but they can learn the skills of facing uncomfortable truth. Perhaps they will have to start with email rather than face to face confrontation. Maybe even a gentle text addressing something they would normally avoid. Truth telling can be learned behavior. Gracious and gentle truth telling can be something they model for the rest of us. Forget the all or nothing categories. Just make a 10% change!

Short Term Pain:

I know few people who ever read Scott Peck’s book “The Road Less Traveled” all the way through. I know many who quote the excruciatingly honest first sentence: “Life is difficult.” Since some call that profound, rather than obvious, let me try to be profound too. “The Road Less Travelled” basically says in 1000 ways: “Short term pain is worth long term gain.”

Consider the following by Peck: “The truth is that our finest moments are most likely to occur when we are feeling deeply uncomfortable, unhappy, or unfulfilled. For it is only in such moments, propelled by our discomfort, that we are likely to step out of our ruts and start searching for different ways or truer answers.”

In the business world, developing an operating plan is one of the great models of this. Walking people through that detailed process is excruciating. Many will push back and rebel. It is fun to remind them of this when they get their bonus checks or raises at the end of the year. Was it worth it? You bet.

The same is true when the pleaser fights through the short term discomfort of dealing with squirmy relational issues. It may not feel good in the short run, but often relationships are deepened and respect fills that hole that always had to be filled by pleasing before.

My hat is off to the pleasers in my life who have told me the truth when I didn’t want to hear it. I know how much it cost them, but they have my respect. Keep going! It is worth it. And reality is, I do need you!


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