Why I Don't Always Win Well: My Struggle With Being a Pleaser

David Dye and I are on a mission to rid the world of soul-crushing leadership behaviors. I’m confident in our vision and our approach. I know it’s what I’ve been put on this planet to do, and that I’ve partnered with the right person to make it happen.

And yet, despite my passionate desire to make an impact, I sometimes let my own fears get in the way of asking for what I need.

When someone tells me our approach has turned their results around, or how our book was the first time they saw lightbulbs going off in someone they are mentoring, or when someone shares the impact our keynote speech or workshop made on their association or company, I get suddenly shy.  “Err… thank you.”

When what I should be saying is “Thank you! Can you please help us spread the word so we can make bigger impact? Who else needs this message? Would you help with an introduction? Would you mind saying that in an Amazon review? We’re taking Winning Well to Asia this Spring, do you know companies over there that could benefit from Winning Well?”

In this short video I share my reflections on my own Pleaser tendencies during a hike on Camelback mountain.

Are You a Pleaser Manager?

So far of the many people taking our Winning Well assessment, the most frequent profile is the “Pleaser” type by a landslide. Click here to complete this FREE self-assessment and receive your free profile and recommendations.

If you really want to breakthrough, to change the game, to make a difference, you’re going to need as much help as you can get. If you don’t ask for what you need, results suffer. There’s nothing humble about putting your needs last.  The real irony is, when your own fear or desire to please trumps your ability to ask for support, you put the mission in jeopardy– nothing confident or humble about that.