Part 2: The Pleaser Saboteur – Learning to Ask for What You Want
I first realized I had a problem with people-pleasing during a therapy session. I was stuck between two overbearing mothers—mine and my husband’s—both pulling in opposite directions over our holiday plans. The therapist’s question seemed simple: “What do you want to do for the holidays?” But I froze. My mind was blank.
As I dug through memories, I realized: there was no “I” allowed in my decision-making. Not in my family of origin. Not in my marriage. Not in my husband’s family. I had spent so long surviving by pleasing others that I had no idea what I wanted. Then I launched a tech startup…
Ha. Ha.
My experience of our 10-year tech startup was insane highs right next to the worst lows imaginable. Sometimes minutes apart. That’s the nature of any worthy creative pursuit—it’s hard, unpredictable, and will knock you down repeatedly. Guaranteed. With passion and drive, you’ll see it through.
Now, 16 years out from founding that company (and six years since it was acquired), I’ve realized that the hardest parts weren’t what I couldn’t control. It was the internal challenges that did the most damage. The real struggle was what my brain did when I felt overwhelmed or anxious. When stress hit (which was a constant), my brain defaulted to unhelpful patterns: trying to overachieve, impatient perfectionism, and pleasing others at the expense of myself. These behaviors, or “saboteurs,” would hijack my thinking, making everything harder than it needed to be.
In this second article of the series I’ll address how the Pleaser Saboteur gets in the way of creativity, teamwork and personal growth.
What is the Pleaser Saboteur?
Pleaser Saboteur works by1:
Indirectly seeking acceptance through rescuing, flattering, or over helping others.
Ignoring personal needs and becoming resentful over time.
Needing constant reassurance of others’ affection or approval.
Struggling to say “no”, establish healthy boundaries, or express one’s own needs clearly.
Becoming intrusive or overbearing in an anxiety-fueled effort to help.
Pleasing others often prevents us from recognizing and expressing our own needs. Over time, it can foster resentment, frustration, and disconnection—from both ourselves and the people we’re trying to please.
How Pleaser Hurts Teamwork
One of the biggest surprises having coached other entrepreneurs and executives who have Pleaser Saboteur is watching how Pleaser often hides who they really are. Though at the onset it looks selfless, what Pleaser does is disable people from learning they can be the driving force in their life and work.
Here are a few ways my Pleaser Saboteur impacted my relationships and work—along with what I know now:
I thought deferring to others made me likable and open-minded.
Now I know it meant avoiding responsibility for my own wants and ideas.
Now I ask: What do I want?
I thought that rescuing and fixing teammates was being a good collaborator.
Now I know that people need space to reflect, decide and grow on their own.
Now I ask: What’s mine to do, here? 2
I thought I was responsible for everyone’s emotions.
Now I know people’s feelings are theirs to manage, just as mine belong to me.
I thought I had to respond instantly and perfectly to every request (Pleaser + Hyper-Achiever + Stickler in action).
Now I know that time isn’t as scarce as it feels. I can reflect, and decide how I want to respond. can always say “no”, and “no” is often a “yes” to something greater.
I thought conflict was impossible to navigate.
Now I know that healthy conflict builds trust and strengthens teams.
Now I believe we can innovate win-win solutions if we stay curious.
The Trap of “Being Nice” at Work
I recently coached a creative team who were at an impasse. They were talented, kind, and deeply committed to their work. They were stuck because they didn’t have the tools to trust each other with disagreement. Each member defaulted to the Pleaser Saboteur, and got stuck in this mindset:
Either I’m nice (and swallow what I really think) or we won’t get this done
Either I agree or they won’t like me
Either we agree or it means we’re failing as a team
But creativity demands honesty. We can’t improve what we’re afraid to acknowledge. Faking “nice” hides the hard truths that need to come out. On the other hand, bluntness without empathy is just as harmful. Both extremes block the trust required for real collaboration and innovation.
Empathy and Curiosity: The Antidote to Pleaser Saboteur
Design Thinking taught me an essential lesson: conflict isn’t something to fear—it’s an opportunity multiplier. In Human-Centered Design, we start with research. This requires curiosity without judgment—looking at every part of the process, even the uncomfortable parts, with openness.
Magic happens when we do this:
We learn that others feel the same way we do.
Issues we’ve been avoiding suddenly seem more manageable.
We build empathy, opening the door to greater innovation.
We realize that a variety of perspectives is the team’s greatest asset.
The Positive Intelligence framework offers another powerful tool for conflict: “Find the 10%.” When conflict triggers your fight-or-flight response, try listening for the small part of the other person’s view you can agree with. Say, “What I like about that is…” and add your own idea. This “yes-and” approach, borrowed from improv, helps shift conversations from tension to collaboration. With practice, it’s possible to rewire your brain to respond this way automatically.
Closing Thoughts
The journey to overcome the Pleaser Saboteur is about unlearning habits that disconnect us from our true selves. Creativity and collaboration flourish not by avoiding conflict, but by approaching it with empathy and curiosity. This isn’t about perfection—it’s about progress. When we set boundaries, ask for what we need, and embrace healthy conflict, we unlock new possibilities in our work and relationships.
Call to Action
Where does the Pleaser Saboteur show up in your work or life? What would it feel like to ask for what you want? This week, try saying “no” to one request or letting a disagreement breathe without rushing to fix it. For deeper insights, explore the Positive Intelligence framework and see how it can transform your creativity and teamwork. Reach out for a free coaching introduction.
Stay tuned for the next article in this series, where we’ll dive into another saboteur that keeps us stuck—because mastering your mind is the key to unlocking your full potential.
References:
1: Chamine, Shirzad. Positive Intelligence: Why Only 20% of Teams and Individuals Achieve Their True Potential and How You Can Achieve Yours. Greenleaf Book Group Press, 2012.
2: Thanks, PQ coach Gale Thompson! It’s one of my favorite questions.
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