pleaser boss

Have you ever met a pleaser, or worked for one?

What is a pleaser?

A pleaser is someone who:

  1. Has a hard time saying no, so you can’t trust their yes.
  2. Will give and give instead of setting good boundaries.
  3. Will say “oh, sure, do what you want” and that’s not really expressing their preference. You have to read subtle signals to catch on to what they REALLY want.

First of all, I’ve worked for yellers, and it seems like working for a pleaser would be better. But it’s hard to work for a pleaser boss. They tell you things like, “I trust you. Just do what you do!” or, “I don’t really need to know what you’re doing, just let me know if I can get you anything.”

They may be uncomfortable with fundraising, or just not understand your job.

Or they may be afraid to actually tell you what they want.

Why would they be afraid of that? They may have unconscious concepts about money that include, “Money is evil” or “Money is mysterious” or “Money comes from parents (fundraiser stands in for parents), and I have to be careful not to piss off the fundraiser, because they will stop giving me money then.”

This person has internalized some key messages:

  1. Other people’s feelings are my responsibility.
  2. Other people’s feelings are my fault.
  3. If other people are upset, I am not safe, therefore…
  4. I have to try to control other people’s feelings, so I can be safe, and liked.
  5. It’s not safe for me to express my wants and needs, because that could make people feel bad. So I will just hint at them, and expect people to read my body language/subtle cues.

It’s hard to make any headway with your job, and get that promotion or a raise, when you’re just not sure what matters to your boss. This is why it frustrates folks to have a pleaser boss.

How do you connect with a pleaser boss and find out what they really want?

It’s not your job to play amateur psychologist with your boss. HOWEVER, you need to figure out what works, and uncover their true needs, wants, and feelings about how you are doing.

Living here, in the Pacific Northwest, people are much more passive-aggressive than the brash New York area where I’m from. I was laughing about this with a New York friend the other day. We both prefer up-front communication. But if you have to communicate with a pleaser, here’s how you can do it, to get to the heart of what they want, without trying to force it out of them.

10 Things to ask your pleaser boss to find out what they really want:

  1. Hey, I just took the StrengthsFinder and here are my strengths! What do you feel your strengths are? What do you feel your weaknesses are?
  2. What’s your feeling about money? Is it mysterious? Is it fun? Is it scary?
  3. What is your relationship to conflict?
  4. Here’s how I feel about conflict and my struggle with facing conflict. Here’s how I like to do it — how about you?
  5. How much of your job is currently major gifts, and how much would you like it be?
  6. What are your priorities right now? (Advocacy? Allocation of state funds? Collaboration? Maintaining but not expanding programs?)
  7. What are some difficult decisions that need to be made right now?
  8. What do you feel my priorities should be?
  9. What’s your communication style? How do you prefer to communicate?
  10. Here’s what I need: clear feedback, to be able to trust your yes and your no. Could you pause before saying yes, just so I know you’ve thought about it?

If you’ve ever worked for a pleaser, how did you make the most out of that dynamic? Let me know in the comments below!

Check out our State of the Nonprofit Workplace 2019 Infographic to see how the average nonprofit employee feels right now about the workplace culture, benefits, perks and other qualities they’re currently experiencing.

Mazarine Treyz
Mazarine Treyz is a nationally-recognized strategist for fundraising planning and communications. She is the CEO of Wild Woman Fundraising and the Author of The Wild Woman's Guide to Fundraising, as well as other books. Creator of over 12 e-courses, 3 masterclasses and 3 books, she has coached and taught over 12,000 nonprofit professionals how to be better fundraisers since 2010. Mazarine is the founder of the Fundraising Career Conference and the Nonprofit Leadership Summit.