The Boss Who Just Can’t Say No

by Joan Garry

If your boss has the “curse of the pleaser” this post is for you. Your boss won’t push back when those in power make crazy requests. And you bear the brunt.

While I usually write from the perspective of the nonprofit leader, this week I’m writing from the point of view of the staff. I hope to open the eyes of leaders who are stricken with a particular (but very common) malady.

You see your boss coming down the hall. He’s looking enthusiastic. But is that a touch of guilt you detect in his face?

He stops at your desk and says, “So I just met with Joan Anderson…”

You immediately break out in a sweat.

Joan, you see, is a long time donor. And every time she speaks to your boss, all of a sudden your workload doubles. When it comes to Joan, your boss just can’t say no. And somehow, the staff ends up getting the brunt of it. Every. Single. Time.

“I’ve been trying to secure a big upgrade from Joan and she has a great idea she’d like to fund.”

This is even worse than normal. You cringe. On top of your regular ridiculous workload, one of your key staff people just took a new job she couldn’t refuse so you already have more to do than normal. Guess you’ll be selling those concert tickets you had on StubHub. You certainly won’t have time to go.

Your boss has “the curse of the pleaser.”

And he does it all the time – not just for funders like Joan who want to underwrite new programs.

When your board chair demands a “very simple” report for a meeting and needs it in the next 48 hours (and the report is not remotely simple) your boss says, “OK.”

When your lead funder pushes you to focus on her latest priority, even if means dropping the ball on previously established milestones, your boss says, “No problem.”

And you want to pull your hair out.

Because you understand the consequences. And because you’re the one who’s going to have to skip your kid’s soccer game to get all this work done.

The curse of the pleaser.

Today, I want to help you overcome this common malady.

What do you do with the boss who can’t say no?


Here’s what you want to say when you’re boss can’t say no…

  1. You want me to do more with less? You’re nuts, right?
  2. Can you just stay in your office and not talk to anyone with power? Like ever?
  3. No worries boss, I’ll just assign that brand new program to THE STAFF MEMBER YOU CUT FROM MY BUDGET!
  4. Our organization needs better health coverage for therapy. For YOU!

Why is this so frustrating? It’s not that you don’t want to work hard. It’s just that it seems like the staff always gets the short end of the stick. While your boss may have the curse of the pleaser, somehow he never seems to care very much about pleasing the people who actually do the work. Or even if he does express sympathy, he never protects the staff by pushing back.


Phew! With that out of the way, it’s important to understand where your boss is coming from. Because his goal isn’t really to make your life harder, even if it sometimes seems that way.

I know all about this. I was an Executive Director for 8 years. I had the curse.

Come to think of it, I think I always had the curse. When I was 3 I stood on our picnic table and sang gibberish with a plastic ukulele anytime we had a barbeque. The performance was typically not requested.

Pleasers are drawn to nonprofit leadership positions. It’s pleasing to get up at a gala, speak reasonably intelligently and garner applause. It’s good to be Queen.

Then why do many leaders seem to only want to please the board, donors, funders, and volunteers? Why doesn’t the staff make the list?

Two reasons as I see it:

  1. The need to please trumps the reality of execution. In order to make everyone happy you have to block out the notion that the request might be hard (or impossible) or just ridiculous.
  2. Pure unadulterated fear. Pleasers don’t like conflict. Very unpleasant. And saying no to your boss (or someone with more power than you) – well that’s risky business to anyone. To a pleaser, it’s especially hard. Often too hard.

But as you well know, actions have consequences. And your boss needs to understand this.

One of the biggest consequences is that the staff will feel disrespected and resent the boss’ inability to say no. Morale will drop because the staff doesn’t feel supported. If turnover is higher at your nonprofit than you’d like, perhaps the reason is the curse of the pleaser.

The other huge consequence is that the quality of the work will inevitably drop. It has to. You have limited resources and if the staff has to juggle too many balls (and constantly change which balls they’re juggling) quality will suffer.

These are serious consequences. And I was just getting started.


  1. Do NOT complain. It won’t get you anywhere. The boss who can’t say no also doesn’t like to hear the word “no.” Because they just did some heavy duty pleasing. Can’t mess with that. And so you might end up hearing one of those speeches. You know the kind. “If Thomas Edison had complained that he needed more light to invent the light bulb, where would we be?”
  2. Do NOT assume. Do you think your boss knows what you do all day? He or she may not. Remember, your boss is overworked too. Use your weekly check-in (you do a weekly check-in, right?) to educate your boss about the activities you are engaged in. Cover the depth of those activities. Put your work in context – illustrate (a document with percentages maybe?) the growth in your work. Be sure to correlate that with the growth rate – or lack thereof – in your human resources.
  3. Learn to say NO yourself. My blogger friend and colleague Vu Lee has a blog called Nonprofits With Balls. He tells people that the reference is about juggling. That totally works but I believe I mean it differently. A good boss wants push-back from you when appropriate. A good boss needs it. Saying “yes” to your boss is not the key to being a great employee. In the nonprofit world, saying yes to your boss can sink you. Most importantly, it can sink the work. If you’re worried about saying “no”, you might instead say “Yes, but…” That can lead to a discussion about a longer timeframe or an open discussion of why the new item is important and where it fits in the overall priority list.


How do you balance your impulse to please those who have the power to fund your work (or not), lead your board, or even replace you, with your desire to support your staff? Are you the boss who can’t say no?

First, no matter the request, always keep your mission and strategic plan front of mind (you have a strategic plan, right?) This is what really matters. Does the request help move the mission forward or backward? At what cost to the organization? To the staff?

Let’s practice how to respond in a few situations. Here are typical requests a CEO might get from somebody with power – a board member, a donor, a foundation…

1) A funder commits to underwrite a new program that is not part of your strategic plan:

Option 1: Redirect. Is there a way to tie the germ of the funder’s idea into the work outlined in the plan?

‘Of course your idea is a good one and is a testament to how committed you are to our work. Let me tell you about our strategic priorities as approved by the board and give you a sense of the powerful path we have created for moving forward.’

Option 2: Punt and huddle.

‘Wow. How generous and what a testament to your commitment to our work. I’ll clearly need to talk to my team about this idea. You can understand that my strong staff will need to be a part of this decision. And of course you would not want us to jeopardize the quality of the work you support so generously by taking on too much.’

2) The Chair of the development committee asks for a “very simple” report and wants it by Friday (Simple? Yeah right.)

Option 1: Get to the ‘why’ And compromise.

‘Let’s talk a bit more about what you need and why.’

Option 2: Yes, but…

‘Yes, that’s not a problem, but we’ll have to you by next Wednesday. We can’t do a good enough job putting that together without jeopardizing a critical deadline we already have committed to.’

Option 3: Just say yes. After the above discussion, it may just have to get done and folks are going to have to drop what they are doing. But at least you can explain to your staff why this is necessary.

3) A board member has a “great” idea for yet another fundraiser.

What is she really saying? Could she be feeling undervalued?

‘You know Mary, that is a great idea but the staff would shoot me if we added another event. That said, I was talking to Tom the Development Director and he was lamenting that he didn’t have a board member who would take on X – I think you’d be perfect for this. And let’s sit and talk about special events in general so you can be part of brainstorming our plans for next year.’


If you recognize the curse of the pleaser in yourself or your boss, share a story in the comments below. I’ll respond to them all. Tell me about the jam you are in as a result of saying ‘yes’ when you should have said ‘no.’ I’ll offer a few lines of possible script or a few questions to consider before you say one or the other.

13 thoughts on “The Boss Who Just Can’t Say No”

  1. I enjoyed the article, but you are writing from the perceptive of a huge non profit… how about from us little guys do not have all this staff and committees etc working? How do we do things more efficiently??

  2. I think that makes this message even more important – having been an ED of a very small nonprofit (two FT staff – I was one) with a dysfunctional board led me to burnout and the ER. Learning that I was a “pleaser” and then figuring out that it’s ok to draw boundaries may have literally saved my life. I learned that doing things more efficiently meant pushing back, keeping strategic priorities beside me as ammunition, and rebuilding my board with people willing to help in the ways WE needed them to. And the scariest thing I ever did was tell a donor “no.” But I survived – and the organization eventually got its feet under it and is doing just fine. Now I use those skills daily in a larger nonprofit and the staff really respects my ability know when I need them to drop things…and when I’ll push back to defend thier current work load and priorities. It didn’t come easy…but it is a deliberate decision that has to be made and then stuck to! You can do it, too!

  3. This is totally me! Thanks for sharing and writing about this topic. I now feel I have a better handle on how to react in these situations!

  4. I’m a big fan of the “yes, but” strategy – it’s so hard to say no, especially when people are so well intentioned! And happy birthday – it’s my birthday too! Must be something about being a libra and wanting to do good 🙂

  5. I agree Alana. And the rules sort of change when you’re developing a funder with deep enough pockets. I agree with Joan that some direction can be given, but when you’re fighting for life (like many arts organizations) and have a chronically understaffed and underpaid office, you struggle for every penny.

  6. Momnivore. Happy birthday!!! We librans are searching for balance in the world I’m told – maybe that is why we are drawn to NFP work – Trying to get the world in some semblance of order. And people do mean well; your job as a leader is to take their good intentions and direct them in the best possible way toward the pursuit of your mission!

  7. Alana. The issue is the same regardless of the size of the organization. Maybe even worse because saying yes to everyone when you are a one woman show will burn you out so fast you won’t know what hit you. Many of my clients are very small organizations and the staff leader tries to be some kind of superhero. This strategy can lead to a very tattered cape!

  8. Jason. Good for you. I told no to an entire table of 10 donors who each gave $5000. It was awful but right. As a result of holding firm on an organizational decision, I replaced that revenue with new donors – and those new donors were more respectful of organizational decisions

  9. In my early days at GLAAD we struggled for every penny. But I tried never to take any pennies that risked burnout of the staff we needed more than those pennies

  10. My ex boss. She is very young maybe thats the reason… but the worst part about pleasing everyone is that she doesnt care about her staff life, events, ideas, etc. We tried to talk to her but she doesnt listen. She loves people to admire her because she does too much, but every time she commits to do more work, she just give all the work load to us. She is not my boss anymore but she still is with my colleagues. What would you recommend them? .
    I Like your blog a lot. Thank you so much for sharing!

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