A client came into my therapy office one afternoon ready to quit her job. She’d been passed over for another promotion and had no idea why.
I suggested that before resigning, she ask her boss why she wasn’t advancing.
She came back to her next appointment stunned. Her boss had told her she lacked leadership skills.
“For 10 years, I did everything asked of me,” she said. “If someone said jump, I asked how high. I thought I looked eager. But my boss said he couldn’t make me a leader because I don’t have a backbone. He needs people in charge who can say no.”
She was surprised to learn her eagerness to please was killing her career.
If you’ve gotten caught up trying to make people happy at work, don’t judge yourself too harshly. You probably get praised for going above and beyond. Or you get satisfaction when you are able to clean up messes you didn’t make. So it makes sense you’d want to show off your willingness to be a team player.
But when your eagerness to please is taken too far, you’ll lose sight of your priorities. Even worse, when you don’t treat your time as valuable, other people don’t respect it either.
The solution is to set boundaries—which isn’t an easy task if you fear looking mean or being judged. Taking on extra tasks likely means working longer hours. And research shows when work bleeds into personal time, employees experience more emotional exhaustion and less happiness.
Setting a few boundaries might be all it takes to stop people-pleasing and regain control over your career. Here are four essential boundaries all people pleasers should set at work:
1. Pause before you say yesIf you’re a chronic people pleaser, your default answer is yes—whether you’ve been invited to join an extra committee or handed a task that’s above and beyond the call of duty.
Replace “yes” with a script that becomes your new automatic answer. Saying something like, “Let me check my schedule and get back to you,” or, “I need a minute to think about that,” buys you the time to decide if you actually want to do it.
Ask yourself if the task is something you really want to do. If it is, saying yes is kind. If the only reason you want to say yes is out of fear or obligation, saying yes would be people-pleasing.
When you come back with your decision, skip the apology and the lengthy excuse if you decline. The last thing you want to do is invite a negotiation. Just say something like, “Thanks for asking. That’s not going to work for me.”
2. Stop pretending to agreePeople-pleasing takes the path of least resistance, so you might nod your head during meetings even when you’re not on board. Or you might agree a plan is solid, despite the obvious risks you see, because you don’t want to make waves.
Speak up and share your opinion sometimes. Start with something like, “I’m not sure I agree with that,” or, “Can I push back on one thing?”
Be willing to be the first one to go against the grain. You might find other people speak up as soon as someone else is brave enough to talk first. Even if they don’t, it’s important to show that you have opinions of your own and fresh ideas that can help the company.
3. Stay in your laneRole creep is a common problem for people pleasers. You get volunteered for things because everyone knows you’ll say yes. And you volunteer yourself for extra tasks so you can look like you’re motivated to cooperate.
But every task outside your lane takes time and energy away from your priorities. You become the dumping ground for all the work no one else wants to do, and you might be guilted into taking it on as others try to convince you that you’re the only one who can handle it.
Keep a written copy of your job description handy. Before you take something on, read it and ask whether the task fits your role. If not, decline by saying, “This sounds like it’s outside my role.”
4. Let people feel disappointedYou will disappoint your boss when you ask for more time on a task. You might disappoint a colleague when you decline to help with a project because you’re working on a tight deadline. But you’re allowed to disappoint people.
It isn’t your job to manage everyone else’s comfort. And it’s far kinder to be honest up front than to say yes and resent it later.
Take a deep breath and tell yourself that it’s OK to let people feel bad. Practice asking for what you need and then allow yourself to sit with discomfort when the other person seems disappointed. Learning to manage your feelings–—and letting others manage theirs—can help you build mental strength over time.
Reset your boundaries as neededBoundaries erode slowly over time. Often, we don’t even notice what happened or how things shifted.
So it’s worth pausing every once in a while to evaluate your boundaries and see if there are any changes you want to make. You can reset them at any time.
Maybe there was a short-term project that required you to work in the evenings, but now you want to stop replying to messages after hours. So you set an autoresponder telling people you’ll reply at 9 a.m. tomorrow.
Or maybe you agreed to help a coworker get settled into a new position, but now you’re spending more time than you can spare helping them out. Resetting that boundary might involve saying you’re available only during a 30-minute morning slot to answer questions. It might feel “mean” at first, but ultimately, you’ll be doing yourself a huge favor. And who knows, maybe it’s best for them in the long run too.
Once you start protecting your time and energy, it’s likely that other people will too. And that might be just what you need to advance your career even if you’re a natural people pleaser.
When Clara came to me, she was exhausted, confused, and, for the first time in her career, starting to feel she was losing her ability to lead effectively.
That morning, her boss had done the same thing he’d been doing every week for the past seven months. He had once again changed his thinking on the direction she and her team should be moving. Not two days earlier, she had left a one-on-one with him feeling confident about what he was asking for, and she had communicated the pivot to her team. Now, suddenly, in a meeting with the rest of the leadership team, he announced a radically different concept from what they had already decided.
This was typical of him, and deeply destabilizing for her. Each time it happened, she felt at a loss for what to do. Pushing back in the meeting felt way too vulnerable, and he didn’t seem to be hearing her concerns in their one-on-ones. It was exhausting and overwhelming, and she was not the only one feeling it. Her team was increasingly short with each other, mistakes were being made more frequently, and there was a sense at all levels that people were feeling disconnected and poorly equipped to do their best work.
What Clara was describing is a painfully frequent experience at every level of organizations operating in fast-paced market environments: a boss who seems to be constantly changing their mind about what they want and totally unaware of why others are so frustrated and seemingly unable to deliver.
A problem of perspectiveThe problem is not that Clara’s boss is unfocused or inconsistent. What’s actually going on stems from a clash of perspectives and priorities that are based on different beliefs or experiences. A lack of mutual understanding has translated into a basic communication pattern that everyone on the team—whether they know it or not—is contributing to.
On the one hand is the boss, who is operating from the perspective that creativity and quick thinking are necessary for tackling emergent problems and opportunities. On the other hand, Clara and her team are operating from a belief that their job is to execute on the leader’s vision without “slowing things down.” Likely, they are also worried that asking too many questions will make them seem less competent, while offering pushback might risk their good standing with their boss.
In other words, the team is reacting to whatever decision the boss arrives with that day—just trying to keep up without rocking the boat. The result is what’s known as “courteous compliance”: saying yes when they really mean no. Unfortunately, this only reaffirms the boss’s assumption that there’s no problem—other than the team’s ability to execute fast enough.
But here’s the truth: When your boss keeps changing direction, just trying to keep up will never yield a better outcome. It will only get you more of the same, and the frustration and confusion will simply multiply over time. In fact, the downstream effects of both the frustration and the confusion result in slower and less effective work—exactly what everyone wants to avoid.
Step into the tensionThe most effective thing you can do to break the pattern is not to “manage up” and find a way to tell the boss they’re demoralizing the team. Rather, it’s to step into the tension that emerges when they change direction and start building understanding, no matter how uncomfortable it might feel to do so. It’s time to commit to a conversation built on inquiry and curiosity, regardless of how frustrated you feel. I call this “staying with it,” and it’s a key part of the framework I use to help leaders transform tension into a superpower of group process.
The goal is to understand what’s motivating the change and discuss expectations rather than jumping quickly to action.
Now, your stomach might be churning knowing that there’s a lot at stake and your boss doesn’t react well to questions that seem to slow things down. But if you’re willing to step into this tension knowing that clarity now will enable you to deliver on their expectations more strategically and swiftly later, you will be supercharging your team’s process and taking the first key step to transforming a stuck pattern that’s not serving anyone’s best interests.
When you opt to “stay with it” when your boss suddenly changes directions, there are three priorities to keep in mind. Here, I’ll introduce them to you with some strategic questions and phrases you can rely on to get the conversation started:
1. Reveal the thinking
The objective is to ask questions that uncover the thinking behind the change. The goal is understanding, not course correction. Try asking:
2. Look for alignment
The objective here is to acknowledge where your goals or priorities intersect. This disrupts adversarial communication patterns and affirms where everyone is coming from.
3. Clarify the impact and expectations
The objective here is to share what you notice about the impact. You might say:
Then offer alternatives or negotiate boundaries. You might say:
The goal of “staying with it” is to dig deeper to what’s guiding the change in order to move forward from a place of greater understanding and clarity. Skillfully navigating the tension of these change moments will not necessarily shift your boss’s pattern of making changes frequently, but it will fundamentally alter the outcome of them for you, your team, and even your boss.
Rather than being repeatedly hit by waves and unable to catch your breath, cultivate your ability to navigate the tension of changing directives through the power of open inquiry and goals-based alignment. With key phrasing designed to deepen understanding rather than create friction, you will feel more empowered to lead through change and help your team deliver with clarity, speed, and quality.