Ever faced a tough decision as a leader that you knew was necessary but hesitated because you didn’t want to upset anyone? Maybe it was letting someone go, changing the direction of a project, or setting stricter boundaries. You knew deep down it was the right move, but the thought of disappointing others—or causing conflict—stopped you in your tracks.
Leaders that are people-pleasers often find themselves in this exact position. The need to keep everyone happy clashes with the tough, sometimes uncomfortable decisions that leaders need to make. And that’s where things get tricky. On one hand, you want to avoid conflict and maintain harmony. But on the other hand, effective leadership requires making hard calls that won’t always win you approval.
If you’ve ever been stuck between wanting to please others and making the decisions your role requires, you’re not alone. It’s a real challenge that can hold back even the most well-intentioned leaders. Let’s explore why these tendencies make leadership tough—and, more importantly, how you can start to overcome them.
Can a People-Pleaser Be a Leader?
Yes, but with challenges. People-pleasers can absolutely lead, but the road comes with unique struggles. Leadership requires making difficult decisions, setting boundaries, and sometimes disappointing others—things that can feel incredibly uncomfortable for someone wired to seek approval.
Why Do We Crave Approval?
People-pleasing isn’t just about being nice; it’s actually hardwired into our brains. When we please others, our brain releases a surge of dopamine—the “feel-good” chemical—which rewards us for gaining approval. This reinforces the behavior, making it harder to break the cycle.
At the same time, the brain’s fear center, the amygdala, is activated when we anticipate rejection or conflict. This can make even the thought of disappointing someone feel like a threat, leading to avoidance. For people-pleasers, this fear is heightened, causing them to shy away from decisions that might upset others, even if those decisions are necessary for the greater good of the team.
Related Reading: Why we fear rejection
The Inner Conflict
As a leader, you’re caught in a tug-of-war between the need for approval and the responsibility to lead effectively. Imagine having to lay off a team member who’s underperforming. You know it’s the right move for the team, but the thought of hurting someone’s feelings or causing unrest makes you hesitate. This inner conflict can leave people-pleasers stuck, avoiding tough decisions and risking the overall health of the team.
For leaders who constantly seek harmony, it’s a difficult balance. You want to keep everyone happy, but leadership sometimes requires you to be the bad guy. So, yes, a people-pleaser can lead—but they must first learn how to manage these internal struggles to become effective in their role.
Do People-Pleasers Make Bad Leaders?
Not “bad” – just misaligned. Let’s clear something up: being a people-pleaser doesn’t mean you’re a bad leader. In fact, your empathy and desire to create harmony are valuable leadership traits. The real issue lies in how these tendencies can misalign with what effective leadership requires. The key isn’t to stop caring about people—it’s about finding balance and adapting how you lead.
You’re not a bad leader—you just need to adapt how you manage your team. Leadership is about guiding your team toward the best outcomes, and that sometimes means making tough calls or setting limits, even if it’s uncomfortable.
Why People-Pleasers Might Struggle with Leadership?
One of the biggest challenges people-pleasers face in leadership roles is setting clear boundaries. When your main goal is to keep everyone happy, saying “no” can feel impossible—and that can lead to real problems.
1. Difficulty Setting Boundaries
People-pleasers often struggle to say “no” out of a deep fear of conflict or rejection. In leadership, this might mean taking on too much, overcommitting, or agreeing to things that aren’t aligned with the best interests of the team.
Leaders who avoid setting boundaries may feel like they’re keeping the peace, but in reality, they’re creating false harmony. By dodging tough conversations or failing to address performance issues, they may unintentionally create an environment where real issues are swept under the rug. The result? A team that seems harmonious on the surface but is silently struggling with unmet needs, unresolved conflicts, or unrealistic demands.
Ironically, the fear of conflict that drives people-pleasers to avoid setting boundaries often leads to the very problems they were trying to prevent. Without clear boundaries, leaders become overwhelmed, overworked, and can burn out quickly—bringing that stress into the workplace. Plus, teams led by people-pleasers can feel the impact, too, facing unclear expectations or even being overworked because their leader can’t say no.
The Psychology Behind Boundaries
For many people-pleasers, the struggle to set boundaries is rooted in early childhood experiences. Children who grew-up needing to win approval from parents or authority figures often carry this need into adulthood, shaping how they interact with others. If you felt like love or acceptance was conditional—based on how well you performed or how agreeable you were—it makes sense that you’d grow up constantly seeking approval. This can make setting boundaries feel like a threat to those relationships, as though saying “no” could lead to rejection or disapproval.
Related Reading: Why we become people pleasers
2. Overcommitting
Another common struggle for people-pleasing leaders is overcommitting—both personally and on behalf of their team. You say yes to too many projects, agree to demands from upper management, or overextend yourself to meet everyone’s needs. While this may seem like a way to avoid conflict or keep everyone happy, it ultimately leads to burnout—for you and your team.
When you overcommit:
- Exhaustion creeps in, making it harder to lead with clarity and energy.
- Lack of follow-through becomes an issue, as the sheer volume of tasks makes it impossible to meet every demand effectively.
- Disunity starts to form in your team, as inconsistent priorities create confusion and strain.
- High turnover is more likely, as your team becomes overworked or feels unsupported by a leader who can’t manage the load.
Relatable Scenario
Picture this: a manager who never says no. They take on every project that comes their way and always say yes to their team’s or boss’s requests, even when they know they don’t have the bandwidth. At first, everything seems fine—everyone’s happy because nothing’s being turned down. But over time, the workload piles up. The manager can’t keep up, which means deadlines get missed and quality suffers. Worse, the team feels the strain, too. Because the manager can’t say no, they have to say yes to everything their manager takes on, leaving them stressed and overworked.
This is how people-pleasing can sabotage leadership. While the intent is to maintain harmony, the lack of boundaries leads to more stress, confusion, and eventual burnout—for both the leader and the team. People-pleasers don’t make bad leaders, but without setting limits and managing commitments, they risk burning out themselves and their teams. By adapting your approach, you can lead effectively without compromising the empathy and care that makes you a strong leader in the first place.
How to Overcome People-Pleasing Tendencies as a Leader
Overcoming people-pleasing tendencies in leadership is possible, but it requires awareness and practical steps to break old habits. Below are some key strategies that can help you shift from automatic people-pleasing to a more balanced and effective leadership style.
1. Recognize the Pattern
People-pleasing is more than just a behavior; it’s often an ingrained habit wired into your brain. Each time you say “yes” to avoid conflict or seek approval, your brain rewards you with a small hit of dopamine—the chemical responsible for feeling good. This quick reward reinforces the habit, making it automatic over time. Your brain starts associating saying yes with avoiding discomfort, which can become a pattern that’s hard to break.
But there’s good news: you can rewire this pattern. The prefrontal cortex, the part of your brain responsible for rational thinking and self-control, has the power to override these automatic responses. With practice, you can create a pause between the impulse to please and the decision you ultimately make.
Mindfulness Tip: Pause Before You Say Yes
One simple way to start rewiring your brain is through mindfulness. The next time someone asks you for something, before you immediately agree, take a deep breath and ask yourself, “Is this in the best interest of the team and myself?”
This small pause gives your brain time to engage the prefrontal cortex, allowing you to make a more thoughtful decision rather than an automatic one.
Action Step: Next time you feel the urge to say yes out of habit, try this:
- Pause for 10 seconds before responding.
- Ask yourself: “Am I agreeing to avoid conflict, or is this really beneficial?”
- If the answer isn’t clear, say: “Let me think about that and get back to you.” This gives you more time to assess the request without feeling pressured.
2. Set Clear Expectations
As a people-pleaser, one of the biggest challenges is overcommitting—agreeing to more than you can handle because you want to keep everyone happy. But effective leadership requires setting clear expectations. Defining your limits can feel uncomfortable at first, but it’s necessary to avoid burnout and build trust.
Start by identifying the situations where you tend to say yes, even when it stretches your capacity. These might be moments where you compromise your values, take on too many projects, or agree to unrealistic timelines. Once you recognize these patterns, you can begin setting boundaries to protect your time and energy.
Actionable Questions:
- When do I tend to overcommit? (Is it with certain people, projects, or situations?)
- Where am I compromising my own needs or values to please others?
- How does this impact my effectiveness as a leader?
Action Step: Define and Communicate Boundaries
- Identify one area where you tend to say yes too often (e.g., taking on extra projects).
- Set a limit, such as only taking on a certain number of projects at a time, and communicate this to your team.
- For example, you could say, “To ensure I’m giving my full attention to current priorities, I’ll only be taking on new projects after this deadline.”
This empowers you to focus on what matters and prevents overcommitting while showing your team that clear boundaries lead to better performance for everyone.
3. Embrace Decision-Making
As a leader, you’re constantly faced with decisions that won’t always make everyone happy. People-pleasers often struggle here, avoiding tough choices in favor of keeping the peace. However, leadership requires making decisions based on your company’s values and the best interests of your team—not on what might please others at the moment.
Start Small, Build Confidence. If making decisions independently feels uncomfortable, start with smaller ones. Over time, you’ll build confidence in your judgment and see that tough decisions, when rooted in the team’s needs and goals, actually strengthen leadership.
Questions to Ask Yourself:
- Am I making this decision based on what’s best for the team or to avoid conflict?
- How does this decision align with the company’s values and goals?
- What are the long-term benefits of this decision, even if it’s unpopular now?
Action Step: Practice Decisive Leadership
- Start with smaller decisions. For example, implement a new workflow that improves efficiency, even if some may initially resist the change.
- Reflect on each decision. After making a choice, take time to evaluate the outcome: Did it lead to better results for the team or project? How did you feel about handling the process?
- Gradually tackle larger decisions. The more you practice making decisions based on what’s best for your team or company, the more comfortable it will become.
By embracing decision-making, you shift your focus from seeking approval to confidently leading your team in the direction that serves their long-term success.
4. Clear the Air with Your Team
Once you start making more decisive choices, it’s important to address any disunity that may have built up due to previous indecision or people-pleasing behaviors. Avoiding tough conversations or hesitating to make decisions can leave unresolved conflicts, confusion, and tension within the team.
Own the Past, Build Trust. Clear the air by acknowledging where things might have gone off track. Be transparent about how your past people-pleasing tendencies may have contributed to the current challenges, and take full responsibility. By doing so, you open the door to a fresh start with your team, creating a culture of openness and accountability.
Action Step: Address the Team’s Concerns
- Acknowledge Mistakes: Be upfront about past hesitations, saying something like, “I realize that in the past, I may have avoided making some tough decisions to keep things smooth, and that’s created some confusion for us as a team. I take full responsibility for that.”
- Encourage Engagement: Ask your team for their input. Invite them to share any frustrations they’ve had and be open to what can feel like “criticism.” This demonstrates that you value their perspective and are committed to moving forward together. “I’d like to hear from you—what has been working and what hasn’t? Let’s work on building a more transparent and accountable environment.”
Clearing the air helps you rebuild trust; creating a more united, high-functioning team. By being honest and taking responsibility, you signal that you’re committed to growth—for yourself and your team.
5. Create Real Timelines and Expectations
As a leader, balancing ambition with realistic execution is key to success. People-pleasers often overpromise or set unrealistic timelines to avoid letting others down. This can lead to frustration, missed deadlines, and team burnout. It’s crucial to create timelines and expectations that push your team to grow, but are also achievable within the time and resources available.
Aligning Ambition with Reality. There’s nothing wrong with having high expectations for your team, but it’s important to recognize what’s feasible. Learn to distinguish between goals that are ambitious but realistic, and those that are simply unattainable. Setting clear expectations not only builds trust within your team but also prevents unnecessary stress.
Action Step: Collaborate on Timelines
- Be Upfront About What’s Possible: When a new task or project arises, take the time to assess what’s truly possible. Avoid the impulse to say, “We can do this in 2 days,” when you know it realistically takes 10. Instead, have an honest conversation with your team to align on a timeline that stretches but doesn’t break them.
- Collaborate on Goals: Involve your team in setting deadlines. Ask questions like, “What do we need to achieve this goal effectively?” and “Is this timeline realistic for the scope of the project?” This collaborative approach empowers your team and ensures everyone is aligned from the start.
- Account for Flexibility: Build in a buffer for unexpected issues. This ensures that even if things don’t go exactly as planned, you’re not constantly putting out fires or scrambling to meet deadlines.
By creating real timelines and expectations, you strike the balance between pushing your team to perform at their best while ensuring the goals are achievable. This fosters a healthier, more productive work environment and reduces the pressure to overcommit.
6. Delegate Effectively
One of the most powerful tools for any leader is delegation. But for people-pleasers, delegation can feel like shirking responsibility or burdening others. In reality, delegation is not just about task management—it’s a key strategy for empowering your team and ensuring sustainable productivity. When done right, delegation allows you to focus on high-priority tasks while giving your team the opportunity to shine.
Empowerment Through Delegation. Delegating isn’t just offloading work—it’s trusting your team to take ownership of their tasks and contribute to the project’s overall success. By empowering others, you’re not only freeing up your time, but you’re also fostering growth and confidence within your team. This creates a collaborative culture where everyone plays a part in achieving the goals.
Action Step: Delegate with Intention
- Start Small: If you’re uncomfortable with delegation, start with smaller tasks. Gradually assign more significant responsibilities as your team proves their capability.
- Play to Strengths: Delegate tasks based on your team’s strengths and expertise. This ensures that the work is done efficiently while allowing individuals to grow in areas they excel in.
- Follow Up, Don’t Micromanage: Trust your team, but also ensure that you’re checking in and offering support when needed. Asking, “How can I help you succeed in this task?” shows you’re available without hovering.
By reframing delegation as an opportunity to empower your team, you create a more collaborative environment, reduce your own workload, and enable others to contribute meaningfully to the team’s success.
Link: Harvard Business Review – Delegation
7. Create a Feedback Culture
One of the most significant challenges people-pleasers face in leadership is avoiding hard conversations—especially when it comes to giving or receiving feedback. Without real, honest feedback, unspoken conflicts, tension, and resentment can build up within a team. Over time, this can create a toxic environment where people avoid accountability, and the underlying issues never get addressed. As a leader, it’s crucial to create a culture where feedback is not just accepted but encouraged.
Honest Feedback Leads to Growth. A feedback culture helps resolve issues before they fester and encourages continuous improvement for both you and your team. By fostering open communication, you create an environment where problems are addressed directly, and everyone has the opportunity to grow—without fear of judgment or rejection.
Action Step: Foster Open, Honest Conversations
- Set the Tone for Openness: Start by modeling the kind of feedback you want to see in your team. Be open to receiving feedback yourself. Say something like, “I’d love your honest thoughts on how I handled this project—what worked and what didn’t?” This shows your team that feedback is a two-way street.
- Encourage Constructive Feedback: When giving feedback, focus on specifics. Avoid vague criticism and instead use constructive, actionable feedback. For example, instead of saying, “Your work was off,” say, “I noticed the deadline was missed—let’s work together to find a solution for next time.”
- Schedule Regular Check-Ins: Create formal spaces for feedback, like weekly, monthly or quarterly check-ins. This allows for consistent communication and helps ensure that small issues are addressed before they become bigger problems.
Action Step: Resolve Tension Early
If unresolved conflicts are simmering, address them before they escalate. Ask your team: “Are there any issues we need to bring up that haven’t been addressed?” This clears the air and removes barriers to effective teamwork.
By creating a feedback culture, you not only reduce the tensions that arise from unspoken issues but also build an environment of trust and continuous improvement. In this kind of culture, both you and your team are more likely to thrive as challenges are met head-on and growth is embraced.
Link: Receiving & Giving Feedback- Waterloo University
Conclusion
Overcoming people-pleasing as a leader is a journey that takes time, self-awareness, and practice. With the right tools, leading with confidence and assertiveness is possible without losing the empathy that makes you a strong leader. By learning to set boundaries, delegate effectively, and reframe your mindset around criticism, you can move beyond the traps of people-pleasing and step into your role as a more balanced, empowered leader.
Remember, you do not need to abandon your desire to help others; you just get to find healthier ways to balance it with the responsibilities of leadership.
Take the Next Step: If this resonated with you and you’re ready to dive deeper into overcoming people-pleasing tendencies, we invite you to explore SimplyMidori’s resources on personal growth, relationships, and leadership development. Subscribe to our newsletter for more insights, or consider taking a deeper dive through therapy sessions that focus on unlocking your leadership potential and personal well-being. Let’s grow together—step by step.
