People pleasing is a silent force shaping leadership, especially for women leading startups. Balancing collaboration, influence and decision-making while managing expectations can be overwhelming. If you struggle to say no, avoid difficult conversations or feel stuck when making tough decisions, you’re not alone.

Signs of people-pleasing in leadership

People-pleasing can show up in ways that undermine leadership effectiveness:

• Difficulty saying no: taking on too much to avoid disappointing others
• Avoiding conflict: putting off difficult conversations to maintain harmony
• Overthinking interactions: replaying conversations or worrying about how you came across
• Fear-based decision-making: prioritising approval over what’s best for the organisation and its mission
• Sensitivity to feedback: taking constructive criticism personally.

At its core, people-pleasing is driven by the belief "I’m okay if everyone else thinks I am."

Breaking this cycle requires self-awareness and a shift towards values-driven leadership.

Collaboration vs people-pleasing: knowing the difference

You’re likely someone who has strong values around collaboration and teamwork. But this can often get muddled with pleasing people. True collaboration strengthens leadership; people-pleasing weakens it. Ask yourself:

• Intentions matter: are you making a decision because it’s the right thing to do for the business or because you’re afraid of what people will think if you don’t?
• The price vs the prize: are you holding back on an important initiative to keep people happy even if that initiative benefits the larger organisation? Often the short term relief is not worth the compromise in the long term.
• Emotional awareness: are you agreeing to something out of genuine enthusiasm or are you dreading it but doing it to avoid conflict?

Purpose-driven startups thrive when decisions are made with integrity, not fear of rocking the boat.

The hidden impact on your organisation

People-pleasing doesn’t just affect your wellbeing, it shapes workplace culture. When leaders prioritise being liked over making tough decisions, they:

• delay necessary but uncomfortable changes
• compromise strategic goals to avoid conflict
• foster a "nice" culture where real issues go unspoken

For leaders in purpose-driven organisations, people-pleasing can be particularly dangerous as it can mean prioritising being liked over making the impact you set out to create. Saying yes to every request or avoiding tough conversations to maintain harmony might feel aligned with being ‘kind’ but ultimately it can weaken the very change you’re trying to make.

The cultural impact of people-pleasing in startups

When people-pleasing is widespread in an organisation, it creates a "nice" culture where real issues go unspoken. Employees may avoid raising concerns, opting instead to vent behind closed doors. Over time, this leads to:

• lack of honest feedback
• stagnation and missed growth opportunities
• lower performance due to unspoken resentment.

Creating a culture of open dialogue and constructive challenge is crucial for long-term success. Caring deeply for the people in your team can go hand in hand with challenging directly. Check out the Radical Candor framework by Kim Scott for more support on this.

So what can you do about it?

Set boundaries without losing trust

Boundaries aren’t barriers, they create clarity. Here’s how to set them effectively:

• Start with self-awareness: what fear is making this boundary hard to set?
• Communicate with clarity: explain the reasoning behind your decisions
• Practise saying no: not every request deserves a yes. Consider the "price vs prize"
• Model healthy behaviours: show your team that balance and sustainability lead to better outcomes

Build the courage to say no

We’ve all heard the saying coined by Jane Fonda that ‘no is a complete sentence’ yet saying no can be one of the hardest things to do. It’s crucial for leaders to develop this skill. When aligned with your values and mission, saying no with confidence can actually build trust rather than damage it.

Ask yourself:

• What is the cost of saying yes?
• What is the cost of saying no?
• What example am I setting for my team by setting this boundary?
• When was the last time saying yes went against my values? What did it cost me and my mission? How would saying no have created more alignment?

By modelling clear decision-making, you empower your team to do the same, fostering a culture of transparency and respect.

Shift from seeking approval to purpose-driven leadership

To move from approval-seeking to purpose-driven leadership, cultivate habits that centre you in clarity and confidence:

• Pause and reflect: step out of autopilot and tune into your inner world before making decisions
• Ask yourself key questions: What is most important to me right now? How do I want to show up? What do I want to model?

Use the 5cs framework: inspired by leadership research by David Noble and Carol Kaufman, these five qualities can guide your approach:

• Calm: ground yourself before responding
• Clear: know your priorities and messaging
• Curious: be open to different perspectives and to changing your mind
• Courageous: make bold decisions, say what needs to be said
• Compassionate: lead with compassion towards yourself and others while maintaining boundaries

Create a culture where healthy disagreement thrives

To build an organisation where people feel safe to set boundaries and engage in constructive disagreements:

• Lead by example: model the behaviours you want to see
• Establish clear "how we work" agreements: set expectations for feedback, challenge and decision-making
• Encourage open dialogue: normalise respectful disagreements to foster innovation and honesty
• Prioritise psychological safety: teams perform best when they feel safe to speak up without fear of judgment

From people-pleasing to purpose-driven leadership

People-pleasing may feel like the path of least resistance but in leadership it can hold you back. For women in leadership, especially in the fast-moving world of startups, embracing courageous purpose-driven leadership is key. By setting boundaries, making tough decisions with clarity and shaping the culture you want to see, you don’t just build a more successful business – you create a healthier, more sustainable way of leading.

Breaking free from people-pleasing isn’t just about recognising it. It’s about working through the deeper fears that drive it and building the confidence to lead in alignment with your values. Coaching, supervision or structured reflection can provide the space to step back, tune in and make decisions from a place of clarity rather than external validation.

What’s one decision you’ve been avoiding out of fear of letting someone down? How might choosing alignment over approval change the way you lead?

Astrid is an Executive Coach, Trainer and Facilitator with over 18 years’ experience working with senior leaders in public, private and not-for-profit organisations around the world, helping them to articulate and achieve their goals. She works predominantly with Startup Founders and Executives in education who are seeking to scale themselves, their businesses and their practice. Prior to starting her coaching business, she led the consultancy function of a global education charity - a nimble, fast paced, responsive service working with clients across the globe. She delivers 1:1 executive coaching, group coaching, team coaching and leadership development programmes for organisations that take leadership seriously. 

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