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The Hidden Habit That’s Undermining Your Leadership (And How to Break It)

WELCOME!

Hi everyone! It’s Kaley.

Thanks for all your thoughtful messages and comments about last week’s Deep Dive on self-doubt; it clearly struck a chord for many of you.

This week, we’re looking at something just as common, but harder to spot: people-pleasing.

⚡In This Week’s Issue:

  • Why people-pleasing is holding you back, and how to shift it.

  • A quick tip to strengthen your self-belief.

  • A question to uncover what’s really holding you back from taking action.

A QUICK TIP TO STRENGTHEN YOUR SELF-BELIEF

When you're worried about what to do or how you’ll be perceived, ask:

“What would the future, confident version of me do right now?”

🧠 Why it works: It moves you out of fear and into leadership energy.

👉 Use it when: Your confidence feels shaky.

ONE CLEAR THOUGHT: A single question to challenge your thinking or change how you lead today.

💬 Take 5 minutes. There’s no ‘right’ answer, just your truth.

Where am I hesitating to take action, and what’s behind that?

📝 How this helps: It surfaces the real reason you're holding back.

🔍 DEEP DIVE

The Hidden Habit That’s Undermining Your Leadership (And How to Break It)

If you’re a woman in senior leadership, you might not think of yourself as a people pleaser.

But ask yourself:

  • Do you say yes when you want to say no?

  • Do you hold back from saying what you really think to avoid conflict?

  • Do you worry more about how others will feel than whether something is right for you or your team?

That’s people-pleasing.

It’s not about being nice. It’s about shaping your behaviour around what keeps others comfortable, usually at your own expense.

It looks like collaboration.

It feels like being helpful.

But it quietly drains your time, clarity and authority.

This isn’t who you are, it’s a learned pattern.

And you can change it.

What People-Pleasing Really Is

People-pleasing shows up as a behaviour, but underneath it’s a protective response your brain has learned to default to.

In neuroscience terms, it’s often linked to fawning, a lesser-known survival response where you appease to avoid discomfort or perceived threat.

While we often hear about fight, flight or freeze, fawning is just as powerful.

At work, it can sound like:

  • I’ll do it, it’s easier that way.

  • Now’s not the time to push this.

  • It’s fine. I’ll make it work.

💡 Insight: This pattern may have helped you avoid conflict or gain acceptance early on, but in senior roles, it chips away at your impact.

Why People-Pleasing Holds You Back

People-pleasing doesn’t just affect how you feel; it affects how you lead.

It can:

  • Make your decisions less clear

  • Dilute your communication

  • Mean you take on extra work that isn’t your responsibility

  • Delay difficult conversations

  • Train others to expect over-accommodation

Over time, it can leave you overextended, under-recognised and quietly resentful, while others see you as agreeable, but not necessarily authoritative.

💡 Insight: If your default is to keep things smooth, you may be trading impact for approval, often without realising it.

Why It’s Hard to Let Go

People-pleasing is often mistaken for emotional intelligence or strong relationship skills, especially in women.

For many high achievers, it becomes the default: keep things smooth, stay agreeable, avoid friction.

But leadership isn’t about being liked.

It’s about being clear, decisive and focused, even when it’s uncomfortable.

And here’s what makes it even harder:

  • Many women still feel expected to be likeable in ways their male peers aren’t

  • Saying no can trigger guilt, even when you know it’s necessary

  • We’ve been taught that good leadership means keeping the peace

Letting go of people-pleasing isn’t about becoming blunt or inflexible.

It’s about making space for honesty, direction and boundaries.

A Practical, Brain-Based Way to Shift the Pattern

1. Notice Where It Shows Up

You can’t change what you don’t notice.

💡 Tip: Ask yourself: “Where am I adjusting, agreeing or stepping back just to keep things smooth, not because it’s right?”

Once you recognise it, you can start to change it.

2. Pause Before You Respond

People-pleasing thrives on speed.

The key is to slow the response.

💡 Action: Before you reply, take a breath and ask yourself: “What would I say if I weren’t worried about someone else’s reaction?”

You don’t have to act on it straight away. But noticing it gives you a choice.

3. Redefine What Good Leadership Sounds Like

You can be thoughtful and still be direct.

💡 Tip: Try saying to yourself, “This isn’t about being difficult. This is about being clear.”

It helps you communicate clearly, even when it feels uncomfortable.

4. Regulate Your Stress Response

People-pleasing often kicks in before you’ve had time to think.

Your body registers discomfort and acts to keep things smooth.

💡 Action: Use a simple physical reset in moments of tension: drop your shoulders, plant your feet, take a steady breath.

This signals safety to your nervous system and makes it easier to stay steady and respond clearly.

Final Thoughts

People-pleasing often starts as a smart strategy, a way to avoid tension, protect relationships or stay on good terms.

But at a certain level, it stops serving you.

You don’t need to over-explain, over-correct or keep the peace at all costs.

What you need is clarity, conviction and the confidence to say what matters, even if someone doesn’t like it.

💡 Action: This week, spot one moment where you catch yourself holding back to keep things smooth. Pause.

Say what you really mean, clearly and calmly.

That’s how you begin to lead on your terms.

📚 If You Want to Dive Deeper…

  • 🎤 TED TalkThe Art of Saying No by Kenny Nguyen. Explores the power of the word “no” and why saying it isn't a rejection, it's a way to protect your time, values and impact. Watch it.

  • 📚 Book: The Disease to Please by Harriet B. Braiker. A practical guide to understanding (and breaking) the approval-seeking habits that hold women back, especially in leadership. Read it *

    *I may earn a small commission if you buy through this link. It’s via Bookshop.org, a B Corp that supports independent bookstores with every purchase.

BEFORE YOU GO…

Here’s How I Can Help

If you’re a woman who struggles with self-doubt or pressure at a senior leadership level, I can help you lead with more confidence and calm.

I offer 1:1 coaching designed to be practical, personalised and results-focused.

👉 Learn more, or if you’re ready to start a conversation, book a 45-minute, free consultation here.

Thanks for reading.

Until next time,

Kaley

PS. If you have any questions, just reply to this email. I’d love to hear from you!

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