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🔥 Why You Hold Back From Having Difficult Conversations (And How to Speak Up Powerfully)

WELCOME!

Hi everyone! It’s Kaley.

This week, we’re digging into one of the most common challenges senior leaders face: difficult conversations.

⚡In This Week’s Issue:

  • The real reasons you hold back from having that difficult conversation.

  • Three smart, practical resources to help you handle tough conversations with confidence.

  • A simple 3-second pause that shifts how you respond under pressure.

  • And more…

DON’T MISS…
  • 🎧 Podcast - Mastering Difficult Conversations with Sheila Heen. Heen breaks down the three levels most tough conversations operate on, and shares simple ways to approach them with clarity and calm. Listen here.

  • 🎤 TED Talk – 10 Ways to Have a Better Conversation by Celeste Headlee. Straightforward and engaging, Headlee offers ten rules to help people have real, useful conversations, especially when things get awkward. Watch here.

  • 📚 Book - Difficult Conversations by Douglas Stone, Bruce Patton and Sheila Heen. Still one of the best resources on this topic, it breaks down why hard conversations feel so uncomfortable and what to do instead. No fluff, just useful tools you can apply. 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.

QUICK TIP

The 3-Second Rule for Handling Tough Conversations

Before reacting to a difficult situation, pause for three seconds.

Studies show that even a brief pause increases emotional regulation, allowing for a stronger, more strategic response.

ONE CLEAR THOUGHT

📝 Take 5 minutes to reflect—no overthinking, just write!

Where am I holding back my opinion or expertise when I should be speaking up?

🔍 DEEP DIVE

Why You Hold Back From Having Difficult Conversations (And How to Speak Up Powerfully)

One of the most common challenges I see in the ambitious senior leaders I coach is avoiding difficult conversations.

If that sounds familiar, you're not alone.

Almost every leader I’ve worked with struggles with this.

So what's going on, and how can you handle it differently?

5 Reasons Why You Hold Back

#1 Worry About Saying the Wrong Thing

Many leaders stay quiet out of fear of upsetting the other person or coming across in the wrong way.

The fear of getting it wrong can lead to overthinking and silence.

#2 Lack of Training and Role Models

Most people get promoted into leadership without being taught how to handle tricky conversations.

Unless you've had a great role model or specific training, you’re left figuring it out as you go.

#3 Fear of Conflict and Rejection

Human brains crave acceptance.

Neuroscience shows our social brain responds to rejection similarly to physical pain.

We want to avoid difficult conversations because instinctively, we're protecting ourselves.

#4 Perfectionism and Imposter Syndrome

Feeling like you must handle every situation perfectly or risk being seen as incompetent creates anxiety.

Imposter syndrome, common among high achievers, intensifies this fear, making silence seem safer.

#5 Conditioned Behaviour and Cultural Norms

Many women leaders grew up with the idea that confrontation is negative.

Society still reinforces the stereotype that women who assert themselves are aggressive or difficult, which makes it harder to speak up without second-guessing yourself.

The High Cost of Staying Quiet

Holding back might feel easier at the time, but it tends to cause more problems than it solves.

It can chip away at your credibility, erode trust in your team and leave you carrying around unnecessary stress.

Whatever the issue is, if left unspoken, it doesn’t disappear. It still affects performance, relationships and outcomes, just beneath the surface.

And if the conversation is about performance, you have a responsibility to speak up.

Your feedback might be the very thing that helps someone improve, grow and thrive.

How to Speak Up Powerfully: Practical, Science-Backed Strategies

1. Reframe the Conversation

Reframing involves changing your perspective to see conversations not as a threat but as an opportunity.

Positive psychology highlights how this simple shift reduces anxiety, enhancing clarity and confidence.

đź’ˇ Tip: Replace thoughts like "This might cause conflict" with "This is an opportunity for clarity and growth."

2. Master Your Stress Response

When stressed, your body activates a fight-or-flight response, which clouds clear thinking.

Calming your physiological response helps you think more clearly and respond more effectively.

đź’ˇ Action: Practice the 4-7-8 breathing method:

  • Inhale through your nose for 4 seconds.

  • Hold your breath for 7 seconds.

  • Exhale slowly through your mouth for 8 seconds. Repeat twice before the conversation.

3. Use Clear, Collaborative Conversation Starters

Conversations become easier when you start collaboratively rather than defensively.

Choose your language carefully to encourage dialogue, not defensiveness.

đź’ˇ Tip: Use phrases like:

  • “Help me understand your perspective…”

  • “I’d love your thoughts on…”

  • “Can we explore this together?”

These phrases signal openness and encourage cooperation rather than confrontation.

4. Prepare and Practice

Preparation boosts your confidence significantly.

Think through what you want to say and the outcome you’re aiming for; keep it simple and to the point.

Practising out loud helps ensure clarity.

đź’ˇ Action: Jot down bullet points of key messages, and practice aloud once or twice. Clarity reduces stress.

Closing Thoughts

Your team members aren’t mind readers.

As a leader, honest and constructive feedback isn't optional; it’s essential for your team's growth.

Choose just one of these strategies and apply it today.

The more you do it, the easier it gets.

BEFORE YOU GO!

If you’d like to find out more about 1:1 coaching with me to break free from your self-doubt and lead with clarity, confidence and calm, visit my website or book a free, no-obligation chat.

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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