Butterflies before bravery: why leaders overthink tough conversations

Even experienced leaders feel it: the anxiety, the second-guessing, the emotional gymnastics before a hard conversation.

A knot forms in the stomach. Sleep gets disrupted. The words spin in circles.
And all of it… before a single word is spoken.

If this sounds familiar, you’re in good company.

Whether it’s letting someone go, calling out unacceptable behaviour, or saying no to a funding request, the emotional weight of these conversations is real. And while it may seem like overthinking is a sign of weakness or hesitation, it’s often a powerful sign of something deeper: you care.

The hidden strength behind overthinking

Too often, project leaders feel shame or frustration when they can’t “just get on with it.” But the truth is, our inner turmoil before a tough conversation is a reflection of empathy, responsibility, and emotional intelligence. You want to get it right. You want to protect relationships. You want to honour the other person’s dignity, even when the message is hard.

This isn’t weakness. It’s awareness.

Instead of suppressing these butterflies or seeing them as a sign you’re not cut out for leadership, what if we saw them as preparation? Emotional rehearsals are your brain’s way of trying to create a safe path through complexity. The key is not to eliminate the butterflies, but to fly with them in formation.

A personal reflection

Recently, I found myself delaying a conversation with a project team member whose behaviour was affecting others. I knew I needed to address it, but every time I opened the calendar to book time, I felt the familiar swirl of hesitation.

What if I made things worse?
What if they shut down or pushed back?
What if they felt personally attacked?

I sat with those questions for a day… then two. But here’s the thing, while I was busy protecting their feelings, I was compromising the wellbeing of the wider team and creating ambiguity about what they stood for.

Eventually, I took a breath, used the framework I share with others, and had the conversation. Was it comfortable? No. But it was calm, clear, and caring – and it led to a reset for both of us.

Why do we rehearse conversations in our heads?

If you’ve ever overplayed or delayed a tough conversation, you’re not alone. It’s a normal response to uncertainty and discomfort. Here’s what’s usually underneath it:

• Fear of rejection – We’re wired for belonging. Tough conversations can threaten that connection.
• Fear of escalation – “What if they get defensive, or it spirals?”
• Fear of causing harm – We don’t want to hurt or offend.
• Perfectionism – We want to say it the “right” way. Spoiler alert: there is no perfect script.

What happens when we avoid the conversation?

Let’s be honest: avoiding difficult conversations can feel like self-protection in the moment. But over time, avoidance has a cost.

• Standards begin to blur.
• Trust in your leadership can erode.
• Small frustrations build into major resentments.
• The issue you were trying to avoid often gets worse.

One of the hardest truths I’ve had to learn and help others embrace is this: Silence doesn’t keep the peace. It just delays the discomfort.

“70% of employees avoid difficult conversations at work, leading to lower productivity and morale” (Crucial Learning, 2023).

The 3C Check-In: a tool for grounding tough conversations

Before your next challenging conversation, pause and ask yourself:

• Clarity – What is the core message I need to express?
• Care – How can I say it in a way that honours the other person?
• Confidence – What will help me stay calm and present?

Writing down your message, role-playing with a trusted peer, or doing a short walk beforehand can help anchor you in confidence.

From butterflies to bravery in action

So, how do you move from overthinking to action?

The shift starts with accepting that discomfort is part of the process and not a problem to fix.
You don’t have to be fearless. You just need to be anchored in:

• Purpose over perfection
• Respect over reaction
• Values over avoidance

When you lead this way, your presence speaks louder than your words.
That’s where trust is built, not in having all the answers, but in being someone willing to show up with honesty and care.

Having butterflies before brave conversations means you’re human. What separates impactful project leaders isn’t a lack of fear, it’s their willingness to walk through it.

It’s not weakness – it’s a signal that you’re about to do something that matters.
Lean into it. That’s where real project leadership begins.