From Anxious to Assertive: Your Workplace Confrontation Roadmap

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For Emerging Leaders: High-potential employees and early-career professionals growing into leadership

Why Speaking Up at Work Feels So Hard

Most employees dread confrontation.

Whether it’s a difficult conversation with a manager, a misunderstanding with a colleague, or pushing back against unfair treatment, confrontation often feels stressful, awkward, or even intimidating.

Many avoid it for three main reasons:

  • Fear of conflict — Will I upset someone or damage the relationship?
  • Fear of emotional reactions — Will I seem too sensitive or aggressive?
  • Lack of experience — I don’t know how to say it in the right way.

But avoidance doesn’t solve the problem.
It makes it worse.

Frustrations grow into resentment.
Unaddressed issues become long-term conflict.
And employees who stay silent often get overlooked for opportunities.

Jorge Loebl highlights this in the Revolving Change Podcast:

“If you don’t address an issue early, it will grow. What could have been a simple conversation turns into frustration, resentment, and disengagement. Avoiding confrontation doesn’t protect you, it weakens your position.”

The good news?
Confidence in confrontation is a skill you can learn.

DISCOVER: What’s Really Holding You Back From Speaking Up

1. Fear of Speaking Up

You worry about the consequences:

  • Upsetting your boss
  • Creating tension with your peers
  • Making the situation worse instead of better

But silence has its own cost.

“If you avoid confrontation because you’re afraid of making things worse, the problem doesn’t go away. It just keeps happening. You have to decide: do you want to be stuck in a cycle of frustration, or do you want to address the issue professionally and move forward?” — Jorge Loebl

When you speak up professionally, you build clarity—not conflict.

2. Emotional Overload in the Moment

Maybe you freeze, your heart races, or you tear up in frustration.
This is your body reacting to perceived threat.

A listener shared on the podcast:

“Every time I have a fight with someone or face emotional trouble at work, I have to fight so hard not to cry. I don’t want to break down every time someone gets angry with me.”

These reactions are normal.
But with the right tools, they don’t have to control you.

3. No Training in Professional Confrontation

Most people have never been taught how to structure a difficult conversation.

So they either:

  • Avoid it until it explodes
  • Blurt out frustrations in an emotional way
  • Use defensive language that escalates conflict

“Most people think confrontation is about proving the other person wrong. It’s not. It’s about finding a resolution. If you don’t structure the conversation properly, it becomes a fight instead of a discussion.” — Jorge Loebl

You don’t need to be perfect—just prepared.

DESIGN: How to Navigate Tough Conversations With Professionalism

Being assertive isn’t about being aggressive.
It’s about showing up with clarity and composure.

Here’s how to do that:

Step 1: Ask Permission First

Instead of jumping into your concern, ask:

  • “Would you be open to discussing something that’s been on my mind?”
  • “Can we set a time to talk about a workplace concern?”

“The first thing you should do is ask permission. When you ask, ‘Can we talk about this?’ you put both people on equal ground. It is no longer an attack, it is a conversation.” — Jorge Loebl

Step 2: Stick to Facts, Not Feelings

Instead of saying:

❌ “You always dump extra work on me.”

Try:

✅ “I noticed I’ve been receiving additional tasks outside my role. Can we discuss how we manage workload distribution?”

The difference?
One invites a solution. The other sparks defensiveness.

“The moment you make it personal, the conversation derails. Focus on the issue, not the individual.” — Jorge Loebl

Step 3: Use the Power of Questions

Questions shift the tone from blame to curiosity.

Try asking:

  • “Can we clarify the expectations for this task?”
  • “What do you think contributed to this misunderstanding?”
  • “How can we resolve this in a way that works for both of us?”

“A question invites discussion. A statement shuts it down.” — Jorge Loebl

Step 4: Mind Your Body Language

Your words matter—but so does your energy.

  • Keep steady (not intense) eye contact
  • Maintain a neutral, calm tone
  • Avoid defensive posture like crossed arms

“Your non-verbal behavior matters. If you come in aggressive, the conversation becomes a fight. If you stay open and calm, the other person is more likely to listen.” — Jorge Loebl

Step 5: End With a Clear Agreement

Every confrontation should lead to action.
Before ending, confirm the takeaway:

  • “So moving forward, we’ll check in before reassigning tasks, correct?”
  • “Let’s agree to communicate earlier when there’s a deadline issue.”

That clarity prevents the issue from repeating.

DELIVER: Build Confidence and Earn Respect at Work

When you handle confrontation with professionalism, you:

  • Speak up without guilt or fear
  • Protect your peace without creating tension
  • Strengthen relationships by resolving—not avoiding—issues
  • Earn trust, clarity, and visibility in your career

“Confrontation is not about winning or losing. It is about clarity, fairness, and moving forward. When you handle it well, people respect you more, not less.” — Jorge Loebl


Learn to Speak So They’ll Listen

If you’re tired of staying silent when it matters, our Memberships can help you change that.

Inside our Memberships, you’ll learn how to speak up with clarity, hold your ground with respect, and build the confidence to grow your career through every tough conversation.

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