Rise & Shine: What If I Speak Up and It Backfires? Navigating the Fear of Self-Advocacy

The Conversation That Almost Didn't Happen

"What if she thinks I went behind her back?"

My client's voice cracked on our Zoom call. Her boss had been on maternity leave for months. In that time, she'd built incredible advocacy with her CIO, mapped out a new career direction, and proven her readiness for the next level.

But her boss? Not exactly known for being supportive. Or easy.

The thought of that "welcome back" conversation—explaining how she'd been positioning herself for a promotion while her boss was out—made her physically nauseous.

Sound familiar?

Here's what nobody tells you about self-advocacy: The conversation you're avoiding is rarely as scary as the story you've created about it.

Let me share what happened next.

The Weeks of Preparation That Changed Everything

We spent weeks preparing. Not just building her business case (though we nailed that). We crafted a narrative that honored what she'd accomplished while showing respect for her boss's return.

We role-played every possible response:

• "Why didn't you wait for me?"

• "You should have consulted me first?"

• "I don't think you're ready"

We prepared for hostility that never came.

When her boss returned and they finally sat down, my client delivered her update with quiet confidence. She explained the CIO conversations, the strategic thinking, the new direction she wanted to take her career.

Her boss's response?

"This makes perfect sense for you!"

Weeks of anxiety. Preparing for battle. Only to find an ally.

Why We Fear Speaking Up (And Why We Shouldn't)

Your brain is wired to protect you from rejection. When you add a difficult boss to the equation, it goes into overdrive:

• "She'll think I'm disloyal"

• "She'll punish me for not waiting"

• "She'll block my promotion out of spite"

• "What if she makes my life miserable?"

But here's the brutal truth: Not advocating for yourself IS the career risk.

While you're waiting for the "perfect moment":

• ✨ Less qualified people are getting promoted

• 🎯 Your skills are becoming outdated

• 💡 Your boss assumes you're happy where you are

• 🚀 The organization is moving forward without you

The 3-Part Framework That Changes Everything

1. Timing Is Strategic, Not Perfect

Stop waiting for ideal conditions:

• There's never a "perfect" time to advocate for yourself

• Major transitions (like a boss returning) can actually create opportunity

• Frame it as an update, not an ambush

Pro tip: Lead with what happened in their absence, then pivot to the future.

2. Lead with Progress, Not Permission

❌ Wrong: "I wanted to wait until you were back to discuss my career"

✅ Right: "While you were out, I took initiative to explore how I could add more value. Here's what I discovered..."

You're updating them on decisions you've made, not asking permission to grow.

3. Make It About Alignment, Not Approval

Transform the conversation from personal to strategic:

• "The CIO and I discussed how this aligns with organizational goals"

• "This move would allow me to support the team's new priorities"

• "Here's how this benefits everyone, including you"

Make your promotion feel like their win too.

The Script That Handles Difficult Dynamics

For the initial conversation:

"Welcome back! I wanted to update you on some productive conversations I had while you were out. I met with [CIO] to discuss how I could add more value to the organization. We explored some exciting possibilities for my growth that align with our team's evolving needs. I'd love to share what we discussed and get your thoughts on the best path forward."

If they seem resistant:

"I understand this might feel sudden. My intention was to be proactive during a transitional time, not to circumvent your input. I value your perspective and want to ensure my growth supports both team goals and your vision as my manager."

To pivot to action:

"Based on these conversations and my recent contributions, I see a clear path to [specific role]. I'd appreciate your support in making this transition. What would you need to see from me to feel confident in this move?"

Critical Mindset Shifts for Difficult Boss Dynamics

🚀 From: "I need my boss to like me"

To: "I need my boss to respect my value"

Difficult bosses often respond better to strength than to people-pleasing.

💡 From: "What if they sabotage me?"

To: "What if they surprise me?"

You're writing a horror story that hasn't happened. What if you wrote a success story instead?

✨ From: "I should have waited"

To: "I showed initiative"

Taking action during their absence shows leadership, not betrayal.

Your Action Plan for Difficult Boss Dynamics

Before the Conversation:

• Document all conversations with other stakeholders

• Build allies beyond your direct boss

• Prepare evidence of your value

• Practice staying calm under pressure

During the Conversation:

• Lead with confidence, not apology

• Focus on facts, not feelings

• Have a clear ask ready

• Don't overexplain or justify

After the Conversation:

• Send a follow-up email summarizing agreements

• Keep other stakeholders in the loop

• Continue building your case

• Have a Plan B ready

The Plot Twist Nobody Expects

My client spent weeks preparing for a boss who would be angry, threatened, unsupportive. She rehearsed defensive responses to attacks that never came.

Instead, her boss—the one everyone warned her about—became one of her biggest champions.

Sometimes the stories we tell ourselves about other people are really stories about our own fears.

The conversation you're avoiding could surprise you.

But only if you have it.

Your Next Step

Fear of a difficult boss is real. Letting that fear freeze your career? That's a choice.

Ready to advocate for yourself, even with a challenging boss? Let's start tracking those receipts for your conversation. You can use my FREE Brag Sheet Template here to start documenting your wins and impact 👉 https://www.riseupcareercoach.com/brag-sheet

If you have your receipts and are ready to start building your business case to your next promotion grab my free guide and template here: https://www.riseupcareercoach.com/getpromoted

What conversation are you avoiding because of fear? Hit reply and let me know.

Keep rising,

Alyssa 💛

P.S. - My client got her promotion, a new trajectory, and something unexpected: a better relationship with her boss. Sometimes advocacy creates respect, not resentment.