4 scripts to help you talk to a difficult boss without hurting your career

A coaching client came to me last week frustrated.

Her boss wasn’t responding to messages. He showed up late to their one-on-ones. And he looped other decision-makers into projects without telling her.

Her boss was basically undermining her at every turn.

(I’ve been there, and I know how frustrating this is.)

She wanted to march into her boss’s office and say: “I can’t work this way. Do you have feedback for me? Is there something I’m missing?”

I stopped her.

That conversation would’ve tanked her career.

The Problem

When you’re frustrated with your boss, your instinct is to focus on how you feel.

“I don’t understand what I’m doing wrong.”

“I feel like you don’t trust me.”

“I’m confused about why you keep changing direction.”

All negative. All focused on you. All complain-y.

I need you to hear this:

Even if you’re 100% right that your boss is being difficult, this approach makes YOU look like the problem.

The Big Small Thing

When you need to address a difficult relationship with your boss, use what I call “savvy authenticity.”

This isn’t about being fake. It’s about being strategic.

Think about it this way: You don’t want your surgeon saying, “I had a fight with my wife this morning and really don’t feel like doing your knee surgery.”

You want them to say, “I’ve done this surgery 2,000 times. You’re a great candidate. Your recovery is going to be smooth.”

Is that authentic to how they’re feeling? Maybe not. But is it what you need as a patient? Absolutely.

Your boss is your customer. Give them what they need, not what you’re feeling.

DON’T say this to your boss:

• “I don’t understand what I’m doing wrong.”
• “I feel like you don’t trust me with this project.”
• “Why do you keep changing the timeline without telling me?”
• “I’m frustrated that you’re not responding to my messages.”

DO say this instead:

• “What would a win look like for you on this project?”
• “How can I make your life easier as we move through Q4?”
• “What’s your biggest priority right now that I should be thinking about?”
• “I want to make sure I’m aligned with your vision. Can we schedule 15 minutes to sync?”

The shift:

Stop asking: “What am I doing wrong?”

Start asking: “What would success look like for you?”

Stop saying: “I’m frustrated.”

Start saying: “How can I help?”

Note: Sometimes you can’t have the direct conversation with your boss. In that case, talk to a trusted advisor, a colleague, or your boss’s boss — and use the same approach.

Focus on understanding what success looks like for your boss, not on venting about how frustrated you are.

Want more help dealing with tough situations? Grab my free PDF: 8 scripts to help you say “no”

How This Helps You Get What You Want

When you approach a difficult boss relationship with negativity and complaints, you look like part of the problem.

When you approach it with savvy authenticity — focused on them, the business, and staying positive — YOU look like a leader.

Save the venting for your best friend over drinks.

At work, be savvy.