Exactly how to express disappointment or frustration with your boss

Bobby sat at his desk, rewriting the same email to his manager over and over. His boss had just announced a major reorganization without acknowledging how it would impact several critical projects Bobby led. Bobby knew he needed to address the issue, but he didn’t want to seem difficult or negative. But staying silent didn’t feel right either.

Bobby found himself in a situation many professionals face—unsure about how to bring up frustrations and disappointments to those in charge. It’s tempting to avoid these tough conversations. You don’t want to damage the relationship, but it’s hard not to be upset by sudden changes or what you see as poor choices. 

While it might feel nerve-wracking in the moment, speaking truth to power is one of the most worthwhile skills you can build. Not only does it prevent simmering resentment that can lead to burnout, but it also allows you to feel proud that you stood up for your values. More importantly, expressing your disappointment in a respectful way signals emotional maturity, proving you can handle pressure and operate in high-stakes moments. 

Here’s how you can share frustration with your manager in a way that’s clear, constructive, and strengthens your relationship instead of hurting it: 

Explore the worst case, best case, and most likely 

It’s easy to overthink and wonder, “What if my boss gets defensive?” or, “What if this ruins our relationship?” Bobby worried that his manager would say he was overreacting or that it’d jeopardize him being assigned to future projects. To ground himself, he walked through three possibilities:

• Worst case: What was the absolute worst that could happen? Bobby had advocates across the company. If things really went south, he had options and that gave him peace of mind.
• Best case: What’s the ideal outcome if everything goes well? Surprisingly, Bobby hadn’t even considered the upside. His manager might appreciate the feedback, adjust plans, or at least acknowledge how the changes were impacting the team. 
• Most likely: What’s the realistic outcome? Bobby’s boss might be slightly annoyed in the moment since he was under a lot of stress, but it probably wouldn’t be a major rupture.

This quick exercise shifts you out of emotional reactivity to a more balanced, rational place, so you approach the conversation calmly and constructively.

Get buy-in first

Don’t launch right into your frustration or disappointment. Start by getting a “micro-yes.” For instance, you might say something like, “Do you have a few minutes to talk something through?” or, “I’ve been reflecting on something and would love your perspective. Would now be a good time?” 

This small gesture works because of the consistency principle, a psychological tendency where people want to align their words and actions. When your manager agrees upfront, they’re more likely to stay open because they’ve said they’re willing to talk. 

Find common ground

Continue to ease in by creating a shared goal. Set the tone that you’re a partner who is working towards the same outcome, not an adversary. This shifts the dynamic from “me versus you” to “us against the problem.”

You might say:  

• “We both want this project to succeed, which is why I wanted to share something that I think could be getting in the way.” 
• “I really care about the team’s well-being, and I know you do, too. That’s what’s motivating this conversation.” 

Use words that reflect their style and priorities

Match your message to what matters most to your boss. If they’re deadline-driven, frame your feedback in terms of how it impacts timelines. If they’re mindful of their reputation, emphasize how the issue affects the team’s perception. 

Bobby’s boss prized quality. So, instead of leading with how the reorg made him feel—overlooked and angry—Bobby mentioned how the changes would create confusion around ownership and lead to gaps in their delivery. He wasn’t sugarcoating or pandering, but rather translating his message into language his boss would be more receptive to. 

Critique the situation, not people

Lower defensiveness by using neutral, observational language, like, “It seems that . . . ” or, “When X happens . . . ” versus statements that start with “you” or “I.” For example: 

• Instead of, “You didn’t give us a heads up,” try, “When changes are shared with short notice, it’s harder for us to adjust.”
• Instead of, “I think our communication is scattered,” try, “This approach seems to be creating more back-and-forth than necessary.” 

Better yet, add a suggestion or a solution, such as, “I could set up a recurring check-in with the client to help us stay ahead. Would that be useful?”

Get their side of the story

Show you understand that your leader is dealing with pressures, too. You might say, “I’d like to understand what constraints or considerations you’re facing that might have influenced this decision. I realize I may not know the whole story.” This demonstrates that you’re able to balance your own concerns with their reality, which can instantly defuse conflict. 

You can care deeply, feel disappointed, and still tackle the situation with curiosity, confidence, and conviction. By doing so, you’re building the foundation for long-term trust and respect.