How to Influence Your Boss and Share Critical Feedback

Episode 297: How do you give critical feedback to your boss without risking the relationship, overstepping, stressing out, or burning bridges?

You’re juggling priorities, managing a team, and trying to meet expectations. But what happens when your manager’s decisions create more chaos than clarity? In this episode, you’ll get practical tools to shift that dynamic and build a stronger, more strategic relationship with your boss—no drama required.

Here’s what you’ll walk away with:

• A mindset shift and strategy to understand what really drives your manager (and their manager).
• Communication techniques to present ideas that actually get traction—backed by data and story.
• A smart, respectful way to say no or share feedback without damaging the relationship.

Hit play now and learn four proven communication tactics that will help you influence up and take more control of your work life.

Shifting Your Mindset to Influence Up

⏱ 0:00 – What this episode delivers.
David kicks things off with a listener-favorite question: How do I influence my boss? He explains how these four communication skills will help reduce overwhelm, build trust, and create a stronger working relationship.

⏱ 2:00 – You can’t change your manager, but you can influence them.
Learn why influence starts with understanding—not control—and how shifting your mindset can give you more clarity and confidence.

⏱ 3:45 – Start with two-level thinking.
To truly influence your boss, you need to know what matters to their boss. David explains how identifying goals, problems, and pain points two levels up unlocks strategic alignment.

⏱ 5:45 – Make the business case with data and story.
Don’t just present numbers—make meaning out of them. David shares how combining data with a clear recommendation and relatable story makes your message stick.

⏱ 7:20 – Anticipate questions before they’re asked.
Avoid getting blindsided in the moment by thinking like your boss. Anticipating their most obvious questions helps you stay composed and credible.

Communicating Clearly—Even When It’s Critical Feedback

⏱ 8:45 – Say yes to say no.
Instead of rejecting requests outright, David outlines how to affirm shared goals while offering alternatives—a respectful way to protect priorities without damaging the relationship.

⏱ 11:35 – The only approach that works for giving critical feedback.
When it’s time to speak up, permission is key. David shares a technique to offer critical feedback to your boss in a way that invites dialogue, not defensiveness.

⏱ 13:45 – How asking permission changes the tone.
Positioning your feedback as support for your manager’s goals opens the door for influence. David explains how this approach keeps the conversation constructive.

⏱ 15:30 – What to do if your boss doesn’t want feedback.
If your manager declines, respect the boundary—but don’t lose heart. David reminds you to focus on building credibility so you’ll have more influence in the future.

⏱ 16:17 – When and why to give critical feedback at all.
David closes with a reminder: not all feedback is worth sharing. Choose moments that matter for team health and your own mental wellbeing—and where critical feedback truly serves the bigger goal.