The subtle art of correcting your boss .Four winning strategies for saving a more senior leader from a mistake—without tanking your career in the process.



Unless you're at the very top of an organization, managing upward—shaping and influencing the decisions of those above you—is part of the job. One of the trickier aspects of this is addressing a mistake or misperception held by a supervisor or senior colleague.

The ease of correcting someone in a higher role depends heavily on both the individual and the company culture. In the ideal workplace, feedback flows freely in all directions. I personally make it clear to my team that I welcome concerns and corrections early and often—because it’s the only way to lead effectively.

But not all environments are as open, and not every leader is immediately receptive. If you're unsure how your feedback might be received, here are some strategies to consider:

1. Start by Asking

Don’t assume senior leaders are resistant to feedback. People with a growth mindset typically welcome input—even critical feedback—more readily than those who view criticism as a threat to their competence. Hierarchical cultures may make upward feedback more difficult, but individual differences still matter a lot.

When working with a new leader, ask how they prefer to receive information. This doesn’t have to be about correcting them directly—just open a conversation about how best to share insights from your unique vantage point in the organization. That will give you a read on whether they value input from below or expect a top-down flow of information.

2. Be Discreet

Even the most feedback-friendly leaders usually don’t appreciate being corrected in front of others, especially peers or senior stakeholders. If you need to point something out, do it privately.

When you do, frame the conversation as sharing additional context they may not have had, rather than positioning it as a correction. That approach helps preserve their authority while updating their understanding.

3. Create Contradictions

Correcting someone is really about helping them change their mind. One of the most effective ways to do that is by introducing a contradiction—something that doesn’t quite line up with what they currently believe.

This works best when it’s subtle. Present the contradiction and ask for their perspective: “I noticed X, but we’re also assuming Y—do you see a way to reconcile that?” This allows them to explore the issue on their own, rather than feel like they’re being told they’re wrong. It’s a more collaborative, less confrontational path to correction.

4. Find an Ally

If the person you're trying to correct is particularly resistant to feedback, consider enlisting someone they trust. A peer or close colleague may be able to offer advice on how to approach the conversation—or even help deliver the message directly.

5. Don’t Overestimate the Risk

It’s natural to dread these conversations, but the anxiety beforehand is often worse than the conversation itself. While you should always approach these moments with respect and discretion, know that most people appreciate honest, well-intentioned feedback more than you might expect.


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