Sometimes, the worst part about a hard conversation is all the time you spend stewing about it. There’s often a lot of anxiety around not knowing exactly what you’ll say and not knowing how the person will react. In other cases, you know both of these things with near certainty, but you still feel anxiety about facing that person.  When you’re dealing with your boss, it can add an even higher level of complexity. There are different ways of addressing tough conversations with your boss that will help strengthen your relationship, not destroy it. We have three recommendations if you find yourself needing to give constructive feedback up the ladder. 

Tip 1: Consider the pros and cons of having a hard conversation.

Before giving any feedback, you’ve got to first weigh the risk with the reward. While giving feedback is important, doing so might not be the best course of action. Consider why you want to give the feedback in the first place. If it’s to help your boss improve or to build a stronger relationship, those are reasons with merit. But if you’re wanting to make your boss look bad, your actions aren’t honorable and can backfire. There are more constructive ways to deal with what’s fueling your vindictive feelings.

Additionally, giving your feedback isn’t always in your best interest. There are, unfortunately, many reported instances where giving feedback caused more problems for the subordinate. Here’s an example – the person at the heart of the issue seems unwilling to listen and lacks the self-awareness to understand the challenges the subordinate faces when trying to discuss the matter with them. The reality is, employees do risk retaliation in some cases whenever honesty and open communication up the ladder takes place. Before you act, gather some intelligence to determine if it’s safe to proceed with giving your feedback directly to your superior. Look at the company culture as a whole to get clues for how your leader may react. Does the organization value open communication? Do people share accountability? Do people point out issues or have disagreements and then move on? If the answers are no, pump the brakes on initiating your tough conversation, and look at other options. Understand there’s a range of ways you could choose to handle the problem with your boss. Now might not be the ideal time for a discussion, but there could be a better one in the near future. It might be in your best interest to talk with someone even higher up, or engage a mentor outside the company for guidance. 

Tip 2:  Prepare your delivery.

If you’ve investigated and come to the conclusion that it makes sense to have a difficult conversation with your boss, you’ll want to make sure the person can really hear what you’re saying over any internal narrative that might be trying to play as you are talking. Think about how you would want to hear bad news, if you had to hear it, and approach the person with their feelings in mind. 

  • It never hurts to role play with a mentor or someone close to you beforehand. Saying the words out loud prior to the real conversation reduces anxiety.
  • Try to find a time when the recipient appears more relaxed and receptive. 
  • Keep it private, involving only the two of you. 
  • Don’t lead with the problem. Wait for the dialogue to present an opening for you to naturally approach your topic. 
  • When that opportunity comes, start with a positive observation. 
  • Then appeal to the person’s empathy by explaining why you are providing the feedback. 
  • To minimize confusion and irritation, be specific about your feedback. Focus on specific behavior and its impact on you or your work. Avoid using words like, “always” and “never”.  
  • Have one or two recent examples of the problem behavior ready to use in your explanation. 
  • Be ready to describe the alternative behavior that you’re proposing in your discussion. This gives the offender actionable solutions. 

Tip 3: Reduce your risk. 

360 reviews are a great tool for gathering robust and anonymous input about an individual’s behavior. You could encourage your boss’s manager or HR to conduct one. The third-party data collection process gathers anonymous feedback across many departments and employees. You are removed from the responsibility of delivering the results. Additionally, there’s always the option to provide feedback anonymously, but make sure if this is your intention, you don’t give details in your feedback that give away your identity. And if you go the anonymous route, make sure you provide any positive progress anonymously when you see change being made. 

Look to a mentor or someone with experience that you trust who’s willing to discuss your situation with you. An outside perspective can help you to see the situation and options more clearly. And, talking with a person more removed from the emotional aspect of the problem can help you to put the challenge in perspective.  


The truth is, over a long career, you’re bound to face friction with a boss or two. Make a point to learn how to effectively confront these types of problems. Doing so improves your leadership skills and reduces the stress and anxiety that comes with inaction and indecision.

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