You Want Me to Say WHAT to my Boss?

When it comes to difficult conversations with the boss, there is the conversation we have in our head, the conversation we say out loud and the conversation we really need to have. Here are a few examples…

In our Head:
Dear Boss, I want to quit you.

What we say in out loud:
Dear Boss, I can’t make it to work today, I’m sick (fake cough, fake sneeze).

What we really need to say:
Dear Boss, I’d like to share with you how things are shaking out for me. Sometimes I struggle with keeping up with your requests. And when I signal I can’t take more on, I sense that it frustrates you. That leaves me feeling overloaded and unappreciated. I know that is not your intention, but it is how I feel. Can we have a conversation about how we work together?

In our Head:

Dear Boss, I blew it…. Again.

What we say out loud:

Dear Boss, Look over here at all the great things I’m trying to do but don’t look over here at my failures.

What we really need to say:

Dear Boss, I know I’m not meeting your expectations and you’ve lost confidence in me. This is not the leader I want to be and I need your help. What can I do to turn things around?


In our Head:

Dear Boss, Your strategy stinks.

What we say out loud:

Dear Boss, Sure, that strategy can work … if we have a decade to execute and a ton more resources.

What we really need to say:

Dear Boss, Based on what I’ve seen and the feedback I’m hearing, I don’t have confidence this strategy is realistic. Can we discuss some of the information I’ve gathered that you might be unaware of? This certainly doesn’t mean I won’t support you moving forward, I just want to have a conversation before we get too far down this path.


Any of this sound familiar?

This last month coaching leaders all across the globe, I found it interesting how often the issue of delivering tough messages to the boss came up. Of course, this is never fun. In my conversations with these leaders, what I learned is that there are two key reasons they struggle with providing honest and direct feedback to their boss. First, they are fearful of the consequences of being honest and second, they don’t know how to deliver the message. As a result, they struggle with both the willingness and skillfulness needed to appropriately handle tough conversations with their boss. You yourself have probably faced this at one time or another and if you thought you were the only one, rest assured, you’re not. Statistically speaking, confrontations of any kind are the most likely low scoring competency for leaders and individual contributes alike according to Lominger (a Korn Ferry Company) research. It takes a courageous and skillful leader to say what really needs to be said. We call these this type of honesty, Courageous Conversations.


Courageous Conversations are the ability to say what needs to be said but in a way that others will hear so that ineffective behaviors change.

You don’t have to be a polished CEO to do it well, you just have to have enough spine to step up to the challenge and a clear game plan to assist you in your successful execution.

Here are some tips for developing a game plan

1)      Preparation is key- don’t try to wing it

Preparation is the key to a successful conversation. Script out what you want to say so that you have some key phases down. You may even want to role play the conversation with someone you trust to practice actually saying the words out loud and to get feedback. We can’t always prepare for courageous conversations, but the more we plan when we can the more effective we’ll be when we are faced with a courageous conversation on the fly.

2)      Consider the other person’s style

Knowing how someone prefers to communicate or knowing what they value and what is important to them is useful information in crafting your message. Take time to consider how this person tends to react to various approaches not just with you but with others and use this information to help you best adjust your approach.

3)      Say what needs to be said- don’t be wishy washy

Saying what needs to be said in a way that others will hear it does not mean that you need to water down, soften or dilute your message! That is not the intention of a courageous conversation at all. Instead, say what you mean, be direct. But also be considerate of the other person. This is not about being brutally honest but about humanely honest. Say what you need to say but say it in a caring, exploratory and thoughtful way.  If you walk away feeling like the issue is unresolved then it’s likely you didn’t say what needed to be said.

4)      Ask for a commitment

Don’t walk away without asking for behavior change you want to see. Once you’ve ask for the behavior change, ask for a commitment to that behavior change. You can have an amazing courageous conversation and if you forget to ask for a commitment, you can’t be sure you’ve actually got buy-in to do something different.

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