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When people are searching for the courage to face a challenging conversation, one of the most frequent questions I get is “How Can I Make Sure I don’t Make Relationships Worse?”

While I can’t guarantee how people will react in any situation, I can offer some suggestions to reduce the likelihood of eliciting over reactions and negative emotions and help you build your courage muscle as you practice having these conversations


Reiterate your reason for talking and then explain why you think           there’s a problem.  Do this in a way that makes it easy for the other person to acknowledge by sharing examples they can easily recall.  Sharing the reasons for the conversation and for your perspective, helps the other(s) prepare and in turn, can positively influence how they respond.

Share what you don’t want.  

When you’re worried about others misunderstanding your intentions, you can prevent it from happening by naming it.  For example, you could say, “I’ve got a problem I want to address that relates to you. I don’t want to put you on the spot or disrespect you in any way but I also want to be loyal to the agreement we made, and I believe you do, too. This is an integrity issue to me. I want you to know where I’m coming from and I want to hear what’s going on for you.”


When it comes time to raise the issue, ask for permission, for example, you could begin with, “I’ve got an issue to address. It’s pretty sensitive, but pretty important. May I proceed?” Asking for permission may seem a bit much, but it is psychologically important.

Surprise breaks safety and invites over-reaction and negative emotion. Giving the other person an opportunity to say no gives them a feeling of control. Asking permission reduces the chances of escalating emotions and reactions and demonstrates respect. If you can do this request in a calm and genuine way, the results may surprise you.

Acknowledge you may be Wrong

When the other person has acknowledged their agreement for you to proceed, share what you’ve concluded from the information you have, but do so in a way that leaves room for discussion and acknowledges you may be incorrect i.e. “That seems to contradict our agreement. Am I missing something here? Did this happen, or is there more to the story?”

These suggestions don’t guarantee that a challenging conversation will go well, but they do increase the likelihood. Even if you’re first attempts aren’t perfect, you can generate more safety with how you act following these conversations. The only way to cultivate your courage muscle for having challenging conversations is to have them, even if they don’t go well at first.

If you want to improve things, show respect and make it safe for others to join you in the conversation. If you’re willing to open yourself up to feedback, it may help others to open up as well.

Onward Courageous Hearts!