In a session recently, a client brought up that he had avoided a chance to help a friend of his take action for his health.

He met up with a friend he hadn’t seen in a long time and wanted to recommend something that has personally helped my client tremendously. At the end of the meeting, he hadn’t brought it up. He wanted my help in reproaching this friend.


Our conversation sounded something like this.

Client: “I was supposed to talk to him about this, but I didn’t find the right time.”

Joe: “Why were you supposed to?”

Client: “I told another friend I would do it and I know it will help him.”

Joe: “Do you want to do it?”

Client: “Yes, I really want to help him and I know I can.”

Joe: “What are you afraid of?”

Client: “I’m afraid he will think I only wanted to see him to tell him this. I don’t want him to think our other friend put me up to it, or that we engineered this meeting for me to confront him. I think he will get defensive.”

Joe: “So you are afraid that if you bring this up, it won’t go well and you will strain the relationship. Not only would you not be helping him, but also you’d make your life harder. Let’s prepare for a better conversation.”


Here are 10 steps we came up with for him having this conversation.


  1. Focus on what you can control. You can’t control other people. You can control what you say and what mindset and energy you bring to the conversation.
  2. Consider that your job is to open a dialogue. The first time you engage in a hard conversation is just that…a first conversation.
  3. Let go of convincing. When we try to convince we are focused on how persuasive we are and ourselves. We are not focused on the other person.
  4. Let go of a specific result or closure. When you are fixated on a target, you aren’t really present for the conversation. Keep the target in mind but focus on connection and curiosity first. Resolutions may or may not come.
  5. Lead with your truth. Don’t try and dance around the truth. People know when you are trying to skirt around what’s real. This may sound something like, “I’m worried that you will take this personally, but I care enough about our project/relationship/you to bring it up anyway.”
  6. Share your experience. Basically use as many I statements as possible. You don’t know if your suggestion or request will actually be good for the other person. You do know why you are recommending it. Speak to that. Especially if it’s something you’ve benefited from.
  7. Talk about the benefits of the recommendation or proposal. People think we make decisions based on features and logic. We don’t. We make decisions based on how something feels and how it will improve our lives.
  8. Ask the other person for their concerns. Get in their world. Get curious about the person in front of you and their experience. Often we are so ready to get out of the conversation that we don’t even know how the other person is experiencing it.
  9. Ask for questions or reactions.
  10. Allow the other person their response. They may completely agree with you, but human beings don’t’ like change. It’s highly likely the other person will be defensive, resistant, frustrated, curious or might even shut down. Allow it. If you really want the person to stay open to further dialogue, you have to permit them their experience and reaction.


What I propose here will help you have better conversations that are challenging, especially when you are trying to get someone to do something. These 10 tips also take a lot of cultivation of skills and mindset. It won’t come naturally at first.


If you find yourself shying away or faltering in tough conversations, reach out to work with me.