How to have an uncomfortable conversation


How often do you put off or totally avoid having difficult conversations?  Does the mere thought of speaking up or asking for what you want create a knot in your stomach?
Last week, I was working with Jill, who was furious with a friend,

“I can’t believe she did it again.  Doesn’t she have any respect for my feelings?  Do I even want to continue this friendship?”
I asked Jill if she spoke to her friend about the issue and she responded,

“I don’t know what to say.  What if I upset her or she gets really angry with me?  Is there a nice way for me to phrase it?"
As she continued expressing her concerns, I pointed out they had little to do with her friend.  Jill was simply looking for a way to avoid feeling uncomfortable. 
“What do you mean?” she asked.
As we continued the conversation, Jill realized her number one discomfort is dealing with her friend not being happy with what she has to say.  The conversation might also stir up anger or hurt feelings,  and Jill may even be on the receiving end of criticism or judgment as well. 

Jill’s discomfort got even worse as she started questioning if expressing herself or asking for something is simply just wrong. 
“Am I being overly sensitive?  Is it selfish to ask her to do something differently?  I should probably just let it go and get over it.”

If you find yourself in this position – wanting to say something but feeling anxious and avoiding the conversation – realize the first step is getting comfortable with being uncomfortable.

Recognizing and accepting what you're feeling, versus running away and avoiding it, makes a big difference.  These acknowledgments actually make a situation less uncomfortable. 

Here are my top 10 tips to get you on the road to speaking up and pushing through the discomfort:

  • Don’t put off the conversation.  If you find yourself repeatedly promising you’ll address it next time, now is the time to speak up.  It’s much easier to tackle conversations as situations present themselves.  Not only can you resolve and move past the issue faster but you will also escape the inner chatter that continues as long as you stay silent.

  • Set up a time to have the conversation - no surprises.  You could say, for example,  “There’s something important I wanted to discuss with you.  Is now a good time or is there another time that works better for you?”

  • Be clear about your intention, concerns and feelings upfront.  For example:  “It’s awkward to bring this up and I don’t want to upset you, but I feel it’s important to talk it through.” 

  • Set up the conversation to put the other person at ease from the start. You are setting the tone for the conversation so they are prepared and open to listening. For example: “I want to share with you what’s on my mind and get your feedback. I realize you may have a different perspective and I want to hear that and understand.

  • It’s important to be graceful in the conversation. If the other person gets defensive or upset when you speak to them, it probably means you are using too much wisdom. Qualify your statements with lines like, “I don’t know if it’s true, but this is how I perceived it.”

  • Focus on speaking directly and put your feelings and requests on the table. If you leave the conversation feeling you didn’t fully express yourself and ask for what you want, then you probably used too much grace.

  • When setting up the conversation start with assuming it’s you. This has nothing to do with being right or wrong, but about never assuming you know what the other person is thinking or feeling. Come from a place of simply wanting to hear what they have to say so you have a better shot at being heard - it usually works.

    When you communicate something difficult and it goes badly, it’s usually because there is an accusation in it or an assumption about something they did. If you start with assuming it’s you, it typically keeps the other person from getting defensive. For example, “I’m not sure if this is true but…”

  • Listen with an open mind, just as you’d want them to listen to you. Put yourself in their shoes and understand what they experienced. The point is to “get” their version. You don’t have to agree, you just have to understand. Acknowledge (and if appropriate apologize) for your part in their negative experience.

  • This isn’t about being perfect, being right, winning or avoiding a fight. It’s about being mature, honest and building better relationships. It’s about being a leader with your communication style.

  • Every conversation will not go as you planned or even as you wanted. It’s also okay to make mistakes at this. It’s okay to need more than one conversation to get it right. It’s okay to be successful with some people and not so successful with others. Remember this is like building a muscle so start with conversations that are slightly uncomfortable for you and build to the harder ones.


I'd love to help you have that conversation you've been putting off.  Click here to schedule a 20-minute complimentary one-on-one consultation with me.