How to have difficult conversations

Angela Joyner. Photo by Andrew Collings.

Valentine’s Day is quickly coming upon us and I am sure many of us will be spending time with a significant other or friends.  Having healthy relationships is a part of our lives, however, many of us shy away from having those difficult but necessary conversations.  Many people avoid confrontation altogether, while other head into haphazardly without being responsible for how their message is heard.

As leaders it is our responsibility to not only deliver the message, but also be responsible for how the other person might receive the message.  There are several steps you can take to help make difficult conversations easier. Whether it is with your spouse, child, co-worker or boss, you will at some point encounter a difficult conversation.  How you handle the conversation will say a lot about your leadership style and your concern for the other person.  What difficult conversation do you need to have in your personal and professional life?  What keeps you from having that difficult conversation?  Do you plan for the conversation or just jump in?

Coaches Challenge:  Identify a difficult conversation you need to have and practice one of the techniques identified in the article below.  Remember you are building a communication muscle that will serve you well in your leadership.

Say the Hard Thing:

How to Have that Difficult Conversation

Planning for Difficult Conversations

“There are no classes in life for beginners,” wrote poet Rainer Maria Rilke. “Right away you are always asked to deal with what is most difficult.”

Saying the hard thing can be one of the most difficult things we ever do. For many of us, just thinking about having difficult conversations can cause worry, fear and stress. The good news is that getting these conversations right has more to do with planning and practice than saying “just the right thing.”  Furthermore, when we dare to broach these hard topics with other people, there are often hidden rewards.

The Benefits of Speaking Up

Difficult conversations have the power to get you what you really want from life. They can clear the air between you and someone else. And they can give your self-esteem a real boost.

Revealing how you really feel and what you really want is a life-long practice that sets you up for more good things in the future. Most people are not mind readers and we have to take the responsibility for telling others what we need and set respectable boundaries.  Regardless of how the other person responds, making your true self visible will only make you stronger, healthier and more at peace with yourself.

Setting the Stage for a Productive Conversation

1. Bring it up. It’s wishful thinking to hope that the other person will broach a hard topic. In some cases, he or she may not even be aware of the need. That means, like it or not, it’s up to you.

2. Be clear on your intention. Are you discussing a sensitive topic to make a decision, reveal what you’ve already decided, make a request, or something else? Being clear about why you are having the conversation—and what you hope to get out of it.  By having an objective and clarity about what you need will help you frame what you’re about to say.

3. Be mindful of your mindset. Sidestep the tendency to blame and assume you know exactly what is going on. Leave room in your frame of mind for discovery and revelation. Stay curious. Remember how much you care for the person, and envision how you’d like your relationship to be after the conversation. Approach the conversation with positive intent.

4. Rehearse. It can helpful to practice your conversation by writing in a journal or talking it through with a trusted friend or therapist. This will help you become more familiar with your feelings and point of view, and help you relax before you say the hard thing.  By jotting down a few talking points, you can focus on how you deliver the message and not just the content. 

5. Set the tone: Use “I” messages. “You” statements tend to assign blame. For example, rather than saying, “You hurt my feelings,” it is better to use an “I“ statement and say, “I feel hurt.“ If you’re afraid, say what you’re afraid of at the beginning of the conversation. For instance, “I’m scared that you won’t like me anymore or that you’ll go away or that we won’t be friends anymore after this conversation.” Then take a deep breath and begin.

Saying the hard thing is like any other exercise: every time you do it, you are building a muscle. Your hard work will unquestionably pay off in more meaningful relationships in the end.

Author’s content used under license, © Claire Communications

Wonder Loft wisdom


“Nothing lowers the level of conversation more than raising the voice.” —Stanley Horowitz

“Have the courage to be sincere, clear and honest. This opens the door to deeper communication all around. It creates self-empowerment and the kind of connections with others we all want in life. Speaking from the heart frees us from the secrets that burden us. These secrets are what make us sick or fearful. Speaking truth helps you get clarity on your real heart directives.” —Sara Paddison

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