Starting a Difficult Conversation

Starting is often the hardest part of anything, especially initiating a difficult conversation. Difficult conversations, however, are the most important that we will ever experience. Yet, no one teaches us how to do it. We either learn on our own (the hard way) or we learn to avoid them and miss growth and long-term relationships.

A few years ago, my cell phone rang while I was driving. It was one of my dearest friends. She asked, “do you have a few minutes?” This call came on the heels of a long series of electronic communications between us and two other friends about the recent behavior of my boyfriend of 3+ years. The four of us had been friends for twenty years.

I responded “yes, I’m driving to my parents’ house.” She followed with, “we love you and care about you, and I want to share something hard with you.” I consented to hearing what she had to say. She quickly followed with “I have only ever told one other person something like this, so I do not do this lightly. You need to break up with your boyfriend.” I said, “I know.” She sighed. Her approach and the quality of our relationship allowed me for the first to admit aloud what I already knew and was too embarrassed to say to someone else.

This is a personal example, of course, but I offer it because all difficult conversations share a similar combination of discomfort, care, fear, and opportunity. These emotions are present on both sides of the conversation. That is why the initiator must take great care to prepare and even practice before reaching out to the other person.

The way my friend approached me about this super sensitive topic made it easy for me to listen, feel cared for, and respond with openness rather than defensiveness.

She did this by approaching me with empathy, emotional intelligence, respect, and candor, which set the conversation up for success.

Those key elements can be replicated in any difficult discussion if the initiator takes time to do the following in their unique circumstances:

Check your constitution and relationship – My friend was prepared, she asked me if I had time to talk about it, making sure I was ready, and we had an established, productive relationship.

• Prepare yourself and how you will respond beforehand.

• Reflect, acknowledge, and address any emotions you have about the situation to ensure you can initiate the conversation calmly and respectfully.

• Ask yourself, are you the right person to initiate the conversation? Do you have a trusting relationship with the person that will allow them to hear you? Might you need to include a third person in the discussion?

Establish the importance of the relationship – She immediately reminded me how much she and others care about me and that she had something hard to share. This may also sound like:

• "Our relationship is important to me, and I believe discussing [topic] will help us strengthen it."

• "I value our connection, and I think addressing [issue] will contribute to our mutual understanding."

Express your intent with empathy – She made it clear that her intent was to help and that her advice was thoughtfully conceived and not flippant. She could also have said:

• "I am sharing this with you because I care about you, but I know it may be hard to hear.”

• "I know this may be a sensitive topic, but I believe it's important for us to have an open conversation about [issue]."

• "I understand that discussing [topic] might be challenging, but I think it's necessary for us to address it."

Use the assertive communication formula or “I” statements – She began with how she and my closest friends felt and what they observed about the situation, rather than telling me what I was doing wrong.

The assertiveness formula is “I feel [insert feeling] when [behavior] and I need [action].” It can also look like this:

• "I've noticed that [issue] has been affecting our interactions, and I wanted to address it with you."

• "I've been feeling [emotion] about [situation], and I think it's crucial for us to talk openly about it."

Maintain a calm and non-confrontational tone and listen – She was in control of her emotions. This approach and the quality of our relationship assured me that she would listen to me even if I defended the concerning behavior. This might also sound like:

• “I want to understand where you are coming from, will you share your position with me?”

• "I want to understand your perspective on [issue], and I hope we can navigate this conversation together."

• “What I hear you saying is that you need more time to consider this, is that right? When is a reasonable deadline for you and what can I do to support you during this time?”

Initiating a difficult discussion requires careful preparation and intention, which sounds easy unless you are scared, defensive, angry, embarrassed, hungry, lonely, or tired (among others).

Before you approach your next difficulty conversation take time to:

1. Reflect and clearly think through your own feelings and intentions.

2. Contemplate the potential reactions and how you will respond to them.

3. Prepare a clear message that demonstrates empathy and a willingness to listen.

4. Be assertive and using “I” statements rather than aggressively with “you” statements.

5. Remain calm and listen.