How to Better Approach and Handle Difficult Conversations

We all dread them; here’s how to make them easier.

No matter how strong or positive our personal and work relationships are, sometimes we must have difficult conversations. Most of us dread having to do this because we fear the effect it will have on the relationship. These conversations are called “difficult” for sound reasons; they can have consequences that we would rather avoid.

Past experiences where difficult conversations didn’t go well may prevent us from wanting to address the person about the issue we are having currently. Sometimes, our relationship may already be shaky, or we fear that the conversation will worsen it. We worry that things could become confrontational, and one or both of us will say or do something we regret.

Often we are reluctant to reveal our vulnerable side, or we care for the other person and don’t want to embarrass them, hurt them, or cause them any distress. Sometimes the subject is sensitive, and we know that the other person is reluctant to discuss it. This may happen when it’s time to discuss finances with an elderly relative.

These concerns are real. Difficult conversations can go sidewise fast, so we are strongly tempted to avoid them. While this may work sometimes, it can make things worse in the long run. If the situation continues, anxiety about it and resentment toward the other person can build. What would have been a difficult, but calm conversation initially can become open warfare that permanently damages the relationship. Delay can make it worse.

According to an interview with Stephanie Dean, LPC, CEAP, Clinical Counselor, in Work-Life Connections, Vanderbilt University Medical Center, a greater risk lurks in avoidance.

“I think …one of other risks is that if we do not bring things up, problems or conflicts tend to worsen overtime….Maybe this is something that I have let lie around a longtime, and now it feels even riskier because it is not something that I brought up before. How am I going to bring that up now?”

Avoidance doesn’t give the other person a chance to resolve the issue. If they don’t realize that something is causing a problem for us, they can’t address it. When we finally have that difficult conversation, they will feel blindsided, and the conversation may be doomed from the beginning. Often, it’s best to take a deep breath and, with some preparation, just do it.

“Planning and preparing can help turn down the volume of your apprehension and make it much more likely that the difficult conversations you need to have will be successful.” — Dan Mager, MSW

How to Set Yourself Up for a Successful Outcome

Before approaching another person about a situation or issue, take time to objectively identify the real problem. Sometimes, we think we have a problem because our buttons have been pushed. If this is the case, the problem may have less to do with the other person and more to do with us.

For example, I always am irritated by a sarcastic tone of voice — or by what I perceive is a sarcastic tone. Someone else might find that same tone of voice inoffensive. Nonetheless, when I hear it, my temper flares. I have learned to take a breath and dampen down the flare because I realize that it’s about me and my past, not the other person.

Most of the time, we can let it go and move on, or we can take precautions and let others know where not to tread. According to author and life coach Chris Ellis, it’s good to share our buttons with those we are close to, have them share theirs, and make an agreement to respect them.

Once you decide that a situation requires a conversation to resolve, don’t rush in and confront the person head-on. You need to prepare, so start by asking if they are free to meet with you. If meeting in person, choose a setting that is conducive to private conversations and is comfortable for both of you. Avoid sitting opposite the other person; instead, sit at an angle to create a more collegial atmosphere. During social isolation, schedule a call with a video option like Zoom since you want to see and interpret their facial expressions with sensory awareness.

Decide what to say before you say it

Difficult conversations are fraught with pitfalls. One misspoken word, an inappropriate facial expression, or a lapse of focus can doom the outcome. Improve the odds of a successful communication by clarifying what you want to accomplish with the conversation and how you want the relationship to be afterward. If you want the relationship to survive the conversation and become stronger, you will approach the interaction with a much more resourceful mindset.

Plan how you want to describe the situation that necessitated the conversation. Focus on specific examples of behavior and how you felt when it happened. Keep in mind, their perception may be significantly different from yours. They may not even be aware that there’s a problem, so be open to hearing something different without becoming offended.

Rehearse what you want to say and how you want to say it until you are comfortable. Use language that you would want someone else to use with you in a similar situation, such as “it seems to me,” “it appears to me,” and traditional “I” statements. This captures your feelings and focuses the conversation on what you experienced from your perspective.

Avoid saying things like “I’m annoyed because you ignore me when I’m talking.” Instead say, “[It seems or I feel] that I’m being ignored when I talk. I’d like to discuss this with you.” Limit the use of “you” and “your” since these pronouns set an accusatory, adversarial tone and make the other person defensive.

It’s a Dialogue, Not a Monologue

According to Marcia Reynolds Psy.D., “Remember to check your emotional state before you enter a conversation. People can react to your anger or disappointment. Try to feel hopeful, encouraging, compassionate, or calm. If you can’t shift your anger or disappointment, clearly tell the person why you are having a difficult time feeling anything else.”

Begin the meeting by thanking the person for meeting with you and explain the issue as you rehearsed. Reassure them that you value them and the relationship and want a positive outcome for both of you. Since you asked for the meeting, it’s important that you direct the conversation and keep it positive.

Speak calmly and conversationally. If your emotions are high, try taking deep belly breaths to induce a sense of calm and to sound more confident and assured. Set aside any biases and preconceived beliefs that might impede the conversation and avoid jumping to conclusions.

Ask questions to discover their perceptions. Remember, they may not see that a problem exists, or their perception might be significantly different from yours. Neither of you is right, nor wrong; you’re just seeing things from different angles.

Listen with curiosity and objectivity, not with a need to respond. Accept what they say and how they feel without judgement. Recap what you thought you heard, using their words or synonyms to demonstrate that you listened and to ensure mutual understanding.

State clearly what you want to be different after the conversation and gain agreement from the other person. This may require negotiation or compromise, so be flexible and adaptable. Avoid words like “always,” “never,” “everything,” and “nothing.” Most importantly, never accuse the other person of bad behavior or make them wrong and you right. This will immediately shut down any hope of a positive outcome.

In her YouTube TED talk, Louise Evans, author of Five Chairs, Five Choices, tells a story about her mother, who was prone to exaggeration. This habit irritated Louise, who felt it necessary to correct her mother whenever she did it. Finally, her brother asked Louise, “Would you rather be right or have a relationship with our mother?”

The need to be right can be wrong.

Despite our best intentions, the conversation could become heated. If this happens, take a time out and agree to reconvene when tempers have cooled. Always remember, we are striving for a win-win outcome that supports an ongoing relationship.

How to Ensure a Positive Outcome

The outcome depends on how the conversation evolves and how well we control ourselves and appropriately respond to the other person. This requires us to engage sensory awareness throughout the interaction.

According to Marcia Reynolds, Psy.D.: “Sensory awareness includes an inward awareness of your emotions, intention and regard for people in the conversation. It also includes an outward awareness of people’s experience beyond what is apparent. With sensory awareness, you are able to receive what is going on with others and use this information to better connect, reassure, inspire, activate and invigorate everyone in the field you inhabit with your presence.”

Maintain open, friendly body language and monitor the other person’s body language and facial expressions to see how they are reacting. If you notice resistance or distress in their non-verbal cues, change how you are communicating or ask questions that elicit what they are feeling. Remember, you are striving for a win-win outcome.

Throughout the conversation, communicate that you care for this person and want to continue having a positive relationship with them. Even if the outcome isn’t exactly what you wanted, you will feel better about the situation because you stood up for yourself while being considerate of them and their needs. It takes courage, determination, and high emotional intelligence to have difficult conversations.

“Learning how to have difficult conversations at work or in a personal relationship boosts one’s confidence, increases one’s self-awareness, and the sense of being in control of one’s own life. “ — Aldo Civico Ph.D.

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