Difficult Conversations Made Simple
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Published in Progressive Women’s Leadership

“Difficult conversations do not just involve feelings, they are at their very core about feelings.”

 – Douglas Stone


Let’s face it, most of us dread having that difficult conversation. Whether it be delivering bad news to a co-worker, discussing a delicate topic with a friend, talking to your boss about a work issue that needs to change, or other challenging topics, these conversations are, well, difficult.

Just thinking about such talks can cause excessive worry, apprehension, and problems sleeping, which may also cause you to lose focus on other important work responsibilities. Fortunately, there are tools to effectively manage difficult conversations and achieve the best results.

Establish Positive Intent

When having a difficult conversation, it’s always best to begin with a positive intent. This demonstrates your belief that the other person is not intentionally doing something wrong or trying to create problems. Rather, you’re giving him/her the benefit of the doubt and avoiding making negative assumptions or statements. Your focus is on the future, not the past.

Identify the Desired Outcome

One aspect of difficult conversations is that our goals can change. Hence, you must plan what you want ahead of time. If you don’t have the luxury of planning, you must learn to step back and ask yourself, “What do I really want from this conversation?” In the heat of the moment, our goals can change quickly from, “I’m trying to present/argue a point,” to, “I’m trying to save face, because now I’m embarrassed,” to, “Now I need to win at all costs.” Stepping back and asking what you want can take practice.

By taking the time to prepare to discuss what you want and why you want it, you’ll not only come across as more confident and even-tempered, but the person you are conversing with will have a much clearer understanding of your needs.

Meet Face to Face

Strive to have a face-to-face conversation rather than emailing or talking by phone. When you have a personal meeting, you’ll eliminate any misunderstanding you may receive by email, text, or phone. Face-to-face meetings are the ideal option because you can receive feedback through body language, such as nodding to show agreement, or an arm tightly clenched around one’s chest, which can be a sign of frustration or anger. These face-to-face meetings also make it easier to interpret a person’s feelings, which is critical when having a difficult conversation.

No Blaming

Douglas Stone, author of the bestseller, Difficult Conversations says people spend too much time pointing fingers at who’s to blame, which distracts from the crux of the conversation. Stone says when navigating a difficult conversation, we should “explore why things went wrong, what kept us from seeing them coming, and how we can correct them going forward.” This approach focuses on the issue and not placing blame on anyone. Blaming others is never the answer and will likely never yield a good outcome.

Manage Your Body Language

Our bodies, especially our faces, do a lot of talking for us. When you’re having a conversation, it’s important you pay attention to what your body is saying and ensure it’s syncing with your words. When speaking with others, for example, lean forward slightly to indicate you’re listening and maintain good posture. Nod your head to show you understand or agree. Be mindful of negative body language such as rolling your eyes, even if you don’t believe what you are hearing. We should speak in a way that people will perceive as trustworthy, which includes keeping hand and arm gestures close to the body.

Speak Persuasively

If we can’t convince ourselves of something, it’ll be quite difficult to persuade others. Have you ever known someone who talked so much that other people stopped listening, or when someone always has excuses for what went wrong? These individuals overwhelm their listeners with conversation until the listener becomes confused, bored, or both. Expecting a good outcome and knowing when to stop talking are two of the most important elements of persuading others.

Listen. Really, Listen

Active listening means we strive to understand things from the speaker’s point of view. It includes letting the speaker know we’re listening and understand what was said. This is not the same as hearing, which is a physical process where sound enters the eardrum and messages are passed to the brain. Active listening can be described as an attitude that leads to listening for shared understanding.

When we decide to listen for total meaning, we listen for the content of what’s said as well as the attitude behind what’s said. Is the speaker happy, angry, excited, sad …or something else entirely – that’s really listening.

Be Kind, Respectful, and Empathetic

Above all, remember the Golden Rule, the principle of treating others as you’d like to be treated: with kindness, empathy, and respect. In so doing, your conversation will likely have a successful result and your professionalism will shine.