Difficult Conversations: What to Know Before You Go 9 Tips to Improve Conversational Effectiveness

I recently spoke at a large company. Afterwards, two executives asked if I would be willing to coach them in dealing with one of their team members. I agreed.

After visiting about the situation, I discovered that the employee in question had a toxic attitude about work, had not been performing the required tasks for their position, and was harboring ill feelings for the supervisor who was hired rather than them. When I asked how long this had been going on, I was told that it had been two years since this employee had been a committed, passionate, and engaged employee.

This situation is not atypical. Difficult conversations are difficult for a reason. Sometimes we are afraid to make a bad situation worse. Sometimes we are afraid of the conflict that could arise when we talk about a person’s deficiencies. Perhaps we realize that we just don’t know how to hold such a conversation, so the whole process is extremely uncomfortable. Whatever the reason, we often avoid holding the conversation, or if we do attempt to have the conversation, it doesn’t go well. Things don’t change or improve, and, in many cases, the situation becomes worse.  

There are several techniques that will greatly improve your success in talking about what matters most. Here are nine suggestions for your consideration:

Assess your objectivity. It is natural to assign blame when things don’t turn out as we expected they would. Rather than becoming frustrated by the outcome, take a moment to think through the current situation and assess your part in it. You might ask yourself the following questions: “Did I clearly give directions?”, “Did I check to see if they understood?”, “Did I set milestones for follow-up and review of progress?”, “Did I ensure that the person had the support and resources they needed to be successful?” Taking a moment to accurately reflect on your contribution to the outcome will set the stage for a more successful result the next time.

Set your assumptions aside. One of the challenges in holding a difficult conversation is the assumptions we may hold about the person or their performance. One should acknowledge those assumptions, and then set them aside. This is about giving the person the benefit of the doubt, and it is not easy to do. We must admit that each person has their own set of life challenges that we know nothing about. Acknowledging that we don’t fully understand the other person’s perspective should inspire us to learn more about their situation when discussing difficult issues. 

Be prepared. If you are going to give someone constructive feedback, you must be able to share what was expected along with the specific desired results. This requires you to identify the facts and detailed examples relating to the situation.

It is also important to share this data before including your opinions and judgments. Stating the facts followed by your interpretation of the results allows the person to understand the logic of your thinking. Sharing your opinions without evidence will create defensiveness in your listener and cause them to adopt a defensive posture rather than responding openly and candidly.

Asking yourself questions such as, “What do I know?”, “What do I think I know?”, “What do I not know?”, and “What do I need to know?”, will help you to structure your conversation to ensure that you gain the information that you need.

Maintain a spirit of discovery. When discussing a person’s performance, we often assume that we have all the answers. Taking the time to ask questions to elicit the other person’s perspective can not only be enlightening, but also increase our understanding of the current challenge. You might try asking the other person these questions as part of your conversation:

  • “What happened?”
  • “What did you expect to create?”
  • “What results did you receive?”
  • “What did you learn?”
  • “What would you do differently?”
  • “What support do you need from me?”

Notice that these questions ask the person to describe the situation accurately while at the same time asking them to project what would need to change. Asking questions such as, “Why did you do that?”, forces people to defend themselves. Such questions make it less likely that the person will openly share their point of view. Approaching a person from the perspective of discovery places the focus on learning about the process rather than attacking or demeaning the person. 

Defuse your negative emotions. If you are upset or emotional in any way, you cannot successfully hold a difficult conversation. Your emotional reaction has the potential to negatively impact the tenor, tempo, word choice, and nonverbal behavior of the conversation. You must be able to speak calmly and rationally to be able to manage the direction and discovery in the conversation. If you are emotional when speaking, your emotions will become the message, and the person will hear very little of what you have to say. They will either meet your emotions by reacting similarly, or they will shut down entirely.

To defuse your negative feelings in a situation, acknowledge your feelings and then uncover your thoughts by finishing this sentence: “I’m (state your emotion) because….” Finish the sentence as many times as you can, and then assess the accuracy and completeness of your thinking. This exercise will increase your objectivity and decrease your negative feelings.

Be respectful. Maintain a controlled demeanor and positive tone. Avoid exaggerated gestures and hand movements like pointing or chopping. Maintain eye contact and be fully present in the situation. Eliminate outside distractions such as phone calls or incoming text message notifications. Ask questions and listen to answers. Use a person’s answers to guide you in asking more probing questions. When a person feels safe, they will reveal their true thoughts in the way they answer. Understanding their thoughts and feelings will help you to create solutions that will help them to help you.

Begin with the end in mind.It always helps to approach a challenging session with a potential solution to the challenge. Then, prepare to learn something that you didn’t know by asking questions and listening. What you learn may improve and change the solution that you originally planned. Do not underestimate that the person you are talking to knows things that you will need to know if you are going to create the best solution possible.

Be courageous. The purpose for holding a difficult conversation is to improve results and change current outcomes. This means that you will not talk around an issue and be less than candid in your approach. State the challenge accurately and specifically. Being vague creates confusion and doubts in the mind of your listener. You want the person to whom you are speaking to completely understand your expectations and the course they should take. This may necessitate that you spend some time clarifying your expectations before you attempt to share them.

Express value.At the end of the conversation, express value for the person, their efforts, and the contribution they will add through their improved performance. You want to leave a person with confidence that they can succeed and that you are there to support them. This will occur as you connect with them in this manner.

Difficult conversations do not have to be as daunting as we often make them out to be. Taking the time to follow these suggestions will greatly improve the quality of the conversations that you hold and increase the effectiveness of your results. 

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