8 Tips for Making Difficult Conversations Easier

December 20, 2021

Difficult conversations are never fun, and they can be challenging when they involve an employee who must improve their productivity, behavior, or both. Whether you are delivering the conversation or you are on the receiving end of it, the entire process can be a challenge. Anxiety, discomfort, and all that fun stuff can really take over if you're not careful, so you have to make a concerted effort to be professional and respectful so that people don't walk away saying, "Oh, I hope I never see you again."


I recently heard Rhonda Scharf speak on this subject. Rhonda is a well-recognized Professional Speaker, Trainer, Consultant, and Author who splits her time between Ottawa, Canada and Fort Myers, Florida. Rhonda shared her favorite quote from Maya Angelou and I think it has a lot of value for this topic, "People will never forget how you made them feel." 

Empathy and Assertiveness Are Essential

Remembering those words from Maya Angelou can make difficult conversations easier. Instead of getting hung up on exactly what you want to say, empathize and put yourself in the other person's shoes. These conversations can only be successful when we look at the issue from both perspectives.

And just as important as empathy is assertiveness. Rhonda's definition for assertive is to preserve your rights and enforce your boundaries without taking away the rights or disrupting the boundaries of others. Being assertive isn't the same as being aggressive. It's simply being clear, deliberate, and maintaining momentum with your purpose in mind.

How You Say It Matters

Rhonda talked about how communication is not what you said. She gave a great example which I'm sure most readers can relate to:

"You can have all the perfect words. It doesn't matter what you said. What really matters is what the other person heard and thought you said. I wish that my husband would give me a heads up when we are about to have an argument so I can record it. I'd like to record what is said because so many times what ends up happening in our arguments is I'll say but you said X and he'll say I did not X. And I'm 1000% certain that he said it but he doesn't hear that he said it. I would like to be able to go back and listen to say "Am I just hearing that or did he really say that?”

The words are, in fact, a minor component; they are not the most significant piece of the difficult conversation. Focusing too much on the words tends to forget the importance of tone. This is where Rhonda said she gets into trouble:

"I have a very direct style and it comes across as witchy with a b sometimes.”

For those on the passive side, your tone of voice might come across as more meek. For Rhonda, and probably many people like her, it can be an issue. But, the good news is that it's an opportunity to practice empathy. 


Assess Your Relationship

Your relationship is a crucial thing to consider when going into a difficult conversation with someone. What is your relationship with that person? Are they afraid of you? Are they thinking they are getting fired? If a relationship with the person is missing, it will make for a very difficult conversation.

Conversely, if we have a good relationship, then we are much more able to have a difficult conversation because our relationship gives us a foundation and familiarity. We know our intentions are not malicious. Without that, it's easier for things to go downhill.

8 Steps to Make Difficult Conversations Easier

Difficult conversations require preparation, so I want to share some of her tips that you can put into your thought process to ensure those conversations are a success.

1. Be Clear About the Issue

What's the exact purpose of the conversation? You might think this would be a given. Still, it's amazing how often people can "dance around" difficult topics and hint at the problem without ever simply stating with straightforward language precisely what it is. Don't do that. 

If you can't state the problem in one sentence, spend more time preparing. Don't make the conversation more difficult by being ambiguous. That only increases the chance of the conversation going sideways. Be kind, but be clear and direct — don't sabotage your intentions with a lack of focus.


2. Begin With the End in Mind

This tip comes from Dr. Stephen Covey.

In his book, "The 7 Habits of Highly Effective People," Dr. Stephen Covey suggests reverse-engineering the conversation. Begin with the end in mind. What do you want to accomplish by the time the conversation is over? State that goal and structure your communication to accomplish it. Take care to create alignment with the issue, the goal, and the in-between dialogue that connects them.

3. Prepare Your Questions

Whenever you are having a difficult conversation, it's easy to get nervous, talk too much in the wrong direction, and ramble on. Be aware of this and watch yourself. The antidote is to ask questions and engage the other person. Not to mention that effective communication is a two-way street. Have a conversation with people, don't talk at them. Rhonda provides some insight when she says:

"...before you have this difficult conversation, think through your issue, think through with the end in mind, and find at least six questions you can ask that might get you to where you need. You want to keep your questions open-ended.”


4. Manage Your Emotions

Not only do you need to manage your emotions, but you also need to think about what the other person's emotions might be and their response. Even if you think they'll react one way, you need to prepare yourself for anything.

People typically react one of three ways in emotionally charged situations. The first is to blank out. Totally frozen and unsure of what to say. The second is to yell. It's not pleasant, but it happens. And the third is to cry. Usually, this stems from frustration more than sadness.

If they blank out, continue gently guiding things along and engage with them; asking a question can help snap them out of it. If they yell or cry, stay calm and acknowledge their frustrations, emotions, and what they are afraid of. Then, continue the conversation with the end goal in mind. Don't lose your focus or let your momentum be derailed entirely.

5. Be Comfortable With Silence

Difficult conversations are, well, difficult. With that comes a natural tendency to want to get them done as fast as possible. Although you should get to the point and be efficient, don't rush and leave the other person feeling confused and bewildered. As the Depeche Mode song goes, enjoy the silence. Resist the urge to talk every second. Pause. Take a breath. Allow what you're saying to be heard and processed. If you ask a question, wait for a response. Allow them to think and communicate.


6. Preserve the Relationship

Just because a conversation's subject matter is unpleasant doesn't mean that we have to be unpleasant. Even if worse has come to worst and a professional separation is in the works, maintain an aura of dignity and gratitude. People will never forget how you made them feel, so do everything you can to make them feel respected. Balance the negative with the positive. End the conversation with a handshake.

7. Be Predictable and Consistent

This is important for everyone, especially people in supervisory, management, and HR roles. You must be able to have difficult conversations with anybody and everybody. Yes, some people might be easier to have a difficult conversation with than others based on your relationship, their personality, or other factors. But, without exception, favoritism creates conflict.


8. Practice First

Difficult conversations require preparation. Don't wing it or mislead yourself into believing that practicing is unnecessary. It is, and it's the only way to truly enter into the conversation with an empathetic and self-aware mindset. Do you think Christian Bale or any other professional actor shows up to a movie set having not rehearsed their lines? Not a chance. And neither should you. Practice what you're going to say so that you deliver the message you want to be received.