How To Make difficult Work Conversations Easy

with Roberta Matuson


Roberta Matuson is a six time author and the president of Matuson Consulting, a firm that helps organizations to attract, hire, and keep the best people. She’s a LinkedIn top voice in management and workplace, a contributor to Forbes and Fast Company, and the author of the book Can we talk?: Seven Principles for Managing Difficult Conversations at Work. This week Roberta was kind enough to share some of her genius principles and help my readers tackle difficult conversations more effectively.

From Actress to Author

Roberta didn’t start out thinking she was going to end up in workplace management, but she did want to be a famous actress. Cut to today, where her corporate successes allow her to be consistently featured on media outlets like LinkedIn Live and the O’Reilly Factor with Bill O’Reilly, where she’s one of the few guests to have come out unscathed. She wasn’t always where she is now though–it wasn’t until she realized that her unique experience could help contribute her skills in different ways that she was inspired to leave the corporate world, step out of her role as head of HR, and take on new opportunities to help more organizations.

The first principle is confidence, and that means having the confidence to speak your truth. Roberta’s found that all too often, when someone is approached with a difficult conversation and they’re not feeling confident, they won’t end up contributing their thoughts. By speaking with confidence, or confidently participating in a difficult conversation, the discussion becomes more successful. 

The next key principle is clarity, because so often people go into these conversations with unclear points, and then the person who’s listening also ends up feeling a lack of clarity on the topic.

The final principle is courage. Everyone knows that it takes a lot of courage to say what’s on your mind, and Roberta has discovered that’s especially true for her female clients, who tend to fear not being liked more than men. 

 Fears Influencing Difficult Conversations

As an executive coach, Roberta has had the opportunity to help many professionals find their voice in difficult conversations. As such, she’s witnessed many of the fears people face when approaching a difficult topic, such as; what if the employee quits, what if they offend someone, what if they offend their boss. Roberta advises these clients to not look at the conversation as a circumstance in which someone can potentially take offense–it’s one where you’re actually helping them know that there’s a problem they can solve with you. 

Tips for Having Difficult Conversations

First, Roberta advises that a person write down what the objective of the conversation is. With that definition, they know exactly what kind of conversation they’re going to have. You should also always make sure that the person you’re speaking with knows the topic and where you’re coming from by asking clarifying questions. These questions can look like, “tell me what you just heard”, “what are you going to do differently as a result of this conversation”, “do you have a clear understanding of what’s going to happen next if you’re unable to fix this.” The person’s answers to these questions can help smooth over any points that need to be reiterated.

Roberta also advised that while it’s a good plan to map out where you’d like a conversation to go, a person should also be able to recognize that things might not go according to plan. Be ready to take a break because, while it can feel like we just want a conversation to be over, dumping all of your thoughts isn’t the best way to deliver a difficult conversation when someone else can’t absorb it. 

Lastly, one of the best practices when having a difficult conversation with someone is to tell them up front, “I’d like to have a conversation with you,” and then go to a place where you can speak openly and in private.

To continue learning more about how to approach difficult conversations effectively, buy Roberta’s book at Amazon, Porchlight, or Barnes & Noble.

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