Having Difficult Conversations with Your Team | Blog | DX Learning Solutions

Having Difficult Conversations with Your Team

Take a moment to think of a tough conversation that you need to have with someone, be it a family member, friend, boss, or co-workerbut you're holding back.  

Hold that thought.  

It's human nature to avoid difficult conversations. On one hand, they're complicated, and often times we worry that having them could make matters worse.

Our immediate instinct is to look for a distraction, but a distraction is not a solution.  

Let's look at some real-life situations.



My husband was seven-years-old when he lost his father. His family never truly grieved the loss together. This caused deep emotional scars that weigh heavily on him.

He's angry with his mother for avoiding talking about it. Yes, as a family, they are not ready to address the elephant in the room. They don't want to hurt each other in the process of bringing up the past. 

My childhood best friend is a Project Manager in a top organization. A few years ago his boss became a sponsor on a new change-management initiative. From the start, the scope and deliverable of the project was a red flag, but no one on the team (including my friend) mustered the courage to speak up. They went with the flow.

Fast forward to the project going live -- things went south. Unaccounted working hours, money, reputation, trust, and morale hit rock-bottom. Above all, my friend lost his promotion and his boss was transferred to a different department.

What is the commonality between these two situations? Being willing to engage in a confronting conversation.



Difficult conversations are no walk in the park. They can leave us feeling anxious, stressed, and desperate for a way out.

The problem, however, is that these conversations are often the most important ones we can have for several reasons. 

Facing up to and engaging in hard talks is one of the best ways we refine the core of who we are, become a better version of ourselves, and avoid living in denial.

It can be hard to confront someone about a touchy or uncomfortable topic due to our need for acceptance.

This is what we call Courtesy Bias.

Courtesy Bias is the tendency to give an opinion that is more socially correct than one's real opinion in order to avoid offending anyone.  

Believe it or not, there are over two million resources available online on how to navigate difficult conversations.

Understanding what we are avoiding and why is a significant first step in the right direction. 



Think back to the prompt from earlier: name a tough conversation that you need to have with someone in your life but you're holding back. 

Apply these questions to your situation: 

  • What is the specific conversation I am avoiding? 

  • Why am I avoiding it? 

  • What excuses am I giving? 

  • What is my deeper fear around having this conversation? 

Take a moment to write down your answers.

Now that you've identified your blocks in entering into this conversation, let's look at some best practices around engaging in it.




"We all know what it's like to stay silent and comfortable instead of voicing what we believe."

-Dr. Brené Brown


The top golden rule for engaging in difficult conversations at work is to focus on the situation, not the person

Pushing with your words is like pushing with your hands: if you push, then you will get pushed back.

However, if you listen with respect, then you are significantly more likely to be heard.

According to Fred Kofman, founder and president of the Conscious Business Center, in order to have a productive confrontational conversation you must go through these seven key steps:


1. Listen

Listen quietly, with no interruption. We must be willing to listen to the other party without interrupting. Focus on hearing their side of the situation first.


2. Ask

Inquire openly with sincerity and curiosity. Try out starting your question with, "Do you mean…" to make sure you've heard the other party accurately.


3. Summarize

Let the other person know that you've heard them and understand their perspective.


4. Validate

Acknowledge that what the other person said is reasonable, even if you have a different interpretation.


5. Express

Share your truth. Share your assessment of the situation, examples, reasoning, goals, and suggestions. Be sure to speak in first person and use "I" statements. Avoid using "you", "we", and "it".


6. Negotiate

Engage creatively and try to find a solution that addresses everyone's concerns. 


7. Commit

Formalize your agreement with a series of commitments and a timeframe (if needed). 


The end goal of every difficult conversation is to understand each other's perspective and find a mutually agreeable solution.

This applies to conversations ranging from confronting your boss to talking with your family about past pains.

Are you ready to have that difficult conversation?

You got this.

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