How to Hold Difficult Conversations

By Marianne Renner, Leadership Coach, Author, Keynote Speaker

Almost daily I talk with leaders about holding difficult conversations.

The reality is we’re faced with these opportunities every day. Things don’t always go as planned. Sometimes, they don’t go at all.

You find yourself too aggressive or too soft. Or you avoid the conversation altogether.

That’s because emotions flair, and fight or flight response kicks in. You lose your logic and ability to reason. You either fight, or you flee.

Think about the last time you were faced with a difficult conversation.

You need to hold a team member accountable or address poor behavior in the workplace.

You’re anticipating an annual performance review. You’re either on the receiving end or delivering.

You say to yourself, “I don’t want to go through that again.” So, you don’t. You have plenty of other tasks to keep you distracted. You don’t seem to get around to having “the talk.”

Meanwhile, the problem grows. It bubbles under the surface so subtly you barely notice.

Then one day things explode. Perhaps the damage can’t be repaired.

OK, you get it. Here’s the good news.  

A carefully thought-out conversation can mean the difference between catastrophic explosion and positive change.

If you follow a few simple steps, you can save aggravation, hurt feelings and potentially permanent damage to important business or personal relationships.

Here are steps you can take to have a productive conversation where both parties walk away satisfied, and the outcome is positive.


#1 Prepare your talk

Preparing for a difficult conversation can be one of the best strategies to preempt defensive behaviors.

Can you remember a past situation that seemed to explode out of nowhere? You had no time to think. You were in the thick of debate before you knew what hit you.

I’ll bet if you examine closely, you’ll realize you knew for weeks that you needed to have “the talk.” You simply avoided it. You let things build.

Take action before the situation gets to that point. Be intentional about having that conversation. Take time to plan what you’re going to say. Anticipate how the other person might react. Be prepared for all possibilities.


#2 Clarify your objective

It might seem obvious that you should go into a conversation knowing what you want. A clear objective, however, often is missing. This is a top reason conversations get off track.

When you go into a conversation with a clearly stated objective, it’s easier to maintain focus and bring the conversation back when it starts to veer off track. Identify your objective in your planning phase, and state it clearly in your conversation right up front.


#3 Diffuse emotions

Sometimes all the planning and clarity in the world aren’t enough to keep defensiveness at bay. When you’re having a tough talk, be on the lookout for emotionally charged reactions. Watch for fight or flight response. We’re all aware of aggressive behavior. But don’t forget the silent treatment is also a type of defensive behavior.

When you see these reactions, pause the conversation. Set your objective aside momentarily. When someone is feeling defensive, it’s almost impossible to make progress toward your original objective.

You’ve got to diffuse emotions. You can do this using a number of approaches. Try to identify something you both agree on. For example, when delivering news to your team member about low performance, you might say, “would you agree that we both want a fair workplace where everyone is held to the same standard?”

You also may want to assure the other party that you have his or her best interest at heart. The goal is to restore trust. When you have it, you can shift focus back to your original objective.


Holding difficult conversations is a skill that takes practice.

It’s well worth the effort to develop this skill. If you do so, you’ll stand out from the crowd. As a business or team leader, you’ll retain your best employees. You’ll have a highly engaged and motivated team.

Your employer will respect you greatly.

Your personal relationships will flourish as well.

Your ability to influence others will skyrocket.

With outcomes like that, you can’t afford not to have this skill in your back pocket.


For more help with difficult conversations, check out my summary on understanding different personality and communication styles. Download the DISC summary here.  

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