Why You Must Have That Difficult Conversation – And How To Do It

Marissa Levin
Marissa Levin
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There are four words that, when we hear them, we stop in our tracks because we know they are going to be followed by a lot of other words we may not want to hear. This happens in both our personal and our professional lives. Those four words are…. “WE HAVE TO TALK.”

Did you just feel a shiver run up your spine when you read them? Did they sneak their way off of the screen, and grip your throat a bit?

I don’t know who is stressed out more by these words… the person initiating the conversation, or the person on the receiving end.

If you are the initiator, you know you’ve been carrying around this conversation for a while now. You’ve role-played how it will go, what the reactions will be, and how you are hoping it will end. You’ve determined when and where you should have the conversation. And, you’ve come up with lots of reasons why you shouldn’t have it.

If you are the recipient, first you may try to brace yourself for what’s coming with some mindfulness techniques, like deep breathing, or you may quickly tell yourself it can’t be that bad. Or maybe you will immediately launch into a defensive mode. Or, maybe you’ll say, “this isn’t a good time,” or you’ll run.

Putting all of the emotional baggage aside that accompanies the conversation, here is the one reason you must have this conversation.


When it’s time for a difficult conversation, at least one of three things happen:

1: The person who needs to talk keeps it inside. It grows, and festers, and takes on many additional lives of its own, until the angst or anger associated with the original conversation overtakes the actual topic.

2: The person who needs to talk talks to others. Rather than having the conversation with the person they need to talk with, they seek out advice and support from others, and fuel the issue with input from people that may or may not be understanding the entire story (and are definitely not hearing multiple perspectives).

3: The person seeks out the other person (the target) to have the conversation. And, usually it doesn’t go nearly as badly as they’ve fabricated in their minds. Although, sometimes it does go badly. But when that happens, at least it’s over, and the people can address the elephant in the room.

A Self-Assessment Checklist

How can you prep and move through this conversation with as little drama as possible? Here is a checklist of questions for you to answer prior to having the conversation.

  1. What are your objectives for this conversation?
  2. What do you believe is the other person’s position in this conversation? What reactions are you anticipating?
  3. Based on your history with this person, how effective are they at pushing your buttons, or triggering you? How safe do you feel with them? Based on this information, how can you pre-empt triggers?
  4. How are your feelings about this conversation impacting how you will show up? I remember learning that the mere act of inserting a thermometer into a glass of water to measure the temperature changes the water temperature. Similarly, your disposition in initiating the conversation will impact how the conversation plays out. What is your personal temperature?
  5. How have you contributed to the situation leading up to this point? Have you owned that? Have you expressed that to the other person?
  6. Can you approach this conversation without blame or ego, and focus only on solutions?
  7. How aware are you of your own body language? Can you do a body-language check prior to the conversation to ensure you are not projecting a defensive or offensive message?

Alternative conversation starters

Perhaps you can diffuse the situation with a softer opening. One of these may work:

“I could really use your help with a challenge I am having.”

“I would love your perspective on this situation.”

“Can you please help me to understand something?”

It is also a good idea to schedule the conversation, even if it’s for 15 minutes (although it’s important to not rush, so that nothing goes unsaid or unresolved). This way, both participants are completely prepared, focused, and present. No one feels they have been cornered into a conversation they were not prepared to have. Difficult conversations always flow best when both parties feel safe to have the exchange.

Conversation closers

Alternatively, when the conversation is concluding, both parties should feel that they have had ample time to express, and that they have been heard. Something like this may work:

“I really appreciate you having this conversation with me. Is there anything else you would like to discuss?”

“Are we good now?”

I hope these pointers can take the edge off of your next difficult conversation. It probably won’t be nearly as challenging as you anticipate. And just in case it is, you’ll be fully prepared to manage it from beginning to end.

Good luck!

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