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How I Navigate Difficult Conversations — And How You Can Too!

The need to have that difficult conversation tends to be pretty heavy and daunting. 

We all know the feeling -- it can be an all-consuming experience leading up to it. 

Either you’ve offended someone or you’ve been offended. 

Maybe there’s some sort of conflict needing to be resolved, or someone has some serious beef for no apparent reason. 

The fact that these kinds of conversations weigh on us proves to me just how much value we humans place on communication. 

Having worked in management for a number of years, one of, if not the most important skill to lead people is communication

I’ve had to learn (the hard way for sure) how to and how not to communicate effectively when it really mattered. 

Many of the principles and tools that I’ve implemented in my own communication style are detailed in the book Crucial Conversations: Tools for Talking When Stakes Are High. Highly, highly recommend. 

Here are 3 key principles to navigate difficult conversations!

Start With You.

Photo by Etty Fidele on Unsplash

Isn’t it just way too easy to point fingers? 

This is why before we enter into a difficult conversation, we must start with yourself. 

What role have you played leading up to this point? Believe me, honesty is the best policy, especially with yourself. 

Have you ever had someone just completely unload on you? Some call that word-vomiting. I call that being rude. Regardless, it’s a clear sign of someone who lacks self reflection. 

Don’t be that person. To start with yourself means you must take some time to really take a step back and reflect. 

What does reflection do? Reflection does the following:

  • Builds empathy for the other

  • Begins to open up an experience 

  • Enables self transformation

I was sitting in my office one morning and got a knock at the door. It was one of the other manager’s on my team. 

For the next five minutes this team member proceeded to vent to me about a situation on one of our teams (a situation I was already handling). 

Have you ever had those moments where someone is talking at you instead of with you? This was one of them. 

After she was done, I was then given marching orders as to how she felt I needed to resolve the situation. 

Was I frustrated? Yup. 

Did I want to throw it back in this person’s face that I had already handled it? Yup. 

Instead, I received it, expressed my gratitude for the comments and took some time to reflect. 

My teammate was out of line, no doubt. However my blowing up would have been too. I first had to check my emotions, get my intentions right and seek to see both sides of the story. 

Once I had, I was able to approach a follow up conversation. 

Starting with yourself is essential to approach conversations knowing that you are in a good place to do so! 

 Seek to Understand Before Being Understood.

Photo by Maria Teneva on Unsplash

Once you’ve made it a point to really get your mind and heart to a place where you can have that difficult conversation, now what?

A key principle to move forward, especially before we come in guns-a-blazing looking to fix things, we must seek first to understand rather than being understood. 

Dr. Stephen F. Covey once said,

“Most people do not listen with the intent to understand; they listen with the intent to reply.”

For most of us we first seek to be understood, selectively hear the other, pick up only on bits and pieces of what another is saying without any effort to step into their shoes. 

This can be very damaging to a relationship -- so what else can we do? 

The authors of Crucial Conversations have four paths to powerful listening that can be remembered by the acronym AMPP:

  1. Ask — extend the invitation for the other to share first. “Would you be willing to share your thoughts regarding…”





  1. Mirror — actively confirming that you recognize the other's feelings. “You seem upset when you speak specifically about..”

  2. Paraphrase -— this is the key trait of active listening. Simply, you relay back to the other what it is that you’ve just heard, and don’t be afraid to follow that up with a “Does that sound right to you?”. 

  3. Prime  — this is for all of those conversations that are going nowhere in a hurry. You’ll from time to time find yourself making no progress. I’ve found that it’s because there is something deeper the other hasn’t yet expressed. I use the good ol’ “call out the elephant in the room” trick. “Based on what I am seeing and hearing from you, it seems like there’s more to the story. Am I wrong to say that?”

Find Resolution Together.

During the beginning of the COVID pandemic, my company had seen a lot of changes, shifting, and just making it up over those first few weeks. The natural by-product of a lot of change very rapidly is fear, hysteria, illogical thinking and irrational decision-making. 

One member of our team was very adamant when sharing thoughts regarding a decision made by upper leadership and even came to the point of potentially walking away from the job because of it. I decided to take the situation head on and seek to understand.

For the first 30 minutes of our phone call, it was pretty heated. 

Both of us went back and forth, doing a lot of talking with really minimal listening. 

Finally, I just said, “Hey, we’re on the same team. I really want to understand what’s at the heart of this for you. I need your help on this.”

It was as if the atmosphere changed. 

The situation was no longer about either of us getting our thoughts out but rather finding common purpose and finding resolution to the problem together. 

Health and human performance coach, Brad Stulberg says, 

In addition to its motivational power, when members in a team share the same purpose, that team transforms into a more effective, cohesive, and higher-performing unit.

Great teams are comprised of members who share a common purpose. 

Same can be said about great relationships. Great relationships are between individuals who pursue a common purpose, together.

The pursuit of said purpose will always be characterized by your ability to effectively communicate with one another. 

The conversation mentioned above became fruitful only when we both took our “critical” hats off and put on our “creative” hats. We were able to see the problem in a different light through communicating around a common goal. 

In Closing

Communication is essential to every aspect of life. It’s our main mode of being in relationship with another. 

With that of course comes the inevitable difficult conversations. When presented with them, apply these 3 key principles and watch your relationships thrive!