How To Have Difficult Conversations

Nate Anglin
Oct 31 · 5 min read

We avoid them like the plague, yet, we always have to have them.

Running from difficult conversations isn’t going to help, nor is running into the conversation like a mad hippo.

My best friend used to work for me.

He was working a deal with a foreign company to support engine material for a military aircraft.

We submitted the material for export through the Department of State.

I got a call from the FBI.

They called to inform me they would be visiting my facility the following day.

When the FBI agent showed up, he introduced himself, and his CIA friend. They were kind enough to bring me an FBI notebook.

Sweet guys.

They wanted to speak about our client. He was someone on the Department of States’ “questionable” list, so we could not export the material to him.

The asked me questions about him, and I had to volunteer to hand over the details.

I had to string this person along for months so the agents could continue their “work.”

In the end, we lost money and a TON of time.

I fired my best friend.

I sat him in the conference room and said, you’re fired.

We’ve never spoken since.

My approach to this difficult conversation was flawed, immature, and a reason things ended the way they did.

Here’s why.

The root cause of difficult conversations.

Keith Rosen identifies five reasons confrontation happens in his book Sales Leadership:

  1. Your approach.
  2. The current assumptions you perceive to be the truth.
  3. Your mindset going into the conversation.
  4. Your expectation of the outcome.
  5. Your experiences surrounding the situation, including your past experiences in dealing with similar situations or people, your relationship with that person, or the role they are in.

I can apply this to thousands of examples in my life.

In the earlier story, it was my approach, my mindset, and my expectations of the outcome that made my conversation with my friend so terrible.

Lead difficult conversations with enrollment.

Keith Rosen says it’s about what they want, not about what you want.

What I want for you is to achieve your goals without feeling the immense stress I’ve witnessed in the last few weeks.

We’re all human and have a desire to fulfill our wants, needs, and desires — even people who are naturally grumpy and upset.

The steps to enrollment are easy but take practice.

Six steps of enrollment.

Step 1: Assess the timing of the conversation.

I wanted to talk with you about the situation that happened yesterday that, if we can work through together, would make working together easier and more fun in the future and avoid another stressful situation so you can continue to succeed. Do you have a few minutes now, or are you in the middle of something?

Step 2: Demonstrate support of their goal/s.

What I want for you is to achieve the success and satisfaction you want in your career.

Step 3: State your intention.

During a conversation you had with a team member, I noticed you were upset in how you were replying to her, and I would like to discuss this with you, so it doesn’t impact your performance in the future.

Step 4: Clarify the why.

You have my commitment to work through this with you, so you can get the support you need from your team, without the additional stress and frustration you’ve told me you’re feeling.

Step 5: Confirm engagement.

Are you open to discussing how we can achieve this together?

Step 6: Coach them through the problem.

Learn, ask questions, assess their point of view, define the situation, and coach them on how to overcome their current obstacle for the future.

Following this formula for any difficult conversation will help reduce tension and defensiveness.

Never assume.

As they say, assumptions make an ASS out of U and ME.

When you assume, you’re guessing. It’s one of the reasons that make having difficult conversations so hard.

They’re often assumptions about the other person; what they’re thinking, how they feel, what occurred.

You assume they screwed something up. You assume they didn’t do what you said. You assume they’re mad at you.

Assumptions are bad business.

Don’t assume.

Tame your emotions.

Emotions are dangerous.

They start as a tingle in my big toe, crawl up my spine, and shoot out of my head with a ball of smoke.

Emotions control us.

They control how we behave, how we react, and the decisions we make.

Being an irrational creature, emotions lead us astray.

The reason a difficult conversation turns bad is each person is playing to their emotional self.

We’re a walking pile of emotions.

In difficult conversations, take the emotion out of it.

You started with enrollment now follow it through with less emotion and…

Have empathy and actively listen.

People say we have one mouth and two ears for a reason.

Thanks, Einstein.

I get it.

He’s right.

We need to listen twice as much as we talk.

In a difficult conversation, let the other person speak. Let them express their truth. Listen to their concerns. Navigate them into making the right decision with questions.

The best answers start with a great question.

Listening helps you empathize. It’s hard. Some times people are rude. That’s okay.

They probably have a lot of things going on that you don’t know about.

Take an empathetic approach to difficult situations and see how much more comfortable they get.

Thanks for reading! :) If you want to optimize life’s potential, join me here.

Nate Anglin

Written by

Int'l CEO of Skylink Group, founder of JetFuel Coffee. Thrive: Optimizing Lifes Potential. Join Me →

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