How to Have a Difficult Conversations?

6 steps to make difficult conversations easier.

One of the things I failed at often in life early on was having difficult conversations.

I was never good at them. I always led with emotion, and the outcome was usually far from positive.

I would wait until I was good and mad about something and then unload all my frustrations at once.

I look back and cringe at these moments.

These failures were my basis for a recent Coffee with Champions workshop where the main question was:

“What are the best practices for having difficult conversations?”

Through 30+ years of leadership, I’ve learned a lot about how to talk to people. There are many different solutions to difficult conversations, but here is my personal go-to list.

Here are 6 things I do to make a difficult conversation easier.

1. Interview me first.

The first step is an investigation of myself. I need to confirm that there is an issue that needs to be addressed.

I need to make sure that I’m not just being emotional or offended. Here are some good questions.

1. How do I see the situation? How do THEY see it?

2. What impact has this had on me? What was THEIR intention?

3. What am I feeling about this?

4. Is this threatening my identity of who I am (boss, leader, etc)?

5. What do I hope to accomplish?

6. Do I want to prove a point or change the person?

7. Can I affect the problem by changing my own contributions?

8. Will there be any harm if I let it go?

2. Set the stage as soon as possible

Most problems do not get better with time. They just fester.

I need to set a private time to meet with the person as soon as possible.

3. Be Clear and Direct

Don’t beat around the bush. Tell them what the specific problem is. Do not exaggerate it; just give them the facts as I see them. Share the impact of their behavior.

4. Accept Blame

I’m not perfect, so I probably had a hand to play in this. Maybe my expectations were not clear, or perhaps I’ve let something go on too long.

5. Look for a Win-Win

There’s no need to argue here. I’ll ask questions to better understand what was going on. I’ll convey that we are in this together. Maybe there are some non-negotiables I need to get out on the table politely. What’s the best solution here?

6. Agree on a positive path forward

I want to wrap up with the agreed path forward. I want the ending to be positive, hopeful, and complimentary. I want us to be on the same page.

Quick Tips

• It’s easier if you’ve built trust with the other person. I’m always trying to build up my “trust accounts,” knowing that down the road, I will have to make a “withdrawal” in the form of a difficult conversation.

• Always assume positive intent towards the other person. You never know what was going on in their world.

• Typically, shorter conversations are better. The longer it drags on, the more chance we have of saying something stupid that the other person takes the wrong way.

Till next time, be a force for good.

- Lance

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