Face It: 5 tips to ease difficult conversations

I’m non-confrontational, so before a difficult conversation you’ll find me curled up in the fetal position under my desk reading a tattered copy of “The 7 habits of highly effective people” and listening to a vintage Tony Robbin’s cassette on my Walkman. If I’m lucky I’ll just fall asleep, miss my tough meeting, and get woken up by the cleaning person when they try to empty my trash.

That being said, we all have to face difficult conversations from time to time and not that many people like them. Having been in enough of them, not by my choice, and having heard enough about others’ techniques, I’ve compiled a few tips to help you (and me) ease the process.

1. End Goal – So many people get into a confrontational meeting, promptly forget the end goal they are trying to accomplish, and the meeting devolves into chest beating and point making. You say, “We really need to talk about the project overruns.” Then Reginald says, “Yeah, well you never answer my emails.” Pretty soon, you are furiously writing a list of nitpicks on the whiteboard and Reginald gets so mad he soccer kicks the paper shredder. It’s better to let some small stuff go and focus on the bigger picture goal.

2. Acknowledge – Even though there are so many black and white thinkers in this world, we are all swimming in a sea of gray. So start every conversation by calmly acknowledging any common ground you have, “Yes, we agree that Biggie Smalls was the greatest rapper of the 90’s”. This can have a disarming effect, which can help when you move into the truly confrontational areas like who was the greatest rapper of all time.

3. Olive Branch – If you know the person well and you find yourself in repeated tough conversations with them, you can consider offering an olive branch of some sort to help lighten the mood. Take them to their favorite restaurant or buy them a cannoli if you know they love pastries. A small offering shows that you come in peace, but there still may be hard conversations ahead.

4. Hit ‘em hard, but softly – It’s strange, but people often react more to tone than content. When you have to hit them hard with some truth, do it very directly, but in a very calm manner like you are talking about your weekend plans. They may surprise you by just agreeing. Or if they disagree, it at least opens the door for some civil discussion. You are probably in a difficult discussion in the first place because the person IS confrontational. So if you go in guns blazing, they will just rear up and attack you back.

5. Respect – Through the entire process, keep in mind your respect for the other person. This will help keep you from saying something you regret and then having to do a bunch of time wasting damage control later. Sure Reginald may be a hothead, but he’s also very skilled and you still want him on your team. Besides, after a cannoli and a cappuccino, you are all friends again.

Hopefully this helps and allows you to navigate your tough conversations with a little bit more grace.

As for me, just writing about this has raised my stress level. I’m going to go curl up under my desk again, chant “synergy” 250 times, and then cry myself to sleep.