How to: Have a Difficult Conversation

Let’s talk about a high stress environment with strong-willed individuals. No, not last week’s episode of Keeping Up with the Kardashians. I am talking about life at the Big 4. In this pressure-filled arena, there is going to be conflict. Navigating challenging situations is a critical skill for long-term success.

Below are tips for having a difficult conversation.

Eat the elephant

If you are anything like me, your tendency is to delay/put off having a difficult conversation.

But, the best way to eat an elephant is one bite at a time.

Therefore, take the first step. Swallow your pride. Schedule the meeting. 

Send a calendar invitation

The only thing people dislike more than having a difficult conversation, is having that conversation sprung on them. 

Consider sending a calendar invitation. This allows both sides to prepare for the conversation. It also sets the tone that you are taking the conversation serious.

Don’t gossip

Hard conversations are often fertile ground for gossip.  “Can you believe he did ________?”

However, gossip never helps a challenging situation.

In the words of cowboy/humorist, Will Rogers: Live in such a way that you would not be ashamed to sell your parrot to the town gossip

Note: That is a great quote, but an even better job title. Why waste time at the Big 4 when you could become a cowboy/humorist? I digress.

Be skeptical of yourself

Seek to understand the other person’s perspective and be skeptical of your own.

For instance, you may ask a trusted mentor for advice on how to navigate the situation.  Invite your mentor to challenge your viewpoint.

Take the emotion out of it. 

Slow down. 

Be factual.

Seek to understand.

Consider inviting a non-biased third party to the conversation.

Set clear expectations for follow up

Challenging situations are not always (or even usually) resolved with one meeting. 

In other words, sometimes it is good to step back and live to fight another day.

But…don’t let yourself off the hook.  Set clear expectations of the timing and content of a follow-up meeting. 

In conclusion, eat the elephant/schedule the meeting, but then proceed with caution.

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