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Tricky Conversations


I was just speaking with a guy who’s wife spent $15,000 they don’t have, and this is not the first time.  He’s out of his head frustrated.  His M.O. when upset is to lose it all over whoever upset him and then go dark until he can see straight.  Different than my version, no better or worse really, but just as damning.

On the other hand – I have a history of being one of the biggest passive-aggressive chickens around.  When I’m not mustering better, I robotically try to keep things conflict free, no matter how big a sell out. It’s a deeply wired-in response, like a reflex, and hurts everyone involved.

How do you get when you’re frustrated with someone?

When people mess up with us – whether it’s someone that works for us, our brother, or our wife – yes, we sometimes get upset, and then we have to figure out how to deal and how to go on with them.

Most of us never learned great skills in this area.  So what to do?

People talk with me about this almost every day.

And over the years, by being humbled to my knees by my own mis-steps, and becoming a student of this arena, I’ve learned a thing or two.

Back to this guy with the $15,000 he just found out his wife spent – he was talking to me because this go around he wanted something different than his usual response. He wanted something that would make a difference and also something less harming – for him, and less harming for them together.  Even though in the heat of his disappointment it seemed impossible for the situation to ever change because it looked to him like it’s just the way his wife IS, and ALWAYS HAS BEEN.


But the deepest most radical magic I know comes when we open our mouths to share our feelings with the person we’re upset with, and do it with grace, willing to call our own shit, stand in someone else’s shoes and stand for ourselves, and come closer together.


Whether it’s with our employee, co-worker, brother, or wife.

When you get that real, with grace and grittiness, and with vulnerable self-reflection, something special happens.  It’s tricky and sticky, but works like nothing else.

At the bottom of it you find an unexpected wonder.


How do you go there when you’re just f^&cking upset?

1. Go into the conversation with genuine mystery about how the conversation will go.  If you already believe it’s a foregone conclusion, it will be.

2. Be honest and direct.  Say it all.

3. Let them know where you’re coming from.  If you’re plugged in, say so, but be responsible for conducting yourself well in the conversation.

4. Be in the conversation with grace.  Speak to the best in the person.

5. Remember your truth is not The Truth.  Their truth matters.  And your truth matters.

6. Listen like your life depends on it.  The more open to understanding you are, the more powerful the conversation.

7. Be responsible for your own shit and how you probably have something to do with the situation.

8. Get clear about your requests and make them.  And deeply consider theirs.

9. Be real and connected enough to leave both of you better for having had the conversation.