The Art of Acing Difficult Discussions

It breaks my heart that so much is left unsaid in our professional and personal relationships. Too often we'd rather walk away rather than address a hard topic . Here's how to do better.

We are gathered here today to speak on the oft unspeakable: difficult conversations.
This isn’t just a well-timed pre-Thanksgiving post, it’s a call for us, as humans, to show up in our beautifully complex relationships and to move through them in a way that satisfies our desire for more: more clarity, more information, more understanding, more value, more attention, more depth, more needs being met, and more tasting of the marrow of life.

Some people are naturally adept or well practiced at asking for what they need (bless them and their well-adjusted childhoods). But for those of us who weren’t presented with great models for navigating difficult discourse, we may internally overcomplicate the conversation before we even get to it. And, just because it feels so hard, we may choose to avoid it altogether.

Read on to see how to approach difficult discussions and get through them in a way that benefits both parties.

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FOR YEARS I avoided (what I thought would end up as) dicey conversations. Just the mere assumption that the other person would get upset, and that I wouldn’t know how to handle those feelings, led me to avoid many, many conversations.

The result of this was romantic relationships that stalled out and never got “real” enough because we were dancing around conversations that needed to happen. In business, I was more direct, but not necessarily adept at having what most people consider to be the most difficult discussion: asking and advocating for a raise or promotion.

Spoiler alert - I’m now a ninja at both of these and many other scenarios…to such a degree that I imagine my partner, loved ones and managers wouldn’t mind if I was a little *less* willing to show up for a heady conversation as much as I do.

But here we are, so let’s do it.

Photo by Orfeas Green on Unsplash

Why Difficult Conversations Are Necessary (i.e. don’t be a weenie and try to avoid them)

Short answer - we leave too much on the table if we aren’t in the meaty moments of life. If we avoid broaching a topic because we don’t know what the answer on the other end will be, we end up with the artificial intelligence version of human interaction. That’s no way to live life. Humans were not wired for the solely superficial. We are made to come together and stand by each other in a kind of intimacy. Cultivating that intimacy requires us to be, well, intimate. And the unavoidable key to unlocking intimacy is: vulnerability.

Try as we might to avoid laying ourselves bare, we get ABSOLUTELY NOWHERE in life if we cannot activate an ability to be vulnerable. Vulnerability is hard because it goes against our instincts. To be vulnerable means to be capable of being physically or emotionally wounded or open to attack or damage. So, yikes, of course we have deep programming away from being vulnerable, FOR OUR OWN EVOLUTIONARY SAFETY.

Though, for all the card sharks out there, maybe the essence of true vulnerability lies in the way that the game of Contract Bridge uses the term, where “vulnerable” is to be liable to increased penalties but entitled to increased bonuses after winning a game.

Guys, ladies, friends — no, life isn’t a competition but seeking bonuses for a game well played doesn’t seem like the worst approach to living out our days.

Everyone can be a winner, we only have to want to show up and play the game. And to play it in a way where you’re entitled to increased bonuses. And you are. Just by being vulnerable.

It’s through vulnerability that we are rewarded in life: in the form of deeper personal connection, feeling seen, finding soulmates and kindred spirits, gaining validation for just being ourselves. That’s winning if you ask me.

If the harmony of human connection is the end point, then to get there we have to go through the bumpy middle part - which is difficult conversations. And maybe not every situation begets a trying discourse, but you have to be at least ready for it; open to the possibility that at some point you will care about an outcome but you won’t know what it will be until you wade thigh-deep into the No Man’s Land of uncertainty.

And maybe it all works in perfect alignment. But maybe it doesn’t. You just won’t know until you give it a try.

How to Prep for a Difficult Conversation

This is the step that trumps all others: get honest with yourself — is the thing you’re asking or saying rooted in love?

When I was so scared to bring something up with someone else, I started this practice by first centering myself and asking, how can I say this with love? How can love guide me to find the words? That cleared out a lot of ego that seems to gunk up the works.

Ego loves to suck up the air and misdirect important conversations. That shit really won’t help you when it matters. Trust me, you can be strong in love. Actually, you can be an absolute warrior wielding love.

Which brings me to….

How to Approach and Get Through It

Have you cleared out the fear? Ya gotta start by clearing out the fear. (If you’ve been reading this newsletter for a while, you know I love a good exercise in fear-shredding).

If I can be of service to anyone, it’s in sharing the steps that got me through a gauntlet of fear and anxiety. Here’s how:

Center yourself. Breathe in and out. Let your shoulders fall. Then, as you think about any apprehension you have about a certain discussion that needs to be had, ask yourself: What is my fear in this situation? Listen to the answer. It could be gnarly and scary. (My brother will attack me, my boss will belittle me, my sister will make fun of me.) Listen to it, but then let it go.

Then, breathe in and out and ask: What is my truth in this situation?
Even if it’s a whisper you hear from deep inside, listen. It may be the positive reassurance you need to move you closer to the action you need to take.

So, now you know the thing that needs to be said or asked for or shared. Check in again: “is this something I’m saying with love?” With your mind and heart aligned, it might be time to jump in. Now better than ever.

The Why and Why Now

Yes, sure, wait until you’re ready to have the difficult discussion. But life is short. Don’t put off the talks that could bring you closer to what you need and want simply because you’re afraid.

Seek the rewards of stating your needs. Of saying your truth with love.

Seek a relationship where you *hear* someone else’s needs, and they hear yours.

Seek a life where we show up and give just a little more of ourselves for a lot more in return.

Seek the increased bonuses.

Happy holidays.

xx Mary