September 22, 2023

How to have a difficult conversation

I've talked with people about how I've lied to them, how I want nothing to do with them, and how I want everything to do with them.

Difficult conversations: where at least one person needs to get sensitive information into the brain of at least one other person. The topics they're about come with a seemingly high chance of rejection. It's easier to just avoid them.

If you can have difficult conversations, you'll be a better communicator. With this move in your bag, you'll be more composed, more likely to reach resolutions, and better positioned to have happy, healthy, and productive relationships.

In this one, we'll go over why you need this move, how to pull it off, and when I've used it.

Why you need this move in your bag

Without it

you [green jacket]

problems [blue jeans]

Without the ability to conduct, initiate, and participate in difficult conversations, you invite problems into your life and can make your relationships fragile.

With it

You can talk about anything when you can conduct, initiate, and participate in difficult conversations. If you can talk about anything, you put yourself in a position to solve anything.

For me

Difficult conversations have been the most important catalyst for personal growth in my adult life. They've allowed me to practice truth-telling and uncovered the richest information about the people I've been in relationships with.

Steps

Step 1: Determine when you should have a difficult conversation

You should have a difficult conversation when there's a need to address sensitive information or unresolved issues that could cause problems in your relationships.

The sensitive part might be a taboo topic like money or sex. Or it could be something vulnerable like your or someone else's emotions. Regardless of the subject, if you find yourself on any side of these situations, you probably need to talk about it:

  • Truth-telling: admitting to a lie, revealing a hidden truth, disclosure necessary for someone else to make a more informed decision
  • Revealing your position: telling someone what you want, how you feel, or what you think
  • Uncovering someone else's position: asking someone what they want, how they feel, or what they think
  • Relationship Gerrymandering: expectation setting, setting boundaries, breaking up
  • Apologizing: Expressing remorse, taking responsibility for your actions, committing to recourse

I've pulled out this move several times in each situation. Starting with truth-telling started a positive feedback loop where other scenarios became easier the more I had difficult conversations.

Step 2: Set the purpose of the conversation

Once you recognize which type of situation you're in, lock in what you hope to accomplish by having this conversation. Knowing where you hope to end up forces you to move intentionally. Moving intentionally in a difficult conversation will clarify your message and increase the chances of achieving your goal.

How to do it:

  • Identify and say in a sentence or two what your purpose of having this conversation is

Step 3: Set your expectations of the conversation

Just because you have a difficult conversation doesn't mean it'll go your way. You can come as correct as possible; you'll still have no control and only some influence over how someone will respond. You should expect to approach the conversation intentionally and live with the results.

Let me tell you how old Jared put this into action. Years ago, I decided to come clean to my closest friends about information I had omitted. I had repressed the truth and avoided radical transparency for so long that I had forgotten the guilt I had around it.

Even back then, I came in with a purpose. I had a script, and I knew my message after the first few conversations. I came in gently and kept the conversation on track, too. But what I did back then that set the tone for future Jared's truth-telling talks was letting go of my expectations about the results.

Guilt had a vice grip on me, I'll admit, but I reasoned that this disclosure may have changed my friends' opinions, upset them, or even made them want nothing to do with me.

Faced with those possibilities, I had those conversations anyway.

Keep your ego off the court, especially when apologizing or telling the truth. Having a difficult conversation or initiating one does not guarantee things will go your way. There's no guarantee of vindication, or that person will like you, that person will forgive you, or that they'll agree with you. Have the conversation and live with the consequences.

How to do it:

  • Repeat to yourself that the process is more important than the outcome

Step 4: Write out your plan

Prepare a plan to make your message potent, protect its integrity, and insulate yourself from anxiety.

Haters will say you can't be genuine and use a plan or a script. But creating a script doesn't mean you're acting. It means you're being intentional about what you want to say.

I've found this to be helpful with remembering facts, like examples of behaviors I've noticed. Still, it's helped me build the courage to say more challenging things. I've talked about boundaries, breakups, and other relationship gerrymandering clearly and calmly only because it started as a plan on paper.

How to do it:

  • At a minimum, write down your goal on paper. Advanced hoopers should get their main points, examples, and other pertinent details on paper, too
  • Relay, don't recite: do not read your script word for word, bar for bar

Step 5: Set the time and date

Setting a time and date won't remove all the anxiety and apprehension surrounding the conversation. But it's the best way to make sure all parties involved are prepared. As soon as you stop it from being "out-of-the-blue," you allow everyone to be intentional about important topics that require it. That means folks get time to prepare what they're going to say. It enables everyone to curate an environment that's private, clear of distractions, and otherwise conducive to communication. It reduces the chances anyone's message becomes muddled with tangential matters. And it reduces the chances that emotional outbursts derail your communication.

How to do it:

  • Find a mutually agreed-upon date, time, and rough duration you'll have this conversation
  • Choose the most interactive communication medium available. That means you should prefer in-person mediums over digital

Step 6: Start difficult conversations gently

Out of all the moving pieces of difficult conversations, none may be more in your control than coming out of the gate gently and compassionately. At the same time, this is the number one way to reduce the chances your conversation ends harshly.

In Plays Well with Others, Eric Barker puts it simply: "if it starts harsh, it's going to end harsh." For romantic relationships, "harsh startup not only predicted the outcome of the conversation, it predicted divorce."

The research is conclusive:

"Starting conversations harshly isn't a "slippery slope" — it's a single heavily greased step. Ninety-six percent of the time. Unless you and I can find a way to revise the laws of probability, you are on your way to a brawl faster than you can say "irreconcilable differences."… So take a deep breath. Use your nicest inside voice. Show some compassion. Raise the issue diplomatically. Your romantic relationship can make a cosmic leap forward just from that one small tweak…"

Starting gently is the most impactful thing you can do, and it's entirely in your control. Don't worry if your conversation partner is mad at you or you think it won't make a difference. You could never fully control how they'd perceive you in the first place, so you might as well be nice.

How to do it:

  • Before you start talking, take a deep breath

Step 7: Play ball

To relay your message smoothly, say what you mean, don't interrupt, and actively listen. A difficult conversation is just a conversation with a tuxedo. It's the same game with bigger stakes. Like any other conversation, stick to the fundamentals.

Saying what you mean is telling the truth. Be gentle, but tell the full truth people need to hear. Don’t tone it down.

Stick to the essence of the script. Stay out of those rabbit holes. Don’t bring up or dwell on stuff that has nothing to do with what you came to talk about.

Strike a balance between being assertive and letting folks get their word in. You're having a conversation, not giving a lecture.

Actively listening means listening to understand, not just to respond. I usually hit the "what I think you're saying is [x]" to show that I'm listening and picking up what my conversation partner is putting down.

How to do it:

  • State your purpose explicitly (come to a mutual understanding): "Hey, I think the goal of this conversation is [x]. What do you think about that? What's your goal?"
  • Lay out the meat and potatoes of your message according to your script
  • Pause often to slow yourself down, give everyone a break, and check for understanding

What to do with your new move

Knowing the steps might not make it much easier to go out and do it. Have a lil courage, and remember your bag is bottomless!