Difficult conversations: how to start

How to start a difficult conversation

I’ve got a difficult topic today. I don’t know where to start.

That’s right! We all know some conversations are hard to have. Rivers of ink have been spilled over the topic of difficult conversations

Today I want to cover how to start a conversation, in the first place. No, I don’t mean that. Not the starter. I don’t want to put words in your mouth.

My problem is, sometimes I sense somebody has something important to say, something on their heart and he or she never speaks about it. I know something is boiling up. Who’s in charge of starting the conversation?

I call this the eyebrow raise dilemma.

The eyebrow raise dilemma

Let’s try some role play. “Is there anything on your mind you’d like to share?” “Uh, nothing.” “Are you sure?” “Yes, nothing at all”. It’s not gonna work.

Option two. “I have the impression something is worrying you. Do you want to talk about it?” “Maybe. Not now.” “If you want to talk about it, you can count on me.” And we just killed it. They are never gonna come back.

Option three. And this applies when somebody actually says something (which is not uncommon). They throws a hint, but then they never share the details. Possibly they mention it repeatedly, always without going into the details. In this case you can see a metaphoric eyebrow raising. When you ask them: “but it’s something difficult to talk about.”

It’s not always a good idea to offer to talk. Because. This stuff is usually very personal, very sensitive, so there’s a chance that you make the offer when it’s not a good time, and the person won’t find the strength to talk about it again.

This also explains why not many people actually check on each other, by their initiative, because most of the time the offer to talk was declined before. So they just gave up. And then there are some people that are just too shy to ask.

Let’s try to flip the situation. The other option is for the person that who has something to say to talk first. Let’s do some role play again. “Hey, I have something to tell you.” or “Can we talk?” And they reply: “What’s up?” “Well you know there is this thing on my mind, I was thinking that…” “Yeah! You know. “I also went through a similar experience and aree-aree-ada” so they monopolize the conversation.

I’m not talking about of those who say everything crosses their mind. They just want attention.

People don’t start difficult conversations

People don’t start difficult conversations, because if the person is not very close then, why they should tell them. But if the person is very close then they are afraid to hurt their feeling or, even worse, that they will appear as weak or they disappoint them. We know that’s never gonna happen. But they don’t know that.

It’s an eyebrow raise dilemma because we need to read the person’s mind from their slight movement on their facial expression, and you know this in not anybody’s skill.

Another way that something can go wrong in a delicate conversation: the other person misuse what you say to them. For example when, I was younger, I know it’s hard to believe, I confided to a friend, supposedly friend, that I didn’t appreciate the way I was treated by somebody. But this wasn’t the problem because I could have handled the other person. Probably not. But I should have. The problem is that I wanted to express to my alleged friend, that he enabled the other person to misbehave around me. I was not blaming him but I was raising the point: “please let me handle the other person because if you are in the middle it makes everything harder for me”. Some time later, say, one month later, it happened again end I called them out both, and then in private I said to my friend: “Hey, I warned you about this. What the heck are you doing? As a friend, I was not asking you to intervene, but at least don’t enable bad behavior”. He argued back he can’t understand what I’m feeling in a given moment just from the raise of an eyebrow.

See? There are 2 lessons, here. One is boundaries, but we leave it for other videos.

The other is that being the one who speaks first, does not always work.

It’s hard to find the person to listen to you when there’s something on your heart.

So, I believe if we know better, we should start the conversation with somebody we love who’s going through something. Because for them it’s very, very hard to start the conversation, because it’s personal, it involves feeling, not good ones, they don’t want to hurt your feelings.

I think if I’m at the other end, It’s really my job to make them talk. More often than not, when somebody is so worried to make it clear there’s something they need help with, but they don’t ask, it’s something that needs professional attention, such as medical, financial, mental, such as depression, which we, as friends or relative, can do little about, except to encourage them to address the matter.

I confess I don’t have the answer as a friend, as to what a friend is supposed to do in this case. At both ends. As a coach, I can do a lot about it. But the person have to hire me and then it’s a different relationship. It’s friendly, it’s open, but it’s confidential, and possibly there is no conflict of interest, like a common friend.

But  I genuinely don’t have a blanket statement advice I can give to friends as to what to do. I can coach on a case by case basis.