Difficult Conversations: How to Discuss What Matters Most

by Douglas Stone

Sometimes life deals us a blow that we can’t cope with on our own. What constitutes such a blow is different for each of us. It may be something as undermining as rape or as horrifying as war. It may be a physical or mental illness, an addiction, or a profound loss. Or it may be something that would not disturb most other people but does disturb you.

Our Identity Conversation tells us loud and clear that asking for help is not okay — that it is shameful or weak and creates burdens on others.

The paradox is that trying to change someone rarely results in change. On the other hand, engaging someone in a conversation where mutual learning is the goal often results in change.

Why? Because when we set out to try to change someone, we are more likely to argue with and attack their story and less likely to listen. This approach increases the likelihood that they will feel defensive rather than open to learning something new. They are more likely to change if they think we understand them and if they feel heard and respected. They are more likely to change if they feel free not to.

Is this the way Sylvie has gotten results in the past?

Negotiating with yourself to shift your purposes can lower the threshold of how risky the conversation is likely to be and improve the odds of a constructive outcome.

Don’t Hit-and-Run. Often, when we have something important to say, we say it now because now is when it’s causing us frustration. Most of us are thoughtful enough to avoid the most egregious errors of bad timing.

Believing there’s some appropriate time frame for getting over something is just one more way to keep yourself stuck.

One thing you can make of it is that they are as imperfect as you are. No matter how clearly you share how much their drinking hurts you, their forgetfulness aggravates you, or their unresponsiveness saddens you, they may not have the capacity to be different, at least not right now.

We define ourselves in relation to our conflict with others.

The gold standard here is working for mutual understanding. Not mutual agreement, necessarily, but a better understanding of each of your stories, so that you can make informed decisions (alone or together) about what to do next.

We trigger the other person’s Identity Conversation from the outset, and there’s no room in our agenda for their story.

The question is what to do instead. Below, we lay out two powerful guidelines for starting the conversation off in the right direction: (1) begin the conversation from the “Third Story,” and (2) offer an invitation to explore the issues jointly.

Keeping communication open and understanding the feelings and perspectives involved sends an important message that even when we disagree, we care about each other.

Jason has not only acknowledged Jill’s story as an important part of the conversation, but also included his own as part of the process of understanding the problem. And in doing so Jason has succeeded in shifting the purpose of the conversation from arguing toward understanding.

I’ve described the problem in a way we can each accept. Now I want to propose mutual understanding

“Can you help me understand …?” you offer the role of advisor. “Let’s work on how we might… .” invites a partnership. “I wonder whether it’s possible to… .” throws out a challenge, one which offers the other person the potential role of hero.

Sometimes the most genuine thing you can do is share your internal struggle to cast them in a more positive role. You can say something like, “The story I’m telling in my head about what is going on is that you are being inconsiderate. At some level I know that’s unfair to you, and I need you to help me put things in better perspective. I need you to help me understand where you are coming from on this.”

offers them the role of “someone who can help me get my perspective back.”

In a difficult conversation your primary task is not to persuade, impress, trick, outwit, convert, or win over the other person. It is to express what you see and why you see it that way, how you feel, and maybe who you are. Self-knowledge and the belief that what you want to share is important will take you significantly further than eloquence and wit.

To communicate with clarity and power, you must first negotiate yourself into a place where you truly believe that what you want to express is worthy of expression — a belief that your views and feelings are as important as anyone else’s. Period.

If you are sometimes lonely or despondent and never share this with those close to you, then you deny them the chance to come to know a part of you.

But it’s hard to present only this sanitized version of yourself.

A relationship takes hold and grows when both participants experience themselves and the other as being authentic.

Such relationships are both more comfortable (it’s more relaxing to be yourself) and nourishing to the soul

This is unfortunately all too typical of many difficult conversations. We say the least important things, sometimes over and over again, and wonder why the other person doesn’t realize what we really think and how we really feel.

“Have I said what is at the heart of the matter for me? Have I shared what is at stake?”

The gap between “You are playing too much golf” and “I would like to spend more time with you” is just too great.

We’ve all learned that for others to understand us, we need to make what we say clear and simple. Fair enough, as far as it goes. The problem is this: What’s going on in our heads is often a jumble of complex thoughts, feelings, assumptions, and perceptions. When we try to be simple, we often end up being incomplete.

“I’m having a strong reaction here that I’d like to share, and I’m worried about feeling embarrassed if I’m not able to be clear or unemotional at first. I hope if that happens that you’ll bear with me and help me stay with it until I can put it succinctly.”

But presenting your story as the truth — which creates resentment, defensiveness, and leads to arguments — is a wholly avoidable disaster.

the experiences that inform your feelings on this subject.

The key is to communicate your feelings in a way that invites and encourages the recipient to consider new ways of behaving, rather than suggesting they’re a schmuck and it’s too bad there’s nothing they can do about it.

It may be that they are still worried about being blamed, or don’t understand the terminology you’re using.

It’s the one that says, “I can listen and understand what you have to say, and you can listen and understand what I have to say.”

You can’t move the conversation in a more positive direction until the other person feels heard and understood. And they won’t feel heard and understood until you’ve listened.

When the other person becomes highly emotional, listen and acknowledge.

If they level accusations against you, before defending yourself, try to understand their view. Whenever you feel overwhelmed or unsure how to proceed, remember that it is always a good time to listen.

This issue is obviously important to Harpreet. And for that reason, it makes sense that he should be persistent in raising it with Monisha. Many people think that being persistent means asserting your view — in other words, that Harpreet should just repeat himself. But that doesn’t work.

When I say that I love you, what are you thinking?

But simply by listening through the retorts and arguments for the feelings and stories,

Reframing and listening involve leading the conversation in the direction you want it to go.

really do want to know what’s upsetting you, and I want us to find a way to talk about it that doesn’t feel intimidating to me.

Naming the dynamic between you can be enormously helpful in clearing the air.

often the other person is not aware that they are doing something that is upsetting to you.

However, it does take the conversation off the substance, and sometimes, it can escalate tension. So naming the dynamic is probably best thought of as something to try when nothing else has worked.

If you find problem-solving difficult and anxiety producing, it may be because you are focused on persuading them. Those caught in this trap struggle like a fish on a hook, desperately trying to satisfy the seemingly insatiable demands of the other and reach some reasonable agreement on how to move forward. And no wonder. This frame gives the other side total control — until and unless they are satisfied, you must continue to struggle.

Divergent views are often rooted in one or more conflicting assumptions or hypotheses.

Our experience has been that people who understand that persuasion must be a two-way street rarely find themselves in situations like this.

Both the challenge and the spice of relationships is in people’s differences. Occasional frustration is the price of admission.