How to Have Difficult Conversations

Let me just start out by asking: How many of you are facing difficult
conversations these days? As in: Summoning the nerve to begin a
relationship. Or figuring out how to end one. Or asking for something
you need. Standing up for yourself and saying no. Confronting
disrespectful or hurtful behavior. Disagreeing with the majority in a
group. It could even be the neighbor’s dog keeping you up at
night, and you wonder, Should I talk to them? But will it do any good?
Suddenly you find yourself mired in a cycle of indecision, feeling
that there really is no good choice before you, whether to avoid the
problem or to confront it… And right there you have a common
characteristic of difficult conversations. Should I talk to them? Will
it do any good? In trouble if you do, in trouble if you don’t.

Let’s talk about this. Learning how to have difficult
conversations with less stress and more success. But please note: Less
stress, not complete absence of stress. Even once we’ve developed
healthier habits of communicating, difficult conversations are still
going to feel difficult. We’ll still feel fear and anxiety. But
the fact that we’ve spent the time developing healthy conversation
skills will carry over into an increased sense of confidence in what
we are doing, and an increased sense of focus and calm. Less stress,
more success.

Today, I want to do two main things: Go deeper into the question of
why conversations can be so difficult, and then suggest some
approaches and tools that can help manage the difficulty. Let me also
say that the primary text for my message today is a wonderful book by
Douglas Stone, Bruce Patton, and Sheila Heen called Difficult
Conversations: How to Discuss What Matters Most. Great place to go if
you want to get the full picture.

Let’s start with a case study, which comes from this book.
It’s a conversational exchange between Lori and Leo. Lori and Leo
were at a party thrown by some friends, and Lori was about to reach
for another scoop of ice cream when Leo said. “Lori, why
don’t you lay off the ice cream?” Lori, who struggles with
her weight, shot Leo a nasty look… and later that evening, this is
what they said to each other:

Lori: I really resented it at the party, the way you
treated me in front of our friends.

Leo: The way I treated you? What are you talking

Lori: About the ice cream. You act like you’re my
father or something. You have this need to control me or put me down.

Leo: I wasn’t trying to hurt you. You said you
were on a diet, and I’m just trying to help you stick to it.
You’re so defensive. You hear everything as an attack on you, even
when I’m trying to help.

Lori: Help!? Humiliating me in front of my friends is
your idea of helping?

Leo: You know, I just can’t win with you. If I
say something, you think I am trying to humiliate you, and if I
don’t, you ask me why I let you overeat. I am so sick of this.
Sometimes I wonder if you don’t start these fights on purpose.

That’s what Lori and Leo said to each other, after they got home
from the party. A difficult conversation, right? I should add that
they’ve been married for two years now, and this fight is one
they’ve rehashed in all sorts of ways from the very beginning.
There it is.

But now, what exactly makes this conversation so difficult?

Start with Lori. As her argument makes clear, Lori feels certain that
Leo wanted to control her and put her down. She’s sure that this
was the intention behind what he said. And if that’s his
intention, how can she not explode? He hurt me, so he must have wanted
to hurt me. I feel slighted, so he must have wanted to slight me. And
if that’s what he set out to do, well, buddy, let’s get it on.
Let’s go.

It’s easy to see why Lori is angry. Other people’s intentions
matter. When we evaluate what they’ve said or done, it matters
whether it was said or done with kindness, or accidentally, or with
malice. If the intention was kind, or if it was just an accident,
we’ll go easy on them. But if it was bad-malicious or hateful or
unworthy in some way-of course we’re going to get upset. We’re
going to feel the kind of anger we call righteous.

Funny thing, though, about other people’s intentions: they are
hard to know in truth. They exist in other people’s minds, and
other people’s minds are worlds unto themselves. Black boxes.
Mysteries. There is even an intractable philosophical problem out
there called “the problem of other minds.” I could go on all
day about that. But for us, for now, the implication is clear: to stay
away from mindreading. To humbly accept our human limits.

So put the two together-that other people’s intentions matter, and
that they can be so hard to know-and it leads to the mistake that Lori
made with Leo. Lori invented Leo’s intention behind what he said.
She assumed what it was on the basis of how his words impacted her.
She felt hurt, and on this basis she worked backwards to figure out
what his intention must have been. To hurt her.

It happened automatically, instinctively. Lori made an assumption
about Leo’s intention, and without checking with him to see if it
was a correct, she goes on the attack. And, notice how she assumed the
worst. She’s not the only one. We do this all the time. We assume
the worst. For example, when’s the last time you received an
email, and in it, someone appeared to say something that was critical
of you. Or, they were complaining about something someone else did.
Either way, it sparked anger in you. So in the first instance, you
assume the worst and flame them in reply. Or, in the second instance,
you assume the worst and spread the complaint around without even
trying to find out what really happened and if the complaint was even
justified. Instantly we assume the worst, we react, and suddenly
there’s a war of emails, or the listserve is on fire. Is this what
we want? Is this how we’re going to show mutual respect to each

Assuming the worst: the consequences are so destructive. It’s
definitely the mistake Lori made. She communicates her assumption to
Leo with utter righteous certainty, and of course he feels backed up
against the wall, fighting for his life! Which now takes us to Leo-and
the mistake he made.

Lori tells Leo that he’s trying to control her and put her down,
and Leo’s instant, defensive response is NO I’M NOT. He says,
“I wasn’t trying to hurt you. You said you were on a diet,
and I’m just trying to help you stick to it.” That was the
intention that led him to say at the party, “Lori, why don’t
you lay off the ice cream.”

But as the rest of their exchange suggests, Leo thinks that just
because he had good intentions, Lori should not feel hurt. In fact,
now that he has clarified them, all her hurt feelings should instantly
disappear. They should just vamoose. This is what he thinks. And he
thinks this with certainty, because, to him, the conversation is
really only about one thing: intentions. That’s all it’s
about. Thus his amazement and surprise and dismay when Lori continues
to express her hurt, when she just keeps on. What is the matter with
her? He thus concludes that she takes everything as a personal attack,
that she has an ulterior motive of her own: she just wants to pick a

And now a difficult conversation has just gotten more difficult.
Leo’s role in this is as follows. Leo seems not to realize that
when someone says, “Why were you trying to hurt me?,”
there’s actually two different pieces of information there. One
is, I know what you intended; the other is, I got hurt. Both are very
different, and very real. So if we just focus on clarifying
intentions-if we narrow the scope of the conversation to just
that-we’re going to miss out on the other part entirely, which is
perhaps the most significant part. Absolutely, Leo didn’t intend
to hurt Lori. But that doesn’t take away her feeling of being hurt
which reflects the larger complexities of their relationship: how Leo
tends to embarrass Lori in front of other people, how she’s
frustrated about the way she uses food to comfort and relax herself,
how she’s anxious about whether Leo loves her, how she really
doesn’t know what’s going on inside his head these days….

You know, all Lori wants is for Leo to validate her feelings and not
dismiss them. That’s all she wants. To be heard. But Leo won’t
go the second mile with her. He stops the conversation from going any
deeper by turning a deaf ear to everything else but the issue of
intentions. Lori was wrong about him, his intentions were all good,
and so, Lori, why are we still arguing? Why are you still feeling
upset? What’s the matter with you?

What a mess. But wait-here’s how things could get even messier!
The day after the fight, Lori is feeling anxious and frustrated about
her unresolved argument with Leo. She just can’t sit with these
feelings all by herself. She’s got to talk to someone. So she
calls Leo’s mother, Jane. Jane will listen. Lori feels lucky to
have her as a mother-in-law. So Lori tells her about what happened.
She says, “Leo just doesn’t understand. He doesn’t seem
to care. Sometimes I wonder if he ever listens to what I’m really
trying to say.” That’s what Lori says to Jane, because she
needs someone to validate her and help her know that, even with all
her messy feelings, she’s a person of worth. I mean, who
doesn’t need that? And, this in itself is not a problem. But what
Jane goes ahead and does is. When Lori is done talking, Jane says,
“Honey, I agree with you. Leo was never a good listener. You know
what? Don’t worry about it-I’ll talk to him. I’ll make
things better.” And Jane calls her son on the phone. She says,
“Leo, Lori told me everything that happened last night, and I am
so disappointed in you. I raised you to be a better person than that.
You are just like your father-he was never a good listener either.
Why, let me tell you about the time when….” And on and on.

Do you see how things just got even messier? From bad to really bad?
Suddenly, a two-way conversation between Lori and Leo becomes a
triangle incorporating Jane, in which Jane is an outsider third party
trying to change Lori and Leo’s relationship. Jane’s doing
this does not help Lori in the least, because if real positive change
is ever going to happen, it’s got to come from the principals
involved, either Lori or Leo; third party efforts usually only make
things worse. We see this principle verified in international politics
everyday; and it is verified in personal relationships as well. Jane
plunges into Lori and Leo’s relationship like a bull in a china
shop, and while she thinks she’s helping, what she’s really
doing is disempowering Lori and excusing her from rising up to the
task of true maturity. She’s also blindsiding Leo, giving him yet
another reason for resenting Lori, as well as embroiling him in yet
another triangle-between him, his mom, and his dad. Ever heard that
line before? You are just like your mother… You are just like your
father? Leo thought that the conflict was just between himself and
Lori-but now it has expanded to include the conflict between his mom
and his dad.

You know what I think? I think it’s time to ring the bell from our
drama today, and start over. Relationships can be so challenging-we
just do the best we can, and we just keep on going. I really do
believe that there are moments when the timing’s right, we hit our
stride, and suddenly we are dancing, the music of our relationship
sweeps us up and away. But to get there, we have to remember the bell.
To ring it when mistakes are made, and to try again with a heart full
of forgiveness.

So we ring the bell, and we turn to consider some healthier ways of
managing difficult conversations. Four healthy conversation habits.
Here’s the first one: to share the impact that someone’s
statement has had on you, then inquire about intentions. So, for
example, Lori could have started out her conversation with Leo by
saying something like this: “Leo, you know when you said,
‘Why don’t you lay off the ice cream’? Well, I felt hurt
by that.” That’s what she could have led with. And if she
had, there would have been a greater chance that Leo wouldn’t have
responded with a fierce defensiveness but rather with a simpler,
“Oh, I’m sorry.” He wouldn’t have needed to reach
for armor. He could have then tried to clarify things by saying,
“I was just trying to help you stay on your diet.”

Do you see how this would have gotten the conversation off to a better
start? And now the way is open to inquiring about intentions. Fact is,
we are going to speculate about why people do what they do. We are
going to think up intentions. But the key here is to communicate them
in such a way that the other person understands that we are wanting to
check them out for accuracy, to reality-test them. So Lori might have
said, “I felt embarrassed when you said what you did in front of
our friends. It made me wonder about whether you did it on purpose to
embarrass me or hurt me. Was that your intent?” Hearing this, Leo
might feel misunderstood and upset, but at least he won’t feel
like he’s up against the wall.

This is the first healthy conversation habit: share the impact, then
inquire about intentions. Add to this a second healthy habit: listen
past the accusation to the feelings. So, for example, Leo hears
Lori’s speculation regarding his intentions. It might bug him a
little bit, and at some point he’ll want to clarify where he’s
really coming from. But if he can emphasize listening past the
accusation to the underlying feelings-not to see them as irrelevant
but make them his primary focus-the conversation will definitely be
less stressful and more successful.

So he could have said this to her in response: “Wow, it sounds
like what I said really hurt. I didn’t mean to embarrass you so
badly, but that’s how you ended up feeling. I’m really sorry.
Can you tell me more about why it hurt so badly?” Note especially
that last question: Can you tell me more? Talk about validating. Talk
about helping another person feel worthwhile and real. Can you tell me
more? Also: What does that mean for you? What was that like? What do
you need from me? All questions that refuse to go for an easy fix or
solution; all questions that show that you genuinely care.

And this leads to the third healthy conversation habit: refusing to
triangulate. With regard to Lori and Jane, this is what that would
look like. To Jane, Lori explains what happened, and Jane’s
response is not to convey any messages for her to Leo. Jane does not
promise to make things better. Jane does not play the victim game,
“Ain’t it awful!”, with her. What Jane does instead is
this. Jane becomes a resource person for Lori. She sees her job as
empowering Lori, which means helping her to be strong in her own life
and situation-helping her come to come clarity about what she needs to
do next. So Jane asks Lori some thought-provoking questions about what
happened with Leo; Jane asks her, “Why do you think Leo might
have responded so negatively when you said….” Or Jane asks,
“What did that look like, Leo not listening to you?”
“What do you think your next best step here is?” In short,
Jane is not going to tell Lori what to do; she is not going to solve
things for Lori. Instead, she is going to help Lori take
responsibility for herself and help her solve it for herself.

I call that a true blessing. I call that heaven. We need people like
this in our lives. We need to be this kind of person to each other
here at UUCA. Not fighting each other’s battles, but encouraging
each other to live life with strength and courage and maturity. The
problem is not going to a third person to want to talk things out. The
problem is wanting that third person to fix it for you, or that third
person thinking that your problem is now his or her problem.
Doesn’t each of us have enough challenges on our plates, without
taking on everyone else’s? The best we can do, when someone shares
a relationship problem with us, is to help them make their own best
decision and to encourage them to do it. This is the blessing we need
from each other. This is it.

Finally, a fourth and last healthy conversation habit, and it’s
the most basic one of all. It’s this: take a curiosity stance
instead of a certainty stance. Go from certainty to curiosity. Go from
asking “How could they do that or say that!?” to “I
wonder what information they have that I don’t?” Go from,
“They are absolutely WRONG!” to “How might they be
seeing the world such that their view makes sense?”

You see, what makes conversations so difficult, in the most basic of
ways, is that we are so certain that the other person is the problem.
We are so certain of that! And, of course, they dwell in their own
sense of certainty, about us! But in the midst of all of this
certainty, something precious is lost. What is lost is sheer beautiful
wonder at the fact that each of us represents a world of experience
and understanding. What is lost is the appreciation that we are each
unique, we are each different, we each carry with us myriad
experiences and scars and strengths, we each notice different things
and access different kinds of information. We are not so different
that we cannot find common ground to stand on. We absolutely can. But
we are different enough. Even people who have lived together for
years. Different enough that it’s still crucial, always crucial,
to take a curiosity stance in our relationships, to resist taking
people for granted, to expect surprises, to expect a point of view you
hadn’t thought of before. Willingness to receive each other like
honored guests into the homes of our hearts.

Let’s stop taking each other for granted. Let’s give up
certainty, and embrace curiosity instead. Amen.


Douglas Stone, Bruce Patton, and Sheila Heen, Difficult
Conversations: How to Discuss What Matters Most.

Gary and Joy Lundberg, I Don’t Have to Make Everything All
Better: Six Practical Principles That Empower Others to Solve Their
own Problems While Enriching Your Relationships.

Ronald W. Richardson, Creating a Healthier Church: Family Systems
Theory, Leadership, and Congregational Life.