[@ChrisWillx] The Best Way to Deliver Bad News

Link: https://youtu.be/VlJtU4MFbYc

Duration: 11 min

Short Summary

This episode examines the critical distinction between kindness and niceness, arguing that true kindness requires telling people hard truths rather than offering comfortable pleasantries. The host provides practical frameworks for delivering difficult news effectively, including why saying the hard part first and using "labels" before bad news leads to better outcomes than softening the blow. The episode also explores how uncertainty creates psychological pain, with insights drawn from observing courtroom dynamics and the experience of delivering hard truths with integrity.

Key Quotes

1. "Kindness says, "I care enough about you to tell you the truth. Because I care about you, I need to give you this this really hard news"" (00:00:37)
2. "the word but has a way of deleting everything that came before it" (00:00:23)
3. "the open loop is where the most pain is" (00:00:09)
4. "you have to learn the art of disappointing people. In other words, telling them sometimes what they need to hear, not what they want to hear" (00:00:45)
5. "when you're able to break up with somebody and not leave them guessing why or you need to fire somebody, whatever the hard news is, and not leave them guessing why, that is you acting in alignment with integrity" (00:00:43)

Detailed Summary

The Art of Delivering Hard Truths

This episode explores the crucial difference between being kind and being nice, arguing that true kindness means telling people what they need to hear rather than what they want to hear. The host provides practical frameworks for delivering bad news effectively, emphasizing that leading with the hard truth upfront—rather than burying it under pleasantries—creates better outcomes in difficult conversations.

Key Communication Principles

• Lead with the negative: When delivering bad news (breakups, firings, rejections), state the hard part first rather than cushioning it with compliments. The word "but" deletes everything before it, so starting with positives then pivoting to negatives weakens the message.

• Recommended structure for declining: Say "no" first, then add gratitude ("Thank you for inviting me"), then finish with kindness ("I hope you have a great time"). The "compliment sandwich" is described as "a little hard to chew."

• Use labels and pause: Before delivering difficult news, signal what's coming with phrases like "This is going to be hard news" or "I need to have a hard conversation with you," then pause to let the other person process.

The Psychology of Uncertainty

• The open loop—uncertainty—is where the most psychological pain exists. Parents of missing children consistently say "we just want to know," demonstrating that closing the loop provides relief even in tragic outcomes.

• Approaching difficult conversations is like a cold plunge or cold shower: there's initial shock and discomfort, but clarity comes after pushing through the beginning.

• Increasing your capacity to hold others' emotions while maintaining self-control and breathing through discomfort leads to better outcomes in hard conversations.

Leadership and Personal Growth

• To be a great leader or good person, you must learn the art of disappointing people. Delivering hard news without leaving people guessing is acting in alignment with integrity and values—transforming from "nice guy" to "good man."

• The speaker grew up in courtrooms and depositions, witnessing extensive emotional fighting, yelling, and adversarial tactics between parties—shaping their understanding of how people handle difficult revelations.

Tangent: Fiber and Nutrition

• A brief mention that 95% of people don't get enough fiber, not from carelessness but because hitting daily fiber targets through food alone is genuinely difficult. This appears to be either a sponsor segment or an aside, not central to the episode's main theme.

Full Transcript

Show transcript

What about when it comes to delivering
bad news to people?
>> It's a required
life lesson. Like there's it's
impossible to not get around that and
people get really uncomfortable with it.
And usually it's because they're feeling
other people's feelings for them. Like
that I I don't want to say that because
that's not nice. Like they feel like
they have to be nice. But the the real
takeaway is being choosing to be kind,
right? Nice says it's focus all on the
the surface, the pleasantries. I can't
say that. I can't tell you the truth,
Chris. That's not nice. All right.
Kindness says, "I care enough about you
to tell you the truth. Because I care
about you, I need to give you this this
really hard news of what it's going to
this is what it's going to be." And you
can use labels simple as what we just
talked about a minute ago. This is going
to be some hard news. You're not going
to like what I have to say. M give them
a moment and then deliver the news. But
what you can't do is twist a knife where
you start to blame them first, right? If
you need to give bad news, like imagine
if I was just going to break up with you
right now, the worst thing to do about
it is all of a sudden go,
you know, I just think you're so great,
uh, Chris, and I've really enjoyed a lot
of time. We start talking in past tense
as if like what do you
>> I was enjoying that stuff.
>> Yeah. Yeah. just keep just keep going.
>> Um
>> to where you know you're not you're not
being straight up and being honest.
>> And often that's
>> sometimes the kindest thing you can do
is be as direct as you can be when it
comes to sad news.
>> Let's say that you need to break up with
a partner and you're feeling super
nervous about it. How would you guide
that person through the conversation? M
when I would use a label that means
rather than and this is assuming you set
aside time and you're not trying to do
it through a text message or you know
while you're
>> apparently that's go now that's looked
down on to do it over text.
>> Yeah. Yeah. It's probably not a good
idea or you're doing it in the middle of
you know a movie or something. Let's
assume you've already put good time
around this to have a good conversation.
It's to say, "I need to have a hard
conversation with you."
And then you need the first words out of
your mouth need to be.
This isn't a relationship that I can see
myself continuing in. Like, you see how
all of a sudden I'm getting right to the
point rather than saying, "I need to
have something hard. You've just been
great." And you know, it's not you, it's
me, and you know, we just been we've had
all these memories. Yeah. Yeah. Exactly.
instead of all that, get right to the
point and it's it's much easier. People
can take
bad news. It's going to have a harder
impact, but the rest of it is going to
be a whole lot better for you rather
than trying to sound nice and be like, I
don't want to upset it's all me. It's
not it's not you at all. Even though
that's softer in the moment, that
long-term impact is going to be a whole
lot worse because because you weren't
really being
>> honest
>> with me. And so even if you were need to
fire somebody, bring them in,
this news is probably going to shock
you. I need to let you go. And that's
when you get to say, I've enjoyed having
you as a a person. You've done great
with the company. Or maybe it's in a
relationship. I I I need to be out of
this relationship. I need to move on.
This is relationship isn't working for
me. Whatever it is. And that's where you
get to say, I've
I've learned a lot from you. I've
learned and whatever it is, the nice
stuff, but don't start with the
pleasantries and then end with the hard.
I think Chris has another one which is
if you're saying that you can't go to an
event, say I can't go
>> or I can't make it.
>> Yeah.
>> First,
>> right?
>> Don't say things have got so hard
recently and this chaos came up and I've
got this thing and then that at the end.
like just
>> don't bury the [ __ ] lead, dude.
>> Yeah.
>> Put it up top.
>> I very much uh align with that. So, what
I I teach is you start with the no
first. Most people start with the the
thanks first. They start with the
gratitude. They go, "Thank you so much.
I'd love to, but I can't."
>> Um and but the word but has a way of
deleting everything that came before it.
>> Like, I love you, but
>> you're crazy. You know, whatever.
>> That might be true. Yeah. Those things
might be true. Sure. Sure they can. Um,
however,
>> yeah, you want to start with the no
first. So,
>> I can't period. Then the gratitude.
Thank you so much for inviting me. Then
add in some um kindness. I'm sure it's
going to be a great time. Hope you have
a wonderful time. Knock yourselves out.
Whatever it is, but don't don't that
compliment sandwich
is a little hard to chew. Dude, I've got
a [ __ ] fantasy going on in my head of
me, you, Chris Voss, and James Sexon
doing an episode together. I'm going to
try and make that [ __ ] happen before the
end of the year. We probably could.
>> I think that would be straight fire. I
think that would be so much [ __ ] fun.
>> And I put something in the middle of the
table that's remotely valuable or that
most pe most of you guys want. I'm like,
"Hey, negotiate over this."
>> Exactly.
>> See, it's like a gladiatorial fight to
the death.
>> Yeah. Exactly.
>> And somebody somebody gets to [ __ ] I
don't know. I don't know what you get.
Um, so you're having a difficult
conversation, you're firing a member of
staff or you're breaking up with
somebody or something similar.
>> Yeah.
>> And during that conversation,
the emotions begin to come up.
>> And there is always this temptation to
even bail out of the conversation.
>> So like poly ejecty to
>> you see that somebody begins to get
upset and then the employee comes into
work tomorrow and you go, I thought you
were firing them.
>> Yeah. Well, exactly. What about that?
Because I think that a lot of people
enter into conversations with the
intention of doing the thing.
>> Mhm.
>> And leave a conversation having had this
weird spaghetti junction mess. Do you
know what I mean? Like when people have
difficult conversations, often they do
not they do not finish what they meant
to start.
>> Yeah.
>> How would you navigate through that?
Okay. It's to me it's like people have
no problem 3 minutes in a cold plunge
but give them two seconds having to be
honest with somebody in a conversation
terrifies them.
>> It's like okay think of it as like a
cold plunge. You start it and at the
beginning what is it? You're trying to
catch your breath. You're trying I can't
do this and then all of a sudden what
you have some clarity and you realize I
can do this and you realize your body's
going through this and there will be an
end to it. Same way in difficult
conversation. Yeah, it's going to be a
splash. I they have I have what I teach
is cold cold shower conversations as as
example of those of like it's gonna it's
going to be a shock to the system at the
beginning, but we're going to see our
way out of it to where you you start to
have the hard words. You've already said
I we need to break up. This relationship
isn't for me or I need to let you go.
>> Whatever it is, you say the hard news
and then you realize, okay, I did it.
like, okay, I I had I said the thing and
now we can have a lot more clarity. Now
you've kind of gotten over. It's way
easier to crest the mountain when you
just like go right up and then it gets
down. It's when you have a slow go up
>> way. I haven't got there yet. I haven't
done it yet. There's still time for me
to avoid this mountain.
>> Exactly. Exactly. And so it's it's just
like that. So you find ways for me in my
world as an attorney.
I mean, I grew up in courtrooms and
depositions and watching this, so I've
seen a lot of emotional
fighting and yelling and all sorts of
hard tactics against each other. Super
adversarial. I've seen a lot of fights
of arguments.
>> Don't put me in a ring. I'm not I won't
be any good in uh with boxing gloves.
Sean Strickland's going to eat you
alive.
>> Oh, no. No doubt. I' I'd bail out.
That's why I'd bail out.
But whenever you increase your capacity
to hold other people's emotion,
meaning you can feel all your feelings
without me holding them
>> and I know that I'm in control of myself
and I'm going to continue to breathing
through it and I'm not going to be
holding what you're presenting, the
better it gets. Like the more I realize
that
disappointment is part of the game. like
to be a great leader, to be a great um
to be a good person in my world, you
have to learn the art of disappointing
people. In other words, telling them
sometimes what they need to hear, not
what they want to hear.
Makes me think about when the parents of
missing children go on the news,
what is it that they always say? We just
want to know.
>> Yeah.
>> We just want to know. Because the open
loop is the worst thing.
>> Yeah,
>> the open loop is where the most pain is.
And it I'm sure that no parent would say
this, but logically it kind of makes
sense that
>> Yeah.
>> finding the child dead in some ways
would be emotionally preferable to
living for decades in the uncertainty.
>> Mhm.
>> And I mean, no parents ever going to
come out and say that obviously and they
actually probably don't want that. But
you understand what I mean. closing
closing that loop is exactly what people
want, even though it's what your body is
telling you absolutely not to do.
>> Mhm.
>> So, when you're able to break up with
somebody and not leave them guessing why
or you need to fire somebody, whatever
the hard news is, and not leave them
guessing why,
that is you acting in alignment with
integrity. That's you acting in
alignment with your values. It's it's
you going from nice guy to a good man. A
quick aside, there is a stat that
genuinely surprised me when I first
heard it. 95% of people don't get enough
fiber. Not because they're being
careless, but because hitting your daily
fiber target through food alone is
actually quite hard. But that's why
Momentus built Fiber Plus. See, fiber
isn't just a digestion thing. It's the
foundation of your gut health, which
drives how well you absorb nutrients,
how stable your energy is, and how
quickly you recover. If your gut isn't
dialed in, everything else that you're
doing is working at a fraction of its
potential. Fiber Plus is a threein-one
formula built to address digestion, gut
barrier strength, and blood sugar
stability all at once. And this cinnamon
flavor is unreal. You might think,
fiber, wow, I bet that tastes great.
Well, yeah, actually it does. Doubters.
Uh, I really enjoyed this. Best of all,
Momentous offers a 30-day money back
guarantee. So, if you're not sure, you
can buy Fiber Plus. Try it for 29 days.
If you don't love it, they'll just give
you your money back. and they ship
internationally. Right now, you can get
up to 35% off your first subscription
and that 30-day money back guarantee by
going to the link in the description
below or heading to
livemus.com/modernwisdom
and using the code modernwisdom at
checkout. That's lie
mus.com/modernwisdom
and modern wisdom
at checkout. Congratulations, you made
it to the end of a clip and the full
length episode is available right here.