Think Fast Talk Smart: Communication Techniques

Some conversations are uncomfortable, but avoiding them comes with a cost.

You want a more successful career, a more fulfilling relationship, a more meaningful life? What if all that’s standing in your way — are the conversations that you’re avoiding?
“Most things that we want in life are on the other side of a difficult conversation,” says Jenn Wynn, a professor at NYU Stern School of Business and previously the director of education at the Obama Foundation. For nearly 10 years, she has taught a course on difficult conversations that equips people to communicate through discomfort in pursuit of what they want. “Sometimes it's a difficult conversation with a loved one, a colleague, a boss… sometimes it's a difficult conversation with myself,” she says. “Are you going to give up on your biggest dreams because you weren't willing to step out of your comfort zone?”
In this episode of Think Fast, Talk Smart, Wynn and host Matt Abrahams discuss how to build the “hard but worth-it skills” necessary for difficult communication. Whether it's asking for a raise, setting boundaries, or addressing conflict, Wynn’s insights show that the conversations you’re avoiding aren’t just holding you back — they’re keeping you from the life you really want.

To listen to the extended Deep Thinks version of this episode, please visit FasterSmarter.io/premium.

Episode Reference Links:
Connect:

Chapters:

  • (00:00) - Introduction
  • (02:53) - Understanding Difficult Conversations
  • (05:10) - Developing Emotional Intelligence
  • (06:10) - Self-Awareness, Pause, Reframe
  • (08:25) - Common Communication Barriers
  • (10:21) - Listening for Understanding
  • (12:58) - Using AI for Communication
  • (14:50) - Creating Psychological Safety
  • (17:26) - The Final Three Questions
  • (23:57) - Conclusion

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Creators and Guests

Host
Matt Abrahams
Lecturer Stanford University Graduate School of Business | Think Fast Talk Smart podcast host
Guest
Jenn Wynn
Former Director of Education at the Obama Foundation | Professor | Leadership Coach

What is Think Fast Talk Smart: Communication Techniques?

One of the most essential ingredients to success in business and life is effective communication.
Join Matt Abrahams, best-selling author and Strategic Communication lecturer at Stanford Graduate School of Business, as he interviews experts to provide actionable insights that help you communicate with clarity, confidence, and impact. From handling impromptu questions to crafting compelling messages, Matt explores practical strategies for real-world communication challenges.

Whether you’re navigating a high-stakes presentation, perfecting your email tone, or speaking off the cuff, Think Fast, Talk Smart equips you with the tools, techniques, and best practices to express yourself effectively in any situation. Enhance your communication skills to elevate your career and build stronger professional relationships.

Tune in every Tuesday for new episodes. Subscribe now to unlock your potential as a thoughtful, impactful communicator. Learn more and sign up for our eNewsletter at fastersmarter.io.

Matt Abrahams: Often the things
we really want are on the other

side of a difficult conversation.

My name's Matt Abrahams and I
teach strategic communication at

Stanford Graduate School of Business.

Welcome to Think Fast
Talk Smart, the podcast.

Today I'm really looking forward
to speaking with Jennifer Wynn.

Jenn is a professor at NYU Stern
School of Business, where she's

taught a class on difficult
conversations for nearly ten years.

Previously she was the Director of
Education at the Obama Foundation.

Additionally, Jenn hosts The H.I. Note
Podcast and runs a consultancy focused

on organizational transformation,
change leadership and repair.

Welcome, Jenn.

I'm really excited for our conversation.

Thanks for being here.

Jenn Wynn: Thanks for having me, Matt.

I'm excited to be here with you
and the listeners, which include

my executive MBA students.

Matt Abrahams: Yes, absolutely.

Well, shall we get started?

Jenn Wynn: Yes.

Matt Abrahams: So you teach a course on
difficult conversations, and I'm curious

what makes conversations so difficult?

Is it the topic, the
emotions, the circumstances?

Where's the difficulty come from?

Jenn Wynn: I wanna say all of the above,
but at the core it's the emotions.

It's the emotional reactivity.

So, a quick way to think about this, in my
first class of the Difficult Conversations

course that I teach, I ask folks to call
out topics that are difficult for them to

discuss, and while they're calling it out,
I'm typing the list into the slide deck.

And we very quickly, not only fill the
page with topics, but then you come to

see that what's really difficult for one
person is not that difficult for someone

else, and in fact, some people enjoy it.

So a topic like negotiations
will terrify someone.

I don't wanna negotiate my salary or
getting a promotion or a negotiating

fees with a client, and someone else
will say, oh, I love a good negotiation.

Let me take your negotiation on for you.

Or saying No when a team member
or a direct report wants extra

resources, or a loved one asks you
for help, and you've gotta say no.

And it's so interesting because not
only are people really unique, even

idiosyncratic, it shows you that what
makes a conversation difficult is much

less the topic and much more the inner
experience that each person is having.

And so effective communicators, effective
leaders know that they've gotta be

self-aware of that inner experience
that they're having in the moment.

When I say inner experience, I
mean what you're thinking and

feeling, but not saying out loud.

And what that makes you realize is,
if I can be aware in the moment that

I'm triggered, then I can pause.

I can recenter, I can regulate my
nervous system, and that way I'll

be able to choose a better response.

And I say to my students, your
nervous system goes with you into

every single difficult conversation.

So if you can pause and regulate
your nervous system, then you're

gonna be a better version of yourself
at the time when you most need to

be the best version of yourself.

So the implication of all of that is
self-awareness and emotional intelligence

are essential for leading difficult
conversations to productive outcomes.

Matt Abrahams: So we really have
to reflect on our own experience

before we can actually be present
and engage in the conversation.

And I think the point you made
about difficult conversations

aren't the same for everyone, and
in fact, we need to appreciate that.

So it's really appreciating your own
experience and the emotions you're

feeling and finding a way to get
yourself grounded and be centered

and prepared before you go in.

Jenn Wynn: Yes, and open to hearing
and understanding the other person's

inner experience because if I happen
to be the one who loves negotiations,

but I'm sitting across from the person
who's terrified by negotiations,

I need to have the emotional
intelligence to be aware of their

inner state and help them manage that.

And at the end of the day, the goal is for
all members of the dialogue to move away

from emotional reactivity towards choice.

I wanna choose the better, more
strategic path, not the reaction that

came out of an emotional trigger.

It's more choicefulness.

Matt Abrahams: So it sounds to me
like one of the key elements, or

a couple of the key elements, of
managing difficult conversations

first starts with self-awareness.

Being other aware and accepting
doesn't mean agreeing, but accepting.

And it sounds almost like there's
an invitation involved where you're

inviting the other person to share
their inner experience so that you

can meet them and then ultimately
make choices in a choiceful way.

Are there particular strategies or
tactics people can use to help bring

out that information in someone?

Jenn Wynn: Yes.

So we'll start with that self-awareness
piece, since it is the foundation.

I tell my students, if you only
remember one framework from this

entire course, please remember
self-awareness, pause, reframe, okay?

Self-awareness, pause, reframe.

So what does that mean?

In the moment am I aware of my physical
cues, my cognitive and emotional

cues that let me know i'm triggered,
I'm heated up in this moment, right?

So for me, I get a lump in my throat
or like a tightness in my chest.

Some people get, uh,
butterflies in their stomach.

I'm curious, what is it for you, Matt?

Matt Abrahams: So I, I resonate
totally with a tight chest.

When I'm ready for battle or
feel like battles coming I,

my whole chest gets tight.

Jenn Wynn: Yes.

So each one of us think in advance,
what's my tell sign, right?

And once I know that, the moment
I see it, I know I've gotta pause.

And then here's the best thing.

If I know my pause techniques, if I know
what helps me metabolize my hormones,

get that adrenaline out of my system,
really regulate my nervous system,

then I can be back to my centered self.

So a go-to pause technique for me is to
imagine myself with my best friend, Carla.

Then I'm at ease, I'm
centered, and that is our goal.

That we lead these conversations
to a productive outcome, both

for the content, the matter at
hand, and for the relationship.

So that last step, reframe, is where
I actually shift away from viewing

this conversation as a threat to
something I care about, and instead

perceiving it as a learning opportunity.

What good information
can I get out of this?

So self-awareness, pause,
reframe is a framework I always

ask my students to remember.

Matt Abrahams: I really like the taking
the time to check in with yourself.

Both how am I feeling emotionally
but physically and use the

physical as a trigger to help you.

Pausing is wonderful.

I love that you rely on a friend.

I have a place I go to in my mind.

There is a particular tree in Sydney,
Australia that faces the Opera House and

the Harbor Bridge, and when I get worked
up, if I just envision that in what I

felt like when I saw it, it's my place
of zen that really helps calm me down.

And then this notion of reframing from
one of threat to one of learning, one

of collaboration, one of invitation.

One of my colleagues, Michele Gelfand,
likes to say, mind your metaphors, and

the metaphor you bring to the interaction
helps determine how it's going to be.

So if I see it as a learning
opportunity, this difficult conversation

is going to go very differently
than if I see it as a battle.

So I really appreciate that.

Share with us some of the other
tips you have, especially if

there are particular barriers
that get in the way to doing this.

Jenn Wynn: Some of the most
common barriers I see are not

having the conversation at all.

I'd say a second one, not having a goal.

And a third, I'd say not listening enough.

Often when we don't have the conversation,
it's because we assume it will go poorly,

so we give up before we've even started.

But here's the thing.

Most things that we want in
life are on the other side

of a difficult conversation.

Sometimes it's a difficult
conversation with myself.

Sometimes it's a difficult conversation
with a loved one, a colleague, a boss.

But a lot of those things that we
really want and we've been longing

for and haven't gotten yet, are
gonna require us to get to the other

side of a difficult conversation.

So are you just going to give up on your
biggest dreams in life because you weren't

willing to take the time to step outta
your comfort zone and practice a skill?

Because that's the thing.

You know this Matt.

Communication is a set of skills,
learnable, growable skills, and

difficult communication is a set
of hard, but worth it skills.

Matt Abrahams: It is important to remember
that these difficult conversations

are one of many conversations that
we will likely have with these

people or in this environment.

So we're not only trying to come to
a mutually agreed to resolution, in

the short term, for this situation,
but we're setting ourselves up

for the future, and the next one.

You mentioned listening, and
that's a skill that my wife is

still encouraging me to work on.

I'm curious, how do you help your
students to be better listeners

in these difficult conversations?

Jenn Wynn: Yes.

So sometimes the issue is not
listening enough and sometimes it's

not showing that we are listening.

So those are two distinct skill sets.

At the end of the day, I think about
dialogue as the free flow of meaning.

And so if I've done it well,
effective dialogue grows the shared

pool of understanding between us.

I understand how you made meaning
of a situation and you understand

how I made meaning of a situation.

So that means that I've gotta inquire,
I've gotta ask enough questions to

understand how you experienced that,
that client meeting, that argument

my husband and I may have had.

And then once I've listened,
internalized, the meaning you

made, I've gotta paraphrase it back
as a check for my understanding.

A real humble attempt to say, this is my
summary of what I think you experienced.

But is that right?

Fix what I'm missing?

Is it half right and
I miss the other half?

And once we can paraphrase, this is
a skill that, honestly, I think it's

like punching above its weight, right?

After I've taken all this time to really
ask these open, thoughtful questions,

get curious, understand your perspective,
make sure you show the person that

you are internalizing what they said.

And like you said, it's not
agreeing, it's just acknowledging.

And when they finally say yes, that's it.

Then you've grown the shared
pool of understanding, at

least from their perspective.

And then you can go share yours, and
that's where you move into advocacy.

But at the end of the day, the
balance you're looking for is

inquiry, paraphrasing and advocacy.

And inquiry and paraphrasing are
listening skills, both to understand

what the other person experienced and
confirm with them that my understanding

was correct of their experience.

And the advocacy skills,
the talking one, right?

That's essentially a two thirds, one
third ratio, and I don't mean it as

an exact science, but I did have a
student say to me one time, oh, so

that's why my parents said you have
two ears and one mouth for a reason.

A lot more listening and
confirming that I understood you

correctly from your perspective
before I dive into sharing mine,

Matt Abrahams: I like your definition of
listening as seeking shared understanding.

And when you take that approach, it
definitely puts you in a place of being

present, of being humble, because you're
checking, maybe I didn't get it right.

And leveraging, what I think is one
of the most powerful communication

skills, which is paraphrasing
because it does so much for us.

I really appreciate that approach.

I'd like to turn our conversation
to a different topic.

I know you are likely getting similar
questions to me with artificial

intelligence, AI, coming into things.

How do you envision that AI could
actually help us with some of these

tricky communication situations?

Jenn Wynn: Yes, I have seen several of
my students find some really great uses

for AI, so I'll give some examples.

Sometimes I have a student who
wants to work on their tone.

They've received feedback that their
tone is getting in the way of their

message being received, and so they'll
type in what they wanna say and

say, make that tone more friendly,
or make that tone more respectful.

And get a sense for what some other
language, some other word choice might be

to help them still deliver an authentic
message, but in a way that can be heard.

So that's one interesting way.

I think another is coming
up with perspectives that I

haven't considered, right?

Here's the problem I'm dealing with.

What other perspectives could there be?

Or here's my take.

And then recently I had a student
really enjoy the role plays that we

did in class, but not have someone back
in her apartment to role play with.

And she actually asked ChatGPT
to role play with her, uh, which

I thought was such a cool idea.

And I just think at the end of the
day, we have to keep in mind that this

is one perspective based on whatever
data this particular LLM has been

trained on, and not take it as the
final word, but just more options.

Matt Abrahams: Practice for these
situations can be so important,

as with any communication,
and using a tool to do that.

And I really like this idea of
having a tool help you see what

other wording can affect tone
in a way that you might not see.

I like that a lot.

Like me, you host a podcast,
one that I've enjoyed very much.

I'm curious to learn how you balance
your inquiry to challenge your guests

without turning your interviews
into challenging conversations.

In other words, how do you put your
audience at ease enough to have the deep,

meaningful conversations that you have?

Jenn Wynn: So on The H.I. Note
podcast we're talking about how people

healed from some really tough stuff.

You know, childhood trauma, loss
of loved ones, disease, goodness,

toxic relationships, you name it.

And so before I asked them to share about
some of the toughest moments in their

lives, I start by surprising them with
three things that I love about them.

And so this is not in the agenda
that I send them ahead of time.

But when we sit down to chat, I
let them know three elements of who

they are that I absolutely love.

And it's amazing to see how, not only
pleasantly surprised they are, which

is just a nice moment of pure joy and
connection, but also to see how once

they feel seen as a whole person, and
in a strengths based and affirming way,

they become more generous in what they
share and the conversations go deeper.

And I learn such amazing insights because
they've really let down any walls or any

pretense and just shared from the heart.

And it's been a beautiful gift to see
how powerful asset-based framing is, and

I've brought that over into my classes.

So for Difficult Conversations, and for
the other courses I teach, in the very

beginning, in the first session, I'll
ask folks to gather up in trios and do

an exercise that I call at your best.

And so they'll share in trios
times they were at their best

during a difficult conversation.

And then the feedback that they
give one another is strengths based.

So, this action that you took
had a tremendously positive

impact, do that again.

Or, wow, I'm really impressed how
you shifted your mindset right there

in the middle of being triggered and
now I'm gonna go do that as well.

And students say that they not only
feel seen after that exercise, but

that the classroom environment is more
psychologically safe and enables them to

be more brave in the rest of the course.

Matt Abrahams: I love that
as an opening activity.

I'm going to borrow it, if you don't mind,
to have people think about in my course,

a time where they were able to communicate
strategically in a way that was successful

and then to get that positive affirmation.

I really like this idea of
leading with connection.

You sharing the three things that you
really appreciate about the person is

a way of connecting and saying, I see
you, I know you and I respect you.

And that opens up the door to perhaps more
challenging or, or deeper conversations.

Thank you for that.

Well, as you know, as someone
who listens to the podcast, I end

every episode with three questions.

One I make up just for you, and two, I
ask everybody, are you ready for that?

Jenn Wynn: I think so.

Matt Abrahams: Yes, you're gonna do great.

I'm going to ask you the unfair
question that I always get asked, 'cause

I'll be curious about your answer.

So people will often ask me,
what's the one thing I can do

to improve my communication,
as if there is one magic key.

But I'm asking you this question because
I hope it gives you an opportunity to

talk about something that we haven't
talked about, because we've talked

about a lot of really deep, meaningful
communication bits of advice, know your

audience, know yourself, paraphrase.

Is there something that we haven't
covered that you think is important?

Jenn Wynn: Practice.

At the end of the day, the
goal is not perfection.

It doesn't exist.

The goal is continual improvement.

I wanna keep getting better and better.

And so the way to do that, of course, like
any muscle building activity is practice.

And so I really do, not only create
a lot of practice opportunities for

my students in class, but I give
them ideas of how they might continue

practicing after the class is over.

And my suggestion is to make it a
little more challenging each time.

So start with the low
stakes day to day stuff.

When you're chatting with your
roommate, ask a few more questions

than you might have otherwise asked
so that you build that inquiry muscle.

But then when you have a disagreement
with a colleague, if you think, this

might actually make a difference if I
shared this one perspective, try out

stating your intention, sharing your
perspective, and then asking for a greater

understanding on their perspective.

And as we continue to have more and more
repetition, right, as we build in the

reps, we're not only gonna build the
muscle, which feels good, but then it's

gonna be ready for us to flex when the
moment counts, when we're in the most

consequential conversation, we will have
already built up those great question

asking muscles, those great paraphrasing
muscles, those great intention stating

muscles, and so on and so forth.

So practice, practice, practice,
and make it a little more

challenging each time along the way.

Matt Abrahams: And I think
that's absolutely dead on.

We have to practice.

I'll be curious to hear your answer,
who's a communicator you admire and why?

Jenn Wynn: Michelle Obama.

Her authenticity is palpable.

When she's sharing, it's not only real
and true for her and others in the

room, it's the heart of the matter.

She's not being authentic
about things on the fringe.

She's getting to that piece that lands
in the pit of my stomach that I may

not have had the courage to share.

And she has so many great quotes, one
of which is, courage is contagious.

And I feel that in her presence or
when I'm watching a speech of hers.

And then of course her ability to
connect, but she's fantastic at connection

through relatable storytelling and humor.

And I've seen that in her most
casual and impromptu moments

and in her prepared speeches.

It's just a part of who she is.

Matt Abrahams: Courage is contagious.

Really profound actually.

And connection, and
the ability to connect.

Storytelling is a key tool for that.

Alright, what are the first
three ingredients that go into a

successful communication recipe?

Jenn Wynn: Audience, intent
or goal, and listening.

Uh, we've already spoken about the
importance of knowing where the

other person is at and how to meet
them where they are at, right?

Emotionally, during that time of day or in
their schedule, what matters most to them.

Understanding how to create a shared goal,
right, which goes into the second piece.

And then the last piece, you might've
thought it'd be something around

know what your message is, or be
clear on what your message is.

But the reason I think it's listening
is because if I'm really growing

the shared pool of understanding, if
I'm really hearing your perspective

and understanding it to a level that
I didn't understand before, I may

actually have a new idea, right?

I've heard the quote, dialogue
is the birthplace of synergy.

Your information and the way you made
meaning of that information might

create, not just a new perspective within
me, but a new meaning making, a new

understanding of what matters most and
therefore, what I'm most wanna drive home.

So, audience, intent
or goal, and listening.

Matt Abrahams: So audience
and intent and listening.

Jenn, this has been a
fantastic conversation.

You have equipped me, and hopefully
our listeners, with many tools they can

use, and you have certainly increased
our shared understanding and meaning.

Thank you for joining us
and thank you for your time.

Jenn Wynn: Thank you for having me.

This was fun.

Matt Abrahams: Thank you for
joining us for another episode of

Think Fast Talk Smart, the podcast.

To learn more about difficult
conversations listen to episode

22 with David Demarest.

This episode was produced by Ryan Campos,
Katherine Reed, and me, Matt Abrahams,

at the Spotify Studios in New York City.

Our music is from Floyd Wonder.

With special thanks to
Podium Podcast Company.

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