Think Fast Talk Smart: Communication Techniques

Transform how you communicate with tools that make your message stick.

Meetings are where collaboration happens — but too often, scheduling them feels like the biggest barrier to meaningful connection. That’s why Calendly was created: to simplify scheduling and make time for what truly matters — the conversation itself.

In this episode of the Think Fast, Talk Smart Tech Tools miniseries, host Matt Abrahams talks with Calendly’s Vice President of Growth, Darren Chait, about how intentional scheduling leads to better communication, stronger relationships, and more productive meetings. They explore how data-driven insights can improve collaboration, reduce burnout, and help teams make every meeting count.

In addition to insight-packed discussions, this miniseries explores innovative tools that enhance the way we communicate and connect. Whether you want to make your presentations more memorable, craft stories that stick, or connect with your audience on a deeper level, these episodes will help you communicate with greater clarity, confidence, and impact.

Episode Reference Links:

Connect:

Chapters:

  • (00:00) - Introduction
  • (01:12) - Calendly Elevator Pitch
  • (02:47) - The Origin of Calendly
  • (04:44) - The Art of Intentional Scheduling
  • (06:33) - Making Meetings More Effective
  • (07:30) - Favorite Communicator
  • (10:08) - Communication Hack or Tool
  • (12:13) - 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
Darren Chait
VP of Growth at Calendly

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: This Tech Tools miniseries
is brought to you by Prezi, the

presentation tool that makes your ideas
easy to follow, hard to forget, and

faster than ever to create with Prezi AI.

The best investment is in
the tools of one's own trade.

At Think Fast Talk Smart, we are
taking this quote by Benjamin

Franklin, the famous US inventor
and founding father, very seriously.

As you know, our show strives to share
tips and techniques to help you hone and

improve your communication and careers.

These practices and approaches can be
augmented with tools and technology.

I'm Matt Abrahams.

I teach strategic communication at
Stanford Graduate School of Business.

Welcome to this Tech Tools miniseries
of Think Fast Talk Smart, the podcast.

In this multi-part miniseries, we'll
introduce you to tools we use at Think

Fast Talk Smart to help us be better at
our spoken and written communication.

And you'll learn best practices
from the founders who created them.

Taken together, we hope these
communication tools will help you find

new ways to think fast and talk smart.

Hi Darren.

Welcome.

I'm really excited to
have you on the show.

Darren Chait: Likewise.

Thanks, Matt.

Really excited to be here.

Matt Abrahams: So many of us have likely
scheduled a meeting through Calendly.

Some of our listeners might not
know exactly what Calendly is.

Can you share what your product is
using the pitch structure I teach my MBA

students, which is what if you could, so
that, for example, and that's not all.

Darren Chait: What if you could avoid the
back and forth of scheduling, the sharing

availability, navigating time zones, or
even working out who the right person is

to meet for your business, so that you can
schedule faster get the right person in

front of the right team, and ultimately
turn those meetings into revenue,

candidates in the right roles, and a
much more efficient way to engage with

your customers, clients, stakeholders,
partners, candidates, whoever it is

that you meet to get business done.

For example, you can imbed Calendly
on your website, people can come

to you, they can find a time that
works for them, they can even pay you

depending on the service that you use.

Or they may be routed to the right
person if they're looking for a demo,

get them to the right territory manager
or the right person to meet with them.

Or you can look across multiple
schedules to find the group people that

they need to meet with, in many cases.

But that's not all, what if you
could have one platform that not

just allowed the ease of scheduling
like you're used to with Calendly

today, but it also helps you prepare,
engage, and follow up on meetings.

So we've got some advanced AI
solutions coming that allow

you to address preparation,
engagement, and follow-ups as well.

We all know meeting life cycles,
not just about how meetings are

scheduled, but how to make the meetings
successful before, during, and after.

So lots to share there soon as well.

Matt Abrahams: That's really
exciting, just taking out the struggle

of scheduling a meeting, but to
then add onto it, increasing the

likelihood of success sounds great.

Thank you.

So I'm curious to get the
origin story of Calendly.

What led to the creation of the tool?

Darren Chait: Yeah, so our founder
and CEO, Tope Awotona, who is

our CEO today, still in 2013,
he was working in a sales role.

And like many of us who are selling
either with a title that looks like

a salesperson or just in our everyday
professional lives, we all do a lot

of selling, he was spending such a
large part of his day going backwards

and forwards, trying to find the right
time, trying to get the right people on

the calendar by navigating schedules.

And we all know when you're booking a
meeting with a prospect, a candidate,

a partner, an advisor, whoever it is,
you don't wanna lose that momentum.

I don't want to have seven point six
emails, which we know on average it

takes to get a meeting scheduled.

If they're interested in meeting
me, I want to meet them as quick and

as easy and as painlessly as I can.

So that frustrated Tope, it
was hurting his pipelines as

working in software sales.

So he founded Calendly to build a
solution, to build that scheduling link

that would now become a household name.

So that was 2013.

And naturally you add in
all the layers from there.

It's really great for you and I to
be able to schedule seamlessly, but

I actually need a more technical
resource to join this demo, or I wanna

share the load around amongst the four
or five of us that work in a team.

Or I want you to be able to book your
home services appointment via my website

and then actually wanna charge you right
then and there because that's how I

make money as a small business owner.

All of these features and use cases
allowed us to become the scheduling

automation platform that we are today.

The next piece of the puzzle is
very much the meeting itself.

It's an honor to be a part of so many
hundreds of millions of meetings a year,

but being apart in terms of scheduling
is a small piece of the puzzle.

And we know that our customers are
looking to us for more of the lifecycle.

How do we prepare and engage and
follow up on the meetings as well?

And that's where we're
heading as a business.

Matt Abrahams: Thanks for that.

And it's certainly a ripe field, right?

There's a lot that can be done.

I know your firm has conducted
research into meetings.

What are some of the most
interesting and useful results that

you've found from that research?

Darren Chait: We've been talking about
meetings for more than ten years,

and it's an area that anyone who, you
know, has an interest in productivity

in the workplace and the way we work
together thinks about a lot naturally.

We've actually just released
our state of meetings report for

2024, and it's a really good read.

I can, I can pass on a link if you're
interested, but what I found fascinating

was the change in perspective over time.

So we all talk pretty poorly
about meetings and there's lots of

meetings out there about meetings
that should have been emails.

And we all, we don't purport to
want less meetings and meetings

that didn't need to be meetings
and all that sort of sentiment.

But the reality is that meetings
are where we make money.

Meetings are where we align teams,
meetings are where we get work done.

In many roles, especially customer
or externally facing roles, without

meetings, you don't make money,
you don't get any work done.

But the reality is obviously
many meetings are not effective.

Many meetings suck.

They don't achieve those outcomes.

And for the first time in all the
years I've been thinking about this,

that was really clear in the data.

Where respondents, professionals,
the thousands of people we spoke

to, really said quite expressly
that more meetings would be helpful.

They want more meetings.

Eighty-one percent of respondents in
this particular study said that more

productive meetings or more meetings that
were productive, would help with the work,

and fifty-four percent said more meetings
would enhance their productivity at work.

So on one sense, on one side, we are out
there talking about meetings that should

have been emails, these unproductive
days that I spend in meetings.

But then the overwhelming majority
of professionals saying, gimme more.

I need more meetings.

And that's a really interesting
dichotomy to reconcile.

Matt Abrahams: I can certainly
appreciate the need for effective

meetings, and that's really
where it becomes the challenge.

And effective could be who's in the
room, what we're trying to accomplish.

So I'm glad that there's data that
are helping us hone in and figure

out what is desired out of meetings.

Because many of our meetings aren't
as effective as they could have

been and helping people understand
what makes for an effective

meeting, I think is really helpful.

Darren Chait: I used to say
meetings, debate, decision making and

discussion, and we saw that, right?

forty-one percent of respondents
said the external meetings, they're

much more productive when they're
used for direction and goal setting.

A similar proportion said when
they're used for decision making.

That's exactly it.

It's what's the purpose of the meeting?

Why do I need the meeting?

If it's for the right
reasons we all crave it.

We want more of them.

If it's not for the right reasons, if
we're just sharing information, if we're

going in circles without a clear goal
or objective, we don't wanna see it.

That competes with productive work.

Matt Abrahams: Absolutely.

So make meetings useful instead of
competition for getting work done.

Thank you for that.

So Darren, before we end, I'm
asking all of the guests of

this miniseries two questions.

Are you ready for this?

Darren Chait: Let's do it.

Matt Abrahams: Alright.

I'd be very curious, who is a
communicator you admire and why?

Darren Chait: The storyteller
archetype, in my view, are the

best communicators out there.

And I was just thinking then
about who I would describe.

I'll tell you a storyteller
who I really admire.

Brian Chesky, CEO of Airbnb, go and
look up the, when they announced trips,

one of their new features, the way he
tells this story for a prolonged period

of time, had me on the edge of my seat.

And I think it's such a great
example of the importance of

storytelling in everything you
do professionally and personally.

So big fan of his as a
communicator for that reason.

Matt Abrahams: I think storytelling
is a critical skill for getting

lots of information across and
talk about a tool for engagement,

storytelling actually works.

Something that many people don't
think about, germane to what we're

talking about, is you can bring story
into meetings, and in fact, it can

help make meetings more memorable.

So thank you for highlighting that.

Final question.

Beyond your tool, beyond Calendly, what
is one communication hack, tool, or

shortcut that you use to help yourself
be more effective in your communication?

Darren Chait: So this might sound strange
being in the business of meetings, but

asynchronous communication or asynchronous
collaboration is how I'm successful.

So what I mean by that is I
spoke earlier about when you need

a meeting and when you don't.

When I don't need a meeting, I still
need to collaborate with my peers.

And we all know that often we feel
the temptation to just schedule

meetings when it's unnecessary.

So I know you've spoken to the folks
at Loom who I'm a big fan of, but as

a principal in general, being able
to share content in an asynchronous

way, video, audio notes, high
bandwidth ways of sharing too, right?

Rather than just a message or an email,
is really how my team is so effective,

particularly across time zones, remote,
different working styles, and so on.

It's a very strong principle in
the way I work and I collaborate

by using video, audio, and the like
to share messages asynchronously.

Matt Abrahams: I really appreciate
that because that is a super useful

strategy for getting things done and it
allows meetings to serve the function

that meetings should, which is for
creative collaboration, the ability

to iterate and decide and challenge.

It offloads a lot of the things
that we use meetings for.

One of the most important things I think,
that I really wanna highlight that you

said is these are for the interactions
that allow for the meetings to be

effective, and I really appreciate that.

Darren, this has been
a great conversation.

You've given us lots of insights into
how we not only can schedule and plan

for our meetings, but some of the things
that we should be thinking about and

doing when we are actually meeting.

I appreciate your time and
I appreciate the advice.

Darren Chait: Great to chat.

Thanks very much for having me.

Matt Abrahams: Thank you for
joining us for one of our

Communication Tools episodes of
Think Fast Talk Smart, the podcast.

Please be sure to listen to all of
the episodes in this miniseries.

We appreciate Prezi's
sponsorship of these episodes.

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

Our music is from Floyd Wonder.

With special thanks to
Podium Podcast Company.

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