239. Tech Tools: How Smarter Scheduling Leads to Stronger Communication

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 https://www.fastersmarter.io/ Tech Tools miniseries, host Matt Abrahams talks with Calendly’s Vice President of Growth, Darren Chait https://www.fastersmarter.io/guests/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: Darren Chait https://www.fastersmarter.io/guests/darren-chait/E.227 Tech Tools: Move Your Audience By Moving Through Your Presentation https://www.fastersmarter.io/227-tech-tools-move-your-audience-by-moving-through-your-presentation/ Ep.230 Tech Tools: Use Visuals to Your Advantage https://www.fastersmarter.io/230-tech-tools-use-visuals-to-your-advantage/ Ep.233 Tech Tools: Write with Confidence and Impact https://www.fastersmarter.io/233-tech-tools-write-with-confidence-and-impact/ Ep.236 Tech Tools: Zeroing in on Your Email Communication https://www.fastersmarter.io/236-tech-tools-tech-tools-zeroing-in-on-your-email-communication/ Connect: Premium Signup >>>> Think Fast Talk Smart Premium https://www.fastersmarter.io/premium/Email Questions & Feedback >>> [email protected] Transcripts >>>Think Fast Talk Smart Website https://www.fastersmarter.io/239-tech-tools-how-smarter-scheduling-leads-to-stronger-communication/Newsletter Signup + English Language Learning >>>FasterSmarter.io http://fastersmarter.io/Think Fast Talk Smart >>>LinkedIn https://www.linkedin.com/company/think-fast-talk-smart/,Instagram https://www.instagram.com/thinkfasttalksmart/, YouTube https://www.youtube.com/playlist?list=PL6caGRBUYZCmgDGM2RK6mxKB9jG_ccmm3Matt Abrahams >>>LinkedIn https://www.linkedin.com/in/maabrahams/ 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 (08:19) - Communication Hack or Tool (10:24) - Conclusion ******* Thank you to our sponsors. These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost. Try Prezi today and get 25% off exclusively at prezi.com/thinkfast http://prezi.com/thinkfast.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:03Matt Abrahams?

  This Tech Tools mini series 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're 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 mini series of Think Fast, Talk Smart, the podcast. In this multi-part mini series,

• 0:48Matt Abrahams?

  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.

• 1:10Speaker 01

  Likewise, thanks, Matt. Really excited to be here.

• 1:12Matt Abrahams?

  So many of us have likely scheduled a meeting through Calendly, but 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?

• 1:31Speaker 01

  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 from 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 invent 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 they 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.

• 2:16Speaker 01

  Or you can look across multiple schedules to find the group of 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.

• 2:47Matt Abrahams?

  That's really exciting. Just taking out the struggle of scheduling a meeting, but to then add on to 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?

• 3:02Speaker 01

  Yeah, so our founder and CEO, Topo Atana, who is 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 want to lose that momentum. I don't want to have 7.6 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 Topo, he was hurting his pipelines as working in software sales.

• 3:47Speaker 01

  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 want to 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 A home services appointment via my website and then actually want to 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.

• 4:30Speaker 01

  But being a part 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 in follow up on the meetings as well? And that's where we're heading as a business.

• 4:44Matt 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?

• 4:58Speaker 01

  We've been talking about meetings for more than 10 years and it's an area that anyone who 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 pass on the 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. There's lots of memes out there about meetings that should have been emails and we all, you know, 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.

• 5:42Speaker 01

  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 sent 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 them at work. And 54% said more meetings would enhance their productivity at work. So on one sense, on one side, we're out there talking about meetings that should have been emails, these unproductive days that I spend in meetings, but then the overwhelming

• 6:27Speaker 01

  majority of professionals saying, give me more, I need more meetings. And that's a really interesting dichotomy to reconcile.

• 6:33Matt 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.

• 6:59Speaker 01

  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're all craving, 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 want to see it that competes with productive work.

• 7:30Matt Abrahams?

  Absolutely. So make meetings useful instead of competition for getting work done. Thank you for that. We'll be right back to finish our conversation. But first, we're going to take a quick break for a word from our sponsors. Their support covers the cost of production, so we can bring you this show for free. This podcast is sponsored by Squarespace. The best communicators don't just get their message across, they make it easy for people to know what to do next. Your website can do the same thing. With Squarespace, you can build a polished online presence that clearly shows people who you are, what you offer, and how they can work with you. If you offer coaching, consulting, classes, or other services, Squarespace lets you showcase those offerings,

• 8:11Matt Abrahams?

  take payments, and use Acuity Scheduling so people can book time with you directly. And with built in analytics, you can see how people are finding and engaging with your site, helping you make smarter decisions about where to focus. So your online presence doesn't just look professional, it helps people take action. Go to Squarespace.com/thinkfast for a free trial. And when you're ready to launch, use offer code THINKFAST to save 10% off your first purchase of a website or domain. Hi, Matt here. Sometimes the biggest obstacle to getting something done isn't the idea, the plan, or even the budget. It's finding the right person to help you execute. And the longer that takes, the easier it is to lose momentum.

• 8:56Matt Abrahams?

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• 9:40Matt Abrahams?

  So Darren, before we end, I'm asking all of the guests of this mini-series two questions. Are you ready for this?

• 9:46Speaker 01

  Let's do it.

• 9:47Matt Abrahams?

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

• 9:53Speaker 01

  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 Chester, 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.

• 10:22Matt 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 Callanly, what is one communication hack, tool, or shortcut that you use to help yourself be more effective in your communication?

• 10:51Speaker 01

  So this might It sounds 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. But 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 Loon, who I'm a big fan of. But as a principle 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.

• 11:32Speaker 01

  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.

• 11:41Matt 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 want to 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.

• 12:23Speaker 01

  It's great to chat. Thanks very much for having me.

• 12:27Matt 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 mini series. We appreciate Prezi's sponsorship of these episodes. This episode was produced by Catherine Reed, Ryan Campos and me, Matt Ibramhams. Our music is from Floyd Wonder with special thanks to Podium Podcast Company. Please find us on YouTube and wherever you get your podcasts. Be sure to subscribe and rate us. Follow us on LinkedIn, TikTok, and Instagram. And check out FasterSmarter.io for deep dive videos, English language learning content, and our newsletter. Please consider our premium offering for extended Deep Thinks episodes, Ask Mad Anythings, and much more

• 13:12Matt Abrahams?

  at FasterSmarter.io/premium. Before we wrap up, I just want to say thank you for listening. It really means a lot to hear how people all over the world are using these ideas in their own lives. It inspires me and the whole team that brings you this show. If you want more episodes and resources, feel free to follow, subscribe, and explore past conversations. We're grateful for your support of Think Fast, Talk Smart.