Think Fast Talk Smart: Communication Techniques

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

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Oct 30, 2025

Darren Chait, Vice President of Growth at Calendly, shares insights on transforming communication through scheduling automation. He discusses how Calendly minimizes scheduling friction and enhances meeting productivity. Highlights include research findings that most professionals desire more effective meetings and how intentional scheduling fosters stronger relationships. Darren also emphasizes the importance of clear objectives and advocates for asynchronous communication to navigate collaboration across time zones. Discover the future of meeting effectiveness!

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ADVICE

Automate Scheduling To Save Momentum

Use scheduling links to eliminate back-and-forth and speed booking with prospects and partners.
Route invitees to the right person or accept payment at booking to turn meetings into revenue-generating interactions.

INSIGHT

Meetings Need Lifecycle Support

Scheduling is only one part of the meeting lifecycle; preparation, engagement, and follow-up determine success.
Calendly plans AI features to help before, during, and after meetings, not just book them.

ANECDOTE

Founder Built Calendly From Sales Frustration

Tope Awatona built Calendly after losing sales momentum to scheduling back-and-forth in 2013.
That personal frustration drove features for team routing, payments, and expanded scheduling automation.

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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.

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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
(10:13) - Communication Hack or Tool
(12:18) - Conclusion

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