🗞️ The Podcasts are Back! And Some Are Not About AI!

Rolling up the CS podcasts of the week for you - in 5 minutes or more.

Author

Jen Weaver
August 16, 2025

Rolling up the CS podcasts of the week for you - in 5 minutes or more. This week I enjoyed the hell out of the Support Driven Expo and then crashed out for a couple of days. So this is coming at you on Saturday - as always, hit the TL;DR if you’re in a hurry, or hang around for the rest of the clips if you have time.

Containing:

  • TL;DR: three quick wins

  • The Podcasts: summaries + links from this week's podcasts

  • ICYMI on LI: curated posts from the week

  • And Now: meme of the week

TL;DR

If you only have a few minutes, check these out:

  • If as a manager, you feel like you’ve been given duct tape to fix a bleeding org, you’re not alone. (Manager to Manager at minute 8:07 and then even more at minute 35:48)

  • “All people are different people.” How to manage a team when every person has different needs. (One CX at Minute 26:22)

  • This is the best take I've ever seen on AI + your career: find your superpower with a custom GPT to help you do it.

🦸 This newsletter is brought to you by Supportman.io, which connects Intercom to Slack with AI to give agents feedback and surface problems in real time.

Happy to Help from Buzzsprout, with Priscilla Brooke

Peek inside an excellent customer team and copy how they run customer “orientations,” which engage new customers and convert trailers.

  • Proactive support: the fire department handles putting out fires but also educating people to put out fires and set up fire hydrants. Support teams need to do this, too - “to get ahead of those fires.” (Minute 4:16)

  • How Buzzsprout transformed 1-1 demos to 1-many calls. (Minute 16:45)

  • How to measure whether your customer education is successful. (Minute 27:00

The Modern Customer Podcast with Blake Morgan

An exploration of “agentic AI” with Rishi Rana , CEO of Cyara: AI systems that don’t just answer queries but reason, learn, and act. 

  • "The discussions in the last 10 years were all about digital transformation. The next 10 years are all going to be about agentic transformation. In practical terms, that means leaders are no longer just implementing software — they’re deploying autonomous agents that can reason, learn, take action, and even interact with customers in real time." (Minute 8:25)

  • "The fastest companies are not going to be reckless. They have built trusted systems that scale. That means embedding compliance, ethical guardrails, and customer protection into the architecture — not bolting them on later or ignoring them until it’s too late." (Minute 12:06)

Table Service Podcast with Jordan Hooker

Summary: Nick Cawthon shares why human oversight remains critical in AI-driven design. From ethnographic research to trust-building in support experiences, he explains how designers and support leaders can embed empathy into scalable systems.

  • "I don't think you're ever going to get an algorithm to understand the vulnerability and the fear of somebody on the curb with their arm in the air, hoping that a taxi cab sees them. That’s where the human in the loop comes in — they’ve been through that experience, out in the rain on the streets of Manhattan late at night, trying to get where they want to go. No computer has ever had that context." (Minute 7:20)

  • Why trust breaks when customers can’t get to a human, and why they’ll remember that forever. (Minute 13:25)

Matt Mangold 💻 discusses scaling support without losing empathy.

  • “An excellent support team is an excellent marketing tool. … A poor customer support experience can be a real problem, whereas a fantastic one is gonna pull people in.” (Minute 8:50)

  • “All people are different people.” How to manage a team when every person has different needs. (Minute 26:22)

  • I love this advice: the original support rep should be the point of contact for the customer throughout an escalation. (Minute 33:28)

Manager to Manager with Kamaria Scott

David Rice joins host Kamaria Scott on how managers influence employee engagement, especially in hybrid or distributed teams. If you’re a manager and you’re frustrated with the demands on you, this episode will be cathartic.

  • If you feel like you’ve been given duct tape to fix a bleeding org, you’re not alone. (Minute 8:07 and then even more at minute 35:48)

  • “We promote based on individual achievement, but then we expect people to help develop others and that's now their measurement of success.” (Minute 27:30)

The Supportive Podcast with Mathew Patterson

The story of Help Scout! From the three founders! Mat Patterson starts a season of talking with founders with his own founders. The whole thing is great, 

  • “The three of us did all of the support for so long and so we were so close to the problems,” because they hired engineers if they could do any hiring, before a support team. (Minute 9:25)

  • “There's this desire for things not to change too much, because in customer support, every change means extra work. A new feature means there'll be new bugs. Different pricing means you're going to have difficult conversations. … But of course, you also realize the products cannot stay still because everyone else is moving. And your customers need you to be helpful in today's world, not in the world of five years ago." (Minute 27:22)

  • Also check out this YouTube clip for this 3-minute clip of part of the conversation and a window into the Help Scout team retreat.

❝

 "Eat dog food — or better yet, be your toughest customer. If you’re solving your own pain, you’re more qualified to judge your solution to it."

ICYMI on LI:

Some posts from the support creators this week that are worth stopping your scroll.

🦸 This newsletter is brought to you by Supportman.io, which connects Intercom to Slack with AI to give agents feedback and surface problems in real time.

And now..

See you next time,

Jen