The Supportive Podcast

Help Scout

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Brought to you by Help Scout's Mat Patterson, The Supportive is a show for the customer-centric leaders of today and tomorrow. Tune in for tons of customer experience insights, practical tips, expert advice, and a bit of fun. (Also dad jokes).

15. Juli

Love It or List It for support tools with Chrissy Chavez

Thinking about switching help desks? Help Scout support pro Chrissy Chavez tells Mat why the urge to burn it all down and start fresh is so strong — and why an audit should always come first. Chrissy is a senior technical support specialist based in Oahu, Hawaii. She joins Mat to react to his newsletter "Why You Shouldn't Switch to Help Scout" — and the conversation turns into a playbook for anyone eyeing a support tool switch: what to audit before you move, how half of "missing features" turn out to already exist, and how to walk customers through a big tool decision without scaring them off. TIMESTAMPS: 5:48 Chrissy watches "Love It or List It" — "you're messy no matter where you live" 7:56 Half the "missing features" people want are already there 9:51 You might not have to switch tools at all 15:32 Audit your current tool first — saved replies, stale docs, historical data that could cause AI hallucinations 20:14 The emotional work of change: "Two weeks from now, we won't even remember it was different" LINKS FROM THIS EPISODE: - Find Chrissy on LinkedIn https://www.linkedin.com/in/chrissychavez - Read Mat's original newsletter https://email.helpscout.com/switching-tools - [Mat's 9-step guide to switching help desks](https://www.helpscout.com/helpu/switch-help-desk/). - Watch some Love It or List It https://www.youtube.com/watch?v=HOaEcx-DyPQ #CustomerSupport #HelpDesk #CustomerService
1. Juli

Speak to a human with Pavel Malyshev

Pavel drove AI customer support adoption as head of support...and then he got laid off. Mat chats with Pavel about his 13 years in B2B SaaS customer experience about the way execs are thinking about support today. Plus: why customers still want a human to confirm an answer, even when the AI got it exactly right. For a full transcript, notes, and links, see https://www.helpscout.com/blog/inside-ai-customer-support Find Pavel at: https://www.linkedin.com/in/pmalyshev/
15. Juni

Relevance before brevity in support with Leslie O'Flahavan

Leslie O'Flahavan has spent 30 years teaching people to write well at work — including plenty of customer service teams. Leslie and Mat discuss what it takes to write concisely in support, and how to develop your team's concise writing skills. Listen out for Leslie's simple 10% word-count game, and the surprising shift she's made just this year in her approach to spelling and grammar. For full show notes see https://helpscout.com/blog/customer-service-writing
2. Juni

700 classes and 0 perfect takes with Alison Groves

After 700+ live Help Scout classes, Alison Groves has figured out what makes customer education work — mistakes. Well, not exactly, but that's part of it. In this episode of The Supportive, Mat talks to Help Scout's Customer Education Lead, Alison, about what she's learned, how to get started, and why imperfection builds trust. WHAT WE COVER: - Why 90%+ of Alison's attendees stay for the full session - The three types of people who show up (and what each of them needs) - Why making mistakes live is a feature, not a bug - How to start even if you have zero experience - What happens when only 3 people show up vs. 120 - Whether AI will make live human teaching more or less valuable TIMESTAMPS: 0:00 Introduction 0:32 Meet Alison — 700+ classes and counting 4:11 What makes a great teacher (and a terrible one) 5:41 Getting over the fear of being wrong 8:09 Why people sign up for live classes 11:30 Live teaching vs. recorded demos 14:07 The value of imperfection 17:59 Advice for getting started 20:06 Your first step: just record yourself 22:14 Big class vs. small class — does it matter? 25:25 How to know if it's working For notes and links: https://helpscout.com/blog/teach-your-customers/
17. Mai

Kristi Thompson creates her own job

What if making your work visible wasn't about promoting yourself — but about telling the stories of your customers? Help Scout's Kristi Thompson spent nine years on the customer support team. She wasn't angling for a promotion or trying to build a personal brand. She just noticed a gap — consultative conversations that email wasn't suited for — and started volunteering to take those calls. She tracked what happened and shared it with her team and manager in Slack. Eventually, Help Scout created a customer success role and gave it to her. In this episode, Kristi and I talk through one edition of The Supportive Weekly newsletter "Why you should show your work" . Kristi brings the real-world version: what she actually did, why she called it an experiment, who was reading her Slack updates (more people than she expected), and how a one-minute video highlight reel can land harder than any spreadsheet. We also get into: whole company support, what remote work does to your visibility, the difference between self-promotion and reporting on what you've done, and why you should never expect anyone to connect the dots for you. https://www.helpscout.com/blog/the-su...
20. Apr.

5 Themes from Season 2

Season 2 of The Supportive brought together founders from seven very different businesses — software, hardware, beer, mattresses, and more — all with a reputation for putting customers first. In this wrap-up episode, Mat draws out the five themes that ran through every conversation: being your own customer, staying close as you grow, values that drive real decisions, deliberate growth, and treating support as intelligence. If you've followed the season, this ties it together. If you're just discovering it, start right here.
24. März

Is David Sparks too kind to be a lawyer?

Mat sits down with David Sparks — lawyer turned full-time creator — as he shares how 28 years in the courtroom shaped his approach to serving his technology audience. From playing imaginary clown music at raging opposing counsel, to personally answering emails from 93-year-old customers, David reveals what it looks like to build a business around kindness, craft, and staying close to the people you serve. https://www.helpscout.com/resources/supportive-podcast/macsparky/ for full show notes.
8. März

NapLab tells you what mattress sellers will not

NapLab — Our First Customers on The Supportive Mat Patterson talks with Derek Hales, founder of mattress review site NapLab, about building a customer-centric business in an industry that works hard to keep consumers in the dark. Derek shares how a frustrating mattress shopping experience led him to create one of the web's most rigorous product review platforms — and what happens when the reviews don't work for readers. For the full show notes and transcript: https://helpscout.com//resources/supportive-podcast/naplab/

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Trailer

Welcome to The Supportive!

Check out the trailer for the upcoming Supportive Podcast from Help Scout.

Brought to you by Help Scout's Mat Patterson, The Supportive is a show for the customer-centric leaders of today and tomorrow. Tune in for tons of customer experience insights, practical tips, expert advice, and a bit of fun. (Also dad jokes).

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2024 - 2026
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The Supportive Podcast