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Published by 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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Should you trust a chatbot when it sometimes makes mistakes? Javier Silverio has spent eight years in the Help Scout support queue, and now builds the team's internal AI tools. He read Mat Patterson's Supportive Weekly newsletter on AI and trust, and they get into what it means to hand your data to a company when you can't check what happens to it, why customers have been so quick to forgive a wrong answer from a bot, and how trust tends to get built at the moment something breaks. Some key moments (3:27) What DJ requests and feature requests have in common (6:41) "Should I build it just because I can?" (7:47) The Monzo co-founder who records every conversation (12:16) Trust gets built when something goes wrong (21:21) Some people will wrestle with a bot, some just want the answer (23:34) A year spent teaching an AI tool to say "I don't know" LINKS FROM THIS EPISODE Show notes: https://helpscout.com/blog/javier-expected-complaints/ Javier on LinkedIn: https://www.linkedin.com/in/javsilverio The Tom Blomfield talk Javier mentions: https://www.youtube.com/watch?v=X_JsIHUfUjc&t=140s Mat's article on trust, AI, and customer service: https://www.helpscout.com/blog/trust-ai-and-customer-service/ The newsletter Javier reacted to: https://email.helpscout.com/our-new-insentient-overlords LISTEN TO THE SUPPORTIVE Spotify: https://open.spotify.com/show/61pw99zFj5MnP5I3L8S26d Apple Podcasts: https://podcasts.apple.com/us/podcast/the-supportive-podcast/id1743286439 Newsletter: https://www.helpscout.com/newsletter/supportive/ The Supportive is Help Scout's podcast about customer service and the people who do it, hosted by Mat Patterson. #customerservice #AIchatbots #customersupport
Dave Berner is a software engineer who, as a two-time founder considers himself "almost unemployable". Dave chats with Mat about careers in an AI-disrupted world. Dave chats with Mat about using AI as a sounding board, keeping people in the loop, and how he thinks about career planning when so much of the future remains uncertain. Watch the full interview here or subscribe to The Supportive in your podcast player of choice. Some key moments (2:36) Using AI as a thinking partner and not a hype man (8:19) Is Dave disrupting or enabling? (11:15) Who's responsible when AI gets it wrong? (13:20) Doctors and their AI diagnosing problem (19:24) Why Dave stopped trying to pick one job title (23:22) Building your network before you need it (29:51) Embracing AI without losing yourself Too long, didn’t watch? Here’s a concise version: Trust the person behind the AI - Dave says "You're basically paying for insurance" by having a trusted, informed person to verify and be responsible for a decision even when AI made it. AI as a sparring partner, not an oracle. - Conversational AI can help you figure out your own answers, rather than tell you what to think. Start asking questions now. - Find the people you trust and ask them what they've noticed about your strengths, and the areas that might need work. Visit https://helpscout.com/blog/almost-unemployable/ for all the links and notes.
Nicole Crayne, self-proclaimed "Chaos Wrangler" at Saffire, spent 12 years between support roles wrangling the chaos and the curiosity of kids as a stay-at-home parent. Now back in the corporate world, Nicole chats with Mat about what it takes to build curiosity into a team - trust, slack time, and a type of disciplined approach to asking "why". We also learn how her dad has sustained a decades-long plumbing business on a specific attitude towards service. See https://helpscout.com/blog/fix-your-plumbing/ for show notes and links.
Beth Trame has built support organizations from scratch multiple times, including at Lyft and Square, both businesses that dealt with steep volume increases and diverse customer bases. In this episode, Beth shares her experiences as we discuss customer feedback, criticism, and how support teams respond to them. Some key moments (0:19) Meet Beth Trame: Square, Lyft, and 10 years at Google (1:21) The newsletter: "Nobody Likes to Be Criticised" (5:45) The three-way relationship: driver, passenger, and the business (12:29) One-star reviews and reaching out to drivers directly (16:35) The A/B test that split CSAT into product vs. agent (25:28) Project Aristotle and psychological safety (35:21) Beth's advice: be a listener first For show notes and links visit https://helpscout.com/blog/customer-feedback-lessons-from-lyft-square-google/
Tom joined Help Scout's support team in 2026, but he's been using Help Scout for a decade. He chats to Mat about his role in improving Zapier's support team diversity, what actually changed to hit their goals, why an interview process that never changes isn't neutral, and how improving diversity also improved camaraderie. Key moments: (5:24) Tom's alottment in the UK, and companion planting as team building (7:26) Zapier's project to make their team reflect their wider country (13:33) Creating a more accessible and fair interview process (19:11) Culture fit is a signal, not a deciding factor (20:44) Camaraderie built by diversity (29:43) Everyone already has a hiring rubric, even if it's unwritten
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
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/
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
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/
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...
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.
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.
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/
Mat sits down with Oscar McMahon, co-founder of Sydney brewery, Young Henrys, as he shares how community, values, and a ‘challenger mindset’ have helped build one of the city's most loved independent companies. From the Inner West music scene to their “Serve the People” ethos, Oscar shares how purpose shows up in hiring, customer service, and business strategy. Full show notes and links: https://www.helpscout.com/resources/supportive-podcast/younghenrys/ Listen out for: (04:16) The birth of craft beer culture and why engagement matters (06:01) Inner West Sydney: the impact of local culture (09:05) How a passion for music shaped Oscar’s leadership (11:04) Lessons from touring bands and applying them to business (14:09) Every touchpoint matters: holistic customer service (15:36) Why shared company values come first (17:16) Making values stick with a self-policing culture (19:06) Hiring for fit: values vs experience (22:26) Embracing challenge for genuine growth (28:30) Human connection beats tech in hospitality (29:16) Community partnerships and authentic marketing (33:13) What “Serve the People” really means at Young Henrys (34:11) Sustainability, B Corp and the innovative algae project (39:13) Building real customer value beyond transactions (44:23) Independence vs. challenge: what keeps brands thriving
Todd Curtis, CEO of YNAB, shares how customer support became the foundation for sustainable growth. Learn why they embedded support in product teams and used it as a training ground for company-wide leadership. Here's the original YNAB Support Ethics document (long since replaced with expanded versions) https://2760806.fs1.hubspotusercontent-na1.net/hubfs/2760806/YNAB%20Support%20Ethic.pdf Discover how YNAB’s “education first” approach shaped not only how they help customers, but also how they build their own business. If you’ve ever wondered how support can become a secret engine for company growth (and even leadership) this is the episode that shines a light. (01:39) The Excel spreadsheet that started it all (05:16) Early support workshops and one-to-one coaching (07:15) “Five case Monday” and whole-team support (10:31) Why YNAB sees itself as an education company (12:47) Crafting the YNAB Support Ethic (17:27) Embedding support specialists in product teams (22:36) Support as a pipeline for talent across YNAB (28:43) Navigating major product and branding changes (33:09) Moving from “budgeting” to “planning” – and why words matter (34:01) Living core values inside and outside the company (36:57) Balancing customer experience with sustainable business growth Support is about more than technical issues: YNAB’s support team isn’t just resolving sync errors and resetting passwords — they’re helping people change their mindset about money, and get their financial life back. The most impactful conversations in the queue often go beyond troubleshooting to coaching, education, and emotional support. Empathy drives long-term success: By noticing and celebrating deeper customer interactions (not just ticket volume), YNAB builds trust and loyalty. Expanding the definition of support work makes for a more satisfying role, stronger customer relationships, and helps grow the business. Support Talent Powers the Company: At YNAB, support is a launching pad for roles across product, marketing, and operations. Hiring for values, communication, and willingness to learn pays off when support pros bring customer focus and cross-functional skills company-wide.
Chris Savage, co-founder and CEO of Wistia, shares how staying in the support inbox for ten years, walking away from a potential major deal with HBO as customer #4, and choosing patience over growth helped their team build a video marketing platform where every product decision starts with understanding customer pain—not just counting feature requests.
Erez Zuckerman, CEO and co-founder of ZSA Technology Labs, shares how a focus on craftsmanship, honest communication internally and externally and deep support has helped his small keyboard company punch well above its weight.
What does it take to earn the trust and loyalty of over 12,000 customers, build a team that cares like you do, and hold onto your values for over a decade? In the first episode of season 2, go behind the scenes with the three founders of Help Scout – Nick Francis, Denny Swindle, and Jared McDaniel – and hear how they turned their frustrations with clunky support tools into a business renowned for its customer focus. For show notes, transcript, and links: https://helpscout.com/resources/supportive-podcast/S2E01/
Mat answers Ita's newsletter-follow-up question: How can we frame AI chatbots as self-service tools, not worse-than-human support? Find the original newsletter here: https://email.helpscout.com/harm-joy and visit https://helpscout.com/blog/blog/reframing-as-chatbots/ for further links. Thanks Ita for the great question!
Season 1 of the podcast comes to an end, and Mat explores the recurring themes in classic clip-show style. Listen for a sneak peek of season 2!
Ranking source
Apple Podcasts rankings via the Mato Topic Intelligence Platform.
Observed November 3, 2026. Cached outside the daily freshness window; the positions keep the date they were taken on.
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