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Explore every episode of the podcast Customer Support Leaders

Dive into the complete episode list for Customer Support Leaders. Each episode is cataloged with detailed descriptions, making it easy to find and explore specific topics. Keep track of all episodes from your favorite podcast and never miss a moment of insightful content.

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TitlePub. DateDuration
297: AI Beyond The Queue; with Robert Cabral08 Apr 202600:33:06

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AI in customer support gets reduced to one tired idea: ship a chatbot and cut tickets. That mindset misses where the real leverage is. We sit down with Robert Cabral, Head of Customer Experience at Runway, to talk about “AI beyond the queue” and what it looks like when an AI-first company uses automation to scale service while protecting the customer relationship.

We get practical about the messy middle: migrating long-lived support reporting, pulling data from multiple sources, and turning scattered metrics into a clear weekly narrative that product and leadership can actually act on. Robert shares how AI helps teams find the story inside ticket data, platform usage, and escalations, and why reporting is only valuable when it drives a better customer experience, a better product roadmap, and a better day-to-day for the support team.

Then we move past talk and into action. We discuss chatbot foundations for product education, plus higher-impact automations that do real work, like refund handling with strict guardrails and human escalation when context is missing. We also explore how AI enables support teams to build internal tools and repeatable templates, even without traditional engineering backgrounds, and why that capability can become a career accelerator across CX, product, QA, and engineering.

We close on leadership: how to address the fear that AI will replace support roles, how to set customer-focused goals, and how to plan for different outcomes if AI resolves 90% of questions or falls short. If you care about customer support AI, CX automation, AI reporting, and building durable teams in a fast-changing landscape, you’ll want this one. Subscribe, share with a fellow support leader, and leave a review if it helps you rethink your AI roadmap.

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296: Flipping Away From Leadership; with Jenny Dempsey01 Apr 202600:36:20

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Getting laid off can scramble more than your finances. It can shake your identity, your confidence, and the story you’ve been told about what “success” in customer support leadership is supposed to look like. That’s why this conversation with Jenny Dempsey hit so hard: she went from a clear leadership path in customer experience to two years of uncertainty, experimenting with consulting, and rebuilding from a place that felt anything but predictable.

We talk about the moment she realized a leadership title no longer matched her values. Jenny shares what it was like to apply for individual contributor roles with 20 years of experience, get judged as “overqualified,” and wrestle with the temptation to downplay her background just to get hired. We also unpack a healthier approach: owning the choice, leading without the org-chart label, and focusing on skills that actually create impact like clear communication, customer empathy, and making work easier for the team.

Then we zoom out to the unexpected parallel that ties it all together: her furniture flipping business. The product is different, but the customer journey is the same. Setting expectations, choosing the right channel, giving progress updates, and protecting trust when timelines are long. Charlotte puts it simply: silence kills trust. If you’re navigating layoffs, a career pivot, burnout, or a non-linear support career path, you’ll leave with practical mindset shifts and a better way to tell your story.

Subscribe for more real conversations about customer support careers, share this with a friend who’s rethinking their next move, and leave a review with the title you’re ready to stop chasing.

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287: Extreme Delegation: How To Lead When Everything Changes At 4 PM On An Idle Tuesday; with Matt Dale28 Jan 202600:47:12

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A quiet Tuesday turns into a leadership stress test. We share the playbook for extreme delegation—those moments when a key lieutenant leaves, the CEO secondments you into a new role, or a surprise launch forces you to hand off mission-critical work fast without dropping standards. Matt Dale joins Charlotte Ward to unpack how to keep people safe, outcomes clear, and momentum steady when the plan changes mid-flight.

We start with the groundwork that makes speed possible: knowing your people, tools, and data; modeling calm, context-rich communication; and showing your work so others can replicate decisions. From there, we move into the safety contract that empowers new owners—explicit boundaries, time-boxed expectations, clear escalation paths, and a promise of advocacy when scope creeps or politics intrude. It’s still your accountability, and staying close with tight check-ins preserves agency while preventing drift.

Then we tackle ruthless prioritization. You can’t hand over your entire mental map and hope for the same outcome. Strip to essentials: customer promises that won’t bend, survival metrics, and the smallest system that delivers them. Pause nice-to-haves, and make smart, short-term investments—like an AI co-pilot or tighter knowledge flows—that shrink ramp time and amplify output. Real stories bring it to life: navigating a six-month secondment during acquisitions, replacing a leader mid-crunch, and accelerating an AI rollout to support hiring and scale.

This conversation is for support and CX leaders who have earned the reputation for getting it done and want a cleaner, calmer way to do it when chaos hits. You’ll leave with scripts, structures, and mindset shifts that turn a blindsiding week into a clear plan with confident owners. If this helped, follow the show, share it with a teammate who’s under pressure, and leave a review with your best extreme delegation tip.

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226: 99 Weeks Done04 Dec 202100:40:43

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Week 99 Topic: Reflecting 

Looking back over some of the best advice, and a couple of bonus outtakes from the last 99 weeks of the podcast! 

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Week 100 Teaser26 Nov 202100:03:34

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Looking forward to 100+ weeks!

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From The Archives: Ep 150: Fireside with Mo McKibbin19 Nov 202100:36:17

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From The Archives: Fireside with Mo McKibbin


Mo McKibbin talks about the challenges of screening for those magical unicorns: technical, customer success-support hybrids, remote, in Europe, ideally with specific industry experience. And we excitedly steal each others' favourite interview questions.

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From The Archives: Ep 146: Fireside with Tue Søttrup12 Nov 202100:21:26

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From The Archives: Fireside with Tue Søttrup


Tue Søttrup helps me kick off this new Fireside season with a conversation about Product-Led Customer Success, and how Dixa have used this approach to drive product engagement and business improvements for the customers at the same time.

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From The Archives: Ep 142: Diversity and Inclusion with Antonio King05 Nov 202100:16:04

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From The Archives: Diversity and Inclusion


Antonio King joins me to talk about the importance of keeping the conversations going, no matter how uncomfortable it feels..

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From The Archives: Ep 140: Scary Support Stories with Todd Curtis29 Oct 202100:27:10

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From The Archives: Scary Support Stories


Todd Curtis tells the scary story that inspired this whole week of terrible tales. I heard this at a conference two years ago and it still gives me chills. 

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From The Archives: Ep 136: Scary Support Stories with Matt Dale22 Oct 202100:09:15

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From The Archives: Scary Support Stories


Matt Dale joins me to tell the story of a possessed laptop. And I have rather too much fun with sound effects. 

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From The Archives: Ep 134: Support’s Relationship to Sales with Nicholas Zeisler15 Oct 202100:09:15

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From The Archives:: Support’s Relationship to Sales


Nicholas Zeisler (“Zee” to his friends, and “Zed” to his British friend over here) returns to talk about how CX can minimise friction in this less-obvious relationship. He’s at the end of the phone if you need him!

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From The Archives: Ep 129: Support’s Relationship to Product with Andrea Saez08 Oct 202100:14:20

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From The Archives: Support’s Relationship to Product


Andrea Saez joins me for the first time, where we talk about capturing all customer conversations and using that feedback to validate the product roadmap.

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From The Archives: Ep 123: Freelancing in Support with Andrei Kamarouski01 Oct 202100:13:44

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From The Archives: Freelancing in Support


Andrei Kamarouski joins me from Belarus, to talk about freelancing as a Zendesk consultant, primarily using Upwork.

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286: Measure What Matters When Humans And AI Share The Queue; with Craig Stoss21 Jan 202600:34:28

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AI has crossed a threshold in customer support: it no longer just routes and records—it actually does the work. We sat down with Craig Stoss, solutions lead at Codif, to unpack what changes when agents and co-pilots resolve real cases, trigger refunds, detect spam, and personalize replies across channels. The core shift is mindset: once software handles tasks, you need to manage it like a teammate—measure output, audit quality, plan capacity, and set honest expectations about what AI should own versus when a human steps in.

We map the strengths and limits on both sides. AI excels at repeatable workflows, multilingual responses, classification, and fast data gathering across commerce and CRM tools. Humans shine in ambiguity, ethical judgment, and emotional connection. That split demands better metrics: evaluate AI on loop frequency, hallucination rate, accuracy, and handoff health; evaluate humans on sentiment impact, recovery, and resolution quality. We also tackle the messy middle: what counts as “containment,” how AI prework changes case counts and AHT, and why your SLAs must adapt as simple issues disappear and human queues get harder.

Transparency matters for trust and compliance. Customers behave differently when they know they’re speaking with a bot, so make disclosure sensible and escalation simple. Inside your org, put AI into workforce management like a 24/7 agent with forecasted volume, coverage targets, and per-workflow goals—think 90 percent for FAQs, 80 percent for refund screening, and a lower bar for complex warranties. Budgeting evolves too: tokens and compute join salaries, compounding micro-saves into real capacity. The upside is big: more interesting human roles, fewer transfers, and a path to merge support and success so one empowered person, augmented by AI, owns the outcome end to end.

If you care about scaling support without losing humanity—smarter metrics, cleaner handoffs, and a realistic plan for AI and people to thrive together—this conversation is your playbook. Subscribe, share with a support leader who needs it, and leave a review with the one metric you’d change first.

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From The Archives: Ep 117: CSAT with Mo McKibbin24 Sep 202100:08:25

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From The Archives: CSAT


Mo and I spend quite a significant amount of time talking about the value of those smiley faces. And we take an unexpected hypothetical trip to the airport.

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From The Archives: Ep 115: Support Scope with Mike Redbord17 Sep 202100:09:01

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From The Archives: Support Scope


Mike Redbord believes you can build the scope of Support by saying “Yes” as much as possible!

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225: “In Support, I Believe…” with Simone Secci10 Sep 202100:02:40

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Week 87 Topic: “In Support, I Believe…”


Simone Secci shares his Support Belief: It’s not always about giving the customer exactly what they expect.

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224: “In Support, I Believe…” with Matt Dale03 Sep 202100:02:50

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Week 86 Topic: “In Support, I Believe…”


Matt Dale shares his Support Belief: It’s all about making a human connection.

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223: “In Support, I Believe…” with Craig Stoss27 Aug 202100:03:48

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Week 85 Topic: “In Support, I Believe…”


Craig Stoss shares his foremost Support Belief: The Customer Experience is the most import consideration

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222: “In Support, I Believe…” with Ryan Klausner20 Aug 202100:03:26

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Week 84 Topic: “In Support, I Believe…”


Ryan Klausner returns, this time from a new role, to share his most fundamental Support Belief: Agent Experience is as important as Customer Experience.

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221: “In Support, I Believe…” with Charlotte Ward13 Aug 202100:08:44

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Week 83 Topic: “In Support, I Believe…”


Your very host, Charlotte Ward, tells of her most fundamental Support Belief: Metrics should measure, not rule.

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Announcing “In Support, I believe…”06 Aug 202100:03:41

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Announcing a new format, based on “This, I Believe…”

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Throwback to Ep 109: Panel: If I Knew Then, What I Know Now….30 Jul 202101:02:35

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Week 81 Throwback: Panel 10


Five leaders join me to talk about the wonderful, frustrating and elusive nature of hindsight. If only we’d know then, what we know now.

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Throwback to Ep 103: Panel: Managing Change29 Jul 202100:58:24

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Week 81 Throwback: Panel 7


Six leaders join me to talk about managing change. We come to the conclusion it involves data, a 4-type taxonomy, a workshop, and a lot of cheese.

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285: From Playbooks To Personalization: How CX Leaders Shape Customer Expectations And Outcomes; with Ty Givens14 Jan 202600:32:07

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Superior customer experience isn’t a universal recipe—it’s a promise aligned to what your customers expect from you, in their moment, on their terms. We sit down with CX veteran Ty Givens to unpack why “good” is always relative and how teams can design for consistency without losing the human judgment that creates loyalty.

Ty shares the evolution from rigid scripts to flexible playbooks that teach thinking. We explore the 80/20 guardrails that keep quality high while giving agents room to zigzag across a process, adapt tone, and move at the customer’s pace. From fast, accurate answers in high-urgency scenarios to the warm, predictable greetings that define beloved brands, we examine how context shapes what “excellent” really looks like.

We also get practical about influence. Dashboards rarely win hearts in the boardroom; stories do. You’ll learn how to frame a single experience you want to change, pick the one metric that proves movement, and tie it to outcomes executives already value like CSAT, NPS, retention, and revenue. We cover how to connect first response time to satisfaction, how to separate policy pain from agent performance in CSAT reviews, and how to elevate support insights to product and engineering so fixes actually ship.

For leaders and frontline teams alike, this conversation is a roadmap: define expectations, empower judgment, and communicate impact with clarity. If you’ve been struggling to turn support data into action or to earn trust for your team’s recommendations, this is your playbook for telling better stories and creating better experiences. If this episode resonates, follow the show, share it with a colleague who leads support, and leave a quick review with the one metric that tells your best story.

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Throwback to Ep 99: Process Improvement with Ash Rhodes28 Jul 202100:06:59

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Week 81 Throwback: Process Improvement


Ash and I talk about how a culture willing to accept feedback and examination is best placed to improve on the status quo.

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Throwback to Ep 94: First 30 Days with Alyssa Percell27 Jul 202100:06:54

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Week 81 Throwback: First 30 Days in a New Role


Alyssa Percell and I start talking about ‘new to us’ roles, but unexpectedly dwell more on the plans we’re forming before we even get in the door.

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Throwback to Ep 83: Remote Work with Ash Rhodes26 Jul 202100:07:00

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Week 81 Throwback: Remote Work


Ash Rhodes pitched this topic to me with one phrase, and I took him up on his offer.

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Throwback to Ep 79: Forecasting in Support with Matt Dale23 Jul 202100:07:00

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Week 80 Throwback: Forecasting in Support


Matt Dale tells how he’s been refining his model for seven years, so don’t go looking for any quick and accurate answers in your first forecasting efforts.

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Throwback to Ep 72: Support Contributing to Revenue with Mo McKibbin22 Jul 202100:07:00

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Week 80 Throwback: Support Contributing to Revenue


This is such an interesting topic for most of us, that we’re visiting it twice this Throwback Week!  In this episode from the archives, Mo McKibbin joins me for the first time to talk about the topic that has defined such a huge part of her CS leadership career: Support Driven Growth

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Throwback to Ep 71: Support Contributing to Revenue with Mike Redbord21 Jul 202100:06:59

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Week 80 Throwback: Support Contributing to Revenue


Mike Redbord talks about the invaluable information and data your support team is already gathering, that might very well generate revenue.

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Throwback to Ep 62: Onboarding New Hires with Ash Rhodes20 Jul 202100:07:00

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Week 80 Throwback: Onboarding New Hires


Ash Rhodes isn’t a List Person, but he knows they’re useful for onboarding. We also find a name for that spyglass thing you do with your hands.

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Throwback to Ep 56: Building Leaders in Your Team with Meredith Molloy19 Jul 202100:06:56

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Week 80 Throwback: Building Leaders in Your Team
 
 Meredith Molloy returns to talk about how you spot, and care for a unicorn!

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220: Building a Team from Scratch with Matt Dale16 Jul 202100:17:18

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Week 79 Topic: Building a Team from Scratch


When is a full-time job not a full-time job? When it’s a two-person job! It’s been a while since Matt Dale built a team from scratch, but nonetheless, he returns to round out this week with his own wisdom and perspectives from further on in the journey.

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219: Building a Team from Scratch with Kat Olsheske15 Jul 202100:14:30

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Week 79 Topic: Building a Team from Scratch


In Kat Olsheske’s first outing on the podcast, she talks about the transferrable skills and knowledge every support leader brings to a new team, and what might be different between each team building experience. 

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284: Customer Support Leaders in 2026: Fresh Starts and More To Come; with Charlotte Ward and Alec Moloney07 Jan 202600:37:47

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Ready for a clean slate and a smarter way to build support in 2026? We kick off a fresh season with a rebuilt website, renewed energy, and a clear map of the big shifts reshaping our work: AI moving from side experiment to operational backbone, the leadership ladder compressing, and the customer journey turning truly dynamic. With Alec back on the mic, we share what sparked our collaboration, why the site overhaul mattered, and how we’re structuring episodes to turn complex trends into practical playbooks.

We dig into the AI arc we’ve watched up close: from generic tools to tailored systems grounded in product context and team workflows. That evolution changes how leaders think about risk, signal quality, and measurement. When each team builds its own AI-enabled flow, the data footprint becomes unique, and so must the metrics. We talk about moving beyond simple taxonomies and into cross-functional signals that reflect real value: reliability, effort reduction, resilience, and trust. It’s not about more dashboards; it’s about clearer decisions and better outcomes.

We also tackle the role overlap between support and customer success. Instead of strict handoffs, many teams are sharing tasks based on customer need, account complexity, and timing. The goal isn’t to blur expertise, but to surface the right context—recent incidents, account health, adoption goals—so the person in the room can help. That leads to our favorite battleground: journey mapping. Static maps that live on slides are fading. Dynamic journeys that adapt to signals are rising, supported by shared definitions, event-level visibility, and orchestration that changes course without creating chaos.

Expect returning guests, a few unfinished arcs finally wrapped, and plenty of new voices pushing us forward on AI maturity, metrics that matter, and the craft of leading modern support teams. If you’ve got a burning topic or a story worth sharing, head to customersupportleaders.com, scroll to the podcast page, and book a call. Subscribe, share with a teammate, and leave a review to help more leaders find the show.

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218: Building a Team from Scratch with Adela Bodor14 Jul 202100:16:23

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Week 79 Topic: Building a Team from Scratch


Adela Bodor returns to talk about building a support team from scratch: which she has done multiple times and has down to a fine art now!

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217: Building a Team from Scratch with Hilary Dudek13 Jul 202100:18:55

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Week 79 Topic: Building a Team from Scratch


Hilary Dudek and I haven’t talked in soooo long! She “recently” started a new role at Sana Benefits and joins me to talk about what she did first, and what she wishes she had invested in earlier.

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216: Building a Team from Scratch with Ashley Sachs12 Jul 202100:14:45

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Week 79 Topic: Building a Team from Scratch


Ashley returns to tell us how she prioritised early definition of ‘Operating Principles’ for her nascent team, and how they’re essentially still holding strong 4 years on.

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215: Knowledge Management with Craig Stoss09 Jul 202100:24:13

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Week 78 Topic: Knowledge Management


Craig Stoss and I muse about the validity of some of the metrics often applied to Knowledge Centred Support, and talk about the types of knowledge that apply in different situations. He resurfaces one of my favourite analogies for the difference between a KB and docs, too.


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214: Knowledge Management with Tadas Labudis08 Jul 202100:29:53

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Week 78 Topic: Knowledge Management


Tadas Labudis is the CEO and Founder of Prodsight. Today he returns to tell me about Prodsight’s own knowledge journey: from not believing he needed to document a product to embedding documentation in the product! 

Check out Tadas' previous fireside, where he talks about tagging taxonomies for Support! 

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213: Knowledge Management with Simone Secci07 Jul 202100:22:57

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Week 78 Topic: Knowledge Management


Simone Secci rebuilt a knowledge base from scratch, banking on being able to show its value much further down the road. It worked! From zero to knowledge hero, Simone talks about his journey.

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212: Knowledge Management with Cynthia Ng06 Jul 202100:21:15

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Week 78 Topic: Knowledge Management


Cynthia Ng describes how GitLab approach all their knowledge with a ‘Handbook First’ ethos, and how their value of Transparency informs everything they do. 

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211: Knowledge Management with Aprill Allen05 Jul 202100:15:06

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Week 78 Topic: Knowledge Management


Aprill Allen, a Knowledge Management Consultant & KCS Specialist at Knowledge Bird, helps support teams stop being so overloaded with solving the same problems over and over, and start using their knowledge as the lever it really is. How do we even get started on our Knowledge Management journey in Support?

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210: Fireside with Nicholas Zeisler 02 Jul 202100:26:50

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Specials: Fireside 26


According to “Zee” (if I could only say it), we’re doing CX wrong! Nicholas Zeisler joins again to tell us why we’re doing it wrong, and how to get it right. A man after my own heart, he says it hinges on the process! But how do you leverage process, prove ROI for your Customer Office, and truly develop a customer-centric culture? 

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209: Fireside with Ash Rhodes 25 Jun 202100:33:52

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Specials: Fireside 25


What a conversation! Ash comes on the podcast to talk about job hunting in Customer Support Leadership, but we only get there via comparing consulting notes and his insulting the average British meat pie. Honestly.

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283: From Values To Outcomes: Building A Customer Support Strategy That Works; with Conor Pendergrast06 Jun 202500:40:10

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Forget the glossy strategy deck. We’re digging into the real drivers of customer experience: the values people use to decide, the culture that shows up in daily behavior, and the incentives that shape how work actually gets done. With coach and consultant Conor Pendergrast, we unpack why a perfect plan won’t move the needle without the conditions that make good choices easy under pressure.

We start by drawing a clean line between objectives, strategy, and tactics—then flip the frame. Support is operational, reactive, and fluid, so the experience your customers feel depends less on long-range roadmaps and more on what your team is empowered to do in the moment. We explore how a tight set of actionable values can guide judgment when process hits the edge cases, why culture is simply the sum of visible behaviors, and how to spot “painted-on” culture that reads great but conflicts with what the metrics reward.

Then we get practical. We talk incentives that matter—protected time for knowledge creation, loops from customer pain to product fixes, KPIs that don’t punish improvement work, and recognition that matches how individuals like to be celebrated. We cover Goodhart’s law, double-loop thinking, and the operational rituals that keep teams learning: documenting confusing flows, aligning processes to ownership, and building capacity for continuous improvement. Expect candid examples, clear language, and tools you can use to align values, culture, and incentives so strategy becomes the way your team works, not a slide you forget by July.

If you want support that scales quality—fewer handoffs, clearer answers, and issues that don’t boomerang—start here. Subscribe, share with a fellow support leader, and leave a review to tell us which behavior you’ll reward first.

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208: Fireside with Doug Akers18 Jun 202100:08:56

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Specials: Fireside 24


Doug and I talked quite some time ago about “All-Hands Support”, which becomes a mini fireside episode today. We talk about the type of industries where this is an appropriate paradigm, and when and how it might be useful.

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207: Fireside with Josh Magsam11 Jun 202100:23:45

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Specials: Fireside 23


Josh brings a really interesting topic to the fireside today: specialisms in Customer Support and Service. We talk about everything from expertise to trusted advice.

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206: Fireside with Jim Israel 04 Jun 202100:31:39

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Specials: Fireside 22


Jim Israel talks about the dangers of developing a culture of heroism in our teams, despite being the type of folks who always want to help.

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