Customer Support Leaders

Charlotte Ward
  • 5.0 (2)
  • Management
  • Updated Biweekly

Customer Support Leaders have been there, on the front line with customers. They understand how things work, and the value of support. They understand the needs and foibles of their customer base. Unlike most other disciplines, there’s no training for this role. No two CS Leadership roles are alike. No two CS Leaders are alike. So this is our opportunity to hear from those leaders and learn from them. Whether you’re a CS leader now, or you aspire to be, this is the podcast for you! Hear different leaders discuss a topic with me, Charlotte Ward.

  1. 4d ago

    306: Outcomes Over Optics; with Carl Lenocker

    Send us Fan Mail Great support can look “perfect” on paper and still fail the customer in real life. That tension is what we dig into with Carl Lenocker, a senior customer success executive, executive coach, and longtime support leader, as we unpack a simple idea with big consequences: outcomes over optics. We get concrete about how traditional support KPIs like first contact resolution, time to answer, and fast ticket closure can quietly create the wrong behaviours. When the business rewards speed and box-checking, teams get pushed toward rushed calls, prematurely closed cases, and fewer relationship-building moments. Carl shares lessons from running global support at HP and why many of these pressures ultimately trace back to money, cost cutting, and the old “support as a cost center” story, especially during the outsourcing era. From there, we look forward. We talk about AI in customer support as a way to handle simple issues quickly, and why the real opportunity is to reinvest human time into premium, consultative, relationship-driven support that prevents the next ticket and protects renewals. We also call out action faking, including performative QBRs, and Carl breaks down what actually matters in a customer business review: business objectives, progress, and risks, not 50-slide theatre. If you lead support or you’re building a career in post-sale, you’ll leave with sharper language for executives, better internal alignment, and a clearer way to prove value beyond dashboards. Subscribe for more conversations like this, share this with a support leader who needs it, and leave a review with the metric you think your team should stop worshipping. Support the show

    43 min

  2. Jun 3

    305: Measuring Your Support Maturity; with Neal Travis

    Send us Fan Mail Support teams don’t usually fail because they “don’t care” or “aren’t working hard enough.” They fail because they scale on instinct, accumulate tribal knowledge, and measure whatever is easiest until the whole system starts to wobble. We sit down with Neal Travis, Head of Customer Experience and Operations at AIHR, to talk about measuring support maturity in a way that leads to real decisions, not a prettier dashboard. Neal shares how a small team can support a large customer base by getting ruthless about what support owns and how the work is designed. We walk through Neal's support maturity framework built around three domains: knowledge, quality, and data and insights. On the knowledge side, we dig into self-service experience, internal knowledge management, and training that prepares the team for what’s coming next, not just onboarding. We also unpack why “supportability” is an outcome when documentation, enablement, and cross-team alignment are strong, and why customers learning changes before support does is always a red flag. From there we move into quality, separating communication quality (standards, coaching, QA programmes, onboarding for great conversations) from operating quality (channels, capacity, coverage, incident management, and the reality of a messy support tech stack). Finally, we get practical about support metrics and measurement architecture: choosing the right metrics, understanding trade-offs like handle time vs after-call work, building reliable data infrastructure, and turning voice of the customer into action that closes the loop. If you want a clear picture of where your support function is mature and where it’s fragile, this conversation gives you a map. Subscribe for more, share this with a support leader who’s trying to scale, and leave a review with the one domain you’re working on next. Support the show

    37 min

  3. May 27

    304: Reverse One-to-Ones; with Greg Skirving

    Send us Fan Mail Your one-on-ones shouldn’t feel like a weekly status treadmill where we do all the talking and our team does all the nodding. Charlotte Ward sits down with Greg Skirving to unpack a deceptively simple leadership shift: the reverse one-on-one, where the direct report leads with their perspective instead of waiting for the manager’s agenda.  Greg walks us through his practical structure a three-slide monthly check-in covering accomplishments, challenges, and what the person wants to improve next. We talk about why this works especially well in customer support and technical support environments that are drowning in metrics like tickets closed and MTTR, while so much real value goes uncounted: mentoring, onboarding, process fixes, cross-functional help, and customer moments that protect renewals. The goal isn’t more paperwork, it’s clearer thinking, better coaching, and a more honest view of impact.  We also dig into the change management piece: why the first few rounds can be awkward, how to coach ICs who dislike “talking about themselves,” and how presenting internally becomes a safe way to build communication and confidence that carries into customer calls, incident leadership, and even career moves into pre-sales, implementation, or project roles. By the end, we connect the dots to a simple career advantage: building an ongoing evidence file that makes self-evaluations and promotion conversations easier because the proof is already collected.  If you want one-on-ones that create growth and not just updates, listen now, then subscribe, share with a fellow support leader, and leave a review. What would you change about your one-on-ones first? Support the show

    27 min

  4. May 20

    303: Practically Perfect Support; with Jason Yun

    Send us Fan Mail Mary Poppins is “practically perfect” and that makes her a surprisingly useful guide for modern customer support leadership. We (Charlotte Ward and Jason Yun, Head of Provider Success at Prax Health) use the film’s songs and characters to translate timeless ideas into practical support team lessons: hire for kindness and wit, stay close to the frontline, and remember that people at work still want to be seen, heard, and understood even when the market feels harsher than it did a few years ago.  We talk about advocacy and allyship through “Sister Suffragette”, and we confront the Mr Banks trap: getting rigid, comfortable, and oblivious while chaos quietly builds around you. From there we get extremely tactical with “A Spoonful of Sugar”, unpacking how support leaders deliver bad news, write appeasement emails, de escalate tense calls, and keep dignity intact for customers and agents. We also call out the gap between big vendor visions and what teams actually need day to day, including an honest take on AI in customer support and why hype rarely matches real budgets or proven outcomes.  Along the way, Bert becomes the model for a different kind of leadership voice: the storyteller who reframes, suggests alternatives, and helps people change without being shamed. We close with “Let’s Go Fly A Kite” and a simple north star for the future of customer success and customer support: let automation handle the boring clicks while humans lead with trust, relationship building, and product insight that actually improves the customer experience. If this made you rethink your own leadership style, subscribe, share the episode with a fellow support leader, and leave a review. Support the show

    1h 9m

  5. May 13

    302: Using AI to identify coaching opportunities; with Rob Dwyer

    Send us Fan Mail Most coaching goes wrong before the coaching conversation even starts. If we only review a tiny sample of calls, chats, or tickets, we end up “coaching the seventh hole” and missing the real issue that shows up earlier in the customer journey, like unclear expectation setting or a pattern that repeats across channels. I’m joined by Rob Dwyer, Senior Technical Account Manager at Level AI and CX Executive in Residence, to unpack how AI can identify coaching opportunities without pretending to replace leadership. We use a surprisingly useful golf analogy to explain the core problem: agents are “playing” all day long, on different levels of difficulty, while supervisors are juggling escalations, PTO, reporting, and intraday chaos. In that reality, humans cannot reliably watch enough work to spot true patterns, but AI can, because pattern recognition is exactly what these models do well. We also get practical about what “signals” can look like, including an omnichannel example where an agent sounds fantastic on the phone but struggles with written communication in email and ticket replies. That’s a hidden coaching gap unless you’re analysing conversations across voice and async work. Along the way, we talk about using AI to highlight strengths so recognition is specific, and how this can help newly promoted managers calibrate quickly between foundational coaching and skill refinement. If you want coaching that feels fair, evidence-based, and actually improves customer experience, listen now, then subscribe, share this with a fellow support leader, and leave a review with the biggest coaching blind spot you see on your team. Support the show

    37 min

  6. May 6

    301: Using AI To Make Us Better Managers; with Reagan Helms

    Send us Fan Mail Your calendar says “1:1s,” but your brain hears “context switching.” Charlotte Ward sits down with Reagan Helms, VP of Customer Experience at Planning Center, to unpack a practical way AI can make us better managers: a management assistant that strengthens one-on-ones without turning leadership into autopilot. We get specific about how Reagan built his system and how it evolved, from separate AI chats per employee to a persistent copilot that can pull the right notes at the right time. We talk about the real-world plumbing behind “AI for managers” including Notion as a human-friendly interface, why Notion can be painful as a retrieval layer, when spreadsheets are the simplest high-performance backbone, and how a vector database can unlock faster search across qualitative coaching history. We also dig into meeting transcription, prompt refinement, and the discipline of verifying outputs so the manager stays responsible for the data and the decisions. Then we zoom out to the leadership impact: fuller agendas, fewer forgotten commitments, and an “impartial mirror” that helps you sanity-check whether you communicated clearly or whether an annoying behaviour is actually your coaching taking root. We also tackle the trust side head-on, with boundaries and consent so AI support doesn’t drift into surveillance or creep your team out. If you’re leading customer support, customer experience, or any growing team, hit play, share it with another manager, and subscribe for more. After you listen, leave a review and tell us: what would you want an AI management assistant to handle first? Support the show

    39 min

  7. Apr 29

    300: Reflecting on the Year So Far; with Alec Moloney

    Send us Fan Mail A lot has changed since the start of the year and not just job titles and cities. Charlotte Ward sits down with returning guest Alec Maloney to take stock of what is actually happening inside modern customer support teams as AI, automation, and faster tooling collide with the day-to-day reality of customers, tickets, and people management. We get practical about the new build vs buy trade-offs for AI in customer service. Alec shares what it looks like to evaluate vendor platforms and aim to shift a meaningful chunk of ticket volume to AI-assisted chat and email, while Charlotte explains why her instinct is often to build custom systems that fit the exact workflow. Along the way we talk Zendesk reporting, scripts generated with AI, and why “solve the problem in front of you” has become a useful operating principle for support operations and CX leadership. Then we zoom out to the bigger changes: blurred boundaries between support, ops, and adjacent functions, the need for centralised knowledge (Notion, Confluence, knowledge bases) to make AI effective, and the weird new shape of career progression. Title compression and flatter orgs mean growth can feel like more scope and more influence rather than a clean promotion, which raises real questions about sustainability, delegation, and what different team members actually want from their careers. If you lead customer support, CX, or support ops and you are trying to make AI useful without losing the human layer, this conversation will give you language, examples, and a few sharp edges to think about. Subscribe, share this with a fellow support leader, and leave a review with the one change you are seeing most in your own team. Support the show

    59 min

  8. Apr 22

    299: AI Won't Fix Your Knowledge Quality Problem - It'll Expose It; with Leslie O’Flahaven

    Send us Fan Mail AI can generate a clean looking knowledge article in seconds, but that speed comes with a trap: it makes bad knowledge easier to publish and easier to surface. Leslie O’Flahavan joins me to unpack a simple claim with big consequences for customer support leaders and knowledge management teams: AI won’t fix your knowledge quality problem, it will expose it. We get practical about what AI can do well (drafting, simplifying language, reformatting for different audiences) and what it cannot do for you (understanding the real human reader who is stressed, new to the task, or missing context). Leslie explains why writing is more than editing and why relying only on revision can create “brain flab” as teams stop practising planning and organising. We also dig into a better way to judge content: stop asking users whether they like it and start asking whether they can complete the task with your self service help. From there, we explore concrete tactics to make the reader real again: using daily ticket feedback as gold, building articles around customer questions, and designing knowledge base and FAQ structure that works for both humans and AI search. If you’re feeling AI fatigue, this conversation reframes the moment as an opportunity to do more meaningful knowledge gardening, not less. Subscribe for more conversations on support leadership, AI in customer service, and knowledge base strategy, and if this helps, share it with a teammate and leave a quick review. Support the show

    43 min
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About

Customer Support Leaders have been there, on the front line with customers. They understand how things work, and the value of support. They understand the needs and foibles of their customer base. Unlike most other disciplines, there’s no training for this role. No two CS Leadership roles are alike. No two CS Leaders are alike. So this is our opportunity to hear from those leaders and learn from them. Whether you’re a CS leader now, or you aspire to be, this is the podcast for you! Hear different leaders discuss a topic with me, Charlotte Ward.

Information

  • Creator
    Charlotte Ward
  • Years Active
    2019 - 2026
  • Episodes
    369
  • Rating
    Clean
  • Copyright
    © 2026 Customer Support Leaders
  • Show Website
    Customer Support Leaders