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SummaryThis episode kicks off a compelling three-part series featuring John Huber, founder of Customer Success Architects, who brings two decades of experience building CS functions across five different SaaS companies. The conversation centers on the fundamental question every growing business faces: how do you launch a customer success function that actually drives results? John shares his battle-tested approach, emphasizing the critical importance of aligning CS initiatives with company-wide strategic objectives rather than jumping straight into tactical execution. Through a fascinating case study involving a massive platform transformation for enterprise pharmaceutical and high-tech manufacturing clients, he demonstrates how proper alignment enabled a successful four-and-a-half-year migration from on-premise to cloud infrastructure without losing a single customer. This customer success playbook episode provides essential groundwork for any organization looking to build or rebuild their CS foundation.
Detailed AnalysisThe discussion reveals several strategic insights that challenge conventional CS wisdom. Rather than immediately focusing on hiring CSMs or implementing technology platforms, John advocates for a "strategy-first" approach that ensures every CS initiative ladders up to broader business objectives. This methodology becomes particularly powerful when managing complex transformational projects, as evidenced by his experience migrating enterprise clients from legacy on-premise systems to modern cloud platforms.
The episode highlights three critical success factors for new CS functions: strategic alignment with three-year company vision, cross-functional collaboration (especially with legal and finance teams), and allowing significantly more time than initially estimated for complex transitions. John's approach to contractual restructuring during platform migrations offers valuable lessons for companies navigating similar transformations, particularly the importance of providing financial incentives and flexible contract structures during transition periods.
The conversation also underscores how customer success professionals must evolve beyond traditional support roles to become strategic business partners. John's team successfully positioned platform limitations as innovation opportunities, demonstrating the communication skills necessary to maintain customer relationships during potentially disruptive changes.
For CS leaders and executives, this episode provides a practical framework for launching CS initiatives that deliver measurable business impact while maintaining strong customer relationships throughout complex organizational changes.
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The Customer Success Playbook podcast wraps up its enlightening three-part series with Kristen Nolan of Interview Valet by exploring the delicate balance between technology and human connection. In this forward-thinking discussion, Kristen reveals how she leverages AI as a strategic tool while maintaining authentic relationships. From using AI to identify unique client differentiators to employing dictation for efficiency, this episode offers practical ways to harness technology without sacrificing the personal touch. Hosts Roman Trebon and Kevin Metzger guide a conversation that demonstrates how AI can enhance rather than replace meaningful connections in customer success.
Detailed AnalysisAs AI continues to transform business operations, customer success professionals face a critical question: Can technology actually strengthen human relationships rather than diminish them? This episode provides a refreshingly balanced perspective that avoids both technological evangelism and fearful resistance.
Kristen Nolan's approach to integrating AI into client relationships stands out for its pragmatism and strategic focus. Working at Interview Valet, where "relationships are the ultimate currency" serves as a core value, Kristen has developed a methodology that leverages AI as a starting point rather than an end solution. Her process of using tools like ChatGPT to identify a client's unique differentiators demonstrates how AI can enhance relationship-building by providing deeper insights that might otherwise remain undiscovered.
What makes this discussion particularly valuable for the customer success playbook is the emphasis on maintaining authenticity while embracing technological efficiency. Kristen's guidance on viewing AI outputs as "a baseline" that requires human refinement offers a practical middle path for CS professionals concerned about sounding robotic or inauthentic in client communications. As she notes, "AI can't make up personal stories for you," highlighting the irreplaceable value of human experience in building genuine connections.
The hosts share equally practical applications, with Roman revealing how he uses AI to improve the tone and client-centricity of his communications—not by blindly copying AI outputs, but by using them as a mirror to recognize when his natural communication style might come across as too abrupt. This application addresses one of the most common challenges in customer success: ensuring that necessary direct communications don't damage valuable relationships.
For customer success teams looking to scale their operations without sacrificing quality, this episode provides a framework for thoughtful AI integration. The discussion moves beyond theoretical benefits to share tangible techniques like using ChatGPT projects to maintain context, leveraging dictation for efficiency, and using AI to help craft more concise communications. These practical tips demonstrate how technology can free up time for meaningful relationship-building rather than replacing it.
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The Customer Success Playbook podcast delivers a thought-provoking exploration of confidence building in this captivating episode featuring Kristen Nolan of Interview Valet. Hosts Roman Trebon and Kevin Metzger guide a discussion that dives into overcoming self-doubt and imposter syndrome. Kristen shares her personal journey from questioning "who cares what I have to say?" to becoming a confident podcast guest who now coaches others. With refreshing honesty about her own struggles and triumphs, she reveals how facing fears head-on can lead to remarkable personal and professional growth.
Detailed AnalysisBuilding confidence isn't just a personal development goal—it's a critical professional skill, especially in customer success roles where relationships and credibility are paramount. This episode tackles the universal challenge of silencing the inner critic that so often holds professionals back from reaching their full potential.
Kristen Nolan's approach to confidence building centers on one powerful concept: taking action despite doubt. She candidly shares her own hesitation when first approached about being a podcast guest, revealing that her immediate reaction was, "Who cares what I have to say?" This transparent admission resonates because it reflects a common barrier many customer success professionals face—questioning their expertise or value.
What makes Kristen's perspective particularly valuable for the customer success playbook is her emphasis on how facing fears creates a feedback loop of growth. By "ripping the bandaid off" with her first podcast appearance (which she admits was "pretty terrible"), she developed skills and insights that now help her better serve clients. This practical example demonstrates how pushing through discomfort directly enhances client relationship capabilities.
The conversation takes an even more profound turn when Kristen addresses self-sabotage—identifying it as one of the most significant barriers to achievement. For customer success professionals, this insight is especially relevant, as hesitation in challenging client conversations or strategic recommendations can undermine effectiveness. Kristen's advice to visualize goals and map the path backward (her "Z to A thinking") offers a tactical approach to overcome this tendency.
Perhaps most powerfully, the discussion draws a connection to broader life satisfaction, referencing the common deathbed regret of "not having the courage to live authentically." This reminder elevates the conversation beyond mere professional development to touch on how building confidence impacts overall life fulfillment—a holistic perspective that aligns perfectly with the integrated work-life approach many customer success professionals strive to achieve.
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In this eye-opening episode of the Customer Success Playbook podcast, hosts Roman Trebon and Kevin Metzger welcome Kristen Nolan, Senior Client Account Manager at Interview Valet. As a military spouse, mother of three, and active community volunteer, Kristen shares her battle-tested strategies for managing a packed schedule. Her number one tip? Taking control of your calendar through intentional time blocking. Discover how this simple yet powerful technique helps Kristen juggle professional responsibilities while maintaining flexibility for life's unexpected moments and personal priorities.
Detailed AnalysisEffective calendar management might be the most underrated skill in today's busy professional landscape. Kristen Nolan, who juggles multiple roles with impressive grace, offers a masterclass in time management that any customer success professional can immediately implement.
Kristen's approach centers on what she calls "Z to A thinking" - a methodology where she identifies all weekly tasks first, then strategically schedules them on her calendar. This proactive stance ensures nothing falls through the cracks while maintaining flexibility to adapt when needed. As Kristen points out during the conversation, this intentionality creates space for both productivity and spontaneity - a balance many professionals struggle to achieve.
For customer success professionals, Kristen's advice is particularly valuable. The demanding nature of client-facing roles often leads to reactive scheduling practices, where calendars become overrun with meetings, leaving little time for focused work. By implementing Kristen's time blocking technique, CS teams can carve out dedicated space for deep work while still maintaining client availability.
What makes Kristen's approach stand out is her holistic perspective - combining personal and professional commitments in a single calendar system. This integrated view prevents the common pitfall of overbooking and creates realistic expectations for what can be accomplished each day. For customer success teams looking to improve efficiency without sacrificing client relationships, this balanced methodology offers a practical framework that can transform productivity.
The customer success playbook continues to evolve, but fundamental skills like time management remain essential building blocks for professional excellence. Kristen's insights remind us that sometimes the simplest strategies yield the most powerful results.
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As artificial intelligence promises to revolutionize project management, many professionals feel caught between excitement and overwhelm. In this AI Friday finale of their three-part series, Kevin Metzger and Roman Trebon explore with Elizabeth Harrin how to harness AI's power without losing the human touch. From security concerns to practical applications, Elizabeth delivers a refreshingly pragmatic approach to integrating AI into your project management toolkit without adding complexity to your already full plate.
Detailed AnalysisThe episode begins with a reality check that resonates across industries: despite AI's massive potential, most project managers aren't using it – primarily due to security protocols and corporate restrictions. Elizabeth's survey findings reveal a gap between AI's promises and its practical adoption, setting the stage for a conversation about realistic implementation.
Rather than pushing for revolutionary changes, Elizabeth advocates for evolution. Her advice? Start with AI functionality already embedded in your existing tools. Microsoft Copilot for meeting summaries, automated task suggestions, and workflow automation represent low-hanging fruit that sidesteps security concerns while delivering immediate value.
Roman's observation about the basics strikes a chord – while early adopters race toward advanced AI applications, many professionals haven't even discovered time-saving fundamentals like automated meeting transcriptions. This highlights a crucial insight: successful AI adoption isn't about chasing the latest technology; it's about finding tools that solve real problems without creating new ones.
Elizabeth's vision for AI focuses on eliminating repetitive work to create space for high-value activities like relationship building and strategic thinking. She paints a picture of AI as an assistant that handles data collection and analysis, freeing project managers to focus on what computers can't do – engage with people and build trust.
The conversation takes a practical turn with specific examples. Imagine uploading a year's worth of monthly reports and asking AI to generate an annual summary – transforming hours of manual compilation into minutes of review. Or consider tools like ClickUp generating task lists from project ideas, or Tom's Planner and Nimble surfacing potential actions from historical data.
Elizabeth's forward-looking perspective is particularly intriguing. She envisions AI analyzing historical performance data to predict deadline reliability – "Kevin has hit his deadlines 3% of the time" becomes actionable intelligence for better planning. While the percentage might sting, the insight enables smarter project management.
The episode concludes with a powerful reminder: AI should support your work, not create more of it. For customer success professionals managing multiple projects, this means choosing tools that genuinely reduce cognitive load rather than adding another layer of complexity to master.
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When multiple projects collide with competing deadlines, stakeholder management becomes an art form. In this dynamic episode of the Customer Success Playbook, Kevin Metzger and Roman Trebon continue their conversation with Elizabeth Harrin, exploring the intricate dance of aligning diverse stakeholder expectations. From financial services to healthcare, Elizabeth shares her cross-industry insights on what truly matters to different stakeholders and how to orchestrate harmony amid chaos.
Detailed AnalysisThe episode opens with Elizabeth's compelling cross-industry comparison that immediately sets the tone for nuanced stakeholder management. Her transition from financial services to healthcare revealed a fundamental truth: what matters most varies dramatically by context. In finance, deadlines reign supreme; in healthcare, quality trumps timing when lives are at stake. This powerful example illustrates why understanding stakeholder priorities isn't just good practice – it's essential for project success.
Elizabeth introduces her stakeholder prioritization grid, a tactical tool that transforms vague relationship management into strategic action. The framework helps project managers navigate the complex web of expectations by first identifying what each stakeholder values most – whether it's time, cost, quality, or social impact. This clarity becomes the North Star for prioritization decisions.
The conversation takes a practical turn with Elizabeth's "Five Email Rule" – a communication strategy that recognizes when digital ping-pong needs to become actual dialogue. After five exchanges, pick up the phone or schedule a meeting. It's a simple yet powerful reminder that efficiency sometimes means stepping away from the keyboard.
Roman's enthusiasm for tactical tools shines through as he highlights the real-world applicability of Elizabeth's methods. This isn't theoretical project management; it's battle-tested wisdom that acknowledges stakeholders are just as overwhelmed as project managers. Elizabeth's solution? Become "easy to do business with" by streamlining communications, creating consolidated reports, and establishing predictable patterns.
The discussion culminates in a masterclass on transparency and trust. When competing demands surface, honest conversations about trade-offs become possible only when you've built that foundation of trust. Elizabeth emphasizes that while you can accomplish anything with enough resources, reality demands smart choices within constraints. By making these constraints visible, project managers empower stakeholders to guide prioritization effectively.
This episode delivers a crucial message for customer success professionals: managing multiple projects isn't just about juggling tasks – it's about orchestrating relationships, understanding diverse priorities, and creating systems that make collaboration effortless.
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Ever feel like you're juggling flaming torches while riding a unicycle? That's modern project management for you. In this episode of the Customer Success Playbook, Kevin Metzger and Roman Trebon welcome Elizabeth Harrin, the mastermind behind the award-winning Rebels Guide to Project Management. With over two decades of experience helping professionals navigate the chaos of multiple projects, Elizabeth reveals her battle-tested strategies for maintaining sanity when the pressure cooker of deadlines starts whistling.
Detailed AnalysisThe conversation kicks off with Elizabeth dropping a truth bomb that resonates across industries: project management isn't just for project managers anymore. Whether you're in customer success, sales, or support, you're likely juggling multiple initiatives that directly impact client satisfaction. The beauty of Elizabeth's approach lies in its simplicity – she transforms overwhelming to-do lists into manageable "buckets of work."
Her number one tip? Start with visibility. Most professionals treat their workload like an endless scroll of doom, but Elizabeth advocates for packaging work into digestible categories. Think of it as Marie Kondo-ing your project portfolio – group by client, deadline, or theme, then ruthlessly prioritize what truly sparks value.
The discussion takes a practical turn when Elizabeth introduces her "top three goals" approach. By identifying three key objectives each evening for the next day, you create a roadmap that prevents the dreaded email rabbit hole. Roman Trebon enthusiastically validates this method, sharing his own success with a similar journaling practice – proof that even the busiest professionals can benefit from this deceptively simple strategy.
What sets this episode apart is Elizabeth's emphasis on personalization. She acknowledges that traditional prioritization models (like the famous "eat the frog" approach) don't work for everyone, especially those with neurodivergence. The key is experimentation – test different systems, keep what works, and adjust what doesn't. This flexible mindset transforms project management from a rigid framework into a dynamic toolkit.
The episode concludes with a compelling reminder: effective project management isn't about doing more; it's about doing what matters. In an era where burnout lurks around every deadline, Elizabeth's approach offers a refreshing perspective on sustainable productivity.
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In this final part of the Katie Smith trilogy on the Customer Success Playbook, we enter the brave new world of AI and marketing. Host Kevin Metzger explores the promises and pitfalls of generative tools with Katie, who brings her thoughtful and grounded take on how businesses can embrace automation while fiercely protecting their authenticity. If you’ve ever wondered how to use AI effectively without sounding like a robot, this one’s for you.
Detailed Analysis: AI isn't going anywhere—and that's exactly why it's time to get strategic. Katie Smith walks listeners through the essentials of adopting AI in a way that enhances rather than dilutes your marketing. The episode kicks off with her advice on building internal AI policies: what your team will use AI for, what it won’t, and how to protect sensitive data along the way. Her mantra? Be proactive, not reactive.
Katie also shares her go-to applications of AI in the creative process:
Use AI as a co-creator to spark content ideas and draft early versionsTrain AI with your brand’s voice and tone to maintain consistencyStay vigilant about hallucinations and homogenized contentShe emphasizes the importance of human review at every stage, especially when publishing customer-facing materials. AI is a brilliant assistant, but not a final authority.
The discussion evolves into deeper insights on lead generation and real-time responsiveness. Kevin adds his own tricks for applying brand tone through prompt engineering and post-processing, offering a compelling use case that blends Claude, GPTs, and content repurposing magic.
Finally, the two zoom out to a broader question: How do you optimize your brand for AI-driven search and recommendations? It’s an emerging discipline with massive implications, and Katie teases what’s to come from leaders in B2B and digital strategy.
Whether you're testing the AI waters or already building internal GPTs, Katie’s thoughtful approach provides the guardrails needed to preserve quality and trust in a world of automation.
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Back for part two with Katie Smith on the Customer Success Playbook, and this time we’re tearing down silos. In this Wednesday edition, host Kevin Metzger guides a conversation focused on how to bring marketing and customer success into harmony. Katie—founder of Wild Path Consulting and fractional CMO—shares a blueprint for unifying teams, streamlining customer journeys, and turning internal collaboration into a competitive advantage.
Detailed Analysis: This episode is less about theory and more about execution. Katie Smith gets candid about why alignment between marketing and customer success isn’t a nice-to-have—it’s the lifeline of sustainable growth. Her argument is clear: the closer these departments work together, the more seamless and authentic the customer experience becomes.
Katie emphasizes that customer success is the closest link a company has to real-time customer sentiment. And yet, too often, that feedback gets lost in the shuffle. Her proposed fix? Cross-functional meetings, shared goals, and a top-down commitment to break the silos. She outlines how marketing can use insights from customer success to better tailor messaging, avoid overpromising, and reinforce consistent value.
The conversation gets practical with ideas on how to structure interdepartmental communication, including:
Setting up regular syncs between CS and marketingReporting loops where both sides share qualitative and quantitative insightsShared definitions of success, ideal customer profiles, and journey checkpointsKatie also urges organizations to think beyond marketing and CS. Sales, product, ops—even the loadout teams in a manufacturing company—all contribute to the customer experience and need to be part of the marketing ecosystem. It’s a holistic view that turns internal collaboration into customer satisfaction.
And if you’ve ever felt the pain of over-promised marketing and under-delivered onboarding, Katie’s advice on co-created alignment is a must-listen.
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This episode of the Customer Success Playbook podcast is a breath of fresh Livingston, Montana air. Kevin Metzger sits down with Katie Smith, fractional CMO and founder of Wild Path Consulting, to unpack how strategic marketing and proactive customer listening can transform customer relationships and drive sustainable growth. Katie dives into tactics that ensure continuous customer engagement, especially in volatile markets, and shares actionable insights on how aligning customer feedback with marketing can unlock next-level success.
Detailed Analysis: Katie Smith's marketing philosophy is simple but potent: Always keep your ear to the ground. As a fractional Chief Marketing Officer, she specializes in building scalable strategies by embedding listening loops throughout the customer lifecycle. In this episode, Katie unpacks the critical role of subtle, continuous feedback gathering—from onboarding questions like "What are you most excited about?" to reflective prompts such as "What has changed the most for you?"
She emphasizes integrating these questions into everyday interactions rather than relying on clunky surveys. It's about embedding marketing intelligence into the customer success function. And here's the kicker: Katie makes a strong case that the insights from customer success should be fueling marketing strategy just as much as sales data does. That shift in mindset helps brands stay ahead of the curve—adjusting messaging, realigning offerings, and reinforcing value in real time.
The conversation also touches on the broader organizational alignment between marketing and customer success teams. With fast-moving market shifts, this collaboration isn’t just beneficial; it’s essential. Katie leaves us with a compelling preview of part two, where the focus sharpens on co-owning long-term value across departments.
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Close out the week with a power-packed episode of the Customer Success Playbook, as Roman Trebon and Kevin Metzger welcome Joe Di Grande for a lively Friday discussion on AI in customer success! Joe shares an honest look at how AI can supercharge your customer success playbook—but only if deployed with clarity and purpose. Learn how to avoid the common pitfall of chasing shiny AI tools without aligning them to your actual goals. From automation to predictive analytics, this episode is a must-listen for forward-thinking CS and product marketing teams.
Detailed Analysis: In a world where every scroll brings a new "game-changing" AI app, Joe Di Grande brings much-needed sanity to the conversation. Returning to the Customer Success Playbook, Joe shares practical ways AI can drive serious gains—faster customer engagement, smarter predictive analytics, better documentation—but not without a word of caution: it's not about the tool, it's about the goal.
Joe lays out a clear decision framework: start by asking what business problem you're solving, measure the potential time savings, and always weigh the cost versus value, much like any traditional tech investment. He shares examples from his own consulting work, including custom GPT bots, clever workflow automation with tools like Tango, and AI-driven stakeholder management.
Kevin and Roman add extra layers of wisdom, emphasizing that AI project evaluation is not fundamentally different from any other project: start with objectives, measure value, manage implementation smartly. Along the way, they give a shoutout to innovative tools like Cast.app and discuss how to stay grounded when AI hype is everywhere.
If you want to integrate AI into your customer success playbook—without losing focus or budget—this episode delivers practical, optimistic, and realistic strategies.
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Gear up for an energizing discussion on tech stacks and smart scaling! In this midweek episode of the Customer Success Playbook, Kevin Metzger and Roman Trebon welcome Joe Di Grande back to tackle a pressing issue: bloated CS tech stacks. Joe shares why so many organizations fall into this trap and delivers actionable advice on how to avoid or fix it. From building cross-functional committees to starting tech ops planning early, Joe's wisdom is essential for anyone striving to build a lean, mean customer success machine.
Detailed Analysis: Joe Di Grande's return to the Customer Success Playbook is like having your favorite professor hand you the cheat sheet to a passing grade. In this session, he unpacks why bloated tech stacks happen: a lack of operational foresight, siloed decision-making, and the absence of data-first strategies. Acquisition fever might keep the lights on, but without systems thinking, organizations find themselves in a tangled mess of redundant tools.
Joe highlights a proactive cure: form a cross-functional committee that includes sales, marketing, CS, and product voices. Bonus points if you find your "ops-minded" champions by tapping the power users of existing tools! His approach is practical, tactical, and refreshingly unpretentious.
For those starting from scratch (aka "dream budget approved!" scenarios), Joe delivers a fantasy list of tech essentials: a reliable CRM, a centralized data warehouse, sales engagement tools, data enrichment platforms, marketing automation solutions, and customer success platforms—all strategically selected to foster scalability and transparency.
Joe’s core advice? Think operations early, communicate often, and let your data be the thread tying it all together. It's a masterclass in balancing ambition with operational excellence for any customer success playbook.
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Ready to rethink your approach to customer success without draining your budget? In this episode of the Customer Success Playbook, hosts Roman Trebon and Kevin Metzger sit down with Joe Di Grande, founder of Joe DE's Tech Touch, to demystify tech touch strategies. Joe shares practical methods for building a tech touch framework even when your data is scattered and your budget is tight. You'll discover how understanding your goals, auditing your current data, and leveraging freemium tools can set the foundation for scalable and impactful customer success initiatives.
Detailed Analysis: Joe Di Grande dives into the evolution of "tech touch" — from a basic method of handling long-tail customer segments to a full-fledged strategic pillar within modern customer success playbooks. He emphasizes that success doesn't start with the fanciest tools but with a clear understanding of your goals and the data you already have. Joe cleverly outlines how even spreadsheet-based strategies can kick off a winning initiative if you keep your eyes on key lifecycle markers like contract dates.
Resourcefulness takes center stage as Joe highlights a roster of budget-friendly tools — including Zapier, Apollo.io, and Tango.io — that can empower even the scrappiest startups to automate engagement and education touchpoints. By focusing first on aligning data and customer lifecycle stages, organizations can set up low-cost experiments that yield big insights and pave the way for future investment in tech success platforms.
Whether you're a startup looking to stretch every dollar or an enterprise recalibrating your customer success operations, this conversation offers a refreshing, grounded take on scaling smartly. Joe's energy and real-world examples make this a can't-miss episode for anyone seeking to modernize their customer success playbook with tech touch strategies.
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In the final chapter of a compelling three-part series on the Customer Success Playbook, hosts Kevin Metzger and Roman Trebon sit down once more with communication strategist Mary Schmid to explore whether artificial intelligence can play a meaningful role in building trust. With AI Fridays in full swing, the conversation veers into uncharted territory: can AI actually help us become better listeners, or are we outsourcing our empathy to machines?
Detailed Analysis: AI in customer success is no longer theoretical; it's operational. From onboarding workflows to meeting recaps, AI is here to streamline. But the question Mary Schmid challenges us with is not can AI help, but how and where should it be used? With characteristic wit and wisdom, she makes it clear: AI can emulate empathy, but it can't feel it. The result? AI may simulate care, but it can’t substitute human connection.
The group reflects on how AI, while useful for efficiency and summarization, may inadvertently encourage disengagement. Roman candidly shares how AI-generated transcripts have made him a lazier listener—a relatable confession for many knowledge workers navigating tech overload. Mary counters with a powerful reminder: presence is a choice. No matter how smart your tools, nothing replaces being fully in the conversation.
This episode offers a practical and philosophical blueprint for integrating AI responsibly. Use it for insights, yes. Use it for speed, definitely. But never let it replace your human instinct to connect. Mary leaves us with a challenge: show up with your eyes, ears, and heart—because no algorithm can replicate that.
Bonus treat: Mary created a downloadable resource exclusively for Customer Success Playbook listeners. Grab it at maryschmid.com/csb — it includes free resources and even complimentary access to her book.
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Strap in for another riveting episode of the Customer Success Playbook, where empathy isn’t just a buzzword—it’s a business advantage. Hosts Kevin Metzger and Roman Trebon are once again joined by communication maven Mary Schmid, who unpacks the neurological power of empathy and its pivotal role in client trust and loyalty. From the depth of scuba diving to the magic of emotional connection, Mary shares how listening with genuine curiosity can shift even the most transactional relationships into long-term partnerships.
Detailed Analysis: In this Wednesday "One Big Question" edition, the trio explores how empathy drives client loyalty, especially in high-stakes sectors like finance. Mary challenges the misconception that empathy is about agreement, reframing it instead as a courageous act of understanding. Through her neuroscience-informed approach, she explains how empathy fosters psychological safety, laying the groundwork for trust.
The conversation ventures into practical insights for customer success professionals: the importance of leading with emotional curiosity, the discipline of "listening to connect," and how to gracefully introduce differing perspectives once mutual understanding is established. Mary introduces a powerful sequence: empathy first, connection second, and then collaboration. The episode highlights that curiosity and compassion aren’t liabilities—they are strategic tools.
Also discussed: how leaders can break free from monologue mode by shifting into learner mode, and how to handle moments when your perspective diverges from the client’s. Spoiler: it involves asking permission to share, not bulldozing your view across the conversation table.
Roman humorously pitches Mary for a bigger stage beyond customer success, and honestly, we agree.
The bottom line? Connection comes before correction. Action comes after understanding.
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In this high-impact episode of the Customer Success Playbook, hosts Kevin Metzger and Roman Trebon welcome Mary Schmid, MBA, a communication and leadership expert with a passion for rewiring how we listen. Mary reveals how to shift from surface-level exchanges to trust-building dialogues by embracing her "Conversational Edge" framework. Rather than defaulting to advice-giving, Mary urges professionals to pause and lean into connection-first listening. With a foundation in neuroscience, she explains how we unconsciously drop out of conversations every 12 to 18 seconds—and how to stay tuned in. If you think you’re a good listener, this episode might surprise you.
Detailed Analysis: This episode flips the script on what it means to be a "trusted advisor." Mary Schmid argues that client relationships are often eroded by a focus on proving expertise instead of demonstrating care. Using brain science as a guide, she introduces the idea that effective listening triggers the brain’s trust response. Listeners are walked through a conversational sequence that begins with understanding the situation, moves into exploring the client’s thoughts and emotions, and culminates in assessing the impact. The goal? Helping clients feel heard, not herded.
Mary deftly explains how traditional expertise-driven dialogue creates power imbalances, pushing clients into defensive, disengaged states. In contrast, her approach taps into the oxytocin-powered trust circuit by creating psychological safety. The episode offers practical examples and humorous insights—including Kevin getting called out for zoning out every few seconds (we’re looking at you, Kevin).
For business leaders and customer success professionals, Mary provides a vital reminder: real influence stems from emotional connection, not intellectual superiority. When you guide a client into collaborative discovery, rather than corner them with solutions, you spark engagement and build lasting loyalty.
Her parting wisdom? Respect begins with listening to connect, not correct.
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You can also find the CS Playbook Podcast:
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Twitter - @CS_Playbook
You can find Kevin at:
Metzgerbusiness.com - Kevin's person web site
Kevin Metzger on Linked In.
You can find Roman at:
Roman Trebon on Linked In. -
Send us a text
In this forward-looking Friday edition of the Customer Success Playbook, Cairo Marsh returns to round out his trilogy of episodes with a critical discussion: can artificial intelligence enhance empathy in customer experience, or does it risk eliminating the human touch? Cairo, Roman, and Kevin dive into the real-world uses of AI in sentiment analysis, automation, and service design, exploring when and how AI tools can be customer-centric rather than just cost-centric. From call centers to cultural nuance, this conversation balances optimism with realism.
Detailed Analysis: The final installment in Cairo Marsh's series on the Customer Success Playbook podcast explores the intersection of artificial intelligence and empathetic customer experience. While AI is often championed for its efficiency and cost-saving potential, Cairo is quick to caution that most implementations prioritize business needs over customer value—a misalignment that risks undermining trust.
He argues that true empathy-driven AI must empower the customer, not just the brand. The conversation unpacks this idea with practical examples: AI as a helpful tool for low-value, transactional queries ("Did my payment clear?") versus high-emotion, high-stakes moments ("I’ve been in a car accident"), where human connection is irreplaceable. The team discusses the strategic importance of context in deciding where AI belongs.
But the episode doesn't stop at critique. Kevin and Roman offer ideas on human-AI collaboration—pairing agents with AI copilots to enhance real-time service without sacrificing warmth. Cairo reinforces that the real opportunity lies in using AI to support customers on their terms, not as a substitute for authentic engagement.
In a surprisingly touching moment, Cairo shares a story from a bank in Taiwan, illustrating that sometimes, the most valuable service is simply human presence. As businesses embrace automation, remembering our innate desire for connection may be the key to designing AI with empathy.
This episode challenges us to ask: Is your AI working for you, or for your customers?
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You can also find the CS Playbook Podcast:
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Metzgerbusiness.com - Kevin's person web site
Kevin Metzger on Linked In.
You can find Roman at:
Roman Trebon on Linked In. -
Send us a text
In this midweek edition of the Customer Success Playbook, Cairo Marsh returns to the mic to explore the layered world of empathetic marketing across cultures. From the Bronx to Tokyo, Cairo's lived experience adds a global lens to his practical insights on designing connection-first marketing strategies. He unpacks how empathy drives retention, not just acquisition, and reveals a three-tiered framework for building brand relationships based on product, brand identity, and social capital.
Detailed Analysis: Cairo Marsh is back for part two, and the conversation dives even deeper. What begins as a lighthearted exchange about food adventures in Tokyo quickly transforms into a tactical discussion on what it means to build marketing strategies that resonate across diverse cultural contexts.
The heart of this episode lies in Cairo’s model of connection:
Functional (product value)Emotional (brand resonance)Social (status or identity alignment)By structuring messaging and experiences around these layers, brands can meet customers where they are—geographically and emotionally. Cairo shares how this model works globally, with examples from his own bi-continental agency experience.
But Cairo doesn’t stop at strategy. He addresses the million-dollar question: how do you measure the impact of empathy? His answer is both practical and powerful: combine transactional data with perceptual insights to understand not just what customers do, but why they do it. That "why," he argues, is the leading indicator of business success.
Crucially, the episode draws a bridge between marketing and customer success. Cairo emphasizes that empathy shouldn’t end at conversion. It's the glue that holds the entire post-sale journey together—retention, loyalty, and advocacy all benefit when brands treat customers like humans, not just metrics.
This conversation is a masterclass in global customer connection and a blueprint for embedding empathy across every phase of the customer journey. It’s also a prelude to the next episode, where Cairo returns to unpack how AI fits into the empathy equation.
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You can also find the CS Playbook Podcast:
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You can find Kevin at:
Metzgerbusiness.com - Kevin's person web site
Kevin Metzger on Linked In.
You can find Roman at:
Roman Trebon on Linked In. -
Send us a text
This episode of the Customer Success Playbook welcomes Cairo Marsh, Founder and Executive Partner of Relative, for a thought-provoking conversation on empathy-led marketing. Cairo shares his top tip for organizations seeking to harness empathy as a competitive advantage: focus on value at every touchpoint. From Patagonia's purpose-driven branding to the basics of transactional incentives, Cairo offers real-world examples of brands that resonate by placing customer needs front and center. It's not just marketing—it's relationship building at scale.
Detailed Analysis: In this crisp yet powerful episode, Cairo Marsh challenges traditional marketing mindsets by reframing empathy as a strategic asset rather than a soft skill. He lays out a pragmatic approach to empathetic marketing that begins with a deceptively simple question: "What does your audience need right now?" It's not about gimmicks or grand gestures but about delivering meaningful value at every interaction.
Using brands like Patagonia as a compass, Cairo underscores how value can transcend the transactional. Patagonia's commitment to sustainability offers customers purpose beyond product—a model for values-driven engagement that earns loyalty. On the flip side, Cairo doesn’t shy away from acknowledging that even simple sweepstakes or incentives can serve as valid forms of value, as long as they're designed with the customer's benefit in mind.
The conversation also touches on the psychological shift needed within companies. Empathy isn't a campaign—it's a culture. And it begins with a genuine interest in your customer’s world. Cairo likens this to personal relationships, where curiosity and attentiveness build trust. Businesses should behave less like sociopaths (his words, not ours) and more like thoughtful partners.
Whether you're building a brand or fine-tuning your customer journey, this episode is a potent reminder: empathy scales. It informs marketing, strengthens loyalty, and enhances every element of the customer success playbook.
Now you can interact with us directly by leaving a voice message at https://www.speakpipe.com/CustomerSuccessPlaybook
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You can also find the CS Playbook Podcast:
YouTube - @CustomerSuccessPlaybookPodcast
Twitter - @CS_Playbook
You can find Kevin at:
Metzgerbusiness.com - Kevin's person web site
Kevin Metzger on Linked In.
You can find Roman at:
Roman Trebon on Linked In. -
Send us a text
In the final episode of this powerful three-part series, the Customer Success Playbook Podcast welcomes back Shep Hyken for a forward-looking discussion on AI's role in customer experience. From customer trust and chatbot misfires to the fear of messing up (FOMU), Shep breaks down the opportunities and pitfalls of artificial intelligence in service.
Detailed Analysis: Kevin Metzger and Roman Trebon wrap up the Shep Hyken trilogy with a candid conversation on how AI is both transforming and challenging the customer service landscape. While 68% of customers still prefer phone support, Shep’s latest research reveals a promising shift: 50% of consumers have successfully resolved issues with AI-driven support. But there's a catch—another 50% report being misled by AI.
That duality sets the stage for Shep’s deeper message: AI must offer convenience without creating confusion. The brands that win will be those who design seamless handoffs to humans when bots fall short, and those who tailor support channels based on customer demographics. Shep emphasizes that CX isn't about chasing tech trends—it's about knowing your customer and building trust at every touchpoint.
He introduces a key fear hindering AI adoption: not FOMO (fear of missing out), but FOMU—fear of messing up. Many organizations hesitate to modernize due to sunk costs in legacy tech or risk aversion among leadership. But as Shep points out, the true risk is falling behind the expectations set by the best experiences customers have had—regardless of industry.
As a bonus, Shep shares where to find his expansive research, including his 2025 State of Customer Service and CX report, freely available at https://hyken.com/research/.
This episode is essential for any business leader looking to leverage AI wisely and responsibly in the age of customer experience.
Now you can interact with us directly by leaving a voice message at https://www.speakpipe.com/CustomerSuccessPlaybook
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You can also find the CS Playbook Podcast:
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You can find Kevin at:
Metzgerbusiness.com - Kevin's person web site
Kevin Metzger on Linked In.
You can find Roman at:
Roman Trebon on Linked In. - Laat meer zien
