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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 Analysis

Building 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 Analysis

Effective 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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You can also find the CS Playbook Podcast:
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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 Analysis

The 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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Kevin Metzger on Linked In.

You can find Roman at:
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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 Analysis

The 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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You can also find the CS Playbook Podcast:
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Kevin Metzger on Linked In.

You can find Roman at:
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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 Analysis

The 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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Kevin Metzger on Linked In.

You can find Roman at:
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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 versions
• Train AI with your brand’s voice and tone to maintain consistency
• Stay vigilant about hallucinations and homogenized content

She 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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Kevin Metzger on Linked In.

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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 marketing
• Reporting loops where both sides share qualitative and quantitative insights
• Shared definitions of success, ideal customer profiles, and journey checkpoints

Katie 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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You can also find the CS Playbook Podcast:
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You can find Roman at:
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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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You can also find the CS Playbook Podcast:
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You can find Kevin at:
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Kevin Metzger on Linked In.

You can find Roman at:
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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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You can also find the CS Playbook Podcast:
YouTube - @CustomerSuccessPlaybookPodcast
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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.