The Thoughts on Selling™ Podcast

In this episode of Thoughts on Selling, I sit down with Ted McKenna — researcher, author, and co-creator of some of the most influential sales frameworks of the past two decades. Ted has been behind The Challenger Sale, The JOLT Effect, and most recently, The Activator Advantage.We dive into the evolving dynamics of B2B sales, why buyers are more informed (and more hesitant) than ever, and what high-performing sellers do differently.Some highlights from our discussion:Data meets sales anthropology. Ted shares how deep analysis of 2.5 million sales calls revealed why more deals end in “no decision” — and what sellers can do about it.The JOLT Effect in practice. Why too much information overwhelms buyers, and how great sellers guide decisions rather than flood inboxes with decks.The Activator Advantage. A deep look at what makes “activators” so successful — consistent business development, building zipper relationships, and flowing value across networks.Fear of messing up. Discounts don’t move deals — risk and career impact do. Sellers must address the emotional side of decision-making.Authenticity wins. Buyers can spot when you’re coin-operated. The best sellers genuinely care about client outcomes and align their work with customer missions.We also touch on AI’s role in selling, improv as sales training, and the timeless truth that how you sell matters more than what you sell.🎧 This is one you’ll want to play back with your team.#salesenablement #jolteffect #activatoradvantage #salescoaching #thoughtsonselling

In this episode of Thoughts on Selling, I sit down with AI strategist and workforce transformation expert Ben Tasker. Ben has spent over a decade helping organizations harness AI not just as a shiny tool, but as a way to amplify human abilities through upskilling, reskilling, and smarter systems thinking.We dive into:The “AI Between Times”: why we’re in a transition period where adoption is fast, mistakes will happen, and systems thinking is essential.Upskilling & Reskilling: how organizations can build learning plans to keep talent relevant and amplify what people already do well.Applied AI in Sales: from RFP prep to simulated buyer conversations, how sales teams can use AI for deliberate practice and better customer engagement.Systems Thinking & Change Management: why AI adoption fails without clear processes, data quality, and organizational alignment.Personal Branding in the AI Era: how individuals can leverage AI to publish, create, and stay visible in a world where recommendation engines drive discovery.Ben makes a strong case: While AI won’t replace us— those who embrace it will win over those who don’t.If you’re a sales leader, enablement pro, or individual contributor wondering how to stay relevant in this exponential era of change, this conversation is for you.👉 Connect with Ben at bentaskerai.com

In this episode of Thoughts on Selling, I sit down with Britt White—sales leader, edtech evangelist, former VP of Sales at SmartPass, and a force of nature when it comes to bringing passion to work.This isn’t a scripted “how-to” chat. It’s a real conversation between two humans unpacking what it means to love what you do—and how that love shows up (or doesn’t) in sales, leadership, and culture.🔥 Key TakeawaysPassion isn’t optional—it’s fuel. Passion doesn’t just live inside us—it’s contagious. Britt talks about how her energy draws people in, builds trust, and lifts her teams.Process enables freedom. Passion without process? Chaos. But the right systems let us lead, coach, and innovate without falling into micromanagement.Leadership and management are not the same. Britt puts it clearly: “If I have to manage you, I’m probably managing you out.” Leadership is about direction and inspiration, not control.Curiosity keeps the work fresh. We talk about how early career environments often crush curiosity—but the best sellers never stop asking questions or challenging assumptions.Break the routine. Britt runs cold call power hours with her team sitting on the floor, snacks in hand. It shifts the vibe, lowers pressure, and opens people up.Comfort breeds confidence. Whether it’s taking my shoes off before a keynote or visualizing a client’s challenge like it’s my own—getting grounded helps me show up as my best self.Question the sacred cows. From SKOs to quotas, we ask: do we do this because it works—or because it’s just always been done?💭 One idea to try this week:Take something routine—your next 1:1, your team huddle, your practice session—and flip it. Sit on the floor. Skip the slides. Shake it up. See what changes.🎧 Listen in if you’re into:Leading with heart, not controlSales teams that actually careEdtech sales and mission-driven workDitching the mask and doing work that matters👋 You can find Britt on LinkedIn here—and if you’re thinking about working with her, get to know her in person before listening. Trust me—it’ll hit different.Thanks for listening—and remember: get comfortable-er.—Lee

In this episode of Thoughts on Selling, I sit down with Jake Isham — filmmaker, creative director, and founder of Creative Minds Agency.Jake’s story is pure art-meets-entrepreneurship. He started as an actor, moved behind the camera to direct, and somewhere along the way became what he calls an “accidental marketer.”We dig deep into the intersection of storytelling, sales, and authenticity — how great art and great selling share the same purpose: to create an effect. Jake explains how the best salespeople are actually performers — not in a fake way, but in the sense that they listen, adapt, and stay present in the scene.Our conversation bounces between filmmaking, improv, and enterprise sales, but it all comes back to one central idea: sales is an art form. The goal isn’t to pitch harder or talk faster; it’s to create a feeling that sticks.A few big takeaways:🎭 Sales and acting share the same core skill — presence. Great sellers listen, improvise, and respond in the moment.💬 Be interested, not interesting. Shift the spotlight to the customer; that’s where trust begins.🧠 Reps build mastery. Like athletes and artists, salespeople get better through repetition and reflection — not theory.🔥 Authenticity beats polish. When you lead with genuine curiosity and passion, selling stops feeling like selling.🎥 Personal brand is leverage. Jake shows how documenting your story builds trust and visibility that lasts beyond any one deal.💡 The right views matter more than viral views. You don’t need a million followers — you need the right audience.Jake and I also talk about the business of creativity — how he learned to blend craft with commerce, the value of expertise (“knowing where to tap”), and why every creator, seller, and leader needs to believe in what they’re offering.It’s a fun, high-energy conversation about where art meets revenue — and how showing up as yourself is the real competitive edge.🎧 Give it a listen, and let me know what lands with you.#SalesLeadership #PersonalBranding #AuthenticSelling #Storytelling #ThoughtsOnSelling

In this episode of Thoughts on Selling, I sit down with Laura Keith, CEO of Hive Perform and Hive Learning — and self-proclaimed “Chief Entertainment Officer” of three kids. We dig into the psychology of selling, the human side of enablement, and how data, AI, and coaching are reshaping modern sales.Laura’s journey from studying psychology to leading sales organizations is fascinating. She never planned to work in sales — but curiosity, empathy, and a deep understanding of human behavior naturally pulled her in. Those same traits now shape her leadership and the products she’s building at Hive Perform.We talk about how sales has lost touch with its human side — too often focused on product features and process over people — and how AI might actually help bring humanity back into selling. As automation handles more of the science, the art becomes more valuable: listening deeply, reading motivation, and understanding buyer psychology.A few big takeaways from our conversation:Sales is psychology. Understanding what makes buyers tick — their motivations, fears, and goals — is at the heart of effective selling.AI can’t replace empathy. The best sales reps will use AI as a tool but rely on human insight and curiosity to create connection.Coaching and practice drive performance. The highest-performing teams make time to practice and coach — not just inspect pipelines.Leaders must define “what good looks like.” Without clear frameworks, coaching and development can’t happen effectively.Data makes conversations objective. When performance data is visible, reps and leaders can focus on solving problems together, not defending opinions.Curiosity beats scripts. Great sellers ask one more question instead of firing back with a pre-rehearsed answer.We wrap by talking about the future of sales enablement — one where data, AI, and human insight combine to make teams more adaptable, empathetic, and effective.🎧 Give it a listen — and let me know what resonates most with you.#SalesEnablement #SalesLeadership #AIinSales #PsychologyofSelling #ThoughtsOnSelling

In this episode of Thoughts on Selling, I sit down with Jeff Kirchick — sales leader, author, and big believer in authenticity. We dig into how authenticity plays out in sales, what AI can and can’t replace, and why building trust matters more than ever.Jeff shares his journey from English major and aspiring screenwriter to startup sales leader, selling seven-figure deals to Fortune 500s. We talk about his book, the hard truths he learned writing it, and why he believes authenticity is the ultimate differentiator in a world where AI can generate scripts, emails, and playbooks.We get into some fun and unexpected territory too — from Dennis Rodman and Larry David as surprising role models for authenticity, to the cultural differences between selling in Boston, Japan, and Boulder. The through-line? Real relationships, built on curiosity, honesty, and non-attachment to outcomes, are what drive sustainable success in sales.A few key takeaways:Authenticity builds trust. Buyers can tell when you’re real — and they reward it.AI can’t replace relationships. Tools help, but risk management and shared experience still come from humans.Deliberate practice matters. Salespeople need to rehearse pivots and build confidence outside scripts.Non-attachment to outcomes frees you. Curiosity and care create openings, even if they don’t lead to immediate deals.Great leaders go first. Vulnerability and empathy from the top invite teams to bring their full selves.This conversation is packed with stories, insights, and practical wisdom for anyone looking to level up as a sales leader or seller.🎧 Give it a listen, and let me know what lands with you.

In this episode of Thoughts on Selling, I sit down with David Donlan, VP of Sales at IP Co-Pilot, longtime tech sales leader, and passionate mentor for the next generation of sales professionals.David and I cover a wide range of topics — from his early days upselling azaleas with fertilizer at age 15 to shaping sales teams at HubSpot, and now building a company that helps innovators protect and accelerate patents.A few highlights from our conversation:Three ways to sell. David breaks down selling on product (easy but competitive), outcomes (about solving real business problems), and feelings (the hardest, but most powerful when done well).The heart of leadership. Why helping SDRs and junior salespeople grow into leaders is one of the most rewarding parts of a career.Hiring with discipline. Scorecards, structured onboarding, and clear expectations turn hiring from a gamble into a repeatable, measurable process.Culture in action. It’s not about slogans on the wall; it’s about building a place where individual motivations are recognized and supported.From landscaping to leadership. How lessons from selling plants, teaching swim lessons, and working in services carried forward into leading tech sales organizations.David also shares his excitement about IP Co-Pilot — and how reducing the patent process from years to weeks can completely change the trajectory of companies large and small.This one’s packed with stories, lessons, and practical ideas you can put into play immediately.🎧 Tune in — and let me know which part resonates most with your sales journey.#SalesLeadership #SalesEnablement #TeamBuilding #ThoughtsOnSelling

In this episode of Thoughts on Selling, I sit down with Mike Baron — longtime sales leader, mentor, and operator who has lived the startup, PE, and enterprise trenches. Our conversation is part playbook, part reality check, and packed with practical wisdom for anyone leading or enabling sales teams.We dive right into a “what if” scenario: if Mike were CRO and I were head of sales enablement at a security startup, what would we do first? Mike breaks it down with clarity:Start with comp plans. Keep them simple, transparent, and behavior-driving. A clear plan motivates, while a 65-page manual kills performance.Talk to customers — and closed-lost deals. Understand where you win, where you lose, and why. The gold is in the feedback loop.Assess the tech stack. Too many tools = administrivia. Too few = inefficiency. The goal: help reps spend more time selling.From there, we cover the importance of defining an ICP that’s not just a “total addressable market” (because “anyone between 200 and 2,500 employees” isn’t a strategy). We talk about how to apply the “hive mind” to big deals by letting reps present stuck opportunities for group problem-solving.We also dig into value selling: moving past feature talk to true business outcomes — revenue growth, OPEX reduction, market expansion. Mike shares how coaching, role play, and peer-led conversations shift reps into those business-focused dialogues.A few key takeaways:Comp drives behavior. A well-built plan aligns sellers, customers, and company goals.Feedback is fuel. Win/loss analysis and customer conversations sharpen the value prop.Simplify to amplify. Tech should serve sellers, not bury them.Deliberate practice matters. Just like athletes, reps need repetition and coaching to build muscle memory.Celebrate the whole team. SEs, rev ops, legal — reward them too, not just quota carriers.This is a fun, wide-ranging conversation full of actionable ideas. If you’re leading a team, building enablement, or just want to sharpen your own selling, you’ll take something useful away.🎧 Tune in — and let me know what resonates most.#salesleadership #salesenablement #valueselling #thoughtsonselling

In this episode, I sit down with Matt Wilkinson — life sciences marketer turned AI strategy partner, Visiting Fellow at Cranfield School of Management, and board member at the Association of Key Account Management. Matt brings a sharp lens to the challenges of sales and marketing alignment, the rise of AI in B2B, and what it really takes to create customers in today’s environment.We cover a wide range of topics, from why account-based approaches are so powerful when done right, to how culture inside organizations shapes buying behavior, to the shifting role of brand and trust in an AI-driven world.Some key takeaways from our conversation:Sales + Marketing must share the same North Star. Vanity metrics and siloed KPIs create friction instead of customers.Account-based strategy works best when sales and marketing co-create it. Alignment starts with shared target accounts, shared narratives, and shared wins.AI is rewriting the buying journey. Buyers come to conversations armed with custom, AI-generated insights — which means sellers need a point of view, not just information.Brand still matters. Even in a digital-first, bot-enabled world, strong brands reduce perceived risk and influence decisions.Know your customer deeply. Visit them, learn their culture, and align your story to their mission — whether that’s patient outcomes, revenue growth, or reducing risk.Trust and human connection win. Efficiency is not effectiveness; one meaningful, risk-reducing conversation beats 10,000 shallow ones.Matt’s blend of academic insight, practical experience, and stories (yes, even about coffee makers!) makes this a conversation packed with perspective for anyone navigating modern B2B sales and marketing.🎧 Give it a listen — and let me know what resonates with you.#sales #marketing #AI #accountbasedmarketing #thoughtsonselling

Tracy Linne, an experienced sales leader and strategist, joins me for a powerful conversation on the intersection of leadership, clarity, and sales performance for this episode of the Thoughts on Selling podcast.Tracy emphasizes the role of leaders in shaping not just strategy but belief within teams. Our discussion covers the importance of creating clarity in complex environments, the necessity of building trust as the foundation for growth, and why adaptability is a hallmark of modern sales leadership.Key insights include:Sales as an energy exchange. Leaders must embody the inspiration they want their teams to deliver.The power of simplicity. Clear direction removes friction and accelerates execution.Trust as a multiplier. High-trust environments drive accountability, creativity, and resilience.Leadership by example. The behaviors modeled by leaders set the cultural tone.This episode is particularly relevant for sales executives, revenue leaders, and anyone navigating the challenges of leading high-performing teams in dynamic markets.🎧 Tune in and discover how Tracy’s insights can sharpen your leadership approach.#salesstrategy #leadership #salesenablement #growthmindset #thoughtsonselling

For this episode I’m joined by Vance Morris—a guy whose journey goes from rock bands to Disney to running premium home services, and now helping businesses “Disney-fy” their customer experience. And let me tell you, the parallels to sales are everywhere.If you’re in sales and think “customer experience” doesn’t apply to you—this episode will change your mind.✅ Systems Create Freedom… and Room for DelightAt Disney, every detail is scripted and systematized so cast members can focus on the magic. It’s the same in sales: if you’ve got your basics dialed in—your research, your process, your CRM—you’re free to actually connect with buyers and deliver value instead of scrambling.✅ First and Last Touches Make or Break YouDisney obsesses over the first impression (parking, music, greetings) and the final moment (fireworks). As salespeople, our first touch is the brand experience. Whether it’s an email, call, or meeting, buyers decide quickly whether they trust us—or not. And how we end a conversation matters just as much.✅ Experiences Beat TransactionsVance’s carpet cleaning business sends a $5 gift box to every customer—just a small delight that led to a 26% increase in higher-tier sales. In sales, it might be a thoughtful follow-up, a handwritten note, or sending a “lumpy mail” package that stands out. It’s about making buyers say: “These people are different.”✅ Don’t Race to the BottomSalespeople who lead with discounts or lowest price become commodities. Vance urges businesses to charge for the experience they deliver. In sales, we need to sell on value, not price—and confidently walk away from bad deals.✅ Retention > AcquisitionIt costs Vance $135 to get a new customer, but only $22 a year to keep one. Salespeople too often chase new logos and forget that existing customers are way more profitable. Delight your customers, and they’ll stay—and buy more.✅ Delight = RevenueDisney servers giving FastPasses to stressed-out families is a perfect metaphor for sales: solve problems proactively, even ones that “aren’t your department.” It builds loyalty, trust, and bigger deals.We also dig into:Creative ways to stand out (cowbells, coffee mailers, even rubber feet for “getting a foot in the door”)Why salespeople should never be boringWhy “what would Grandma do?” might be the best sales strategy everThe real meaning of primacy and recency in sales conversationsWhy you should never assume buyers think like you doBottom line: As salespeople, we’re in the experience business. Every touchpoint is your chance to create delight—and separate yourself from the crowd.Get more from Vance:→ Grab his free guide: 52 Ways to Wow Without Breaking the Bank→ Check out his business and Disney bootcamps: deliverservicenow.comThanks, Vance, for an awesome conversation that’s pure gold for anyone selling anything!#Sales #CustomerExperience #RevenueGrowth #DisneySecrets #ThoughtsOnSelling

This episode was an absolute blast. I’m joined by Guy Rubin, CEO of Ebsta, who brings not just revenue intelligence expertise—but also a love of physics, football (the British kind), and skiing—to the conversation.We talk about the problem that’s plagued sales teams for decades: data that’s incomplete, inaccurate, or invisible. Guy shares how Ebsta evolved from solving Salesforce data issues into building a revenue intelligence platform that helps companies truly understand what’s driving wins—and where deals stall.Some of the big takeaways from our chat:✅ Your CRM isn’t the whole truth. Email, calendars, and “hidden” stakeholder interactions hold critical data about deals. Mining that signals where opportunities are real—and where they’re just wishful thinking.✅ Sales is the last department to get truly data-driven. Imagine marketing running on gut feel—it’s unthinkable. Sales orgs need to catch up.✅ B and C players can level up. Guy makes a strong case that coaching and data insights—not just “cutting the bottom third”—can help more reps replicate A-player behavior.✅ Pipeline inspection needs consistency AND context. It’s not enough to follow a checklist; you need to tie activities and engagement to outcomes you can actually prove.✅ Discovery is co-creation. We both rant (a bit) about how discovery is more than just running through questions. It’s a collaborative process that evolves throughout the deal.✅ Retention > new logos (sometimes). Ebsta’s data shows that in B2B SaaS, existing customers generated more new revenue than new logos last year. The key? C-level engagement during QBRs.We geek out about pipeline forecasting, coaching, the role of RevOps, and why “happy ears” still kill deals. Guy also shares fascinating benchmarks—like how engaging six stakeholders (including finance and a C-level exec) in stage two of a deal can nearly triple win rates.Guy’s message is clear: Sales can (and must) become data-driven if we want predictable, scalable growth.Check it out—and let me know which insights resonate with you most!#sales #revenuestrategy #salescoaching #salesenablement #revenueintelligence #thoughtsonselling

On this episode of Thoughts on Selling, I sit down with Jackie Retig, a passionate sales enablement leader and COO at EnableWorks. Jackie recently made the leap into entrepreneurship after years in the tech space, and she brings a grounded, practical perspective to what it really takes to build consistent, scalable sales teams.We get into why enablement is more than just onboarding and training—it's about creating the conditions for consistency, repeatability, and predictability in your sales org. Jackie and I talk about the transformation that comes from good enablement, how to help reps lean in and grow, and why the founder-led sales playbook doesn’t scale.We also dive into:Why enablement is finally being seen as a force multiplier by CROs and VPs of SalesHow tribal knowledge is great—but institutional knowledge winsWhat makes discovery truly impactful (hint: it’s not about checking boxes)Why AI is an assist—not a substitute—for great sellingThe power of deliberate practice and role play in building sales muscleKey takeaways:🎯 Consistency, repeatability, and predictability are the north stars of effective enablement.🔁 Discovery isn’t a stage—it’s a mindset. Great sellers co-create value throughout the sales process.⚙️ AI can streamline the busywork, but insight and connection still require the human touch.💡 Sales enablement isn’t just tactical—it’s transformational when tied to business outcomes and measured impact.Whether you're in enablement, sales leadership, or building out your first team, Jackie’s insights on modernizing and scaling sales efforts are well worth your time.

In this episode of Thoughts on Selling, I sit down with Borja Cuan, co-founder of Four15 Digital, to talk all things demand gen, agency life, and what it takes to deliver results—not just leads. Borja's been in the digital marketing game since the late '90s, and his perspective on execution, transparency, and the importance of asking the right questions is both refreshing and, frankly, necessary in today’s B2B landscape.We dig into the realities of running a growth agency in a high-pressure environment, including the need to go deep with clients—not just generate leads and toss them over the fence. Borja shares how they push for real alignment and results, why communication is everything, and how referrals and transparency build trust in an industry plagued by skepticism.We also talk about the importance of recognizing client pressure, being honest about what’s working (and what’s not), and how to keep your team focused on delivering high-quality outcomes every single time.Oh, and we had some laughs too. That’s always part of the plan.Execution is everything. Tools and platforms are accessible to all—it's what you do with them that sets you apart.Leads ≠ Results. Agencies need to care about what happens after the lead is generated.Communication wins. Weekly check-ins, note-takers, action items—it's the small things that keep relationships strong.Referrals help, but trust is earned. Even warm intros come with skepticism. Be ready to prove yourself.Curiosity matters. Ask why something’s working. Or not. Dig deep into the data and the client's goals.Push back (respectfully). If a client’s idea isn’t the best for their business, say so.Ask your clients: What are we not doing today that you wish we were?Get clear on what success looks like—then document it, track it, and revisit it often.Keep your "house" (aka accounts and campaigns) clean—small details build (or break) trust.Set up a regular client health score review—don’t assume silence means satisfaction.Don't just celebrate wins—use them to reinforce value and deepen the relationship.🔑 Key Takeaways✅ Action Items

In this episode, my good friend Alistair Corrie and I take a deep dive into toe topics of mindset, mastery, and how we get out of our own way—whether in selling, sports, leadership, or life.Alistair draws from a range of disciplines—The Inner game, Zen and the Art of Motorcycle Maintenance, martial arts concepts like Shu-Ha-Ri-Kokoro, Viktor Frankl’s logotherapy, and more—to explore what mastery really looks like and how we can create environments where people discover their own paths to skill and flow.We also talk about the role of limiting beliefs, deliberate practice, and why sometimes letting go of “the box” entirely is more powerful than trying to think outside of it.This one is about sales, but also about life—and about how the stories we tell ourselves shape what’s possible.🔑 Key takeaways:Mastery is letting go, not adding more. Concepts like Shu-Ha-Ri-Kokoro remind us that mastery comes from unlearning and allowing—not forcing.Limiting beliefs are often invisible. Sometimes it takes intentional “intervention” to see where old programming is running in the background.Curiosity unlocks creativity. In sales (and beyond), focusing on the customer’s world—not your product’s facts—leads to more authentic conversations and better outcomes.Whether you're a seller, a coach, or someone on a path of personal growth, there’s plenty in this episode to chew on.Thanks as always to Alistair for another thoughtful, wide-ranging conversation. We’ll be continuing this thread in future episodes—stay tuned.

For this episode, I had the pleasure of chatting with David Kirkdorffer — marketing veteran, recording artist, hat enthusiast, and self-proclaimed connective tissue between sales and marketing. We talked all about how sales and marketing can actually get along, the evolution of enablement, and what happens when buyers (and AI) start running the show.🔑 Key Takeaways from Our Conversation:Sales and marketing should be alliesDavid and I have both seen our fair share of friction between the two functions, but alignment starts with empathy. He shared how marketing should serve sales like a customer — and how simplifying CRMs, decluttering processes, and building real relationships makes a huge difference.We're not in a sales-led world anymoreThe buyer journey has changed — again. Buyers want to self-educate. They're forming shortlists before they ever talk to a rep, and in many cases, the first vendor they speak to is the one they buy from. So your content better be out there, and it better be useful.From Sales Enablement → Buyer Enablement → AI EnablementWhile sales enablement is still necessary, if you're not building content that helps buyers make confident decisions on their own, you're missing the mark. Oh, and now we’ve got LLMs and AI agents becoming buyer research tools — so your content needs to be LLM-ready too.Dark social isn’t so dark anymoreYour buyers are hanging out in Slack groups, Zoom communities, and private DMs — not your lead forms. Attribution is a mess, but influence is real. The best way to stay visible? Build for discoverability. That means un-gating helpful content and optimizing for the new “search” — LLMs and AI summaries.Startups and stages matterDavid broke down how sales and marketing roles shift as companies evolve. Founders need to let go (eventually), and marketers need to recognize when one-off sales tools are necessary — and when they’re slowing scale.Let sales sellDon’t make them CRM power users. Don’t overload them with fluff. Give them tools that help them — not just your dashboards. And when in doubt, talk to them.🎧 Whether you’re in sales, marketing, or somewhere in between, this episode is for you if:You’ve ever wondered why your content isn’t being usedYou’re trying to support reps in a virtual-first, AI-enhanced worldOr you just like thoughtful, strategic banter (with hats)💬 Let me know what you took away from this episode. And if you're curious to dive deeper into AI readiness for marketing content, you can connect with David on LinkedIn — he’s the only David Kirkdorffer out there. Seriously.Until next time —Keep it human, keep it helpful, and keep selling.– Lee

In this episode, I had a great conversation with Tim Bradley, founder of Pennant—a video marketing firm that’s laser-focused on helping companies improve conversion rates in the middle of the funnel. Tim’s all about storytelling, yes—but with a clear eye on how that story supports sales performance.We talked a lot about the line between marketing and sales enablement, and how the best content—especially video—can serve both when it’s done right.Video as a Sales Tool: Tim broke down his “video marketing trifecta”: Anthem (why you exist), Explainer (what you do), and Endorsement (proof you work). These aren’t just for brand awareness—they’re tools for sales teams to build trust and clarity with buyers throughout the journey.Marketing vs. Enablement: We got into the distinction—and overlap—between traditional marketing assets and true sales enablement content. Great video doesn’t just influence customers; it reinforces key messages for reps too. When reps know the story and understand the pain points it addresses, they sell more confidently.Improving Conversion, Not Just Filling the Funnel: As I said in the episode, you can throw money at lead gen and still fall short. Or you can get smart about where the funnel leaks—and use content to improve handoffs, clarify value props, and speed decision-making. Tim’s all about enabling that kind of lift.Personalized Video for Reps? Yes! Tim strongly encourages sales reps to use video in their outreach. It doesn’t have to be polished—it has to be relevant and human. A personalized message delivered with care can cut through the noise and create meaningful engagement.Storytelling = Risk Reduction: When buyers feel understood, they feel safer. We talked about how storytelling helps reduce perceived risk, which is often what actually drives buying decisions—not feature checklists.One of my favorite parts of this episode was hearing Tim share a recent client success story—a Fortune 30 sales kickoff video that drove real excitement and alignment across the sales team. The video helped a new marketing leader make a killer first impression and gave the sales team tools they were genuinely excited to use.If you’re in sales or sales enablement, this conversation will give you real-world insight into how content and story can drive performance. Video is a powerful lever, not just for reaching buyers but for equipping your team to sell more effectively.🎧 You can find Tim at pennant.video or connect with him on LinkedIn.As always, let me know how you're bringing these ideas to life in your work!Until next time—Lee

In this episode of Thoughts on Selling, I sit down with sales coach and former VP of Sales, Shane Jamison, to talk about the real work behind sustainable sales—coaching to the numbers, managing pipeline pressure without compromising relationships, and becoming the guide your customer needs.We dive into what it means to stay authentic when management wants pull-ins, how to balance urgency with trust, and why pressuring a customer to act early can create more harm than good.Shane shares lessons from his time building and leading teams, and how his passion for coaching emerged from a love of helping people do more than just hit quota—helping them discover where they thrive.👉 Key Takeaways:Align deal timing to customer priorities, not fiscal quarter deadlines.Pressure testing a deal timeline isn’t pushy—it’s collaborative.Discounts rarely drive true urgency in B2B—clarity does.Coaching is about surfacing what reps already know and helping them apply it with confidence.Sometimes the best coaching outcome isn’t closing a deal—it’s helping someone realize they’re in the wrong role.✅ Action Items:Revisit your pipeline: Are close dates based on your internal quarter or the customer's implementation needs?When coaching reps, shift the conversation from "what can you close?" to "where can we create value now?"For managers and sellers alike: take 30 minutes to map the actual steps it takes from verbal commit to closed-won—then build backward.If you're coaching or mentoring, ask: "What kind of sale—and sales environment—helps you do your best work?"Thank you for listening to this episode. I look forward to hearing how you incorporate these strategies into your sales approach.— Lee

In this episode of the Thoughts on Selling podcast, I welcome Steven Ethridge, an accomplished sales trainer, coach, and expert in Neuro-Linguistic Programming (NLP). Our conversation dives into the pivotal roles that mindset and intentional communication play in driving meaningful sales outcomes.Steven shares his structured two-part methodology: Sales Mindset Self-Mastery and his NLP-based Five-Step Sales Process. He highlights how a salesperson's internal belief system shapes external performance and how aligning communication with a buyer's motivations fosters authentic connections and improved results.Key discussion points:Mindset as a foundation. Steven explains how reshaping internal narratives and removing limiting beliefs can dramatically enhance sales performance.Building rapport effectively. We discuss the importance of observing and mirroring both verbal and non-verbal cues to establish deep, authentic rapport.Tailoring communication. Steven emphasizes the need to adapt language to a prospect’s preferred style—whether visual, auditory, or kinesthetic—for greater influence.✅ Key takeaways:A strong, intentional mindset is crucial for long-term sales success.Sales is most effective when it is a collaborative, value-driven process.Attuning your communication style to match that of your prospect can deepen trust and engagement.To explore Steven’s sales training programs, visit ethridge.com.Thank you for listening to this episode. I look forward to hearing how you incorporate these strategies into your sales approach.— Lee

Welcome back to Thoughts on Selling. This one’s a little different — and a little deeper. I had the chance to sit down with fellow ultrarunner, entrepreneur, and coach Troy Meadows to talk about something foundational: your why — personally, professionally, and organizationally.Just like an ultramarathon, building something meaningful in sales (or life) demands more than tactics. You need a reason to keep going when it gets hard. And believe me, it will get hard.🏃‍♂️ Key TakeawaysYour “why” is your North Star: Whether you're selling software or running 100 miles, the why behind your effort determines how you show up when it gets tough.Good sales isn’t about features — it’s about values: If your customer’s why and your company’s values align, magic happens. Think 20-year partnerships, not transactional closes.Hire for values, not just skills: High performers who aren’t aligned to the mission will quietly (or loudly) tank your culture and your customer experience.Sales enablement starts with clarity: A solid mission, vision, and values set the foundation for every positioning doc, every sales pitch, and every customer interaction.Add value like it’s a practice: Whether you’re coaching athletes or consulting startups, assume others don’t know what you know — and serve from that place.🥾 Favorite MomentsThe "family provider" and "community role model" stories that show how powerful a personal why can be.Troy’s perspective on vesting sales commissions over time to drive customer-centric behavior.A classic Merck example that shows what institutional alignment really looks like — and how sales reps need to meet their customer’s mission head-on.Why hiring “no jerks” should be a non-negotiable core value.🧭 RecommendationsLeaders: Post your values where your team and your customers can see them — literally. Make them part of the conversation.Sellers: Stop pitching and start listening for your customer’s why. Align there, and the deal follows.Marketers: Build messaging from the inside out — starting with mission, vision, and values, not product specs.Everyone: Revisit your personal why often. It evolves. Make sure your work still serves it.🏔️ Big thanks to Troy for helping me stretch this episode beyond the usual sales playbook. If you're into running, business building, or just figuring out what makes you tick, check out the Mid Packer Pod and connect with him on LinkedIn.As always, I’d love to hear what resonated for you — and what action you’re taking next.