For this episode of Thoughts on Selling, I sit down with my good friend and fellow sales enablement veteran, Tom Kiernan. Tom is a runner, a dad, and a practitioner who cut his teeth at powerhouses like American Power Conversion (APC) and Schneider Electric.

We dive deep into the real difference between "training" (the forbidden T-word) and true enablement. Tom explains why the "Reticular Activating System" is the secret weapon for cutting through the noise in a prospect's brain, and we debate why sales organizations are so bad at the one thing that makes professional athletes great: Practice.

We also touch on a topic close to Tom’s heart—his unique "Books as a Service" non-profit, Lumpy Bones, which helps kids (and adults) deal with difficult topics like cancer through humor and adventure.

Key Findings & Takeaways:

• The "T-Word" vs. Process: Tom argues that training is just an event, while enablement is a process. He shares lessons from the "Toyota Way" and how rigorous process management at APC set the stage for global success.

• The Reticular Activating System (RAS): Ever hear your name over a loudspeaker in a crowded airport? That’s your RAS. Tom explains how "Other Centered Selling" triggers this same mechanism in buyers, stopping them in their tracks because you are talking about them, not your product.

• The Purpose of Selling is Buying: We discuss why the goal isn't to sell, but to help the customer buy. When you shift your motive, you shift your results.

• The Practice Deficit: Professionals practice; amateurs just play the game. We look at the stark contrast between how NFL teams or Broadway casts prepare versus how little practice happens in corporate sales.

• Motive is Transparent: As Tom says, if you are only in it for the commission, it’s written on a "yellow sticky note on your forehead." Customers can smell commission breath a mile away.

• Lumpy Bones: Tom shares his passion project, Lumpy Bones—a "Books as a Service" 501(c)(3) that gets inspiring children's books into classrooms for free through corporate sponsorship.

Memorable Quotes:

• "Motive is transparent. It's written right up on that yellow sticky that [is] slapped up onto your forehead." — Tom Kiernan

• "The best swing is the one that I didn't think about... I practiced to get there, but I just hit the ball." — Tom Kiernan

• "If you don't have a defined process, there's nothing to practice." — Lee Levitt

The Bottom Line:Sales enablement isn't just about teaching reps about new products; it's about building capabilities. Whether it's triggering a buyer's attention or building a coaching culture that actually coaches, success comes down to being "other centered."

Call to Action:

• Check out Tom's Book Series: Visit LumpyBones.com to see how Tom is bringing humor and life lessons to kids.

• Connect with Tom: Find Tom Kiernan on LinkedIn.

• Subscribe: If you enjoyed this conversation, hit subscribe on Thoughts on Selling so you never miss an episode!

In this episode of Thoughts on Selling, I sit down with Ben Perreau, a recovering music journalist turned entrepreneur and leadership expert. Ben joins me from Los Angeles to discuss a problem that plagues almost every growing company: the "Accidental Manager."

We explore Ben’s fascinating journey from the BBC newsroom to consulting for Fortune 50 C-suite executives, and why the transition from superstar Individual Contributor to Team Leader is the most dangerous leap in a career. We geek out on photography as a metaphor for leadership, discuss why we are all just "emotional meat sacks" trying to be professional, and dive into how his new company, Parafoil, is using AI-driven "listening circles" to help new managers survive their first year.

Key Findings & Takeaways:

• The "Man in the Arena": Ben shares how Theodore Roosevelt’s famous speech defined his transition from observing the world as a journalist to shaping it as an entrepreneur.

• The Accidental Manager Crisis: A staggering 82% of early-career managers consider themselves "accidental"—thrust into leadership because they were good at their technical job, not because they were trained to lead.

• Leadership vs. Photography: We discuss the difference between staying in "Auto Mode" versus mastering "Manual Mode." Great leaders, like great photographers, need to know the technicals but ultimately succeed through composition and vision.

• The "Emotional Meat Sack" Reality: We try to breed emotion out of work, but we are emotional creatures. Ben argues that suppressing this leads to burnout and failure; effective leadership requires integrating your emotional self with your professional self.

• Listening Circles: Ben highlights his new platform, Parafoil, which uses "Listening Circles" to create safe, high-trust environments where managers can practice feedback and difficult conversations without fear of judgment.

Memorable Quotes:

• "I think Ben Perreau... is a complex mix of dualities in search of trying to find the one version of myself in amongst all of that." — Ben Perreau

• "Never doubt that a small committed group of people can change the world. In fact, it's all it ever has." — Ben Perreau (quoting Margaret Mead)

• "There's a reason why 82% of early career managers consider themselves accidental managers. And there's a reason why a third of their teams leave within a year." — Ben Perreau

• "We've almost constructed... our own landscape to help us find our own way out of the sort of emotional meat sacks that we all are... but actually it's the counter narratives." — Ben Perreau

The Bottom Line:

We often promote our best salespeople, engineers, or marketers into management and then abandon them. Ben’s work with Parafoil reminds us that leadership is a craft that must be practiced, not just a title that is bestowed. If you want to stop the churn of "accidental managers," you have to provide a safe space for them to fail, learn, and grow.

Call to Action:

• Stop the Churn: Are you an "accidental manager" or leading a team of them? Check out how Parafoil is changing the game.

• Connect with Ben: Visit Parafoil.co or find Ben Perreau on LinkedIn.

• Subscribe: Enjoyed this deep dive on leadership? Hit subscribe on Thoughts on Selling so you never miss a conversation.

In this episode of Thoughts on Selling, I sit down with Amos Bar-Jospeh, a third-time entrepreneur connecting from Tel Aviv. Amos describes himself as an "anti-capitalist capitalist" -- someone who has rejected the old "growth at all costs" unicorn playbook in favor of a new model: the Autonomous Business.

We dive deep into why the "raise a shit ton of money and hire 40 people before revenue" model is broken. Instead, Amos is building Swann, a company designed to scale with intelligence rather than headcount. We explore the concept of Human-AI collaboration (not replacement), why sales is a zero-sum game of attention and budget , and why the future of software isn't about "record and report," but about adaptive systems that wear the shape of your workflow.

Key Findings & Takeaways:

• The "Unicorn Playbook" is Dead: The era of raising massive capital before finding product-market-fit is over. Amos advocates for scaling companies by discovering the "100x version" of each employee through AI augmentation rather than just adding bodies.

• Sales is a Zero-Sum Game: Attention and budget are finite. If everyone uses the same AI SDRs to spam the same buyers, no one wins. Success comes from being different, not just better, which requires human creativity.

• Zone of Genius: The goal of AI isn't to replace the human but to automate everything outside their "zone of genius" so they can focus on high-value interactions.

• The New Software Paradigm: We are moving from static software (like traditional CRMs) to adaptive software that learns your specific habits and feedback loops. It’s not about "more features" -- it’s about software that re-tailors itself to you every single day.

• System Interactions to Zero: For 20 years, CRMs promised to help us sell but became reporting burdens. The future is reducing system interactions to zero so sellers can spend 100% of their time on buyer interactions.

Memorable Quotes:

• "I’m an anti-capitalist capitalist... I’ve realized... that playbook [growth at all costs] is not for me." — Amos Bar-Jospeh

• "It's a business that is designed to scale with intelligence, not with headcount." — Amos Bar-Jospeh

• "The future belongs to organizations that... turn each person on the team into their 100X version of themselves." — Amos Bar-Jospeh

• "We need to understand... not the AI replacing the AE, it's the AI taking the review process of that AE specifically, formalizing it and repeating it." — Amos Bar-Jospeh

The Bottom Line:We are entering an era where "software" as we know it -- static tools we have to feed data into -- is becoming obsolete. The new winners will be organizations that master Human-AI Collaboration, creating feedback loops that allow AI to handle the mundane while humans drive the strategy.

Call to Action:

• Audit Your Stack: Are your tools "recording and reporting" or are they actually adapting to your workflow? It might be time to demand more from your software.

• Join the Movement: Subscribe to Amos’s newsletter, The Big Shift, to follow the journey of building an autonomous business.

• Experiment: Try out Amos’s digital clone, "Autonomous," in the ChatGPT store to ask your own questions.

• Connect: Find Amos Bar-Jospeh on LinkedIn (he has over 30k followers for a reason!)

For this episode of Thoughts on Selling, Garth Fasano joins me to discuss the massive shift happening in inside sales.

Garth Fasano is an ETA (Entrepreneurship Through Acquisition) entrepreneur and leader of a high-growth startup focused on autonomous sales.

From sailing mishaps in Long Island Sound to the complexities of call center Erlang models, We discuss the evolution of the "inside sales" role and explore how "Agentic AI" is moving beyond simple decision trees to becoming the top-performing sales agent—one that is fully caffeinated and ready to sell 24/7.

Key Findings & Takeaways:

• The "Best Day" Every Day: The biggest advantage of Agentic AI isn't just automation; it's consistency. Customers want the best agent on their best day, not an agent who is 175 calls deep at 5:00 PM.

• Small Business is Leading the Charge: Unlike enterprises bogged down by legacy CRM integrations, small businesses are adopting autonomous sales faster. They need to capture leads instantly (e.g., a 3 AM water damage call) without the owner having to answer the phone while working a job.

• Visibility as a Service: Autonomous agents don't just sell; they provide "visibility as a service." Instead of a business owner guessing why sales are down, the AI can proactively report, "Conversion is down 10% because of price objections."

• The End of "Typing While Talking": Traditional inside sales requires reps to juggle rapport building while furiously typing data into a CRM. Agentic AI removes this friction, capturing data instantly and allowing for better customer interaction.

• Bot-to-Bot Commerce: The future is already here. We are seeing "agentic to agentic" conversations, such as Google's AI calling businesses to check pricing and availability on behalf of consumers.

Memorable Quotes:

• "They want them at their 9am fully caffeinated self ready to rock and roll, not their 5pm, 175 calls deep... self." — Garth Fasano

• "A sales call that's scripted... That's not how sales work. That's not how people buy." — Garth Fasano

• "Google knows how you search... Open AI knows what you're using this information for... we're going to start to know why customers are buying." — Garth Fasano

Connect with Garth:

• LinkedIn: Garth Fasano

• X (Twitter): @GarthFasano

What do selling gum in the 5th grade and playing defense in hockey have in common with enterprise sales? According to Nina Iannuzzi, everything.

In this episode, I sit down with Nina, a sophomore at the Isenberg School of Management (UMass Amherst) and a top-5 finalist at the recent National Intercollegiate Sales Competition (NISC). We relive the chaos of "speed selling" in a gym filled with 1,000 suits, discuss how to handle a curveball question from a CFO, and laugh about the moment I rudely interrupted her final sales pitch with a fake phone call.

Nina brings an infectious energy that proves the future of sales is in very good hands. Whether you are a student, a sales leader, or just someone who appreciates the hustle, you will love her take on why "sucking it up" is the only way to win.

Key Highlights & Takeaways:

• The Slime Economy: Nina’s sales career didn’t start at UMass; it started in 5th grade selling slime and gum to classmates.

• Defense Wins Championships: As a hockey player for 16 years (Left D!), Nina treats walking into a sales room like a puck drop: you know your job, now go execute.

• The "Scope" Stumble: Nina shares a vulnerable moment where a buyer kept asking about "scope," a term she wasn't fully sure how to handle in the moment. Her retrospective advice? Don't fake it—ask a clarifying question immediately.

• The Plot Twist: I threw a wrench in her final round by bursting in with a "phone call." Nina stayed so locked in she almost kicked me out of the room before realizing the "emergency" was just a timer on my iPhone!

• The Contract Slide: Nina admits her main goal wasn't just to chat—she literally slid a physical contract across the table at the 4-minute mark. Always be closing!

• Suck It Up, Buttercup: Her coach’s advice for sports and sales: if a lace breaks or a deal stalls, you don't call an Uber. You fix it and keep running.

Memorable Quotes:

• "I’m a very big talker. I’m competitive... I started my first business in like fifth grade, just selling like slime and gum." — Nina Iannuzzi

• "You get in that room and... you sit down and you're like, I am SpotLogic... I almost wanted to act like we were friends." — Nina Iannuzzi

• "Suck it up buttercup or move on to bigger and better things." — Nina Iannuzzi

Closing Thought:If you think the next generation of sales talent is "soft," you haven’t met Nina. Her "suck it up, buttercup" attitude is a wake-up call for seasoned professionals who might have gotten a little too comfortable. Nina proved that you don't need 20 years of experience to have sales instincts—you just need the courage to slide the contract across the table.

Next Steps:

• Challenge Yourself: Take a page out of Nina's playbook this week. Be bold, ask the clarifying question, and don't let a "fake phone call" derail your pitch.

• Get Involved: Want to see this talent in action? Look into judging or sponsoring a collegiate competition like NISC.

• Connect: Follow Nina Iannuzzi on LinkedIn to follow her journey from UMass to the C-Suite.

I sit down with Sean Gannon, founder of GTMPPL (GTM People), to answer the "unanswerable" question: Who is Sean Gannon?. We dive into a refreshing take on sales leadership—why the best managers strive to make themselves obsolete—and explore the often friction-filled relationship between sales and marketing.

From the trenches of EdTech to the nuances of Sandler training, Sean shares candid stories about the transition from "spreadsheet inspection" to true coaching. We also discuss why "everyone sells" (even if they don't have a quota) and share a hilarious cautionary tale about what happens when a salesperson sticks to the script even after the customer has said "yes."

Key Highlights & Takeaways:

• The "Obsolete" Manager: Sean argues that a manager’s ultimate goal is to make themselves invisible and obsolete; if the team can't function without you, you aren't doing your job.

• Everyone is in Sales: Whether you are an SDR, a CSM, or pitching a project to your boss, everyone in the organization is selling something.

• Marketing vs. Sales: We dismantle the old school "throw it over the wall" mentality regarding leads. Sean emphasizes that while marketing provides air cover, they must care about close rates, not just lead volume.

• Coaching vs. Inspection: Sean opens up about his evolution from a manager who managed by spreadsheet to a leader who focused on coaching, which drastically improved his team's retention from 18 to 36 months.

• The Danger of the Script: A great lesson on reading the room—Sean shares a story where a salesperson kept taking him through the Sandler "pain funnel" even though Sean was already sold and ready to buy.

• Authenticity Wins: Why "I don't know" is a perfectly acceptable answer that builds more rapport than faking it.

  
  

Memorable Quotes:

• "I view my role as an executive or a sales manager... to make myself obsolete. Like, I should be relatively invisible as your manager." — Sean Gannon

• "Your job is to sell the meeting... not to sell the company, isn't to sell the solution." — Sean Gannon

In this episode, I geek out with Maeve Ferguson, an ex-steeplechase jockey turned Big Four consultant and data expert. We dive deep into the often-overlooked power of diagnostic assessments and how "Agentic AI" is revolutionizing the way experts build sales funnels.

Maeve shares how moving beyond simple "quiz funnels" to robust data diagnostics can uncover the gap between an entrepreneur's perception and their business reality, ultimately leading to higher-quality leads and closed deals.

Key Highlights & Takeaways:

• The Power of Diagnostics: Maeve explains why diagnostic assessments are superior to standard lead magnets. They provide proprietary data that allows you to segment audiences by investment ability (Platinum to Bronze) and customize the sales journey based on their specific struggles.

• Unicorn Leadership Types: We discuss the "Ulta" framework—Visionizer, Strategizer, and Mobilizer. Understanding these profiles is critical not just for leadership, but for ensuring your sales and marketing teams aren't operating at cross-purposes.

• Agentic AI in Sales: Maeve reveals how she uses AI agents to run continuously in the background. These agents analyze who buys high-ticket items versus low-ticket items and automatically optimize ad copy to attract better buyers.

• The "Delulu" Factor: Data hates nature and never lies. Maeve shares amusing insights on how diagnostics expose the gap between where business owners feel they are versus what the numbers actually say—a critical leverage point for sales conversations.

• Sales Coaching Automation: We explore how AI agents now review sales call transcripts against frameworks to provide immediate, in-context coaching to sales reps, celebrating wins and flagging missed opportunities.

• Passion, Authenticity, and Curiosity: I challenge Maeve on her self-assessment as a salesperson, applying my three-part diagnostic for sales effectiveness.

Resources Mentioned:

• Maeve’s Diagnostic: Impact Score Assessment

• Book Mentioned: Surrounded by Idiots by Thomas Erikson

Connect with Maeve Ferguson:

• LinkedIn: Maeve Ferguson

• Substack: Maeve Ferguson

This is one of the most high-energy, high-insight conversations we've had on the show!
If you care about data, diagnostics, sales, or the future of AI-powered selling, you’re going to love this one.

In this episode of Thoughts on Selling, I sit down with someone I truly consider a “brother from another mother” — Lester Sidney.

If there’s a theme for this conversation, it’s this:

👉 Sales is human work. And humans run on purpose, energy, trust, and honesty.

Lester discusses his 17-year tech sales career, a couple ofunexpected detours, and the journey that ultimately led him to rediscover his why: helping people see the potential insidethemselves that they can’t yet see.

What unfolds from there is one of the most honest, raw, and deeply human sales conversations we've recorded.

We talk about:

·      Finding purpose when life knocks you flat, including Lester’s battle with depression after leaving a company he helped build.

·   The Ikigai framework and how it helped him identify a deeper purpose rooted in mentoring and coaching.

·      Energy as a magnet — how the energy we project determines the people and opportunities we attract.

·       Why giving beats taking, and how “pay it forward” moments shape who we become.

·       The sacred role of trust in sales, and why walking away from a deal can be the single biggest credibility builder you’ll ever have.

·       Extreme Ownership — and why real leaders take responsibility for everything their team does. (Yes, this comes with stories.)

·       Why vulnerability isn’t weakness — it’s a sales superpower. Lester is candid about how being open unlocks deeper relationships with customers.

·       The compound effect, and why small improvements add up to big transformation — in fitness, in selling, and in life.

·       Raising kids with mindset, from eliminating the word can’tto teaching his son that mistakes are how we grow.

·       What Lester looks for when hiring sellers — and why coachable is the non-negotiable #1 trait.

This is an episode about selling, yes — but more importantly, it’sabout being human. It’s about showing up with authenticity, owning your story, doing the hard things, and leading with heart.

It’s one of my favorite episodes we’ve done. Give it a listen —and please tell me what resonates most with you!

In this episode of the Thoughts on Selling podcast, Torquil Thomson, joining me from Barcelona, explore something most revenue leaders know but rarely address head-on: your go-to-market engine is only as good as the data, systems, and human judgment beneath it.

Torquil brings 20+ years of experience across SaaS, sales ops, and country leadership, and today helps companies fix the messy operational foundations that stall growth — especially in the age of AI.

We start with his background, his move from Scotland to Spain, and how he kept gravitating toward building systems that help people perform, no matter the role he was in. From there, we dig into what The Conversion Architects do — and why so many companies think they have a “pipeline problem” when they really have a data quality and process problem.

Torquil shares astonishing numbers:

• Many companies have 40–50% duplicate records.

• Another 5–10% of contacts have no name.

• In one case, a customer had 2 million accounts… and only 1 million contacts.

As Torquil puts it, “You can’t build AI on chaos.”
AI isn’t magic — it’s a learning model. If your CRM is full of mud, your revenue engine runs on mud.

🔍 The Hard Truth About CRM Data

Torquil shares astonishing numbers:

• Many companies have 40–50% duplicate records.

• Another 5–10% of contacts have no name.

• In one case, a customer had 2 million accounts… and only 1 million contacts.

As Torquil puts it, “You can’t build AI on chaos.”

AI isn’t magic — it’s a learning model. If your CRM is full of mud, your revenue engine runs on mud.

🤖 AI, GTM Systems & the Illusion of the “Magic Wand”

We break down why so many organizations bolt AI tools onto broken systems and expect miracles. Torquil explains how:

• AI fails when the underlying data is incoherent.

• SDR/BDR tech stacks have become increasingly fragmented.

• Go-to-market engineers often build “Frankenstein systems” companies can’t maintain.

The Conversion Architects focuses on cleaning, deduping, enriching, and restructuring CRM data using a bow-tie model — because revenue systems must work underneath the automation, not just on top of it.

🔄 Humans > Machines (at Least for Now)

One theme that comes up again and again:

Sales is — and will remain — human.Automation should eliminate admin work, not connection, nuance, or judgment.

Torquil talks about using AI to help reps:

• Manage more opportunities without burning out

• Keep customer handoffs clean

• Identify when key roles change within an account

• Flag renewal risks before it’s too late

But not to replace the human element that actually moves deals.

🎯 Where Companies Gain the Most Leverage

Torquil sees opportunity across the full bowtie, especially here:

• Fixing handoffs between Sales → CS

• Aligning systems that don’t speak to each other

• Renewals and expansions (where companies often lose track of decision-makers)

• Automating the long-tail of high-propensity customers that reps never have time for

He shares a success story involving product-triggered outreach that drove huge lift — from understanding behavior, rather than blasting cold lists.

🧠 The Human Insights Sales Leaders Keep Missing

We talk about:

• Why sales engineers and first-line managers remain the highest-leverage roles

• Why reps struggle to talk about change management

• How AI allows buyers to become dramatically more informed

• Why customers don’t want more information — they want confidence

This leads to a discussion of The JOLT Effect (Matt Dixon & Ted McKenna), and how true sales impact comes from helping customers feel safer moving forward, not drowning them in detail.

⭐ Key Takeaways

• You can’t automate your way out of bad data.

• AI amplifies whatever foundation you have — good or bad.

• Sales is still human, especially when change and risk are involved.

• Fixing the middle of the bowtie (handoffs, renewals, role changes) unlocks huge value.

• Sales engineers and CS handoffs remain massively underutilized assets.

• Confidence beats information — especially in complex sales.

In this episode of Thoughts on Selling, I sit down with my friend and long-time sales industry pioneer Gerhard Gschwandtner — founder of Selling Power Magazine and an enduring voice in the world of sales leadership, mindset, and authenticity.

Gerhard’s story is extraordinary — from growing up in Austria and stumbling into his first sales role (inventing sales enablement decades before it had a name) to creating Selling Power Magazine, one of the most influential platforms in the history of professional selling.

We talk about how curiosity, creativity, and courage shape every career — and how staying in the question, not rushing to the answer, is what keeps you growing. Gerhard shares how he’s helped shape the profession through interviews with legends like Mary Kay, Zig Ziglar, Wayne Dyer, Mark Benioff, and even a few time-travel guests like “Abraham Lincoln” and “Aristotle.”

This isn’t just a history of sales — it’s a masterclass in mindset.

💡 Key Takeaways

• “Who are you?” is the most important sales question. You can’t sell authentically until you know yourself.

• Mindset is everything. Gerhard outlines three lenses — implanted, imprinted, and inspired mindsets — that shape how we think and sell.

• Sales enablement started long before software. His early innovations — customer tours, training vignettes, and user groups — became today’s best practices.

• Authenticity builds trust faster than persuasion. Telling the truth, even when it’s uncomfortable, turns customers into lifelong advocates.

• AI is both a gift and a trap. Used wisely, it elevates preparation. Used poorly, it replaces thinking.

• The bigger the why, the bigger the try — and the easier the how.

This conversation spans history, psychology, and purpose — from Aristotle to AI — reminding us that great salespeople are first and foremost great humans.

🎧 Listen in and rediscover the timeless truth of selling: authenticity wins.

#ThoughtsOnSelling #SalesMindset #Authenticity #SellingPower #SalesEnablement #InnerGame

In this episode of Thoughts on Selling, I sit down with Lauren Bailey, one of the most dynamic voices in modern sales leadership. She’s the founder of Factor 8 (award-winning inside sales training), #GirlsClub (empowering women in revenue roles), and Legacy VIP (a community for seasoned executives who crave purpose and authentic connection).

What starts as a conversation about leadership quickly turns into something deeper — a raw, funny, and inspiring dialogue about who we are and why we do what we do.

Lauren shares how losing her best friend became the catalyst for creating Legacy, a space where executives show up as their whole selves — not just their résumés. She also talks about integrity, self-awareness, and the power of human connection — lessons drawn from personal experience, Landmark Forum, and years of leading sales teams worldwide.

• Show up and say yes. These two rules, says Lauren, change everything — in leadership, friendship, and sales.

• Be impeccable with your word. (A nod to The Four Agreements.) If you say it, do it — and say less if you can’t commit.

• Authenticity over perfection. Perfectionism kills confidence; authenticity builds it.

• Celebrate the 3 F’s — fears, failures, and f-ups. Vulnerability builds confidence faster than success ever could.

• Coachability matters. The best sellers aren’t perfect — they’re curious, confident, and willing to be coached.

• The pause game. Lauren’s favorite technique: pause a recorded sales call every 10 seconds and ask, “What’s the customer thinking?” and “What would you do next?” It builds awareness, empathy, and skill faster than any script.

• Leadership is a “we” sport. The skills that make us great sellers don’t always make us great managers. True leadership is about creating space — not taking it.

We talk about Landmark Forum, Don Miguel Ruiz’s The Four Agreements, and the difference between selling and buying. It’s a conversation full of laughter, truth bombs, and practical takeaways for anyone leading, coaching, or selling today.

Lauren’s energy is contagious — she’ll make you laugh, nod, and probably take notes.

🎧 Listen in and rediscover the joy in what we do — showing up, saying yes, and being fully human while we sell, lead, and live.

#ThoughtsOnSelling #SalesLeadership #AuthenticSelling #InnerGame #WomenInSales #SalesEnablement #LegacyVIP

🧭 Key Themes & Lessons

In this episode of Thoughts on Selling, I sit down with Kevin Hubschmann, a former enterprise software rep turned comedian and founder of Laugh.Events — a company literally delivering “Laughter as a Service.”

We dig into the parallels between improv, comedy, and enterprise sales, exploring how humor, presence, and curiosity can transform the way we connect with customers. Kevin shares his story of balancing daytime sales calls with nighttime comedy clubs, and how the two worlds collided to shape his philosophy on sales as performance and connection.

Key themes:

• Listening > Talking. Kevin breaks down why most sales calls fail because reps talk too much — and how mastering silence is the first step to earning trust

• F your good idea. (Yes, really.) In improv and in sales, the goal isn’t to deliver your rehearsed pitch — it’s to respond to what’s actually happening in the moment

• Yes, And… We explore how collaboration — not control — drives great sales conversations

• Callbacks in sales. Borrowed from stand-up comedy, callbacks create instant connection by recalling earlier details — proving you were listening and care

• Deliberate practice builds instinct. Sales mastery, like comedy, comes from reps — not scripts

• Laughter builds trust. Humor isn’t about cracking jokes. It’s a sign of shared understanding — the customer’s way of saying, “I get you”

We also talk about how curiosity creates genuine human connections — the kind that earn referrals and deepen relationships. From field sales to front-stage comedy, Kevin shows how the same skills that make people laugh also make people buy.

🎧 Tune in and learn how the best salespeople stay in the moment and create powerful connections

#ThoughtsOnSelling #SalesEnablement #Storytelling #AuthenticSelling #ImprovInSales #LaughterAsAService

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:

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 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 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