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

• "The best sales enablement, you don't know what's being done to you. You don't know what's being done for you." — Lee Levitt

  
  

  Closing Thought:As Sean pointed out, the ultimate goal of a leader is to become "invisible"—building a team so competent and well-coached that they no longer need you to intervene. Are you managing by "inspection," looking for mistakes in a spreadsheet, or are you coaching for longevity?. This episode challenges us to stop hovering and start empowering

• Next Steps:If you are ready to build a revenue engine that scales (and maybe finally make yourself obsolete), go say hello to Sean.

  • Visit: GTMPPL.com

  • Connect: Find Sean Gannon on LinkedIn for his latest observations on the industry.

  • Listen & Subscribe: Don’t miss an episode of Thoughts on Selling. Hit subscribe wherever you get your podcasts!

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!