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What does it really take to build trust in your team and with your buyers?

In this episode, we’re joined by Jake Mannino, Global Sales Director at Microsoft and certified executive coach, for a deep dive into the emotional and strategic foundations of trust in sales.

Jake shares lessons from 25+ years leading high-performing sales teams and coaching some of the world’s top professionals. He reveals why trust begins with self-awareness, and how authenticity, logic, and empathy form the core triangle of lasting relationships.

You’ll hear how simple language shifts like removing “can’t” can change entire mindsets, and why the best leaders focus on rapport, adaptability, and involvement.

This conversation also explores:

• How to turn red-path thinking into green-path belief
• The Shackleton survival story as a metaphor for modern leadership
• How to decode customer behavior through pattern recognition
• Why knowing your customer’s culture matters more than their 10-K

Whether you’re a frontline seller or a seasoned executive, this episode offers transformative insights into what it really means to earn the right to be trusted.

Don't miss out—your next big idea could be just one episode away!

This Show is sponsored by Fist Bump
Your prospecting partner to authentically fill your pipeline with ideal customers.

Check out our Live Show Events here: Mastering Modern Selling Live Show

Subscribe to our Newsletter: Mastering Modern Selling Newsletter

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In Episode 140 of Mastering Modern Selling, we welcome back Bill McCormick, founder of DigiSales, for a powerful conversation on breaking out of the social selling echo chamber.

Bill shares how his mindset evolved from “LinkedIn is everything” to a more thoughtful, multi-channel strategy that meets buyers where they are.

You’ll hear why content alone won’t drive pipeline, how to create real LinkedIn conversations, and what it means to be truly buyer-centric in your sales approach.

This episode is packed with practical takeaways, honest reflections, and a refreshing reminder that modern selling isn’t about choosing sides, it’s about making better choices.

Topics Covered:

• Why all selling is social, but not just on social
• The myth of the “perfect posting schedule”
• How to use your LinkedIn profile as a value magnet
• What bad sales culture teaches (and how to fix it)
• Why leadership must show up for digital change

If you’re ready to trade empty activity for meaningful progress, don’t miss this one.

Don't miss out—your next big idea could be just one episode away!

This Show is sponsored by Fist Bump
Your prospecting partner to authentically fill your pipeline with ideal customers.

Check out our Live Show Events here: Mastering Modern Selling Live Show

Subscribe to our Newsletter: Mastering Modern Selling Newsletter

Leave your comment

In this episode, Tom Burton and Carson Heady explore how artificial intelligence is transforming sales in real, practical ways. While AI offers powerful tools to plan smarter, personalize outreach, and even recover stalled deals, the human element remains central to success.

With insights drawn from their experience working with sales teams at Microsoft, Tom and Carson break down each phase of the sales cycle planning, prospecting, forecasting, and customer engagement and show how AI can augment, not replace, authentic relationship-building.

If you want to stay relevant and effective as the sales landscape evolves, this episode is your playbook.

• What we discussed:

1. Smarter Sales Planning with AI

AI can analyze your pipeline, uncover gaps, and spotlight high-potential accounts.

It helps you plan your year or quarter with data-backed insights rather than guesswork, identifying where to invest your efforts for the biggest returns.

2. Personalized Prospecting and Outreach

By scanning LinkedIn profiles, company info, and recent news, AI crafts tailored messages and subject lines designed to increase open and response rates.

But Tom stresses: AI drafts the message you add the personal tone and relevance that build trust.

3. Data-Driven Forecasting

Forget adding arbitrary percentage increases to last year’s sales. AI can process historical data and industry benchmarks to help build forecasts that are both ambitious and achievable.

This brings more credibility and accuracy to your sales planning.

4. Handling Ghosting and Tough Conversations

When prospects go quiet or hesitate, AI can help draft empathetic, clear follow-ups that acknowledge their concerns and reduce the perceived risk of moving forward.

These messages open doors to honest conversations and keep deals moving.

5. Balancing Automation with Authenticity

Ultimately, the episode highlights a vital truth: AI boosts efficiency, but it can’t replace empathy, insight, or the human connection.

Your unique voice and understanding of your customer’s needs remain the biggest competitive advantage.

AI is no longer a futuristic concept, it’s here and changing how we sell. But success isn’t about replacing the human touch; it’s about combining AI’s power with your authentic relationship-building skills.

Tom and Carson’s advice offers a roadmap for sales pros who want to stay effective, relevant, and indispensable in an AI-driven world.

Don't miss out—your next big idea could be just one episode away!

This Show is sponsored by Fist Bump
Your prospecting partner to authentically fill your pipeline with ideal customers.

Check out our Live Show Events here: Mastering Modern Selling Live Show

Subscribe to our Newsletter: Mastering Modern Selling Newsletter