strategic selling

Two Tall Guys Talking Sales – Workflows, Automation, and AI: Building a Smarter Sales Organization – Episode 145

By Sean O'Shaughnessey

In this compelling episode, co-hosts Kevin Lawson and Sean O’Shaughnessey delve into the crucial distinctions between workflows, automations, and artificial intelligence (AI), and why understanding these differences isn’t just technical trivia, but foundational to improving sales processes, enhancing sales management, and accelerating revenue generation. If you’re a sales leader, business owner, or B2B rep striving to improve how you use technology to boost sales success, this episode is a must-listen. Packed with real-world examples and expert commentary, you’ll walk away with a clearer understanding of how to integrate automation and AI into your selling environment without losing the human touch that drives value selling.

Key Topics Discussed

The Distinction Between Workflow and Automation (approx. 01:00)
Kevin and Sean explain that workflows are rule-based sequences (what should happen), while automations are system-triggered actions (when they happen).
Applying Workflow and Automation to Common Sales Scenarios (approx. 03:00)
Sean walks through onboarding, fulfillment, and follow-up processes that can be automated to save time and reduce human error.
The Role of AI in Enhancing Sales Tasks (approx. 05:00)
Discover how AI moves beyond automation by adding intelligence and insight, like writing customized thank-you messages or enriching CRM data.
What Sales Leaders Should Expect from Modern CRM Systems (approx. 12:00)
Sean lays out a vision of AI-enabled CRMs that proactively suggest key contacts and actions for deeper account penetration.
Creating Sales Infrastructure That Supports Scale (approx. 09:00)
Kevin emphasizes how business logic, automation, and AI build a more agile, informed sales team that’s prepared for disruption.

Key Quotes

Kevin Lawson (approx. 00:46):
“Workflows are trigger-based events that tell business logic what to do next… but automation is what makes things happen automatically, without human intervention.”
Sean O’Shaughnessey (approx. 05:43):
“We used to personalize thank-you letters with a person. Now we can automate that process and use AI to generate something that’s still meaningful but takes no time.”
Kevin Lawson (approx. 10:00):
“AI plus workflows plus automation creates the bedrock for a better sales organization… a more nimble organization that can adapt to changes in the environment.”
Sean O’Shaughnessey (approx. 13:08):
“Does your CRM say, ‘Did you know there are three directors of manufacturing at that company?’ That’s where workflows, automation, and AI converge to fuel revenue growth.”

Additional Resources

Join the B2B Sales Lab Community – A peer-driven space where sales professionals, managers, and leaders exchange insights, share best practices, and build smarter revenue systems.

A Significant Actionable Item from this Podcast

Audit your CRM and lead-handling processes.
Ask yourself: Is my CRM working for me, or am I working for it? Review whether incoming leads are routed automatically, if emails are logged without manual entry, and whether sales leaders receive alerts on stalled opportunities. Implement at least one automation or AI-powered enhancement, such as auto-logging emails or enriching lead data, to eliminate repetitive tasks and enable your team to focus on strategic selling.

Why You Should Listen Now

This episode isn’t just a primer on sales tech buzzwords; it’s a blueprint for operational excellence in B2B sales. Kevin and Sean break down complex topics with clarity and offer practical advice that can immediately improve your sales team’s responsiveness, accountability, and business acumen. If you’re serious about building a scalable sales infrastructure, aligning your team with cutting-edge sales strategies, and using AI as a force multiplier for your messaging and revenue management, then queue up this episode today. You’ll walk away with new ideas, sharper thinking, and a to-do list worth acting on.

Transform Your Sales Strategy with the Three-Legged Stool Approach: Resonate, Differentiate, Substantiate

By Sean O'Shaughnessey

Business-to-business (B2B) sales is more than selling a product or service. It involves a strategic approach that includes understanding the customer’s needs, differentiating your offering, and building trust. This strategic approach is often called the three-legged stool of sales: Resonate, Differentiate, and Substantiate.

Resonating with customers is the first step (leg) in the sales process. It involves answering the questions “Why should the customer act?” and “Why should they act now?” To resonate with customers, you must understand their goals and how your product or service can meet them. This requires careful listening, understanding, and empathy.

The second leg of the stool is differentiation. This answers the question, “Why choose us?” Differentiation is all about highlighting what makes your product or service unique from the competition. This could be anything from superior quality and innovative features to excellent customer service. It’s crucial to communicate this differentiation clearly and effectively to the customer.

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Two Tall Guys Talking Sales Podcast – The Gap Analysis Advantage: Bridging Client Needs with Optimal Solutions with Chris Cocca – E86

By Sean O'Shaughnessey

Welcome to this week’s episode of Two Tall Guys Talking Sales, where hosts Kevin Lawson and Sean O’Shaughnessey are joined by Chris Cocca, a sales expert, to discuss the vital aspects of discovery meetings and qualifying prospects for a robust sales pipeline. Tune in as they delve into the methodologies that distinguish successful sales strategies, particularly focusing on the RAIN training concept and the essential practice of understanding client aspirations and afflictions.

Key Topics Discussed:

RAIN Training and Strategic Selling: Chris Cocca shares insights into how RAIN training complements traditional strategic selling concepts, helping salespeople better understand where their clients currently are and where they aim to be.
Aspirations and Afflictions: The discussion highlights the importance of understanding clients’ aspirations and afflictions to maximize the perceived value of offered solutions.
Gap Analysis in Sales: Kevin underscores the importance of gap analysis in sales processes, emphasizing how salespeople should position themselves as solutions within the business context.
The Role of CRM Systems: Chris stresses the significance of CRM systems in capturing and utilizing quality data for sales success, illustrating how technology underpins effective sales strategies.
Role-Playing for Sales Training: A discussion on the practical application of role-playing exercises as a method to enhance sales personnel’s discovery skills.
The Importance of Proper Discovery: Sean wraps up the discussion by reinforcing the necessity of a well-executed discovery process, which is crucial for improving sales outcomes.

Key Quotes:

Kevin Lawson: “I love that you’re tying the gap analysis because as salespeople, we need to be thinking about that gap because it’s the, where do I fit into this business as a solution?”
Sean O’Shaughnessey: “Practice makes easy for asking discovery questions. Asking those business-related questions. Curious how you do that.”
Chris Cocca: “The further apart that those aspirations and afflictions are, the more value you can show because you’ve got a lot to work with. If that gap is really narrow and you don’t define that really well, guess what happens? It’s all about price.”

Additional Resources:

“Strategic Selling” by Miller Heiman https://a.co/d/6qJH9ME
RAIN Sales Training Platform https://salesxceleration.com/news-events/transform-your-sales-performance-with-rain-group-and-sales-xceleration/

Summary:

This episode is a treasure trove of insights for any sales professional looking to sharpen their discovery skills and improve their sales strategy. From understanding the critical role of CRM systems to mastering the art of asking the right questions during client meetings, our guests cover it all. Whether you’re a seasoned sales leader or a new salesperson, this discussion offers valuable techniques that can be immediately implemented to enhance your sales process and ultimately drive better results. Don’t miss out—listen now and transform your sales approach!

Join us next week for more insightful discussions on Two Tall Guys Talking Sales.