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Are you accidentally talking your prospects out of a good experience before they’ve even had it?

In sales, we often think we are building rapport by being "honest" about the tedious parts of our process. We say things like, "Okay, now comes the boring part—the paperwork," or "I'm sorry, this next step is a bit of a slog". We think we are managing expectations, but in reality, we are engaging in self-sabotage. We are literally selling the client on having a bad experience before it even starts.

In this episode of The Sandler Training Hour, Jim and Jason Stephens break down the concept of "Poisoning the Well". They explore why salespeople feel the need to qualify the experience negatively and how to shift your mindset to sell the commitment to the result rather than apologizing for the path to get there.

Key Topics Covered:

• The Assumption Trap: Just because you hate paperwork doesn't mean your prospect does. Jim shares a personal example regarding his wife, who actually enjoys filling out forms. When you apologize for a step in the process, you are making an assumption about the other person that may be flat-out wrong. Without intending to, you "telegraph" your own negative feelings onto the buyer.
• Selling the ROI, Not the Cost: Jason uses the example of Sandler assessments. These take 15 to 20 minutes to complete. An amateur salesperson warns the prospect that it is time-consuming. A pro sells the ROI on why that investment of time is valuable. If you feel apologetic about imposing requirements, you invalidate your own process.
• The "Amazon" Standard of Friction: We live in a culture that expects frictionless ease. Jim notes that even when we could buy something at the store, we order it on Amazon to get it "off the list". Salespeople must continuously critique their systems to ensure they aren't adding unnecessary friction.
• Mastery vs. The Comfort Zone: Mastery doesn't come from hitting a plateau and coasting; it comes from proactively challenging what you are doing. If you have done a process a thousand times, you might be on "autopilot," unaware that you are projecting boredom or resentment onto the client.
• Stop Mind-Reading: Jim highlights a common error where salespeople interpret a prospect's facial expression as rejection. The probability that their face means what you think it means is almost non-existent. Instead of assuming ("Oh no, they hate the price"), simply ask: "I can't help but notice your reaction—would you mind explaining what that means?".

Challenge of the Week:This week, Jim and Jason challenge you to perform a Language Audit on your sales conversations.

Ask yourself: What part of your process are you selling in a negative light?

• Are you telling prospects that your contract is "long"?
• Are you warning them that onboarding is "tedious"?

Catch yourself using these negative adjectives and stop. Your job is to lead them to the result, not warn them about the path.

About the Show: Join hosts Jim and Jason Stephens from Crossroads Business Development as they discuss techniques, tactics, and the occasional tangent associated with the Sandler Selling System. Whether you are prospecting, negotiating, or closing, The Sandler Training Hour gives you the actionable advice you need to stop "winging it" and start controlling the sale.

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In this episode, Jim and Jason explore the difference between saying thank you and expressing gratitude in a way that actually connects. Gratitude, they explain, is not just a statement—it carries emotion, intention, and meaning. When words and emotion don’t line up, even well-meant appreciation can feel hollow or disingenuous.

The conversation introduces a practical framework for expressing appreciation using the TSP model: Truthful, Specific, and Positive. Rather than defaulting to vague compliments, the goal is to notice what people actually do well, name it clearly, and deliver it in a way that builds others up. The discussion also touches on how understanding how others receive appreciation—through words, actions, or presence—shapes whether gratitude is felt or simply heard.

If you're looking for ways to improve how you connect with others, strengthen your presence in conversations, or build goodwill through intentional communication, this episode offers a thoughtful approach to making appreciation meaningful—especially during a season when words are plentiful and sincerity matters most.

The core message: Gratitude that is felt changes relationships. Gratitude that is rushed disappears just as quickly as it’s spoken.

Quick Poll: Is cup the worst example you ever heard? Let us know!

At Crossroads Business Development we are the recipients of the David H. Sandler award for 2021, the highest mark of achievement that the network passes out. We pride ourselves with our dedicated service to the success of our clients and our top-of-the-line training that keeps our clients engaged and coming back for more.

Jim Stephens is a dynamic and engaging conference presenter and national speaker, renowned for his impactful presentations at a wide array of sales and industry events. With an impressive twenty-five-year track record in entrepreneurial small business creation, sales, and company management, he brings a wealth of real-world experience. Additionally, Jim has spent two decades honing his expertise through Sandler Sales & Management Training, equipping him with the tools to drive success in any organization. His keen insights and ability to identify and address roadblocks are instrumental in fostering growth and transformation for individuals and companies.
📧 Reach out to Jim at: jim.stephens@sandler.com

Jason Stephens helps individuals and organizations turn goals into daily behaviors that drive measurable growth. Known for his structured, analytical approach, he equips clients with practical systems that turn complexity into clarity, and ideas into action. Whether he’s coaching a leader through change or building a sales process that sticks, Jason focuses on alignment, execution, and long-term success. Clients rely on him to uncover what’s really getting in the way, and to create frameworks that spark momentum—not just motivation. With a coaching style rooted in curiosity and accountability, Jason delivers tools that help people think clearly, act intentionally, and lead with purpose.
📧 Reach out to Jason at: jason.stephens@sandler.com

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In this episode, Jim and Jason explore how the information you consume directly shapes your beliefs—and how those beliefs influence every decision you make in sales, leadership, and your long-term success. Drawing on insights from an economics conference and ITR Economics' extraordinarily accurate forecasting model, they break down why mindset—not the market—is often the biggest threat to performance.

The conversation covers the danger of echo chambers, the need to audit the sources influencing your worldview, and how pessimistic narratives can become self-fulfilling prophecies. If you’re looking for ways to strengthen your Positive Outlook competency, this episode challenges you to separate data from drama, to recognize when your beliefs are drifting into scarcity, and to take back agency over how you interpret the world around you.

The core message: you don’t control the economy, but you do control the lens you bring to it—and that lens determines whether you see decline, possibility, or opportunity.

At Crossroads Business Development we are the recipients of the David H. Sandler award for 2021, the highest mark of achievement that the network passes out. We pride ourselves with our dedicated service to the success of our clients and our top-of-the-line training that keeps our clients engaged and coming back for more.

Jim is a dynamic and engaging conference presenter and national speaker, renowned for his impactful presentations at a wide array of sales and industry events. With an impressive twenty-five-year track record in entrepreneurial small business creation, sales, and company management, he brings a wealth of real-world experience. Additionally, Jim has spent two decades honing his expertise through Sandler Sales & Management Training, equipping him with the tools to drive success in any organization. His keen insights and ability to identify and address roadblocks are instrumental in fostering growth and transformation for individuals and companies.
📧 Reach out to Jim at: jim.stephens@sandler.com

Jason helps individuals and organizations turn goals into daily behaviors that drive measurable growth. Known for his structured, analytical approach, he equips clients with practical systems that turn complexity into clarity, and ideas into action. Whether he’s coaching a leader through change or building a sales process that sticks, Jason focuses on alignment, execution, and long-term success. Clients rely on him to uncover what’s really getting in the way, and to create frameworks that spark momentum—not just motivation. With a coaching style rooted in curiosity and accountability, Jason delivers tools that help people think clearly, act intentionally, and lead with purpose.
📧 Reach out to Jason at: jason.stephens@sandler.com

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n this episode, Jim and Jason explore the subtle, yet powerful skill of active listening in sales—and how it distinguishes top performers from average ones. Together, they reflect on the idea that credibility isn’t about what you know—it’s about what you notice. In a world where salespeople often feel the pressure to present, educate, or impress, this episode challenges that urge by highlighting the importance of slowing down, asking better questions, and helping your buyers feel seen.

Jason shares his thoughts on how practicing a consistent process allows for deeper focus on the person across the table, not just the sales tactic. Jim brings up two key Sandler rules:

• “You gain more credibility by the questions you ask than by the information you give,” and
• “Sell today, educate tomorrow.”

If you're doing most of the talking, you may be alienating buyers without realizing it. The duo urges listeners to consider: Are you truly present in your conversations? Or are you stuck in the cycle of over-explaining and under-connecting?

Whether you're trying to improve a sales call or build stronger client relationships, this episode reminds us that being curious and listening well is more persuasive than being the smartest person in the room.

🏆 About Crossroads Business Development:

At Crossroads Business Development we are the recipients of the David H. Sandler award for 2021, the highest mark of achievement that the network passes out. We pride ourselves with our dedicated service to the success of our clients and our top-of-the-line training that keeps our clients engaged and coming back for more.

Jim is a dynamic and engaging conference presenter and national speaker, renowned for his impactful presentations at a wide array of sales and industry events. With an impressive twenty-five-year track record in entrepreneurial small business creation, sales, and company management, he brings a wealth of real-world experience. Additionally, Jim has spent two decades honing his expertise through Sandler Sales & Management Training, equipping him with the tools to drive success in any organization. His keen insights and ability to identify and address roadblocks are instrumental in fostering growth and transformation for individuals and companies.
📧 Reach out to Jim at: jim.stephens@sandler.com

Jason helps individuals and organizations turn goals into daily behaviors that drive measurable growth. Known for his structured, analytical approach, he equips clients with practical systems that turn complexity into clarity, and ideas into action. Whether he’s coaching a leader through change or building a sales process that sticks, Jason focuses on alignment, execution, and long-term success. Clients rely on him to uncover what’s really getting in the way, and to create frameworks that spark momentum—not just motivation. With a coaching style rooted in curiosity and accountability, Jason delivers tools that help people think clearly, act intentionally, and lead with purpose.
📧 Reach out to Jason at: jason.stephens@sandler.com

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In this episode, we break down a subtle but important distinction in prospecting strategy: the difference between evergreen outreach and time-sensitive messaging. Jim and Jason explore how consistent, repeatable prospecting efforts (like evergreen campaigns) can build a reliable pipeline over time—while also recognizing when real-world events, market shifts, or internal changes demand a more responsive approach.

We explore metaphors like panning for gold and fishing, showing that successful salespeople know their “cookbook” behaviors and stay consistent—without relying solely on lead flow or waiting for the “right” moment to prospect. Instead, the challenge is to build systems that support steady outreach while leaving space to adapt when opportunities surface. If you’re looking for ways to sharpen your sales presence, apply consistent behaviors, or think more strategically about how you build your week, this conversation will offer both practical and mindset-based takeaways.

The core message: stop treating prospecting as an emergency response—build a system that works whether the river is flowing or not.

🏆 About Crossroads Business Development:

At Crossroads Business Development we are the recipients of the David H. Sandler award for 2021, the highest mark of achievement that the network passes out. We pride ourselves with our dedicated service to the success of our clients and our top-of-the-line training that keeps our clients engaged and coming back for more.

Jim is a dynamic and engaging conference presenter and national speaker, renowned for his impactful presentations at a wide array of sales and industry events. With an impressive twenty-five-year track record in entrepreneurial small business creation, sales, and company management, he brings a wealth of real-world experience. Additionally, Jim has spent two decades honing his expertise through Sandler Sales & Management Training, equipping him with the tools to drive success in any organization. His keen insights and ability to identify and address roadblocks are instrumental in fostering growth and transformation for individuals and companies.
📧 Reach out to Jim at: jim.stephens@sandler.com

Jason worked at the university before joining the team. He brings an analytical perspective to coaching and has several tracks to help with team and personal development. Our clients hire Jason for his systematic approach to help them integrate Sandler into their day-to-day operations. His attention to detail and expertise with our assessment tools help them create behavior-based plans to incorporate more processes and align their goals with the company's goals.
📧 Reach out to Jason at: jason.stephens@sandler.com

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In this episode, Jim and Jason explore the critical role of sales management—not as a title, but as a function—especially for companies transitioning from founder-led sales to team-based selling. If your team is hitting plateaus, missing follow-through, or struggling with inconsistency, the issue might not be your people—it might be the absence of management infrastructure.

They unpack why many salespeople underperform after being hired, how over-attributing outcomes to personality rather than process creates blind spots, and why founders often assume their salespeople will “just figure it out” the way they did.

You’ll hear insights on daily minimums, weekly review rhythms, and the importance of pipeline visibility as early warning signs. The conversation also touches on the dangers of conflating activity with progress—and how subtle feedback loops help teams stay aligned and engaged.

If you’re looking for ways to improve self-awareness and bring more structure to the way your team sells, this episode offers a practical approach to building the habits of sales management, even if you’re still wearing multiple hats.

The core message: Sales management is not optional—it’s a necessary ingredient for consistent growth. You don’t need a VP title to implement it. You just need a system.

🏆 About Crossroads Business Development:

At Crossroads Business Development we are the recipients of the David H. Sandler award for 2021, the highest mark of achievement that the network passes out. We pride ourselves with our dedicated service to the success of our clients and our top-of-the-line training that keeps our clients engaged and coming back for more.

Jim is a dynamic and engaging conference presenter and national speaker, renowned for his impactful presentations at a wide array of sales and industry events. With an impressive twenty-five-year track record in entrepreneurial small business creation, sales, and company management, he brings a wealth of real-world experience. Additionally, Jim has spent two decades honing his expertise through Sandler Sales & Management Training, equipping him with the tools to drive success in any organization. His keen insights and ability to identify and address roadblocks are instrumental in fostering growth and transformation for individuals and companies.
📧 Reach out to Jim at jim.stephens@sandler.com

Jason worked at the university before joining the team. He brings an analytical perspective to coaching and has several tracks to help with team and personal development. Our clients hire Jason for his systematic approach to help them integrate Sandler into their day-to-day operations. His attention to detail and expertise with our assessment tools help them create behavior-based plans to incorporate more processes and align their goals with the company's goals.
📧 Reach out to Jason at jason.stephens@sandler.com

Send us a text

In this episode, Jim and Jason reflect on how sales professionals can embrace change without losing sight of what makes us human. Drawing on decades of experience and recent AI innovations, they explore the real question behind all the hype: What does it actually mean to adapt to technology?

Jim shares how technology has evolved across his career—from pagers and fax machines to AI-powered roleplay coaches—and how resistance to change (like Blockbuster's refusal to buy Netflix) is more than a history lesson; it's a cautionary tale. Jason emphasizes how tools like ChatGPT or Sandler’s own Yoodli Roleplay Coach can help remove “blank page” paralysis, making it easier to build SOPs, brainstorm ideas, and reduce friction in sales processes.

Together, they explore a key attitude question: Are you curious enough to experiment with tools before you’re forced to catch up?

The more commoditized the world becomes, the more valuable strong communicators will be. Use technology as a force multiplier—but never lose the human edge.

🏆 About Crossroads Business Development:

At Crossroads Business Development we are the recipients of the David H. Sandler award for 2021, the highest mark of achievement that the network passes out. We pride ourselves with our dedicated service to the success of our clients and our top-of-the-line training that keeps our clients engaged and coming back for more.

Jim is a dynamic and engaging conference presenter and national speaker, renowned for his impactful presentations at a wide array of sales and industry events. With an impressive twenty-five-year track record in entrepreneurial small business creation, sales, and company management, he brings a wealth of real-world experience. Additionally, Jim has spent two decades honing his expertise through Sandler Sales & Management Training, equipping him with the tools to drive success in any organization. His keen insights and ability to identify and address roadblocks are instrumental in fostering growth and transformation for individuals and companies.
📧 Reach out to Jim at jim.stephens@sandler.com

Jason worked at the university before joining the team. He brings an analytical perspective to coaching and has several tracks to help with team and personal development. Our clients hire Jason for his systematic approach to help them integrate Sandler into their day-to-day operations. His attention to detail and expertise with our assessment tools help them create behavior-based plans to incorporate more processes and align their goals with the company's goals.
📧 Reach out to Jason at jason.stephens@sandler.com

Send us a text

In this episode, Jim and Jason unpack a hidden but critical force that shapes how we sell and how we live: our belief wheel. They walk through a powerful framework that starts with beliefs, shapes our judgments, guides our actions (or inaction), and leads to the results we keep repeating—whether we like them or not.

This episode zooms in on how that internal belief system reacts during periods of uncertainty. What happens when pricing, markets, or the world itself feels unpredictable? And more importantly, how do you respond instead of react?

The key takeaway: If you're feeling uncertain, the solution isn’t to analyze the uncertainty more deeply—it’s to take action. Not wild, ungrounded action—but thoughtful steps that challenge the default scripts running in your head.

If you're looking for ways to explore self-awareness, challenge your mindset around fear and decision-making, and take intentional steps forward even when the path isn't clear, this episode is a timely listen.

🏆 About Crossroads Business Development:

At Crossroads Business Development we are the recipients of the David H. Sandler award for 2021, the highest mark of achievement that the network passes out. We pride ourselves with our dedicated service to the success of our clients and our top-of-the-line training that keeps our clients engaged and coming back for more.

Jim is a dynamic and engaging conference presenter and national speaker, renowned for his impactful presentations at a wide array of sales and industry events. With an impressive twenty-five-year track record in entrepreneurial small business creation, sales, and company management, he brings a wealth of real-world experience. Additionally, Jim has spent two decades honing his expertise through Sandler Sales & Management Training, equipping him with the tools to drive success in any organization. His keen insights and ability to identify and address roadblocks are instrumental in fostering growth and transformation for individuals and companies.
📧 Reach out to Jim at jim.stephens@sandler.com

Jason worked at the university before joining the team. He brings an analytical perspective to coaching and has several tracks to help with team and personal development. Our clients hire Jason for his systematic approach to help them integrate Sandler into their day-to-day operations. His attention to detail and expertise with our assessment tools help them create behavior-based plans to incorporate more processes and align their goals with the company's goals.
📧 Reach out to Jason at jason.stephens@sandler.com