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Intro

Many talented professionals find themselves trapped by a "tolerance gap," where the fear of underdelivering or the subtle self-sabotage of the fear of success keeps them from turning their mastery into a thriving business. We often let amorphous anxieties—the "imposter" feeling or the worry of failing to meet expectations—prevent us from taking the calculated risks necessary for growth.

In this episode, Jim and Jason Stephens explore the psychological battle of balancing a growth mindset against the inherent risks of professional advancement. They break down how to ground your risk tolerance in reality and why "winging it" is often just as dangerous as total risk avoidance.

Key Topics Covered

• The Subtle Sabotage of the Fear of Success: While the fear of failure is a common motivator, Jim highlights that the fear of success is often harder to identify because it is so subtle. Subconsciously, professionals may fear that success will force them to live outside their comfort zone, requiring them to find new clients, generate revenue, and transform a passionate hobby into a high-pressure job.
• Naming and Granularizing Your Fears: Jason emphasizes that to overcome the things that prevent action, you must get "in the weeds" to define exactly what you are afraid of. By moving away from amorphous descriptions and getting as granular as possible—such as imagining the specific frustration of a partner or client—you can objectively evaluate the consequences of a risk.
• The Worst Case vs. Best Case Framework: Instead of being reckless or avoidant, the hosts suggest a deliberate risk assessment: identify the worst-case scenario, determine if you can live with it, and then decide if the best-case outcome is worth the fight. This calculation helps transition from "intuitive" risk-taking to a more effective "planning" approach.
• Building "Guts" Through Low-Stakes Practice: Jim shares an anecdote about his early days door-knocking, where he would sit in his car and realize the worst thing that could happen was being "thrown out by the scruff of the neck". By practicing courage in low-stakes environments like cold calling or door-to-door prospecting, you reap the benefit of "gut building" for the moments when the gain is truly sizable.

CHALLENGE OF THE WEEK

Identify a risk you have been avoiding and pinpoint your specific part in "not doing the thing". Stop defaulting to blaming your environment or external influences; instead, name the specific fear holding you back and evaluate whether the worst-case scenario is truly as dangerous as your mind has made it out to be.

The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development

We help sales professionals stop apologizing for their process and start closing deals.

👉 Catch the latest episode: The Sandler Training Hour

"Keep learning, stay curious, and good luck out there.

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Are you entering 2026 with a strategy, or just a "hope-based" mindset?

Many salespeople confuse a positive mood with a winning strategy, relying on hope that things will go well rather than executing measurable activities. If you feel like the world is going wrong, or if you are naturally skeptical, you might be sabotaging your own growth before the year even begins.

In this episode, Jim and Jason Stephens make the case for why 2026 is going to be the best year yet. They break down the mathematics of opportunity in the US economy and discuss the critical difference between consuming information and "shipping" results. Jim opens up about his own struggle with being a "glass half empty" person and the specific audit he uses to keep his mindset from becoming a constraint.

KEY TOPICS COVERED

The GDP Reality Check

Regardless of what the news cycle implies, business in America is on the rise. Jason breaks down the $43 trillion US GDP [correction, 29 trillion in 2024, 30 trillion in 2025] to illustrate that your specific sales goal is a tiny, achievable percentage of the available market. If you measure the math against the opportunity, success is realistic.

Attitude is a System, Not a Mood

Jason distinguishes between "mindset"—which can often devolve into hoping things go well—and "attitude," which is your core belief system. You cannot outperform your mental self-image; to have a great year, you must align your belief system with your behavior system.

Jim’s "Glass Half Empty" Audit

Jim discusses his personal battle with skepticism and "realistic" thinking that often masquerades as negativity. He details his process of auditing his thoughts to identify constraints and verifying his core values by looking at his calendar and checkbook. If you aren't investing time or money into a belief, it isn't a core value.

Shipping the Signal vs. Consuming the Noise

Jason introduces his potential themes for the year: "The Year of the Alchemist" and "Ship the Signal". The focus is on moving away from endless information consumption (digest) and prioritizing output (shipping projects) to avoid getting stuck in the noise.

CHALLENGE OF THE WEEK

Define Your 2026 Annual Theme.

Jim’s theme is "Choice," focusing on the decisions made in every moment, while Jason is focusing on "Input/Output". Your challenge is to determine your guiding theme for 2026. Ask yourself: Do your dreams feel random, or are they a result of what you are consuming?

Once you have your theme, share it with the team—if it's good enough, they might just steal it.

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.

The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development

We help sales professionals stop apologizing for their process and start closing deals.

👉 Catch the latest episode: The Sandler Training Hour

"Keep learning, stay curious, and good luck out there.

Send us a text

Most salespeople learn to treat an objection like a surprise attack—something they must battle with logic the moment it happens. However, this reactive approach usually leads to "salesperson ping pong," an argument where nobody wins and the prospect eventually shuts down.

In this episode, hosts Jason and Jim Stephens break down the concept of "objection awareness." They discuss why veteran salespeople should never be surprised by a roadblock and how to stop relying on creative improvisation in favor of a "locked and loaded" plan that disarms pressure and keeps the sale moving.

KEY TOPICS COVERED

• The "Creative" Bookkeeper Analogy Jim challenges the common resistance to using scripts: the fear of being inauthentic. He asks listeners to imagine a bookkeeper who decides to be "creative" every time they open an account rather than following standard accounting principles. Just as you want a bookkeeper who follows a process, successful selling requires following a system rather than relying on personality or "winging it".
• Building Your Objection Playbook If you have been in sales for more than a year, you have likely experienced every obstacle you are ever going to face. Rather than reinventing the wheel every time a prospect says "no," Jim and Jason advocate for building a specific playbook with pre-planned, multiple-choice responses for positive, negative, and neutral scenarios.
• Systematic vs. Gregarious Selling Jason highlights a paradox in sales: the "gregarious, people-oriented" salesperson often struggles because they rely on their ability to improvise and "be genuine" rather than planning. Conversely, systematic people often adapt to Sandler faster because they are concerned with "not knowing what to do," forcing them to build a plan before they act.
• Reviewing the Game Tape Self-awareness is critical for growth. Jim shares his personal practice of reviewing video recordings of his Zoom sales calls to analyze his reactions under pressure. The camera doesn't lie, and reviewing these interactions helps eliminate nervous habits—like awkward laughter—that devalue the conversation.

CHALLENGE OF THE WEEK

This week, Jason wants you to audit your obstacles before your next set of sales calls.

Write down the three objections you hear most often. Do not try to solve them yet—simply list them. Once you see them on paper, they start being problems you can proactively plan for.

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.

The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development

We help sales professionals stop apologizing for their process and start closing deals.

👉 Catch the latest episode: The Sandler Training Hour

"Keep learning, stay curious, and good luck out there.

Send us a text

You can have the perfect script and the perfect product, but if you don't have the agility to adapt to the market, you will lose the deal to the competitor who does. We often think technology is just about the tools, but it is actually about how you show up when the ground shifts beneath you.

In this episode of The Sandler Training Hour, Jim and Jason Stephens discuss the "Adaptability Quotient" and why the speed at which you embrace change distinguishes average reps from top performers. They explore the integration of AI not as a replacement for human connection, but as a tool to sharpen your skills in a risk-free environment.

Key Topics Covered:

The Rate of Change Axiom: Jim lays down a fundamental rule: If the rate of change within your organization is slower than the rate of change in the culture, you are going to be left behind. Being an "early adopter" offers a higher probability of success than being a laggard because delay simply gives your competition an advantage.

"Creative Accounting" & Just Starting: Jim shares a story about buying his first computer—a 256k model—and how his early attempts at digital ledgers were messy but necessary steps toward modernization. The lesson? You have to be willing to make mistakes. If you are waiting for the perfect path to appear, you are already too late.

Risk-Free Roleplay: One of the most powerful applications of AI is using it to practice Sandler strategies, like Upfront Contracts, without burning productivity. Practicing on a prospect is dangerous; practicing with a coworker costs company time. AI allows you to simulate objections from "skeptical" or "blunt" prospects so you can practice in a safe environment.

The Emotional Buffer: Jim reveals a personal "hack" for handling conflict. When he receives an email that makes him angry, he uses AI to rewrite his response. It removes the emotional undercurrents that might ruin a relationship and often provides a more effective, diplomatic solution than he would have consciously drafted.

Challenge of the Week:This week, Jim and Jason challenge you to audit your Internal Rate of Change. Identify one AI tool or future tech you have been ignoring because it feels uncomfortable. Spend just 20 minutes this week experimenting with it. Don't try to master it—just prove to yourself that you can adapt.

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.

The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development

We help sales professionals stop apologizing for their process and start closing deals.

👉 Catch the latest episode: The Sandler Training Hour

"Keep learning, stay curious, and good luck out there.

Send us a text

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 act

The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development

We help sales professionals stop apologizing for their process and start closing deals.

👉 Catch the latest episode: The Sandler Training Hour

"Keep learning, stay curious, and good luck out there.

Send us a text

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

The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development

We help sales professionals stop apologizing for their process and start closing deals.

👉 Catch the latest episode: The Sandler Training Hour

"Keep learning, stay curious, and good luck out there.

Send us a text

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

The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development

We help sales professionals stop apologizing for their process and start closing deals.

👉 Catch the latest episode: The Sandler Training Hour

"Keep learning, stay curious, and good luck out there.

Send us a text

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

The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development

We help sales professionals stop apologizing for their process and start closing deals.

👉 Catch the latest episode: The Sandler Training Hour

"Keep learning, stay curious, and good luck out there.