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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.