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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