The Sandler Training Hour

Hosted by Jim Stephens

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127

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Aug 2026

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EN-US

About the show

Join Jim and Jason Stephens for weekly insights on the Sandler Selling System, navigating the modern sales landscape, and overcoming real-world business challenges. A Sandler Trainer is a salesperson. We lead by example and talk from experience. Reach out to us: Jason.Stephens@sandler.com Visit our website: https://go.sandler.com/crossroads/

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September 7, 2026Episode 7211 min

Stop Treating AI Like a Smarter Google

You tried AI, walked away unimpressed, and quietly filed it under overhyped. Most salespeople did the same. The tool is not the problem. The problem is that you are treating a machine like it is intelligent, when the intelligence in the exchange is yours. On this episode we make the case that AI is not artificial intelligence at all. It is a machine that does what it is told, and it will draw conclusions and hand you a generic deliverable the moment you give it a vague request. If you have only ever used it as a faster Google, you have seen the shallow end and assumed that is all there is. Learning how to use AI in sales starts with a different posture. Why AI keeps giving you generic answers It has no context for who you are or what you do, so it fills the blank field with the most predictable version of what you asked for. Feed it a vague prompt and it builds a house on an empty lot. Think like the architect, not the customer Jim spent his career in design sales, painting a picture for clients and then building it. That is the posture that works with AI. See what you want clearly, supply the context only you have, and help the machine catch the vision. Build guardrails that make it ask questions Left alone, AI jumps the gun and gives you what it thinks you want. Force it to slow down and ask you questions first, the same way discovery works in a real sales conversation. Start with one repetitive process you already own Do not try to automate your whole job. Take one process you run every week, document the steps, and build it with AI collaboratively. Jim records every sales conversation, uploads it, and lets AI handle hours of back-end work, then scores the call so he can see what he missed. Why resistance is a "you" problem AI is going to level the technical playing field. When that happens, the difference maker is the thing people-oriented sellers already own, the ability to communicate with another human. Sit out the shift and the gap only widens. Pick one repetitive process in your work this week, describe it out loud, and build the first rough version with AI. Start there. The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development 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. 📧 Reach out: jason.stephens@sandler.com 🌐 Crossroads Business Development

August 31, 2026Episode 7111 min

The Small Stumbles That Cost You the Sale

You lost the deal, and looking back it is easy to point to the one moment it fell apart. The prospect who went quiet. The price that scared them off. The close you fumbled. Hindsight makes it look like a single mistake. It almost never is. In this episode we look at why deals actually die. Not in one big misstep, but in a series of small stumbles that pile up across a process you never fully defined. When you cannot name your own steps, you cannot see where a deal slips away, so you blame the prospect or the close for a problem that started far earlier. **Why we blame the wrong thing.** A loss feels personal, so we externalize it. Bad prospect, wrong timing, someone else's fault. We protect the ego, and in doing it we skip the honest audit that would make us better. **The budget conversation that never happened.** Jim walks through a kitchen remodel he lost long before the close. A couple he liked, a proposal built page by page, and the color draining from the wife's face when the number landed at over eighty-five thousand dollars against the twenty she had pictured. The deal did not die at the close. It died at the question he never asked: "Rough numbers, what are you thinking about investing?" **The three qualifiers that hold a deal together.** Pain, investment, and decision. A compelling reason to act, the willingness to invest time, money, and energy, and a clear read on how they decide and who they lean on. Get those straight before you build anything. **Micro yeses before the macro yes.** A yes on a deal is not one yes. It is a string of small agreements, from the up-front contract through every meeting, until the prospect trusts you enough to say let us do business. If your close rate frustrates you, the fix is probably not a sharper closing technique. It is a process you can actually see, so you can find the step where deals leak out. If this one resonates, go back to Episode 45, "Stop Winging It: Building a Sales Playbook That Actually Closes Deals," where we build the defined process this conversation argues for. The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development 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. 📧 Reach out: jason.stephens@sandler.com 🌐 Crossroads Business Development

August 24, 2026Episode 7010 min

What Avoiding the Uncomfortable Sales Calls Is Costing You

You know the calls you should be making. The past client you have not spoken to in a year. The prospect who went quiet after a strong conversation. You keep finding a reason to make them tomorrow, and tomorrow keeps moving. This week we get underneath why the uncomfortable sales activities keep sliding, and the answer is not the one most salespeople reach for. The problem is rarely a missing technique or a shortage of confidence. It is a commitment gap wearing an attitude gap as a disguise. Comfort is a commitment problem, not a skill problem "If only I had the right technique, or if I felt more comfortable talking to people, I would prospect more." That sentence sounds like an attitude. Underneath it sits the real issue: I have not committed to doing what the job requires. We talk about why you win every argument you have with yourself, and how naming that pattern is the first honest step out of it. Honor the fear before you fight it Your comfort zone is not your enemy. It is your sphere of expertise, and the hesitation you feel at its edge carries a seed of truth worth respecting. We walk through the fear of calling a past client, the story your brain tells to keep you safe, and why honoring that fear beats pretending it away. Pain by numbers Commitment needs a reason with a number attached. We work through quantifying what avoidance costs you: the conversion math on the activities you skip, the average value of the opportunities you are comfortable closing, and the money left on the table when you choose not to act. A decision not to make a decision is still a decision. Work the whole relationship, not only the close If you close at eighty percent, you can grind that number to ninety. The larger return sits earlier, in the engagement steps you skip because they feel uncomfortable. We make the case for leveling up where the lack is, rather than pouring all of your effort into the closing conversation and earning the pushy-salesperson label in the process. You cannot tell yourself into change People struggle to buy from a teller for the same reason you struggle to tell yourself to change. Telling is not conviction. We close on the move that works instead: commit to clarity about what you are trying to change, then define the specific behaviors that move the needle a week or a day at a time. If this one lands, start with the small thing this week. Pick the single behavior outside your comfort zone that you have been deferring, name what avoiding it costs you, and do it once. The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development 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. 📧 Reach out: jason.stephens@sandler.com 🌐 Crossroads Business Development

August 17, 2026Episode 6912 min

Why You Keep Chasing Prospects Who Never Decide

You present your best work, the prospect nods along, and then the conversation goes cold. You follow up once, twice, and eventually they land in a pile you check on for the next nine months. In this episode we look at why that happens, and it usually traces back to the level of pain you never reached. We spend the hour on the third level of pain, personal impact, and how it changes depending on whether you are selling to a business or to a person. Pain instead of a pitch. Traditional selling paints the best possible picture and waits for the prospect to react. We invert that. Rather than hoping our strengths happen to match their problem, we start from what the buyer actually cares about and work from there. The three levels of pain. Symptom, business impact, personal impact. We walk through all three and show why most sellers stop at the surface. In B2C, the middle level often shows up as family or community impact rather than pure business cost. Whose money is on the table. The core distinction of the episode. In a B2B deal you are helping someone spend other people's money, so personal impact is mostly about perception: how peers, a boss, and the wider market will judge the decision. In a B2C deal the buyer spends from a finite personal pool, with competing priorities pulling at the same dollars. Permission to ask the hard questions. For most sellers the barrier here is permission. We talk about why so many of us avoid the questions that move past surface symptoms into what the buyer thinks and feels, and what it costs us when we skip them. Quantify the cost and the budget appears. We work through a simple way to put numbers on a recurring problem in a B2B deal, and why no company lets a large enough problem sit unsolved just because it was not in the plan. Pain by persona. Every deal has stakeholders who are not in the room. We cover how to map buyers by role, why a contractor and a first-time buyer need different conversations, and how to surface the objections of the person who never showed up before they cost you the sale. If you have been collecting think-it-overs and blaming the prospect, this one gives you a more useful place to look. It is built for sales leaders and salespeople who want fewer stalls and cleaner qualifying, in both B2B and B2C. The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development 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. 📧 Reach out: jason.stephens@sandler.com 🌐 Crossroads Business Development

August 10, 2026Episode 6811 min

Why Prospects Shut Down When You Try to Overcome Their Objections

You had the answer ready. You delivered it cleanly. And the prospect pulled further away. That pattern has a cause: every time you argue with a hesitation, you confirm the stereotype the buyer walked in with before you said a word. This week we continue our conversation on objections with the core Sandler position: overcoming an objection is the prospect's work, and your job is to help them do it. We walk through what that sounds like on a live call, from the first playback to the moment a stalled deal clarifies itself. Objections are opinions Jim reframes the whole category. An objection is a thought the prospect chose to say out loud. When you hear it as an attack, you get defensive and telegraph it. When you hear it as an opinion, you can acknowledge it and open the dialog instead of shutting it down. The playback that builds trust Before you respond to any hesitation, restate it: "What I'm hearing you say is that moving forward feels like it could create these consequences. Is that what I'm hearing?" The prospect feels heard, and a prospect who feels heard will listen to you. "I have a different perspective. Would you like to hear it?" Jim's follow-up once the playback lands. In 25 years of using it, nobody has said no. When "we need to think about it" means no The gentle put-off. Jim repeats the prospect's words verbatim, then offers a story: often when people say that to me, what they mean is they don't want to move forward and don't want to hurt my feelings. Could that be happening here? Either they confirm the soft no, or they name what they actually need to process, and now you can coach them through it. Questions that quantify commitment On a scale of 1 to 10, where will this project be a year from now? How many minutes a week do you spend thinking about this problem? Clarity questions like these are how to respond when a prospect says they need to think about it without fighting them for the deal. Referrals over close rate The tree metaphor: conversations are the branches, and fruit shows up at the end of some of them. Competence demonstrated on a call brings warm referrals, even from people who were never a fit themselves. Try this before your next call: notice what you feel the moment an objection lands. Defensiveness telegraphs through the phone. Empathy is what opens a prospect to a different perspective. If this resonated, check out last week's episode where we cover why think-it-overs trace back to how you open the meeting. The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development 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. 📧 Reach out: jason.stephens@sandler.com 🌐 Crossroads Business Development

August 3, 2026Episode 6712 min

Why Prospects Keep Saying They Need to Think It Over

The call goes well. The prospect nods along, says it all makes sense, then asks for the weekend to think it over. You follow up, they go quiet, and your pipeline fills with maybes that stretch your sales cycle another month. This week we kick off a two-part series on objections, starting with the most common stall in sales: think it over. We dig into why salespeople who walk in expecting a stall almost always get one, and how to build the answer into your process before the objection ever surfaces. Part two drops next week, where we widen out to handling objections in general. Set the outcomes before the call starts We walk through the up-front contract and the exact language for naming three outcomes at the top of a call: we move forward, it's not a fit and we part ways, or it's a yes but not right now. When the buyer agrees to a decision structure in advance, the end of the call stops feeling rushed and starts feeling expected. Stop being a professional visitor Jim owns up to the years he spent avoiding assertiveness because he didn't want to feel aggressive, softening every expectation with wishy-washy language. We talk about why high urgency, moving every meeting to a logical next step, is the ingredient that separates a closer from a visitor. You are the easiest person to sell You know your own objections better than anyone. If commitment stays optional in your own head, you'll win every internal negotiation and change nothing. We connect this to why getting more informed can feel like progress while your behavior stays exactly the same. Practicing in your head is not practicing. The response that opens the real conversation Even with clear expectations, some buyers will default to a stall. Jim shares the word-for-word response we recommend, built on candor and nurturing, that surfaces what the prospect is actually thinking without putting them on the defensive. If you're getting a lot of think it overs, here's the question to sit down with this week: what are you doing to set the expectation for one? Look at your current process and find where the stall gets invited in. The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development 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. 📧 Reach out: jason.stephens@sandler.com 🌐 Crossroads Business Development

July 27, 2026Episode 669 min

Why Your Sales Conversations End in Assumptions Instead of Agreements

You walk out of a first meeting and something nags at you. Was that person being straight with you? You have no evidence either way, so you fill the gap with a guess. Your prospect is doing the same thing about you. This week we get into clarity, and what happens to a sales relationship when nobody asks for it. When you stop questioning what someone says, you start reading into what they don't say. Suspicion builds on both sides, neither person names it, and the deal stalls for reasons that never make it into the CRM. Topicality: define the terms before you argue the substance Jason brings in a rule from high school debate. Before you touch the substance of an argument, you define the terms. Get loose with a definition and you can spend an hour taking positions that never touch what the conversation was actually about. Sales calls run the same way. Two people say "budget" or "decision" or "next steps" and mean four different things. Be impeccable with your word Jim pulls the first of The Four Agreements into the conversation and adds the working translation: the goal is not the message you mean to send, it's the message the other person receives. That means translating Jim speak into Jason speak. Behavior style, background, how they think. The more you know about the person, the more precise your words can get. Two people, two scripts Every conversation is two accumulated scripts running at each other. Autopilot is easier, and staying present all day will exhaust you. In sales those scripts were built as a means to an end, and that is exactly what makes a salesperson feel salesy. Nobody wants to be sold. People do need help buying. Taking the push out Jim walks through leading the witness, and why a strong personality type gets more persuasive in their own head and more pushy in everyone else's. His counterweight: you're an expert on your subject matter, not an expert on the person across from you. From there we get into negative reverse selling as a way to remove the push entirely. Suspicion is a bad foundation Two people trying to build a relationship while quietly suspecting each other end up with a bad relationship and a set of assumptions they carry into the next one. Asking clarifying questions before you agree to anything protects both of you. The takeaway Jason lands on at the close: if you want clarity from other people, be clear yourself, and get comfortable with them asking you for it. The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development 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. 📧 Reach out: jason.stephens@sandler.com 🌐 Crossroads Business Development

July 20, 2026Episode 659 min

Why Prospects Take Your Free Advice and Never Buy

A prospect says the words every seller wants to hear: I need help. You show them everything you know, they thank you for the advice, and the deal goes nowhere. If that pattern sounds familiar, this episode names what is causing it. This week we dig into what happens in the seconds after someone asks for help, and why the instinct to start fixing costs sellers deals, leverage, and time. Most people in business development are natural problem solvers, and that reflex is exactly the trap. The inbound lead trap An inbound lead lands squarely in your wheelhouse and the happy ears switch on. We walk through why giving a prospect the information that lets them judge you, before you gather the information that lets you qualify them, puts you in a lose-lose position from the first call. Unpaid consulting Jumping straight to solutions earns you plenty of referrals, and almost none of them pay. We break down why free fixes get politely received and rarely acted on: a prospect who has not shared everything they know will treat any answer as half baked. Gauge commitment before you prescribe Having a problem is not the same as being willing to invest time, money, and energy in solving it. We cover why measuring commitment is the first job when someone says they have a problem, and what happens when you skip it: you insert yourself into a feedback loop you will grow to resent. The problem they bring is never the real problem Nine times out of ten, what a prospect describes is the surface indicator. What they are actually saying is: I am stuck, help me think through this. We connect this to why some companies live with surface-level problems forever. The ego underneath chronic fixing The uncomfortable part of the conversation. If you are compelled to answer every question, you are getting a need met: being needed, being appreciated, staying in the thick of things. Jim owns his own history as a chronic fixer and the value he lost to it. Facilitate discovery instead The job is not solving problems. The job is facilitating discovery, then reaching a mutual agreement about next steps. We also get into why the word itself matters: framing a call as discovery instead of a sales call changes how you show up, because mindset has to drive behavior. The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development 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. 📧 Reach out: jason.stephens@sandler.com 🌐 Crossroads Business Development

July 13, 2026Episode 6412 min

Why You Chase Prospects Instead of Asking for the Next Step

You avoid pushing because you do not want to look like the stereotypical salesperson. So you soften, you hedge, and you leave calls without a firm next step. Then you spend the week chasing. The problem is not that you are too aggressive. It is that fear of aggression has quietly turned you into a professional visitor. In this episode we separate assertiveness from aggression and show why the gap between them is where most sellers lose clarity, and deals. Why your read on your own assertiveness is unreliable We open with an uncomfortable truth: your sense of how assertive you are is subjective. It is anchored in how you were raised. Jim describes being told by his wife, "why did you say that," about a comment he did not even register as sharp. If you lean passive, asking for help or interrupting a server can feel aggressive. If you lean forward, you may run over people without noticing. You cannot calibrate off your own perception, so we look at what the situation actually requires instead. The fire hydrant problem Jim tells the story of learning to ride a bike, fixating on the one fire hydrant down the sidewalk, and hitting it. Sellers do the same thing. They stare at the salesperson stereotype they are trying to avoid and steer straight into it. The fix is not to focus harder on what to avoid. It is to map where you actually want to go. Assertive and permissive at the same time Being assertive does not mean pressuring the buyer. We break down how to hold your position while leaving the decision genuinely in the buyer's hands: "I am here to help you decide whether you want this or not. It is completely fine if you don't." Most buyers reached out because something has been frustrating them for months. They are closer to a decision than you think, and pressure is the wrong tool. The clear future commitment We get into the Sandler idea of never ending a call without a clear future commitment: a scheduled meeting on the calendar, a mutually agreed agenda, and a defined outcome. For a lot of people who come to Sandler, that feels almost unthinkable, so they chase instead. We make the case that direct leadership, being crystal clear on when you meet and what happens next, is the healthiest way to move from passive to assertive. Why a plan beats courage Conversations move at a thousand miles a minute. If you have to summon nerve in the moment and invent the words on the spot, you will find every wrong way to say it. We compare it to a shooter at the three-point line who has repped the motion enough that it runs on autopilot. Assertiveness with a plan is not a complicated move. If you tend to avoid being direct because you do not want to pressure anyone, this one reframes the whole thing. The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development 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. 📧 Reach out: jason.stephens@sandler.com 🌐 Crossroads Business Development

July 6, 2026Episode 6312 min

Why One Hard Conversation Never Fixes the Problem

You finally had the hard conversation. You said the thing you had been avoiding. A week later the same behavior is back, and now you are bracing to have the exact same talk all over again. This week we get into the part of hard conversations nobody prepares you for: the follow-up. One conversation does not buy permanent compliance, and no human has ever worked that way. We break down why the reminder matters more than the confrontation, and why quietly treating a person as a problem to fix turns the whole relationship into a game. Five Seconds of Courage Gets You Started; the Follow-Up Gets You Results Working up the nerve to open a hard conversation is a real hurdle. We talk about why thought precedes action, and how our own supposition about the other person's reaction stops us before we say a word. But the courage to bring it up is only the first half. The harder skill is what you do the second, third, and fourth time the issue surfaces. Compliance Is Not a Magic Button A lot of us manage the way a bad manager once managed us: through compliance only. We walk through why that fails, using a simple example of an employee who keeps showing up late. Telling someone to stop is not leadership; finding the gap between what they intend and what they actually do is. Stop Fixing the Person; Start Helping Things Go Right Here is the reframe that changes the conversation. When you treat a person as a problem to fix, you have turned them into an object, and controlling an object that has free agency is manipulation. We swap the fix-it demand for a better question: "How can I help you be on time?" Same issue, completely different posture. It puts ownership where it belongs and takes the finger-pointing out of the room. The General Process Fails the Specific Person Define your process so tightly that every prospect and every person gets handled the same, and you have solved for a category while ignoring the individual. We get into why the payoff grows the more you understand what makes each person different, and why the most efficient move is rarely the most effective one. If you have ever caught yourself thinking "they must have forgotten," or repeating the same feedback until you are sick of your own voice, this episode is about what to do instead. The Sandler Training Hour Hosted by Jim & Jason Stephens | Crossroads Business Development 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. 📧 Reach out: jason.stephens@sandler.com 🌐 Crossroads Business Development