The Sales Evangelist

AI is changing sales fast. But is it actually replacing salespeople, or is it exposing the sellers who never developed real strategy skills? That’s the question I explore in this conversation with John Stopper. John and I get into the difference between sales tactics and sales strategy, why AI can sometimes give sellers the wrong picture of a buyer, and why getting closer to the people involved in a deal can make the difference between winning and losing. We also talk about how sales teams can use AI to identify deal risks instead of simply using it to write more emails. Why AI Makes Sales Strategy More Important AI can teach people sales tactics, but strategy requires a deeper understanding of the situation. Tactics focus on how to sell, while strategy focuses on who, what, when, where, and why. AI can help sellers execute many tactical tasks, but sellers still need to decide which approach fits the buyer and the situation. Strong sales strategy starts with understanding customers and what will actually compel them to buy. The goal is to choose the right strategy based on the conditions of the deal. Tactics vs. Strategy: The Baseball Analogy — 03:38 Knowing how to throw every pitch does not mean you know which pitch to throw. A baseball pitcher may have four or five pitches available. The right pitch depends on the batter, pitch count, runners on base, and inning. Sales works the same way. The skill is not just knowing the sales playbook but knowing which strategy to use in the moment. Choosing the right strategy can improve your position, accelerate velocity, and compress time. The Principle of Reality: Don't Trust Every AI Answer AI can give both buyers and sellers information that does not accurately reflect the current situation. Buyers can use AI to research a salesperson or company before the first conversation. Sellers can also build their account research around outdated or incomplete information. A polished AI summary can create false confidence if it does not reflect what is actually happening. Sellers should verify their assumptions instead of treating AI research as unquestionable fact. How to Surface Reality With Better Questions The first sales conversation is an opportunity to check whether both sides are working from the right information. Ask the buyer what their AI research has shown them about your company, product, or you. Share what your research has shown you about their company and ask whether you have it right. Use the conversation to identify what is missing from your research. Verify the situation before choosing your sales strategy. Different Buyers Require Different Strategies The right message depends on the person you are selling to. End users often care about doing their jobs faster, better, or cheaper. Managers may care more about how a solution affects their team and the risks involved. Executives are more likely to focus on strategic growth and business outcomes. Sellers need to understand the buyer's role before deciding what value to emphasize. The Principle of Proximity: Get Closer to the Buyer “Proximity sells” because sellers need to understand the buyer's world deeply enough to bring useful insight. Proximity is not about becoming the buyer's friend. It means understanding the buyer's business and seeing things from both inside and outside perspectives. Sellers should get close to the people who can influence the deal, not only the person who can approve it. Outside experience can help sellers bring insights the buyer may not have considered. Find the People Who Can Say No A deal can have strong champions and still fail because someone else inside the organization has the power to stop it. Identify the people who may resist the purchase. Ask your champion who in the organization could have concerns about the solution. Reach out to those people directly instead of waiting for their objections to appear later. Address potential resistance before it becomes a deal-ending problem. Use AI to Identify Deal Risk AI can be useful when it helps sellers think through what could go wrong. Ask AI to research the people and roles that may resist a purchase. Identify possible objections and resistance points before they appear. Continue updating the research as the deal progresses because new risks can emerge. Use AI to help build a deal strategy around what could prevent the deal from closing. Bridging Strategy: Build Relationships Across the Account One salesperson should not have to carry every relationship in a complex B2B deal. Sales managers can connect with the buyer's manager. Product leaders can connect with the buyer's technical leaders. CEOs can connect with other executives when the situation calls for it. Each person can carry a message that matches their role and expertise. Multiple relationships can help both companies become more familiar with each other. Why Executives Still Have a Role in Selling Executive involvement can be part of the sales process, especially when selling complex solutions. Executives have revenue responsibilities too. A salesperson can prepare an executive with the person's profile, the situation, the message to communicate, and the information to bring back. AI can take more operational work off the team's plate. That creates more room for leaders to spend time with customers and support revenue-generating conversations. Salespeople Need to Become Strategists As AI makes more sales information and tactics available, the ability to create useful insight becomes more important. AI has reduced the advantage that once came from simply knowing sales tactics. Sellers need to know how to use information, not just access it. The goal is to tell buyers something they do not already know. Strategy determines what insight to deliver, when to deliver it, and who should deliver it. Human-to-Human Selling Still Matters AI and digital tools should not replace direct conversations with buyers. At minimum, sellers should use video calls when meeting in person is not possible. Direct conversations can help uncover what digital research misses. Meeting a buyer in person can build trust and show a willingness to make an effort. Sales still depends on human relationships, especially when decisions are complex. Key Quote from the Episode “AI has commoditized a lot of that advantage. So now to me, selling and strategy is about how can I tell them something they don't know?” — John Stopper Resources: John Stopper: johnstopper.com John's website also offers a free, no-obligation deal strategy report. Submit a company you are trying to sell to, and he will run it through his COMPASS system and provide a deal strategy report. Email: J Stopper at Northstore.com LinkedIn: John Stopper Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

Connection rates have dropped roughly five times since before COVID. If ten percent of your calls used to turn into a conversation, you're probably closer to two now. David Zeff, CEO of Whistle, runs an agency that makes cold outreach work for 350-plus B2B clients, and he broke down exactly what's changed, what hasn't, and the parts of outbound most people are too embarrassed to actually do. Why Connection Rates Have Collapsed Since COVID David's headline stat: connection rates have dropped roughly five times since the early 2010s. If a rep used to get a conversation on ten percent of calls, that number is closer to two percent now. That drops compounds. Fewer conversations means fewer meetings booked from the same amount of effort, cutting a rep's effective output roughly in half even before factoring anything else in. He points out that most investors and boards setting revenue benchmarks don't actually understand how much this single number has shifted, which means the targets built on top of it are often unrealistic from the start. The Four Things Whistle Screens For Before Taking a Client Whistle turns away clients the way a lawyer might turn down a case they can't win. David treats a signed client as the start of the real work, not the finish line. First: does the founder actually know their ICP? If they're still deciding between multiple very different buyer types, that's a major warning sign. Second: is the total addressable market big enough to support a real sales motion, since a market of a few hundred accounts with multi-year sales cycles isn't a fit for most outbound efforts. Third and fourth: is there real marketing support behind the sales effort, and does the product have any real moat, since neither one used to be a dealbreaker a decade ago the way they are now. The New Risk: Can Your Prospect Just Build It Themselves? David's newest red flag: prospects increasingly ask themselves whether they could just build a simple version of the product using AI tools instead of buying it. His own team has looked at some clients' products recently and had the same reaction: this looks like something built quickly with AI, which means the prospect is likely to think the same thing. Sellers need a clear, early answer to that question, since it's showing up at the very top of the funnel now, not just at the negotiation stage. Why Cold Email Copy Isn't the Real Story Prospects often ask David to see a sample of Whistle's email copy, expecting the wording itself to explain the results. His answer is always the same: seeing the email is like seeing the cheese and asking how that made the pizza. The copy alone leaves out everything that actually got the message opened and read in the first place. Highly personalized details, like referencing someone's favorite sports team, used to work well on their own. David is direct that this stopped being enough years ago, even though it still gets attention on LinkedIn as a screenshot-worthy tactic. Stop Separating the Brand From the People David points to Gong as the company that got this right early: during the shift to remote work, they made individual employees visible instead of hiding behind the company logo, including putting reps on billboards. B2C brands have leaned on individual personalities for a long time. B2B is only catching up to that now, and companies that keep everything behind a logo are giving up a real advantage. Donald shared a reference point from a past guest at Chili Piper, who said roughly half the deals in their pipeline had some connection to her personal LinkedIn activity, not because she was directly involved in every deal, but because buyers had engaged with her content somewhere along the way. Build Community Before You Need It David's third layer, beyond the basics and personal branding: building some form of community or network around your business, even a small one. A simple example from one of his own clients: a marketing VP asked if Whistle could bring their clients together to trade notes, which turned into a referral network of consultants and adjacent service providers. It doesn't have to be a massive branded community. Even something as basic as a small referral relationship, a shared cause you donate to together, or a network of people adjacent to your buyer who can talk about your space, counts and compounds over time. The Free Tactic Nobody Will Actually Do David's final, deceptively simple tip: export your personal contacts from WhatsApp or your phone, write one honest message explaining what you do and asking for a referral, and send it to twenty people a day. His prediction is that most people won't actually do this, precisely because it's free, easy, and has no clever trick to hide behind if it doesn't work. He's currently running an open deal that came directly from this exact method, reaching out to a personal contact who referred him to someone else who's now moving through the sales process. "We're in sales. You're always desperate. That's the job." — David Zeff Resources Connect with David Zeff on LinkedIn. Visit Whistle to learn more about their outsourced sales development services. Join our LinkedIn cohort and learn to prospect the right way. Visit Blue Mango Studios for help creating podcast production content. Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

Sometimes the best way to close more deals isn't by adding new people to your pipeline (though that's always a good thing.) Instead, the best thing is to address the issues that make a deal fail before they fail. In today's episode of The Sales Evangelist, I joined the CEO of Challenger, Andee Harris, to get her take on failed deals and how to address those issues directly with our prospects. Challenger is a sales training company: The Challenger Sale by Matthew Dixon and Brent Adamson explains many of the principles Challenger uses in their training. Early sellers might be timid, which usually leads to a failure to recognize when a deal isn't moving in the right direction. In Andee's experience, continuous feedback is a great way to course-correct throughout the sales process to tailor the experience and selling strategy to the specific prospect. Passive selling isn't the best form of selling for either party. Taking control of the purchase and helping the buyer buy the product is your job. Three ways to notify deals before they go south: Integrate an avenue for continuous feedback. If a buyer likes you as a sales rep, they'll want to share methods to improve their experience. Realize that one size doesn't fit all. What works for one client might not work for another. Constantly be learning. Be curious, and look to understand and be self-aware of your strengths and weaknesses. Andee's final takeaway? Understand that we're in a complex selling environment. Multiple factors influence the selling process, but it isn't impossible to create wins and do phenomenally well. To get in touch with Andee, visit challengerinc.com or connect with Andee on LinkedIn. Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

A former Marine who did eight combat deployments in eight years now spends his time teaching people to stop pitching and start asking better questions. Keith Gillispie, founder of REI Automated, left the Marines in 2020 to build a real estate investing and coaching business that's helped more than 1,200 people, with close to 580 of them closing their very first deal. He broke down exactly how he qualifies, questions, and consults his way to the close. Why "Selling" Is the Wrong Mindset (Stop Being House Horny) Keith's blunt term for pushy sellers: house horny, chasing the deal so hard that they force the wrong solution onto someone just to close it. His fix is simple: stop selling, and start asking great questions that guide the prospect to the answer on their own. He reviews sales calls with his own team every week, and the biggest issue he catches with newer reps is a used-car-salesman energy that shows up the moment they stop asking and start pitching. Qualify for the Right Industry First Keith gets over a hundred Facebook messages a day, and his team has to pre-qualify people before he ever gets on a call. A recent example: a rep flagged someone as "qualified" who actually wanted coaching on commercial real estate, which Keith doesn't teach at all. Same broad label, completely wrong fit. Even inside a niche that sounds close enough, being in the wrong specific industry wastes everyone's time. Qualify for the Right Problem: Your Core Competency Must Match Their Core Constraint Keith's rule: everyone has problems, but that alone doesn't make someone a fit. What he's good at has to be exactly what the prospect is bad at. He calls this matching your core competency to their core constraint. If there's no real gap for him to fill, there's no real reason for the two of them to work together. This is what separates a win-win engagement from a sale that shouldn't have happened in the first place. Qualify for the Right Money (Or Every Call Becomes Charity) Even with the right industry and the right problem, a prospect still has to be able to afford the solution, or the call turns into free coaching. Keith shared a recent example of two prospects who badly wanted to join his program but couldn't spend even $300, when his coaching runs into the thousands. He's direct with his own team about this: sending him financially unqualified leads turns every call into charity work, which isn't sustainable as a business, even though he's genuinely happy to hand out free value when it makes sense. Diagnose Before You Prescribe Keith estimates that more than half of the people who come to him think they know what they need, and they're wrong. His example: prospects ask for automation when they don't even have leads coming in yet, or don't know how to structure a deal. Automating a broken process just scales the chaos faster. He compares it to a patient self-diagnosing before seeing a doctor. The seller's job, like a doctor's, is to ask enough questions to find the real issue before recommending anything. Get Comfortable Asking Uncomfortable Financial Questions Keith walks straight into questions like current income, whether that number is gross or net, and total debt, early in a call, because he can't build a plan without knowing where someone actually stands. He compares it to Google Maps: you need a point of origin and a point of destination before you can build the route in between. Roughly one in twenty-five or thirty people push back on how direct these questions are. Keith's response is straightforward: if they can't handle these basic questions now, the program itself is going to be a rough fit. Build Yes Momentum With Small Asks Keith structures his qualifying questions to build what he calls yes momentum: each small, reasonable question makes the next one easier to answer. He starts broad, what do you do, how long have you done it, before narrowing into income, debt, and financial specifics, so the conversation earns its way to the harder questions instead of opening with them. That same sequence doubles as training. The financial questions he asks on a discovery call mirror the exact questions his students will later need to ask sellers and private lenders. Ask Questions, Don't Make Statements Keith's rule for himself: don't make a statement for the first 60 percent of any sales call, aside from short softening statements like "I'm glad you asked that." The only exception is a brief acknowledgment before turning right back around and asking another question. Whoever is asking the questions is steering the conversation, and Keith treats that as true for the entire first half of every call he runs. Never Fully Answer a Question Without Asking One Back Keith borrows from Socratic questioning: when a prospect asks a direct question, like how fast he can close on a house, answering too quickly and too specifically can blow up the deal in either direction. Instead, he gives a partial, honest answer, then asks a question that uncovers the real reason behind their question, like whether they need to move fast or need more time. That extra step means his eventual answer is actually calibrated to what the person needs, instead of a generic response that might scare them off or fail to meet an urgent situation. Become a Lifelong Student of Your Craft Keith has taken more than ten thousand sales calls over eleven years and still says the more he learns about sales psychology, the more he realizes he doesn't know. His advice for anyone serious about improving: invest in a coach or mentor who can review real calls and point out specific gaps, rather than trying to learn everything for free through trial and error. His framing: you'll pay for the lesson either way, either in money to a mentor, or in wasted time and missed opportunity learning the hard way. "People don't care how much you know until they know how much you care." — Keith Gillispie Resources Connect with Keith Gillispie on LinkedIn. Visit REI Automated to learn more about Keith's education, software, and coaching community for real estate investors. Join our LinkedIn cohort and learn to prospect the right way. Visit Blue Mango Studios for help creating podcast production content. Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

37 reps who got the least recognition on one 153-person sales team averaged 62 percent quota attainment. The team average was 107 percent. That gap is the whole argument Sindre Haaland, CEO and founder of SalesScreen, makes for why comp plans alone don't explain sales performance. Why Identical Comp Plans Produce Wildly Different Results Sindre's core observation: two reps can work under the exact same comp plan and produce completely different results, which means money alone isn't the daily driver of performance. Comp plans set the structure and tell a rep what they need to do to get paid, but engagement is what determines whether they actually do it consistently. An engaged rep will outperform a disengaged one with the identical incentive on the table, every time. Know Your Sales Math Sindre's first question to any rep: have you actually broken your quota down into what you need to do today, not just what you need to hit by year end? Reps who treat sales as a series of repeatable, data-driven daily activities have a far more predictable path to their number than those relying on charisma alone. Even with a full pipeline of data, the numbers only matter if a rep has the motivation to actually execute the plan. That's the gap gamification is built to close. The Four Player Types on Every Sales Team Sindre borrows a framework from game theory to describe four types of sales reps: killers, achievers, explorers, and socialites. Killers are driven by being number one and seeing their name at the top of the leaderboard. Achievers care about personal bests, regardless of where they rank against everyone else. Explorers enjoy the process itself, testing new tools and new angles. Socialites, the majority of most sales teams, are driven by recognition, visibility, and feeling like their effort is seen. The TV and Music Moment That Changed Sindre's Career Sindre described watching a sales floor the first time his team replaced a whiteboard with TVs that played music and visuals every time a rep closed a deal. People were jumping on their desks. That reaction is what convinced him sales motivation itself, not another feature, was the real business to build. A rep's win becoming a shared, visible, celebrated moment does something a quiet bank deposit never will. Three Rules for Running a Contest That Moves the Needle Timing matters more than most leaders assume. Contests started on a Wednesday consistently outperform ones started on a Monday, since early-week motivation has usually faded by midweek. Shorter is better. Month-long contests tend to create a "valley of disengagement," with excitement in week one, a dead middle, and a scramble at the end. One-day sprints create urgency without the letdown. Change the format so more than the top performer has a real shot. A lottery-style contest, where every meeting booked or deal closed earns a ticket, gives the middle of the pack a genuine "I might actually win this time" feeling. Get Creative: Pairing, Envelopes, and the White Elephant Game Pairing a high performer with a lower performer on a team-based contest naturally creates coaching and mentorship, without ever calling it that. Simple physical mechanics work too: envelopes on a wall that reps can pick from after hitting an activity, some holding a dollar, some holding a bigger prize. Sindre's favorite: a white elephant style game where prizes range from real rewards to silly forfeits, and reps can steal from each other until the contest ends, creating genuinely memorable moments on the floor. The Recognition Stat That Proves the Point Sindre shared data from a 153-person sales team where they measured how often each rep received recognition in a month. The 37 reps who received the least recognition averaged 62 percent quota attainment. The team average was 107 percent. Recognition and quota attainment move together closely enough that Sindre treats recognition frequency as a leading indicator, not just a nice-to-have. Where to Start as a New Sales Leader Sindre's starting point for anyone new to this: interview your top performers and find out what they actually do every day, not just what the official process says they should do. Frequently, top performers are doing things nobody explicitly asked them to do, or doing an already-known behavior far more consistently than everyone else. Cross-check those behaviors against the rest of the team. Wherever the gap is real, that's where a leader's next contest or incentive should be aimed. "A motivated person will do better than a disengaged one, even with the same comp plan." — Sindre Haaland Resources Connect with Sindre Haaland on LinkedIn. Visit SalesScreen, the world's leading sales gamification platform. Join our LinkedIn cohort and learn to prospect the right way. Visit Blue Mango Studios for help creating podcast production content. Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.