AI Didn't Kill Sales Strategy. It Exposed Who Never Had One | John Stopper - 2038

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 ImportantAI 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 — 03:38Knowing 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to research a salesperson or company before the first conversation.Sellers can also build their account research around outdated or incomplete information.A polished AI summary can create false confidence if it does not reflect what is actually happening.Sellers should verify their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 StrategiesThe 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 StopperResources:John Stopper: johnstopper.comJohn'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 StopperSponsorship OffersThis 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.CreditsAs 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, <a...

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 COVIDDavid'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 ClientWhistle 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 StoryProspects 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 PeopleDavid 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 ItDavid'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 DoDavid'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 ZeffResourcesConnect 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 OffersThis 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.CreditsAs 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 OffersThis 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.CreditsAs 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 FirstKeith 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 ConstraintKeith'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 PrescribeKeith 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 QuestionsKeith 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 AsksKeith 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 StatementsKeith'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 BackKeith 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 CraftKeith 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 GillispieResourcesConnect 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 OffersThis 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.CreditsAs 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 ResultsSindre'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 MathSindre'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 TeamSindre 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 CareerSindre 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 NeedleTiming 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 GamePairing 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 PointSindre 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 LeaderSindre'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 HaalandResourcesConnect 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 OffersThis 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.CreditsAs 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.

Only 10 percent of sales messages actually explain why something should matter to the buyer. The other 90 percent are just decoration on a generic pitch. That stat comes from Leslie Venetz, who audits thousands of sales messages every year and just released her USA Today bestseller, Profit-Generating Pipeline. She broke down what real relevance looks like, and the exact method she uses to build it.What Relevance Actually Means (And Why Most Sellers Miss It)Leslie defines relevance simply: a message has to be relevant to the person receiving it, not to the seller sending it.The biggest problem she sees is that most outreach centers on the seller's process, product, and company goals instead of the buyer.When she audits sales messaging, and she reviews thousands of messages a year, only about 10 percent actually explain why a piece of information should matter to the prospect.The Mail Merge Era: When "Fake Personalization" Felt Like MagicBack around 2012, Leslie ran a basic mail merge strategy that felt groundbreaking at the time. Prospects were genuinely impressed just to see their name and company pulled into an email.That tactic hasn't disappeared. It's evolved into things like mentioning a prospect's new job title or congratulating them on a funding round.The problem is the same one it's always been: something can be true about a prospect without being relevant to them right now.Personalization Versus RelevanceLeslie draws a clear distinction: personalization is a fact about the prospect. Relevance is why that fact should matter to them today.I shared my own experience of digging through my inbox after the pandemic and realizing most pitches weren't even relevant to my actual role, let alone my actual problems.The real gap, in Leslie's words, is that most sellers never get into the buyer's emotional state, the specific pressure a person is under right now, not just their job title or industry.The Earn the Right Philosophy: De-Centering Yourself From the PitchLeslie's core philosophy is called Earn the Right: before asking for a meeting, a call, or a contract, a seller has to earn the right to that person's attention.That means shifting language away from "I'm an account executive at [Company] and we sell [Feature]" toward messaging built entirely around the buyer's specific situation and outcome.The shift shows up in something as simple as word choice. Leslie says the biggest difference she sees in client messaging is emails that stop being about I, we, and our, and start being about you and your.The Five-Filter Segmentation MethodLeslie's starting point for anyone new to territory planning is the five-filter method: four firmographic filters plus one demographic filter, layered together to turn a broad list into a hyper-specific one.She recommends starting with the demographic filter first, since narrowing a title, like going from "IT executives" down to just "CIO," forces a seller to ask what that exact role actually cares about.That one change alone, narrowing from a broad title to a specific one, has increased reply rates by more than 12 percent for her clients.A Real Client Example: Narrowing a Healthcare IT ListLeslie walked through a real example from a global software company: a list originally aimed at "IT executives in healthcare" got narrowed down using all five filters.The firmographic filters included US-only, hospitals specifically, revenue between 100 million and a billion dollars, and customer service departments over 100 people.They also added a signal: whether the hospital had missed a recent best-of list. That detail alone reframed the entire pitch around better patient outcomes and service rankings, instead of generic product features.Shorter Emails, Longer CadencesA common mistake Leslie sees even after sellers embrace outcome-focused messaging: trying to cram everything they want to say into a single email.Her fix is to trust the cadence. Spread the story about a buyer's likely outcomes across multiple touches instead of one dense pitch.That shift also means holding off on a hard call to action early in a sequence, and letting later touches carry more of that weight.Why "More" Isn't a StrategyWhen results slow down, Leslie sees most teams reach for the same lever: hire more reps, send more emails, make more calls.Her pushback is direct: more is never the answer on its own, because it skips the harder work of understanding who you're actually talking to.Good segmentation is what makes every other activity, calls, emails, cadences, actually worth doing in the first place.The Marriage of Art and Science in SalesLeslie pushes back on using AI as a way to fully remove the seller from the process. If a prospect is expected to give their time and attention to a reply, the seller owes them a message that was actually written with care.The science side is the data: confirming you're talking to the right person, at the right account, about the right thing.The art side is judgment: knowing that just because something is technically personalized, like mentioning a promotion, doesn't mean it's the most relevant or human thing to say next.One Thing to Do Right Now to Get More RelevantLeslie's starting point for any sales leader: audit your current sales messaging and count how often it uses I, we, my, and our instead of you and your.That audit gives you real data on how self-centered your outreach actually is, even if it doesn't feel that way from the inside.From there, use AI for research instead of mass automation. Learn what a specific persona at a specific type of account actually cares about, then build that into the message."More is not a strategy." — Leslie VenetzResourcesGrab Leslie's book, Profit-Generating Pipeline: A Proven Formula to Earn Trust and Drive Revenue.Visit Leslie's company, The Sales-Led GTM Agency.Connect with Andy Paul, Leslie's mentor and host of The Win Rate Podcast, on LinkedIn.Join our LinkedIn cohort and learn to prospect the right way.Visit Blue Mango Studios for help creating podcast production content.CreditsAs 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.

Imagine doubling your close rate and cutting your sales cycle in half. That's not a hypothetical. It's exactly what Pieter Leenhouts and his team did at Tax Guard, a Cogency Global company that sells to banks and financial institutions.Pieter walked me through exactly how they pulled it off, and it wasn't magic. It was math, structure, and a relentless focus on the front end of the pipeline.Why Their Sales Cycle Was So Long To Begin WithTax Guard's solution was new to the financial institutions they sold to, so reps had to spend real time educating buyers before those buyers even understood why they needed it.That education requirement, combined with deals that stalled out with the wrong contacts, created a long sales cycle and a lower close rate.Fixing it started with the pipeline itself, not with pushing reps to work harder.Give Every Rep the Right Size Pipeline, Not Just More DealsPieter's team found that around 120 opportunities was the right pipeline size for most of their account executives, though the number flexes based on how efficient a rep is.Instead of leaving reps to self source every opportunity, the team loads a portion of that pipeline for them, so reps spend more time working real opportunities and less time hunting for net new business.Their market of five to ten thousand financial institutions is well defined, which makes it possible to plan pipeline size with real precision instead of guessing.Split the Pipeline: 70 Percent Pre-Handraiser, 30 Percent Post-HandraiserOf those 120 opportunities, about 70 percent sit in the pre-handraiser stage, where reps are still working to connect with people.The remaining 30 percent sit in the post-handraiser stage, where there's already an active, ongoing conversation with the customer.That split keeps reps focused on outreach without starving the deals that are already moving.Marketing and Sales Load the Pipeline TogetherPieter is careful to point out that loading the pipeline isn't a sales-only effort. It's a collaboration between sales leadership and marketing leadership.Marketing helps identify and prioritize which accounts and departments actually fit where Tax Guard's solution applies.That partnership is part of why the team can hand reps a healthier mix of fast cycle and slow cycle opportunities instead of leaving it to chance.Why They Kept AEs on the Full Buyer Journey Instead of Handing Off to BDRsBecause their solution requires ongoing education, Pieter's team decided against using BDRs or SDRs to book appointments and hand off to AEs.The same person a buyer starts talking to needs to stay with them as a trusted advisor through the entire education process.Pieter is clear that this only makes sense because of how complex and unfamiliar their solution is. A more transactional sale can absolutely work with a BDR handoff.The Cadence: 17 Touches Over 70 DaysEach opportunity in the pipeline follows a defined cadence, roughly 17 touches over 70 days, with three to five contacts tied to each account.That structure turns follow-up into a math exercise. Once you know the number of opportunities, steps, and contacts, you know almost exactly how many activities a rep needs to complete each day.The cadence isn't automated. Reps still show up and do the work themselves, which keeps the process personal instead of robotic.Personalization Is What Makes the Math WorkPieter gets five to six hundred pitches a day himself, so he knows exactly what gets ignored: generic, unpersonalized outreach.His team uses AI to gather background information quickly, but the personal touch, referencing where someone went to school or what they care about, still has to come from the rep.That combination of structure and personalization is what actually breaks through the noise instead of just adding to it.How They Catch Reps Who Are Gaming Activity NumbersTo catch reps who rack up huge activity numbers without real substance, like hanging up before voicemail or blasting the same email to everyone, Pieter's team looks past raw activity totals.They review call recordings and email engagement to see whether real conversations are actually happening, not just whether the activity got logged.The goal isn't to catch people doing something wrong. It's to find the reps who are getting real engagement and figure out what they're doing differently so the whole team can replicate it.Weekly and Monthly Rhythms Keep the Team AccountableEvery rep gets a weekly one on one that covers both big strategic issues, like what's happening in the market or with competitors, and specific opportunities that need a plan to close.Once a month, Pieter's team reviews the front end metrics as a group: how many people are in cadence, how many emails are opening, how many real conversations are happening.They also track Net Promoter Score to measure how the sales experience actually felt to the buyer, not just whether a deal closed.Their Tech Stack: Salesforce, Gong, Gong Flows, and DelightedSalesforce is their core CRM, and Pieter says most of what makes it powerful is what gets plugged into it.Gong records and analyzes sales conversations, which lets the team track things like how often pricing objections come up and coach reps faster than they could otherwise.Gong Flows adds structured outreach sequences with AI built in, and Delighted measures NPS so the team can see how the buying experience felt from the customer's side.The Numbers Pieter's Team Watches Every WeekClose rate and pipeline velocity are the two headline numbers Pieter checks first, since they show whether the whole system is working.Underneath those, his team tracks how long deals sit in each of their seven pipeline stages, with alerts when something sits too long.They also watch the quality of the opportunities reps are given and how well each rep prospects into the right people, since strong activity numbers mean nothing if they aren't pointed at the right accounts."Activities create opportunities, opportunities create sales. The only thing we control is our activity level." — Pieter LeenhoutsResourcesConnect with Pieter Leenhouts on LinkedIn.Learn more about Tax Guard, a Cogency Global company.Keep track of your sales activity and boost your results with the Prospect Pro sales tool.Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.Visit Blue Mango Studios for help creating podcast production content.Join our LinkedIn cohort and learn to prospect the right way.Sponsorship OffersThis 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.CreditsAs 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, <a...

Connie Kadansky was a highly motivated, highly goal-oriented salesperson, and she was still taking naps at two in the afternoon instead of prospecting.That contradiction sent her down a research rabbit hole that turned into a 29-year career studying sales call reluctance. Connie broke down for me why being too nice is one of the most expensive habits a seller can have, and what to do about it instead.The Napping Salesperson Who Became a Call Reluctance ExpertYears ago, Connie was a highly motivated, highly goal-oriented seller who kept finding herself taking naps at two in the afternoon instead of prospecting.That contradiction led her to a book called The Psychology of Sales Call Reluctance, written by two behavioral scientists, and eventually to their fear-free prospecting workshop and eight weeks of coaching.She's been a licensee with that research organization for 29 years, and still uses the same assessment to diagnose call reluctance in sellers today.Being Too Nice Is a Real, Named Problem: The YielderConnie's research identifies 16 types of sales call reluctance, and the most costly one is called the yielder.Yielders are great with people. They can open a conversation and build rapport easily, but they struggle to move a conversation past that rapport into the next real step.The belief driving it: the nicer I am, the more they'll like me, and the more likely they are to buy. Connie is direct that this isn't true, and it leads yielders to back off and hope the prospect closes the deal for them.The Three Types of Yes You'll Hear in a Sales ConversationA committed yes means the prospect is genuinely engaged and agreeing to a real next step.A counterfeit yes sounds positive but has nothing behind it, things like "send over some information" or "call me in two months."A confirmation yes happens when a prospect confirms something concrete, like who else is involved in the decision. Yielders are the most likely to accept counterfeit yeses at face value and build their forecast on them.Nice Versus Kind Aren't the Same ThingConnie draws a clear line: nice is agreeable and comfortable. Kind is asking a question the prospect has never considered, and actually working to solve their problem.Her definition of selling is solving people's problems for a profit, and staying kind means keeping the conversation pointed at the actual problem instead of just keeping things pleasant.If there's no real problem to solve, no amount of niceness changes that. The relationship alone was never going to be what closed the deal.Stop Overinvesting in RapportSpending too much time on small talk, weather, sports, general connection, feels productive to a yielder, but it isn't what closes business.Connie points out that most people don't buy because a rep shares their taste in baseball. They buy because the rep solved a real business problem.Her fix: be friendly, be kind, but get to the point quickly, and have real, prepared questions ready to move the conversation rather than lingering in rapport building.Understand the Objection, Don't Just Try to Overcome ItConnie's approach breaks from the standard sales training instinct to power through and overcome objections. Instead, she teaches getting curious about the objection itself.Yielders tend to treat objections as conflict, and conflict is exactly what they're trying to avoid, so they steer around it instead of naming it directly.Her technique borrows from Chris Voss's negotiation work: label the emotional component behind the objection out loud, which takes practice but opens up a much deeper conversation.Get Curious to Go Beyond the Surface-Level ProblemIt's easy to stop at a surface-level answer, like a prospect saying they need a new CRM, and move straight to a quote without digging further.Connie recommends calibrated what and how questions, prepared in advance, to get past the surface answer to what's actually driving the frustration.Her rule of thumb: curiosity isn't intellectual, it's emotional. The best sellers can set aside their own agenda long enough to keep asking, sometimes with something as simple as "what else?"How to Actually Fix This in YourselfConnie's advice starts with getting genuinely curious as a practice, not just a technique, including reading about curiosity and noticing how much more interesting curious people's lives tend to be.She recommends writing the actual inner dialogue down on paper: naming the specific fears behind the hesitation, like fear of pushback on price or fear of a difficult implementation.The goal isn't to lose the warmth that makes yielders likable. It's pointing that same personality at pulling out the truth instead of avoiding it."My definition for selling is solving people's problem for a profit." — Connie KadanskyResourcesConnect with Connie Kadansky on LinkedIn. She publishes an article on sales call reluctance about once a week.Visit Connie's company, Exceptional Sales Performance, to learn more about her coaching and the SPQ assessment.Join our LinkedIn cohort and learn to prospect the right way.Visit Blue Mango Studios for help creating podcast production content.Sponsorship OffersThis 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.CreditsAs 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.

An architect plans every brick before laying one. An archaeologist starts digging and adjusts based on what turns up. Adam Mark Louther says most sales reps try to sell like architects when the job actually calls for an archaeologist's mindset.Adam built his first sales skills knocking on doors selling exterior cleaning services, and today he coaches founders and sales teams on turning conversations into paying clients.We talked about why overthinking kills deals, how the first five minutes of a call sets the frame for everything after, and the two-call process he uses to close more business.Stop Overthinking and Take ActionAdam's biggest message: sales gets overcomplicated. Most people already have enough information to move, but they stall out gathering more instead of acting on what they have.People stuck in analysis paralysis are the ones who need every detail mapped out before they'll take a single step, and that costs them in a fast moving environment like sales.The reps and leaders who win aren't the ones with the perfect plan. They're the ones who execute, look at the results, and adjust from there.Think Like an Archaeologist, Not an ArchitectAdam's framework, borrowed from his mentor: an architect needs total certainty before building, since every measurement has to be right before anything gets built.An archaeologist works the opposite way. They dig in one spot, see what's there, and adjust based on what they find, since nobody knows exactly what's underground until they start.Sales works like archaeology, not architecture. You have a general idea of where to focus, then you test, learn, and adjust instead of waiting for certainty that never comes.There's No One Right Sales ProcessAdam pushes back on the idea that there's a single correct sales methodology to follow, whether that's MEDDIC, Challenger, or anything else.What matters is consistently doing the fundamentals: finding the real issue, talking to the right person, and building enough value that price stops being the objection.Getting stuck choosing the "perfect" framework is its own form of analysis paralysis, and it keeps people from ever getting real reps in.The First Five Minutes Sets the FrameA call handled poorly in the first few minutes can cost the entire sale, because that's when the frame and the agenda get set.Whoever asks the questions controls the call. Without setting that frame early, a buyer with a strong personality will take over the conversation entirely.Adam learned this the hard way early in his career, watching experienced buyers steer his calls before he had a structure in place to prevent it.Three Parts of Opening a Call: Icebreaker, Frame, AgendaThe icebreaker is genuine, unscripted small talk. It should feel like a normal conversation, not a routine, and it should be dropped if the other person clearly isn't in the mood for it.The frame reminds the buyer why the call is happening and how they got connected in the first place, since a call booked weeks ago often gets attended on autopilot without that context.The agenda tells the buyer exactly how the call will run, before a single discovery question gets asked. Adam explicitly tells prospects he'll ask questions first, then invite them to a second call if it's a genuine fit.Always Book the Next Meeting From the MeetingAdam uses what he calls BAMFAM, book a meeting from a meeting. If a prospect says they'll "arrange something" later, that call almost never happens.The second call needs to get booked on the calendar before the first call ends, since people get busy and forget otherwise.This is a small habit that protects momentum on every deal in the pipeline.Build a Personalized Game Plan Before the Second CallBetween the two calls, Adam reviews the discovery call transcript and notes, then builds a plan using the prospect's own language and specific pain points.On the second call, he walks through that plan, framed as free coaching rather than a pitch, which is what makes prospects want to see more detail instead of feeling pitched to.The transition into the actual offer is simple: he tells them the plan isn't quite as simple as the summary, offers to show them more detail if they want it, and lets the prospect self-select into hearing the pitch.How to Actually Start Taking ActionAdam's advice for anyone stuck in analysis paralysis: first figure out what's actually driving the hesitation, whether it's fear of rejection or something else, since you can't fix what you haven't named.After that, find the smallest possible action you can take today, not the biggest.Small wins build confidence, and that confidence compounds until the actions that felt out of reach start to feel normal."Think about what is the smallest action you can take today. Gain confidence from every action you take, and it compounds." — Adam Mark LoutherResourcesConnect with Adam on Instagram: @adammarklouther. He offers a free 45-minute discovery call to talk through where your sales process may be losing deals.Join our LinkedIn cohort and learn to prospect the right way.Visit Blue Mango Studios for help creating podcast production content.Sponsorship OffersThis 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.CreditsAs 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.

Your prospect isn't only buying the product or the price. They're buying you. That's the idea behind one of Jordan Harbinger's most popular keynotes, and it's why we're pulling this archive conversation back out.Jordan went from a bored kid who got into trouble to a Wall Street attorney to the host of one of the biggest interview podcasts around. And the thread running through all of it is relationships. The principles here haven't aged a bit. This episode explores all of it.Why Jordan Started Studying This in the First PlaceJordan assumed people with strong networks were either born into them or got there through some elite club or school connection.That changed on Wall Street, when he realized everyone around him was just as smart and just as hardworking. Being the smartest or the hardest worker in the room was no longer a real advantage.A partner at his firm who was rarely in the office turned out to be out generating business through relationships, not hiding from work. That single conversation changed how Jordan thought about his entire career.Relationships Are the Foundation, Not the Finishing TouchJordan compares skipping networking to building a house without a foundation. You don't add the roof and windows first and figure out the foundation later. It doesn't work that way with a business or a career either.The most common mistake people make is pushing networking to later. Entrepreneurs tell themselves they'll focus on relationships once the website, the product, and the ads are all dialed in first.By the time most people realize they skipped it, it's already cost them. Jordan points to the classic moment of watching someone else get promoted to become your boss, when the real difference often wasn't skill. It was who built relationships along the way.Skip Networking Events That Aren't CuratedJordan's rule: avoid any networking event open to the general public. If anyone can walk in, there's a strong chance the room is full of people looking to take, not give.He describes his own experience at open mixers: a rotating cast of financial planners, car salesmen, and life coaches all working the room for a stale cookie and a captive audience.A curated event, like a real chamber of commerce meeting full of actual business owners, is worth your time. If you can't get invited to one, Jordan's advice is simple: build your own.Why Giving First Actually Scales Better Than ClosingJordan contrasts the old "always be closing" mindset with what he calls ABG, always be giving. Closing limits you to the handful of people in a room who happen to need exactly what you sell.Giving opens up nearly everyone in the room, because you're looking for what they need instead of trying to match them to your offer.Jordan's example: instead of pitching graphic design services to someone who doesn't need them, he'd ask what they're working on, then connect them to someone in his network who can genuinely help. That's scalable in a way that chasing a single sale never is.Don't Keep ScoreGiving only works if it's not secretly transactional. Jordan warns against what he calls keeping score: doing favors while quietly expecting something back later.He illustrates this with a story about a friend who drove a neighbor to the airport repeatedly, expecting it to eventually turn into a relationship, then got upset when it didn't. The resentment showed up in every interaction afterward, and the other person had no idea why.The same pattern shows up constantly in sales. A rep gives a free tip, then pitches the very next interaction. That turns a relationship into a quid pro quo, and people can feel it immediately.Dig the Well Before You're ThirstyJordan's core advice: build relationships long before you need them. Waiting until you need a job or a referral to start networking is like keeping a spare tire in the trunk and only thinking about it after you're already stuck on the highway.His practical exercise: write down the ten people you'd call if you lost your job tomorrow, then reach out to them this week, while you don't need anything from them.That single habit, reaching out with nothing to ask for, is what separates people with a real network from people scrambling to build one under pressure."You have to give first, not just because it's a great Zig Ziglar quote or a Brian Tracy principle. It's because it's logistically easier for me to find a need that you have than it is to match a need you have with a service that I provide." — Jordan HarbingerResourcesListen to The Jordan Harbinger Show, wherever you get your podcasts, or visit JordanHarbinger.com.Check out 6 Minute Networking, Jordan's free course on building real relationships.Join our LinkedIn cohort and learn to prospect the right way.Visit Blue Mango Studios for help creating podcast production content.Sponsorship OffersThis episode is brought to you in part by HubSpot.You don't become the world's most valuable women's sports franchise by accident. Angel City Football Club did it with a little help from HubSpot, unifying their website, email, and fan experience in one platform, and growing their database 300 percent in two years. Visit hubspot.com to hear how HubSpot can help your team grow better.This episode is brought to you in part by LinkedIn.LinkedIn Sales Navigator uses AI-powered recommendations and real-time account insight to help you spend less time searching and more time selling, all powered by LinkedIn's network of over 1.2 billion professionals. Try it free for 60 days at linkedin.com/sell.This episode is brought to you in part by Blue Mango Studios.Imagine using a podcast as a lead generation source, attracting your ideal customer while getting qualified leads. Find out more at bluemangostudios.com.CreditsThe Sales Evangelist Podcast is created by the Sales Evangelist Sales Training Organization. It is produced by TSE Studios. Our podcast production manager is Nancy Paul. Our audio engineer is Jerchin Obyale. Our video engineer is Dasan Kunado. Guest management is done by Jill Vito and Christy Vertus. Our content writer is Carlisa Galbreath. Our graphic designer is Urvish Savalia, and Donald C. Kelly is your host and executive producer.