Episodi

  • How to Know if Your Deal is Going South Sooner than Later | Andee Harris - 2036

    How to Know if Your Deal is Going South Sooner than Later | Andee Harris - 2036
    Sep 11 2026
    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.
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    29 min
  • Your Connection Rate Dropped 80% and Nobody's Talking About It | David Zeff - 2037

    Your Connection Rate Dropped 80% and Nobody's Talking About It | David Zeff - 2037
    Sep 14 2026
    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...
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    36 min
  • AI Didn't Kill Sales Strategy. It Exposed Who Never Had One | John Stopper - 2038

    AI Didn't Kill Sales Strategy. It Exposed Who Never Had One | John Stopper - 2038
    Sep 18 2026
    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 ...
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    34 min
  • How to Future Proof Against Getting Ghosted | Donald C. Kelly - 2041

    How to Future Proof Against Getting Ghosted | Donald C. Kelly - 2041
    Sep 28 2026

    Nearly half of all B2B sales conversations end with no decision at all, and that number keeps climbing. This solo episode breaks down the discovery call framework built over years of carrying a bag as a software sales rep, now taught to clients to stop deals from going quiet.

    The Real Cost of No Decision

    • A study of 2.5 million sales conversations by Matthew Dixon and Ted McKenna found that 40 to 60 percent of B2B deals end in no decision, not a loss to a competitor, just silence.
    • Of those no-decision deals, 44 percent come from the prospect of sticking with their status quo, while the other 56 percent come down to indecision and analysis paralysis.

    Step 1: Build Rapport With Something That Matters to Them

    • Small talk gets replaced with something specific and current about the prospect's business, like a recent win or a stat about their market share, so the conversation centers on them, not the seller.
    • This shows the prospect that homework was done before the call, and it gets them talking about something they're proud of right from the start.

    Step 2: Set the Rules Before You Play the Game

    • Early in the call, the prospect hears that the last five minutes are set aside to make a decision together, whether that's moving forward or agreeing it's not a fit.
    • The prospect also gets permission to end the call early if it's clear they're not a match, which takes off the pressure and builds trust instead of suspicion.

    Step 3: Run Discovery So They Talk More Than You Do

    • Before anything gets demoed, the prospect is asked what they want to learn from the call, then asked what else, so the exact proof they need becomes clear.
    • Data from Gong backs this up: sellers should talk 30 to 40 percent of the time while buyers talk 60 to 70 percent, and that ratio is what keeps a deal moving instead of stalling.

    Step 4: Use the Last Five Minutes to Get a Real Decision

    • Every call closes with a menu of next steps for the prospect, like bringing in a technical stakeholder, so there's a clear path forward instead of a vague "let me think about it."
    • Getting the prospect's direct cell number and permission to text also gets added in, which makes it much harder for a deal to quietly disappear.

    "Set the rules before you play the game." — Donald C. Kelly

    Resources

    • Learn more about the research behind this episode: jolteffect.com

    Sponsorship Offers

    1. 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.

    1. 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.

    1. 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.
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    24 min
  • How I Handle Every Price Objection | Donald C. Kelly - 2042

    How I Handle Every Price Objection | Donald C. Kelly - 2042
    Oct 2 2026
    “It’s too expensive” may be the answer a prospect gives you, but it may not be the reason they are saying no.The real issue could be that they do not see the value, they already have another solution, or they have another concern they have not told you yet.In this objection-handling conversation, I break down two ways to get past the surface response, find the real reason behind an objection, and connect your solution to what the prospect actually values.The Real Reason Behind a Price ObjectionA prospect who says a $100 water bottle is too expensive may not really have a problem with the $100. They may simply be comparing it to a $10 bottle and not seeing what makes the more expensive option worth it.The value changes based on the buyer. For someone working outside in South Florida, a bottle that keeps water cold all day, has a built-in filter, and reduces trips away from a job site can solve problems that a cheaper bottle does not.That is why dropping the price is not always the answer. If the prospect does not see the value at $100, they may still not see it at a lower price.The salesperson's job is to find out what matters to that specific buyer and connect the solution to that need.Use the Socratic Method to Get to the Root IssueThe Socratic method uses questions to help prospects think through their own problems and understand why a solution may be in their best interest.The questions should not be random. They should focus on the prospect's challenge and help uncover what is behind the first objection.A prospect may start with “I can get a water bottle for $10.” Keep asking questions and you may discover that the cheaper bottle means buying more water, buying ice, leaving the job site, and losing time that could have been spent quoting more work.Thank the Prospect Before You Challenge the ObjectionThe first step is to thank the prospect for raising the concern and show genuine empathy. A $100 purchase is a bigger decision than a $10 water bottle, so the concern deserves to be taken seriously.From there, ask what they mean when they say it is expensive. Are they comparing it with another product? Have they never paid that much for a water bottle? Or do they simply believe the product is not worth $100?Those questions help reveal what the prospect is really thinking instead of forcing the salesperson to guess.Once the real concern is clear, the salesperson can educate the prospect around the value they were not seeing.Turn Lost Time Into a Business CaseThe water bottle example becomes more valuable when the conversation moves from the product itself to the time it can save. A construction worker who has to leave a job site for water or ice is losing working time.If that person can get even 30 minutes back in the day, that time could be used to quote more jobs. When one new job is worth thousands of dollars, the value of the solution looks very different.The salesperson is no longer selling a water bottle. They are selling convenience, time, and the chance to create more revenue.The same principle applies to other products and services: find the business problem behind the feature and show the prospect what solving it is worth.The Menu Method Gives You a ShortcutThe second approach is the Menu method. Instead of asking a long series of questions, give the prospect a few common reasons other buyers have raised the same objection and ask if one applies to them.The options should come from real sales conversations. For example, the prospect may think the product is too expensive because it will not last, because they already have another solution, or because they are not interested in working with the company.This gives the prospect an easier way to explain what is really stopping them without having to come up with the answer from scratch.If none of the options apply, that is useful too. Ask them to explain what the real issue is and keep digging.Make the Prospect Empty Out Every ObjectionA prospect may have more than one concern. They might start with price and then reveal that they also think the product is fragile.That is why asking, “Is there anything else?” matters before moving into the solution. The goal is to get every concern on the table.Once the prospect has explained everything, you can address each issue instead of solving one objection and discovering another later.The approach is simple: find the root cause, explain how your solution addresses it, and then give the prospect a clear reason to believe the result is possible.Use Proof Before You Ask for the SaleAfter uncovering the objection, the next step is to educate the prospect and use a testimonial or case study from someone with a similar problem.One example in the conversation involves a company that bought the bottles for its team because employees were leaving job sites to get water. Those trips were linked to accidents, lost time, and other problems.The company saw roughly $300,000 in value from keeping its team on...
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    24 min
  • How to Reach Decision-Makers When Selling to Enterprises | Erik Kostelnik - 2043

    How to Reach Decision-Makers When Selling to Enterprises | Erik Kostelnik - 2043
    Oct 5 2026
    125 billion B2B emails go out every single day, and that number is exactly why decision-makers have stopped noticing any of them. This one is coming from the archives, and honestly it feels even more relevant now than when it first aired, because reaching the right person inside an enterprise has only gotten harder since. Erik Kostelnik, founder and CEO of Postal, joined me to break down why reaching enterprise buyers has gotten so much harder and exactly what sales reps need to do differently to cut through that noise.Why Decision-Makers Have Gone Numb to OutreachThe real problem isn't that buyers are unreachable, it's that everyone selling to them is running the exact same automated plays, the same email sequences, the same LinkedIn messages, and the same call cadences.With roughly 125 billion B2B emails sent daily, that volume has hit a critical mass where prospects develop a visceral reaction to anything that looks like a template, so the content itself stops mattering.Even internal teams at the companies you're targeting are often running similar outreach sequences to their own prospects, which means the people you're emailing recognize the exact playbook you're using.Touches Have Doubled, and So Has the TimelineThe old rule of five touches over 30 days to get a yes or no has shifted, and the better target now is closer to 10 touches spread across 60 days.That shift ties directly to buyer behavior during 2020, when prospects were slower to respond and more hesitant to commit, which stretched out both the number of attempts needed and the overall timeline.Reps need to stop treating the five-touch, 30-day sequence as a fixed rule and instead build in enough room for buyers who need more time and more contact before they'll engage.Personalization Beats Automation at ScaleThe fix is to throw out the generic, templated sequence and go back to persona-based selling, meaning reps need to understand what a specific buyer actually cares about before reaching out.Postal's own approach treats direct mail and gifting as a real part of the sequence now, not an afterthought, because a handwritten note or a physical touchpoint still converts at a noticeably higher rate than another email.The goal is to automate the offline channel the same way sales teams already automate email, so a gift, a direct mail piece, a LinkedIn touch, and a phone call all carry the same consistent message instead of feeling disconnected.What a Real Outreach Sequence Looks LikeFor C-level targets, a strong sequence opens with a gift email, something like offering a relevant book with a short personal note, sent as part of a tracked outreach flow.If the prospect doesn't accept that first gift, the sequence continues with a LinkedIn touch, a phone call, and a follow-up email, then repeats with a different offer, like a direct mail brochure, if the second attempt also goes unanswered.This entire offline sequence runs in parallel with manual, non-automated emails and genuine engagement with the buyer's social content, and teams that combine offline and online touches see at least double the engagement.Why the Funnel Itself Needs to Flex Right NowBreak the funnel into three parts, top, middle, and bottom, and diagnose which part is actually slowing deals down before trying to fix the whole process at once.At the top of the funnel, differentiation is what speeds things up, since standing out from competitors running the same automated plays is what gets a reply in the first place.In the middle of the funnel, flexibility matters most, which is why Postal leans into free trials even though a 12-month agreement is the ideal outcome, because buyers need an easier way to say yes during an uncertain stretch."If you're not getting the right results, try something different." — Erik KostelnikResourcesConnect with Erik on LinkedIn.Learn more about Postal, the gifting and offline engagement platform.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.
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    30 min
  • 4 Steps to Systematic Sales Growth | Jimmy Burgess - 2045

    4 Steps to Systematic Sales Growth | Jimmy Burgess - 2045
    Oct 12 2026
    "Broke, rich." That's the two-word test Jimmy Burgess uses to explain whether a sales career is working: phone up to your ear, you're rich; phone down, you're broke.Pulled from our archive, Jimmy, Chief Growth Officer at Berkshire Hathaway HomeServices Beach Properties of Florida, is with me as we discuss the four-step pattern he lays out for turning scattered activity into steady, repeatable growth that hasn't aged a day.Growth Follows a Pattern, and It Starts With ConfidenceSystematic growth runs through four connected stages: competence builds confidence, confidence leads to consistent repetition, repetition builds a reputation that earns more opportunities, and those opportunities turn into conversations that convert.Skipping any one of those stages, or doing them inconsistently, is why so many reps feel like they're working hard without seeing the compounding results they're after.The whole cycle starts with the individual seller, not the market or the lead source, because confidence is what makes every later stage possible.Step One: Always Be Learning, Not Always Be ClosingThe old "always be closing" mindset gets replaced with "always be learning," meaning the real advantage comes from becoming the most knowledgeable person in your field, not the most aggressive closer.Confidence works like walking into a dark room versus a lit one: uncertainty about your product or market makes you move cautiously, while real expertise lets you walk in boldly and handle whatever comes up.There's no excuse for staying stuck on a weak spot right now, since free training on virtually any topic is one search away, and the only real barrier is the discipline to keep learning instead of getting comfortable.Step Two: Repetition Builds ReputationConsistent, visible value, like a weekly video update or a regular check-in, is what builds a buyer's trust before they've ever had a real conversation with you.One real story drove this home: a stranger at a local event recognized a familiar face from a weekly video list, introduced himself, and said, "I'm on your mailing list, you're my guy," despite never once responding to an email.The accountability piece matters just as much as the consistency itself; running small weekly groups where people report their leading indicators, like a set number of conversations, keeps that repetition from quietly slipping.Step Three: Conversations Lead to ConversionsSocial posts and videos warm people up, but real trust and real deals still come from an actual conversation, which means picking up the phone remains non-negotiable.A blunt phrase sums it up well: hold an imaginary phone up to your ear and the choice is simple, "phone, rich" or "no phone, broke," because business still happens through direct conversation, not passive content.Confidence built through learning is what makes those calls easier, since a well-prepared rep isn't scrambling for answers mid-call, they're simply having the conversation they already know how to have.Step Four: Raving Fans Become Your Referral EngineMost reps put all their effort into winning the deal and then go quiet right after the transaction closes, which is exactly the moment real referral opportunity gets left on the table.Turning a client into a referral source means doing something genuinely unexpected tied to what matters to them personally, like giving a family's kids a small surprise gift at closing instead of another generic thank-you.A simple follow-up call weeks after the transaction, just checking that everything's still going well, keeps you top of mind and is what actually generates referrals, since referrals come from what happens after the sale, not during it.Growth and Comfort Cannot CoexistA personal story about a 13-year-old finishing third in his first cross-country meet became the closing message: real growth only happens when you choose to run into discomfort instead of away from it.The advice for reps avoiding the phone, avoiding a hard skill, or avoiding an uncomfortable conversation is the same: anyone can push through roughly seven minutes of discomfort, and what's on the other side is usually exactly what they wanted.Staying comfortable isn't neutral, it's actively dangerous for growth, since decline tends to follow closely behind any extended stretch of comfort in a sales career."Growth and comfort cannot coexist." — Jimmy BurgessResourcesConnect with Jimmy Burgess on LinkedIn.Check out The Real Estate Sales Podcast, where industry experts share strategies that apply well beyond real estate.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/...
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    40 min
  • Managing AI Agents Is Just Like Managing A New Employee | Kristie Jones - 2047

    Managing AI Agents Is Just Like Managing A New Employee | Kristie Jones - 2047
    Oct 16 2026
    Kristie Jones treats her AI agent like a four year old. Not as an insult, as a management strategy. The same way she taught her son "no touch" before he understood why, she's learned that agents need boundaries, check-ins, and correction, just like any new hire. Kristie, founder of Sales Acceleration Group and author of the upcoming book The Sales Leadership Gap: Leading Humans in an AI Augmented World, walked me through what it actually looks like to lead a sales team that's now part human, part automation, and part AI agent.Why Most Sales Teams Are Only Talking About AI, Not Using ItKristie's blunt read on the market: sales leaders are talking a good game on AI adoption, but very few are actually walking it.She calls the hesitation "freeze mode," people waiting for the technology to settle down before they commit to anything.Her pushback: the pace of AI isn't going to slow down, so waiting for the dust to settle just means a competitor gets the head start instead.From Pilot to Control Tower: Managing a Hybrid TeamKristie's analogy for what's changed: sales leaders used to be the pilot, flying the plane directly. Now the job is running the control tower.A modern sales team isn't just a group of humans anymore. It's humans, automation, and AI agents all working together, and leading that requires a 360-degree view no single seat inside the plane can give you.She hasn't seen a single sales leadership course that actually teaches this. Most leaders are being asked to figure it out on their own, in real time, while still being expected to hit quota.Treat Your Agent Like a New Employee (or a Four-Year-Old)Kristie's favorite framing, borrowed from someone else: manage your agent the way you'd manage a toddler, with simple, repeated boundaries, like teaching a child "no touch," some for safety and some just to prevent a mess.Building an agent isn't a "set it and forget it" project. Just like a new hire, it needs a handbook, but it also needs regular check-ins, since no handbook covers every exception.If your business is changing, and it always is, an agent that never gets revisited will quietly drift out of step with how your team actually works.Trust But VerifyKristie built an agent that reviews her AI notetaker every Friday at 4pm and delivers her to-do list by day. The first Friday it was supposed to run, it didn't.Her response mirrored exactly how she'd handle a new employee's mistake: no anger, just a direct conversation about what happened and how to prevent it next time.Her rule going forward: trust the agent to do the work, but verify the output regularly, the same discipline she'd apply to any new hire still earning full independence.Where to Start: Update Your Playbook Before You Automate ItKristie pushes back hard on the idea that sales playbooks are dead. They're not, but most of them are badly out of date, built once and handed to new hires without ever being revisited.Her recommended first step for any leader building agents: go back to the actual playbook, confirm it reflects how work really gets done today, then look at it again through a new lens, asking which of these tasks could be automated.Skipping this step means building automation around a process that's already wrong, which just makes the wrong process faster.Two Agents Kristie Actually BuiltHer first agent connects Claude Cowork to HubSpot, Granola (her AI notetaker), and Google. Every Friday at 4pm, it reviews her week's meetings and delivers a day-by-day to-do list of everything she committed to.Her second is a research agent, built to be extensive enough that she now teaches a class on building one at Sales Gravy University.Neither required a dedicated engineering team. She built both herself as a sales leader, which is exactly the point: if your company doesn't have a go-to-market engineer or enablement team, this becomes your job by default.Write a "Role Brief" for Every AgentKristie's upcoming book outlines five leadership competencies and five AI competencies leaders will need, and one of the practical tools she recommends is what she calls a role brief.A role brief is a formal, written document for an agent, similar to a job description but for AI: what decisions it's allowed to make, what decisions always stay human, what the output should look like, and who owns checking it.Every agent a team builds should have one of these, the same way every human hire gets a real job description instead of a vague verbal understanding of the role.The Two Things That Make AI Dangerous If Left UncheckedFirst, AI is built to solve problems, which means if it can't find a real one, it may manufacture one to justify itself.Second, AI essentially never says it doesn't know, and it almost never asks for a leader's opinion. It delivers a confident answer even when the underlying accuracy is shaky.Both are reasons an agent can never be treated as fully autonomous. Someone still has to be checking the actual output, not just assuming the system ...
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    33 min