The Sales Evangelist

Donald C. Kelly
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  • Entrepreneurship
  • Semiweekly

I believe in doing BIG THINGS! You should be earning 6 figures easily as a sales rep. But chances are you are not...yet! Sales is the most important department in every company but many sellers are never taught how to effectively sell, much less how to earn their way to high-income status. My own career limped along until a company I worked for invested in sales training to help me succeed. Immediately afterward, I closed a deal worth 4X what the company spent on me and saw hockey-stick improvement in my performance. So I started a podcast to “Evangelize” what was working. Today I interview the world's best sales experts, successful sellers, sales leaders and entrepreneurs who share their strategies to succeed in sales right now: folks like Jeffrey Gitomer, Jill Konrath, Bob Burg, and Guy Kawasaki to name a few. They share actionable insights and stories that will encourage, challenge, and motivate you to hustle your way to top income status. If you’re someone looking to take off in your sales career and earn the income you deserve, hit subscribe and let’s start doing BIG THINGS!

  1. 2d ago

    How to Mentally Prepare for a Successful Discovery Call

    Ep 2051 | Isaac Ho - How to Mentally Prepare for a Successful Discovery Call A therapist-turned-sales-coach walks me through a live, unscripted discovery call role play, and it exposes exactly where most reps go wrong before a single question gets asked. Isaac Ho, who coaches entrepreneurs on the mindset side of high-ticket sales, breaks down what's actually happening in your head before a call and why that matters more than any script. This one has been sitting in the back catalog for a while, and it earns another run because the mindset problems it covers never really go out of style. Your Beliefs Shape What Happens on the Call A buyer isn't reacting to your price as much as he's reacting to the belief you're carrying into the room about your price.A $20,000 piece of gym equipment got sold at a steep discount, not because the buyer pushed back on cost, but because the rep expected a money objection and started slashing the price before anyone asked.That pattern shows up constantly. Whatever belief a rep walks in with about how the call is going to go tends to shape the prospect's actual response to it. Discovery Calls Run on Energy, Not Just Questions Sales is a transfer of energy, and a prospect is reading that energy within the first few minutes of a call, often before a single real question gets asked.Showing up unprepared, distracted, or carrying frustration from somewhere else in life changes your tonality enough for a prospect to feel it and start to disconnect.Dealing with whatever you're carrying into the call before you dial in isn't optional self-care, it's a direct part of doing right by the person on the other end. Preparation Changes How You Show Up in the Room Walking into a call with zero research puts you in a subservient position, fishing for basic information instead of leading a real conversation.A little homework ahead of the call changes both the questions you ask and the way you carry yourself, because you show up believing you belong at the table.It isn't your job to explain your own business model to a prospect who hasn't bothered to look into it. That's homework they should have done before the call, not during it. Curiosity Beats a Preconceived Solution Assuming you already know the problem, like assuming every web services inquiry is really about wanting a new website, skips the real conversation and sells a fix to the wrong issue.A prospect's stated want and their actual problem are often two different things, and only real curiosity closes that gap.The goal of a discovery call is helping someone see their problem differently, because thinking about it the same old way just keeps them stuck in it. The Live Role Play, Broken Down In the role play, a simple opening question, what made you want to set up this call, immediately handed control of the conversation to the prospect instead of the rep.Each follow-up question dug one layer deeper into the actual cost of the problem, from missed family dinners to lost revenue, instead of settling for the first surface-level answer.Asking why you think you're creating that problem lets the prospect arrive at his own insight, which lands far harder than being told the answer outright. Three Things to Clear Before You Dial In Get honest about whether a yes or no answer feels like it's about your own worth. If it does, you'll start treating objections like personal arguments instead of normal parts of a sales conversation.Accept in advance that not everyone will move, even when you handle the call perfectly, because some people see the problem clearly and still choose to stay stuck in it.Know your own shadow and trigger patterns, since suppressed feelings and undealt reactions tend to surface right when a prospect brings up money. "Sales is just a transfer of energy." — Isaac Ho Leadership Advice, Books, and Quotes The core idea behind this episode is that a discovery call is decided before it starts, by whatever belief, energy, and baggage a rep brings into it. Clear your head, set a real intention to understand instead of to sell, and let the prospect arrive at their own answer instead of handing it to them. That shift alone changes how people respond to you on a call. Resources Connect with Isaac Ho on LinkedIn and let him know you heard him on this episode. Tell me what you thought of this role play on LinkedIn. Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

    How to Mentally Prepare for a Successful Discovery Call

  2. 5d ago

    How Do I Get Enterprise Buyers to Watch My Videos?

    Your video outreach can look great and still get ignored by the exact executives you're trying to reach. This one is pulled from the archive, and it earned that spot because the problem it solves hasn't gone anywhere. Tyler Lessard, VP of Marketing and Chief Video Strategist at Vidyard and co-author of The Visual Sale, joined me to break down what actually gets enterprise buyers to open, watch, and reply to a prospecting video. Rethink What Actually Counts as a Video A lot of people still picture video as a polished, one-to-many production with drone footage and professional editing, and that assumption alone keeps plenty of reps from ever hitting record.A simple webcam recording or quick screen share works fine, because the goal is communicating an idea clearly, not producing something that looks like a commercial.The real shift is seeing video as a faster, more effective way to answer a question or explain something, not as a special project that needs a production budget. Treat Video as Part of the Rhythm, Not a Silver Bullet Sending ten prospecting videos and expecting five replies sets the video up to fail. It's one piece of an outreach sequence, not a standalone bet that has to prove itself in isolation.Video doesn't replace phone calls, social touches, or written emails; it adds a layer of familiarity that makes the rest of that sequence land better.Once a video sits inside the regular rhythm instead of being judged on its own, the fear of it "not working" stops being a reason to skip it altogether. Write a Subject Line That Creates Curiosity A subject line like "Donald, a quick video for you" works because it creates a curiosity gap, and the brain doesn't sit well with an unanswered question without clicking to resolve it.Naming the word "video" directly in the subject line raises open rates on its own, since it stands out against a sea of plain, text-only subject lines.This curiosity effect holds across seniority levels, from an entry-level buyer to a C-suite executive, because it taps into basic human psychology rather than a specific title. End With a Low-Lift Call to Action Asking for thirty minutes of someone's time on a first video is the same awkward ask reps already overuse in cold emails, and it falls just as flat on video.Offering to send a second, slightly more detailed video is a much easier yes, since anyone who already watched the first one has shown they're open to watching another.A low-lift CTA like that opens the door to more face time with a prospect without asking for a meeting before any real trust has been built. Make the Visual Do the Talking Recording with a prospect's own LinkedIn profile visible on screen behind you turns the video thumbnail into something personal enough to earn a click on sight.One memorable example involved a rep showing his own search results next to a competitor's ad, with five-star reviews stacked underneath it, proving a point visually instead of describing it in a sentence.Showing something instead of explaining it saves the viewer the work of looking it up themselves, and that shortcut builds trust faster than a written pitch ever could. Use Video Beyond the First Cold Outreach A short video attached to a meeting reminder lift shows rates, because it puts a real, energetic person in front of the invite instead of another plain calendar notification.A quick recap video after a meeting can travel further than expected. If a champion forwards it internally, it introduces you to decision-makers who were never on the original call.Recording a short answer to a question you get often, once, and reusing it saves real time on every future deal that runs into the same question. "It's about connection, not perfection." — Tyler Lessard Leadership Advice, Books, and Quotes Tyler's core message throughout this episode is that video works because it's human, not because it's polished. Every tactic here, the subject line, the low-lift CTA, the visual proof on screen, is really just a way of making a message feel like it came from a real person rather than a template. His book, The Visual Sale, co-written with Marcus Sheridan, goes deeper into how to build that kind of visual communication into a full marketing and sales process. Resources Connect with Tyler Lessard on LinkedIn to ask about video strategy for your own enterprise outreach. Check out Vidyard for video tools built for sales and marketing teams. Pick up The Visual Sale by Tyler Lessard and Marcus Sheridan for the full framework. Tell me how you're using video in your outreach on LinkedIn. Connect with Tyler on LinkedIn Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

    How Do I Get Enterprise Buyers to Watch My Videos?

  3. Oct 26

    The Last 45 Days: How to Close Q4 Without Discounting

    You’re behind on quota with a handful of weeks left in the year, and the easiest lever sitting in front of you is a discount. In this solo episode, I explain why that lever almost always costs more than it saves, and what I’m telling my own team to do instead in these last 45 days. Why Discounting Costs More Than the Discount Itself A 10% discount on a 40% gross margin sale cuts your profit per deal from $40 to $30, which means you need roughly a third more volume just to land where you started.Discounting at the finish line also raises an uncomfortable question for the buyer. It makes them wonder whether your original price was ever honest in the first place.A discount this year trains buyers to expect one next year too, which quietly resets their anchor price and makes full-price selling harder every quarter after this one. Clean Up Your Pipeline Before You Chase It A pipeline full of stale or unqualified deals makes your numbers look worse than they are and makes it impossible to plan your last 45 days with any accuracy.When a deal slips one to four weeks past its original close date, win rate falls by 34%, and once it slips more than a month, win rate drops even further.A deal that's slipped that far is close to unrecoverable in-quarter, so it belongs on next year's list, not on this week's call sheet. What to Actually Check in Every Deal Confirm there's a real compelling event driving urgency, since no amount of pressure from your side manufactures one that doesn't already exist.Identify every decision maker in the deal and make sure you have direct communication with each one, not just your single point of contact.Verify the budget is actually there right now, because a great champion with no funding isn't a Q4 deal, it's a Q1 conversation at best. Split Your Time 60/70 on What's Closing Now Spend roughly 60 to 70% of your remaining time on deals that are genuinely capable of closing this quarter, not the ones that merely feel close.The other 30 to 40% still goes toward building next year's pipeline, since Q1 shouldn't start from zero just because Q4 got intense.This isn't about abandoning anyone. It's about being honest with yourself about which deals have a real shot before the calendar runs out. Use the Buyer's Calendar, Not Just Your Own Many buyers are working with a use-it-or-lose-it budget tied to the calendar year, and that pressure can work in your favor if you ask about it directly.If a buyer can't commit to the full scope right now, structure a smaller entry now with room to expand next year, rather than letting the whole deal slide to January.Decision makers often disappear for the second half of December, so lock in their time now instead of trying to chase a signature while they're on vacation. Build a Mutual Action Plan A mutual action plan built backward from the close date keeps both sides aligned on exactly what has to happen and by when.Without one, the buyer doesn't know what's expected of them, and you're left guessing at where the deal actually stands.This document doesn't have to be complicated. A clear list of steps and owners, shared early, does most of the work on its own. This Week's Action Audit your full pipeline first. Confirm decision makers, budget, and a real compelling event exist on every deal still on your list.Pick your top five deals and build a mutual action plan for each one, using a tool like Claude, ChatGPT, or Gemini to draft it quickly.Send that plan to each buyer this week, or set up a call to walk through it together, so everything is in motion well before the year runs out. "The end of the quarter scramble costs more deals than it closes." — Donald C. Kelly Leadership Advice, Books, and Quotes The core principle behind this episode is simple. Don't let the pressure of a deadline push you into a discount that trains your buyers and shrinks your margin. Audit your pipeline honestly, work the buyer's calendar instead of fighting it, and trade for value instead of giving it away. Resources Tell me which of these you're trying this quarter on LinkedIn or Instagram. Learn more at The Sales Evangelist. Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

  4. Oct 23

    4 Ways I’m Using AI in My Sales Process Right Now

    A year ago, I thought AI was mostly a research tool. That assumption didn't age well. In this solo episode, I walk through the four places AI actually earns a spot in my sales process today and where I still insist on doing the work myself. Finding the Right Prospects Without Guessing I use a tool called Zenith to research prospects on LinkedIn through Sales Navigator, pull up what they've recently posted, and queue up a relevant comment or connection request based on that content.A human still has to approve every message before it goes out. I'm not letting this run unsupervised, and I edit plenty of what it drafts before it reaches anyone.This process alone books around three appointments a week for me, and the difference comes from how relevant the outreach is, not just how much of it there is. Building Sharper Prospect Lists With AI Research I connect Claude to data platforms like Apollo and Lusha to build and enrich prospect lists for email campaigns with a level of precision that used to take hours of manual digging.A real example is finding publishers in a specific state who have a set number of books releasing this year and a newly hired director over content. That's the kind of narrow, specific research AI handles well.AI can find better prospects, but it isn't sending the emails or doing the relationship work on its own. The research has to be precise and relevant, and that precision is what actually moves the needle. Meeting Recaps, Follow-Ups, and Prep Emails Fathom joins my calls and takes the notes, then Claude turns those notes into a meeting recap with clear next steps that I can send straight to the prospect.That same process updates our in-house CRM automatically, logging notes and creating follow-up tasks on the account without me touching a keyboard.Before the next call, I can also get a prep email drafted that references the last meeting's action items and asks the prospect to confirm or add to the agenda, which saves a meaningful chunk of prep time. Drafting Proposals From Discovery Call Notes I can take the notes and conversation from a discovery call and have our AI agent draft a full proposal based on what was actually discussed, following our standard template.AI drafts it, then my team or I review and refine it before anything goes out, since it isn't perfect every time and can misstate an address or an offering if the original prompt wasn't clear enough.Human judgment is still required on scope and pricing specifically. AI has helped me think through pricing structures for different types of clients, but I'm the one making the final call. Keeping the CRM Honest AI logs my activity and updates CRM records and pipeline stages automatically, which keeps the data current without me manually entering it after every call.The accuracy still has to be mine to own. Whatever the pipeline shows is what I'm reporting up to leadership, so I double-check that it reflects reality rather than trusting the automation blindly.Dictation tools like Wispr Flow are pushing this even further, letting reps update records and direct their AI agents by talking instead of typing, which is only going to get more common. What AI Still Doesn't Replace AI doesn't replace the relationship, the judgment calls, or the actual conversation with a prospect, and that's exactly where I want to be spending more of my time.Research has shown reps spend a large share of their time, somewhere around 60%, on administrative work instead of actual selling, and that's the gap AI is closing for me.Some teams are taking this even further with inbound lead bots that hold full conversations and book meetings directly onto a calendar, with zero human touch until the call itself. "AI handles the admin so that I can spend more time actually selling." — Donald C. Kelly Leadership Advice, Books, and Quotes My challenge for you is: Write out or dictate your entire sales process to Claude or ChatGPT and ask it to identify exactly where AI or an agent could take something off your plate. Most reps underestimate what's possible here, mainly because it feels unfamiliar, not because the tools can't handle it. Resources Tell me what AI tools you're using, or why you're holding off, on LinkedIn. Check out Zenith for LinkedIn-based prospecting and outreach. Check out Fathom for automated meeting notes and recaps. Check out Wispr Flow for voice dictation that updates your tools directly. Check out Apollo and Lusha for prospect data and list enrichment. Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

  5. Oct 19

    Managing AI Agents Is Just Like Managing A New Employee

    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 It Kristie'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 Team Kristie'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 Verify Kristie 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 It Kristie 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 Built Her 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 Agent Kristie'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 Unchecked First, 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 is right because it sounds certain. We've Been Here Before: What the World Wide Web Panic Teaches Us Kristie points to the early internet as the closest historical parallel: people worried about losing control over where their information came from, the same fear now aimed at AI.Entire households once relied on a single printed encyclopedia set as the trusted source of information. That system eventually gave way, the same way old assumptions about static CRMs and manual workflows are giving way now.Her takeaway isn't to ignore the risk, but to recognize that fear of a major shift isn't new, and the companies that adapt early are the ones that come out ahead of it. What AI Fluency Actually Means Kristie is now asking about AI fluency directly in client hiring processes, and she defines it as a systems-level understanding of AI, not just knowing how to use one tool.That includes prompt literacy (can someone actually write a prompt that gets a useful result), output evaluation (how do you know if the agent's work is accurate or has quietly drifted), and tool selection (which AI platforms actually get adopted, standardized, and connected across the team).She's blunt with companies that call themselves "AI forward" but don't teach any of this during onboarding. Claiming the identity without building the actual skill doesn't hold up. Your First Step to Becoming AI Fluent Kristie's advice for any seller or leader who hasn't started: pick one tool, whether that's ChatGPT or Claude, and go build something small, like a custom GPT or a simple project.If you don't already use an AI notetaker, that's the bare minimum starting point, and she recommends having one in place within the week.Her closing advice is permission to fail: go make a mistake. Her own Friday agent didn't run the first time she built it, and that's a normal, expected part of learning the tool, not a sign it isn't worth doing. "I treat my agent like a four year old." — Kristie Jones Resources Connect with Kristie Jones on LinkedIn.Visit Kristie's site, Sales Acceleration Group.Join our LinkedIn cohort and learn to prospect the right way.Visit Blue Mango Studios for help creating podcast production content. 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...

    Managing AI Agents Is Just Like Managing A New Employee

  6. Oct 16

    Predicting the Hang Up: How Sales Fear Fulfills Itself

    The phone rings, they pick up, and before you've said a single word, you've already decided how this call is going to go. In this solo episode, I break down a pattern I see constantly in sales reps, including myself in the past. We walk into calls expecting rejection, and that expectation changes our behavior enough to actually cause it. The Prospect Isn't Reacting to Your Offer; They're Reacting to You Sociologist Robert K. Merton gave this phenomenon a name, "the self-fulfilling prophecy," a false belief that causes the exact behavior that makes the belief come true.Your expectation shapes how you act, and the other person responds to how you act, not to your actual intention or your offer.When a rep assumes a prospect is annoyed or uninterested based on nothing more than a hunch, that assumption changes their tone, their pace, and their confidence, and the prospect picks up on all of it. Where This Shows Up Most in a Sales Call Pricing is a major one. A rep starts offering a discount before the buyer has said a word about cost, which quietly signals the product isn't worth the full price in the first place.Email openers are another. Starting with "sorry to bother you" or "I know you're busy" trains the prospect to treat you like an interruption instead of someone trying to solve a real problem for them.Discovery calls suffer the same way. Reps skip the deeper questions because they assume the buyer won't want to answer them, and those deeper questions are usually exactly where the real insight lives. Follow-Up and Demos Take the Hit Too Some reps don't even book the follow-up call because they've already decided the prospect is going to ghost them, which kills the deal before it ever had a real chance.During demos, the same fear shows up as rushing through slides because a rep assumes the buyer is bored, when in most cases that assumption is just wrong.I had this happen recently on a client call. I assumed the prospects weren't engaged, but they were actually just muting themselves out of courtesy while discussing something privately on their end. Why We Do This to Ourselves Predicting rejection in advance is a defense mechanism. It hurts less when the rejection actually happens because some part of you already expected it.A bad call or two can quietly overgeneralize onto every prospect after it, even when the next person has nothing to do with what happened before.A lack of preparation makes this worse. Showing up to a call without enough research or practice leaves a rep feeling shaky, and that shakiness gets mistaken for a sign the call is doomed. How to Break the Pattern Separate the data from the story. Ask yourself what the prospect has actually said or done so far, and if the honest answer is "nothing yet," you're reacting to a story you made up, not to reality.If a prospect sounds off on the call, don't assume the worst. You can simply ask whether now is a bad time and offer a short version of your pitch instead, which hands control of the conversation back to you.Slow down on purpose. A calm opener earns far more attention than a rushed one, because rushing signals inexperience, while a steady pace signals quiet confidence. Prepare Like the Outcome Depends on It, Because It Does Know your opener and your first two questions so well that nerves never get the chance to take over, and practice them out loud until they feel automatic.Walk into every call expecting the best-case scenario instead of the worst, treating each prospect like they could become your best client, because that energy is genuinely palpable through the phone.Your prospect will often meet you at your own level of confidence, so the energy you bring into the call tends to come right back at you. The Five-Call Challenge On your next five calls, write down the negative outcome you're expecting before you dial, then write down what actually happens afterward.Most reps who try this find the gap between what they feared and what actually happened is much bigger than they expected.Once you can see that gap clearly, it gets a lot harder to keep walking into calls assuming the worst. "Stop writing the rejection, and start writing the progress." — Donald C. Kelly Resources Have a story about catching yourself in this pattern? Send me a message on LinkedIn and let me know how it worked out. Want coaching on building a repeatable opener and call process? Check out our Sales Mastermind. Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

    Predicting the Hang Up: How Sales Fear Fulfills Itself

  7. Oct 12

    4 Steps to Systematic Sales Growth

    "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 Confidence Systematic 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 Closing The 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 Reputation Consistent, 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 Conversions Social 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 Engine Most 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 Coexist A 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 Burgess Resources Connect with Jimmy Burgess on LinkedIn. Check out The Real Estate Sales Podcast, where industry experts share strategies that apply well beyond real estate. Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

    4 Steps to Systematic Sales Growth

  8. Oct 9

    The Top Three Issues Killing Your Sales Deals

    You did everything right, or at least you thought you did, and the deal still fell apart anyway. This one is coming from the archives, and the principles hold up just as well today as they did when we first recorded it. George Brontén, founder and CEO of Membrain and author of Stop Killing Deals, broke down the three deadly assumptions that quietly sink B2B sales deals, and how to catch them before they cost you the close. The Three Assumptions That Quietly Kill Deals Deals rarely fall apart because of one dramatic mistake, they fall apart because of small, invisible assumptions that go unchecked from the first call all the way to the close.The first flawed assumption is believing salespeople are simply born with the right traits, which leads to hiring extroverted, competitive people regardless of whether those traits actually fit the sales environment being sold into.A transactional sale and a complex, multi-year B2B sale call for completely different skill sets, so hiring for one generic "salesy" personality type instead of the specific environment is a mistake that shows up later in lost deals. Why Buyers Don't Decide Rationally The second assumption is believing buyers will act rationally once they're shown a logical case for the product, when in reality people buy with emotion first and rationalize the decision with logic afterward.Proving a product is the better choice on paper doesn't guarantee a rational decision back, because the buyer's hesitation is usually tied to internal risk, politics, or past experience that logic alone can't resolve.Understanding that gap between what buyers say and how they actually decide changes how a rep should run a sales conversation, shifting it from a pitch toward a genuine discussion about what's really driving the decision. The Myth of the Naturally Disciplined Seller The third assumption is expecting salespeople to be naturally disciplined enough to do whatever it takes to hit a number, when discipline is actually a set of habits that has to be built deliberately, not a trait people are simply born with.A lack of discipline shows up in small, specific gaps, like failing to identify every stakeholder in a deal or skipping a promised follow-up, and those small gaps are what let a deal quietly stall.The fix isn't willpower, it's building daily habits and structure into the sales process itself, so discipline becomes the default instead of something a rep has to summon on a hard day. The Number One Deal Killer: Not Knowing How the Decision Gets Made The single biggest issue killing B2B deals is not understanding how the buying decision will actually be made, or who besides the friendly first contact needs to be involved before anything moves forward.A rep can have a great conversation with an enthusiastic champion and still lose the deal entirely, because that champion was never the one with the authority or budget to make the final call.The fix is asking directly, early in the first call, how this kind of decision typically gets made and who else needs to weigh in, instead of assuming the friendly voice on the phone speaks for the whole organization. Why Discipline Determines Whether Deals Survive A lack of discipline often shows up as avoidance, like a rep who knows there are more stakeholders to loop in but skips that step because the conversation feels uncomfortable.One real example was a sales team that avoided engaging technical stakeholders because those conversations felt intimidating, so those technical buyers later torpedoed the deal out of fear the product would automate away their jobs.Once that sales team was coached to have those uncomfortable technical conversations directly, framing the product as freeing people up for better work instead of threatening their jobs, their win rates tripled. "If you can always identify all the right stakeholders in every deal, and if you have a sales team and you just focus on that for one year, you're going to improve your results massively." — George Brontén Leadership Advice, Books, and Quotes George Brontén is the author of Stop Killing Deals: How to Avoid Deadly Assumptions and Achieve Sales Excellence, which breaks down the three assumptions covered in this episode in more depth, along with practical ways to diagnose which one is hurting your own pipeline. Resources Connect with Brontén on LinkedIn. Learn more about Membrain, the sales enablement CRM built to guide, coach, and support B2B sales teams through the selling process. Grab a copy of Stop Killing Deals. Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

    The Top Three Issues Killing Your Sales Deals
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About

I believe in doing BIG THINGS! You should be earning 6 figures easily as a sales rep. But chances are you are not...yet! Sales is the most important department in every company but many sellers are never taught how to effectively sell, much less how to earn their way to high-income status. My own career limped along until a company I worked for invested in sales training to help me succeed. Immediately afterward, I closed a deal worth 4X what the company spent on me and saw hockey-stick improvement in my performance. So I started a podcast to “Evangelize” what was working. Today I interview the world's best sales experts, successful sellers, sales leaders and entrepreneurs who share their strategies to succeed in sales right now: folks like Jeffrey Gitomer, Jill Konrath, Bob Burg, and Guy Kawasaki to name a few. They share actionable insights and stories that will encourage, challenge, and motivate you to hustle your way to top income status. If you’re someone looking to take off in your sales career and earn the income you deserve, hit subscribe and let’s start doing BIG THINGS!

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  • Creator
    Donald C. Kelly
  • Years Active
    2021 - 2026
  • Episodes
    2K
  • Rating
    Clean
  • Copyright
    Copyright 2025 © The Sales Evangelist Podcast
  • Show Website
    The Sales Evangelist

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