Sales Discovery Mistakes That Kill Trust (Ask Jeb)

Your best rep is sitting at 130% of quota, and every instinct says it's time to hire. So you start writing the job description for another hire, bracing for three to six months of ramp time right when you need momentum most. Kyle Willis, VP of Growth at BELAY, thinks most sales leaders are betting on the wrong rep. Jeb Blount Jr. sits down with Kyle to break down what happens when a top performer gets a virtual sales assistant and wins back 5 to 10 hours a week. One rep pushed past 150% of quota, and her self-sourced pipeline grew enough that marketing could spend less. The difference came down to which work she handed off and which old leads she went back after.👉 Download Belay's Free "5 Reasons You Aren't Hitting Quota" Guide🎤 Get your ticket to the OutBound Conference📖 Purchase Jeb Blount's book, 90 Days to Level Up Your Sales SkillsOur Sponsors:* Check out Plaud AI and use my code JEB for a great deal: https://www.plaud.ai/jebAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

When prospects won't share their pain, pushing harder only raises the wall. In this episode of Ask Jeb on the Sales Gravy Podcast, Jeb Blount answers a question from Laura, who sells advertising in a crowded local market. Jeb explains why pain-focused discovery sounds self-serving and walks through the five decisions buyers make before they give you money.What You'll Learn:Why pain point questions make prospects hold backThe real reasons people buy, from aspiration to ego to brand awarenessThe five decisions buyers make before they do business with youWhy first impressions are not the final word on likabilityWhy listening is the fastest way to become likableHow to ask about a prospect's world and let them tell their storyHow giving your time and attention makes buyers feel importantHow value bridging connects a buyer's goals to your solutionHow micro stories help you sell intangibles through other clients' resultsWhy earning trust turns one-time buyers into repeat customers-Submit your question: salesgravy.com/askPurchase Jeb Blount's new book: 90 Days to Level Up Your Sales SkillsGrab your tickets for OutBound ConferenceFollow Jeb Blount on LinkedInFeatured Sponsor*If you're ready to upgrade your listening experience, go to go.fitnexa.com/gravy and use code GRAVY for $10 off your order.Our Sponsors:* Check out Plaud AI and use my code JEB for a great deal: https://www.plaud.ai/jebAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

Red herring objections are a buyer’s emotional self-protection and can derail a sales call fast. But you can break through them with the right approach. Jeb Blount shares a firsthand example from a software demo his own executive team sat through, showing exactly how a rep got baited into a defensive spiral that killed the deal. Jeb explains that most red herrings are built from a lifetime of bad experiences with salespeople and don’t always signal a deal-breaker. He lays out the discipline required to acknowledge these objections calmly, hold the agenda, and keep the sales conversation moving toward its actual objective.📖 Purchase Jeb Blount's book, Objections: The Ultimate Guide for Mastering the Art and Science of Getting Past No👉 Download the free Objections Book Club Guide for Sales Teams🔗 Follow us on LinkedIn!Featured Sponsor*If you're ready to upgrade your listening experience, go to go.fitnexa.com/gravy and use code GRAVY for $10 off your order.Our Sponsors:* Check out Plaud AI and use my code JEB for a great deal: https://www.plaud.ai/jebAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

Q2 gave us a lot of great sales conversations. These four taught us the most. Ashley Blount and Jeb Blount Jr. unpack what ties Mark Hunter's take on integrity, a hard-won deal recovery story, tactical language from Jeb Blount for reducing buyer friction, and a leadership lesson on empathy over sympathy. The lesson behind them: the right language, integrity, and mission are what turn conversations into long-term customers.📖 Purchase Jeb Blount's book, 90 Days to Level Up Your Sales Skills👉 Download our free A.C.E.D. Buyer Style Playbook for Sales Professionals🔗 Follow us on LinkedIn!Our Sponsors:* Check out Plaud AI and use my code JEB for a great deal: https://www.plaud.ai/jebAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

How do you know if your sales role is right for you? And how do you get better when you're the only rep on the team with no one to learn from?In this episode of Ask Jeb on the Sales Gravy Podcast, Jeb Blount answers two questions from Gabriel, an early-career business development rep in Montreal working at a small startup.Jeb's advice: at the start of your career, you often have to take what you can get and be the best at it, even if it isn't the right fit. As you gain experience, stop chasing the right company and start choosing the right leader. And when there's no top performer to follow, master the fundamentals and build your own learning path.What You'll Learn:Why entry-level salespeople rarely know if a role is the right fit, and why a bad fit still teaches you somethingThe questions to ask yourself to discover which sales role fits you bestWhy the right boss matters more than the right company, and how it can mean up to 20% higher incomeHow to vet a sales leader during the interview processWhy loving the sales process matters more than loving the product you sellHow to earn your role progressionWhy "find the top sales rep and copy them" is not helpful sales adviceHow to build your sales skills without a team around you through networking groups, sales conferences, and training-Submit your question: salesgravy.com/askPurchase Jeb Blount's new book: 90 Days to Level Up Your Sales SkillsGrab your tickets for OutBound ConferenceFollow Jeb Blount on LinkedInFeatured Sponsor*If you're ready to upgrade your listening experience, go to go.fitnexa.com/gravy and use code GRAVY for $10 off your order.Our Sponsors:* Check out Plaud AI and use my code JEB for a great deal: https://www.plaud.ai/jebAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

It’s easy to mistake motion for progress. But answering emails, updating the CRM, and sitting in internal meetings don’t generate revenue. In this episode of Money Monday, Jessica Stokes breaks down the concept of Golden Hours, the specific times during the day when prospects are most likely to pick up the phone or respond to outreach. She explains why protecting that time is one of the best revenue-generating decisions you can make in your sales career. Jessica also offers guidance to sales leaders on shielding their team’s selling windows from internal scheduling conflicts.📖 Purchase Jeb Blount's new book, 90 Days to Level Up Your Sales Skills💻 Enroll in Sales Gravy University Courses with Jessica Stokes👉 Download our Sales Gravy Time Audit Log for Sales Professionals🔗 Follow us on LinkedIn!Featured Sponsor*If you're ready to upgrade your listening experience, go to go.fitnexa.com/gravy and use code GRAVY for $10 off your order.Our Sponsors:* Check out Plaud AI and use my code JEB for a great deal: https://www.plaud.ai/jebAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

Tony Morris wants you to say less so you'll win more. It's his mantra for prospecting. Tony sat down with Jeb Blount Jr. to discuss how he has reframed his process so that he's not focused on being the seller, but on helping people be the buyer. He shares his rule that every month without contact costs you a slice of the relationship, and why he sends prospects books, articles, and webinar links with no ask attached. This approach breaks through buyer resistance more easily and gets you better conversations with your prospects. Tony will be at Outbound this year talking more about his process and why focusing on curiosity over closing creates more opportunity.🎟️ Grab your tickets for OutBound Conference💻 Enroll in Sales Gravy University Courses with Tony Morris👉 Download our free A.C.E.D. Buyer Style Playbook for Sales Professionals🔗 Follow us on LinkedIn!Our Sponsors:* Check out Plaud AI and use my code JEB for a great deal: https://www.plaud.ai/jebAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

How do you actually know someone can sell before you've hired them, trained them, and found out the hard way?In this episode of Ask Jeb on the Sales Gravy Podcast, Jeb Blount answers two hiring questions from Ramesh: how to find and hire the right salespeople, and whether that approach changes for a small company versus a large one.Jeb's answer: he's made the same hiring mistakes every leader makes, even after building a career on turning struggling sales teams around. Hiring is part process and part gut, there is no magic formula to get it right every time. The good news is you can stack the odds heavily in your favor with the right approach.What You'll Learn:How whether a role is heavy hunting, heavy account management, or a hybrid should shape who you hireWhere assessments fit into the hiring process and whyHow to build an assessment stack depending on the complexity of the roleHow to ask situational interview questions tailored to pushed past rehearsed answers Why bringing multiple people into the interview process catches what one person reviewing candidates alone will missHow a candidate's energy in an interview can mislead you if you don't weigh it against other signalsWhy small companies face higher hiring stakes than large companies, and how to protect yourself from a costly bad hireHow a long hiring cycle can cost you strong candidates to competitors who move fasterWhether you're building your first sales team or creating a hiring process at scale, this episode gives you a practical framework for making better hiring decisions.-Submit your question: salesgravy.com/askPurchase Jeb Blount's new book: 90 Days to Level Up Your Sales SkillsGrab your tickets for OutBound ConferenceFollow Jeb Blount on LinkedInOur Sponsors:* Check out Plaud AI and use my code JEB for a great deal: https://www.plaud.ai/jebAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

Admitting your company needs sales leadership is one of the hardest calls a founder makes, and one of the smartest. Duff Tucker walks you through seven critical signs that your company has outgrown founder-led sales, from reps getting check-ins instead of real coaching to a forecast that's become a guess instead of a weekly discipline. Duff breaks down what each sign actually looks like and how to spot it in your own company. Showing even one of the seven warning signs is reason enough to consider bringing on a fractional sales leader.🖋️ Read When to Hire a Fractional Sales Leader: 7 Signs Your Company is Ready🧑‍💼 Learn more about Sales Gravy’s Fractional Sales Leadership Solutions💻 Enroll in Sales Gravy University Courses with Duff Tucker🔗 Follow us on LinkedIn!Our Sponsors:* Check out Plaud AI and use my code JEB for a great deal: https://www.plaud.ai/jebAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

It sounds unusual, modeling an entire sales methodology off the principles of therapy. But it’s exactly what Jack Frimstone and Zac Thompson did, and it works. Jack and Zac, co-founders of the UK sales consultancy We Have a Meeting, sat down with Jeb Blount Jr. to break down this idea, which they discuss in their book, Sales as Therapy. They go over prospecting techniques that uncover real, often personal stakes behind a buying decision. They also discuss two tools that get more guarded prospects to open up.📖 Purchase Jeb Blount's book, 90 Days to Level Up Your Sales Skills👉 Download our free A.C.E.D. Buyer Style Playbook for Sales Professionals🔗 Follow us on LinkedIn!Our Sponsors:* Check out Plaud AI and use my code JEB for a great deal: https://www.plaud.ai/jebAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy