21 PERFECT Sales Discovery Questions to Ask Your Prospect (Part 1)

Chad Prezlomski reveals how elite sellers separate themselves from the pack by delivering a world-class buyer experience. Download the Guide: How to Get Your to Reply in 90 Seconds (Without Sending an Email) 🎙️ ACTIONABLE TAKEAWAYS: Before the meeting: Send pre-meeting nurture emails showing similar customers to build trust and credibility fast. During the meeting: Use a hypothesis slide to prove preparation and lead informed discovery. After the meeting: Use ChatGPT to identify the top three problems you can solve and send a recap video or email. One thing to do: Add a hypothesis slide to every deck to make your prep visible and elevate the buyer’s experience. CHAD’S PATH TO PRESIDENT’S CLUB: Top-Tier Enterprise AE @ Blackbaud & Amplify Sales Leader @ Schoology & Splash (10+ Years Building Teams) VP of Sales @ Splash — Scaled Org to Cvent Acquisition (2024) RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” Free Sales Templates, Scripts and Guides

Get your prospect to spill their guts on the very FIRST discovery call! In this first episode of a three-part 30 Minutes to President’s Club series, host Nick Cegelski reveals the 10 best discovery questions top-performing sales reps use to get prospects to open up from the very first call. These early-stage discovery questions are designed to uncover true motivation, business pain, and urgency — not just surface-level interest. You’ll learn exactly how to guide your conversations with questions that make prospects tell stories, reveal priorities, and show you how to win the deal. This is Part 1 of Nick’s Discovery Series, covering early-stage sales discovery — with Parts 2 and 3 diving into mid-stage and late-stage deal questions. Whether you’re a new AE or a veteran seller, this episode will sharpen your discovery skills, help you qualify faster, and teach you how to use the Discovery Tree to direct conversations like a pro. Subscribe so you don’t miss the next episodes and start mastering the art of discovery today. RESOURCES DISCUSSED Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” Free Sales Templates, Scripts and Guides

In this episode, Armand Farrokh breaks down exactly how to run a discovery call for any product, even one you’ve never sold before. Using a background check software as an example, he shows how to identify real business problems, craft targeted questions, and connect day-to-day pains to executive-level impact that drives urgency. You’ll learn how to build and navigate a Discovery Tree—a structured path from situation to operational problem to executive impact, using Armand’s proven framework. He also shares “typically” and “magic moment” questions that uncover high-value pain points, helping SDRs, AEs, and sales leaders turn every discovery call into a winning deal. RESOURCES DISCUSSED Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” Free Sales Templates, Scripts and Guides

Shaun Crimmins reveals how elite sales leaders simplify the math, build winning rhythms, and coach reps with data-driven precision. 🎙️ ACTIONABLE TAKEAWAYS: Reverse engineer revenue goals into weekly sales behaviors your reps can control. Create an operating rhythm—consistent meetings, deal reviews, and cadences to eliminate chaos. Coach with metrics, not gut feel—identify data gaps, validate behaviors, and build coaching plans. Prepare like a pro—leaders must prep for every 1:1 just as reps prep for customer calls. SHAUN’S PATH TO PRESIDENT’S CLUB: HubSpot: Helped scale revenue from $60M → $300M, Series D → IPO. Vanta: Scaled revenue from $10M → $100M+, led North America sales team and doubled win rates. Gong: Leads Commercial Business in the East. RESOURCES DISCUSSED Metrics Dashboard Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” Free Sales Templates, Scripts and Guides

🚨 SAVE $100 ONLY IF YOU JOIN THE COURSE BEFORE 10/17: https://bit.ly/4o8KtMT Sales managers: No one ever teaches you how to do your job. If you've ever wondered... Why are my pipeline reviews useless? Should I actually hire this person or am I gonna have to fire them in three months? Guess what? You're probably a little bit like me and you had to figure out this stuff from scratch. Well, fortunately, I've partnered up with the best sales leader in the game today, Mark Kosoglow. He led Outreach from $0-250M ARR and has turned 8 managers into VPs of Sales. All through his sales management operating system. It is the gold standard for how to be a sales leader in three steps: 1. The Operating System: Everything from how you forecast, to how you drive a deal through your pipeline, to how your AE should prospect. 2. The Operating Rhythm: How do you make sure your reps are actually doing the system through deal reviews? Team meetings and one-on-ones. 3. The Talent System: How do you hire people who are so good that they literally make you look like you don't have to do anything for your job? That is what we cover in the Sales Management Operating System course. I guarantee it will be the best sales management resource you've ever used in your life. 🚨 SAVE $100 ONLY IF YOU JOIN THE COURSE BEFORE 10/17: https://bit.ly/4o8KtMT 🛠️ The 15 Page Sales Management Operating System Toolkit: https://www.30mpc.com/blog/the-ultimate-sales-management-operating-system-guide #salesmanagementtraining#salesleadership#managertotrainer#forecasting#dealreviews#salescoach#B2Bsales#salesmanagers#salesoperatingrhythm#prospectingstrategies#salestrainingtips#revenuegrowth#leadershipdevelopment#salesenablement#onboardingmanagers

Mark's Kosoglow's Sales Leadership Course Armand Farrokh reveals how to close a $3K, $30K, and $300K sales deal — and why each one needs a different approach. He breaks down the five buyer agreements that drive every close and shows how to spot deal momentum to accelerate your cycle. Whether you’re closing SMB, mid-market, or enterprise deals, this video gives you real-world B2B sales tactics, SaaS closing strategies, and deal frameworks to help you sell faster, smarter, and bigger. RESOURCES DISCUSSED Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” Free Sales Templates, Scripts and Guides

🚨 SAVE $100 ONLY IF YOU JOIN THE COURSE BEFORE 10/17: https://bit.ly/4o8KtMT Sales managers: No one ever teaches you how to do your job. If you've ever wondered... Why are my pipeline reviews useless? Should I actually hire this person or am I gonna have to fire them in three months? Guess what? You're probably a little bit like me and you had to figure out this stuff from scratch. Well, fortunately, I've partnered up with the best sales leader in the game today, Mark Kosoglow. He led Outreach from $0-250M ARR and has turned 8 managers into VPs of Sales. All through his sales management operating system. It is the gold standard for how to be a sales leader in three steps: The Operating System: Everything from how you forecast, to how you drive a deal through your pipeline, to how your AE should prospect. The Operating Rhythm: How do you make sure your reps are actually doing the system through deal reviews? Team meetings and one-on-ones. The Talent System: How do you hire people who are so good that they literally make you look like you don't have to do anything for your job? That is what we cover in the Sales Management Operating System course. I guarantee it will be the best sales management resource you've ever used in your life.

Huge Announcement 👉 Our next course is here: The Sales Management Operating System Free Launch Event: Mark will walk you through his entire system, for free. You’ll walk away with more tactical leadership training in that hour than most paid courses deliver. 🎟️ Reserve Your Ticket: https://hubs.li/Q03L52Mc0 Discounted Pre-Order Access: By signing up for the event, you’ll unlock early access to our upcoming Sales Leadership Course, at the lowest price it'll will ever be. Exclusive Toolkit: Everyone who shows up live gets access to the Sales Management Advanced Implementation Playbook, the exact internal systems Mark used to scale Outreach from $0 → $250M. This playbook has never been shared publicly. Live attendees only. What You Need To Know: Most new managers lead off gut — finger-in-the-air forecasting, feast-or-famine teams, and hiring that’s a coin flip. This course fixes that. You’ll learn the exact systems Mark Kosoglow used to scale Outreach from $0 to $250M ARR and coach 8 managers into VPs: → The Operating System to build a bulletproof sales process → The Operating Rhythm to get every rep performing like your #1 → The Talent System to hire and ramp reps who actually hit quota If you don’t have a system, leadership feels like firefighting. If you do, it becomes your biggest multiplier for revenue and career growth. Register FREE → https://hubs.li/Q03L52Mc0 --- Sales hiring is broken—and here's how to fix it. If you've ever felt like your pipeline reviews are useless or your forecast is just a wild guess, you're not alone. Most sales managers are never taught how to actually hire great reps—until now. In this game-changing video, we break down a bulletproof 4-step hiring system used by Mark Kosoglow, former VP of Sales at Outreach, who scaled it from $0 to $250M+ ARR and developed 8 sales managers into full-fledged VPs. We reveal why most sales hiring strategies over-index on experience instead of traits, and how you can flip your process to uncover high-performing reps who thrive in ambiguity, have coachability, grit, passion, and more. Learn the nine essential traits that actually drive results and discover the interview playbook that uncovers them all. Whether you’re building your first team or trying to fix a broken one, this video will reshape how you think about hiring in sales—forever. The Sales Recruiting Playbook (Sales Interview + Sourcing Guide): https://www.30mpc.com/blog/the-sales-recruiting-playbook

This Is Why Everyone Else Is Getting Promoted Faster Wondering why you’re stuck while your peers keep getting promoted? It’s not about tenure or luck—it’s about strategy. In this video, we break down the hard truth behind why others are getting promoted faster than you. Based on the career journey of a former VP of Sales who jumped multiple levels by age 29, you’ll get a clear 4-step framework that helps you outperform, gain leverage, and control your own promotion path. If you’re tired of waiting your turn, or feel like your hard work isn’t being recognized, this is your wake-up call. Learn how to become undeniable, run your own promotion “sales cycle,” and make it impossible for leadership to overlook you. Perfect for SDRs, AEs, and any high-performer in a competitive sales org. RESOURCES DISCUSSED: Join our weekly newsletter - https://hubs.li/Q02NJQmg0 Things you can steal - https://linktr.ee/30mpc Save $50 on any 30MPC course - https://www.30mpc.com/courses with code “PODCAST” Free Sales Templates, Scripts and Guides - https://www.30mpc.com/toolkit

Huge Announcement 👉 Our next course is here: The Sales Management Operating System Free Launch Event: Mark will walk you through his entire system, for free. You’ll walk away with more tactical leadership training in that hour than most paid courses deliver. 🎟️ Reserve Your Ticket: https://hubs.li/Q03L52Mc0 Discounted Pre-Order Access: By signing up for the event, you’ll unlock early access to our upcoming Sales Leadership Course, at the lowest price it'll will ever be. Exclusive Toolkit: Everyone who shows up live gets access to the Sales Management Advanced Implementation Playbook, the exact internal systems Mark used to scale Outreach from $0 → $250M. This playbook has never been shared publicly. Live attendees only. What You Need To Know: Most new managers lead off gut — finger-in-the-air forecasting, feast-or-famine teams, and hiring that’s a coin flip. This course fixes that. You’ll learn the exact systems Mark Kosoglow used to scale Outreach from $0 to $250M ARR and coach 8 managers into VPs: → The Operating System to build a bulletproof sales process → The Operating Rhythm to get every rep performing like your #1 → The Talent System to hire and ramp reps who actually hit quota If you don’t have a system, leadership feels like firefighting. If you do, it becomes your biggest multiplier for revenue and career growth. Register FREE → https://hubs.li/Q03L52Mc0 --- To celebrate the launch of Mark's new leadership course, please enjoy a throwback to his SECOND EVER episode on 30MPC from all the way in 2023. Four Actionable Takeaways:  B2C Mall Sales Hustle: Show them what their world looks like with your product RIGHT NOW. When they prompt a creative deal term, say yes first, but then ask: “Does that mean you’ll buy now?” If not, keep digging. Good creative deals lose in the short term but win in the long term. You might take the buyout hit today, but that’s ok if you keep the customer for 3 years. When a customer asks for new product guarantees in a contract, ask: “Is what you want to be built really preventing you from achieving the result that you want?”