I Used To Be Crap At Sales

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Oct 2026

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About the show

Even the most prominent voices in Sales were crap at Sales once. Join bestselling Author, Founder and Sales Coach Mark Ackers as he speaks with successful Sales professionals about their early Sales struggles, and how they overcame these challenges to become the people they are today.

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31 recent

October 14, 2026Episode 301 hr 9 min

We've Done Sales Training. Why Has Nothing Changed? | EP30 | Becky Abrahams

You paid for the sales training, the team left the room buzzing, and by Monday nobody was doing anything differently. Most sales enablement teams have watched that happen, and most leaders book another workshop anyway. In this episode, Becky Abraham sits with Mark Ackers to talk about why sales training and new sales methodologies so rarely stick, what sales enablement actually does day to day, and what she learned helping more than 40 companies roll out the Challenger Sale. She also gets into why reps don't want enablement or their own manager as their coach, why introverts can be very good at sales, and what AI sales tools are doing to how sellers think. 📥 HAVE YOUR SAY. Take the State of Sales Coaching in 2027 survey (prizes up for grabs) Who this episode is for: You've run sales training or a kickoff and can't see what changed afterwards You've bought into a sales methodology and the team has quietly gone back to the old way You lead or work in sales enablement and want to prove it's more than sending training invites You're an introvert in sales and you've been told the job is built for extroverts Key takeaways: A one-day workshop builds energy and goodwill, but behaviour doesn't change unless the system around it reinforces the change Becky doesn't care which sales methodology you choose - how you roll it out matters far more than what you roll out Reinforcement means managers know what good looks like and look for it in every deal review, call prep and CRM note, for six to 12 months In the MySalesCoach 2026 State of Sales Coaching survey, 66% of reps wanted an external coach and fewer than 5% wanted sales enablement - what are Beckys thoughts on this as an enablement leader? Sales managers tend to do and tell rather than coach, because their number is tied to the rep's number Introverts can do well in enterprise sales because they want to go deep, and they often need a few seconds to process before they answer AI works in the probable and humans work in the possible (a line Becky credits to Alan Verstig of Growth Matters) - a seller earns their place by bringing the implementation story the buyer can't get from research 🔗 Connect with Mark Ackers on LinkedIn 🔗 Connect with Becky Abraham on LinkedIn 🔗 🔗 Follow MySalesCoach on LinkedIn Like, leave a comment and subscribe for more! Brought to you by MySalesCoach. www.mysalescoach.com 📥 Download the Modern Revenue Leader's Sales Coaching Manual: https://bit.ly/4nyx5m2

September 9, 2026Episode 291 hr 11 min

I never coached my team. Now I lose sleep if i miss a session | EP29 | Brett James

Most sales leaders think they're coaching their team. A lot of them are managing it and calling it coaching. In this episode, Brett James sits with Mark Ackers to talk about the sales coaching techniques he runs every week and the difference between coaching and managing a sales team - call playback, specific-segment role play, asking questions instead of giving answers, and where the line sits between coaching a deal and hero managing it. He's also honest about what that intensity has cost the people who worked for him, and about the cancer diagnosis that changed how he leads. 📥 Download the Modern Revenue Leader's Sales Coaching Manual: https://bit.ly/4nyx5m2 Who this episode is for: You lead a sales team and suspect you're doing too much of the selling yourself You can't stop taking over your reps' calls and you know it isn't helping them You want practical sales coaching techniques you can run this week, not theory You've been promoted for being the best seller and nobody has taught you how to coach Key takeaways: Managing people and coaching people are two different jobs - Brett ran a sales team for years without realising coaching was even a thing Call playback is the technique that flipped it for him, and he'd been recording calls for years before anyone suggested reviewing one with a rep Keep pipeline one-to-ones separate from coaching sessions, because run together the deal always wins and the skill never gets touched Ask questions rather than hand over answers - Brett makes himself go last, on the basis that a rep who works it out remembers it Stop role playing whole calls and role play one specific moment instead, like the close of a demo, and call it practice rather than role play Hero managing is stepping in to win the deal for your rep, and Brett is honest that he still does it because he wants the deal Ask people how they are before you open the pipeline - it's the smallest change he made and the one he wishes he'd made years earlier 🔗 Connect with Mark Ackers on LinkedIn 🔗 Connect with Brett James on LinkedIn 🔗 Follow MySalesCoach on LinkedIn Like, leave a comment and subscribe for more! Brought to you by MySalesCoach. www.mysalescoach.com

July 8, 2026Episode 2850 min

What Nobody Tells You About Becoming a First Time Sales Manager | EP28 | Callum Mackay

Most people get their first sales management role because they were good at selling and good at putting themselves forward. Nobody warns them it's a different job - or that the drive that got them there can be the same thing that burns them out. Callum Mackay moved into management early in his career, building and leading sales teams through startup and scale-up environments. He's honest about the whole arc - the buzz of a first sale with a team he built, the imposter syndrome running at 250%, and the year of stress that ended with him being signed off work. 📥 Download the Modern Revenue Leader's Sales Coaching Manual: https://bit.ly/4nyx5m2 🎯 Who this episode is for: You've just stepped into your first sales management role and it's harder than you expected You're a strong performer thinking about management and want to know what you're walking into You lead sales managers and want to understand the pressure they're actually under You've felt work stress creep into your body and want to hear someone talk about it honestly In this episode, Callum sits with Mark Ackers to talk about the first-time sales manager role and why so few people are prepared for it - the shift from selling to leading, being a coach instead of a hero manager, managing up when the numbers are down, and protecting your mental health while still carrying a target. It's an honest conversation about the parts of sales leadership that don't make it into the job description. 💡 Key takeaways: Putting yourself forward before you feel ready is a career skill - but without healthy boundaries, that same drive is what burns you out You can think management is about people and coaching, and be blindsided by the numbers, forecasting and diagnostic side that's actually half the job Feedback is a gift - avoiding difficult conversations early doesn't protect anyone, it just delays the damage If you could win every deal yourself you wouldn't need a team - being a coach means letting people make mistakes, even when it costs a deal Visibility is real: in the office people see your effort, and when you're remote you have to deliberately share what you're doing or it doesn't count No job or career is worth your mental or physical health - Callum was signed off work with stress and is honest about what got him there and what got him out Focusing on what you can control, box breathing, walks and talking to someone are simple things that pulled him back from the edge 🔗 Connect with Mark Ackers on LinkedIn 🔗 Connect with Callum Mackay on LinkedIn 🔗 Follow MySalesCoach on LinkedIn Like and subscribe for more! www.mysalescoach.com

May 20, 2026Episode 271 hr 4 min

Why the Best Salespeople Struggle Most When They Become Managers | EP27 | John Mason

Episode 27: Why the Best Salespeople Struggle Most When They Become Managers Most sales managers are promoted because they were great at selling. The problem is that selling and managing are two different jobs - and nobody tells you that before you take the role. 📥 Download the Modern Revenue Leader's Sales Coaching Manual: https://bit.ly/4nyx5m2 🔗 Connect with Mark Ackers on LinkedIn 🔗 Connect with John Mason on LinkedIn 🔗 Follow MySalesCoach on LinkedIn 🎯 Who this episode is for: You've just been promoted into sales management and have no idea what you're doing on a Monday You're a top performer thinking about going into management and want to know what you're walking into You're already in the seat and it's harder than you expected You lead or support first-time sales managers and want to understand what they're going through 💡 Key takeaways: Imposter syndrome doesn't go away when you get promoted — it resets at the start of every new chapter of your career Top performers default to "do what I did" when they become managers — it's the only reference point they have, and it rarely works The job fundamentally switches from being about you to being about other people — that's a bigger shift than most people are warned about before they say yes Most managers understand their team's motivations at a headline level only — the real motivator is always underneath it The metrics sales leaders chase most often measure the wrong things — activity numbers don't tell you why someone is struggling Your first weeks as a manager will involve things nobody put in the job description — and that's normal, not a sign you're failing Training that feels like a tick-box exercise usually is — real development requires ongoing coaching, not a half-day workshop John Mason has been on both sides. He moved from SDR through to heading up business development teams, and he's lived the top performer to manager transition himself — firefighting on day one, carrying a quota while trying to figure out how to interview, forecast, and have conversations he'd never had before. In this episode, John sits with Mark Ackers to dig into the real sales management challenges that come with the first-time sales manager role — and why the sales leadership coaching and development most companies offer doesn't come close to preparing you for it. The sales manager promotion feels like a reward. What it actually is, is a completely different job. Like and subscribe for more! www.mysalescoach.com

November 26, 2025Episode 261 hr 5 min

The '3 Whys' Framework Top Performers Use To Close More Deals | EP26 | Scott Cowley

Why do top performers consistently close more deals — even when they’re selling the same product, to the same market, with the same tools? In this episode, Scott Cowley breaks down the “3 Whys” Framework — the system elite sellers master that most reps never even think about. Top performers don’t win because they have better personalities, smoother pitches, or clever hacks. They win because they deeply understand the three questions every buyer must answer before they ever commit: 1️⃣ Why buy anything? 2️⃣ Why buy now? 3️⃣ Why buy you? Scott learned this the hard way: after nine months in a sales job without closing a single deal, he realised he didn’t understand any of the real Whys buyers use to make decisions. Today, the 3 Whys form the backbone of how he teaches founders, SDRs, AEs, and revenue leaders to sell in a more predictable, high-impact way. In this episode you’ll learn: 🔥 Why deals “stall” (and why that’s just a missing Why Now) 🔥 How elite sellers create clarity, not pressure 🔥 The seasonality mistakes that cost companies months of pipeline 🔥 Why most training focuses on the wrong Why 🔥 How to build discovery that uncovers real, actionable change drivers If your pipeline feels unpredictable — this framework will change how you sell.

October 23, 2025Episode 251 hr 0 min

The Two Silent Killers Destroying Sales Careers (And How To Beat Them) | EP25 | Jessica Williams

Most salespeople don’t fail because they can’t sell — they fail because of mindset. In this episode, Jessica A. Williams, Founder of Just Williams, joins Mark Ackers to expose the two silent killers that quietly destroy sales careers: need for approval and impostor syndrome. From being kicked out of school to leading an award-winning B Corp, Jessica shares the raw truth about people-pleasing, burnout, and rebuilding confidence with boundaries, coaching, and self-awareness. 🔥 You’ll learn: • Why need for approval in sales kills performance • How impostor syndrome thrives even in top performers • The role of self-awareness and journaling in sustainable success • How to set boundaries and stop people-pleasing • Leadership lessons for building a values-led, resilient sales culture 🎧 Listen, reflect, and discover how to silence both killers before they derail your career. ⸻ 👍 Like this episode? Don’t forget to like, comment, and subscribe for more sales coaching insights! ✅ Book a call to find out how we can support your sales team: https://www.mysalescoach.com/book-a-meeting ✅ Connect with Us on Linkedin: - Mark Ackers: https://www.linkedin.com/in/markackers/ - MySalesCoach: https://www.linkedin.com/company/mysalescoach-com - Jessica Williams: https://www.linkedin.com/in/justjessicawilliams/ ✅ SUBSCRIBE to the audio podcast — I Used To Be Crap At Sales: Apple Podcasts → https://podcasts.apple.com/us/podcast/i-used-to-be-crap-at-sales/id1734830248 Spotify → https://open.spotify.com/show/0uhvimbYfGIfr456Az2MW4 Amazon Podcasts → https://music.amazon.com/podcasts/b85042dd-4d6b-4fbe-9d9e-11dcdbddd20a/i-used-to-be-crap-at-sales #SalesPodcast #SalesMindset #NeedForApproval #ImpostorSyndrome #SalesCoaching #SalesLeadership #SalesTraining #SalesCareer #SalesSelfAwareness #SalesPerformance #SalesDevelopment #B2BSales

September 24, 2025Episode 2458 min

TOP 15% of Salespeople Do THIS to Stay on Top |EP24| Niraj Kapur

Most salespeople stay stuck in the middle of the pack. Some even survive decades in sales without ever breaking through. But a small group — just 15% — consistently smash target, year after year. In this episode, our host Mark Ackers sits with sales influencer and coach Niraj Kapur shares how he went from “horrendous at sales” (his words) to becoming one of the most respected trainers in the industry. His story is brutally honest — from reading rejection scripts with no clue what to say, to being nominated for Salesman of the Year . You’ll discover: Why 80% of sellers fail to hit quota in 2025 (and why it’s not just about bad leads). The mindset shift that separates mediocre reps from top 15% performers. How detaching from outcomes can actually increase your close rate. Simple prospecting techniques that help you stand out in a sea of sameness. Why investing in yourself matters more than waiting for your boss to back you. If you’re tired of feeling average, this episode is your wake-up call. Niraj doesn’t sugarcoat it — he lays out the hard truths and the daily habits that build sales winners. 👉 Whether you’re an SDR fighting for pipeline or a sales leader trying to lift your team, this is an unmissable conversation. #Sales #SalesCoaching #SalesMindset #SalesLeadership #Prospecting #SalesTraining #B2BSales #LinkedInSales #SalesPodcast #SalesPerformance #SocialSelling

August 20, 2025Episode 231 hr 28 min

From The Sales Floor To BBC Traitors Final Four |EP23| Andrew Jenkins

What happens when a seasoned sales leader enters one of the most intense BBC reality shows on TV? Andrew Jenkins spent over 20 years in Sales — building trust, leading teams, and coaching people through high-pressure sales at Lloyds Bank. Then he brought those same skills — listening, emotional intelligence, and calm under pressure — into the castle on The Traitors. The result? He made it to the Final Four. In this conversation, Andrew unpacks how: • Relationship-building helped him avoid votes while others got banished • Sales coaching taught him to listen more, speak less — even in a roundtable showdown • Empathy, not ego, helped him build alliances and stay grounded • His experience leading teams under pressure was the perfect training for reality TV’s mind games Plus, we explore his life after trauma, leaving a high-performing career at its peak, and why he now speaks to companies about failure, resilience, and mental health. 👇 If you’ve ever wondered whether soft skills really matter in your sales career — watch this episode. #TheTraitorsBBC #SalesLeadership #salestips #EmotionalIntelligence #salestraining #salescoaching #SalesMindset #TrustBasedSelling #ResilienceInSales #SalesLife #salespodcast #AuthenticSelling

July 23, 2025Episode 221 hr 3 min

The Marketing vs Sales Blame Game Is Costing You Millions |EP22| Mark Walker

If you’ve ever felt the tension between sales and marketing… you’re not alone. In this episode, Mark Walker (who's lived both lives) joins our host Mark Ackers to explore one of the most persistent pain points in B2B: sales and marketing alignment. From junk MQLs to misattributed pipeline, they pull no punches in exposing the outdated structures, broken metrics, and political infighting that derail revenue teams. You’ll learn how to rethink SDR reporting lines, why most account based marketing (ABM) campaigns fall flat, and what it really means to align around revenue. 🔑 In this episode, you’ll learn: • Why confidence in your product is critical for sales success • How one viral video built instant buyer trust • The real reason MQLs break trust between sales and marketing • Why some marketers should earn commission—and some SDRs shouldn’t • A bold take on founder-led sales and roadmap discipline • What great ABM looks like (and how to fix it fast) Whether you’re a CRO, CMO, or sales leader tired of the blame game—this episode gives you the tools and mindset to build a unified revenue engine. ✅ Find out more about how MySalesCoach are supporting sales teams like yours: / https://www.mysalescoach.com/ ✅ Get a MySalesCoach Membership, for you or your team for only £20 per month per person (+vat) https://www.mysalescoach.com/pricing ✅ Connect with Us: Follow Mark Ackers on LinkedIn: / https://www.linkedin.com/in/markackers/ Follow MySalesCoach on LinkedIn: / https://www.linkedin.com/company/mysalescoach-com Follow Mark Walker on LinkedIn: / https://www.linkedin.com/in/jfdimark/ ✅ SUBSCRIBE to the audio Podcast I USED TO BE CRAP AT SALES: Subscribe and Review on iTunes: https://podcasts.apple.com/us/podcast/i-used-to-be-crap-at-sales/id1734830248 Subscribe and Review on Spotify: https://open.spotify.com/show/0uhvimbYfGIfr456Az2MW4 Subscribe and Review on Amazon Podcasts: https://music.amazon.com/podcasts/b85042dd-4d6b-4fbe-9d9e-11dcdbddd20a/i-used-to-be-crap-at-sales 👍 Like this episode? Don’t forget to like, comment, and subscribe for more sales coaching insights! #SalesAndMarketingAlignment #ABM #B2BSales #SalesDevelopment #FounderLedSales #SDRLeadership #RevOps #GoToMarketStrategy #SalesEnablement #RevenueLeadership #SalesTraining #salescoaching

June 18, 2025Episode 211 hr 8 min

Why 94% of Salespeople Never Become Elite, And How To Fix |EP21| Will Aitken

🎤 In this must-listen episode of The "I Used to Be Crap at Sales" Podcast, host Mark Ackers interviews Will Aitken, one of the most recognised voices in sales content today. Will is a former SaaS AE turned sales coach, keynote speaker, and viral content creator with over 140,000 LinkedIn followers and millions of views across TikTok and YouTube. He’s built a global audience by combining relatable sales insights with unforgettable humour—and today, he’s opening up like never before. 🔥 What You'll Learn: 👉 Why “need for approval in sales” is the #1 mindset trap holding reps back 👉 How Will went from underperforming rep to sales leader and content icon 👉 How becoming coachable changed everything in Will's career and life 👉 The truth about ego, self-worth, and seeking validation through work This is more than a sales conversation—it’s a roadmap for anyone who’s ever doubted themselves, felt stuck in their role, or wanted to take control of their growth. Whether you're a sales rep, leader, or creator, Will's story will leave you inspired and equipped. 👍 Like this episode? Don’t forget to like, comment, and subscribe for more sales coaching insights! ✅ Find out more about MySalesCoach https://www.mysalescoach.com/ ✅ Seriously level up yours/ your team’s sales skills with a MySalesCoach Membership for only £20 per month (+vat) https://www.mysalescoach.com/pricing ✅ Connect with Us: Follow Mark Ackers on LinkedIn: https://www.linkedin.com/in/markackers/ Follow MySalesCoach on LinkedIn: https://www.linkedin.com/company/mysalescoach-com Follow Will Aitken on LinkedIn: https://www.linkedin.com/in/justwillaitken/