Advertise on podcast: I Used To Be Crap At Sales

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 yourselfYou can't stop taking over your reps' calls and you know it isn't helping themYou want practical sales coaching techniques you can run this week, not theoryYou've been promoted for being the best seller and nobody has taught you how to coachKey takeaways: Managing people and coaching people are two different jobs - Brett ran a sales team for years without realising coaching was even a thingCall playback is the technique that flipped it for him, and he'd been recording calls for years before anyone suggested reviewing one with a repKeep pipeline one-to-ones separate from coaching sessions, because run together the deal always wins and the skill never gets touchedAsk questions rather than hand over answers - Brett makes himself go last, on the basis that a rep who works it out remembers itStop role playing whole calls and role play one specific moment instead, like the close of a demo, and call it practice rather than role playHero managing is stepping in to win the deal for your rep, and Brett is honest that he still does it because he wants the dealAsk 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

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 expectedYou're a strong performer thinking about management and want to know what you're walking intoYou lead sales managers and want to understand the pressure they're actually underYou've felt work stress creep into your body and want to hear someone talk about it honestlyIn 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 outYou can think management is about people and coaching, and be blindsided by the numbers, forecasting and diagnostic side that's actually half the jobFeedback is a gift - avoiding difficult conversations early doesn't protect anyone, it just delays the damageIf 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 dealVisibility 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 countNo 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 outFocusing 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

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 MondayYou're a top performer thinking about going into management and want to know what you're walking intoYou're already in the seat and it's harder than you expectedYou 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 careerTop performers default to "do what I did" when they become managers — it's the only reference point they have, and it rarely worksThe 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 yesMost managers understand their team's motivations at a headline level only — the real motivator is always underneath itThe metrics sales leaders chase most often measure the wrong things — activity numbers don't tell you why someone is strugglingYour first weeks as a manager will involve things nobody put in the job description — and that's normal, not a sign you're failingTraining that feels like a tick-box exercise usually is — real development requires ongoing coaching, not a half-day workshopJohn 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

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.

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/id1734830248Spotify → https://open.spotify.com/show/0uhvimbYfGIfr456Az2MW4Amazon 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

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

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

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-comFollow 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

🎤 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 MySalesCoachhttps://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-comFollow Will Aitken on LinkedIn: https://www.linkedin.com/in/justwillaitken/

Leading a global SDR team? Just promoted to SDR manager? This episode is packed with real-world advice from Catherine Olivier, VP of Global Sales Development at Cognism, on how to build and lead high-performing sales development teams—without burning out or losing your team’s trust. Catherine shares hard-earned lessons from her experience leading SDR teams across the US, UK, Germany, and France. She unpacks what most first-time SDR managers get wrong, how to avoid managing like your old boss, and the biggest mistakes leaders make in a hybrid, high-pressure sales environment. Learn how to:✅ Structure and scale global SDR teams✅ Manage former peers without favouritism✅ Coach new SDR managers for long-term success✅ Avoid common leadership traps and burnout✅ Build culture in remote sales teams✅ Deal with imposter syndrome in sales leadership 👍 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 teams 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-comFollow Catherine Olivier on LinkedIn: /  https://www.linkedin.com/in/catherine-olivier/

In this unmissable episode of The I Used To Be Crap At Sales Podcast, legendary sales trainer Josh Braun, joins our host Mark Ackers for a deep, unfiltered dive into what really drives consistent sales performance. If you’re a sales rep chasing targets, a team leader trying to motivate your reps, or a founder building a sales motion—this episode is your blueprint for rewiring your sales mindset. Josh breaks down why most sellers fail—not from lack of skill, but from clinging too tightly to outcomes and things they can't control. Learn how to detach from the outcome, build trust through radical honesty, and shift your energy from desperate to magnetic. You’ll discover why storytelling beats pitching every time, and how to start collecting your own to paint a picture. You'll learn how to provoke prospects and poke the bear without being pushy, and how mindfulness and meditation make you a sharper communicator. He shares many captivating, real life stories in this episode—from shopping for sneakers to his Grandma's toaster—that turn abstract concepts into, memorable and practical sales coaching gold. Whether you’re hitting the phones or scaling your team, this episode gives you the tools to sell with integrity, curiosity, and calm control. This isn’t just sales advice—it’s a mindset rewiring that could transform your entire approach to selling.

How do you truly motivate a sales team? Most sales leaders struggle to keep their teams engaged and performing at their best - especially with 53% of the workforce being made up of Millennials and Gen Z. In this episode, our host Mark Ackers sits down with Phil Putnam, the author of Desire-Based Leadership, to uncover the secrets behind scaling high-performing sales teams and retaining top talent. Phil shares a game-changing leadership framework that shifts the focus from company goals to what employees truly want - because when salespeople believe their job helps them achieve their life goals, performance skyrockets.  We dive into real-world leadership mistakes, how to avoid costly attrition, and why traditional motivational tactics no longer work.   You’ll hear powerful insights on:  Why most leaders fail to motivate their teams (and how to fix it)How to retain top-performing sales reps and stop bleeding money on replacementsThe harsh reality of ignoring the wants and needs of Millennial and Gen Z salespeopleA simple discovery model for understanding what drives your team, which you can utilise to drive top performance  You'll learn: Why do most sales leaders struggle to keep Millennials and Gen Z salespeople engaged—and what actually works?What’s the #1 mistake leaders make that causes top performers to leave, and how can you stop it?How can you predict whether a salesperson will stay or leave - and what can you do to keep them longer?What’s the real cost of replacing a salesperson, and how can you avoid wasting millions on unnecessary turnover?What’s the simplest way to uncover what truly motivates your sales team (beyond just “money”)?If you’re serious about scaling your sales team, retaining your top talent, and mastering modern sales leadership, this episode is a must-listen.

Building & Scaling Successful Sales Teams Sales leaders and ambitious reps, this one’s for you! In this episode of I Used to Be Crap at Sales, Mark Ackers sits down with Richard Bounds, a seasoned sales leader and fractional CRO, to unpack the biggest challenges in scaling sales teams, hiring top talent, and driving sustainable sales growth. Richard shares hard-earned lessons from over 35 years experience in sales, leading and coaching sales teams at companies such as IBM, OpenText, and Software AG. Learn why fractional sales leadership is gaining traction in the startup world and how sales leaders can make a real impact. Discover the biggest hiring mistakes sales leaders make, how to spot bad hires fast, and why company culture beats experience when building a team. We also dive into the evolution of sales leadership, from old-school “work harder” mentalities to today’s data-driven, AI-powered coaching approaches. If you’re an aspiring sales leader, Richard’s insights on avoiding first-time leadership mistakes and building a high-performing team will be game-changing.   Tune in to learn: • How to scale a sales team without ruining company culture • How fractional sales leaders accelerate growth as quickly as possible, and how Richard measures success • The biggest mistake sales leaders make when hiring • How modern sales coaching transforms performance • How AI and data are reshaping the sales landscape

In this episode of The "I Used To Be Crap At Sales" Podcast, hosted by Mark Ackers, we dive deep into the art of sales development. Our guest, Gabe Lullo, is co-founder and CEO of Alleyoop. the global leader in prospecting and outsourced sales development. Thousands of companies try to replicate what Alleyoop does, but Gabe reveals the secrets behind their unparalleled success. From delivering high-quality leads, accurate data, and scheduled meetings to helping SaaS and tech businesses scale their SDR teams effectively, Gabe shares actionable insights you can use today to supercharge your own sales team and processes. Whether you’re looking to support your team in setting up more demos, booking high-value meetings, or refining outreach strategy, this episode is a must-listen. Learn how to target the right prospects with the right messaging and ensure every single call and email hits the mark. Don’t miss this conversation packed with sales tips, prospecting strategies, and leadership advice from an expert whose company helps scale some of the world’s most successful sales development teams. If you’re in SaaS, tech, or sales leadership, this episode will transform how you approach your pipeline. Find out about our £20 memberships here:https://www.mysalescoach.com/membership-pricing (00:00) - Why Sales Development is Critical for Revenue Growth (04:30) - The Key Traits of High-Performing SDRs (08:45) - How to Find and Target the Right Prospects (12:10) - Scaling Sales Teams Without Losing Quality (16:25) - Building SDR Teams That Deliver Consistent Results (20:50) - Training SDRs to Excel at Prospecting and Outreach (24:15) - Turning SDR Meetings Into Revenue Opportunities (28:40) - Lessons for Sales Leaders on Building Elite Teams (32:10) - How Data and Technology Improve SDR Performance (36:00) - The Future of Sales Development (40:15) - Balancing Personalisation and Efficiency in Outreach (44:30) - The Role of Leadership in Building High-Performance SDR Teams (48:20) - Overcoming Common Challenges in Sales Development (52:10) - Final Tips for Scaling SDR Teams and Driving Revenue (55:00) - Key Takeaways for Sales Leaders and SDR Managers 00:00 Why Sales Development is Critical for Revenue Growth04:30 The Key Traits of High-Performing SDRs08:45 How to Find and Target the Right Prospects12:10 Scaling Sales Teams Without Losing Quality16:25 Building SDR Teams That Deliver Consistent Results20:50 Training SDRs to Excel at Prospecting and Outreach24:15 Turning SDR Meetings Into Revenue Opportunities28:40 Lessons for Sales Leaders on Building Elite Teams32:10 How Data and Technology Improve SDR Performance36:00 The Future of Sales Development40:15 Balancing Personalisation and Efficiency in Outreach44:30 The Role of Leadership in Building High-Performance SDR Teams48:20 Overcoming Common Challenges in Sales Development52:10 Final Tips for Scaling SDR Teams and Driving Revenue55:00 Key Takeaways for Sales Leaders and SDR Managers

Stepping into your first sales leadership role, or aspiring to walk the beaten path from successful sales rep to leader? It’s a whole new ballgame, and not all top-performing sales reps are cut out for the challenge. In this episode of I Used to Be Crap at Sales, Mark Ackers sits down with seasoned sales veteran Alan Clark to unpack the truths every first-time sales leader needs to hear.  Drawing on 20+ years of experience managing diverse teams at global tech giants like SAP and Sage, Alan shares candid lessons learned from his early mistakes—like why building a team of “mini-me’s” is a recipe for disaster. Learn from Alan’s wins, like leading a SaaS company to a 10x ARR exit, and his missteps along the way, such as assuming success without consistent alignment with leadership. His personal anecdotes and practical advice provide a roadmap to navigate the often rocky path to becoming an effective sales manager.   You’ll discover why empathy in leadership is essential (but doesn’t mean being soft), how to avoid hiring biases, and the importance of digging deeper in one-on-one conversations. Alan also reveals the traits that separate top individual contributors from successful sales managers, and why failing to build trust and credibility with your team can derail your career.    If you’re an aspiring sales manager, new to leadership, or looking to develop your sales coaching skills, this episode offers actionable advice to set you up for success. Learn how to navigate the pitfalls, lead with confidence, and turn failures into opportunities for growth. Don’t miss out—your leadership journey starts here!