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

EPISODE · May 20, 2026 · 1H 4M

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

from I Used To Be Crap At Sales · host MySalesCoach.com

Episode 27: Why the Best Salespeople Struggle Most When They Become ManagersMost 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

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

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