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.

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🔗 Connect with John Mason on LinkedIn
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🎯 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.

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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.

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👍 Like this episode?

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✅ 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:
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