Why the Best Salespeople Struggle Most When They Become Managers
Episode 27: John Mason
John Mason spent over a decade in sales, moving from SDR through to heading up a business development team — and he's been the new manager firefighting on day one, carrying a quota while figuring out the job at the same time. In this episode of I Used to be Crap at Sales, he and Mark get into what the first-time sales manager role actually is, why the skills that got you the promotion won't automatically make you good at it, and what to focus on when you don't know what to do on a Monday. If you've recently stepped into management or you're thinking about it, this one is direct and honest.
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About John Mason
John Mason has spent more than a decade in sales — SDR, AE, team leader, and eventually head of business development. He's been through the first-time manager transition himself, including the firefighting, the quota pressure, and the moments where he had no idea what he was doing. He now coaches first-time sales managers on making the shift from individual contributor to leader, and is building a structured playbook for managers navigating their first 90 days.
What we cover in this episode
- Why being a top performer is often the wrong preparation for managing a team — and the trap most first-time managers fall straight into
- How imposter syndrome doesn't go away when you get promoted — it resets at every new chapter of your career
- What the job actually requires of you emotionally, and why most people aren't warned about it before they say yes
- Why the metrics sales leaders chase most often create the wrong behaviour (John's A&E analogy makes this land)
- What to prioritise in your first weeks as a manager — and what can wait
About The I Used to be Crap at Sales Podcast
I Used to be Crap at Sales is hosted by Mark Ackers, Co-Founder of MySalesCoach. Each episode is a direct conversation with someone who has been in the sales seat — covering the specific challenges that sales leaders, AEs, and SDRs actually face: first-time management, SDR coaching, quota pressure, difficult conversations, burnout, and the parts of the job nobody puts in the job description.
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MySalesCoach
MySalesCoach matches sales teams with expert 1:1 coaches — people who've done the job, not just studied it. If anything in this episode sounds like your team, speak to us to see what consistent coaching could mean for your number.
