3 Sales Leadership Mistakes That Nearly Cost Me My Career (and What I Learned)
Nov 08, 2025Every sales leader loves to talk about their wins. But the truth? I’ve learned way more from the mistakes that made me cringe years later.
These aren’t theoretical lessons — they’re scars. Real situations. Real consequences. And in my $4.99 Mini-Pod Series, I go deep on how I fixed them, what I’d do differently, and how you can avoid making the same painful (and costly) errors.
Here’s a quick preview of three of them 👇
1️⃣ Dealing With Salespeople Who Can’t Sell
I once inherited a rep who, frankly, couldn’t sell his way out of a paper bag.
I tried everything — coaching, call reviews, training, ride-alongs — nothing worked. But then I noticed something most leaders miss: a completely different skillset hiding in plain sight.
That single observation turned a “train wreck” into one of the most successful people I’ve ever managed.
➡️ In the Mini-Pod, I’ll walk you through how I spotted their hidden strengths and what I did next that changed both our careers forever.
2️⃣ The Quota-Missing Rep I Couldn’t Fire
Imagine a rep missing quota for six months straight — and you can’t fire them.
Yep, that happened. HR stopped me cold and asked one brutal question that exposed a rookie mistake I never saw coming.
Turns out, I was missing something so basic, so obvious, that it completely tied my hands.
➡️ In the Mini-Pod, I break down exactly what went wrong, how to prevent this from ever happening to you, and why this mistake nearly got me fired.
3️⃣ The Sales Leader Who Got Drunk at a Company Event
I used to think being “the life of the party” was part of leading sales. Shots at midnight. Inside jokes. Late nights.
Then one night, a line got crossed — and it hit me how quickly a “fun” culture can turn into a liability.
I learned the hard way that there’s a razor-thin line between having fun and being the fun.
➡️ In the Mini-Pod, I share the simple rule that protects your reputation, your team, and your career — every single time.
🎧 Want the Full Story?
I go deeper into these three painful (and career-defining) mistakes — and the exact learning lessons you can take and apply immediately — in my Mini-Pod Series: “Sales Leadership Mistakes You Can’t Afford to Make.”
It’s only $4.99, and it might save you from making a $499,000 mistake someday.