Why Seasoned Salespeople randomly stop Succeeding: The Three Buckets That Tell the Whole Story
When a seasoned salesperson isn’t achieving their numbers, we tend to overcomplicate the diagnosis. We talk about market conditions, team performance, inventory, pricing, or even “bad luck.”
But after nearly two decades in sports — and apologies to those who have worked with me who will be hearing this for the millionth time and thank you to the mentors who have engrained this in me — I’ve found almost every underperforming rep falls into one of three buckets.
And if you can identify which bucket(s) they’re in, you can fix it fast.
1. Not Enough Touchpoints
This one’s the most common — and the easiest to measure.
Sales is a contact sport. If you’re not getting on the phone, sending emails, following up, or connecting on LinkedIn, you’re simply not in the game.
I’ve seen talented reps with great energy and people skills fail because they weren’t consistently creating opportunities.
No matter how strong your pitch is, you can’t close conversations that never happen.
If the activity is low, the outcome will be too. The fix? Structure. Track touches, set daily targets, and hold yourself accountable to the rhythm that builds momentum.
2. Meeting With the Wrong People
Even the best reps waste time chasing the wrong leads.
You can have 100 meetings a month, but if 80 of them are with folks who can’t buy, won’t buy, or don’t have influence — your numbers will still look flat.
The key is qualification.
Who are the real decision-makers?
What’s their budget authority?
Do they have a reason to act now?
Great salespeople spend more time talking to people who can say yes — and less time trying to convince those who never will.
3. “A Hole in Their Swing”
Here’s the toughest one to fix — and the one most managers overlook.
Sometimes, the rep has plenty of activity and good meetings… but their presentation just isn’t landing. They’re missing something in how they tell the story, build value, or handle objections.
That’s what I call a hole in their swing.
It doesn’t mean they can’t sell — it means they need reps in the batting cage. Roleplay calls. Refine scripts. Practice closing questions. The same way a hitter studies film, a sales rep should be reviewing their conversations.
The good news? With coaching and repetition, this is fixable — fast.
Final Thought
When a salesperson struggles, it’s rarely a mystery. It’s usually one of these three:
Not enough touchpoints.
Talking to the wrong people.
A hole in their swing.
Diagnose it quickly, coach it directly, and you’ll see results change just as fast.
Because in sales — just like in sports — you don’t need to reinvent the playbook, you just need to execute the fundamentals.
At GameDay Advising, we help teams train and coach their reps to hit more consistently — from daily structure to sales presentation mastery. Click here to schedule a 30 minute conversation about how we can help you prepare.
