It's Bigger Than Your People
I've been thinking a lot about why some sales teams thrive while others just... don't.
After 20+ years in the field, first as a seller who won every award you could win, then as a consultant, and finally as a C-level exec trying to figure out how to bottle that success… I keep seeing the same pattern.
Most mid-market B2B companies have a couple of reps who consistently crush it; veterans who just know what to do.
But why is it so hard to get anyone else to that level?
Leadership tries everything. They hire "rockstars" who promise to bring their book of business (spoiler: they rarely do). They throw training at the problem, hoping something sticks. They're exhausted and frustrated.
It's not a people problem. It's bigger than that.
The Dirty Half-Dozen
When I dig into these environments, I find the same culprits. I call them The Dirty Half-Dozen—systemic issues that make it difficult for good people to succeed.
Top performers who can't explain what makes them successful
Your veterans operate on instinct. They can't articulate what they do differently, so you can't replicate it. That knowledge walks out the door when they leave.A sales process that hasn't evolved with how buyers actually buy today
The relationship-building methods that worked 20 years ago don't resonate the same way anymore. If you haven't evolved your approach, you're losing deals to competitors who have.No real accountability culture
Without clear expectations and consistent follow-through, even your best performers start to drift. And new reps never develop the discipline required to succeed.A comp plan that rewards the wrong behaviors
Your compensation structure is teaching your team what matters. If it's misaligned with your actual goals, you're paying people to do the wrong things.People in the wrong roles
Not everyone should be hunting. Not everyone should be farming. Role confusion creates friction and frustration for everyone involved.Reps spending time on the wrong things
Without clear priorities and process, sellers waste energy on activities that feel productive but don't move deals forward.
Most successful companies still have a few bugs in the system. You can thrive without having all of this completely nailed, but at the end of the day, sustainable sales success comes from an environment that defines and supports what good looks like, and that’s a bar that just isn’t cleared very often.
How I Help
When I work with a company, I start with a 3-4 week assessment to figure out which of these issues are holding them back. No assumptions. No cookie-cutter solutions. Just diagnostic work to understand what's actually happening.
Then we do the work that actually moves the needle:
Decode what the best reps do (and why it works), then modernize it for today's buyers
Get crystal clear on who your best customers are and why they buy from you
Train the team so those methods are repeatable—not just Bob's secret sauce
Fix comp plans and leadership structures when needed
Support leadership through the messy work of culture and behavior change
The Impact
I'm passionate about this work because I've seen people thrive in the right environment. Their confidence changes. Their income changes. Their lives change.
I've also seen the opposite: talented people stuck in broken systems. They usually blame themselves for what are really organizational failures, and some walk away from sales entirely (this was almost me).
It doesn't have to be that way.
When companies get this stuff right, the results compound. Teams perform. Culture improves. Revenue grows predictably instead of erratically. And when Bob and Sally retire after 25 years of service, you can be more confident that someone can fill their road-weary shoes.
That's why I do what I do.
If you're wondering whether your sales challenges are people problems or environment problems, let's talk. Every engagement starts with an assessment—no pitch, no pressure, just a candid conversation about what's actually happening in your organization.
