Your Team Knows Everything. Why Is Selling Still Hard?
You have a sales team of experts.
They know the offering by heart.
They can answer any technical question.
They can explain every feature, every option, every difference with competitors.
And yet, selling remains difficult.
So you do what most sales leaders do when competence is not translating into results.
You organize trainings.
You refine the pitch.
You invest in enablement.
You support the team as much as you can.
Still, something does not move.
At some point, a familiar internal dialogue starts.
Maybe they do not know how to sell.
Maybe they are not built for it.
Maybe you are missing something as a leader.
You consider options.
Changing a few team members.
Finding a new training program.
Launching a team-building initiative.
Adding incentives.
Adjusting targets.
But none of these feels like a clean diagnosis.
So the system does what systems often do under uncertainty.
It looks for the lever that produces short-term relief.
Pressure increases.
Deal involvement increases.
Managers step in to “save” critical opportunities because it works, at least temporarily.
And over time, the symptoms become harder to ignore:
🚩 rising acquisition costs
🚩 lower conversion rates
🚩 longer sales cycles
🚩 procurement tunnels
🚩 price pushback
🚩 unstable pipeline
🚩 eroded margins
🚩 weaker relationships
If this is familiar, it is not an isolated problem.
It is a recurring pattern in organizations where sales competence is high, but decision outcomes are inconsistent.
The mistake is usually in the question being asked.
Most teams ask: how do we sell more?
A more useful question is: how do we become better salespeople?
Pause on that for a moment.
Independently from quota, conversion rates, and commission plans, what makes a salesperson better?
A good way to clarify it is to leave the seller’s world for a second and enter the buyer’s world.
Think about the last time you bought something from a salesperson.
Did you buy because of the product?
Because of the brand?
Or because of the way the salesperson helped you decide?
More importantly:
Do you believe you were sold to, or do you believe you decided?
Most buyers experience it as a decision they made.
And that detail matters, because the buyer’s decision does something most sales dashboards fail to acknowledge.
When a buyer decides, they are also deciding whether the salesperson “closed” the deal.
In the same moment, they define the salesperson’s sales performance.
Sales performance is not only produced by selling activity.
It is produced by buying decisions.
And buying performance is not measured by excitement or persuasion.
It is measured by the quality of the decision.
That creates a different way to think about selling:
- quota and conversion rate describe the seller, but they say little about the buyer’s decision quality
- buying performance is the buyer’s ability to make a sound decision in context
- the primary role of a salesperson is to help the buyer make the best possible decision
- learning in a sales conversation means exploring what truly matters to the buyer beyond the product
- over time, the salesperson’s learning performance becomes the salesperson’s sales performance
This is where many expert teams get stuck.
They are trained to be right.
They are not trained to improve the customer’s decision quality.
So they do what they know how to do:
explain, answer, justify, convince.
And buyers do what buyers do under uncertainty:
delay, compare, push back on price, hide behind procurement, keep options open.
From the outside, it looks like a selling problem.
In reality, it is often a decision-quality problem.
Not on the seller side only.
On the buyer side.
And that shifts the practical question again.
Not: what should my salespeople say differently?
But: what should they learn to see, to hear, and to test so that the customer can decide with higher confidence?
That is the path from expertise to effectiveness.
Not by adding more pressure.
Not by adding more tools.
But by raising the quality of decisions inside the conversation.