How to
Coaching a rep who is behind on number.
A rep behind on number has one of four problems: not enough pipeline, the wrong pipeline, deals stalling at a specific stage, or deals dying late. Each needs a different conversation and the diagnosis is in their own numbers.
Diagnose before coaching.
Compare their pipeline coverage, their win rate, their median time per stage and where their losses cluster against the team.
One of those four will look different. That is the problem, and the other three conversations are wasted.
Not enough pipeline.
Coverage below the team. This is an activity and targeting conversation, and it is the only one of the four where more effort is the answer.
The wrong pipeline.
Coverage fine, win rate low, losses early. They are opening deals that were never going to close. Qualification, not effort.
Stalling at a stage.
Median time in one stage well above the team. Something specific is not happening there, usually a step they are not asking for. Highly fixable and often the fastest win.
Dying late.
Losses clustered in the last stages. Usually single threading or a missing stakeholder, and it is the most expensive pattern because the time is already spent.
Kaypo surfaces the pattern per rep rather than the ranking, so the one to one starts from what keeps happening rather than from the number.
Questions
How do you coach an underperforming sales rep?
Diagnose first. Compare their coverage, win rate, stage duration and where losses cluster against the team. One will stand out, and the other three conversations are wasted effort.
What causes a rep to miss quota?
Usually one of four: not enough pipeline, poorly qualified pipeline, deals stalling at a specific stage, or deals dying late from single threading.
It arrives in Slack
Every morning, each rep gets one message naming the deals on their own book that moved overnight, biggest mover first, with the reason beside each number and the deals that have gone quiet underneath.
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Related reading
When a rep forecast does not match their pipeline
Systematically low commit against a healthy book, and the opposite. How to tell either apart from genuine caution.
A sales one to one that is not a status update
Four sections, thirty minutes, and none of it spent reading the CRM aloud.
How to run a pipeline review that is not a status update
Most pipeline reviews are a rep reading their own CRM aloud. What to ask instead, and how to prepare so the meeting makes decisions.
Which sales metrics are worth reporting
The test for any metric is whether a different value changes a decision. Most reported sales metrics fail it.
Reviewed September 20, 2026 against the product as it behaves today.