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AI & Sales

Pain points in sales: coaching

March 18, 2026Vilma Rinkinen

20 percent of salespeople deliver 80 percent of the results. Why can't the rest get there?

Sales skills and coaching is the third most common challenge in Finnish B2B sales.

Sales skills and coaching collected 356 mentions in Revial's study, making it the third most common sales challenge in the dataset. Manual work is a time problem. Data management is a visibility problem. The uneven distribution of skills is a leadership problem.

Every team has the same structure, where a few salespeople produce the majority of results. The rest are trying to figure out how they do it. This structure is too often treated as a law of nature that must be accepted. But it is not. It is the consequence of never having broken down, documented and transferred the best performers' methods to others.

Skills live in the wrong place

The best salesperson knows when a customer is ready to move forward. They hear the hesitation behind the question before it is spoken aloud. They know how to structure a meeting so that the customer themselves arrives at the conclusion the salesperson was aiming for from the start. They ask more than they tell, listen more than they speak. This is not a personality trait. It is a learned structure that has developed through repetition and feedback.

The problem, of course, is that this structure lives inside that salesperson's head. It has not been written down anywhere, it has not been taught to anyone and it does not transfer anywhere when the salesperson leaves or moves to a different role. The organization rebuilds its capabilities with every hiring round because it has never learned to transfer them internally.

Why coaching doesn't stick

Sales coaching in most organizations is a one-off event. A kickoff, a training day or a meeting where the team reviews how they should be selling. Strategy is emphasized and yet the playbook is forgotten the moment daily work resumes. 84 percent of sales training content is forgotten within three months. The reason is simple: knowledge does not stick without repetition, and repetition requires that learning is embedded in daily work rather than separated from it.

A leader's time is limited. They cannot sit in on every meeting or hear how the salesperson actually performs in front of a customer. Feedback is given during pipeline reviews or weekly meetings, meaning after the moment for learning has already passed, based on information that is assumed rather than observed. The salesperson is told what they should have done differently in a deal that was lost three weeks ago.

Sales leaders spend an average of 9 percent of their time coaching salespeople. Research shows that systematic, day-to-day coaching improves sales results by 19 percent and significantly shortens ramp-up time for new salespeople.

Feedback at the wrong moment is almost the same as no feedback

Learning happens close to doing. When a salesperson receives feedback after a meeting on the same day, they can connect it to what happened in that meeting. The context is alive in their mind, the feeling is still there and change is possible. When feedback comes a week or a month later, the context has faded and the connection to the experience is broken. Information transfers, but skill does not.

There is a second problem tied to this. A leader gives feedback based on what the salesperson tells them about the meeting, not based on what actually happened in the meeting. These are two different things. The salesperson shares an interpretation, not the interaction. They emphasize what they remember or believe was significant. The details where the process actually breaks down go unmentioned, often because the salesperson themselves does not recognize them.

The most advanced sales organizations have solved the coaching problem by changing one thing: making interactions visible. When leadership can hear how a top performer handles an objection, which questions they use to open discovery and how they guide the meeting toward a decision, that capability can be described. Described capability can be taught. Taught capability can be repeated.

Your best salesperson knows something the others do not. Until now, that knowledge has walked out with them every time a meeting ends. The solution is not to ask them to share more. The solution is to make their approach visible, recordable and transferable. Leadership sees where the process works and where it breaks down. The salesperson gets feedback the same day. The one person who used to carry the rest becomes a model that everyone can follow.

Next in the series: Why does technology become a challenge rather than a relief for so many organizations?

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