How much more would your team sell if they were simply better at selling?
Better at prospecting.
Better at asking discovery questions.
Better at presenting value.
Better at closing or negotiating.
Most sales leaders would agree that improving those skills would have a huge impact on results.
In this series on sales leadership coaching, we’ve talked about different types of coaching leaders should be doing with their teams. In this article, we’re focusing on skills coaching, the kind of coaching that actually helps salespeople improve how they sell.
When sales leaders want to improve their team’s capabilities, the first solution they often reach for is training. Training can be valuable. There are plenty of good programs out there. But here’s the reality: training alone rarely transforms a sales team.
Even when the training is excellent, the impact tends to fade quickly once people return to their day-to-day routines. Without reinforcement, most of what was learned simply disappears. That’s where coaching becomes critical. Training introduces new ideas. Coaching is what turns those ideas into habits.
Many sales leaders genuinely believe they are good coaches, but when we observe them working with their team, we often see something different.
A leader joins a sales call, ride-along, or meeting with a salesperson. That part is great, but during the conversation, something happens. They take over.
They can’t help themselves. They know the product, they know the customer, and they know exactly what they would say. So they jump in and start steering the conversation. In their mind, they’re modeling the right behavior, but modeling alone doesn’t help the salesperson develop their own skills.
If improvement happened just by watching someone else perform, we’d all be experts at whatever we observe. At some point, the salesperson needs the opportunity to try the skill themselves and receive feedback on how to improve.
Another common problem shows up after the call is over. The leader waits until the meeting ends and then immediately launches into everything the salesperson should have done differently. Even if the call went well.
The leader may believe they are helping, but the experience often feels overwhelming to the salesperson. Instead of feeling supported, they feel criticized, and they stop wanting the leader to join their calls.
That’s exactly the opposite of what good skills coaching should accomplish.
The best skills coaching starts before the call ever happens. First, define what great performance actually looks like.
For example, what does a strong discovery call include? You might define things like preparing with relevant background information, setting a clear agenda, asking thoughtful discovery questions, identifying business challenges, differentiating your solution, and securing agreement on next steps. However your organization defines it, the key is to establish a clear gold standard.
Before the meeting begins, both the leader and the salesperson should agree on the objective of the call and what success looks like.
Once the gold standard is clear, the leader’s role during the call is primarily to observe. Take notes. Pay attention to how the conversation unfolds. Watch how the salesperson handles key moments. Occasionally, the leader may need to step in, but the goal is not to run the meeting. The goal is to gather insight that will help the salesperson improve.
After the call, the coaching conversation begins. A strong coach doesn’t immediately jump into critique. Instead, they invite the salesperson to evaluate the call first.
“How do you think that conversation went?”
That simple question creates reflection and self-awareness. From there, compare the call to the gold standard you defined earlier. Did the conversation accomplish what it was supposed to? Were the right questions asked? Did the salesperson clearly differentiate your solution? Often, the salesperson will recognize the gaps themselves and when they do, the lesson sticks much more effectively.
Once the gaps are identified, the next step is understanding the impact. What difference would it have made if that question had been asked? How might the conversation have changed if the next steps had been clarified more clearly?
This part of the discussion connects behavior with outcomes. It helps the salesperson see why the skill matters. From there, identify one or two things to focus on improving during the next call. When that next opportunity comes around, those improvements are top of mind. Over time, those small adjustments compound into real skill development.
One way to make skills coaching more consistent is by reviewing important sales calls using a simple evaluation framework.
At Pivotal Advisors, we often use what we call a Curbside Check-In Tool. It gives both the salesperson and the leader a structured way to review a call, identify strengths, and highlight areas for improvement. By reviewing calls this way, everyday sales conversations become powerful learning opportunities.
Sales skills rarely improve through a single training session or occasional feedback. They improve through repetition, reflection, and consistent coaching.
When leaders clearly define what good looks like, observe their team in action, and guide them toward improvement, something powerful happens.
Salespeople get better. And when salespeople get better, results follow.
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