Remember spending entire days in the car, racing between customer meetings, trying to coach your sales team during ride-along days?
There’s a better way.
Here’s a startling stat: 75% of buyers are unimpressed by sellers’ ability to navigate their needs.
Yet buyers award business 2.5 times more often to sellers who demonstrate these skills. Source: “What Sales Winners Do Differently,” RAIN Group Center for Sales Research.
The gap is real, and limited coaching that occurs during infrequent sales ride-along days doesn’t close skill gaps fast enough.
In-person ride-alongs reveal a unique spectrum of skill gaps to enable development plans. The truth is that modern sales coaching no longer needs to be focused solely on full days in the field. Technology has opened up other powerful methods for observing your salespeople in action and gaining customer exposure that include much less time commitment.
Virtual Meeting Observation
Join customer calls across any territory without the need for travel. Your representatives need to master video facilitation tools, such as virtual whiteboards, polling, and screen sharing, to create engaging virtual experiences.
Real-Time Call Monitoring
Identify communication strengths and gaps in 15-minute blocks through call monitoring. To make this work, you need to be open with your reps about the fact that phone shadowing is part of your sales coaching practice. In return, sales managers owe their salespeople helpful feedback and role modeling based on the improvement opportunities identified through call monitoring.
Strategic In-Person Sessions
Reserve ride-along time for maximum impact. In advance of customer meetings, invest time to ensure both the salesperson and sales manager understand their roles and the objectives for the meeting.
Pre-call planning provides visibility into the salesperson’s forethought and their ability to execute strategy.
The best part? These approaches can scale across your entire team and fit into your existing schedule. Dive into my full article, “Why It’s Time to Redefine the Sales Ride-Along,” to discover more depth on this topic such as:
- The structured pre-call planning framework that transforms random meetings into high-impact interactions
- A proven debrief process that creates learning conversations instead of critiquing sessions
- How to make your salespeople look forward to coaching sessions rather than dread them
The Bottom Line
Sales coaching isn’t optional; it’s the difference between a team that consistently wins and one that struggles to close. The question isn’t whether to coach, but how to make it sustainable within the realities of your calendar.
The traditional all-day ride-along will always have its place for certain situations. But when geography, schedules, and bandwidth create barriers, modern sales leaders incorporate alternative observation methods to ensure that sales skill development is a continuous focus.
If you’re thinking “I see the value, but I still don’t have the time,” my Fractional Sales Leadership approach might be your answer. Let’s explore how your needs align with my model through an exploratory call.
You can reach me any time at (404) 271-6767 or [email protected], or book a call through my Scheduling Tool.
I am part of a national group of Fractional Sales Leaders who collaborate to share insights like the examples shown in this article. We formed because of our shared passion to help business leaders exponentially expand their revenue.


