Why It’s Time to Redefine the “Sales Ride-Along”
Tom Morgan, CSL-Sales Strategist
Outsourced/Fractional VP of Sales Consultant, helping businesses realize their sales potential
The success of your business depends on how well you engage with your customers. If you want to ensure that your sales team is delivering the best customer experience possible, investing notable time in sales coaching is essential.
For decades, B2B sales coaching has relied on the traditional "ride-along" - a sales leader spending an entire day in the car with a rep, attending back-to-back customer meetings. While valuable, this approach is time-intensive, geographically limited, and increasingly misaligned with how modern selling actually happens.
The good news? Technology has transformed what's possible. Today's sales leaders can coach more effectively, more frequently, and with greater flexibility than ever before.
Key Takeaways
Modern Day "Sales Ride-Along" Methods
What we used to only accomplish by getting in the car for a full day with a salesperson can now be achieved in multiple ways - and in far less time!
The key for sales managers is to routinely invest time interacting with their sellers in various live customer settings. This enables you to identify where additional coaching is needed, hear the obstacles salespeople are navigating firsthand, and recognize when front-line reps need stronger product offerings or additional sales tools to compete effectively.
As I explained in a previous article, “Reveal Your Sales Skill Gaps with the Customer Journey”, these are also ideal opportunities to identify new areas to feed into your sellers' individual development plans.
Let's examine the different ways we can partner with our salespeople in their day-to-day selling activities.
In-Person Customer Meetings
While the sales ride-along term is dated, the benefits of accompanying your salespeople in in-person customer settings remain a constructive development activity.
It's a productive method to help identify and bridge skill gaps, improve customer engagement, and give you real-time insights into how customers perceive both your company and the sales reps you have assigned to their accounts.
It's also a great opportunity to validate your sales messaging and demonstrate to both customers and your salespeople that you're investing in their success.
The in-person setting allows you to observe body language, rapport-building techniques, and how your sellers navigate unexpected challenges in real-time.
Virtual Customer Meetings
In recent years, the scales have tipped in many sales environments, with more prospect and customer interaction occurring through video interface than in-person.
This opens up an entirely new opportunity to engage with your salespeople in their live customer settings. Not only can you bring the same value described for in-person meetings, but most sellers still need help evolving into strong video call facilitators.
Effective virtual selling requires mastery of online tools that create engagement such as virtual whiteboard activities, polling, chat, and screen sharing. As their sales leader, you need to pave the way for teaching sellers how to run effective virtual meetings.
Done right, video call discussions can become even more productive than in-person settings. Virtual meetings offer easier scheduling, the ability to join meetings across different territories without travel time, and more frequent coaching opportunities.
Telesales Activity
No matter the sales role, all salespeople need to be strong performers when it comes to phone communication. This includes prospecting activity, nurturing relationships, negotiating to close a deal, and handling crucial conversations when things get off track.
With today's technology, there are unobtrusive methods to tie into your seller's calls to observe them in real-time. While a recorded call can work, you should ensure it's a random sample of a conversation and not a cherry-picked "great call" selected by your salesperson.
It's important to be transparent with your reps that call monitoring is part of your sales coaching practice. In exchange, sales managers owe their salespeople helpful coaching and role modeling based on the improvement opportunities identified through call monitoring.
I commonly find this to be low-hanging fruit to drive sales improvement. Moreover, it can be easily worked into your schedule in small block segments, making it one of the most time-efficient coaching methods available.
Maximizing Sales Ride-Along Time
To maximize in-person, video, or phone customer meeting ride-alongs, the salesperson must prepare in advance.
This ensures both the seller and sales manager understand their roles and the objectives for the meeting so they can engage cohesively. Some forethought is needed to create a high-value meeting experience that progresses the sales process while building relationship depth.
Did you know 75% of buyers are unimpressed by sellers' ability to navigate their concerns, needs, and wants?
And that buyers awarded business 2.5 times more often to sellers who demonstrated these skills?
SOURCE: "What Sales Winners Do Differently", RAIN Group Center for Sales Research
Help your salespeople become exceptional by providing them with sales tools to organize their approach.
For example, a single-page Sales Call Planning Guide can help sellers organize pre-call planning activities, capture key points during the customer meeting, and remain focused on forming clear next steps.
When partnering with salespeople for customer meetings, it works well for them to populate the guide and share it ahead of time. This way, you can quickly sync on details when you connect for your final prep conversation.
The Debrief: Where Real Learning Happens
After the meeting is done, the success of your sales ride-along time investment lies in your debrief process. The goal is to create a learning conversation, not an evaluation session.
Key Points to Cover During Meeting Ride-Along Debrief:
Start with their perspective. Ask your rep to walk you through what they felt went well. This builds confidence and helps you understand their self-awareness level.
Assess objective achievement. Did they achieve the objectives outlined in their call plan? If not, what got in the way?
Encourage self-reflection. Ask the rep to identify one or two things they felt could have gone better. This develops their critical thinking and makes them an active participant in their own development.
Share your insights carefully. If your perception of the meeting was different, help your rep learn through your insights without undermining their confidence. Use specific examples and tie feedback to customer reactions or outcomes.
Focus forward. Recap next steps to progress the customer relationship and coach as necessary to optimize execution.
It's important your salespeople don't feel scrutiny during your ride-along time with them. You are there to help them achieve better results.
Ultimately, you want your sellers to see ride-alongs as an opportunity they look forward to, not something they dread.
Creating Time For "Sales Ride-Alongs" Pays Off Ten-Fold
If you grasp the value of investing more time coaching your salespeople but simply don't have the time, the business case is evident to seek out a solution.
Fractional Sales Leadership can provide experienced coaching support without the commitment of a full-time hire. This approach allows you to scale coaching efforts, bring in specialized expertise, and ensure your team receives consistent development while you focus on strategic priorities.
To learn more about how I can help, check out my article called, “Can Fractional Sales Leadership Help Me Get Ahead?”.
Ready to transform your sales coaching approach?
Whether you need help developing virtual selling capabilities, structuring your coaching process, or exploring fractional sales leadership options, I'm here to help your team achieve better results.
You may reach me at 978-996-6030 or tmorgan@salesxceleration.com.
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I am part of a national group of Senior 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.
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