Ride-Along Coaching: It’s Not What You Think

It’s incredibly frustrating. Ride-along coaching ought to be a powerful tool at the disposal of every leader in a sales-based organization today. But, many still don’t use it properly and their sellers—and sales—suffer the consequences.

I’ve been helping businesses troubleshoot their sales training strategies for over two decades and here’s what I see with painful consistency in the marketplace today: the biggest impediment to success with ride-along coaching doesn’t rest with the sellers…it rests solely with the coach!

So, why does this keep happening?

It’s because leaders, far too often, have the wrong assumptions about why this kind of coaching is done, when it’s necessary, and how to apply what gets learned from the experience.

You must get better at ride-along coaching if you want your team to become the top-ranked sellers you know they’re capable of becoming. Here are six ways you get there.

1. Be clear why this is done.

Ride-along coaching isn’t designed to save every sale (with the presumption that every sale is somehow in danger), nor is it meant to turn a manager into a closing hero. And, it’s not designed with the premise of fixing sales problems as they’re occurring. To habitually do any of those on a ride-along is akin to being a helicopter manager. That just has the net effect of demoralizing your staff and confusing your customer. Instead, recognize the real purpose of this exercise: it’s for you to listen and observe now…and for your seller to learn and apply the lessons later.

2. Plan ahead and signal.

It’s incredibly awkward—for both your seller and buyer—if you just show up unannounced during a sales meeting. Never do ride-alongs impulsively. Plan ahead with intent. Both the seller and the customer need to know when you’re coming and why. That must be communicated at the moment the meeting is scheduled. This also entails doing some pre-coaching with the seller. Spend some time with them defining what they hope to achieve from the upcoming sales meeting. That way, you can later assess their performance in meeting their goal.

3. Pinch-hit only if necessary. 

By all means, if you’re on a ride-along and witness a deal that’s clearly in the process of falling apart, do your part to help get things back on track. However, recognize this is reserved only for emergency cases. And even when you need to do this, you must turn control of the sale back over to the seller as quickly as possible. That’s a far cry from behavior I’ve seen where the ride-along coach oversteps beyond troubleshooting mode and, instead, behaves as though they just tied on a superhero cape…ready to swoop-in and heroically “save the day.”

4. Adapt to how things are now.

Next, recognize that ride-along coaching has changed in its application. In pre-pandemic times, a ride-along entailed two kinds of activities. Either you sat-in on a phone call in your seller’s office or you got in the car with them and went to visit a client together. These days, since there are far fewer on-site visits happening, a third option has emerged: online ride-alongs conducted by group video calls (e.g., Zoom or Skype). Using this new option means you gain an important new tool: the entire meeting with the seller can be recorded and analyzed right after the meeting wraps up.

5. Walk a fine line.

The Ancient Greeks had a saying: we’re given two ears and one mouth for a reason. If the purpose of a ride-along coaching session is for you to listen and observe, then make sure your actions match your intentions. Participate in conversations with the buyer, but without taking control of the conversation. Your job is to help the sale, not to make the sale. Never usurp the seller’s power or sense of agency. Your job is to collect evidence, later share what you have found, and troubleshoot accordingly.

6. Debrief right away.

Once the ride-along is over, it’s a mistake to wait a while before debriefing your seller. You must do it the same day while the memory of the experience is still fresh for both of you. That’s the only way you can relate what you observed in real-time and show the seller how they met—or didn’t meet—expectations that were set out in your pre-coaching session together. Similarly, in those rare instances where you need to pinch-hit, you must use the debrief to immediately share what went wrong and how you helped to fix things.

Work hard at mastering your ride-along coaching skills. In doing so, you set a powerful example for your sellers about the importance of life-long learning as a sales pro. As a result, you’ll be far more effective as a leader and your team will achieve a new level of sales excellence.