Sales managers doing ride-alongs with their reps is commonplace in B2B sales. I’ve done it myself and recommended it to owners, GMs, and sales leaders for years. Most think of ride-alongs as a management activity—a half or full day in the field, attending sales meetings and shadowing cold calls with a rep, all while literally riding along in their vehicle.
How else do you coach or develop your salespeople? You’ve got to get out in the field to see how they’re doing, right?
Before we get into why ride-alongs can be more harmful than helpful, let’s give credit where it’s due.
The Pros of Ride-Alongs
- They build relationship.
Getting out of the office and behind the same windshield is a great way to get to know your rep better—to hear how they handle calls, what kind of music they play, what the inside of their car says about them. It’s also a chance for them to know you beyond the office title. - You hear the real voice of the customer.
Sitting in on meetings can surface valuable intel. What are prospects saying about competitors? How do they describe their frustrations? What do loyal customers say about the vendors they love? - You can sometimes help close the deal.
Decision-makers often lean in when a manager or owner is present. Your words can carry authority that affirms what the rep has already said—sometimes that’s exactly what the buyer needs to move forward.
The Cons: Why Ride-Alongs Can Backfire
- Reps don’t act the same.
No matter how comfortable your relationship, your rep is on their best behavior when you’re in the car. They manage time more rigidly, ask “perfect” questions, and carry more stress. That anxiety makes it hard to see their real performance. - Prospects don’t act the same.
Most prospects will shift their attention to you, the authority figure. That might move the deal forward, but it doesn’t build your rep’s confidence or skill. - They’ll imitate you—and it won’t work.
If you sell with charisma or deep technical knowledge, your rep might try to replicate that. But they’re not you. Modeling an inconsistent sales approach can stunt their growth instead of empowering it.
So What Should You Do Instead?
I’m not suggesting you stop spending time in the field. I’m suggesting that ride-alongs—at least in the traditional sense—might not be the most effective use of that time.
Here are some higher-value ways to invest in your reps:
- Take them to lunch.
Meet midday, listen to their download from the morning, and talk through the plan for the afternoon. This informal space often leads to more honest reflection, relationship-building, and real coaching moments. - Help them close deals—strategically.
Let your team know they can bring you in when a key account or referral partner feels stuck. You can help move the ball forward while collaborating rather than taking over. - Attend networking events together.
Don’t shadow them—partner with them. Work the room independently, compare notes afterward, and see who booked more follow-ups. You’ll learn about their natural style while modeling healthy professional networking.
New Tech You Can Leverage
At FP Restoration in Florida, we’re preparing to implement Rilla, a mobile tech platform similar to Otter.ai or Fathom.video—but designed for field sales.
Imagine your reps clicking a button before a drop-in or meeting, and the entire interaction—both sides of the conversation—is captured. As a manager, you could listen to an authentic exchange between your rep and a prospect, without being physically present.
That’s a potential game-changer. It eliminates the biggest flaw of ride-alongs: the observer effect. With Rilla, you can review real conversations, see what’s working, and coach precisely where needed.
Leaders like Tommy Mello at A1 Garage Door already use Rilla across their field teams. The app runs quietly from a phone in a pocket, captures both voices clearly, then automatically ends when the meeting wraps up. The AI transcribes, highlights, and even scores the session for specific coaching markers.
For me, the real magic isn’t the AI—it’s the authenticity. You finally get to hear how your reps really sound when they’re on their own.
Don’t Stop Spending Time in the Field—Just Change the Objective
Make your time with reps less about inspection and more about connection. Field time should fuel collaboration, trust, and alignment—not anxiety and performance theater.
Technology now gives us new ways to observe and coach without disrupting authenticity. Use those tools to gain better insight, then use your face time to build momentum.
Ride-alongs aren’t dead—they’re just overvalued. Stop sitting in the passenger seat pretending you’re seeing the real picture. Let technology show you what’s actually happening out there, then use your face time to build trust and momentum. That’s how you lead a sales team that grows without you riding shotgun.
Chris Nordyke
Chris Nordyke is the co-Founder and President of Floodlight Consulting Group and Floodlight Sales Partners. Chris speaks throughout the year at industry events, and conducts live workshops focused on commercial sales and ops, customer experience strategy and building enterprise value. He is also the co-Host of the Head Heart & Boots podcast, a popular restoration industry show. For more information on Floodlight’s fractional sales management solution, visit https://www.floodlightgrp.com/
Related Posts
