Maximize Sales Team Ride-Alongs

Part of my job is to watch salespeople in action. You can learn a lot by observing how sellers operate. Recently, I rode with a salesperson who could not find a current customer’s office. (Awkward) Over four meetings, the same seller never set an agenda, and client interactions seemed to have no point.

Ride-alongs are an opportunity to observe, coach, and learn. Done right, they can uncover best practices and problems. 

Here’s how I get the most out of these experiences:

1. Overview

Understand how their day is structured:

How many meetings are on the calendar? Is this a busy day? Does it reflect their usual workload? Ask, “What is a typical day for you?”

Are they taking you to their best clients or a mix of existing accounts and prospects? Is it good or bad if they seem overly familiar with the accounts?

2. Meeting Preparation and Planning

Well-prepared meetings set the tone for success.

Does the salesperson have a clear plan?

Do meetings have a purpose that provides value to the client?

Do they ask clients what they want to discuss?

Research: Are they prepared with insights, challenges, or opportunities?

3. Building Rapport

Sales is about relationships. Look at how they connect:

Are they taking time to ask about shared interests, the client’s role, or challenges?

Comfort with Coaching: Do they seem comfortable sharing their process with you, and are they open to feedback?

4. Quality of Client Interaction

How do they engage clients:

Do they ask open-ended questions (e.g., What, tell me, talk to me about) that encourage conversation?

Do they rely on closed-ended questions (e.g., Are you, can you, do you, have you, would you) and getting short answers. 

Are their questions connected, showing active listening skills, or do they jump around?

Are they restating and proving they can listen?

5. Presentation and Recommendations

Are they pouncing? (During discovery, they hear one thing they can solve and start presenting)

Is the presentation engaging? Do they check for clarity? Do they ask, “Does this make sense?” or “How does it sound?”

Are their recommendations tailored to what the client needs? 

6. Salesperson Development

Use this opportunity to understand their motivations and areas for growth:

Ask questions like:

“What did you do before joining [Company]?”

“What attracted you to this role?”

“What do you enjoy most about the job?”

“What would you like to be doing more of?”

Post-Ride-Along Reflection

Once the day is done, reflect and provide feedback:

Strengths: What did they do well?

Opportunities for Improvement: Where can they grow?

Actionable Feedback: Be specific and constructive about their preparation, questioning, presentations, and rapport-building.

A well-structured ride-along doesn’t just show you how the sales team operates—it helps you understand how you can help them operate better. What’s your approach to ride-alongs? Let’s discuss in the comments!