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Best Practices for Coaching Sales Reps in the Field

By Ellen Knowles | March 17, 2025

Effective sales coaching is a vital component of any successful sales team, especially in complex industries such as post-acute care, home medical equipment (HME), and infusion sales. In these fields, sales representatives must build strong referral relationships and keep up with ever-evolving industry trends.

Sales managers play a crucial role in guiding their teams toward sustained success. Let’s explore best practices for coaching sales reps in the field, how to structure coaching sessions, and how to use technology to create actionable conversations with reps.

The Sales Manager’s Role as a Coach

Sales managers are much more than supervisors – they are mentors, strategists, and motivators. As a coach, a manager’s primary role is to provide consistent, actionable feedback that helps sales reps refine their sales techniques, improve their messaging, and develop stronger relationships with providers and partners. In coaching sessions, managers should focus on key areas such as effective sales messaging, cultivating long-term relationships with referral sources, and understanding market intelligence. Managers should also encourage reps to leverage market insights and their CRM notes for strategic decision-making while staying informed on competitors and industry trends.

Through structured coaching, sales managers can ensure that reps not only stay aligned with business goals but also continuously improve their performance. In this way, coaching becomes a tool for both personal and professional growth.

The Importance of Ride-Alongs

Ride-alongs in the field are one of the most effective ways to observe a sales rep’s performance, provide real-time feedback, and help them develop new skills. By accompanying a rep on sales meetings, managers can directly assess the following areas:

  • How they engage with referral sources such as physicians and hospital discharge planners
  • How they handle objections
  • How well they communicate the value of a potential partnership through data on metrics like readmission rates and post-acute utilization rates

Before heading out on a ride-along, it’s important to set clear objectives for the session. These objectives may include assessing how the rep handles objections, builds rapport, or positions value. Managers should align these goals with the specific areas of improvement they want to target during the session. Prior to the ride-along, reviewing relevant partner data within a CRM system can provide additional context, allowing managers and reps to better understand the referral source’s needs and opportunities to position value.

During the ride-along, it’s important that the sales rep takes the lead in the conversation. This allows managers to observe how the rep handles different aspects of the sales process without stepping in too much. The manager’s role is to observe and take notes on both the rep’s strengths and areas for improvement. Real-time feedback can be invaluable, but it’s essential to strike a balance between offering advice and allowing the rep to manage the situation on their own.

After the ride-along, the manager should immediately provide structured feedback. This can include highlighting what went well, where there are opportunities for improvement, and what the next steps should be. Providing documented feedback while the experience is fresh in both parties’ minds ensures that it’s relevant, actionable, and doesn’t get lost in translation.

Creating Consistency in Coaching

While effective coaching can take many forms, it’s important to maintain a consistent timeline. Sales coaching shouldn’t be a one-time event but an ongoing process. Managers should hold regular check-ins with their team members – either weekly or biweekly depending on the size of your organization – to discuss performance and identify areas for improvement. These check-ins provide an opportunity for reps to discuss any challenges they are facing and for managers to offer guidance or resources to help overcome those challenges while developing a coaching culture.

Monthly deep-dive coaching sessions can focus more on skill-building, performance trends, and refining strategies, while quarterly ride-alongs offer a hands-on approach to coaching. Ad hoc coaching may also be necessary when a rep faces a specific challenge that requires immediate attention.

By maintaining a structured rhythm to coaching, sales managers can ensure that they’re providing continuous support to all of their reps. This approach helps sales reps stay on track with their goals, identify areas for improvement, and fine-tune their sales techniques over time.

Tailoring Coaching to Individual Needs

Not all sales reps need the same type of coaching. It’s essential to tailor coaching efforts based on individual performance levels to maximize their effectiveness. Newer reps, especially in their first 90-180 days, typically need more hands-on coaching that focuses on foundational sales messaging and early-stage skill development that won’t overwhelm them.

Reps who are more experienced but still not performing at their peak will benefit from more targeted coaching that helps them refine their current strategies and identify specific areas for improvement. Reps who are significantly underperforming may require more intensive coaching with a clear, documented improvement plan that addresses their specific weaknesses. High-performing reps still need coaching too, but their focus shifts more toward scaling best practices, fine-tuning advanced strategies, and preparing them for leadership roles within the team.

By prioritizing coaching efforts based on the individual needs of each rep, managers can ensure that every team member receives the support they need to succeed.

Delivering Actionable and Structured Feedback

Coaching feedback should always be structured and actionable. At the beginning of each coaching session or ride-along, managers should review the session’s objectives and highlight any recent successes. It’s important to acknowledge specific wins to reinforce positive behaviors, but equally critical to identify areas where improvement is needed.

Once the coaching session has been completed and areas for growth have been outlined, managers should work with the rep to create an action plan that includes clear, measurable steps to address the challenges identified. Finally, managers should schedule a follow-up meeting to track progress, celebrate improvements, and provide further guidance as needed.

Using structured coaching forms within a CRM system can streamline this process by documenting feedback in real-time and making it easier to track a rep’s progress over time. This ensures that no feedback is lost and that every coaching session builds upon the last.

Utilizing Technology to Enhance Coaching

Leveraging technology can significantly enhance the coaching process for both parties. A CRM system with integrated coaching features allows managers to document feedback during ride-alongs, track reps’ progress, and share important insights with the rest of the team. By using CRM tools to centralize coaching data, sales managers can ensure that their coaching efforts are organized, measurable, and transparent.

For example, Trella Health’s CRM Coaching feature allows managers to seamlessly integrate coaching into their daily workflow. Reps can access customizable forms in the field, track their own development, and see how their performance aligns with key metrics – all within the Trella Health CRM mobile app. These tools also help streamline the feedback process, ensuring that each rep receives timely and relevant guidance to support their growth.

Building a Coaching Culture

Ultimately, the most successful sales teams are those that embrace a culture of coaching and being coached. Managers should encourage peer-to-peer coaching and open feedback loops, where reps feel comfortable seeking guidance from one another. By using sales data and CRM insights, managers can drive coaching discussions and track progress, ensuring that coaching remains a collaborative and ongoing process. Recognizing and celebrating the wins that come from effective coaching further reinforces a positive feedback loop, encouraging reps to engage with the coaching process and improve continuously.

When coaching becomes embedded in a company’s culture, it empowers reps to thrive, build stronger relationships, and ultimately drive long-term business success.

Coaching as a Competitive Advantage

Sales coaching isn’t just a nice-to-have – it’s a competitive advantage. By investing in structured coaching programs, leveraging CRM tools, and focusing on continuous development, sales teams become more strategic, efficient, and effective. A strong coaching culture helps reps hone their skills, build better relationships, and ultimately drive greater sales success. When managers prioritize coaching, they’re not just improving individual performance, they’re fostering a team-oriented approach that fuels long-term growth and success.

Great sales coaching starts with real-time, in-the-field insights. Learn more about Trella Health Coaching by requesting a demo today.

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Ellen Knowles

As a results-driven marketing enthusiast with a focus on Healthcare IT and SaaS-based business, Ellen helps achieve strategic goals for market growth, product adoption, and customer success as a Product Marketing Manager at Trella Health. Ellen spent time at Georgia Military College before moving to Atlanta to start her career in sales, but quickly found her passion in marketing and dedicated the last four+ years to growing health IT brands and business in the hospital and ambulatory. At Trella Health, she's able to continue her passion for innovation and meaningful results.

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About the Author:

Ellen Knowles, Product Marketing Manager

As a results-driven marketing enthusiast with a focus on Healthcare IT and SaaS-based business, Ellen helps achieve strategic goals for market growth, product adoption, and customer success as a Product Marketing Manager at Trella Health. Ellen spent time at Georgia Military College before moving to Atlanta to start her career in sales, but quickly found her passion in marketing and dedicated the last four+ years to growing health IT brands and business in the hospital and ambulatory. At Trella Health, she's able to continue her passion for innovation and meaningful results.