Coaching to Build Rep Confidence and Better Engage Buyers

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In enablement, maintaining buyer engagement is key to strong customer relationships that yield positive business outcomes. Maintaining these relationships, however, relies on the confidence of reps in buyer interactions. Coaching rep confidence is one way to make sure that relationships with buyers are strong and supported.

Coaching improves rep confidence through practice, empowerment, and support. When reps feel confident in their skills, they are more likely to engage buyers effectively and land sales. Here are a few key ways to approach coaching rep confidence for better buyer engagement.

Coach the Controllable Aspects of Sales

When refining its approach to cultivating buyer engagement, it is important for a company to consider the individuals responsible for maintaining this interest. Sellers are the most direct link to buyers, so investing time and resources into coaching sellers is key to supporting buyer engagement.

One of the most important aspects to consider while refining buyer engagement is levels of control. While it is impossible to control a buyer’s ultimate decision, coaching a seller’s customer interaction skills can guarantee a seamless experience.

“You can’t force a customer to sign an order with you, but you can definitely control all the experience that you, your reps, and your org are going to share with them until that point. So, when they make a decision they know what it feels like to partner with you,” said Celine Grey, sales enablement director at

Influencing the direction of customer interactions is a coachable skill. Understanding the best way to coach this skill in sellers, however, can be determined based on a seller’s background. The way in which coaching is framed for each individual rep is controllable and should be leveraged to maximize learning outcomes.

Taking the time to meet with sellers and discuss career history, goals, struggles, and successes can strengthen the seller-coach relationship and help personalize coaching sessions. In turn, these coaching sessions will produce more substantial relationships between reps and customers.

“First, I want to know my people. I want to have an idea of how they are thinking and how they like to learn from us. [Then], it all depends on the definition we put on coaching,” said Alina Spatariu, sales enablement manager at RingCentral.

Coaching will look different for every seller, and utilizing knowledge of a seller’s previous experiences to tailor coaching can help situate them in a better position for learning. From this, sellers can be better equipped to engage with buyers successfully and close sales.

Provide Realistic Practice Opportunities

Coaching sellers on buyer engagement effectively is dependent on practice. Providing sellers with frequent, reality-based opportunities to practice new and existing skills will ensure they arrive at coaching sessions with contextual practice and specific goals in mind. These realistic experiences will then translate to improved buyer engagement as sellers replicate their practiced skills in real customer interactions.

One way for sellers to practice realistic sales scenarios is through role-playing exercises.

“We do Real Plays, which are scenarios that we write based on existing deals that we won with very specific qualifications,” said Grey.

Activities like these mimic actual sales situations, giving reps an opportunity to utilize new skills and exercise best practices in a safe, constructive environment. As reps gain experience with new skills, their coaches are better equipped to tailor development to their individual needs. Reflecting on these exercises can be a great way to personalize and substantiate coaching sessions.

“[Letting sellers practice] gives your frontline managers the ability to have a coaching moment,” said Chris Book, global head of enablement at commercetools.

Mock sales calls are another exercise that can provide reps with realistic practice opportunities, as they are usually based on real sales scenarios that have occurred in interactions with buyers. By practicing in a mock version of a real scenario, sellers can feel the pressure and decision-making responsibilities of a real call without the stakes.

“Make practice as close to the real sales cycle as you can,” said Book.

Mock calls give sellers the opportunity to refine their skills and receive feedback without the pressure of a real buyer interaction, making the process more constructive and less threatening.

“[Mock sales calls] act as a library of safe environments that you can use as real coaching moments,” said Book.

Regardless of the exercise used, taking a realistic approach to practice opportunities is the best way for sellers to develop their skills. Confidence in practice translates to confidence in sales; a confident seller will keep buyers engaged and see positive outcomes in sales.

Empower Reps to Stay Resilient

Realistic learning opportunities provide practical experience with new skills, which means mistakes will be made as sellers learn. This learning format requires a higher level of resilience from sellers and more dedicated support from managers. However, the positive outcomes of realistic, practice-based learning are evident in sellers’ confidence when fostering buyer engagement.

Grey compares this style of learning to making pancakes. When a seller seizes an opportunity to use a new skill, their first attempt may not be perfect. A resilient mindset keeps sellers safe while they are learning and cultivates an overall environment of trust and community for the sales team.

“When you make pancakes, the first one is often not great, but you continue because you want to eat the second and third and fourth pancakes,” said Grey. “We acknowledge the fact that someone has taken the time to address something that is business-critical. You have to have a lot of vulnerability and trust, because you present something that is in no way perfect.”

Learning takes patience and determination. In this way, learning a new skill can be much more like running a marathon than a sprint.

“Start with one competency and go super deep with it until you’ve nailed it. I run marathons, and there’s nothing I hate more than running. It’s the achievement of the finish line and the process that goes into it. We’ve got to get reps used to that as well. The only way I fell in love with running was running more,” said Aaron Evans, co-founder and head of training and enablement for Flow State.

Coaching sellers to improve their buyer engagement skills is also teaching sellers to be resilient in their efforts. Not every interaction will be perfect, but encouraging reps to commit to the learning process will result in long-term results in the form of buyer engagement and closed sales.

Maintaining buyer engagement is an important part of the sales process. Pairing training sessions with specific coaching approaches is a great way to encourage reps to build their confidence in interacting with buyers and maintain the important sales relationships they forge throughout the sales process. By identifying what is controllable, training with realistic practice opportunities and coaching moments, and empowering sellers to be resilient in their learning, enablement can help sellers maintain long-term, successful buyer engagement.

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