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Conducting Effective Coaching Sessions

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In any situation, a coach has a singular goal: to prepare their team to perform at their highest potential. This remains true in enablement. Providing coaching opportunities for reps is one of the best ways to ensure continuous sales development. Coaching sessions, however, are more than just a meeting. Both the coach and the rep must approach sessions with the right mindset to get the most out of their relationship.

Effective coaching sessions require preparation, commitment, and accountability from all participants. Whether individually or in a group setting, coaching is important to provide support for reps as they continue to learn new skills in the quickly developing sales field. Here are a few tips from sales enablement professionals on how best to conduct coaching sessions.

Choose the Coaching Format that Matches the Program Goals

Coaching can take many different forms, and evaluating the unique benefits of these forms can help determine which is best fit to the goals of coaching sessions. Choosing the right coaching format is an important part of the coaching process, and can help reps feel more comfortable during sessions. Generally, coaching is either structured for a group or individual setting.

The versatility offered by different styles of coaching can help target individual goals for reps and teams alike. Using a sales enablement tool to analyze rep performance and business outcomes is a great way to identify these goals. From the data an enablement platform can provide, a coach can create specific goals for their rep and structure coaching sessions that will improve their performance.

For example, a coach working with a rep on a personal development goal may choose to meet in a one-on-one setting. One-on-one coaching allows reps to be “vulnerable and authentic,” said Dianne Kleber, vice president of sales enablement at Paradox.

Within the realm of one-on-one coaching, there are two common subsets: skill coaching and call reviews. Skill coaching focuses on providing a rep with a coach to support them in developing a specific skill. Call reviews offer a more general approach, often using a rubric to give an overview of a rep’s performance and identify areas for development.

Unlike one-on-one coaching, group coaching centers around collaboration within a team, providing opportunities for sharing ideas and peer support. A coach may choose to structure sessions in a group setting when a team is focusing on a common development goal. In a group setting, reps can learn from each other’s strengths and weaknesses through discussion, brainstorming sessions, and peer feedback.

While both structures offer unique benefits to both coaches and reps, it is important to evaluate the unique goals of each to determine which style, one-on-one or group coaching, is best suited for the session.

Personalize Coaching to the Needs of the Rep

Before meeting with reps for coaching sessions, a coach should have an in-depth understanding of their rep’s role within the team. Evan Carlton, senior manager of sales development at CircleCI, recommends that coaches shadow the reps they support.

“If you get the opportunity, do their job,” said Carlton.

Understanding the daily responsibilities of the individuals receiving coaching will help coaches tailor their approach to the unique needs of each rep, and demonstrate their commitment to the relationship.

“That way, when I do give [a rep] feedback or coach them, they’re receptive to it,” said Carlton.

Coaches should make their commitment and intentions clear to their reps to establish security in the coaching relationship. Kleber recommends addressing this directly with reps to support the coaching relationship from its beginning stages.

“I want to meet you where you are and help you get to the next place you want to be,” said Kleber.

Personalizing each session to the unique needs of the rep is essential to demonstrating dedication, and when coaches show dedication, reps are more likely to be responsive to sessions and improve upon their goals.

Establish a Foundation of Trust for the Coaching Relationship

When approaching coaching sessions, it is important for both coaches and reps to adopt the right mindset. Reps should be prepared to enter a coaching session ready to receive feedback, discuss areas for development, and be receptive to their coach’s ideas.

“You can’t be coached if you don’t want to be coached,” said Kleber.

Similarly, coaches should approach training sessions ready to give their full support to their reps. Kleber has a specific routine she practices before entering a coaching session with a rep.

“I have to give myself the space to let go of everything I was doing prior to that session,” said Kleber.

When both sides of the coach-rep relationship arrive ready to work together, a coaching session can be most productive.

“If [the rep] can have the mindset of curiosity and openness, and I am here to ask the right questions so this person really figures out on their own where they need to go, those are the best coaching sessions,” said Kleber.

Further, while commitment to the coaching process is important, the relationship between a coach and the rep they support is built on trust.

“When I’m coaching, I establish that this is a safe space and everything that we talk about remains confidential,” said Kleber.

This can look like a direct statement to the rep as demonstrated by Kleber, or an attitude-based approach as recommended by Carlton.

“I’m here to support you guys and make you the best you can be,” said Carlton.

If a rep feels safe while interacting with a coach, they are more likely to be open to accepting the feedback offered during a coaching session. This trust takes commitment and intention from both sides of the relationship, and can grow from something as simple as an open mindset.

Create an Accountability Plan

The relationship between a rep and their coach is not a one-time engagement. Coaches and reps should work together to create an accountability plan for the continued development of coached skills. Carlton likens this relationship to his experience on sports teams.

“If your coach isn’t in your face, that’s a bad thing,” said Carlton.

Accountability plans can take many different shapes, including physical reminders like images or notes, virtual tracking strategies like a shared document, or inviting another team member to serve as an accountability partner.

“[Choose] the cue that you need to put in place to remember the habit that you’re trying to create,” said Kleber.

Recording goals and areas for improvement early in the coaching process is important for outlining future sessions and progress.

“Document what the rep wants to work on so that you can go back the next time and see how it’s going and if there are other tactics [needed],” said Kleber.

An accountability plan provides coaches and reps with a single, reliable resource to set goals, record progress, and evaluate future directions for development.

“It’s one thing to arm someone with the knowledge to do the job, it’s another to really arm someone with all the information and best practices to really perform at a high level in the role,” said Carlton.

Accountability planning can be the difference between getting a job done and truly excelling, and coaching sessions create the structures and support needed for high-performing reps.

When coaches and reps commit to a dedicated, long-term coaching relationship, they can see positive outcomes in both business and the rep’s professional development. These positive outcomes, however, require much more than just consistent meetings. Approaching coaching sessions with an intentional mindset, adequate preparation, and a willingness to commit to an accountability plan can ensure that coaching produces successful results in the present and into the future.



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