Coaching the Sales Team: Three Best Formats

I’ve been running sales and customer success teams for many years now and firmly believe that one of the critical components of continuous growth is ongoing training and coaching that doesn’t stop after the initial onboarding. Regardless of how amazing the onboarding program is, it is physically impossible to fit all the skills, knowledge, and business acumen into it. And the most successful reps are those who proactively seek improvement every day after its conclusion. I do believe, though that it is the leaders’ responsibility to organize and facilitate the training and coaching sessions and steer the reps in the right direction both initially and as they progress in their careers.?

Like almost any process in our account development org, we have been experimenting with different training and coaching formats. Through trial and error, we’ve identified the ones that proved most effective for our team and led to noticeable improvements in both sales target and retention target attainment. Let’s review these three formats and discuss why they proved effective.?

Product deep dive

Pure technical knowledge will not be very helpful without understanding the context of the business scenarios and how that product solved customers’ challenges. However, strong product knowledge and business acumen together form a powerful combo. This is why I partner with our product team, professional services team, and representatives of our technical partner organizations every now and then to facilitate enhanced product training focusing on particular areas. I quickly discovered that the “ok, what questions do you have for our expert today?” format is ineffective. Yes, several top performers with advanced knowledge may have several questions, but that would be about it. Instead, it all starts with an assessment of the team’s understanding of the product, which is performed by the managers. We identify areas where there’s room for improvement, and they do a quick survey (sometimes in written form and sometimes during meetings) to collect opinions from team members on the most urgent areas. These opinions are gathered not in the closed format (is it important for you to be better at feature XYZ?: yes/no), but by using open questions. For example, we may ask what are the particular parts of a specific product area that team members find challenging to demo or answer questions about. All these data points are then used to prepare a session.

We always ask the trainer we invite to start with the basics. We do it because the experience among the team members varies, and what may be well-known to one employee could be entirely new for the other. After that, we move forward with the questions/topics that team members raised previously. I have to say that sometimes the questions prepared were so specific that even the most experienced people from the product or partners couldn’t answer all of them initially and had to commit to coming back to us with the responses. But these are always very fruitful conversations that give birth to many a-ha moments for the team. Another area that we usually spend time on during these sessions is handling customer objections and concerns. Two specific topics to raise on this matter are the possibilities and limitations of the feature. Having a clear understanding of both enables sellers to set the right expectations for the customers and produce better-qualified opportunities.?

Mock calls

While particular training and coaching activities may be effective in groups, individual practice sessions are usually more impactful. When reps’ specific strong sides and areas for improvement are considered, the probability of achieving faster and better results is higher. One such activity that proved effective in the ADM team was conducting mock calls. A hypothetical scenario is presented to the rep - e.g., “client has a low usage of the product, and the renewal date is around the corner” or “This is your first interaction with the client, and you need to both provide value and ask effective discovery questions.” Then, the mock call is conducted in roleplay format, where the trainer plays the role of a customer while the rep tries to resolve the situation to the best of her ability. Given the fact that our team managers are tenured Wrikers with vast experience in handling various customer situations and challenges, these roleplays look and feel very realistic and the experience gained from them can be applied to real customer scenarios moving forward.?

Before starting a roleplay, reps receive a list of clear and measurable criteria based on which their performance will be evaluated. They also receive specific details about the hypothetical “customer” that they usually can find in Salesforce - e.g., annual spending, renewal date, product usage, etc. They get clear instructions that they should not assume anything about the customer - if something is unclear, they should simply ask directly during the call. Regardless of whether a particular mock call gets a pass or needs to be redone, the rep receives a detailed report with feedback in written form that they can use to improve their skills and knowledge further. The only challenge for the management with mock calls is that since they’re conducted in 1:1 format, it might be pretty time-consuming to do them with the whole team - given all the prep work required to come up with scenarios and potential second and third attempts.?

Best practices sharing session

One of my most common recommendations to my team is, “Let’s not try to reinvent the wheel, but instead scale what’s working well.” Whenever a team member discovers that a certain approach/activity proved effective, I double-check that this was not a one-time accident and start scaling that approach to several other team members. If they replicate success (at least - to a certain extent), we review the data, describe the approach in detail, and publish it in our team’s playbook. But while I consider our playbook a fantastic resource for the team, I don’t believe it can fully substitute a live coaching session. So, the best practices sharing session is yet another format of training/coaching that has proved effective for our team. Before the session is delivered, the top performers are thoroughly interviewed by the management to ensure that all the recommendations they share are clear, concise, and actionable. Based on these interview(s), we prepare the content for the session, send it to presenters for review, and then help to facilitate the sessions.?

We usually intervene as little as possible - only sometimes, it seems like a good idea to get the conversation back on track if it has been seriously derailed by very specific questions that are irrelevant to the entire group of participants. We ensure the session is recorded and added to our internal knowledge base along with the handouts and slide deck. There’s no limit on the topics' scope - from the best timeslots to engage in prospecting activities to effective email templates and building long-term relationships with clients. After the session, a mandatory action item for the management team is to continuously ask during 1:1 meetings with reps which of the best practices they could implement and what results emerged from them.?

Choosing the right training format increases the probability of information being shared during it to stick. As a result, the team’s performance is improving, which, again, can be used to to convince those hesitant to change their approach since management would have the data to justify their points.