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4 Strategies for Coaching Your Sales Team in a Virtual World

Sales management

how to coach a sales team virtually.

17 March 2022Blog

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Virtual Sales Coaching Drives Results

Over a period of five years, Gallup studied more than 50,000 managers. Their research was exhaustive, covering more than 500 questions. One finding stood out among all other data points: “Managers account for an astounding 70% of the variance in team engagement, and their efforts substantially impact the bottom line of entire organisations.” This discovery illustrates the high-stakes challenge of coaching in a virtual setting.

The same body of research reveals that managers, on average, report spending five hours a day with other people. Given the influence and scale of a manager’s interactions, it is not surprising to learn that many team leaders acutely feel the absence of in-person interactions like one-on-one meetings or even a casual walk-by.

Sam Bacharach, a professor of labour-management at Cornell University, cites some of the new challenges of coaching virtually when he asks, “How do you listen constructively? How do you instill trust? How do you begin that deeper dialogue that actually makes someone want to deliver for you because you’re in their corner?” What makes these challenges so critical is the fact that we are in a period when effective coaching is needed more than ever. The pandemic has left teams distributed, communication interrupted, and the path forward unclear.

Here, we explore the four guiding principles behind an effective approach to coaching in a virtual setting. These four ideas can be enacted immediately and will equip sales leaders to rediscover the kind of dialogue that fosters meaning and motivation.

Ensure the Sales Professional Talks First, Last, and Most

One of the defining challenges of the pandemic is that it has created an overlap in the work-home balance. Conversations are now occurring in a household setting, where distractions are ever-present. These distractions often force us to multitask despite clear findings like those from Stanford researchers who have determined that “heavier media multitaskers often exhibit poorer performance in a number of cognitive domains.” In response to these distractions, managers often feel the pressure to move fast, which leads to an urgency characterised by simply telling the sales professional what to do.

The problem with this approach is that it places the responsibility entirely on the manager. Earning the sales professional’s buy-in becomes difficult because they played no part in developing the solution. Moreover, this style circumvents the critical thinking skills necessary for personal growth. To succeed, a sales professional, like anyone else, needs a sense of ownership. They need to feel that they have some control over the outcomes that will determine their success.

Avoiding the natural impulse to simply tell someone what to do means engaging them in a dialogue. The sales professional should do the majority of the talking while the manager encourages them to offer more details by asking questions. These details equip the manager to gain a better understanding of the challenges facing the team member. Without this insight, the manager risks offering feedback that is irrelevant and short-sighted. Accountability drives success. Without participation in the dialogue, the sales professional can only follow another person’s path.

Just as the sales professional must engage in a questioning strategy that delves below the surface, so must the manager. It is not enough to settle for superficial questions like, “How are things?” or, “Is everything going ok?” Instead, managers need to get to the core of the issues and use the time wisely. Rapport must be earned.

Diagnose Before Prescribing

Diagnosis takes time. Traditionally, this has been a problem because managers have limited schedules. They have a long list of responsibilities, and new challenges emerge daily. This frenetic pace is only intensified by frequent travel to meet with clients. Since the pandemic started, however, travel has dropped dramatically, and for many, it has disappeared entirely. While this change has resulted in fewer in-person interactions with clients, it has also given rise to an unexpected benefit: managers now have more time to engage with their team.

This is good news when it comes to the challenge of diagnosing the underlying cause of a performance gap because extra time affords the manager options that were previously unavailable.

For example, many managers now have the time to observe a sales professional’s virtual engagements with customers. This additional time to devote to collaboration might explain why so many sales leaders are discovering the need to make structural changes to the ways sales teams approach today’s changed market. Consider recent research from McKinsey, which shows that 77% of leaders cite retraining salespeople as “very or moderately important” In response to the changes prompted by the global pandemic.

Leaders can also help diagnose underlying challenges by asking open-ended questions. Too often, people misunderstand this critical component of coaching. They ask questions designed to elicit a specific response. These kinds of questions feel like an interrogation. They key is to ask open-ended questions that bring the individual into the dialogue. These kinds of questions signal to the sales professional that they have the freedom to influence the conversation. With open-ended questions, the conversation is dynamic, not directive.

In this setting, the person being coached is free to take the prompt in whichever direction they feel is best. They are not cornered into providing a narrow answer to a narrow question. In contrast, open-ended questions encourage an open dialogue. This openness is important for the coach because it gives them insight into the individual’s perspective.

Coach with a Broader Purpose

It is easy to think of coaching as a means for addressing a shortfall in performance or as a way to drive more from a team. While coaching is effective in these circumstances, managers today should think of coaching as something more. They should think of it as a way to reinvigorate engagement. Research from McKinsey illustrates the value of this idea. In a survey of 800 US-based employees, they learnt that the largest gain (+55%) in engagement across ten factors was seen in “nonfinancial recognition,” or, more simply, “being recognised for my work.” This data has particular relevance today as leaders seek ways to sustain and grow employee motivation at a time when financial resources are limited. Regular coaching conversations help buoy morale in these unprecedented times when social distancing upends traditional communication. Simply: coaching, even when there is no pressing issue, is important because it keeps people connected.

This involvement is a precursor for engagement, which is necessary for any successful organisation. Consider findings from Gallup, which reviewed data from 31 million respondents. The researchers learnt that “employees who are engaged are more likely to stay with their organisation, reducing overall turnover and the costs associated with it. They feel a stronger bond to their organisation’s mission and purpose, making them more effective brand ambassadors. They build stronger relationships with customers, helping their company increase sales and profitability.” These findings are a powerful endorsement for the kind of engagement that comes from coaching. Engagement drives success and therefore achieving it requires an intentional, mindful approach.

Avoid the habit of coaching only when circumstances demand intervention. Instead, consider moments when coaching, or even a less formal conversation will serve as a replacement for the spontaneity of a corridor conversation. This approach demonstrates to team members that coaching is more than a managerial tool — it is a way to renew connections that all too easily attenuate when everyone is engaged in remote work.

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Leverage the Advantage of Analytics

Coaching in a remote work setting is akin to relying entirely on instruments during a low visibility flight. Fortunately, coaches today have a wealth of analytics that are critical in the absence of in-person interactions. The advantage arises from knowing which analytics should serve as a prompt for coaching.

Effective leaders should examine trends like pipeline velocity which illustrates how quickly a sales team is moving an opportunity through the sales cycle to reach closing. This measurement reveals the sales professional’s overall effectiveness because the calculation encompasses qualified opportunities, win rate, deal size, and the length of the sales cycle. Therefore, a detrimental change in any one of these four factors will be reflected in this single measurement. As a result, leaders can quickly isolate the area where success is faltering and help the team address the underlying problem. Data like this is a valuable way to jumpstart the process of learning where the sales process has faltered so that the coaching dialogue can immediately focus on the “how” part of problem-solving.

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Leaders also need to leverage analytics that reveal deal slippage, which is the percentage of committed deals that do not close within the anticipated window. In today’s environment, organisations are attempting to survive on fewer deals. As a result, a customer’s decision to let a purchase slip into the next quarter represents a larger proportion of the expected revenue for the current period. An increasing slip rate also disrupts forecasting capabilities and presents the risk of once viable opportunities getting overshadowed by plans for the next quarter.

While important, factors like pipeline trends and deal slippage are only two metrics on a nearly endless list of data points available to sales managers. Therefore, many are turning to the power of AI to focus on the activities that have the greatest impact on the numbers. AI capabilities are growing at a time when they are needed most. Today, sales managers must address numerous responsibilities like attending daily meetings, responding to emails, and forecasting. AI allows managers to do more with their limited time by providing fast, granular-level insights on what the most effective performers on the team are doing to win the sale. As a result, leaders can leverage this data to help underperformers replicate the activities and approach of the top sales professionals. Simply, AI allows managers to isolate the difference-making behaviours seen in successful deals and thereby disseminate those skills across the team.

It is important to remember that AI is not a substitute for management. To work effectively, AI must be part of a larger plan that goes beyond metrics and measurement. This idea is best illustrated by research from MIT Sloan Management Review and Boston Consulting Group in which analysts surveyed more than 2,500 executives about their AI investments. One of the most powerful findings from the data was that “getting the most out of AI requires a team effort.” This led the researchers to conclude that AI should be thought of as 10% algorithms, 20% technology, and 70% business process transformation.

Coaching has become even more challenging at a time when it is needed most. The current setting represents an opportunity for managers to rise to the occasion and reinvigorate teams with coaching that puts the sales professional first, seeks to understand underlying challenges before moving to solutions, and aims to create conversation even when there is no pressing concern.

While a virtual setting adds to the already considerable challenges of coaching, the unusual circumstances of today have also afforded new ways to connect and more flexible schedules. Given the distant and dispersed nature of teams today, the need for excellence in coaching is not as visible as it was prior to the pandemic. Therefore, leaders must keep this core skill at the centre of their thinking as they navigate terrain that is still taking shape.

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