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Coaching Reps to Success Amid Uncertainty

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Coaching has the potential to exponentially improve sales performance. But often, organizations leave potential untapped by not investing in the development of coaching skills among managers or not nurturing a culture of coaching. Instead, coaching becomes an afterthought that gets deprioritized amid day-to-day pressures.

There is no magic formula to create a perfect sales coaching technique as it is reliant on several factors, including the resources available and an organization’s structure around learning. But when the economy is causing many leaders to want to batten down the hatches, it is often precisely the moment when coaching can save the day.

“Sales is stressful as it is, but then all of a sudden your deal size is eroding, or your deals are falling out of your pipeline, and prospects or budgets are being cut,” said Jamie Kleinerman, senior consultant of sales performance at BetterUp. “That just ratchets up the pressure for sales. In times like these, coaching becomes more important and coaching on how to be more resilient, handle the stress of that, and bounce back.”

Below, explore three best practices enablement can implement to coach reps to success even through times of pressure and uncertainty. From fostering a culture of learning to unlocking the support of frontline managers and leading with empathy, enablement can be a key driver in developing coaching programs that build resilience for years to come.

Foster a Strong Coaching Culture

A company that invests in a strong coaching culture is often something one can see and feel. It’s woven into the fabric of the organization’s values and speaks directly to the human desire to want to learn, grow, and improve.

“In a strong coaching culture, we’re not just thinking about behaviors; we’re also looking at values and looking at those underlying assumptions,” said Minette Chan, enablement professional and scholar at the University of Pennsylvania.

Chan says practitioners can visualize their coaching culture like an iceberg. The tip of the iceberg, often the most actualized and obvious, is the behavior being coached. Just below lies all of the values driving that behavior — like respect, belief and trust, and psychological safety. Digging even deeper, the third layer of the iceberg reveals the underlying assumptions that develop those values.

“When we’re looking to build a strong coaching culture, for me, it’s about shared underlying assumptions,” said Chan.

As a coach, Chan says it can be useful to look at what might be the underlying assumptions learners may have about them or how the organization treats learning as a whole. For example, understanding if the organization prioritizes and makes time for sellers to learn and invest in coaching can indicate how a seller will engage with the coaching. If it’s clear that coaching is important to the company’s success, then the learner may be more motivated to incorporate coaching as a part of their role.

“It means you’re not aiming for perfection,” said Chan. “It means as people are doing their work, you believe they are getting better, and they’re growing.”

Checking in with how an organization views learning and how it fosters its learning culture means opening up the space for people to learn and make mistakes. A strong coaching culture starts with understanding how a company prioritizes the growth and development of its employees.

“Coaching for sales teams goes well beyond just the sales performance,” said Andrew Zinger, global director of sales enablement at Figma. “I think in making life and work more human, you have to look at the competencies, the behaviors on top of the sales performance. We look to coach across those throughlines within our team.”

Leading with Empathy to Coach to Success

Enablement teams can optimize the health and performance of sales coaching programs through a myriad of processes, tracking progress and reinforcing learning along the way. But when the health of the overall sales team is potentially at risk, enablement can really step in and understand where there may be gaps that can be filled during times of pressure.

“When I think of where there is an enablement gap, is it skillset, mindset, or tool set?” said Cameron Tanner, senior director of global enablement at Cisco. “I think what we learned from the pandemic is that the organizations that were really investing in employees from an empathy perspective and a resiliency perspective were able to weather certain storms.”

Leading with empathy can take various shapes and forms, but it often starts with enablement understanding where certain pain points are for sellers throughout the sales process. To equip managers with as much context and information as possible, enablement can ask open-ended questions that may help uncover deeper issues that sellers are facing. Managers can coach directly on those challenges and help build solutions with a better understanding of where sellers are coming from.

“What is happening outside of their work? There are lots of additional pressures during this time from what’s happening in the economy to what’s happening in different countries,” said Zinger. “All of these things you have to consider in how you deliver the message, the training, and the feedback.”

Empower Frontline Managers to Enhance Sales Confidence

Working through economic duress can likely cause sales confidence to decline. With tightening budgets and strained buyer processes as competition becomes even more pronounced, effective coaching can help elevate sales confidence when it’s needed the most. One of the keys to unlocking the success of any coaching program, but especially during times of uncertainty, is through engaging with frontline managers.

“The number one thing you can do in enablement is empower your first-line managers to coach and reinforce whatever you do,” said Tanner. “It is the single greatest factor you can unlock in your organization to improve your revenue goals and targets.”

Enablement can empower frontline managers to be more effective coaches through efforts such as providing training on how to coach new managers, creating guides to help managers know when and how to coach, and checking in with managers consistently with data and insights to hold them accountable to coaching their teams.

In addition to driving accountability, data and guidance can also be useful in helping managers understand where skill or knowledge gaps are coming from and discovering the motivations behind behaviors to directly coach to the specific needs of their sellers.

“What you really want to start doing with managers is understanding the motivations, the behaviors, the skill gaps of each of the members of your team and making sure you’re tailoring your coaching approach to what each individual needs,” said Kleinerman.

Strong sales coaching programs never lose sight of the goal of creating an environment where sellers feel motivated and supported to succeed in achieving their goals. Enablement can help create effective coaching programs that lead with empathy, provide a space where sellers and managers understand the value of coaching and help managers enhance the sales confidence of their teams. Coaching can help teams become more resilient and ready to take on the next challenge to optimize sales performance for the future.



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