Why, How, and When to Upskill Your Sales Team

One lesson of COVID was how fast things change. In an instant, sales organizations saw their operations and teams rendered dramatically less productive. It wasn’t just prolonged downtime. It was an epic cultural shift that upended our processes, people, and priorities. At the same time, organizations struggled to support yesterday’s reps with today’s problems.

Another takeaway was changes in modalities and workforce. This altered expectations and the very definition of “employee satisfaction.” In addition to an uncertain economy, organizations now face dispersed sales teams and a lexicon of new phrases. They could have “a human energy crisis,” with sellers “in Goblin Mode,” on “bare-minimum Mondays.” As colorful as this sounds, your bottom line will be monochrome: in the red.

As the way we work has changed, the way we sell must change. According to McKinsey’s 2021 Mind the [skills] gap, 87 percent of companies have or will have a skills gap. This makes upskilling so essential. More than updating culture or compensation, upskilling empowers your team to reinvest. It motivates and boosts confidence, giving reps the tools to succeed. With that in mind, here is why, how, and when to upskill your sales team:

Why You Should Upskill

In 2017, McKinsey Global Institute released Jobs lost, jobs gained: What the future of work will look like for jobs, skills, and wages. Here, they estimated that, by 2030, automation and AI technology could force 375 million workers to switch jobs. This was three years before the pandemic. Think of that in terms of sales, an industry on the forefront of change.

For salespeople, change is constant. We’re all familiar with economic fluctuations, emerging markets, new products and technology, and organizational turnover. However, additional sales-specific considerations also affect job satisfaction and performance. These include:

• The complexity of sales
• Generational differences
• Better informed buyers
• More skilled negotiators

As the economy shifts, your buyers’ needs change. So does their buying process. Uncertainty brings skepticism, tighter budgets, and more decision makers—for new and existing customers. New buyers are increasingly hesitant. Regular customers still buy, but it’s often prolonged sales cycles with more decision makers. In short, once easy sales become complicated affairs. This affects a seller’s quota and the organization’s productivity. Upskilling ensures your team is ready for the increasing complexity of modern selling.

Another change is the generational makeup of your sales team. While no one generation is better at sales, there are differences. Veteran sellers may bristle at new tech. Millennials and Gen Z are often motivated by workplace culture and noble pursuits like equity, diversity, and sustainability. Of course, sales organizations must mind these things, especially their effect on employee satisfaction, performance, and retention.

The internet revolutionized sales. One huge change is better informed buyers now wait to engage sellers. This puts those sellers at a disadvantage. Also, it increases competition. As buyers know more about their problems, potential solutions, and available resources, the more discerning they can be.

In addition, better informed buyers mean better negotiators. While procurement teams have always been tough negotiators, individual buyers have not. This makes it more challenging for sellers to stand out and advance through the buying process. It also reduces access to important decision makers, such as the C-suite.

These challenges increase the pressure on sales organizations. Regular concerns, such as hiring, onboarding, and retaining talent, are more challenging. This makes it essential to upskill the sellers you have.

How to Upskill Your Sales Team

• Hiring
• Onboarding
• Enablement
• Sales coaching
• Sales training

Of course, you can’t upskill new hires—at least not yet. Their experience and expertise were set before you found them. However, be proactive. Consider the skills and competencies needed to perform their roles effectively and design training to develop these skills. Also, ensure new hires understand your sales process and are receptive to coaching and training.

In addition, onboarding is not orientation. Although orientation is essential, administrative assistants and accountants are not account managers or BDRs. Onboarding needs to be sales specific and geared to a rep’s sales duties. This includes early preparation for ongoing development. For more, see our white paper Finding, Onboarding, and Retaining Top Sales Talent.

Sales enablement provides your team with the tools and resources to succeed. An important aspect is content creation, including white papers, case studies, blogs, demo decks, and product/pricing sheets. These help your sales team generate interest and differentiate themselves and your products from the competition. Ideally, content is a collaborative effort between sales and marketing. Ultimately, it’s a comprehensive strategy to enable teams to win. Upskill yours with better content and ways to use it.

According to Brainshark, over 60 percent of salespeople would likely leave if their manager were a poor coach. This stat alone shows the value of sales coaching. Of course, coaching needs to be regular and targeted to the skills and processes sales reps need. But upskilling is not only for sales reps. You must also upskill managers to ensure they can coach best practices for the current sales environment.

Hand in hand with coaching is sales training. All sellers have their regular habits and history of success. Sales training takes reps out of their comfort zones. It exposes them to fresh ideas to maximize their activities and engagements in a changing environment. As such, training should never be a stand-alone event. It must be paired with ongoing coaching, assessment, and continued learning.

Consider these eye-opening statistics on sales training:

• Companies that invest in sales training are 57 percent more effective than their competitors.
• Sales training can boost an individual reps’ performance by an average of 20 percent.
• Sales training achieves an average ROI of 353 percent (Janek clients averaged nearly 900% in 2022).

Sales training is an investment in your team. It ensures their skills are updated to meet current changes and challenges. And, at its best, it keeps them motivated, confident, and driven.

For more, check out our white paper Finding, Onboarding, and Retaining Top Sales Talent.

Seven Essential Skills to Upgrade

• Prospecting
• Relationship building
• Active listening
• Empathy
• Storytelling
• Negotiating
• Virtual selling

Sales prospecting is a bread-and-butter skill. We must attract new business to thrive and grow. However, over time, the way we prospect changes. New technology, such as CRMs and the internet, transformed sales prospecting. Today, it’s social media and digital. To keep pace, upskill your prospecting process to maximize today’s tools.

If the old model of selling was product centered, it’s now relationships. Today’s buyers have countless companies and products at their fingertips. More than great prices and flashy features, they need sellers they trust. This starts with generating rapport and building relationships. However, as we change engagement, such as digital and virtual, we must upskill relationship building.

For top sellers, there’s a difference between listening and active listening. This difference is in how and what we hear. While most listen for content alone, active listening goes deeper. It’s about content, meaning, and feeling. This is half art, half science. But it’s the basis of understanding customer need, both conscious and unconscious. It encompasses changes in tone, vocal indicators, body language, and other nonverbal cues. It’s an essential skill to master.

Empathy is the ability to understand and share another’s emotional experiences. It is not sympathy, which is feeling badly about another’s situation and can be condescending. Instead, empathy creates emotional connections. The seller’s experience relates to the customer’s circumstances. This builds trust and allows for deeper discovery. Post COVID, customers need this more than ever.

Storytelling separates good sellers from great ones. A seller’s ability to narrate their experiences fosters relationships. It’s how we share our vulnerability and convey empathy. This differentiates trusted advisors from “typical” salespeople. For many sellers, this does not come naturally. Fortunately, it is a skill they can develop.

One fallacy of negotiation is that it ends the sales process. Sellers present products, and negotiators close deals. Today, top sellers negotiate throughout the sales process. As such, negotiating must evolve with the times.

Another fallacy is that negotiation is a zero-sum game. One side must lose for the other to win. While this may have worked once, today, it’s a terrible practice. Now, top sellers know they must give to get. For more pointers, check out our white paper The Ultimate Guide to Sales Negotiations.

If virtual selling was once a niche skill, COVID made it a necessity. Though we’re happy to get back to in-person sales, virtual isn’t going away. According to Gartner’s insights, CSOs expect 60 percent of the sales force to continue working virtually. Today, most organizations have adopted hybrid modalities, incorporating the best of both.

When to Upskill Your Sales Team

Perhaps, the most important lesson of COVID was we cannot predict the future. Some changes you can’t see coming. This does not mean we should forget forecasting, planning, and scheduling. But it does mean preparing for change.

Granted, most sales organizations did not have a once-in-a-lifetime global pandemic on their bingo card. But those with updated technology and virtual skills were quickest to respond. Though they didn’t see it coming, they were ready when it came.

Obviously, waiting for a need is too late. However, check your hiring process. Do you target superstars with track records of blue chips? Have you considered less-skilled but more-flexible and coachable candidates you can grow and develop?

Likewise, asking if your team needs sales training is a sure sign they do. So, if you’re wondering about the best time to upskill your sales team, it’s probably now.