How to Upskill Your Sales Team Effectively

Technology and the overall business landscape are constantly evolving – and with it, customer requirements are being turned on their heads. So, it’s no surprise that selling tactics that were once effective are now outdated and insufficient.

There are no mincing words: modern companies must equip sales teams with the latest knowledge and skills to stay ahead of the curve and close more deals. You must adapt, learn, and apply new techniques if you want continued growth and success in today’s competitive market.

But hopping on the latest trend or technology isn’t enough. You need a structured approach to upskilling your sales team – one that aligns with their specific needs and your organization’s goals.

In this article, we’ll explore seven steps to help you effectively upskill individual sales agents and teams, so everyone can reach their full potential. But first, let’s explore why upskilling is so essential in the first place.


What is upskilling and why does it matter for sales teams?

Upskilling is the process of developing employees’ skills, knowledge, and capabilities. By increasing their skillset and honing existing skills, you help them to perform more effectively and better prepare for new roles, responsibilities, and even wider industry challenges. 

For a sales team, upskilling involves equipping agents with the necessary competencies to adapt to changing market dynamics and deliver consistently positive results.

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The specific objectives of an upskilling strategy can vary significantly and will depend on your organization’s requirements and your industry. For instance, agents who sell contact center solutions to global businesses may need upskilling in areas such as customer service or AI analytics. 

On the other hand, a manufacturing company’s sales team may prioritize outcomes involving improving supply chain awareness.

Whatever the case may be, the goal remains the same: to enhance individual employees’ performance and productivity to boost the sales team’s overall success rate. 

An upskilled sales team is more likely to:

  • Adapt to market changes: Key knowledge and skills enable employees to quickly pivot and adjust strategies as market dynamics shift and evolve. A well-trained team proactively adapts to stay ahead of things like new competitors and changing customer behavior.
  • Effectively leverage technology: Today’s sales professionals should be able to harness the full potential of technology. CRM systems, analytics tools, and other sales software are becoming increasingly powerful. Your organization will inevitably fall behind if your team lacks the required knowledge to use these tools to their advantage.
  • Consistently meet and exceed targets: Hitting sales targets is great. But is your sales team doing so more often than not? Upskilling plays no mean role in helping them nurture leads and close deals consistently.
  • Increase customer satisfaction: The better your team understands customer needs, the better equipped they’ll be to offer the best possible solutions. With that comes enhanced customer experience, satisfaction, and loyalty.
  • Creatively handle objections: Upskilled salespeople know how to deftly outmaneuver objections and transform them into valuable opportunities. It doesn’t always happen that way, but upskilling ultimately increases the likelihood of closing difficult deals.
  • Build stronger client relationships: As they learn how to communicate professionally and develop better interpersonal skills, your sales team will do more than increase sales in the short term. Even better, they’ll be equipped to nurture trust and partnerships with customers in the long term.
  • Be more engaged and motivated: It’s not just about your business and customers. Upskilled salespeople are more engaged and motivated because they feel challenged and rewarded. They are also more confident in their abilities, making them more likely to achieve their goals.

7 strategic tips for upskilling your sales team

Now you know what you stand to gain, here’s how to go about upskilling your team. When implemented, these tips will help you transform your sales force into a highly skilled and effective unit.

1. Identify current skills gaps

Assessing your sales team for gaps in their skills may not be the most thrilling part of the upskilling process. But it is essential. 

After all, without a thorough understanding of each individual’s strengths and weaknesses, you won’t have a clear path to improvement. But this goes beyond individual assessments — you need a comprehensive snapshot of the collective team.

Here are a few questions you need answers to:

  • Are there any areas where your salespeople are consistently falling short?
  • What skills do they think they need to improve to be more successful?
  • Do your team’s performance metrics reflect the expected standards, or do they highlight consistent gaps?
  • Are certain stages of your sales process prone to bottlenecks or difficulties?
  • What are the top performers doing differently that others could benefit from learning?

With these answers in mind, conduct skills assessments of every team member using tools like self-assessments and peer reviews. On top of this, analyze performance metrics, sales data, and performance reviews, looking for significant patterns in performance.

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Once you know where your team needs to improve, you can begin to develop a plan to address those gaps. 

2. Set clear learning objectives

It may seem obvious, but many organizations go into upskilling programs without a clear roadmap. That can lead to any number of issues, including:

  • Ineffective training programs: Designing and delivering effective training programs is incredibly difficult when you don’t really know what you’re aiming for.
  • Wasted resources: You’re wasting a ton of time and effort for your business and salespeople when training programs don’t align with precise objectives. 
  • Disengaged learners: Employees are more likely to be engaged and motivated when they know exactly what they are expected to learn and why.

“SMART goals” is something of a buzzword, but there’s no doubt that this method is effective — when applied correctly. 

SMART goals are Specific, Measurable, Achievable, Relevant, and Time-bound. That means your objectives should be clearly defined so every participant knows exactly what needs to be achieved and coincide with metrics that enable you to track progress. Goals should be realistic within the context of the training, align with your business needs, and have clear deadlines.

3. Choose the right training methods

Let’s say you’ve conducted research and established objectives. Now, you’re ready to train junior sales agents on creating a persuasive sales deck to upskill them in lead generation and help them close deals more consistently. 

Naturally, you deliver a series of lengthy, text-heavy PowerPoint presentations filled with theoretical content, right? Wrong. That’s like trying to teach someone how to swim by handing them a manual and expecting them to dive into the deep end.

How you handle upskilling your sales team is just as important as what they learn. It can make or break your efforts.

A one-size-fits-all approach rarely, well, fits. Take into consideration the complexity and depth of what they are upskilling. In the example above, a couple of online videos may be enough to cover the basics, then the team can move into actively practicing what they learned. 

However, there’s a lot more involved in something complex, such as negotiating high-stakes deals. Here, interactive workshops can come into play, with your sales team receiving instructor-led training and simulating real negotiation scenarios. 

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Imagine simply reading a book instead. The chances of anything sticking and translating to real-life positive outcomes would be slim.

4. Reward the learning process

Sure, upskilling comes with several personal benefits for sales team members. But don’t think everyone will be enthusiastic about undergoing training.

Many employees worry about how engaging the training will be or how they will align their learning with other responsibilities. But with motivation in the form of incentives comes more engagement, and you’ll find people are more invested in building or enhancing their skills and knowledge.

Here’s how you can make it easy for sales professionals to participate in upskilling programs:

  • Career advancement: Clearly link upskilling to career progression and watch your employees scramble to take advantage of it. Outline clear paths for moving up based on new skills or certifications.
  • Public recognition: Special recognition in the form of tailored awards and trophies, certificates, social media shoutouts, and company-wide announcements can nudge your sales team members to increase their skill set.
  • Financial incentives: There’s nothing quite as motivating as cash rewards. Bonuses or pay rises can effectively incentivize learning progress. You could offer a bonus to employees who complete a certain number of training courses or achieve a certain performance assessment score.
  • Dedicated learning time: Reserve time for dedicated training, separate from other work-related tasks and distractions. Your sales team will learn much better when they aren’t thinking about leads and closing deals anyway.

5. Incorporate cross-functional training

It’s not uncommon for a company’s sales team to work in silos. Agents may be assigned to different industries and clients or have different tasks and responsibilities within the team. This can significantly impact the team’s communication, productivity, and overall success.

The solution? Embrace cross-functional training. Do it right, and it breaks down the barriers between different roles within the team. That way, employees gain a broader understanding of various aspects of the sales process and related functions. 

You never know when it could come in handy. It could mean that when some team members are on leave or off sick, others can swiftly step in to keep customers moving through the sales funnel and maintain client relationships.

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Your organization will reap other benefits, too. For instance, collaboration becomes more effective when team members understand each other’s roles and responsibilities. 

But there’s more to cross-functional training than upskilling within the sales team. It can (and should) also bridge the gap between sales and other departments. 

If a customer asks a sales agent “What is a preview dialer?” you need to know that they have all of the knowledge necessary to give an accurate answer. After all, it could make all the difference in convincing a potential customer to buy your product or service. 

It’s always worth training sales professionals in skills that are traditionally thought of as being outside of their remit. But by letting them sit in on marketing meetings to brainstorm advertisements or receive training from the tech team about a product’s new features, they can gain a better grasp of what you sell. Ultimately, that means they’ll be better suited to position the company’s products and services to resonate with potential customers. 

You might also consider rotating members from different departments through cross-functional teams on projects. This gives team members the opportunity to learn new skills and hone others while encouraging knowledge sharing across the company. 

6. Customize training for different sales roles

Cross-functional training is essential for a well-rounded sales team. However, it’s just as crucial to recognize the unique requirements of different sales roles within your organization. 

Tailoring training to specific roles allows you to enhance specialized skills and competencies. That way, you ensure each team member has the tools to excel in their area of expertise. 

Depending on the size of your organization, there may be several roles in a sales team, from account executives to inside sales reps, managers, and customer success agents. What are the critical competencies that differentiate one role from another? 

If you have to, conduct a thorough assessment of the skills and knowledge each role needs to succeed and how you can build on them. 

Design training programs that focus on role-specific competencies directly. Workshops or online courses are common solutions, but it’s not unheard of for employers to go the extra mile and pay for Master’s degrees for star performers. 

7. Make it an ongoing process

Do you just complete a training program and tick off the checkbox, satisfied that your sales team is set for years? If so, it’s time to change your approach. You must make upskilling an ongoing, perpetual journey – a culture of learning, if you will, that moves with the changing business environment and customer behavior. 

After all, upskilling is not just about learning new skills, but about refining and honing existing ones. The only constant in sales is change itself. 

So, keep the upskilling opportunities flowing. This could include formal and on-the-job training, mentorship programs, self-paced learning resources, industry conferences and events, and more. Each of these presents a chance to foster continuous professional development within your sales team.

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But there’s more to a culture change — it requires a shift in mindset and practices. For instance, management should set an example by actively participating in upskilling programs themselves. It also means creating an environment where employees feel comfortable asking questions, making mistakes, and trying new things. 

Unlocking sales success with upskilling

For many companies, the business environment presents a sink-or-swim scenario where the margin for complacency is almost non-existent. Build and enhance competencies, and your sales team can consistently meet targets, ride market changes, and increase customer satisfaction. 

By ensuring your sales team’s skills are in line with the latest best practices and dedicating time to their progression, you also increase employee motivation, engagement, and retention. So it really is a win-win. 

Remember though, upskilling your sales team is an ongoing journey. Adopt it as a mainstay in your company culture, foster a love of learning, and watch your sales team soar.