How to Personalize Your Sales Training Like a Pro

These days, customers expect a lot of the salespeople they interact with. According to Salesforce’s State of the Connected Customer Report, 73% of customers expect companies to understand their unique needs and expectations, 62% expect salespeople to anticipate their needs, and 56% of customers expect offers to be personalized.

While some customers will always expect to be treated like VIPs, this mindset has become more prevalent in recent years. Technology has improved and personalized the buyer’s journey. The impact of the pandemic also can’t be underplayed: during lockdown, digital selling increased exponentially. Buyers now expect to be able to purchase almost anything online — and they expect an excellent experience during the transaction.

Personalization at scale isn’t easy; particularly not for overworked sales teams, who often face burnout in the best of times. Although there is no one definitive report, sales turnover hovers around 33% and more recently, sales turnover rates appear to be 58% higher than in 2020. This is no surprise; sales organizations have had to weather a recession, and sales teams who used to sell in person are now learning new online sales skills.

The additional expectation of providing personalized attention to every single prospect may seem daunting. However, there is a strategy that can help: adaptive selling.

Why Personalization Matters in Sales Training

82% of companies are working to improve personalized learning, according to a Litmos and Brandon Hall Group Report. Organizations understand that in order to keep employees engaged, they need to offer growth and development opportunties tailored to their employees’ needs and goals. To reduce churn amongst sales representatives and drive sales revenue, personalized training is a must.

When a salesperson can access the most relevant learning materials the moment they need them, they are more likely to stay engaged with and feel ownership over the training they take. And when learners feel connected to their training courses, they’re more likely to remember and apply what they’ve learned. Bottom line? Training personalization drive sales performance by enabling reps to learn at their own pace, focus on areas where they need improvement, and apply skills more quickly after learning them.

When a salesperson has the skills, knowledge, and confidence to adapt their selling approach and personalize customer experiences, everyone wins. The customer feels a sense of satisfaction and loyalty, and may even buy more from your company because of their personalized experience with a knowledgeable sales rep. The sales rep feels valued and accomplished, because they were able to achieve a professional goal or apply what they’ve learned to accomplish a sales win.

So, how can sales leaders harness the power of adaptive learning to drive adaptive selling? Let’s start by differentiating the two and exploring how taking an adaptive approach to sales training can enhance your organization’s adaptive selling strategy.

What is Adaptive Selling?

Adaptive selling is a sales methodology that can be used to tailored a salesperson’s approach to every customer on their roster. For sales reps, this means taking several elements into account during sales interactions, including the type of customer being spoken to, the sales situation at play, and the unique needs of the prospect. Adaptive selling encourages salespeople to throw out the script and adapt their sales pitch or presentation to the individual customer.

Adaptive Selling Examples and Best Practices

If your sales rep has ever offered customized rates or put together a custom SKU for a customer, based on that customer’s specific needs, they have practiced the art of adaptive selling! Adaptive selling focuses on tailoring a salesperson’s approach to a customer. There are several techniques that can be used in adaptive sales. All of them include a representative being attuned to the needs of their customers and changing their approach to fit those needs. For example:

Reading the customer: Understanding the personality, communication style, and level of product knowledge of a customer. If a customer is led by emotion, opt for a personal story that ties back to your brand. If your customer is numbers-driven, skip the small talk and get down to data during your next call.
Tailoring the message: Choosing language, tone, and a product focus that will resonate with a particular customer. Does your customer’s company serve a massive global market, or are they a small scrappy start-up? Is their brand playful, authoritative, or highly technical? The more you know your client’s vibe, the more personalized your approach can be.
Adjusting tactics in real-time: Being flexible during a conversation to respond to cues like objections, interest, confusion, or excitement. Active listening is an important facet of adaptive selling, so don’t stick to the script when a client offers new information.

The best adaptive selling technique is building unique relationships with each customers. Building relationships with customers helps salespeople learn more about their specific goals, needs, and pain points, making relationship-building a key element of effective adaptive selling strategies. However, more recently, technology is taking over the adaptive space, making it easier for sales teams to leverage data like site visits or previous purchases to tailor pitches and deals for each customer.

What is Adaptive Learning?

Adaptive learning refers to an educational approach that uses technology to tailor the learning experience to the individual needs, abilities, and learning style of each learner. In the context of sales training, adaptive learning technologies adjust the difficulty, pacing, and style of content based on real-time learner responses and progress. This ensures that training remains challenging yet achievable for each sales representative, allowing them to focus on areas where they need improvement and learn at their own pace.

Adaptive Learning Examples and Best Practices

Customized learning paths for role-specific training: adaptive learning enables organizations to tailor training based on employee roles. For example, new hires receive foundational content, while experienced employees engage with advanced modules. Generative AI tools like chatbots and AI-powered learning paths can further enhances adaptive learning by letting learners curate their learning content in real time, based on their own goals or preferences.
Real-time adjustments to learning activities: adaptive learning management systems can adjust learning assignments or learning paths dynamically, based on the interests or objectives of learners or their managers. For instance, if a salesperson is interested in mastering ChatGPT, they might begin with a foundational course and then ask their AI Assistant to surface increasingly series advanced AI courses.
Just-in-Time Learning: Adaptive learning often takes place instantaneously, especially with the rise of AI chatbots and virtual assistants. These tools provide just-in-time support, especially useful for troubleshooting or on-the-job learning.

Adaptive Training for Adaptive Selling

To an outsider adaptive sales might not sound complex; it’s just listening to your customer’s needs and responding, right? While that’s true on some levels, adaptive selling requires skills some reps might not yet have. New reps, especially, may need to be trained before they can expect to provide customized service.

For example, you may need to provide training in the following areas:

Soft skills: Soft, or transferable skills, might be better called people skills. They include the ability to listen, a polite phone manner, timeliness, and all the skills that make someone a pleasure to work with. Because adaptable sales is about relationship building, providing training for soft skills or people skills is critical in your reps. They need to be able to ask questions, truly listen to what each customer says, and understand that customer’s unique challenges.
Product knowledge: Your reps can’t tailor offerings to each client if they aren’t thoroughly grounded in the benefits of the product you’re selling. Offering product training for sales reps ensures that they know your offerings backward and forward, so that they can adapt their pitch to the clients’ needs while still accuratelyrepresenting your brand and its benefits.
Adaptive selling skills: The flexibility associated with the adaptive selling approach can be confusing for new reps. Learning to adapt your sales approach requires thinking on your feet, which is actually a skill that can be learned. Rather than looking to a manager for permission to change a pitch or presentation, reps need to learn how to seize the moment (as well as which changes are and are not allowed by the organization).
AI skills: AI is still a relatively new technology, and sales reps may not be comfortable with AI tools yet. The introduction of any new sales tool should be accompanied by training, and AI is no exception. Providing AI skills training for salespeople is especially important, considering the rising ubiquity and complexities of AI in the sales landscape.
AI ethics: Customers don’t necessarily trust businesses’ use of AI. According to Salesforce, only 42% of customers trust businesses to use AI ethically. However, consumer trust is critical when it comes to sales, so it’s important that your reps understand how to use AI in compliance with emerging regulations, and can also answer questions about AI and how customer data is used.

Discover How AI is Revolutionizing Adaptive Selling
Now that you’ve learned how to personalize your sales approach, take it to the next level by understanding how AI can enhance adaptive selling. Read our latest article to explore the latest technologies driving this change and learn how to effectively train your sales teams to leverage AI tools. Read more about how AI is evolving adaptive selling for modern sales teams.

*This article was updated on Friday, August 8, 2025