Your Business: Upselling Strategies

Be sure your sales team understands the “why” and “how” of your customers’ decisions

When salespeople suffer from any of the weaknesses above, they tend not to be as inquisitive as they should be. They don’t sell based on value and they cannot easily differentiate their products and services from competitors. There are two simple abilities that will help combat these problems: The ability to understand why the prospect will buy; and the ability to understand how the prospect will make the decision.

If salespeople take the time to focus on the real reason behind why the person might buy (or might not), and uncover how compelling the reason really is, they will be more successful. All too often, salespeople forget to find out if the prospect even needs or should buy our product.

Start with the why: Salespeople who start with the “why” have far more success navigating the sales process and spend less time chasing people who aren’t going to buy, which frees up their time to focus on those that will. When the salesperson fully understands why someone will buy, then they can connect with them more easily and seamlessly make suggestions of additional services. Because they are more trusted, the prospect generally accepts their recommendations.

A salesperson needs to learn: Why the prospect willing to talk with them; Why they are interested now and weren’t before; and why they chose the providers they are considering.

Understand the how: Learning how the prospect will go about making a decision is the second skill that will support more robust upselling. For example:

  • Could there be a situation where the prospect won’t buy at all, and what would those situations be?
  • How did the prospect decide to use their current provider?
  • How will they know a provider is the right choice?
  • How will they go about deciding which provider?

While there are several core causes of poor upselling (or poor selling in general), a steady routine of asking “why” and “how” questions will help any salesperson navigate the sales process more effectively and produce far better results.

Upselling doesn't need to be pushy or result in creating a bad reputation. When done correctly, upselling will increase revenue from referral-generating new customers. Coach your team to listen to prospective customers, ask questions and be in tune with individual needs. They need to work on setting their insecurities aside and focus on being more inquisitive. Not all prospects want additional bells and whistles, while others can greatly benefit from added services. When upselling is approached smartly, salespeople can create happier customers, grow referrals, lower attrition and increase sales.


Gretchen Gordon is owner of Braveheart Sales Performance, and a renowned speaker and veteran of the security industry. Braveheart is a sales consulting firm that guarantees improvement in profitable sales for businesses with data-driven sales team evaluations, sales effectiveness training, salesperson recruitment and sales management outsourcing.