Don't try to force customers to adopt new behaviors, like a boot-buyer purchasing sandals. Instead, focus on encouraging them to buy a second pair, a newer model, or an upgraded version of the product they already love. This audience-focused approach builds on existing loyalty and is far more effective.

Customers are guarded with salespeople for fear of being sold. However, they are candid with customer service, freely sharing complaints and unmet needs. This makes the CS department an invaluable, and often untapped, source of sales intelligence and expansion opportunities.

Don't wait for a formal QBR to discuss expansion. The immediate post-sale period is a golden window for additional sales. The customer's excitement and trust are at their peak. With their most urgent need solved, they are highly receptive to addressing other business challenges.

When a customer cancels, don't just offer a discount. Create a capture system that presents tailored solutions based on their stated reason—offer a plan downgrade for cost issues, a 15-minute setup call for confusion, or a feature workaround if something is missing. This preserves value while solving the root problem.

A blanket price increase is a mistake. Instead, segment your customers. For those deriving high value, use the increase as a trigger for an upsell conversation to a better product. For price-sensitive customers, consider deferring the hike while you work to better demonstrate your value.

Systematically identify frustrating moments in the customer journey, like waiting for the check. Instead of just minimizing the pain, reinvent these moments to be delightful. Guidara’s example of offering a complimentary bottle of cognac with the bill turns a negative into a generous, memorable gesture.

Even when a prospect rejects your primary service, you can recover acquisition costs and generate revenue. Offer a free, low-threat consultation (e.g., a 'lifestyle review') where you can sell a different, complementary product (e.g., supplements). This strategy effectively turns a lost lead into a paying customer.

Move beyond selling products or solutions. The highest level of selling is articulating the customer's problem so well, and expanding on its implications, that they see you as the only one who truly understands and can solve it.

Most people mistakenly try to upsell after a customer has received value. The correct timing is when their need is at its peak. You sell two steaks when the customer is starving, not after they've finished the first one, by amplifying their perceived lack before they've had their first bite.