You never want your customers to feel like money machines instead of, you know, people. But that doesn’t mean you completely avoid talking to them about spending more money. After all, you can’t expect them to know all the potential solutions you offer that they’d benefit from.

Even when you have something that will be easier for them to use or more effective, those upgrade conversations won’t automatically be easy. By carefully planning your engagement strategy, you set yourself up for productive conversations and, ultimately, sales.

Use these tips as you create a strategy for building relationships with customers and preparing for upsell conversations.

Regularly Check In

Well before you think customers might want to upgrade, you should talk with them consistently. Show them that you care about their business and want to help them succeed now and in the future. Familiarize yourself with their pain points and goals. Make sure you fully understand how they currently use your product/service.

Then use what you learn to continually provide reliable training and education. As you do, customers will come to see you as a trusted resource. That way when you do decide to reach out about upgrading, they’ll likely be more receptive.

Build on an Existing Relationship and Foundation of Trust

When it’s identified that a customer is a prime candidate for an upgrade, ideally that customer and the person who starts the conversation will have an existing relationship.

This could mean the person who originally closed the sale who has been keeping in touch or it could mean their current customer success manager.

At the very least, the person who is in regular contact from your company needs to provide detailed notes and information to whoever is doing the outreach about upgrading. If you don’t have great notes currently, better to start now than later. The amount of work it takes now to start saving key client information becomes well worth it later on.

Be Honest and Upfront

Securing a meeting under false pretenses won’t end well, especially when you want someone to spend more money. Whether you reach out via text, email, or phone call, clearly explain your intentions.

If you already do regular check-ins with customers, it won’t be weird if you want to schedule a meeting to discuss their progress and upgrade options. If you don’t have that foundation, well, still be honest. Customers respect authenticity.

Similarly, don’t tell a client that you want to talk about one thing and then at the time of the meeting switch to talking about an upgrade. No one likes feeling tricked or coerced into a conversation.

Back Up Your Upgrade Offer With Data

Prove to customers that you understand how they’re currently using your products or services and then show them how they could work more efficiently. Show clients what limits they’re hitting and which upgrades specifically solve their problems.

Give them examples of other similar businesses who have the upgraded version and use those customer stories as evidence.

Again, if you’ve been in regular contact with someone, you should already know the context of their situation and how to best present the possibility of upgrading.

Reward Customer Loyalty

When people have been customers for a long time or when they hit big milestones in using your product/service, create an offer that encourages them to upgrade. Make them feel special and give them something of genuine value. Any offer should be relevant to what they do, not just what you think they should buy.

Many people appreciate trying something for themselves instead of simply hearing that it’s good and worth it. So, a valuable offer might be letting them try out a new feature for a period of time for free or at a highly discounted rate. Other customer will appreciate offers that include consultation hours or one-on-one training.

Ultimately, the offer you choose to share isn’t about making them spend a little more money now just to hit a quota. It’s about helping them find a better solution and rewarding them for their support.

Be more like people

By regularly and consistently following up with relevant information, you and your customers will be ready to have open conversations about upgrading. People prefer to support and engage with human brands, so as you make this part of your customer retention plan, make it easier for yourself and your team by using Skipio, the most human business texting platform available.

Skipio is designed specifically to help teams communicate effectively and build the relationships that matter to businesses. It helps you and every person on your team reach out consistently and personally. See how Skipio will work for you.