Don\’t assume your best customers are locked in

Editor’s Note: Each week Maynard Webb, former CEO of LiveOps and the former COO of eBay, will offer candid, practical, and sometimes surprising advice to entrepreneurs and founders. To submit a question, write to Webb at

Q. I just lost a long-term customer that I thought was locked in. I had no idea and I don’t want this to happen again. What did I miss?

-Managing director of a fintech company

Dear Managing Director,

This is a difficult situation, but you are not alone in experiencing this.

Companies strive to get customers “locked in” and sometimes, once they do, they become complacent. This is a dangerous place to be. Customers are never locked in. You might be the dominant player today, but it may not stay that way tomorrow. Everything is always changing, people are constantly innovating, and there are always new options becoming available.

I understand your customer’s perspective because I have experienced this personally. I started with a team that did a good job and I needed the service they provided. They knew that and continued to offer me the same service. But over time, my needs evolved and the service they provided didn’t. I believe there were signals that I was outgrowing them—I had to bring in other people to help me think through how to handle the next phases and provide services they didn’t offer. However, they didn’t see it as a sign of my unhappiness. They never asked if my needs had changed or if I was satisfied with what we were doing together. I believe they assumed I was locked in, and were very surprised when I left, but I needed new wisdom and services more than I needed to avoid the switching costs or hassle.

Never assume that a customer will stay with you. Once you get a customer, you must work tirelessly to keep them. In all relationships, whether it is a marriage or a business partnership or a customer, you should treat people as if everyone is opting in all the time. You can’t feel entitled; you can’t think that someone won’t leave. The best way to be opted in is to make sure both sides are delighted.

It’s important to stay in touch and make sure the customer is feeling engaged. You should ask your customer questions like, “Is this working for you,” “What else can I be doing?” and “What can I do better?”

Always check in, with the understanding that things evolve. Go over what you are doing together and discuss what can change. Ask if they are in a different place. Learn about the strategic vision and plan. Ask them what they would like to do next. Ask, “What else are you thinking about?”

It’s necessary to make sure you are on track—and to get ahead of where they are right now. You have to assess not just what you have been doing but anticipate what new needs might be and run ahead of that. Know where your customer is and where they are going and bring them solutions at the appropriate time so you can grow and evolve with them.

You should know what every customer is thinking about your relationship. If someone asks them on scale 1-10 how delighted they are, you should know what that score is and why.

Don’t assume your customer can’t go somewhere else. They can. Do everything in your power to make sure they want to stay with you.