Please allow 10-12 business days for a reply, as our inquiry volumes are higher than normal…

Sound familiar?

That’s the reply I received after sending an email to the product support team of my favorite coffee maker last week after it stopped working.

Now, I’m a reasonable person, but waiting 10-12 business days…just for a response?

Not happening.

So instead of waiting, I proceeded to purchase a new coffee maker (by a different brand) for a few key reasons.

In today’s issue, I want to unpack points 1 and 2 above because I was reminded of something we often forget when operating our memberships:

Members are real people with real problems.

And their trust can be lost in an instant.

Let’s dive in.

(And by the way, it’s now eight days later and I still haven’t received a response to my inquiry.)

There’s a certain type of appeal around membership metrics.

They give you something to fix. Something to push on. Something to celebrate.

But metrics don’t tell you when someone is quietly slipping away. They don’t tell you when someone feels frustrated or let down by your service. They don’t tell you when someone logged in, looked around, and thought:

“Maybe this isn’t for me after all.”

Metrics just tell you what someone did.

Not what they felt.

And if you stop paying attention to what people feel, your membership becomes a machine.

Well-oiled. Efficient. And slowly...hollow.

Because behind every “inactive user” is a person who once trusted you.

Who once said yes to something you promised.

Who once believed your membership might help them change something.

And the moment they feel forgotten, or unseen, that trust cracks.

Not loudly, but quietly.

That’s typically how most members leave. They don’t make a scene for all to see and hear. Instead, they walk away in silence, carrying their frustrations with them.

And those are feelings that will forever be associated with your brand.

You see, as an operator, there’s a real cost to not tuning in to the feelings that drive the actions we often measure in our dashboards, charts and metrics.

And it’s not just the cup of coffee.

It’s the ongoing trust that your members will associate with your product - potentially for years to come.

And reliable, predictable revenue will always follow trust.

And that trust must be protected at all costs - even when it feels insignificant.

It’s easy to forget, but important to remember: Most people don’t join memberships casually.

They join because they’re hoping for something.

A breakthrough. A connection. A rhythm. An escape.

The moment they click “join”, they’re not just buying access. They’re taking a risk.

They’re saying:

“Maybe this will help.”
“Maybe this time I’ll stick with it.”
“Maybe this could be interesting.”

And you get to decide what happens next.

You get to decide whether their hope is honored, or left hanging.

And honoring that hope doesn’t mean giving them more content. It means remembering that there’s a person behind the payment.

Someone who wants to feel seen, not processed.

Someone coming to you with real problems - and looking to you to help solve them.

So here are three simple, high-impact ways to incorporate this thinking into your membership.

1. Design for Moments, Not Just Milestones

Not every win is a conversion. Sometimes, the most meaningful thing you can do is meet a member in their moment.

→ A check-in email after a long silence
→ A quiet acknowledgment when someone’s fallen off
→ A note that says, “Hey, no pressure, but we noticed you haven’t been around. Anything we can help with?”

Small, human touches go further than the most polished automation.

2. Don’t Just Collect Feedback, Follow Up Like a Friend

Surveys are easy. Listening is hard. But members feel the difference between being heard and being analyzed.

→ When someone shares feedback, follow up personally.
→ Let them know how it shaped a change or why you chose not to change something.

You’re not collecting data. You’re continuing a conversation.

3. Show Them They’re Seen

No one wants to feel like a data point. But members want to feel recognized.

→ Use names. Reference past contributions. Highlight quiet consistency.
→ Celebrate micro-engagements and the contributions that members make to your program - and how those help move it forward.

When members feel like they matter, they will prioritize their relationship with you.

You don’t have to choose between systems and soul.

You can build a business that runs smoothly and connects deeply.

But connection can’t be an afterthought. It has to be a principle.

When I dig into what truly drives members to to cancel their memberships, I find the following to hold true:

People will forgive slow feature releases.

They’ll forgive imperfect onboarding.

They might even forgive a broken link.

But what they won’t forget is how your membership made them feel.

Did they feel welcomed? Did they feel understood?

Did they ever feel like someone was paying attention?

Trust isn’t earned once. It’s earned again and again. It’s a loop - a fragile one at best. And when you lose it, no feature or fancy benefit packaging will win it back.

So today, I’m leaving you with this question:

Which of the following would be most meaningful to your business: Knowing the rate of engagement in your membership or the rate of broken trust?

Think about it.

Tell me: What challenges are you currently facing with your membership? How can I help? Respond to this email and let me know (I always read every reply).

Share: I want Operator to be the most valuable thing that comes across your inbox each Tuesday. If I’m hitting that mark, share this newsletter with your staff, a team member or friend (just copy and share this URL).

See you next Tuesday.

-Michael