The ninety-day check-in

Three months is a quiet turning point in a membership. The welcome emails have finished, the novelty has worn off and the member has paid you two or three times. By now they have formed an opinion of the membership, even if they have not put it into words. Some are settling in happily. Some are stuck. Some are starting to wonder whether this is really for them.

A short, personal check-in at around ninety days lets you find out which, while there is still time to help. It is one of the simplest retention tools you can set up, and the answers are among the most useful feedback you will ever receive.

Why three months is the right moment

Ask too early and members have little to say. Ask too late and many of the unhappy ones have already gone. Around ninety days, members:

• Have enough experience to give a considered answer.
• Have either formed a habit or noticed that they have not.
• Can compare what they expected with what they got.
• Are often approaching a goal deadline or the end of an introductory period.

If you asked members to set a goal the day they join, ninety days is also a natural point to revisit it.

Send a note, not a survey

A form with ten rating scales feels like admin. A short, plain email from a real person, which the member can answer by hitting reply, feels like a conversation. Ask three questions at most, all open-ended, and make it clear you read every answer.

Here is an example for a hypothetical membership for independent bookshop owners:

Subject: Three months in: how's it going?

Hi Felicity,

You joined three months ago, and I'd love to know how it's going. Could you reply with a line or two on any of these?

1. Has the membership been what you expected? If not, what's different?

2. What has been most useful so far?

3. What's one thing that would make the next three months more valuable for you?

When you joined, you said you wanted to get your events program running. If that's still the goal, I'd be happy to point you to what's helped other shops most.

Thanks, Anselm

You can send this automatically from your email tool on day ninety, as long as every reply comes to a real inbox and gets a real answer.

Sort the answers into four groups

Replies tend to fall into a few clear groups, and each needs a different response. Read each reply and decide which it belongs to:

Happy and getting value

Thank them warmly and ask what made the difference. Later, these members are good people to ask for a testimonial, a referral or help welcoming newcomers.

Happy but stuck

They like the membership but are not making progress, often for lack of time or direction. Suggest one specific next step that fits their situation, and follow up in a couple of weeks.

Mismatched

They wanted something your membership does not offer. Point them to anything relevant you do have, and be honest if it is not a good fit. Helping someone leave gracefully protects your reputation and saves them money.

Reporting a problem

A broken link, a confusing section, a billing question. Fix it quickly, tell them it is fixed and thank them for letting you know.

Reply to every answer

A check-in that disappears into silence teaches members that you did not really want to know. Reply within a day or two, even if only briefly. Here is an example for a “happy but stuck” reply from the bookshop membership:

Hi Felicity,

Thanks for being so honest. It sounds as though the event-planning lessons made sense but finding authors has been the sticking point. Many members found the Author Outreach Templates the fastest way in; the first one takes ten minutes to adapt. There's also a members' thread where shop owners swap author contacts.

I'll check back in a couple of weeks to see how you got on.

Anselm

Put a reminder in your calendar to follow up as promised. That follow-up is often what turns a stuck member into a committed one.

Handle the members who do not reply

Many members will not answer, and that is normal. Silence does not mean unhappiness, but it is worth checking their recent activity. A quiet member who has not logged in for a month may benefit from a second, shorter note a week later:

Hi Rupert, just one question this time: is there anything getting in the way of using the membership? Even a one-word answer helps.

Active members who did not reply are probably fine; there is no need to chase them.

Look for patterns across check-ins

Individually, replies help you keep one member. Together, they show you what to fix. Keep a simple running list of themes, such as “too much content, not sure where to start” or “wants more live sessions,” with a tally next to each. Review it every month or two. If the same theme comes up repeatedly, it belongs on your list of improvements, and it often explains the patterns you see in the second-month slump.

Set up your check-in

1. Write a short, personal check-in email with no more than three open questions.
2. Schedule it to send automatically around day ninety, with replies going to a real inbox.
3. Reference the member's original goal if you have it.
4. Sort each reply into one of the four groups and respond within a day or two.
5. Send a single follow-up to non-responders who have gone quiet.
6. Keep a tally of recurring themes and act on the most common one.