How to Re-Engage Old Leads & Past Clients

1. Start with a Genuine, Agenda-Free Check-In

Some of the best re-engagement conversations don’t start with products at all—they start with simple, human connection. A warm check-in can feel far more natural than a sudden push for a review or a sale.

• “Clients like to know you care; There are times to call for appointments and times to just check in with them. I love to call and just say hello without an agenda to set an appointment… just a simple call to remind them you are there and thinking of them goes a long way.” — John Ruffo
• “Good morning. It’s been a while and I would like to catch up and reconnect. I am sure much has happened, with me too. I look forward to connecting soon. Would you prefer Teams or in person? I would prefer in person. May be a coffee or lunch. Please let me know, talk soon.” — Sal Filippelli

These touches work because they are relational, not transactional. You’re reminding them that you’re still in their corner—and leaving space for them to ask for a review or a meeting if they’re ready.

2. Use a Steady Contact Rhythm, Not a One-Time Blast

Most old leads didn’t say “no forever”—they said “not right now.” A consistent, light-touch rhythm helps you stay present so that when life changes or priorities shift, you’re the first person they think of.

• “Regular, 4 times per year mailings. A phone call at least once per year with an offer to meet.” — Stephen Melancon
• “I still like to use a short letter, given that we have laws in Canada about contacting via phone and email if the prospects are dated.” — George Malmstrom

A simple annual pattern—quarterly mailings plus at least one personal call—can keep you on their radar without overwhelming them. In areas with stricter contact rules, a short, well-written letter can still do a lot of quiet work over time.

3. Match Their Preferred Channel and Meet Them Where They Are

Re-engagement feels more natural when you show up in the ways they already like to communicate. If they’re a texter, text. If they’re an email person, email. If they’re a handshake person, catch them in person when you can.

• “The way I do it depends on how we have communicated in the past. If they like texting, I’ll send them a check in text. If they like email, I’ll do that and if they prefer a phone call I will do that. With the Knights we go to council meetings, so a lot of times I’ll see someone at the meetings and talk with them afterwards. So, for me it's very much how I have communicated with them in the past and if I see them at a meeting or even at Mass. I also have a file follow up system that I use so I know when certain people have requested a call back and I’ll do that.” — Richard Vosler

When you honor how they like to communicate, you remove friction and make it easier for them to say “yes” to a quick conversation or review. For fraternal clients, this often happens in natural settings—council meetings, parish life, or community events.

4. Offer a Clear, Value-Driven Reason to Reconnect

A generic “just checking in” can work, but a specific, client-focused reason to talk is even stronger. Compliance updates, beneficiary standards, and life changes all give you a natural excuse to reach back out.

• “An email followed by a call if no response: ‘It’s a good time to review your policies to ensure everything is in good order.’ Or, ‘The standard for identifying beneficiaries has changed since your policy was issued. When can I drop by to bring you back into compliance?’” — Joe DeMarco

Framing your outreach around protection and compliance keeps the focus on their best interests. You’re not chasing a sale—you’re helping them avoid gaps, outdated beneficiaries, or missed opportunities.

5. Use Soft Follow-Up Language That Respects Their Timing

Old leads and stalled cases can still be excellent prospects—just not on the timeline you originally hoped for. A clear, professional follow-up expectation can keep the door open without making people feel pressured.

• “I use [this] when first working with a prospect who has needs that I can service and may be verbally indicating they want to move forward on some topic. I share this, specifically, after I have given them ‘homework’ to do or gather and get to me. ‘Please know that I will professionally follow-up with you two to 3 times.’ ‘If I do not hear back from you, that’s okay. I know that this is not something you can make a priority at this time.’ ‘But when it does become a priority, please know that I welcome your contact ~ whenever that happens.’” — Jeffrey Huenniger

This kind of language removes the guilt and pressure from both sides. You’re clear that you’ll follow up. You’re clear that it’s okay if they’re not ready. And you’re clear that the door is always open when the timing changes.

6. Build a Simple System So Nothing Slips Through the Cracks

The biggest difference between agents who occasionally re-engage old leads and those who consistently do it well is not personality—it’s process. Even a basic tracking system can turn “I should call them sometime” into action.

• “I also have a file follow up system that I use so I know when certain people have requested a call back and I’ll do that.” — Richard Vosler

Your “system” doesn’t have to be fancy. It could be a CRM, a spreadsheet, or literal paper files—but it should include last-contact date, promised follow-up date, and preferred channel. Then block a weekly “re-engagement power hour” to work through those names.

Final Thought

Old leads and past clients represent one of the warmest, most efficient pipelines in a fraternal practice. When you combine genuine check-ins, a steady rhythm of contact, channel-matching, clear reasons to reconnect, soft follow-up language, and a simple system to track it all, re-engagement stops feeling awkward and starts feeling like what it truly is: ongoing service.

You don’t have to implement everything at once. Start small—pick one or two strategies that fit your style, and build from there. Over time, you’ll find that more of your “old files” turn back into active conversations, reviews, and relationships.

Thanks to all who contributed—especially those quoted:

Joe DeMarco • Stephen Melancon • George Malmstrom • Sal Filippelli • John Ruffo • Jeffrey Huenniger • Richard Vosler