You probably have leads that you haven’t messaged in a long time – could be months, or even years. Now you want to restart the conversation, but there’s one big concern on your mind…

What if you come across like one of those people who messages others out of nowhere to “catch up”, but instead spends an hour trying to hard sell you a new insurance policy or MLM scheme? The lead will certainly think twice before responding. 😬

So after a long period of silence in your conversation, how do you connect with leads without sounding like have a hidden agenda? Here are our three best tips on how to reconnect with your leads in a way that helps you revive the conversation AND your sales process.

Should you even message them at this point?

Yes! You should try to re-engage the leads, even if it’s been quite some time (unless they’ve explicitly told you not to message them again). Ideally, there shouldn’t be a long pause between now and your last conversation with the lead in the first place. And you can prevent this by setting up a simple system for timely follow-ups.

But now that we’re here, the first thing you need to know about reigniting “cold conversations” is this:

Tip 1: The longer it has been since you last contacted the lead, the more personalised and relevant your next message needs to be.

It’s best not to send the lead anything too generic, even if it’s just to wish them happy holidays. Remember, they might not even remember the last conversation they had with you.

In fact, let’s say it has been a really long pause, like two years. Your re-engagement message has to be much more personalised than just addressing the lead by their name. A simple “Merry Christmas, Anne!” might not be enough to rekindle the connection.

Instead, you could add any small details you remember about the lead, such as their hobbies, their family member’s names, or even a shared experience. Here’s how this would look like in a message.

Example 1:

Merry Christmas, Anne! 🎄 Wishing you, David, and Jane all the best this holiday season. Here’s to a wonderful new year ahead for you and your family.

Example 2:

Happy Birthday, James! 🎂🥳 Hope you get to eat all the tiramisu you want today.

How can you move the conversation towards a sale, without sounding like you’re just reconnecting to make a sale?

Sometimes you want to re-engage a lead because you have a really good promotion or product and you thought of them. But after such a long time, initiating the conversation with anything sales-related just doesn’t feel right.

Many salespeople will try to bait the lead into a pitch by asking them about their life first, like “Hey Lisa, it’s been so long since we last talked! How have things been? How are you?” Avoid that! ⚠️

Nobody likes to engage in random small talk… only to be hit by a sales pitch immediately after what they thought was a friendly catchup. Some won’t even reply because it’s such a common tactic that they can anticipate the pitch far ahead. So what should you do instead?

Tip 2: You can defuse the potential awkwardness by being upfront about why you’re reaching out to them again.

That’s not to say you should just jump straight into business. Take a look at this message (it’s not a good example):

Hey Chris, hope you’re doing well! I’m excited to share that we have a newly-launched duplex project available for viewing, starting next week. Let me know if you’re interested to schedule a viewing.

– Lisa, ACME Realty

The message looks fine, but it doesn’t feel relevant to the person. And if you’re sending this after a YEAR of not talking to the lead, the message just falls flat. It sounds like all the unsolicited sales and marketing messages a person receives every day.

Tip 3: How to know if your message is personalised enough? If it can be sent to different people and still make sense, it’s probably too generic.

When you’re trying to reconnect, you should add more details and context that’s specifically relevant to the prospect. In some cases, simply stating why you remembered to message them could even help you score points with them. For example:

Hey Chris, hope all is well with you and Sarah. I remembered that you were looking at 3- bedroom units in the Edenbrook area last year, but there weren’t any units available that came with a balcony.

There’s a brand new project that just launched in Edenbrook, and I immediately thought of you as every unit comes with a spacious balcony overlooking the city. Would you like to see the floorplans?

– Lisa from ACME Realty

Throughout the message above, we added small personalisations that gives the lead more context and motivation to reply. Especially because it’s so relevant their personal motivations and preferences. Moreover, you’re also showing them that even after all this time, you still remember the lead as a unique person. Not just a contact you’ve added to your occasional bulk-messaging campaigns.

But how do you personalise if you don’t have that information?

Long story short, details are important. If you want to maximise your chances of reconnecting with a lead, you need to be relevant by personalising your messages with them. But what if you don’t actually remember these kinds of details about your leads, since it was such a long time ago? Something that could help you here is a mobile CRM tool like Privyr.

It’s like a supercharged phonebook for all your leads, and you can even add notes to specific clients, calls, and meetings that only you can see. The next time you view a lead in the app, you’ll have all the context (and templates) you need to quickly create a personalised re-engagement message, no matter how much time has passed.

Before you go…

Restarting conversations after a long time is hard, but remembering to follow up with all your leads on time is arguably harder. If you’ve ever thought about automating your follow-ups, read this first. We talk about whether it’s a good idea to schedule WhatsApp messages.

Want sales tips and tricks delivered to your inbox?

Subscribe to Privyr’s newsletter, trusted by over 50,000 salespeople, marketers, and small businesses.


Shuni spent way too much time on Yahoo Answers as a child. Now she writes content to help people make better use of software and marketing tools.