How do I start a conversation with a prospect?
Apr 30, 2025
Here’s something the LinkedIn gurus don’t tell you: you’ll never close a deal in DMs. Sure, you might get pretty close but the sale will rarely ever be made this way. That’s one reason, among many, that starting a prospect conversation with a sales pitch never works. It doesn’t matter how long you’ve been connected with that prospect, how many of their posts you’ve liked or even if you’ve learned the name of their dog, DMs are not where sales happen.
However, LinkedIn DMs are an important part of the social selling process. They’re the final step between you and that sale. So, you need to know what gets you past this step and onto the sales call. It all begins, unsurprisingly, at the beginning, with the first DM you send your prospect.
Don’t pitch-slap your prospects
Forget DMs for a second, forget LinkedIn and think about the last event you went to. How did you approach people at these events? Did you walk over, business card first and launch into a pitch? Probably not. And, if you did, how did that work out for you? The most you’ll get from approaching someone like this is polite humouring, but all the time you’re talking, they’re thinking about how to get away.
On LinkedIn, they don’t have to humour you, they can simply not respond. If you know that approaching people this way in person doesn’t work then you already understand how LinkedIn DMs work the same way. You can’t send a pitch as a first message.
Start a DM conversation the same way you would any conversation
Ice-breakers exist for a reason, they’re not just for team-building days in the office. So, even if you’re not the most social person, you can find common ground to build a conversation on. The best part is, it’s easier to do on LinkedIn than it is in person. Your prospects' content and profiles will be filled with information you can use to start a conversation.
Instead of introducing yourself and explaining what you do, introduce yourself and ask what they do. Yes, it really can be that simple. However you decide to start the conversation with your prospect, make sure they are the focus. Use a recent post they shared, a comment they left or an update from their profile as a starting point.
Even the most limited LinkedIn profile will have something you can use to start a conversation with your prospect. Eventually, the conversation will start to move towards their pains, your reason for seeking them out but that still isn’t an invitation to start pitching. Ask open-ended questions, learn more about their pain and you’ll naturally move towards booking in a sales call.
Nurture your network
LinkedIn DMs shouldn’t be the first contact you have with a prospect, not even after connecting with them. There’s nothing more jarring (and off-putting) when you accept a connection request and are instantly pinged with a message. Connect with them, explore their profile, engage with their content and find your conversation starting point.
Connect, nurture, message. That’s the key formula to starting successful conversations with your prospects. Don’t have the time to build these connections? The PINAKL team can find and nurture these connections for you, priming your prospects so they’re ready for the sale.