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The important part is getting the readers to reply. If you can start a conversation with a prospect, even just over email, your chance to close the deal skyrockets.


You and I both know you aren’t a spammer. You’re a service professional or perhaps a salesperson. But given the fact that you need to generate leads and make sales—and given how easy it is to send email—it’s tempting to just blast out the emails and see what happens.

That approach is completely counterproductive. Yes, you want to send out 20-50 prospecting emails a day, but sending them is not the important part. The important part is getting the readers to reply. If you can start a conversation with a prospect, even just over email, your chance to close the deal skyrockets.

So, if getting a reply is the goal, it’s absolutely worth taking an extra two minutes to customize your introductory emails. Getting someone to reply to your cold email is challenging. Here are five tips that will help.

  1. Initiate a conversation based on something they do or just did.

Take a minute and look up the prospect online. Did their company do something recently? Did the prospect? Did their quarter just end? Did their local sports team just win? Find something relevant to them.

If you are responding to inbound behavior or a request, be as specific as possible about what triggered your email. Put this trigger in the subject line so they know you are writing about them.

  1. Be timely.

The shelf life of any activity is getting shorter and shorter, and the value of being timely is higher and higher. If you can reach out within a minute after a prospect does something, that’s great. Within an hour—good. Within a day—OK. Within a week? That’s borderline. If your response time is longer than that, find something else to write about.

  1. Give them value.

You made a first impression with the trigger event. Now build on that by giving them something of value. Share a great article, website, video, or cartoon.

In 99% of the cases, what you share should not be about your company. Your marketing department should be churning out collateral and white papers, but those reek of self-interest. In order to establish credibility, you have to offer something that doesn’t help you in any way. It’s all about them—your prospect. Go find something that would genuinely help them be more successful, and offer that.

  1. Invite prospects into a conversation by asking a question.

Having offered your prospects something valuable, you can then ask them to engage.

The more specific and straightforward your question is the better. You want to make it easy to reply, and you want to make sure they clearly see the benefit of replying.

Ideally, your question links the resource you offered with the services you provide or are selling. But be careful: don’t be too obvious. If I sent out the consultant comic above, I might ask, “Have you had any success with bringing in outside consultants? We’re growing quickly over here and looking for resources or best practices to scale quickly.”

  1. Follow up with recipients.

If you can track when the recipient reads or forwards your email, it is worth sending a follow-up email within 24 hours. Even without this insight, you should make it a practice to revisit your prospect list at least four times by email. The good news is that by continuing to offer something of value to the start of your messages, you’ll begin to be seen as a generous and trusted resource instead of just another salesperson.

It’s tempting to meet your daily goals by blasting through as many emails as you can. That’s short sighted. It burns good leads, and it burns you out. Think instead about how you can start a timely conversation and how you can provide something valuable. You’ll find yourself having more genuine conversations and, by extension, closing more deals.

About the author

Matthew Bellows

Matthew Bellows is Founder and CEO of Yesware. Matthew brings more than 10 years…

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