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4 questions you can ask to start conversations with cold leads and past customers

Cold leads and dead conversations… Every business has them. People you somehow forgot to follow up with. Others who ghosted you. Some who you never contacted in the first place. Even past customers who you haven’t heard from in a while.

But those stalled conversations aren’t lost causes or wastes of time. Thinking otherwise is basically admitting you don’t want to make easy money. By asking the right questions, you can restart conversations with leads and customers and have a consistent back and forth.

Take Krista Mashore Coaching for instance. Their sales team used Skipio to reboot conversations with cold leads and made almost $49,100 in a single month.

Check out the types of questions you can use to get those conversations going and you’ll quickly see a boost in responses when you try them. Each one helps you optimize your lead nurturing.

Are you still interested in ________?

If you know someone originally reached out to you because they were interested in a specific service you offer, just ask if they still need help with that thing. If it’s been long enough, they may have found a different business to solve their problem. But if it hasn’t been that long or it’s an evergreen problem that you solve, you might get lucky.

Asking this type of question is also effective when someone had an appointment scheduled with you but then no-showed or cancelled. It’s this type of question in particular that helped the Krista Mashore Coaching team. By specifically reaching out to people who had appointments but never made it there, they got so many leads back on the calendar and ready to buy.

Do you still do ________?

If it’s been a while since you reached out to someone, it’s going to be beneficial to know what they’re currently working on before you automatically start pitching them. Especially for those doing B2B sales and marketing, check if someone is even still in the same business or industry.

One of Skipio’s most successful re-engagement campaigns focused on cold leads from our fitness vertical.

We enjoyed the surprisingly fortunate problem of generating too many leads and not having enough manpower or time to have full conversations with everyone. At one point these people needed a texting and engagement solution for their gym or personal training business.

But because it had been long enough since we’d last communicated and because these types of micro-businesses can go through changes very quickly, we decided that before asking anything else we would ask about their business. This is basically what our first message said:

Hey [First Name], this is [My First Name] with Skipio. Do you still own your gym?

This message helped us quickly filter our list of cold leads. Depending on their answer, we then sent relevant messages. For instance, for people who no longer owned a gym, we sent them a short message saying, “Well, if you ever need a free business texting service, use this link to sign up for Skipio.” Those who were still in the fitness industry received specific messages about their current communication tools and process.

Overall, this process helped us restart hundreds of conversations, many of which resulted in brand new Skipio accounts being created. And all it took was a single personalized question to get it going!

Did you know we have ________?

This sort of question, with a brief explanation of the product, feature, or service, plays off the fear of missing out, which you probably know is a really strong emotion for driving customer action. Just make sure the blank is filled in with product or service tailored to the leads you’re messaging.

Because if they didn’t know about it and you’ve done a good job targeting the message, the lead will start thinking about how they probably do need that thing. And not having it means their life will be harder in some way.

You may also want the message to focus on a sale or special offer. So instead of just framing it as, “Did you know that we have this cool thing?” frame it as, “Did you know that for a limited time you and you alone could get cool thing for a screaming deal??”

Creating urgency and portraying exclusivity prompt people to take action. When done right, they’ll happily ask you to tell them more.

Have you seen the latest ________?

Time for a little content marketing magic! Fill in the blank with a new video, blog post, app, quiz, graphic…

Share with those leads or customers something that specifically helps or benefits them. Again, this will work most effectively when whatever you send is as relevant as possible to them. The topic of the content you send should be directly related to common problems of that persona or target audience, to any previous conversations, or to any past purchases.

Some pieces of content are more applicable to a wider range of people, but you can’t simply rely on a generic demo video, no matter how good it is. People respond best and most often to personalized outreach.

Sending content works well because it allows you an easy way to follow up no matter what. If someone doesn’t respond to tell you that they watched or read whatever you sent, that’s the perfect opportunity to ask them about it. And if someone does respond after you send it, you’ve got a revived conversation.

More tips for cold outreach to leads and customers

One thing you hopefully noticed is that even though each question could be answered with a simple yes or no, they still leave room for people to say something more. They still start conversations. Above all that’s what you need to remember when reaching out to cold leads and old customers: It’s about starting a conversation and rekindling that connection.