Questions to ask in your first emails

By  •  Updated: 01/13/16 •  4 min read


Hi, this is Steve Pratley here with another marketing quick tip.

I’ve been looking at the advice from a few other email marketing copywriters and people who send out automated emails and autoresponders.

One of the things that keeps cropping up time and time again is a bit of advice that early emails that you send out to your prospects, after they sign up to your list, you should ask them a question about what their challenges are.

Which sounds useful on the face of it, it’s there to try to understand where the pain points in your market are and to develop your products and services around that.

I think that’s all well and good, but I think there’s a weakness in it.

The weakness is that it means that very early on in your relationship, you’re asking your customers to admit the negative stuff going on in their lives.

You’re trying to ask them about where they’re failing and where they’ve got problems, and really in the early days you need to be developing some rapport and empathy with them.

There’s another step that I’m trying to put into more of the campaigns that I’m sending, which is to ask a more positive question when somebody first signs up.

Ask them what’s exciting in their world, what’s going well, what’s working for them.

That’s not going to get you the same feedback that the other question is, but it’s going to get you a lot more responses and it’s going get you talking to customers in a lot more positive frame of mind.

Then once you’ve uncovered that, then you can ask the question about what are the challenges.

What are the things stopping you from getting to that goal? What are the exciting things that should be happening in their life but aren’t because there are difficulties that they have to overcome?

They might be technical hurdles, they might be struggling to get finance, they might just be struggling with time management. All kinds of things get in the way of the exciting stuff that people are trying to achieve.

Reality gets in the way.

Try turning this into a two step question, get your prospects off on the right foot and understand what their goals are before you start asking about what the problems are in them getting there.

Firstly, I think you’ll get a better response. I’ve certainly seen that in the first few tests that I’ve done.

Although we don’t have huge numbers going through yet. I’ll report back on that in a few weeks.

I think you’ll get a better response, but you’ll also get a more positive relationship with your customers, where they don’t feel like they’re having to bare all within the first couple of emails.

Once you understand their objectives, and you can talk to them about what the barriers are there, you’ve done something else, you’ve helped frame their pain against the positive.

So “I don’t have enough time”

Yeah whatever. Nobody has enough time, but, “I don’t have enough time to build the business which is going to allow me to sack off my day job.”

All of the sudden you’ve got some pain there and you’ve got something which is that pain is going to carry on if they do nothing.

You’ve taken a frame by juxtaposing it against their dreams and their objectives so that that difficulty that they have has now become bigger. You’ve also got them in the right frame of mind by talking to them about the positive things they’re looking for before they get to that point.

If your welcome series and email autoresponders start off with the question about reply to this and tell me what the biggest challenges that you’ve got are, try just adjusting that.

Try to maybe just test a portion of your emails and see what people are actually aiming for before you ask them about the hurdles that stand in the way of achieving those goals.

I’m going to post this video up in a few places, but if you want to go to the blog at, I’d love to hear your feedback, see whether you’ve tried this in the past, see what other questions you’re asking to uncover your customer’s pain and challenges, and if you test this against your list, I’d be really interested to find out how it works for you.

Stephen Pratley

I build email lists, that grow into one-man businesses.