I’m pretty sure that we all know how important email follow-ups are. It’s one of the most important tactics to implement when it comes to trying to close a deal through cold emails. 

From our experience, I would say that it’s quite rare that you can close a sales deal on the first email or contact. Sales is like everything else in life that takes persistence and follow-ups play a major role in that.

It takes multiple emails because that’s what builds trust and what will help both parties in the long term.

Email follow-ups aren’t just important for sales, but it is important for accomplishing a lot of other things in life such as looking for a job, trying to get in contact with a celebrity and more.

The focus of this article will be on sales and some tactics for getting creative with email follow-ups. It’s a tough thing to do because this is where you have to get out of your comfort zone. You can’t be scared to follow up, but being over aggressive can ruin a deal as well.

So the main question is what is the best way to send out those follow-up emails that work?

Rarely do I see any sales training programs teaching people how to do email follow-ups. Too many traditional sales training programs stick with old school scripts, but when it comes to email follow-ups, you have to think outside the box and that’s what this article is for!

What do I send after that first email?

Most sales experts recommend reaching out to people 5, 7 or even 10 times. Actually, well-known people in the sales industry like Steli advise you to never stop following up until you receive a solid answer.

The hardest part about this is coming up with creative cold email follow up content.

If you’re following up 10+ times, that might make you want to pull your hair out….

This is where creativity kicks in..

Here’s a quick guide:

Email #2 (the first follow up):

We don’t like to get too creative for the first follow up. This is because a lot of times prospects will open emails on their phone and then forget about them.

You can also check to see if they’ve read your email…

This can easily be done using a tool like Quickmail. With Quickmail, not only can you track emails, you could also automate your email follow up which will save you a good amount of time. We believe in working smarter not longer. 

This is important because some people wake up in the early morning and check their email on their phone, but then forget to respond afterward. That’s a good sign to send out your first follow up email.

A prospect might get up, check the email in bed, read and acknowledge how awesome your service could be for them, and mark as unread on their gmail.

What we recommend here is to remind them with a simple follow up.

For instance:

“I sent you an email a few days about xyz, and I was wondering — did you see it? Want to make sure it didn’t get lost in the shuffle.”


“I’m sure you’re busy and hope this didn’t get buried!”

Or even


Yep, you’ll be surprised how some of these basic follow ups work. If you’re in a good position, 50% of the ones that didn’t respond will respond to these simple follow up.

Email #3–5: Be professional

This is where we like to get a little more creative, but no worries NOT too intense yet.

The goal here is making the content personalized — don’t say the same thing again.

Never send a “just checking in” email on the third contact — it’s too generic and doesn’t work.

Take a minute and check out the prospect’s twitter. Then you can send something along these lines:

“Hey, I noticed you haven’t been tweeting too much lately, but I did like the last one you posted about zyx. I agree with what you were saying. Checking in to see if you received the last email.”

The common theme with all of these is  to  find something personal to reach out to contacts about, then reach out to them about it.

This can also be a new feature that their company released or maybe a new blog post that they wrote. Find something personal and remember you do not need to be too aggressive, but you do need to be creative for this one.

Do your research kiddos.

You want to keep emails 3–5 personalized and professional. Use these messages to see if they’re interested or paying attention.

One thing I love to do is to subscribe to their email newsletter and see if you find anything interesting. Companies release new updates, blog posts, mentions and tips in their email newsletter all the time. Take advantage of this!

I also like to subscribe to the company and see what their first subject line is. Here’s an example:

I’ve worked with a company that does SMS marketing in the past. When you sign up for their newsletter, the second message had the subject “Can we chat?”

I took that email and said the same thing as the subject line of his fourth follow up:

“Can we chat?”

My first line in the email was:

“Hey, did it work? I got this subject line from your newsletter.”

The prospect responded and asked for more info on what we did before turning into a customer. He’s been with us for over 7 months now.

The goal with these emails is to be super personalized. 

Personalization is one of the key features within Quickmail. You can personalize the email using attributes within Quickmail to make the email more personalized and more effective.

Keep in mind this lesson from The Art of War:

“Know yourself, and know your prospect, and you’ll win 100 battles.”

Email 5, 6, 7 and beyond: Get creative

If you’ve pinged a client 4 or 5 times using all of the tactics above and you still aren’t getting a response, then you have to get creative in order to force them to respond.

This is when we start sending animated gifs or elephants….

Try sending something that’s a little bit corny with a bit of humor.

Humor works in sales when done correctly. You don’t have to be old school and professional, in fact — that hurts you a lot of the time.

Putting in a bit of humor is a great way to show personality and get the prospect to respond.

One a Friday, I will send a GIF with an elephant partying that says:

“Happy Friday!”

“I tried reaching you — this is probably my 5th time — and I know you’re super swamped, but maybe we can make something happen next week.”

You can go even cornier:

I used to send a picture of a different elephant with “I don’t bite” as the subject line.

“Hey James, I don’t bite :)”

A short message like that with a funny gif gets us responses 8/10 times.

The goal here is to get any response — a rejection means that you don’t have to worry about the prospect anymore, and you’ll get solid feedback on the idea.

To find gifs, you can either search google or use a site like Giphy. There are also chrome extensions you can use with your Gmail to find funny pics and GIFs. No excuses!

Follow Up After A Month

Let’s say they haven’t responded at all even after the hilarious gif attack… what now?

Send them a quick email like this:

“Hey, I reached out to you initially about a month ago. Wanted to ping you again in case your mind has changed. Are you interested at all in zxy?”

I’m not a big fan of automated follow-up, but the truth is that it works really well. It also saves a good amount of time. Luckily this can be set up easily within Quickmail. Give it a try and you’ll be surprised at the results.

The Breakup Email

Once you’ve gone through this whole process it’s time for a hail mary. It’s time to send the breakup email.

Here’s an example:

“Hey, I tried reaching you 10 times now and I still can’t get through after a couple months. Maybe we’re not a good fit. That’s ok, please reach out if you need any help.”

It doesn’t work all the time, but you have no other options at this point.

A good breakup email triggers the prospect’s emotions, and sometimes you get a response.

I got an email from Hubspot after 6 months of not responding that went:

“r u ok? :(“

There’s no way not to respond to that.

That shows how well versed they are in sales as well

Hammering everything together

Cold email is not easy. It’s a craft that requires practice, especially when it comes to follow-up emails. The more you do it the better you get at it and the faster it becomes a natural instinct that requires little thinking.

Make sure, you take advantage of all the tools out there to make your life easier. In order to achieve maximum results, you would want to leverage the best cold email technology that will provide you with automated drip emails, email tracking, and an all in one platform to automate your sales workflow. 

Don’t reinvent the wheel when there’s already budget-friendly solutions out there.

🔥 Ready to start sending automated, scheduled follow-ups? Try QuickMail free for 14 days (no credit card required).