When follow-up emails make most sense (with real-life examples)

In a dream world, every single cold email you send would get an immediate (and positive) response.

Pinch yourself, because that’s hardly ever reality. More often than not, you need to follow up—and popping back into somebody’s inbox can feel even more anxiety-inducing than your initial outreach.

How soon should you check in? What should you say? How many times can you follow up? Is it even worth it? Are you being a pest? Here’s the truth: You absolutely should follow up. It’s a normal part of the cold emailing process, with several commenters on one LinkedIn poll noting that follow-up efforts are often more important than the cold email itself.

Need some tips and inspiration? Here are six hard-won lessons from side hustlers and business owners—and some stories about when their follow-up emails landed a win. 

Lesson #1: Stay (super) persistent

Cold emails have a notoriously low response rate, with some estimates stating the average response rate is around 7%. Ouch. That’s not meant to discourage you, but rather to emphasize that following up is non-negotiable.

And that doesn’t always mean “circling back” just once. You might have to practice patience and persistence. That was true for Margaret Etudo, a freelance medical writer who says she followed up roughly every two months for over a year (yep, you read that right) before finally landing a freelance writing gig with Forbes Health. 

“I’ve pursued clients for over a year before they said yes to a project,” echoes Tess Van Ee, who’s also a freelance writer.

Of course, the trick here is to strike a balance between being tenacious and obnoxious. Previous responses are your best indicator as to whether it’s worth checking in again or you’re better off throwing in the towel.

If you’ve received replies to previous emails (think things like, “We don’t have the budget right now…” or, “Maybe next quarter…”) then you’re justified in keeping in touch. But if it’s been nothing but radio silence after one or two follow-ups, it’s probably best to move on. 

Lesson #2: Practice some empathy

Not getting a response to your cold email can feel personal. Why don’t they like me? Why are they being so rude? How hard is it to just answer one email?

Check your ego and put yourself in the other person’s shoes. When the average person receives over 120 emails each day  (you’ve likely dealt with your own swamped inbox before), chances are you’ve probably ignored a couple messages or simply forgot to respond amidst the mayhem.

The same is true for the people you’re reaching out to, and it never hurts to give them the benefit of the doubt. Rachel Ciervo, a website copywriter, says it’s a strategy that helped her book a call with a referral after one follow-up. “It was the end of Q3 when I was connected with her and I figured she must have been busy. Spoiler: she was!” Rachel shares. “I think what helps is acknowledging or at least respecting that our clients and prospects are busy and making the follow-up email a super light touch—no 'schedule a call now!' CTA.”

Here’s a quick follow-up email sample to show you what this can look like:

It’s short, low-pressure, and empathetic — all of the makings of a solid follow-up email. 

Lesson #3: Connect on something specific

Sometimes a quick and general follow-up email can do the trick. But other times, you might be better off including something targeted and memorable, like recent company news or a call back to a previous interaction.

“A follow-up email got me a writing contract I’d been chasing for a while,” says Sarah Brady, a finance writer, who says she followed up twice before but decided on one last, personalized attempt. “My email referenced the content they’d recently published about the pandemic, and I discussed how I was uniquely qualified to cover the topic because I had helped so many consumers recover from the 2008 housing crisis.” That approach paid off—almost immediately. “Within minutes, I had a response and began the process to get a contract,” she adds.

Terry Schilling, a copywriter, did something similar with his follow-up email’s subject line. “I landed a workshop with a large company with the subject line, ‘How’s my timing?’” he shares. “I knew the recipient well, we worked together in the past, and talked about doing the workshop for her sales team,” he explains, noting that they loved the idea but they weren’t ready to move forward. “Since the timing wasn’t right before, I led with that and offered a benefit of the workshop.” 

Lesson #4: Set a clear expectation

Tired of the murkiness and uncertainty of cold emails? Set some clear expectations in your follow-up. This can take shape in a number of different ways, for example:

• Outlining a deadline that you’ll take your idea elsewhere
• Asking if there’s a different or better time you can check in
• Stating that you’ll assume no response by a certain date indicates no interest

Those make the next steps clear for both you and your contact, and it gives them an easy out if they need it. Plus, it’s a way to bring some more clarity to an otherwise ambiguous process. When you explicitly state your expectations, not getting an answer is your answer (even if it stings a little). 

Lesson #5: Be strategic with your timing

Timing is everything, particularly with cold outreach and follow-up emails. But magically landing in the right place at the right time isn’t really a scalable strategy for your business or side hustle.

“There’s good timing luck—and there’s great timing strategy,” notes Amy Knightley, a marketing strategist who’s hired service providers from cold emails. “I’ve spent the most money with business developers who asked about my budgeting and busy seasons and tailored their outreach accordingly.” “When they tell you it isn't in the budget, ask when their budget planning cycle begins and what would be important to show those stakeholders,” she advises. “Then prep and schedule that next pitch.”

In short, good timing isn’t something that has to happen to you—you can create it for yourself. 

Lesson #6: Keep it short

Follow-up emails can feel agonizing—even more so when you feel the need to write five paragraphs stuffed with selling points and all of the context of your previous conversations.

Here’s some good news: You can keep it short, especially if you reply within your original email thread. Even just a few words can be enough to bump your email up in someone’s inbox and encourage a response. Terry says it’s a strategy he uses a lot. His follow-up message might even be just a quick:

“People are busy,” says Terry. “There’s a chance they saw the first message but life and work got in the way. No need to write another novel to get attention.” 

Ace the art of the follow-up

It’s tempting to think magic will happen after sending just one cold email. But in all likelihood, sometimes you need to check in a few more times to get a reply.

Research shows that your first follow-up yields the highest response rate, so put some of these strategies to work to resurface in somebody’s inbox with a thoughtful and effective message.

At the end of the day, wishful thinking won’t get you a response—but your follow-up email just might.