How do you write an effective but gentle reminder email? - reminder email template

There are two problems with reminders.

First, it is a guilt trip – no matter how much you sugarcoated it with niceties, you are pointing out that your recipient didn’t do what he/she was supposed to do. So the first thing they feel after opening your email is a strong negative emotion. And as good doctors say: “neurons the fire together, wire together…”, meaning that now you, your product, and your company are in the same mental emotional box with stubbed toes, missed doctor appointments and milk gone sour. You don’t want to be in that box.

Secondly, in a sales and marketing environment, usually you are asking for attention, time, a response, information, etc. from people who don’t owe you anything. Usually, they are more senior than you, busier, and better paid. You haven’t provided value that your recipient consumed and therefore feel indebted to you yet. You have no leverage. And that compounds the first problem to n’th degree.

So in the words of @mjhoffman: “don’t make references to previous failed attempts” because they don’t bring anything of value to the table and therefore don’t increase your chances of getting a response.

That’s a long rant on why not to do reminders the way 99% of people do them. Now a short rant on how to do them right:

Hi John,

We are sponsoring ABC forum in New York on 9/15. It’s sold out but I have two complementary tickets for you and someone on your team. Looking forward to seeing you there.



P.S.: Hey, any news on the proposal your team was preparing for us?


Hi Mary,

I noticed you have a number of open positions in your SDR team. That’s awesome news that your company is sustaining high growth, congrats! Btw, I have two former colleagues who may be a good fit, let me know if you’d be interested in getting in touch with them.

Speaking of SDRs, you probably want to make sure the CRM you just purchased from us is up and running by the time they join. Do you think you can get the signed contract back to us by Friday?



A Complete Guide on Email Subject Lines for B2B SDRs and Inside Sales Teams.

CAVEAT: This piece is SPECIFICALLY dedicated to cold prospecting emails. Some of these points may not apply for writing email copy for lead nurturing, customer success or other circumstances.


What’s the big deal with subject lines, you say?

Well, an email subject line to sales is what a resume is to job hunting.  As the latter won’t land you a job but will get you an interview, the former won’t get a sale but will persuade your email recipient to open the email so your copy has a fighting chance of scoring a response.

Now, how do we do that?

We’ll get to that in a minute, but first, close your eyes and imagine your prospect who’s about to read your subject line:

An iPhone in hand, she is sitting in the business class section of a trans Atlantic flight taxiing for take off.

An annoyed flight attendant is yelling at a passenger behind her to shut down all mobile devices.

She has 1.5 seconds to knock just one more email off her to-do list.

Will that email be yours?

Well, maybe.

People who receive tons of email have highly evolved mechanisms of dealing with information overload.

The primary tool for doing that is a mental heuristics filter that in a fraction of a second tests your subject line against the following questions:

=> Is it Important? (will not reading this email get me fired or put my life in danger?)

Yes, think primal factors: fear and greed, fight or flight response; save time and make money, that kind of stuff.

There’s a known psychological phenomenon that humans are motivated by fear of loss more than by a potential gain. In this vein, a subject line “3 reasons {{company}} is likely to suffer a hacker breach” is more likely to be opened than “How to Grow Your Revenue 13%”.

Borrowing from psychology a bit more, people usually consider themselves rational, yet there’s plenty of evidence that decisions are driven by emotional states and then justified with reason.

And what usually pulls on emotional strings? A good story. Distilling a story into a headline and a headline into a subject line is a craft and an art in itself (and a rabbit hole worthy of a separate blog post) however even thinking of that while you draft your subject lines will make them more potent, translating into a higher open rate.

=> Is it Relevant? (is it about me, my product, my company, my hobby, or my dog? Is it from someone whom I know, like, love, fear, respect, hate, resent, follow, or am related to?)

Here’s where building a connection on social media first and personalization will pay off in spades.

Put yourself in the shoes of your recipient who has a razor-thin attention span. The emails she opens first are from: her boss, her clients, her spouse, her colleagues, her admin assistant and her subordinates, not necessarily in that order.

Notice that you – a yet unknown vendor – is nowhere on that list.

Which means that your subject line needs to convey clearly that this email is not an 1) untargeted sales blast or 2) a “nice-to-know” informational snack or 3) spam.

Instead, it should scream that this email is squarely about her, for her and for her only.

=> Is it Urgent? (Will I die or wish I died if I don’t read this email right now?)

For this reason, time references (tomorrow, next week, calendar, date, etc.) in the subject line work like a charm.

We must note that you can only press urgency if you have even the tiniest level of relationship with the recipient. If they don’t know you, don’t recognize your company name, don’t trust you then nothing you say is urgent to them.

=> Is it Clear? (Can I answer those three questions above without bothering my frontal cortex too much?)

In other words, does your copy help quickly and accurately classify the subject line into one or several of those three boxes?

Remember the old adage from direct marketing days:

“A confused mind always says NO.”

In our age of razor thin attention spans, it takes your recipient a fraction of a second to process your subject line. The easier and with less friction you make your subject line to hit one or several of those check boxes, the higher the chance your email will be opened.

With this in mind, don’t use a $5 word where a nickel-word would do. “Use” instead of “utilize”… that kind of stuff.

=> Is it Easy? Something that appears complex, may involve additional research, coordination with others, substantial time for reading, analyzing and responding goes into “Review Later” folder, which is a politically correct label for “Trash”.

Short copy is usually the winner. Today’s execs are suffering from ADD caused by consuming-content-from-a-firehose’itis, so write your email copy to match.

Does your subject line promise an email that’s easy to read, understand and respond to? If not, re-write it.

Or, better, write up several and A/B test for higher open rate.

=> For extra credit: Is it Entertaining? (Does this make me curious, puts a smile on my face or promises an immediate endorphin fix?)

An emotionally charged word, an unexpected juxtaposition, references to current events, celebrities, etc. will do the trick. Use with moderation and caution.

Now that we’ve covered the basics,  let’s dig in.


Keep in mind the following points when you craft your B2B prospecting subject lines with out-of-the-ballpark open rates:

A. Personalization

Personalization checks the “Relevant” box for you. It screams “yes! it’s about you… yes you! now open it”.

And this is not just hearsay. According to awesome folks at Sidekick, personalized subject lines get 22.2% more opens.

How do we write a personalized subject line?

Start writing with a persona in mind – imagine your high school classmate who did better than most in life, successful and busy – write for her.

At a minimum, include “you”, “yours”, {{firstname}}, or {{company}} in the subject line to personalize.

B. Mind the device

The whole world seems to have gone mobile. Some 40% of emails are opened first on a mobile device.  That means that subject lines that don’t fit the screen may not be the first ones to get opened, read and responded to.

So write and optimize for mobile. Send yourself your own email and see how it looks on your iPhone or Galaxy first.

C. Call-to-Action

“Get”, “Find”, “Attend”, or “Register” and other call-to-action type words could be good ways to start your subject line.

They are potent for several reasons: 1) they take guessing out of figuring what’s expected of the recipient, 2) they are formatted as a command, an order, hopefully igniting the internal compulsion to comply in the recipient and 3) as the recipient silently reads the subject line, she essentially repeating the command to herself. Very powerful, potentially, stuff.

One caveat: if your prospect doesn’t know you/trust you, these commands will largely be ignored.

D. Size Matters

But not in the way you think.

In fact, there’s a ton of conflicting evidence out there:

According to TotalSend, subject lines of 5 words or less outperformed subject lines of 8 words or more, 65% of the time.

Litmus pipes in: if you can say it in 28-39 characters then your subject line is more likely to kill it with open rates.

But Yesware says it “doesn’t matter“, which makes things doubly confusing.

My two cents: A/B test where you can. If you have a semblance of a relationship with the recipient (e.g. they at least know who you are), feel free to try a longer subject line. Otherwise, stick to 40 characters.

E. Questions?

A question is one of the most powerful tools in the arsenal of any direct marketer or inside sales rep for two reasons.

1) asking a question puts you in charge of framing the conversation. Most of the time, your recipient will be consciously or subconsciously reading the question and most of them will jump into answering it in their mind. That’s engagement. That’s what you want.


2) from an NLP (Neuro Linguistic Programming… not the other one) perspective, questions are very powerful. They are impossible to ignore because humans are hard wired to answer them – to be helpful, to be polite, to appear knowledgeable, to be defensive, etc. In most of the social paradigms – teacher/pupil, boss/employee, parent/child – ignoring a question is not an option.

F. Format

Good news first, lists and how-to’s still kill. But everybody knows that, so the tactic is a bit over-used. To sharpen this tool a bit and to make it stand out from the noise try this:

a. Plant a hook – e.g. “7 Tactics to Generate Leads from LinkedIn Groups, #3 will amaze you”

By itself, the first part of the subject line isn’t compelling enough. However, now that we mentioned that tactic #3 is special, I MUST open it, even if only to prove you wrong. Can you spell Zeigarnik effect for me right now?

b. Twist the blade – sprinkle unexpected drama, intrigue and over-board words (with measure!) – e.g.

  • “7 killer marketing hacks banned outside U.S.”
  • “How this barely legal SEO trick drove site traffic from 0 to 5mil/month”

Couple things to note:

First, you should know your audience well before attempting any of this. Unleash this on C-level Fortune 500 execs and your unsubscribes will go through the roof.

However, if you audience already trusts and respects you (as you can tell by high open/forward rates), then go for it. Still, first test on a smaller subsection of your list, keeping an eye on opens and unsubscribes.

Second, you need to pay-off your subject line in the first two sentences of your email. If you bait your reader with a juicy subject line and then proceed to rambling about how you spent your summer, he’ll feel bait-n-switched. Not cool.

G. A Few Things to Never Do

  • Don’t include Re: or Fd: to imply previous conversation if there was none. That’s just such a turn off.
  • Don’t write long emails, if it’s your first cold outreach. Even if it’s of “War and Peace” quality, it will be ignored, deleted and/or marked as spam.
  • Don’t bait-and-switch. In other words, your subject line should match your message. Ideally, you should explain your subject line in the first sentence of your email, second – tops.
  • Don’t apologize. “Sorry for interrupting your day but…” immediately puts you into a weak position. Pretend your recipient is stranded in a desert and you are offering her water.
  • Don’t fake a connection. “I was impressed by your LinkedIn profile and I thought you may want to buy some of my SEO services”. Never works.
  • Don’t use spammy words – chances are your recipient will never get a chance to see this email and your sender score will suffer.
  • Don’t do ALL CAPS.
  • Don’t do anything that prevents you from doing one thing you should do: make your point fast and ask for something simple enough that your recipient can do with minimal cognitive resources, time and friction. And craft a subject line to back it up.


These are some of the examples from people I consider experts in outbound prospecting:

Jake Dunlap

Jake is CEO and Founder of Skaled, helping startups to build robust selling engines. Previously, Jake headed up sales at Chartbeat, Glassdoor and Careerbuilder.

  • Time to meet – {date}
  • Just left you a voicemail …but thought this might be faster
  • Meeting with our CEO {location} {date}
  • Follow up from [Boss’s Name]

Find why these subject lines outperform here>>

Aaron Ross

Aaron Ross needs no introduction. Suffice to say that his Predictable Revenue is an absolute must-read for anyone in inside sales. And if you want to call dibs on your own copy of his new and improved edition, you can do that, too, here>.

  • looking for an intro
  • mutual friends with Julie Smith
  • enjoyed your recent talk on networking

More on why these are effective here>>

Heather Morgan

Heather is Founder and CEO of Salesfolk, where she creates compelling cold B2B emails that feel human and actually add value, which is why her email copy gets 2-3x more qualified leads than regular emails.

  • how competitive is {{company}}’s sales team?
  • 10x {{company}}’s traction in 10 minutes
  • Question about employee loyalty at {{company}}

You can read why these subject lines pull unbelievable response rates here>>


LeadGenius is an end-to-end sales-acceleration solution that provides sales organizations with a more efficient way to prospect. Not only they offer an amazing service, they also put out unique and helpful content for inside sales warriors.

  • Sample leads for {{company}}
  • Potential leads for {{company}}
  • I found you through {{FirstName}} {{LastName}}

Find why these subject lines outperform here>>.

* * *

Now, I am not an expert… and I don’t play one on TV. 🙂

But I do send a lot of B2B emails, as the CEO and Founder of ExecFile (a stealth-mode sales enablement service – think Sales Navigator on steroids).

And these subject lines are killing it for me:

  • quick question?
  • voicemail
  • {{firstname}} / congrats
  • next steps?



Some words are more impactful than others in driving up your open rates. The general rule of thumb is that generic, cliche, salesy, over-used, or spammy words kill the open rate.

Also, words that give away your email as unimportant, irrelevant, non urgent, too complex, or fuzzy. Words like:

FREE, Exclusive, One time only, Deal, Only, Learn, Report, Webinar, Monthly, Don’t miss

On the other hand, words the outperform do exactly opposite by making it clear and obvious to the recipient that the email is about them, it’s about high stakes and it’s time sensitive.

So, use the words that invoke:


Calendar, time, call or meeting


Steps, campaign, renewal, next steps, account, you/your, {{name}}, {{company}}, congrats, thank you.

To add, according to 2015 research by Adestra, “breaking” outperformed the control group by 32%. So, go break some news. Manufacture news, if you have to.

Ah… and, “thank you” – again, according to Adestra – outperformed by whopping 62%… and with that, thank you for reading.

If it makes sense, share with your colleagues and your LinkedIn network.