“Sales emails to send when your client has been ‘on vacation’ for 4 months”
“Sales emails to send to prevent being fired”
“Meditation exercises for salespeople who cannot write an email that gets a reply”
“Convincing excuses to feed a sales manager”
If you’re in sales, you’ve probably Googled at least one of these phrases before.
Even after diligent phone calls and follow ups, carefully-written emails and a perfect demo, prospects can go MIA. They lose interest, buy from a competitor or simply wander off into the woods and start a new life as a reclusive outdoorsman.
And, if you’re like me, there’s nothing worse than a prospect who goes MIA.
Even a “no” is preferable to silence. At least it’s feedback. Early in my sales career, it seemed as if many prospects I spoke to found themselves wandering into the Vermont wilderness, never to be heard from again.
Fortunately, I eventually did learn how to write sales emails that get responses and continue to do so for a number of clients including tech startups, staffing agencies, design boutiques and for my own client growth.
Some of the strategies I’ve found to work are obvious. Many aren’t.
But if the quarter or month feels like it’s constricting around you like a python and you need to start getting answers and moving prospective clients down the funnel, you can bet you’ll start getting responses from at least one of these tried and true email strategies.
It’s Not About You
There are a few dozen sales email templates that circulate most sales departments. If we step back and look at them objectively, they’re usually almost entirely about us, the salesperson, and what we want from a client.
We want their time. We want their attention. We want their money. We want their signature.
And, if we’re capable salespeople, we should ask ourselves in each email we write: what’s in it for my customer? What do they get out of this?
Even an email in which all you need to do is get their signature to start their service, which on the surface benefits us most, we can spin it to be about them. Instead of asking for their signature, we have to explain why it matters to them. Perhaps, if we get their signature today, you can prioritize their onboarding or lock in the special offer that ends this week. What’s in it for them?
Get a Response
Let’s assume you sell a SaaS product for a startup. You had a demo, the client seemed interested, expressed their desire to hear more, has a quote— and then your prospect went MIA and disappeared.
They’re not opening your old emails. Their voicemail is full. The month is ending soon. You think you’ve tried everything short of coming to their home with a pen and contract.
So, how do you get a response? Try (at least) one of these 10 sales email strategies.
Add Serious value
When I worked for a SaaS company that served small retail businesses, I’d make sure my prospects knew I understood their industry. One way to prove credibility and catch them off guard with a follow up that none of your competitors use?
If I hadn’t heard from a prospect in some time, I would check their company social media accounts and let them know about a tool I’d learned about could help them attract more followers. I’d direct them to an article about new trends for stores just like theirs.
Of course I’d include a subtle call to action in the email, but 97% of the content would be beneficial to them. If what you sell can be hard to distinguish from its competitors or you’re selling in a crowded space, being the most helpful and valuable salesperson your prospects work with can be one of your greatest strengths and this email creates that perception.
Make an Intro
Using a similar mentality to the value add email, making an introduction to your prospect can create serious goodwill.
If I’d spoken with a client who mentioned customer loyalty was important to them, I’d introduce them to a partner who could provide an integrated loyalty program. If they needed branding, I introduced them to a graphic designer. If they wanted marketing help, I introduced them to an agency.
Tread lightly with this one. Your prospect may not want to be introduced to anyone and, if you get the sense they’re quite private, this email can simply be used to ask if they’d like an introduction. I usually took the initiative and made the introduction proactively, but use your discretion.
Whichever method you choose, it shows you’re serious about their success and want them to do well. You’ve gone from just another salesperson to someone they can rely on, a trusted partner.
Even if you’ve asked about next steps at the end of each call, prospects and salespeople can lose touch with what needs to happen next. Maybe the prospect changed their mind or something unforeseen happened on their end.
I found it worthwhile to ask them: what would be helpful to you? It might read like this:
We loved having you on the demo last Wednesday! It sounds like we’re a great fit for (Company Name)’s desire to (something they want to do) and I understood that we were to connect this week to figure out what happens next.
I’m curious: what would be helpful to you at the moment?
If you’d like to schedule another demo, speak with a partner or get on a phone call, please let me know how I can be most helpful to you.
This email lets you ask about next steps in a way that a prospect perceives as helpful and customer-centric, not intrusive.
Multiple Choice Answer
If a prospect has been silent for quite some time, this style of email allows you to interject humor into the conversation while figuring out next steps.
With bullet points listing a specific possibility, tailor it to your last conversation and ask them to choose which situation best fits their current position. It may look something like:
Last we spoke, you mentioned you still had construction at the store and it may delay your decision. Which of the following best fits where you’re at now?
- I’m ready to go, just give me a call!
- This is delayed a few weeks, but I’m definitely interested.
- I need something else from you like a demo, additional quote or a phone call.
- I’ve chosen to go a different route and am no longer interested.
- The construction project’s excavation opened up an Indian Jones-style archaeological site and we’re just waiting on Harrison Ford to get here— but I’m still interested!
Tailor the humor to the person you’re speaking with. Write something you suspect they’ll resonate with.
I was amazed to learn how big of a barrier not understanding the steps of the buying process could be to buyers, especially outside of enterprise sales.
Sometimes all it took to close a sale was to break down what happens next.
If you think your customer may be unclear as to what happens next, send them an email that outlines in 3 brief, short steps what needs to happen to become a customer. It could look like this:
- After a quick demo, we find which package works best for you and decide upon an annual or monthly plan, based on your budget.
- With a signed agreement, we’ll take payment which can be offered on 60 day terms.
- You’ll work directly with our customer success team and experience unlimited training and 24/7 support whenever you need it!
Make sure the steps are simple and concise. Be specific if you can directly address a concern or detail related to this customer.
Social Proof Email
Do you eat at a restaurant on Yelp with 2 stars? Do you cancel your Uber trip when the driver is shown to have 1 star?
Social proof matters and we do make decisions based on others’ opinions and feedback.
This strategy walks the line between self-interest and self-promotion and being helpful to your client. It’s what I call the social proof email and it may read something like:
I just spoke with Jim who joined us in May as a client. He said the integration with WordPress has been perfect and he’s even been able to do (two things the customer was interested in).
This was a major concern of yours and I’m glad to hear it can be resolved easily. When could we set up a brief phone call about getting started with (Company)?
Bonus points if you have a client who loves you so much they’re willing to speak directly to your prospects as a brand advocate, an introduction you can make in a separate email.
Most likely your prospect is busy and reading emails on mobile.
You don’t have much time to get their attention.
Experiment with short emails and show them you value their time:
You mentioned a loyalty integration is vital for (Business Name).
Here’s our fantastic partner who can do exactly what you’re looking for.
Knowing they’re a trusted option, does this allow us to work together?
I’m a believer that GIFs shouldn’t be relegated to Twitter. Whether you call them “GIFs” or “JIFs”, visit giphy.com and see what you can find that will help spark a new conversation.
I had a client who’d gone MIA for weeks. She mentioned their printer, which was central to their business, was no longer working. I sent her the following:
Last we spoke, your printer was keeping you from continuing a conversation about (product).
Did you get it solved, or have you taken a more creative approach?
(For anyone who didn’t click the link, it’s a GIF from the movie Office Space where they destroy their long-hated printer with baseball bats and serious enthusiasm.)
I had a response within minutes.
The Compassionate Salesperson
Salespeople aren’t always thought of as human-beings. Our prospects usually know what we want. They’ve heard the jokes and seen the movies about sales people.
So, what happens when you break that stereotype?
If you’re in sales, you probably/hopefully have a great deal of empathy. I often connected with my clients and genuinely cared about their success, so when they went MIA it was a bit like being ghosted by a friend.
Borrowed from a previous sales team, this email worked wonders in finding out where they went:
Subject Line: Are you ok?
We’ve had some great conversations and, last I knew, you were interested in getting started with (Product).
However, I haven’t heard from you in a while and that’s unlike our previous communication.
Is everything ok?
This suggestion might sound incredibly manipulative. In some sense it is. But it’s also valid in that I had several clients or their business partners respond to tell me they were, in fact, sick and in the hospital or had suffered some major setback.
One prospect even died, however, I’m confident our service wouldn’t have prevented it.
This not only lets you put some empathy and concern for others out into the world, but it also helps you understand what’s happening in the personal lives of your prospects.
We’re Breaking Up
If you’ve tried many phone calls over the course of many months, sent creative emails, schemed with your sales manager on a way to get their attention and there’s still no response, it’s time for a new plan: the breakup.
Breaking up can be hard to do with a prospect, especially if you’ve spent a great deal of time with them on calls or demos. However, at this point, they know you’re available and ready to take their call, the catch 22 of being skilled at follow up. They have the upper hand and know you’ll come running back when they want you.
Create scarcity and see what happens.
By sending emails that announce you’re going to stop reaching out, you create a sense that you’re going away. They need to do something to prevent it— and the best way to prevent your sudden scarcity? A response.
It’s helpful to send at least one breakup email. In each one, I ask a variety of questions: what would be helpful, what have they chosen to do, when might be a better time to discuss their needs? You can also drop in helpful links to add value, like a webinar or article they’d find useful, plus a link to Calendly so they can set up an appointment in 2 days or 2 years.
Another strategy? Ask for feedback on your sales style in the final, final email. I’ve sent an email similar to:
Subject: Was it me?
I’ve enjoyed exploring (Product) with you, however, I haven’t been able reach you.
Perhaps you’ve chosen to go another direction, but I’m always looking for feedback from those I enjoy speaking with: what could I have improved or done differently that might have let us work together?
Hope you’re well!
I’ve received helpful feedback. I’ve been told I was too aggressive. I’ve been told I was the better salesperson among my competitors, but it came down to features we didn’t have.
The breakup emails can be the final push that gets them back in touch, thanks to scarcity.
If You Want to Sell, Don’t Do This
There’s plenty of great sales and writing advice out there. There’s just as much, if not more, terrible sales and writing advice out there.
These strategies live firmly in a category I call: “Please, just don’t.” I see some of these ideas suggested in “how-to write a sales email” articles and can only hope salespeople aren’t using them.
- “My manager asked me to follow up.” It’s one part used-car-negotiation-tactic corny and one part I-must-be-working-with-the-worst-rep-in-the-company concerning.
- “My manager asked me to close your file.” Does your prospect care about your Salesforce pipeline? Nope.
- “Hello Sir/Madam…” It takes seconds to personalize an email to your prospect who you’re asking to spend hundreds or thousands of dollars and potentially hours of their time to implement your solution. Look at your notes, find out who they are, what your last conversation included and what their unique motivations are.
- “Dear Sir, We request that…” Victorian English sounds great when you’re reading Charles Dickens, but overly formal language loses everyone. I have yet to meet a CEO or senior decision maker who speaks like Frasier Crane. I use my Midwest, casual tone like I’m speaking to a neighbor or friend.
- Writing War and Peace This isn’t the place to write 1,700 words. It’s a place to write few words and communicate your ideas succinctly. If you need to explain something complex, try hyperlinking the text to a video, article or infographic that can more completely communicate your thoughts— or communicate via phone.
- Not using “because” The word “because” will become your best friend because research has shown it leads people to comply with what you’re asking— even if it’s a terrible reason. “Hey, can I borrow your car?” is, according to research, weaker than “Hey, can I borrow your car because I’m competing in a demolition derby on Tuesday.”I’d recommend making whatever follows “because” as compelling as possible, however.
A Few Final Thoughts on Sales Emails
Even with inbound marketing becoming more and more common in companies, being an effective email and outbound sales-style writer will help prevent your prospects from going MIA and killing your quota and quarter.
But it’s not always easy to figure out what works. For some industries and clients, these email strategies will be a slam dunk. For others, there will be crickets until they’re polished to speak to the prospects’ interests and style.
That’s why it’s important to craft tailored sales copy, targeted for your clients, unique selling points and tone.
If you’re looking for sales emails and messaging that speaks powerfully to your prospects, that’s where I come in. I work consultatively and collaboratively with my clients, using what I learned from my sales career in staffing and tech sales, plus continued feedback from my current clients.
Photo by Tim Gouw from Pexels