Sales Prospecting Email Lessons from Lazy Susan, Boris Boring, Will Wordy, and Friends

December 21, 2017

Diagnosing Issues with Bad Prospecting Emails

Prospect outreach via email and LinkedIn InMail are popular and can be effective – when executed well. Unfortunately, your prospects’ inboxes are teeming with examples of emails that get ignored and deleted.

We’ve rounded up a few examples from our own experience, removing names to protect the violators – I mean, innocent – and dissected them to provide a clear idea of what not to do. We’ll also examine the key elements of well-crafted prospecting emails that get responses and drive better results.

Read on to make sure you’re moving forward with the best sales prospecting email templates and leaving bad practices behind.

Sales Prospecting Emails Destined for Deletion

The following emails fall flat for numerous reasons, as we’ll explore. A common thread among the three: failure to confirm the message was being sent to the right audience. It’s such an obvious stage in the prospecting process – and so easy to address with a quick check on LinkedIn – that it’s disheartening to see how many companies and reps continue to miss it, dashing their credibility.

Now let’s get into the nitty-gritty. This first prospecting email, clocking in at over 400 words, clearly tries to convey far too much.

Subject: Your Own Cybersecurity Service – better than ever

Dear [Name],

We've just released the next generation of our break-through Acronym-Laden cybersecurity tool, making it even easier for you to deliver a complete range of internal cybersecurity services to ALL your clients.

[The sender clearly didn’t do his homework since I do not provide security for my clients.]

To be among the first MSPs to check out all that's new, and get on board at a special limited-time price special, register for our upcoming webinar now.

[I’m not an MSP – very easy to determine by first viewing my LinkedIn profile or visiting my company’s website.]

Our Acronym-Laden security product includes a new pre-configured "Bronze" level offering, designed to be a base level "introductory" cybersecurity service with a low cost-of-delivery that allows you to deploy it even to your break-fix clients or those who just have you work on occasional projects.

[That’s a mouthful! You lost me after the 30th word in this 40-plus-word sentence. And what’s with the quotes?]

With the Bronze level plan, the internal threat detection alerts are first sent directly to your clients to self-triage, and then they decide which ones to forward to you for investigation and/or remediation. You bill for your time responding to their requests.

The client-MSP workflow is all built right into the alerts, and you manage all clients through a simple cloud-based portal. With this new service you'll generate a ton of incremental revenue, and use the activity to upgrade some clients to a higher level managed service.

[The past two paragraphs describe the value for me – that’s good… but it’s irrelevant to my business.]

In addition to the new Bronze level service -- which you can brand as your own -- our Acronym-Laden security product includes an enhanced cloud-based service management portal, a built-in "expert system" with recommended remediation strategies, and improved alert-processing workflow. 

[Since I don’t know about the previous version of this service, I don’t have the context to figure out the importance of the enhancements and improvements. Either way, this is an awful lot of detail to include in an email to someone you don’t know.]

Register for our next webinar, and be among the first MSPs who can offer, and deliver, this expanded set of indispensable services on an unlimited basis to all your clients for one affordable monthly fee. 

[How can I offer an expanded set of your services if I’m not offering any of your services?!]

Event Day: Monday, September 4, 2017

Event Time: 12 pm ET, 9 pm PT

Registration Link:

I hope to see you there!


Will Wordy

This second email, conversely, is short and sweet – to a fault:

Subject: Just missed you

Hi [Name],

I reached out recently but haven't heard back.

[Pretty sure this is the first you’ve reached out.]

Are you available for a quick 5-10min chat? Or feel free to schedule some time here.

[About what?]

Thanks in advance for your response.

Lazy Susan / Business Development Representative

Why would any prospect respond to such a vague email? Even if “Lazy Susan” did indeed leave me a voicemail or send a previous email, I shouldn’t be expected to remember the details. Don’t make prospects do any heavy lifting, but do give them a compelling reason to respond.

And the follow up email… More detail than the previous email, but still not enough context for me to understand the solution and how it applies to me.

Subject: Re: Just missed you

Hi [Name],

Since we haven't been able to connect, I wanted to send over two of our demo videos to give you a better understanding of both our desktop and mobile solution:

[Solutions for what? I have no idea what you’re offering or why I’d be interested.]

* You can view our web-based demo here

* You can view our mobile app demo video here

[I’m sure I can, but why should I?]

If you would like any assistance in your evaluation, feel free to reach out to me or drop a request to chat on my calendly. 

[Evaluation of what?]


Lazy Susan / Business Development Representative

Here’s the final example. Overall, it suffers from “it’s all about us” by overlooking “what’s in it for you?”:

Subject: Quick question

[Not an incredibly enticing subject line – and the email doesn’t exactly ask a “quick question.”]

Hi [NAME],

[A feeble attempt at personalization. The all-caps name was a tip-off that it was pulled straight from a database.]

(X Company) is based in (City). In 2016 we generated 108K+ sales ready opportunities, tens of millions in sales, without ever picking up the phone.

[Good for you! But why should I care…?]

We've run successful campaigns across more than 80 industry verticals. Our testimonials speak for themselves.

[The self-congratulatory lead-in generally isn’t going to play well.]

  • Increase in qualified leads.
  • Increase in unique website visitors.
  • Increase in lead-conversion rate.

We have developed some new lead generation tactics and strategy, and would love to implement them if we partnered with your organization.

[So I’m your guinea pig?]

I'd like to hear your opinion—May I give you more information?

[My opinion about what?]


Boris Boring | Business Development

And the follow-up:

Subject: Following up

Hello: [NAME],

Did you receive my last email?

[Yes, I did.]

Would you be willing to set up a fifteen minute call to discuss the opportunity?

[Nope. Still don’t know what opportunity you’re talking about or why I should care.]


Boris Boring | Business Development

The Elements of Successful Prospecting Emails

Good for you if you’re shaking your head and saying, “I would never send an email like that!” And if this isn’t the case, it’s not too late to change your ways. Call upon pre-defined email templates that follow best practices, and then follow these basic rules as you customize the templates for each prospect:

1. Check the prospect’s LinkedIn profile and company website for confirmation they are a fitting recipient, and for details you can use to personalize the message.

2. Align the email with the prospect’s stage of the buying process. For instance, don’t mention your solution if the prospect is just starting a search. Meanwhile, you shouldn’t waste time referencing general industry challenges to someone in the later stages of the purchase process.

3. As a follow-up to the previous point, use an appropriate call to action. Don’t ask for a meeting with the first message, or a referral when you’re still working on closing the deal. In fact, your focus should be on engaging the prospect in a conversation. Don’t force your pitch into these emails – it’s a dead giveaway that you’re truly only focused on making the sale.

4. Aim for brevity since you’re asking a busy professional to take the time to read your message. Stay on point by focusing on the value to the reader.

5. Whenever possible, use words that reference the recipient (e.g., “you,” “your”) versus you and your company (e.g., “we,” “my”).

Email prospecting is an essential activity and skill. Master it by studying what works and applying the best practices we’ve shared here, and you’ll soon see far better response to your outreach.

For further guidance on leveling up your sales outreach, download the Sales Prospecting Toolkit.