Best sales email templates and worst mistakes in outreaching top sales executives

Don’t fake your way to personalization. This LinkedIn message smacks of the bare minimum effort.

1. The ‘Inc.’ after my company name tells me it was grabbed from my profile.
2. Even worse is that she mentions she only works with Management Consulting companies. That is the category I’m under on LinkedIn because nothing fits better, but it is not what I do.

Let’s break it down…

1. OK, you’ve offered proof that you actually did go to my site and there is a valid reason for your outreach.
2. Complimented my decision, and legitimately pointed out why it might be time to consider something else.
3. Established credibility without making the email too much about them.
4. These questions offer value [what should I be asking myself]; at the same time, it builds curiosity for their solution.
5. Good call-to-action, and doesn’t put the onus on me to click on their calendar.

The best approaches I have seen lately use a CTA on the outreach not for a demo or even a discovery call but instead a next step that is branded for maximum value for the buyer. Often these CTAs are opportunities for the buyer to understand how their capabilities are comparing to their peers, such as a benchmarking exercise or assessment.

In the early days of HubSpot we branded this first discussion an inbound marketing assessment where the buyer would share their demand generation goals, design, and performance and we would benchmark them against their peers with counsel on what has worked to improve them.

There was no discussion about the product. It wasn’t labeled as a discovery call for the buyer, even though from a sales process perspective that is exactly what we were doing.
This CTA approach is often more aligned with where the buyer is in their journey, attempting to frame the opportunity correctly first before learning about solutions. The approach also tees up the seller nicely for the next conversation, as it is clear to the buyer the value they will receive in exchange for honest answers they provide about their current performance and strategies.

Give it a shot. Come up with a name for the discovery call that will be appealing to the buyer and make it the cornerstone of your CTA in the initial outreach.

“Flirt with me before you ask me on a date.”

Now, here’s a way a seller who does not understand that my priority is the buying journey, and not the selling process. Telling me why I should connect with you is pretty presumptive on the first communication, and passive aggressiveness does not a nurturing or follow-up strategy make. Here’s where they went wrong:

1. They asked me a closed-ended question about a fact I did not know—that I was a Certified Partner of ABC Services. This sales rep did not do their homework to understand that I lead social media marketing and not email-based demand generation
2. Poorly written emails with lousy grammar and punctation immediately is a big strike against being able to start a relevant conversation
3. Targeting targets, hmmm
4. No one likes passive aggressive follow-ups

“Good relationships always start by putting the other one first.”

Consultative, authentic, and creative approaches will make an attention-getting first impression. It’s vital that every salesperson comes across as a potential partner and not a virtual cashier. They need to establish credibility by showing me in the first touch that they ‘get’ my ecosystem and my place in the ecosystem—I can tell that they offer a solution given their email address. This salesperson understands how to use content to start the conversation.

1. Do your research and personalize your communication.
2. Make me feel a little comfortable with a statement to show I still have room to learn.
3. Tell a story with a metaphor or analogy, so it’s easier for me to get
4. Show what others have done vs. what you can do to help me get the greater context
5. A relevant fact teaches me something and goes a long way
6. Adding an approachable call to action is a great way to trigger a response from me

In general, I think it is unfair to focus on the last link in the chain, the poor SDR hung out by their company. Who provided the list, on what basis? What was he trained to do, fight to the end or work with the right prospects to get a mutually beneficial outcome? The rep did what he was paid to do, he could have brought some flare and style. But technically he executed their playbook. Next time they should train from the top down.

Personalization, the way it is done (butchered) today is just BS. He got real personal in ways that count for me, money and my content. None of the usual silliness implying that I am missing something, or that my efforts are falling short somehow. He did it in a way that stroked my ego, and suggested that I can take things “even further.” We’re still talking.

Here are ‘John’s top 5 mistakes and my top 5 pieces of advice on how he can improve his engagement.

1. Not knowing what my current solution is. How can you describe how you are different (not better) if you don’t know what I’m already using? Ask what I’m currently using so you can reply with a unique, compelling, and relevant value proposition that tells me what I get out of using your product or service.
2. Not knowing how satisfied I am with my current solution. If I’m satisfied with my current solution I’m not likely to switch. Ask how happy I am with my current solution so you know if I’m even likely to try you or switch to you in the near future.
3. Telling me, a 57 year old who is a much better talker than a typer that you have no phones. If your sales team has no phones I’m assuming you’re so small you can’t afford them and if you’re that small your support team probably also has no phone and can’t service me once I become a customer.
4. Telling me cold calling is dead. I’m 15th on LinkedIn’s list of the world’s top B2B Sales Experts. I teach how outbound, or cold calling as he says, is the best way to sell six and seven-figure solutions to recently motivated decision-makers (read: VPs or higher that are new in their job) who are more likely to switch vendors. Don’t alienate the reader. Know enough about someone to have something in common and use that as a bridge to start a conversation.
5. Not including a phone number. Making someone, who might be mildly intrigued that has two minutes to themselves now to call and learn more, to reply via email is a big opportunity killer. People will say to themselves I’ll get to this later and later almost always turns into… you guessed it: ‘never’. ALWAYS, ALWAYS, ALWAYS include a phone number.

The good news for ‘John’ is that his email was so bad that I actually filled in his form to get him on a call and share the above advice in person.

The even better news for ‘John’ is that after him taking my advice I actually become a user of his solution.

1. Didn’t know my name.
2. Has no idea who I am or what I’m doing, just fishing for somebody.
3. Dangling participle at end of sentence.
4. Weird grammar and misspelled words.
5. Final ask adds no value to me, there’s no offer or reason to spend time on this.

This is among the worst but I get a lot of them.

1. I don’t do Network Marketing, so not sure why his person or software chose me to connect.
2. He’s trying to pique my interest and have me wonder and all I’m wondering is why he didn’t say what it was and why he is trying to connect with me.
3. Again, he is assuming I’m in his industry. I clicked ignore on his request. My suggestion is to do your homework before you send a message. Quality is much more important than quantity. If he had skimmed my profile or looked at my posts, he would have known that I am not a prospect.

The worst approach in business is making assumptions. Guessing about the situation of others rarely plays out well, if ever. This short message provides an abundance of assumptions and sales errors.

Before contacting someone, read their profile, research their website, and consider how you may connect the dots between the two of you. I never brag about achievements, but they are on my varying profiles and website for all to see. The communication would have been quite different had he taken a moment to glance over even one page.

It is a cardinal rule always to address a prospect by name to gain their attention.

Upon reviewing his profile, it is evident that he recently graduated from college to enter the field of sales. I assume that the pressure must be severe for him to make quota, and he does not know how to handle the situation. Revisiting upfront research, he would see that I have held a long-time career in sales and entrepreneurship.

For me, the worst statement is in reading that he can improve my personal life too. He doesn’t know anything about me personally or professionally. The declaration is outrageous. I did my best to mentor him on improving his approach politely. The messaging came to a halt. On my end, I deleted all of it.

One of my sayings is “Trust Is The Soul Of Sales.” Make your clientele the top priority. By asking about their experiences and opinions first, you begin to build the relationship, trust, and very likely the sale. Strive to earn a returning and referring clientele or the Smooth Sale!

Name,
I’d love to teach you better ways to use LinkedIn to grow your business. If you are open, here is a link to my calendar http://scheduleacallwithbrynne.com please pick a time that works best for us to talk.
Brynne

1. (yes, he or she didn’t even finish the message! I decided to have some fun with my reply that I sent without accepting the invite)

Name,
Thanks so much for connecting with me on LinkedIn. I am so glad you took away some value from my interview with Jen, she is amazing.
I thought I’d share some additional insights that you might find beneficial as well. https://ptdrv.linkedin.com/fxs6f75.

If you have any LinkedIn or social selling questions, let me know, I am always happy to jump on a zoom call, reach out anytime.

Brynne

1. In this example, the sales rep simply wrote: “Best Regards”. Clearly, this was a really bad attempt at a cut and paste or using automation on LinkedIn which is strictly prohibited by LinkedIn terms and conditions. We don’t have to dwell too deeply on this one. This is not what we call personalization. Period. This is just as bad as sending a message with no personal message.
2. In this example, the sales rep sent this personalized message at the exact same time that his peer and his Vice president did. They were all literally one on top of the other as found under the “My Network” tab on LinkedIn. So what was clear from this was they were using either automation or a really bad script. Further, all three didn’t even address me by name. Their message was all about what they wanted. They were looking to connect… and expand their network. Buyers look at this and ask, “what value are you bringing to me” and “why should I connected with you”. Neither were answered in their personalized invitation. In this case, as a buyer, if I had no interest in connecting to expand my network, connect with like-minded entrepreneurs or highly motivated sales pro’s I would simply hit the “X” or “Ignore” button, which is exactly what I did
3. In this example, there are several things that went wrong with the message. Let’s start with the obvious:
   1. There was no social greeting like “Hi” Mario or what we recommend to use “Hey” Mario
   2. There was no personalization at all. #ShowMeThatYouKnowMe
   3. Vengreso is not a “b2b brand or agency partner”, in fact, we have nothing to do with being a branding or agency marketing organization. So clearly you didn’t know who we are.
   4. I was clearly confident that we didn’t have any synergies
   5. You asked to set up a quick intro call but you failed to include the WIFM (What’s In It for Me) message. Why should I spend any time with you? Also, on cold connection messages, you NEVER ask for the meeting. You need to work your way to a conversation ONCE you’ve established a connection. Your goal here during the connection phase is to get the buyer to hit accept on that connection request. It’s what you do after they connect that will govern if you can secure a meeting.

These two messages come in as one of the top “best” LinkedIn connection request messages. Simply put the sellers showed me that they knew me by demonstrating they researched me, the buyer. Here are three ways they did so:
1. They greeted me with a Hi/Hey and my personal name.
2. They identified where they saw or read about me. This is an excellent way to connect. Always reference where you saw your buyer speak at, like at a conference, or leverage an article they were featured in (like in the second example). If neither of those items exist, you could always reference something the buyer posted on social media and include the actual link to their post/tweet.
3. Edify the person you are connecting with using words like “I learned from you”, “it would be an honor to connect” or “I don’t want to miss any of it”. Who wouldn’t want to connect with someone that makes them feel like they made an impact?
Overall these two messages were clearly hyper-personalized and the seller’s goal was to get me to press the “accept” or “checkmark” button and that they did. Their next goal now is to provide value using content that maps to creating brand awareness or help address a problem that the buyer has. This would be sent by the sales rep through a LinkedIn Welcome Message after I “accept” their invitation to connect.

From here I discussed 2 areas:

1. Stop spewing stuff about YOU and what YOUR company does… I don’t use staffing firms or recruiters so I could care less… but if I did it would still be a big turn off.
2. Do your homework, i.e. even a small amount of pre-call research to know who I am, who I work for, and what I do.

By all means, seek permission to continue.
Although there are differing opinions on this, find a point earlier in the call and sense if your prospect is distracted or busy and ask if it is an ok time to chat. After the call I had totally forgotten my other phone was still live… needless to say she heard my entire “coaching session” with the prospector!

From here it was all back and forth and he convinced me to have a 2nd call with his company’s President to learn more about their outstanding prospecting training…. after a 3rd call I hired them to do some training.
The KEY takeaway here: On cold calls bring up something about THEM or THE PERSON in the first 10 seconds. It’s called extreme personalization and it works! I like to say, use the word “you” or “your”. Noticed how he said “was this YOUR biggest event…”?

Nothing about this outreach is personalized to me or my business. I’m clearly on a list of hundreds of other executives of small companies. I like that he leads with thought leadership but we are self-funded so his opening statement doesn’t resonate with me. Then comes the pitch. If you haven’t got my interest from the start, why would I take any time to read your pitch. Then he throws their ‘diverse set of options’ at the wall in the hope that something sticks. His call to action is weak. Why would I reply? I did not.

Rather than share a good example, I think it would be useful for people to see what I would have written if I was him. I am active on LinkedIn. He could have mentioned something from my LinkedIn profile or an article that I had shared recently. This would have demonstrated to me that he’d taken the time to do his due diligence on both me and Empire Selling. The title of his InMail could have been “Mental health, rugby & congratulations”. That would have got my attention. And then perhaps the below. I would absolutely have accepted his connection request and been open to a conversation at the right time for us in the future. What was interesting is that the salesperson had some connections in common with me on LinkedIn. If he had been referred to me through one of my trusted connections, I would absolutely have taken a call from him.

This is so shallow and manipulative.

1. Shallow: I found your email on LinkedIn. That’s it? Just my email? Nothing else apparently mattered.
2. Manipulative: Do I keep all my options open OR do I have enough money for the rest of my life? Yes and No are the only rational answers. You can smell the ‘spam’ on this one.

Lastly, he used a gmail account (e.g., [email protected])

What prompted me to call? Several things:

1. Headline of my own course in the title; that caught my attention.
2. He mentioned my course on Udemy which means he is aware and knows my content (i.e., not a generic ‘we like your course’ email).
3. Technology platform that serves 100+ Million. That’s a great market reach. Even if that is only half true, that’s a lot of eye-balls).
4. He talked about a strong demand for my content and I agree with him (i.e., like mindedness).
5. ONE course could generate $300-$3,000. I like that he put a number (range) which indicates he knows his numbers. Why? Well, notice the range wasn’t from $0 to $3,000 or up to $3,000. Also, I have 45 courses…the math looks good.

Bottomline, this email had three hooks: He communicated that he knew me (my product), he demonstrated credibility, or at a minimum intrigue, with the 100+ million person reach, and he focused on what is in it for me (revenue potential).

What is the value prop of me spending my time to hear what you do? What value is derived from this type of outreach? I don’t even know what this guy does.

Paying me to take a demo? This smells of desperation, like the only value you can give me is through paying me for my time. This is a horrible approach and will keep your sales team on the phone with unqualified prospects.

What you should be doing instead. If you’re looking to book a meeting with someone on LinkedIn. Make sure you first start to understand what “value” means to them and how you can trade “value” for time. Most people look at money as currency but they completely miss the fact that time is worth more than money. What type of content have your prospects produced? How can you take that content and use it as currency to get visible, valuable, and connected in order to earn your way into an ask.

Your first step on LinkedIn should be to get connected and then create “value” driven conversation around something you have in common. Example: Share a video excerpt on LinkedIn and then tag the person that you are trying to get connected to. Once you are connected send a DM and reference the content to start the conversation.

If there is no common connection around commonality or context, it’s not a good time to make the ask on LinkedIn. You can’t be lazy. You have to work for it. Treat other people’s time like gold.