Today's post is the final installment of our three-part series — LinkedIn Sales Prospecting for Introverts. If you missed the first post, Building Connections That Matter, or the second post, How To Leverage Content Marketing Strategies On LinkedIn To Attract Qualified Prospects, feel free to read those before continuing on to today's post, Introvert-Friendly LinkedIn Sales Techniques. It's ok, I'll wait 
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So far, we've talked about leveraging LinkedIn to find qualified sales prospects AND conducting social reconnaissance to uncover potential conversational catalysts, hidden buying signals, and personal and professional interests.
We've also covered every introvert's favorite sales prospecting strategy — generating inbound leads — by curating and creating interesting content (for your prospects) and sharing it on LinkedIn. The sharing of this content stimulates a response from your prospects, and presto, you're now involved in a conversation that you can eventually convert to a client.
Today, we'll tackle the networking tactics all introverts fear and some outright detest — cold and warm outreach.
Cold vs. Warm Outreach on LinkedIn
If you're a small organization, solopreneur, or maybe a freelancer, and you've deployed a well-designed, effective Painless Prospecting program, you may never have to conduct cold outreach on LinkedIn. I've been fortunate over the last 13 years to avoid it entirely.
BUT... the times are a changing. The amount of content created and shared today vs 10 years ago, combined with the sheer number of people attempting to engage in social selling efforts, is altering the landscape.
For the first time since founding Converse Digital in 2010, I've actually begun testing a handful of cold outreach efforts on LinkedIn. One is truly cold. I created a list of people associated with advertising and marketing trade groups. Then I messaged them inviting them to connect and/or book me to speak to their organization. I had zero previous contact with any of them.
In another effort, I launched my Painless Prospecting email this year. It's a weekly (well, that is my goal, but I'm not going to lose sleep if I miss a week) email missive for people who hate sales prospecting but, for whatever reason, are required to do it as part of their day job.
I have a wee over 2,000 connections on LinkedIn. But like anyone with that many connections, there are some that I've interacted with and far more that I've had little to zero interactions with since we connected. So while technically messaging those folks could be considered warm outreach, I'd argue the majority of the messaging was actually closer to cold outreach.
In both cases, I've been pleasantly surprised by the results. I'm seeing a 2% Reply Rate and a 3% Acceptance Rate for the speaking outreach campaign. That's pretty solid, I think. And the Painless Prospecting Campaign is producing a 6% Reply Rate, and almost 100 folks have signed up for Painless Prospecting. Again, considering that I'm only halfway through inviting all of those connections, great results, I'd argue.
As one would expect, warm outreach performs better, even warm outreach, which is a little cold due to lack of prior engagement. But the purely cold outreach is worth the effort too. Just make sure you've built out a great LinkedIn Profile, as we discussed in part one of LinkedIn Sales Prospecting for Introverts.
Crafting The Perfect LinkedIn Outreach Message
Spoiler Alert: there is NO perfect LinkedIn outreach message template. Unfortunately, based on the trove of LinkedIn cold outreach messages I receive every day, far too many salespeople believe one exists, and they all bought the same one from the same LinkedIn prospecting guru. 
I've started a folder called $hitty Outreach Messages, where I keep all the horrible LinkedIn and eMail messages I receive. It would be funny if it weren't so sad. So many people working so hard to sound exactly alike because they're too dumb or lazy to write their own outreach messages.
Instead, they follow the same basic template:
Ask any direct mail veteran what the #1 and #2 direct mail success drivers are, and you'll usually hear, in this order, the quality of the list followed by the quality of the offer.
The same thing holds true for LinkedIn outreach. Take the time to build homogenous lists. You're better off having 100 lists of 20 people per list than one list of 2,000 people. Yes, it takes a bit more work to build 100 lists. And yes, it will take a bit more work to create customized outreach messages that speak to the unique needs and desires of each 20-person list. BUT, because you've taken the time to create a great list and craft a compelling message, you'll produce far better results — especially if your goal is to start a conversation vs. making a sale.
Then get to the point. And the point is WIIFM. WIIFM stands for "What's In It For Me?" Scroll back up and reread the template everyone uses, and you'll notice one major mistake. It lacks a WIIFM statement.
When you reach out on LinkedIn — warm or cold — without a WIIFM statement, the subconscious message you send is: I think you're valuable to me in some way. But if you fail to show the person you're reaching out to how you can be valuable to them, you just sent a cold sales outreach message. One that most likely gets ignored, deleted, or reported as spam.
Look, time is everyone's most precious resource. And as you get older, start a family, take on more professional responsibilities, etc., the amount of disposable time you have available and the value you place on that time becomes inversely proportional.
So if you want anything from anyone, make sure they see the WIIFM in agreeing to whatever ask you've made.
That's what makes a great LinkedIn outreach message — no template required.
To Automate LinkedIn Outreach or Not To Automate, That is The Debate
I purposely left this point to the end of the post to force you to either read this far or at least scroll down this far but honestly, this debate, while it seems super important, is IMO the tail wagging the dog.
The "is social automation ok" debate is as old as social media itself. I vividly remember the early days of Twitter when products like Hootsuite, TweetDeck, Buffer, and others made it possible to pre-schedule your tweets.
The outrage. The horror. The gnashing of teeth. How dare you automate your Twitter engagement. It was dishonest. It wasn't transparent. It was inauthentic.
Until it wasn't.
Until cooler heads realized that Twitter, like all social media channels, produces asynchronous conversations. Yes, there are times when you just happen to be online when someone messages you, and you reply in kind. But far more often, there is a time lag between their message and your response. It's the nature of the beast.
Thus, your participation in Twitter, and any digital channel, doesn't require 24/7 participation. There is nothing inauthentic about posting a Tweet or any social media post when it's most convenient for you OR for your audience/followers. Reread the second half of that sentence again because that's the key automation point.
Let me explain with an example.
I'm a voracious reader. I love learning new things and sharing that learning with others who will benefit. But I do most of my reading early in the morning or late at night. Or I might block a few hours one day to blow through all the content I've queued up in my Feedly Reader inbox or saved to an Evernote or Roam page.
Now, if I chose to share all of the good stuff I found right then when I am reading it, I do the content, content creator, and my audience a HUGE disservice.
My audience doesn't have a few hours to read everything I just shared. If I shared the content on Twitter, chances are they would miss it entirely unless they were actively on Twitter at that moment. So all of my hard work creates no benefit to them or the content creator that published the work.
Enter social posting automation that allows me to drip all of this amazing content into my friends and followers' feeds when they're most likely to have time to read it or at least see it and save it for later.
When you view social automation through this lens, it doesn't seem so bad, does it? In fact, it's downright courteous... wouldn't you agree?
Similarly, when it comes to automated messaging, the difference between legitimate messaging and irrelevant spam comes down to one thing: the technician.
Spam isn't the product of the technology. It's the product of the technician using the technology.
Look at email marketing. Every day you receive automated emails. Most of which you either signed up to receive or someone or some company used technology to generate an email they believed you will find interesting or helpful. In either case, you're ok receiving these automated missives.
But, should you receive misguided, untargeted, irrelevant emails from people or brands you know or don't know, you're angered and likely tag it as spam. Especially if it's repeated every two or three days with a new missive attached that says something like, "Did you get my email?" or "Bubbling this up to the top of your inbox." Trust me... I've tested this approach myself just to make sure I wasn't allowing my personal opinion to color my recommendation. Every time I used that method, it failed.
But both groups of technologists are using the same technology to transmit their messages. One used the technology for good, while the other for evil.
The same logic holds true for social message automation, such as LinkedIn message automation. In the hands of a smart, honest technician, the software enables networking at scale.
But, in the hands of a transactionally motivated, selfish seller, it creates buckets of spam that do nothing but fill my ever-growing $hitty Outreach Examples file.
As I said earlier. You're better off creating 100 lists of 20 than a single list of 2,000. If you'll take the time to craft very homogenous lists of people that share common challenges and problems, you can write a single message that is equally relevant to every member of that list.
In fact, if you were actually to reach out manually, you'd likely just copy/paste the same message to each person, changing the {first name} on each message. Sure, you could take extra time and insert a single personalized factoid to prove the message they received was only typed and sent once. But why? If the content of the message you're sending is truly relevant to the recipient, does it really matter if you typed the message just to them vs automated the copy/paste/send function?
I'd argue no, especially for introverts. In fact, outside of using content to create conversations, it might just be the most introvert-friendly LinkedIn sales technique available today.
By automating the copy/paste and, most importantly, the send function of LinkedIn outreach, you automate the fear.
If you're an introvert, it's easy to write the message.
But the fear... the fear of not getting a response. The fear of being ignored. The fear of feeling stupid for thinking the person on the other end of the message would accept your connection request or act on your call to action.
Automate that fear away.
I'm sure I'll get some pushback from that point of view. And that's fine. Using technology to automate the transactional part of mass messaging is smart. Just don't automate the relationship part. Take the time to cull your messaging list to ensure the person who receiving the message "should" find it valuable.
Then write a simple LinkedIn message that gets right to the WIIFM point. Write it just like you'd write it if you were sending a single message. Use your voice. Write at the professional level you prefer. And always give them an easy out or permission to tell you never to send them a message again.
And if you want to automate the tracking of the campaign, maybe even use technology to help you know who didn't respond so you can reach out again at a later point — just in case they missed your prior message — that's ok too. Again, you're automating the process, the fear, not the person behind the process.
And finally, one word of warning. The one LinkedIn outreach message you should NEVER automate is the first one a prospect receives AFTER they connect with you or read/react to a message you've sent. Because now, you've automated the person behind the process.
Instead, choose an automation tool that will alert you when someone has responded to your message. This gives you a chance to jump into the process directly. Because, after all, the goal of the outreach isn't to create a transaction, it's to start a conversation that creates a foundation for a relationship that can create lots of transactions.
How To Create Awesome LinkedIn Conversations
Be yourself. There is something liberating about a keyboard and a computer screen. Even the most self-conscious and introverted of us can become funnier, smarter, more confident, more interesting, more vulnerable, and more helpful when engaged in text-based conversations.
I'm not suggesting you should never sell via LinkedIn messaging. But try and make those sales pitches the minority of your messaging. And when you do try and sell, make damn sure you're selling something valuable to people who really need it.
Do that, and your LinkedIn prospecting will always be painless.
And that's it. I hope you've enjoyed this LinkedIn Sales Prospecting for Introverts series. I'd love to hear your thoughts here or on Twitter or LinkedIn. And if there are other topics you'd love to have me dive deep into like I did here, I'm all ears.
Speaking of hearing your thoughts, if you're a first-time reader and liked this piece, why not consider subscribing so we can stay in touch? Of course, you can break up at any time if you don't like what we send 
. Till next time.
This post was originally published on Painless Prospecting, the weekly sales and marketing blog created by the fine folks at Converse Digital. If you want to learn how to create, engage in, and convert conversations into new clients and customers, give them a call.
