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How To: Consistently Book 5-10 Qualified Sales Meetings Per Week On LinkedIn

The Art of LinkedIn Outreach For Early Stage Companies

There are a few nuances to social selling that makes it very different than outreach over email or phone.

When it comes to outreach on any social platform something that you need to be mindful of is your online reputation.

When using email or calling you can be a lot more direct with your prospects, meaning that you can be upfront with your intention of booking a meeting with them. The reason you can be more upfront is mostly due to how conversations on the phone tend to be forgotten, and emails have a tendency to get lost in inboxes. This means that if you get ignored or if your prospect tells you he isn’t interested, you can always wait a few weeks and start again fresh.

With direct messages on LinkedIn however, you have a much higher chance of standing out in your prospect’s memory because there are (usually) fewer people competing for their time on this platform. Also every conversation is saved in their inbox, and therefore all your prospect has to do is scroll up to see the entire conversation history that exists between the two of you.

This means that if you use the same approach on LinkedIn as you do with email or phone then all you’re going to accomplish is burning your leads, ruining your online reputation, and getting your LinkedIn account penalized.

So with this in mind I usually try to take a softer approach; but once you have mastered the nuances of social selling it can become a great way to reach out to your prospects as it has higher engagement and quality of conversations:

  1. Engagement: Since there is less competition for your prospect’s time on LinkedIn you have the opportunity to stand out more to your prospect than on any other medium. Standing out means that your message has a much higher chance of being read and understood by your prospect. Statistics pulled from my client base show that engagement rates on LinkedIn are more than double that of email (38% reply rate vs. 16% reply rate retrospectively).

  2. Quality: Cold calling and email doesn’t always create quality meetings. When you cold call prospects sometimes they feel pressured to take a meeting with you, and aren’t in the conversation for the right reasons. With email, you never know what you’re going to get because there’s usually minimal conversation before-hand to provide context. From tracking data pulled from my clients, deals sourced from LinkedIn are twice as likely to close than deals sourced from email and three times more likely than deals sourced from a cold call.

Step 1: Put Some Work Into Your LinkedIn Profile

Before doing anything on LinkedIn take some time in making sure your profile is presentable.

The most important part of refreshing your profile is to make sure that you have a professional profile photo. Having an impressive LinkedIn photo is important because it’s going to be the first thing your prospects are going to see when you send them over a connection request (which you have to send before messaging them). Go to a professional photographer if you have to, it’s worth it trust me.

The second thing your prospect is going to see when reviewing your connection request is your “Headline”. This is the first line in your profile under your photo and your name. Try to capture exactly what you or your business does in one to two sentences. A good headline is great for piquing your prospects’ curiosity, getting them to click into your profile and accept your connection request.

You can follow this format: We help (target market) by (solution)

Next thing to consider is your banner photo. You don’t have to do anything too fancy for this, just find a stock photo of a beautiful landscape. I would avoid having your logo or any other sales material in your banner photo as this can make you come across as salesy. You don’t want your prospects to get their defenses up. Feel free to visit to find stock photography that you can use.

Keeping with the theme of not being too salesy I like to keep my about section casual. I think it’s a great opportunity to talk about any hobbies you might have, allowing you to connect with people who share similar interests.

Investing in my LinkedIn has resulted in a significant amount of passive lead generation for my business. On average I’m booking as many as 5 passive meetings (prospects approaching me) per month. These meetings resulted in my first two clients for my consulting business.

Step 2: Sending Your Connection Request

Step 2 is pretty simple, as I’m sure most of you know how to connect with people on LinkedIn.

When you’re selling just make sure that you’re connecting to RELEVANT prospects. Don’t just bulk connect with everyone you sell to that may or may not be quality decision makers in your niche. You can help yourself do this at scale by investing in SalesNavigator, allowing you to filter out prospects that don’t fit your buying criteria.

Also make sure to send a message with your connection request. This can increase your acceptance rate by over 20% (from 18% to 44% for my business). It doesn’t have to be anything too fancy, just keep it friendly.

Step 3: Initial LinkedIn Outreach

The key to keeping a conversational tone in LinkedIn is not pitching the meeting straight away. Instead dig for a pain first, before you talk about having a conversation. A great strategy for digging for a need is to end your message with an open ended question, such as:

  • “How has client acquisition been going for you so far?”

  • “Have you run into any roadblocks in hiring your dev team?”

  • “What are you currently using to store customer information?”

Using these questions will open up a dialogue with your prospect. For important prospects I like to include a few personalized sentences pulled from their profile to increase my response rate. The goal of the first few messages is to dig for a specific pain that you can use as a reason to have a conversation with them.

Do not pitch a meeting until they’ve admitted to a pain that you can actually solve for.

Step 4: Follow Up

Here’s what a good LinkedIn cadence will look like:

  • Day 1 – Connection Request: Send your prospect a connection request, make sure you attach a message to your request to increase connection rate (40-50% average acceptance rate).

  • Day 1-2 – Initial Message: try to open up a conversation with your prospect, end your message with an open ended question. (28% average reply rate)

  • Day 5 – Follow Up Message: short follow up message that brings the conversation back to the top of your prospects inbox. This only really needs to be one sentence maximum (15% average reply rate).

  • Day 10 – Break Up Message: I like to use humor as a last ditch attempt to re-engage my prospect. Feel free to use memes, jokes, or anything else that’s funny that you can think of (5% average reply rate).

I wouldn’t send more than 30 connection requests and over 50 messages per day. The reason for this is that you can start to get throttled by LinkedIn if you start to exhibit certain behaviours.

For example if more than 5 of your connection requests are rejected in a given day, your account can start to get penalized and flagged for spam. That’s why it’s important to limit your connection requests you’re sending out.

You’ll begin to notice your account getting throttled if your engagement begins to dip (profile views, connection acceptance rate, reply rate etc.).

Don’t worry too much about this however, if you wait a week (in extreme cases a month) your account will be restored.


So how much daily activity is needed to book 2 meetings per day?

  • Send 20-30 connection requests daily

  • Send 30-50 direct messages daily

There are LinkedIn automation tools that can help you automate this process (Octopus CRM, Unlinc).

In the beginning it can be wise to decrease your activity levels and focus more on personalization. It’s possible to book a similar amount of meetings per day doing that it’ll just be more time and labour intensive.

Personally I choose to automate this process, but keep in mind that I have extensive experience targeting my specific niche. It might make sense to lower activity levels and focus more on personalization in the first few weeks to nail down your targeting + messaging, before investing heavily in automation.

There’s still so much to be covered about this topic, so in the meantime if you have any questions feel free to ping me or post them in the comments below.

I love connecting with entrepreneurs so feel free to send me over a friend request as well!


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