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Why you dread sending LinkedIn messages (even though you want to send them!)

If the thought of sending direct messages on LinkedIn makes you cringe, you're not alone—but what if it didn’t have to feel that way?


I talk with small business owners day in and day out, and I hear this frustration all the time. Sending direct messages is intimidating. You know your business would be better off if you sent direct messages; however, i'ts a struggle to get over the hump to create a consistent routine of sending them.


I get it! Reaching out directly feels hard, especially if you’re unsure about what to say or who to message. But here’s the thing: with the right strategy, direct messaging can be one of the most powerful tools for growing your business.


In this post, I’m going to break down the reasons why you might be avoiding direct messages and show you how to make them work for you.


"Direct messages are salesy"


Many small business owners avoid sending direct messages because they feel salesy or pushy. However, that's usually because they’re approaching them the wrong way. For example, they're cold pitching prospects. When you cold pitch prospects, you don't have any pre-built trust. No wonder you feel the messages are salesy. They are salesy!


I promise, there's a better way. When done right, direct messages are about starting a conversation and building relationships, not pushing a product or service. Instead of thinking about the sale, focus on how you can add value to the person you’re reaching out to. It's a completely different mindset, and it makes your conversations flow much more freely.


My Leads on LinkedIn program teaches you exactly how to make these connections feel authentic through my signature messaging framework and direct message templates. No more staring at a blank screen.


When you lead with curiosity and genuine interest, DMs build relationships and you stop dreading sending them.


"Why send direct messages when I can rely on inbound marketing?"


A lot of small business owners prefer to rely on inbound marketing, believing that leads will come to them if they just post enough content. I am a huge fan of inbound marketing. I use it for my own business by posting regularly on LinkedIn, writing emails to my email list, and writing blog posts like this one.


However, inbound marketing doesn’t give you full control over your client pipeline. While it does work especially when given time, it's more passive and leaves you waiting and hoping for the right people to show up.


Direct messages, on the other hand, give you the power to reach out and create opportunities today instead of waiting for them to happen.


With my Leads on LinkedIn program, you’ll learn how to leverage both inbound (content) and outbound (messaging) marketing so you’re in control of your lead flow without feeling like you’re waiting around for or chasing clients.


"I don't have anyone to message."


If you think you don’t have anyone to send messages to, it’s likely because you’re defining leads too narrowly. I suggest keeping a list not just of those are ready to buy now, but also of those who might be interested in your services down the line. In other words, folks that are worthy of follow up.


When you broaden your definition and develop a comprehensive and easy-to-update leads list, you’ll realize there are more potential clients in your network than you think. You'll also know exactly who to reach out to and when.


My Leads on LinkedIn program teaches you how to track leads and helps you identify those hidden leads in your existing network. I even provide an AirTable base so you can get off to the races tracking leads. And, through my plug-and-play message templates, you'll know exactly how to start and continue the conversation with your prospects.


You'll quickly see that there are plenty of people worth reaching out to — folks who would benefit from and enjoy working with you.


"Sending direct messages takes too much time."


Another reason many small business owners dread direct messages is because they think it takes too much time.


If you don’t have a system in place, direct messaging can feel like throwing spaghetti at the wall. You're always trying new messages and never know which ones work. Furthermore, you feel overwhelmed deciding who to message, what to say, and when to follow up.


However, with the right strategy, it’s actually quite manageable. In my Leads on LinkedIn program, we streamline the whole process with messaging templates, messaging critiques, and ongoing email access so you’re never left guessing.


Instead of spending hours crafting the perfect message, you can follow a simple, effective plan. Sending DMs won’t feel like a time drain—it’ll feel like an efficient, strategic part of your lead generation strategy.


(If you're sending messages and not getting as many replies as you'd like, don't miss this article about how to get more replies.)


Let's take the stress out of messaging


My Leads on LinkedIn program takes the stress out of direct messaging and make it feel approachable.


One of the key features is my direct message critiques. You’ll never have to wonder if what you’re saying is coming across the right way. With personalized feedback, you’ll learn how to fine-tune your messages so they feel natural and engaging. By getting this real-time input, you’ll feel more confident in your outreach, knowing that you’re making meaningful connections.


The actionable curriculum and plug-and-play templates are designed to simplify the entire process. You’ll learn step by step how to identify leads, craft effective messages, and manage your conversations efficiently. The templates mean you don’t have to reinvent the wheel with every DM you write. Instead, you can focus on customizing them based on the prospect's situation.


If you don’t like sending cold messages, the Leads on LinkedIn program will show you how to do it in a way that feels natural and effective. Instead of the uncomfortable, salesy outreach you might be picturing, this program teaches you how to connect with potential clients through genuine conversations. Direct messaging isn’t about hard selling—it’s about relationship-building.


I know that you don’t have hours to spend on LinkedIn. I’ll never suggest you post five times a week or spend your entire day online. Instead, you’ll focus on high-ROI activities that get results without overwhelming your schedule. You’ll learn specific, actionable strategies that streamline your lead generation process, so you can take control of your pipeline without cold messaging strangers.


Learn more and get started here.


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