Particularly when freelancing (and the entire economy) still feels a little rocky at best, I’ve seen a lot of growing interest in exactly how I approach business development.

After I sent my recent newsletter about setting aside a day each month to check in with old, new, and existing clients, I received quite a few questions like this: 

• “Can you talk a little more about how you reach out to potential clients?”
   
• “What do you say to strike up a relationship with prospective clients?”
   
• “How do you manage to get a response from people you don’t even know? It seems impossible.”

I’m more than happy to share my typical approach. Maybe I’ll dig into it in even greater detail in a future newsletter or blog post (*runs to add it to my ideas spreadsheet*). But in general, it looks like this: 

1. I use LinkedIn to find the relevant point of contact (usually a content manager or editor) that works at a company I’d love to bring on as a client. 

2. I send a connection request on LinkedIn with a personalized message. You have limited characters (only 300 of ’em) to get your point across, so I usually try to keep it simple with something like this: 

Hey [Name],

I hope you’re doing well!

As a freelance writer focused on the world of work, I love the content you publish on [Client]’s blog. Your recent post cautioning candidates against “rage applying” was great—I have it bookmarked.

I’d love to connect here if you’re open to it!

Kat 

3. While I’m at it, I also see if they’re active on X (when will I get used to calling it that?) and follow them there too.

4. I keep an eye on their content on both LinkedIn and X to see if there’s anything I want to periodically engage with. I don’t go overboard—just a comment here and there to build some familiarity and name recognition.

5. If I feel like I’m getting a positive response to those interactions and we’re starting to build more of a surface-level connection, I reach out with more of a hard sell or pitch—or just to schedule a virtual coffee chat. A lot of this depends on gut feel. 

Sometimes I don’t play the long game and will use my LinkedIn introduction message to jump to my pitch right away. When I go that route, I send a short connection request note like this: 

Hey [Name],

I hope you’re well!

I’m a freelance writer focused on the world of work for clients like Atlassian, Culture Amp, and Glassdoor. If you’re ever looking for some extra freelance help with the [Client] blog, I’d love to chat.

Either way, looking forward to staying in touch!

Kat 

That’s been effective occasionally too, even if it makes me feel a little slimier.

Prospecting and cold outreach are like anything else—there really isn’t one foolproof method here (I tricked you with that subject line, didn’t I? 😉). 

But that’s not what I want to focus on today anyway. Instead, I think it’s better that I give you a more encouraging reminder: I struggle with cold outreach and landing new clients too.

Have I had some wins with cold emails here and there? Of course. But it’s by no means a strategy with a bulletproof success rate. 

I currently have 12 unanswered connection requests sitting in my “sent” folder on LinkedIn. Many of them have been hanging out there for months—despite the highly-personalized and friendly message I included with each one. 

Similarly, in the past few months, I’ve been tagged on two different posts about freelance opportunities that were the perfect fit for me.

I did everything by the book from there: I thanked the person who tagged me, commented on the post to say I was reaching out, followed the directions for getting in touch, and sent what I thought was a perfectly-tailored introduction. 

And yet I didn’t hear anything back about either of those opportunities. Just silence. Womp womp. 

I also recently reconnected with a previous client to see if they had any upcoming work. They responded with their plans for the quarter and were enthusiastic about collaborating again. 

But after that? Crickets. Despite two follow-ups.

Listen, I don’t say any of this to be discouraging. Rather, I hope it serves as a gentle reminder that any sort of business development strategy comes with some wins and some losses. It’s part of the process (a disheartening part, but a part nonetheless).

I’m not immune to it. No freelancer is—and if they say they are, they’re either lying or trying to sell you something (or both).

So in case you think I’m over here getting a positive response to every single cold email and just drowning in new clients because outreach is easy and you’re just doing it wrong, let this be your takeaway: 

Nope. That’s simply not true.