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6 Ways to Upsell Clients Without Being a Sleazebag

upsellSo you’re a freelance writer for a living, and it’s great. Awesome, even. You love sitting at your desk at home, knowing you can get up for a cinnamon roll any damn time you please.

Not so great? The fact that you can’t always guarantee where your next assignment (or cinnamon roll) will come from.

What to do? Well, naturally there are plenty of tricks for landing freelance writing gigs, but one of the most effective is to look to current clients. They often have more work, even if they don’t yet know it. That’s where you come in.

Unfortunately, upselling clients while negotiating contracts, or after you’ve already done work for them, can feel super icky. Coldcall-y, even. Blerg. So just how do you upsell someone you know/like/care about/live next to/possibly buy your groceries from without turning them off forever? Without being a sleazebag?

Good question. Here’s are six ways to Do The Thing.

1. Offer a Site Overview

One of the best services I perform for my clients is a site overview. This is a quick 1- to 2-hour consulting project in which I’ll look over everything in their online footprint, including social platforms and other digital properties, then let draw up a report. It’s low-cost and helpful to them, and since you almost always find work that needs doing, you can then recommend it. When new clients ask about web copy, I suggest this first. I can do the real project after, but with more clarity on both ends.

2. Talk to Them About Their Sales Funnel

Most businesses have a sales funnel in place already – even if it’s underfed and crappy, which is often the case. If they don’t have one yet, even better. Web copy and blog posts (the two most common types of assignments I do) are critical, but so are email newsletters, free downloads, ebooks, resource libraries and other types of pull marketing collateral.

Make sure your clients know these are an option for them, and how you can help beef up that funnel.

3. Explain the Benefits of Updating Copy

Some clients will come to you for a bit of new copy or some blog posts, and when you head to their site you see it hasn’t been updated for years. This is when you step in and nicely explain how bad old copy is for SEO, as well as what you can do to help.

4. Test the Blog Waters

Blogging is important. You know it; I know it. Clients, though, might not know it … or might not believe. As the professional, you have the opportunity to explain this to them, and you should. I always offer my blogging services when I wrap up a web copy project, because it’s the natural next step. I’m not pushy, but I try to be pretty firm on this front.

5. Update Clients on Pricing

As one does, when one has a growing level of expertise, I occasionally raise my pricing. Any time I do so, I reach out to current and past clients to let them know what my new rates are. You might think this counterintuitive, because if they haven’t given you more work yet, why would they do so now that you’re charging more? But actually, seeing your increasing expertise in a dollar amount can bump up someone’s enthusiasm about working with you, because you’re seen as a hotter commodity. Do it. It works.

6. Just Check In

That said, there’s nothing wrong with a “Hey, how’s it going?” If you haven’t heard from your client for a while, you can always reach out and ask how their business is going, reference their goals from your last conversation and let them know if you have any additional services they might be interested in. You don’t want to do this more than once, because, stalking. But a quick check-in is recommended if you haven’t heard from someone in a while – for me, 2 months is about right.

Of course, these strategies don’t always work. And if they don’t … hey, who cares? Rejection from a client is no different than rejection from an agent or editor, and if they already like you, they’ll probably be considerably politer about it. Plus, rejection has always been and remains the first step to successful freelance writing, so consider this part of your growing craft.

As a freelancer writer, whether already successful or just getting started, it’s your job to put yourself out there. Existing clients are among the best sources of work in the writing world, and ignoring them is just plain foolish.

And we know that’s not you, right? So go forth and conquer.


Sarah Moore, writer


Sarah Moore is a professional copywriter and the owner of New Leaf Writing, where she helps clients and other writers get their messages across more effectively. She just published a book on creativity entitled Get the Hell Over It: How to Let Go of Fear and Realize Your Creative Dream.

{ 6 comments… add one }
  • Hello, Sarah, Great article I just read and totally agree with your point. Thanks for sharing this wonderful article with us.

  • Hi Sarah, You have written some good exercise to make our clients happier than ever.
    It was nice reading the informative post.
    Thank you

  • Hi Sarah, it was great going through your article . i liked it very much . I hope your suggestions work for my online business. Thanks a lot

    • Sarah Moore

      I hope it helps too!

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