Upselling to a Customer: 4 Steps to a Confident Pitch

Written by Bethany Johnson on November 16, 2017

As a freelancer, you want to focus on your craft. Sure, you’re willing to do the other stuff — administering taxes, marketing, invoicing and even upselling to a customer — but your passion is to produce and deliver the goods. When it’s time to increase your income, that familiar feeling of dread may creep in. Selling can feel downright unnatural.

Here’s the truth: I don’t know a single solopreneur who enjoys pushing themselves on others for the sake of a sale. You’re not the only one that feels the “ick” factor when approaching a client for more work. Fortunately, there are ways to make the practice (and it does take practice) easier. Take this upselling approach, and you’ll not only feel better, but you’ll likely have a higher monthly income, as well.

1. The Power of Perspective

Don’t start strategizing the Big Ask by brainstorming what to say. Don’t even worry (yet) about squashing objections. Instead, back up and start at the beginning. The trick to a successful upsell is a change in perspective.

First, you must genuinely believe your add-on item or service will benefit the client. Offering to place an ad in your town’s local newspaper to promote your client’s event, for example, doesn’t benefit them if the readers aren’t geographically close to the venue. Upselling to a customer who doesn’t really need the addition will invite those sleazy feelings you dread. Before anything else, envision your clients using your proposed add-on. It needs to make their lives better. This way, the “sales-y” awkwardness dissipates naturally.

Not sure how this would play out in your client communications? No problem. Here’s an example of how I recently posed my perspective in an email:

“Dear __________,

I’ve enjoyed getting to know your vision. I’ve especially liked seeing how, together, we’ve nailed it on our last four projects. As you know, I’m an idea machine, so I’ve been generating possibilities as a byproduct of our work. I think project B, for example, could use a fresh round of inspiration from ___________, an effort I’d even consider spearheading, should you agree it’s a value added. We can talk more about these possibilities on our regular Tuesday call.”

2. Determine an Approach

Next, decide whether to cross-sell or upsell. This decision is the difference between offering an additional relevant item or an upgraded version of the original order. The best time to upsell (or, offer an upgrade) is just before a client commits to a sale. This means they have already decided to contract your services, and may appreciate knowing about your more robust premium package. Now’s the time to list the ways they would benefit to elevate their experience.

In action, the upsell method looks a little like this:

“Dear __________,

Good choice. Someday we’ll both look back on this strong start as the crossroads it is, and only then we’ll know exactly how beneficial the partnership is. And about those benefits, there’s a discount per-project rate for clients that sign on now for __________, something your team could especially use, considering ____________.”

If you’re cross-selling, however, wait for a milestone in your original contract’s timeline. Let’s say you’re a website designer, and your client is raving about the landing page you just created for the blog portion of their site. Now would be a great time to offer to build out their social media pages so they can hit the ground running once the entire project is complete:

“Dear __________,

So happy to hear you loved our latest piece. It’s awesome to see it taking off on social as an organic conversation-generator. I’m working on the ______________ now. Speaking of deliverables, how’s your ___________ situation? Could that use a similar dose of fresh inspiration? I do offer bundled packages should you want the same results across every medium. No need to decide now — but let’s add it to our regular video chat.”

3. Make It About Ideas

Establish a track record of pitching ideas to your clients regularly — free of charge — so that one day, when you have the brilliant idea to upgrade or add to their service, they’re already used to your creative suggestions. Here’s how I gently offer that angle:

“Dear _________,

Yes, you’re right, that _____________ was a great idea. Turns out it really resonated with audiences. Your help narrowing down all my ideas has been the perfect ingredient for these surprisingly well-received jobs. About that: As you may have suspected, I have many more ideas percolating that you may want to kick around with your own team. In fact, I keep a list! Want to run through it this Friday over coffee?”

4. Clarity Is Everything

Recently, I hired another freelancer to help me perform light research for my own writing assignments. A few weeks into her work for me, she asked if I’d be interested in her other virtual assistant services. “Like what?” I asked, curious.

“Oh, you know, email marketing, invoicing, social, stuff like that,” she answered.

Answer: No, thanks. And that’s only because the offer wasn’t clear. Had she come to me with a clear proposal, including scope, results, timeline and exact costs, I likely would’ve relished the extra help. Clarify your basic, business and premium packages in a graphic somewhere on your site, along with the optional accessories for anytime add-ons. This way, your client can refer back to the table and continually compare. Then the idea is fresh and clear in their mind once you mention their options.

Here’s an email upsell proposal I would’ve jumped on:

“Dear Bethany,

I trust the reputable sources I’ve been digging up for you have boosted your site’s authority with the great link juice those sites are so good for. Another great way to improve your traffic is through strategic social media promotion, a skill which I happen to enjoy exercising for clients. In 4 weeks, I estimate I’d be able to have a half-dozen of your articles pulling in a few dozen unique page views a day via ____________. The initial push would cost $___, and after that, an ongoing arrangement would run between $___ and $___. It’s not dramatic growth, but it’s steady, and over time, that would give your site quite a boost in traffic and rankings. Let me know if you’d like to discuss a customized package on Monday afternoon when we catch up.”

Of course, the above scripts should just serve as examples for your reference. In order to be successful when it comes to upselling, you must find out what truly matters to your client, and use that information to maintain a good, mutually beneficial partnership. If you’ve done the extra work of ensuring that an add-on will benefit your client, decided which approach to take, established a track record of offering great ideas and been clear on price and scope, an upgrade is one of the very best ways to boost your income as a freelancer.

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