3244 9:06 Q&A

Q&A: “How do I upsell without sounding pushy?”

Great contracting work often reveals the next problem to solve. Here’s a simple script that turns an “upsell” into an obvious win for the client—and leaves everyone feeling good about the extra invoice.

9:06

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Episode 3244

Finishing a project can be like pulling drywall: patch one hole and you see three more. For service pros, the dilemma is real—do you point out those holes (and offer to fix them) or stay silent to avoid the whiff of upsell desperation? Done with care, offering additional help isn’t pushy; it’s responsible. The trick is timing, evidence, and clear outcomes.

"I write site copy, clients love it, then I notice their funnel is a huge problem I could fix for a fee. Every time I inch toward offering the necessary audit, I feel like a pushy used-car salesperson. Any tips on framing an upsell so it lands as genuine help and not ‘my contractor is trying to wring more money’?"

Listen to today's episode to learn more...

Yours in the revolution,

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Read the full transcript

This transcript was generated from the episode audio and may contain minor errors.

[Music]

Let's talk about upselling. How can you successfully upsell without sounding pushy? And the thing about upselling is we all encounter upselling all the time and there's a way that it happens that actually feels totally normal and natural and not annoying at all. And we've all been on the other side of things where it's like somebody keeps pushing, would you like this, would you like that? And you're like, this is just too much, dude.

So it can go either way. But I encourage you to think about how could you take the products or services you're offering, whatever offer you're trying to develop and think about what are the logical extensions or upgrades that this person might want to create that environment where people are happy to say yes. So we're gonna try to give a script, gonna give a script to our caller today that turns an upsell into an obvious win for the client, leaving everybody feeling good about that extra invoice. Done with care, offering additional help is not pushy. It is actually being responsible.

The trick is timing, evidence and clear outcomes. Leela is our caller. We're gonna hear from Leela with her detailed question and my answer right after this. [Music]

Good morning team, Leela here, a freelance copywriter in New England. I write side copy, clients love it.

And then I noticed their sales funnel is a huge problem I could fix for a fee. Every time I inch toward offering the necessary audit, I feel like a pushy used car salesperson. Any tips on framing an upsell so it lands as genuine help and not my contractor is trying to wring more money? Ideally, I'd like to make this a win-win for everyone involved, including me of course, but also the customer. [Music]

- Leela, if you are noticing that your clients have a problem, then I would argue it's almost your responsibility to suggest a fix or at least to kind of point out, hey, I'm writing copy, you like the copy, but actually you're having a hard time converting people because of this funnel.

And there's some things you could do to increase the efficiency of that process, increase your conversion, et cetera. So I think what you do is you position this as a two-step framework. Step one is to diagnose the problem, just basically like you deliver the original copy that you have been contracted for, maybe you schedule a quick hands-off call. And as part of that, you say like, hey, like, look, your email capture rate is like way below the industry average. I can show you what that means for your sales, like you're missing out on a lot of sales basically.

And then the step two is like your outcome anchored offer. So your offer is rooted in an outcome, like we're gonna fix this for you. I can audit your funnel, it's going to greatly improve your email capture rate, which will then affect your conversion rate for everything. And I charge for that, I charge $600, let's say, just to throw that out for the audit. And so that way you've kind of presented the problem and offered a solution, they don't have to say yes, maybe there's a way they can fix the problem on their own, but at least they're aware of it now.

And they can also see like, oh, if we pay a little bit more, then we're gonna have a better outcome. So again, it's like creating this win-win solution. I think that's what you do. That's how you create a script that doesn't feel pushy. It actually feels welcome and permission-based.

So you lead with data, get permission to explain, and then give them a fixed scope solution that is connected directly to their revenue. Makes everybody happy, at least that's the idea. Listeners, let me know what you think. If you have a question, sidehustleschool.com/questions, notes pages for every episode up there on the site as well. We'll continue to feature listener questions along with updates from other listeners as they launch and grow their projects.

Thank you so much for being out there. My name is Chris Guillebeau, this is Side Hustle School. [Music]

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