If you already have a free resource and are considering a paid workshop, I'd start by asking what someone can do in the workshop that they couldn't do with the resource. If the only difference is more information, the workshop may just be a longer version of the same thing. If people can bring a specific problem and leave with a decision, that's a different reason to sign up.
This came up when I was reviewing a business that had a free resource and was considering a low-cost workshop as a path toward a larger program. The sequence was easy to draw. What I wanted to understand was why someone would choose each option, even if they never took the next step.
I like to think of the workshop as somewhere a person might arrive first. That forces me to make it useful on its own, without assuming they've read the resource or are considering buying the program.
The same problem can call for different help today
Imagine you help small business owners follow up with prospects. One suspects conversations are slipping away but doesn't know where. Another knows it happens after they send a quote and wants to fix it this week.
The first might benefit from a worksheet that traces the inquiry, the quote, and the follow-up. The second might prefer a workshop where they bring a real quote and leave with a sequence they can use. Both want to sell better. One needs to locate the problem; the other is ready to work on it.
That changes how I think about price. If the workshop gives someone time to work through a case, get feedback, and make a decision, I can explain why it costs money. If we just add two hours of explanation, I still don't know whether that improves anything for the person signing up.
It changes how I'd present the options, too. I wouldn't make someone who knows where the problem is download the worksheet first. And I wouldn't steer someone who is still figuring it out straight into an offer that takes more time, money, or preparation.
What I'd try to learn from each entry point
With a free resource, I want to know whether people recognize the problem and can use what we give them. A download tells me the promise caught someone's attention. What I want to learn next is whether the worksheet helped them spot anything: a step they skipped, a question they hadn't asked, or a point they didn't know how to check.
A workshop lets me see something else: what happens when someone tries to solve the problem with their own information. Maybe they realize they never agreed on when they'd follow up. Or they arrive with a good sequence and discover their quote doesn't explain what's on offer. That can help me improve the workshop and see what might be worth teaching next.
A workshop sale is useful evidence. It doesn't tell me the person is ready for the larger program. Before recommending it, I want to know what they're missing and whether the program can help. If they left with what they needed, solving that problem is already a good outcome.
If I test both ways in, I want to be able to tell them apart. It's enough to know where someone came from, what they expected, and what happened afterward. I don't need a big system to start, but I do need more than one contact list with no context.
When I'd stick with one
Every entry point adds work. Even a free resource needs an explanation, a way to deliver it, and someone to respond if it doesn't arrive. A workshop needs preparation, scheduling, and delivery. If both options are for the same person at the same moment and promise nearly the same thing, I'd test one first.
And if the team is still figuring out why the main offer is hard to sell, I wouldn't assume another product is missing. I'd listen to a few conversations. Maybe people don't understand what they'll get. Maybe they do, but need to solve a smaller problem first. In the first case I'd explain the offer better. In the second I'd consider another way in.
My question for either option is: What can someone do after this first experience that they couldn't do before?
If the answers are different and each helps someone at a recognizable moment, there's a reason to offer both. If I can't tell the answers apart, I'd rather make one work well.
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