Writing Proposals That Win You Projects

This year I probably bit off more than I could chew.

I’ve been sharing a lot of it over Twitter, but to sum things up:

1. Bought a new house, closed on January 2
2. Because this was an upgrade in square footage, we did the (stupid) thing and rushed to fill in the blanks with new furniture, etc.
3. The house is 100 years old, and was built in a time when attics were built super well. I’m talking high, old growth beams and space. Decided to convert it into a swank home office.

I’m juggling the running of two different companies: Double Your Freelancing (👋) and RightMessage. My days are already jam packed.

So a “let’s hire a ton of contractors to redo the attic” project – while essential, considering I was spending my days hunched over a MacBook in the dining room – probably wasn’t all that smart of a move to make. Especially while the proverbial dust was still settling in the new house.

I get an email or two a week from someone who just sold their first Roadmapping session.

Usually, the email includes something like…

“HOLY CRAP THIS WORKS. They loved it! Not only do they want to move forward with the project, but they let me know a few days later how appreciative they were. And I got paid!!!”

Roadmapping is paid discovery (which is a fancy way of saying it’s a way to get you and your soon-to-be client on the same wavelength about their project, goals, risks, and so on.)

At first blush, it might seem like it’s a way of getting paid to produce an estimate. But it’s much more than that. Roadmapping allows your client to gauge the viability of their project and make an accurate decision about whether it’s worthwhile to pursue the path they thought they should go do… or to find another path to the goal.

Why does this matter?

Because you want successful clients.

Now that Mastering Project Roadmaps has been out for a few weeks (and is now fully hosted right here on DoubleYourFreelancing.com – heyoo!), I wanted to share with you three reasons why you should be mandating Roadmapping with each and every one of your clients.

A quick recap of what Roadmapping is:

Here’s the typical sales cycle for a freelance consultant:

1. We get a new lead.
2. We qualify them (by making sure they’re serious about the project and have a budget that we’re willing to bite at.)
3. We spend some time learning about their project and their goals, with the intent of moving the lead closer to the point of letting us issue a proposal.
4. We write a proposal.
5. We send it off and cross our fingers.
6. Sometimes we have a few more meetings to address any concerns the prospect might have.

Roadmapping changes the usual sales cycle by offering a low cost, low risk productized service as a pre-requisite to doing any project together.

If you’re used to building websites for clients, Roadmapping would have you discussing what you’re building and why the client needs it. It’s a high-level discussion about their business that includes a concrete set of deliverables, like wireframes, workflow mockups, story cards, and the all-important custom Roadmapping report.

Roadmapping allows your clients to get a feel for what it’s like working with you without committing to an expensive and time-intensive engagement. And Roadmapping allows you to deliver early value to clients and ensure that you’re able to do the due diligence required to put together a solid proposal.

Have you ever worked on a project where everything was seemingly going great…

Every few days, you’re meeting with your client to discuss your progress. Your project management tool is buzzing with activity. And your invoices are getting paid.

And then at the 11th hour, with the finish line is in sight, you get that call every consultant dreads:

“We need to talk.”

And then you panic. What the heck happened? Everything was going great… right?!

The client then rattles off a list of grievances:

This isn’t what they wanted. They’ve spent all this money and aren’t happy with what they’re getting. They don’t know why it looks the way it looks, functions the way it functions, or reads the way it’s written.

They’re unhappy.

As I’ve been working my way around the Internet this summer teaching the fundamentals of the DYFR framework, I almost always end up getting asked the same question from people after I describe my method of writing proposals:

What if I can’t guarantee my client a specific return-on-investment (ROI)?

A quick refresher if you’re new: One of the concepts of the framework is to anchor your costs against what I call the Financial Upside of a project, or the long-term value of the project for the client’s business. This makes it so you don’t end up pricing yourself in a vacuum, but instead have something (ideally less than what you’re asking!) to contrast your price to.