Writing proposals that win you projects

What Should You Ask Of Your Clients Prior To Roadmapping?

By Brennan Dunn


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.

You don’t want your portfolio to be a graveyard of 404 links. The more successful your clients, the more successful you are. You’ll get more referrals, repeat work, and you’ll be able to produce some incredible case studies. (We often think success means “the project is technically complete.” Wrong. Success is when the project achieves the business goal at hand.)

Today I want to share with you how I prepare my clients for a paid Roadmapping session.

Now, there’s a strong chance I do something a bit different than you. I work with already profitable companies who, given a week or two of work doing some segmented personalization and marketing automation work, can yield $100k+ in ROI a few months after the engagement. Technically, I end up writing a lot of Javascript, HTML, CSS, and setting up workflows in Drip.

When an organization books me for a Roadmapping engagement, I send them over an invoice and my contract. Because my contract includes a non-disclosure clause, this means that the client can now safely share financial details with me. This is huge. The more data I have about their financials, the better able I am at making sure taking on this project can yield a return-on-investment (and you better believe I constantly remind my clients of this.)

I then take a Google Doc template of mine and modify it based on their business and what I already know about them. Here’s an example:

1. Business

  • What products do you have available to offer now?
  • How are your products cross-sold or up-sold? Do you have anything in place that increases the customer lifetime value besides customers deciding to come back for more?
  • What are your best-selling products? Worst-selling? And why?
  • Of the 500k-1mm visitors who visit [REDACTED] a month, what % of them convert to opt-in or customers? How many net new opt-ins do you get a month? New customers?
  • How many customers do you have total? How many buy just the one-off products? How many have joined [REDACTED]?
  • What email marketing work, if any, are you doing now? (Broadcast newsletters, subscriber onboarding, post-purchase up-selling or cross-selling, etc.)

2. Demographic

  • Define your ideal subscriber? Your ideal customer?
  • For your ideal customer, what do they buy first? What leads them to your website and to buy?
  • What resistance do people have in buying your products?
  • For your monthly [REDACTED] product and upcoming 3-figure online course, what do you think separates these customers from the rest of your subscriber base?

3. Financial

  • Without introducing any new products or getting an increase in monthly opt-ins, what realistic monthly sales figures would make this project a success? What increase in monthly sales would make this a home-run?
  • What is the value of a subscriber? (Easy formula: Total annual sales + revenue divided by subscriber count)
  • What is the average value of a customer? (Easy formula: Total sales divided by number of customers)
  • What percentage of customers buy just once, and what percentage buy again?
  • What is the customer lifetime value (CLTV) of those who buy once vs. repeat buyers?
  • What is the value of a subscriber who comes organically / via social media / via paid ads? (Don’t worry if you can’t figure this out just yet.)

I know that 99% of my clients can’t answer all of these questions.

And that’s OK!

Because in asking these questions, I’m giving them an idea about what kind of data they’ll soon have at their disposal.

I’m also making a statement with these questions. Two things are made very clear:

  1. I care primarily about their business. Outside of one question, I haven’t asked anything about marketing automation or anything technical.
  2. I care about the numbers. I get paid in dollars, and I know that my clients would appreciate getting more dollars back than what they’re paying me. They want an investment, and by focusing so much on their business and financials, I’m letting them know that I understand that they need an ROI.

Armed with this data, I arrive for the meeting with an agenda.

This agenda has me focused on taking the data they’ve given me and finding ways to improve their business doing what I do best: writing Javascript, HTML, CSS, and playing around in Drip. (If you want to learn how to do the sort of consulting I do for my clients, go here.)

The desired outcome of Roadmapping is to come up with a realistic plan of action on how we can get their business from where they are today to where they need to be tomorrow. I then draft up some technical requirements and come up with a project estimate, which I include within the report that I deliver a few days after the Roadmapping session.

(And because my quote is in a REPORT and not just a PROPOSAL, it’s perceived as being much more valuable.)

Hopefully, this gives you a good starting point. You’re going to want to come up with your own set of questions that you send to new clients prior to Roadmapping, and it’s OK to come up with these questions from scratch anytime you get a new client — especially if the kind of projects you take on vary greatly.