Mastering Project Roadmaps

Tired of sinking a ton of time into every new project lead? Learn how to offer Roadmapping and get paid for the time you spend learning about and estimating client projects.

Most freelancers and agencies have it all wrong.

When they get a new lead, their entire focus is on selling them on hiring them for their project. They often spend hours in meetings, learning about the client’s project, and countering every single objection the client has to working with them.

Then they spend even more time putting together the perfect proposal. They stress out over the price and scope of the project – if it’s too low, they could end up losing money, or worse, end up with an angry client who spent more than they budgeted. And if the price is too high, they come off too greedy, losing the project or barely making a profit.

After pouring countless amounts of effort into perfecting their proposal, they send it off… and then the fear sets in.

“It’s been a few days, why I haven’t I heard back from them?”

“Did I screw something up?”

“Have I lost a great opportunity?”

They’ve already invested hours of time into a relationship with no promises and no guarantees.

And, unfortunately, this is par for the course. Every potential project goes through the same cycle of getting a lead, spending a lot of time trying to sell them, and then spending even more time writing a proposal.

This is time that could be spent billing a client or working on their business, but instead it’s spent gambling.

Here’s why it’s so hard to close client projects…

When you get a new project lead, you’re talking to someone who doesn’t trust you yet. They’ve never worked with you, and have no idea whether you can actually help them with their project.

You’re asking them to spend thousands, tens of thousands, of hundreds of thousands of dollars on you – when they barely even know you.

I can do this, I just need you to sign on the dotted line and send me a big, fat deposit check.

From the client’s perspective, you’re asking them to risk a lot on you.

First, they’re risking their budget. You’re asking them to spend tons of money on someone they have no track record with. (You know how it’s so much easier to sell to an existing client? It’s because you’ve already proved yourself to them.)

Second, they’re risking their time. If you screw up their project, they’re not only missing out on the money they spent on you, but they’ve also wasted days, weeks, or even months – time they could have spent moving their business forward..

The hardest thing to do is to ask somebody who’s never paid you to pay you $1.

And the more you’re asking for, the harder it becomes to close the deal.

But you don’t want to undervalue yourself. You don’t want to win more projects because you’re the cheapest; you want to win more projects because you’re the best.

You also don’t want to spend countless hours of unbilled time estimating and learning about projects, only to lose them and have to gamble on the next project.

Here’s the good news: you don’t have to.

What if you could get paid for the discovery and estimating work you’re already doing now?

Right now, you’re already doing a lot of work to learn about your clients and their projects.

You’re also taking time to think through their requirements and put together an estimate. (And, because you’re not getting paid, you’re probably rushing that estimate.)

Roadmapping is the key to changing all of this for your business.

So what’s Roadmapping? It’s a way to charge for a small, fixed-price engagement that delivers a small amount of value to a client, while preparing them to invest in a much larger engagement (like redesigning their website or building custom software.)

  • Roadmapping helps you convert more leads into clients because it’s a smaller, less-risky proposal for your clients.
  • Roadmapping helps you get paid for all of your time. This helps set the tone with your clients that your time is valuable, and not just the time you spend building or designing their projects.
  • Roadmapping gives your clients better, more successful projects. When you’re rushing through learning about your clients and estimating their projects because it’s time you’re not billing for, you’re shortchanging your clients.
  • Roadmapping helps you be a consultant, and not just a “doer”. When you sell a Roadmapping engagement to a client, you’re selling your expertise. This helps position yourself as an advisor and not just an outsourced, expendable resource.

Since I released Double Your Freelancing Rate over 4 years ago and described why Roadmapping is the single best way to convert more leads into clients, I’ve had hundreds of students followup asking for more details, more advice, and more examples of Roadmapping in practice:

“How do I convince somebody who came with me for a project to pay for Roadmapping instead?”

“What do I charge for Roadmapping?”

“How do I come up with what I actually offer in my Roadmapping sessions?”

“What’s the best way to sell somebody on a big project after we wrap up Roadmapping?”

After receiving so many questions about a subject that was such a new idea for so many, I realized that I needed to go deeper on the subject.

To be honest, I’ve always done Roadmapping (or something like it)… but I always gave it away for free. Now that I’ve added a proper sales process around it I’m not only getting BETTER clients, but getting them to hire me is significantly easier.

Laura Elizabeth, Designer
What's Inside

We’ve included live training, shot onsite at Neon Root’s HQ in Los Angeles, along with in-depth case studies, course notes, roadmapping agenda templates, proposal templates, and more.

The Course

Ben and I sit down and go through everything you need to know to successfully offer Roadmapping to your clients.

What Is Roadmapping?
Introduction To The Course
How To Qualify A New Lead
Using Intake Questions To Qualify
Selling Roadmapping To Clients
Moving From The Call To The Close
The Initial Call Or Meeting (Sales Demo)
How To Price Roadmapping
Hosting a Roadmapping Session
A Look Inside Rootstrap Roadmapping
Common Problems With Roadmapping
Client Case Studies

Interviews with clients who have bought Roadmapping engagements, along with consultants who have successfully used Roadmapping.

Marc Friedland
David Waldman
Mattan Danino
Kellan O’Connor
Documents, Swipe Material, and Extras

Get access to all the documents, templates, and swipe material you need to help you close high-value Roadmapping engagements.

Course Notes
Roadmapping Agenda Template
Pre-Roadmapping Client Worksheet
Brennan’s Client Intake Pack
Master Services Agreement Template
Roadmapping Final Deliverable Template
Rootstrap’s Agenda Slide Deck
Overcoming Objections Cheatsheet
Lesson Worksheets
The Roadmap to Roadmapping
Selling Roadmapping Checklist
Unpacking Rootstrap

The value or roadmapping is huge. A $5500 roadmapping process has turned into a $57,000 project. I couldn’t have done that without doing Roadmapping first.

Michael Napl, Marketer
Who's behind this course?

I'm Brennan Dunn, and for the last decade I've been working with clients. I started out as a freelancer, and after 3 years my business grew to an agency of 11 employees and a $2 million in annual revenue.

I love freelance consulting, but I'm hell-bent on helping other freelancers learn how to master the BUSINESS of freelancing. A lot of us (myself included) started freelancing because we're technically solid... but end up learning the hard way being successful is much more than just being good at what we do.

In addition to this course, I also write and podcast weekly for my audience of over 50,000+ freelancers. I also host two worldwide conferences for freelancers.

("What's with the robe, Brennan?!" We hosted our last European conference at an all-inclusive Japanese resort. It was a blast – and a bit weird! – presenting on stage in a kimono.)
Roadmapping Is For You If...
  • Your projects tend to always be different in scope or size
  • You’ve ever had a client get upset over the fact that what they paid didn’t match what they were quoted
  • You struggle to get clients to commit to working with you
  • You’ve heard “we’ll think about it and get back to you…” way too many times
  • You want to offer a stepping stone to working with you – a Roadmapping Engagement
Who Roadmapping Isn't Good For...
  • You have a low price productized service that doesn’t require much convincing to hire you
  • Your clients generally are looking for the cheapest vendor and aren’t looking for a partner (and you’re OK with this)
  • You really don’t want to get involved in the businesses of your clients
  • You’re in such high demand that virtually every prospect you talk to becomes a client with little effort on your part
Get Instant Access
Join hundreds of other freelancers who are now offering high-value Roadmapping engagements to their clients
Complete Course
  • Over 5 hours of in-depth instruction and case study videos
  • Worksheets and accountability that help you create your own Roadmapping offers
  • A downloadable cheatsheet that maps out and summarizes the entire course
  • Lifetime access to the DYF Community (live chat)
  • Contracts that help you close Roadmapping engagements
  • All the beautifully designed templates you need to sell and host Roadmapping
  • Raw sales call recordings, email swipe copy, and other extras
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