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What is Project Roadmapping and When Should You Use It?

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As a freelancer, you’ve probably experienced what it’s like to spend hours talking with a potential client, learning about their needs, and writing a proposal, only to have them “go in a different direction” or worse — never get back to you at all.

Most clients don’t clearly define the purpose of their project or the scope of work before they begin contacting freelancers. In fact, many freelance clients expect you to help them define their project.

That means when their email lands in your inbox, you’ve got to invest time and energy helping them define the project to a point where your expectations on price, timeline, and scope of work are aligned toward the appropriate business goals.

Then, you have to document all of that information in a proposal and contract.

That’s a lot of free work — and there’s no guarantee the client will hire you.

But if you skip this part of the process and start work without properly aligning expectations, you’ll be putting yourself, the client, and the project at risk for catastrophic failure.

So, wouldn’t it be great to get paid for all the time you spend defining the project with a potential client? That’s what Project Roadmapping is all about!

What is Project Roadmapping?

Simply put, Project Roadmapping is a way for you to get paid to help a client plan their project. Some freelancers call it a “Strategy Workshop”, but you can call it whatever you want. I even had one client call it a “Feasibility Study”.

Regardless of the name, the idea here is that you’re offering a productized service to any freelance client who needs more help defining their project than you’re willing to provide for free.

Definition: A productized service is any service you can offer at the same fixed price in a predictable, repeatable way. It’s just like selling a physical product, but you’re providing a clearly-defined service instead — just like Project Roadmapping!

Like many freelancers, I’m willing to invest a small amount of unpaid time to see I’m a good fit to work with this client on their project.

You can think of this as a “Free Consultation” and even market it to potential clients that way on your website. This is a great way to collect emails and generate leads!

For example, when a potential client fills out my project intake form, I’m happy to spend a little time emailing them, setting up a 30-minute discovery call if needed, and writing a proposal.

But what I can’t do is gift every potential client 5-10 free hours of phone calls and emails to help them define their project just so I can write a proposal that they might not even accept. That’s too much free time and too much risk.

To minimize that risk and get paid for my time, I can offer potential clients a paid Strategy Workshop or Project Roadmapping service that includes:

  • a fixed set of tasks (phone calls, emails, meetings, etc)
  • a fixed set of outcomes (documentation, proposal, contract, etc).

Whether they hire me or not, I’ll still get paid for my time, effort, and ideas.

When should you use Project Roadmapping?

Not every project requires a Strategy Workshop or Project Roadmapping service. In fact, Project Roadmapping works best for complex, high-risk, high-value projects.

If a client needs you to design some banner ads, social media graphics, or even a basic marketing website, there’s probably no need for paid project planning.

If you want to get paid for your time writing a proposal and planning small projects, you might call that a “paid consultation” or something similar.

But if your client wants to bring a new product to market, create a mobile app, or redesign a marketing website that drives their entire business, I’d offer or “pitch” a Project Roadmapping workshop.

I only offer Project Roadmapping to clients when I think we’re a great fit to work together on a large-scale project, but the scope of work isn’t defined enough for me to write a proposal.

At my company, Matthew’s Design Co, these can be marketing websites, digital products (such as cloud-based software), or mobile apps.

Here are some ways to determine if you should offer Project Roadmapping to your client:

  • If they have a clear understanding of the goals, project requirements, budget, and timeline, you don’t need to offer Project Roadmapping.
  • If the project is relatively simple and low-risk, you don’t need to offer Project Roadmapping.
  • If you think you can clarify ALL important details in a short amount of time, you don’t need to offer Project Roadmapping.
  • If the project is complex and needs more definition before you can write a proposal, you can offer Project Roadmapping.

What should you include?

The beauty of Project Roadmapping is that it can include anything you want. There are no right or wrong answers!

This is a service that can be tailored to your specific business. You can call it anything you want (such as a Strategy Workshop) and you can even get creative by offering multiple tiers of that service.

Just keep in mind that the goal is not only to define the cost, timeline, and scope of work, but also to make the client feel confident about moving forward with the project. Therefore, you should include anything that helps achieve this goal.

The goal of Project Roadmapping is to make the client feel confident about moving forward with the project.

Here are some things you might include:

  • A fixed number of phone or video calls (establish a clear agenda for each call)
  • Documented research and analysis (users, company, competitors, market, etc)
  • A written proposal and contract

For smaller, simpler projects, I may only include basic research of the users and competitors — or I may not suggest Project Roadmapping at all. In this case, it’s likely that I can verify we’re executing the right project against the right goals through a few emails and a complimentary phone call.

Remember: Don’t overcomplicate the process unless it’s absolutely necessary!

For larger and more complex projects, I might conduct user research, a competitive analysis, and a market landscape overview. If I’m helping a client bring a new product to market, I might include a customer acquisition strategy along with pricing and sales projections.

In my business, I only offer a Project Roadmapping Workshop to clients who are trying to bring a new product to market, such as cloud-based web software or a new mobile app. The cost, timeline, and deliverables for the Project Roadmapping workshop are always the same, which is what makes it a productized service.

How much should Project Roadmapping cost?

Again, Project Roadmapping is a service you can tailor entirely to your business. But the idea here is to make it a no-brainer decision for the client. For example, if your projects usually fall in the $5-10k range, you could offer a 3-hour Strategy Workshop for $499 where you have a detailed discussion with the client about their needs, document all your findings, ask clarifying questions, and write a proposal.

A project at this price point is relatively low-risk and shouldn’t need more than half a day of strategic work to make sure you’re executing against the right business goals.

If your projects usually fall in the $25-50k range, you can offer a more comprehensive Project Roadmapping Workshop that includes more meetings, documentation, and research. Something in the $1,500-$2,500 range might be appropriate.

In general, I haven’t found a need to spend more than 2-3 weeks on strategy work to close even six-figure deals. I based the fixed cost of the project roadmapping session on time, not value (since that’s one of the things we’re trying to define!)

So for most freelancers, I don’t see a need to charge more than $5k for strategy and that would be for very high-budget, high-risk projects.

Now, put the pieces together from the client’s perspective: would they be willing to invest $2,500 and two weeks of time to validate the need to spend $50-100k on a 12-month project?

Yes! That is a no-brainer decision for any client who’s serious about giving you that project. In fact, they’ll be delighted and relieved that you offer such an option (because most freelancers don’t!)

In the end, you have to be happy with what you’re getting paid for your time and effort and the client has to feel like they’re getting a good deal. That’s your goal for pricing Project Roadmapping sessions!

Practical Examples

For example, two clients came to me each wanting to bring new software products to market. They had little more than an idea at the time, but I knew they would require product design, product development, a marketing website, branding, project management, etc.

These were risky, expensive, long-term projects that demanded more planning before I could even attempt to write an accurate proposal.

My ballpark pricing was well into the six-figure range.

Rather than spend days or weeks planning the project for free and asking the client to commit to an expensive and risky project upfront, I suggested that we conduct a Project Roadmapping Workshop.

This $2,500 fixed-price engagement would let me work with them for about 2 weeks and allow me to:

  • Have multiple meetings and phone calls
  • Do market research
  • Understand their audience
  • Learn about the product and idea
  • Prepare a competitive analysis
  • Define the product features
  • Define the marketing website needs
  • Document all my findings
  • Prepare an accurate cost and timeline
  • Write a proposal and contract

In this case, paying for a Project Roadmapping Workshop was a no-brainer for the client.

I was asking them to invest $2,500 to find out exactly what the project will require instead of committing to a $100k+ complex and risky project.

Even if I convinced them to hire me without paying for a Project Roadmapping Workshop, I would’ve started the project by doing this same research.

But by separating the initial strategy work out into its own separate service, a few key things happened:

  • We got to work together on a low-cost, low-risk engagement
  • The client trusted me enough to hire me
  • The client got extremely valuable information and insight
  • I increased the likelihood of the client hiring me for the full project
  • I established a reputation with the client
  • The client paid for my time and effort

Closing Thoughts

Project Roadmapping is an excellent way to make more money as a freelancer, make your clients happier, set better expectations, build more trust, and land bigger projects. What’s included and how much it costs is completely up to you.

If you want to learn more about Project Roadmapping, watch this video which I shared in The Freelance Institute — a community I created for freelancers and remote workers.


Have more questions about freelancing?

If you’ve got a lot of questions about freelancing (like the nuances of how to suggest Project Roadmapping to a prospective client), I’d highly recommend joining me in The Freelance Institute!

It’s a community I created for freelancers like you so I can offer tailored advice and answers to your specific questions. Just post a question and you’ll not only get a personal response from me, but other freelancers from around the world too!

About Matt Olpinski
I've been freelancing since 2009 and have worked with over 100+ clients including some of the biggest brands in the world. I later started my own company Matthew’s Design Co. and now teaches 50,000+ freelancers each year how to succeed through his personal blog, newsletter, and community for freelancers.