Roadmapping Session

Before starting on any journey, it’s wise to plan ahead.

Before I engage with a new client on a project, I do a roadmapping session. In essence, roadmapping is where you and I work together to take a really deep dive into their business, the problem you’re trying to solve, and all the possible solutions we might apply to the problem, then choose the best and create a roadmap that you can use either with me or another freelancer.

It’s a low-cost, low-risk engagement that aims to make sure we do things right the first time.

I do roadmapping with clients because I’ve consistently found that it:

  1. Produces a better finished product, often on a smaller budget.
  2. Produces an accurate estimate of the project timeline and cost, preventing irritating and costly overages and delays.
  3. De-risks your investment in a project and makes sure the money you’re spending actually generates a return.

Roadmapping helps me deliver more bang for your buck.

My Roadmapping service is a way to help you understand where you’re going, how long it will take, how much fuel (budget) you should expect to use, and what risks face us along the way.

What to expect


You: We’ll go into more detail about you, your company, your customers, and your business model.

The Problem: Our team will learn more about your project, and specifically what business problems lie behind it.
The Payoff: We’ll dive into the project in more detail, and establish exactly how this project will be financially beneficial to your business and yield a return-on-investment.

What defines success? What defines failure? The more we learn about your business, its problems, and the goals that you have, the better we’ll be at being able to help you define a Roadmap to reaching those goals.


After we’ve learned as much as we can about your business and what you want tomorrow to look like, we’ll assess and analyze the risks in moving forward. Your team and ours will bring forward anything that could keep this project from being successful — maybe the budget’s too low, the timeline’s too tight, or there will be a degree of research and experimentation needed.


We’ll spend the majority of our time together really digging in to how the business problem at hand can be best solved. What should be done? What maybe shoudn’t be done, at least not yet?

Together, we will put together a start-to-finish Roadmap for your project. This will help you avoid any dead ends and wrong turns. And we’ll also ensure that before you start down the path of executing on your project that you have a good understanding of how much time and money will be required.


Now that we’ve really fleshed out this project and have come up with a few paths that will help you solve the problem you face, we’ll revisit the risks we identified at the beginning of our session and see if they’re still a concern.

How to Prepare

Our roadmapping session should last around 1 hour. In this session we’re going to dive deep into your company, products and goals so we can come up with a rock-solid plan to get you from where you are now, to where you want to be.

You don’t need to spend long preparing for our session but there are some things you can do beforehand which will give us a head start on the day:

  1. Make sure the intake questionnaire is filled out. You had an vision questionnaire at the start of this engagement. Go back and make sure everything is filled out and add any extra details you think might come in handy for our session.
  2. Provide access to your analytics: Add to your Google Analytics account or bring any data about your analytics to the session.
  3. Make sure you have up to date records on product sales
  4. Bring along any talking points you don’t want us to miss I want to make sure you get as much out of this session as possible. I will be bringingalong my own thoughts and ideas and we’ll be talking business owner to business owner. But if there is anything you don’t want to miss, make sure you have a list to being up in the session.

The only goal with roadmapping is finding the best solution.

You’ll be incentivized to avoid planning for anything that
isn’t necessary to the success of the project. This produces a better solution on a tighter budget.

Roadmapping ensures you and I are not just saying “yes” to everything. It prevents us both from spending a lot of time and money creating a solution that wasn’t actually the right concept in the first place. It provides an accurate estimate for the budget,
scope, and timeline of the project