Roadmapping Sessions

Three months ago, my dream client came knocking.

They’re an established local business and they were looking to invest in growth for the future. They wanted to work with me on a large, multi-month project — and it was a perfect fit for the services I was offering. I was ecstatic. Everything felt great. The client saw value in my services and I wanted to work with them.

As a first step, I proposed a small kickoff project — a Roadmapping Session — to review the outcomes they were looking to achieve and test working together. We scheduled the meeting for later that week.

Then, on the day of the meeting, less than an hour before we were supposed to start, I received an email from them, telling me that they needed to cancel. They wouldn’t be able to afford the project we were discussing or the fee for the Roadmapping Session. They had, literally, no money in the bank.

Was I disappointed?


Because when they canceled that meeting, I could see how much time I would have invested into their project before I learned that they couldn’t afford to work with me. I mean, think about it:

  • We would have gone through a discovery meeting (1-2 hours, unpaid)
  • I would have reviewed their needs, their website, analyzed their competitors, and put together a proposal (3-6 hours, unpaid)
  • We would have had a second meeting to review the proposal and decide if we wanted to move forward (1-2 hours, unpaid)

And then and only then I would have learned that we wouldn’t be working together.

In that moment I was so glad I had started our relationship off with the Roadmapping Session.

Wait, so what is a Roadmapping Session?

A Roadmapping Session is a short, strategic, outcome focused meeting between you and your client where you review the intended outcomes for the project, set expectations for what success looks like, and identify any potential barriers to achieving success. At a high level, you’re breaking down the parts of the project and identifying the easiest, most graceful way from where the client currently is to where the client wants to be.

As the first part of every project I work on (and as a separate productized service that I sell), the client and I start off with a 60- to 90-minute meeting where we develop a shared understanding of the client’s goals for the project, define what success looks like to them, and identify the different parts of the project.

There are three major benefits to using Roadmapping Sessions early on in your relationship with customers and potential clients:

  • You reclaim the unpaid time that you’re investing into discovering the client’s needs and writing proposals. And as a bonus you turn that time into paying work.
  • Before you formally start the project, you understand the business goals behind the project and what the client envisions as success.
  • If the client’s expectations are out of scope for the investment they’re willing to make, you can recalibrate their expectations to match their investment.

Do you feel defeated after writing yet another proposal — only to have the client turn it down?

For some consultants, the sales funnel leading into a project can look like this:

  • First contact with the lead
  • Needs Assessment / Qualification
  • Discovery
  • Proposal Writing
  • Client’s Go/No-Go Decision
  • Start Paid Work

That can be a lot of time to invest into a project before you start getting paid. Even if you’re qualifying the client at the start of the project, disclosing your rates, and only moving forward with high value prospects, you can be investing 5, 10, or more hours into a project before you start getting paid.

If that feels like a lot of time, what you can do is, once you make contact with a lead or potential client, position a paid Roadmapping Session as the next part of your sales funnel. In that Roadmapping Session, you’ll work with the client to define their needs, identify their outcomes, and establish a shared understanding of success.

From there, if they choose to work with you, great! But if they decide to work with another provider, you’ve been paid for the time you’ve invested working with them so far.

From the client’s side of the table, when you start off the relationship with a Roadmapping Session, the client is able to begin their relationship with you at a much lower price tag. Instead of starting off with, say, a $10,000 project, a more affordable Roadmapping Session gives the client an opportunity to see you demonstrate your expertise and insight, review the quality of your work, and experience your method of communication. All factors that can lower the risk a client perceives in working with you.

As an end product of the Roadmapping Session, the client receives a report that breaks down exactly what they want to achieve, what success looks like for their business, where they currently are, and the steps that they’ll need to take to move forward with this project.

If either you or the client decides, after the Roadmapping Session, that you aren’t the right right fit for each other, the client will have an asset (the Roadmapping Session Report) that they’ll be able to bring to the table with the next consultant they work with to better define the outcomes they’re targeting with the project.

And as a consultant? Instead of investing hours of unpaid time to get to a Go/No-Go decision with the client, you’re able to start your relationship off with a paid project, reclaiming what would otherwise be unpaid work, and turning qualification, discovery, and proposal writing into a paying engagement.

Yeah, but how exactly do you do this? What do you say? When do you say it?

Once you have an initial phone call with a lead to qualify them as someone you might work with, you’ll want to move them forward to a Roadmapping Session. You can do that by outlining the benefits of the Roadmapping Session for the client, positioning it as the next step in getting to know each other and planning out the project, and pricing it at ‘impulse buy’ levels for the client.

Here’s what that can look like:

It’s great to talk with you and learn more about what you’re looking to accomplish with this project. I can tell you, I’m excited at the thought of us working together.

The next step would be for your team and my team to meet for an initial Roadmapping Session. In that meeting, we’ll review the business goals behind this project, discuss the high-level details of this project, confirm what success looks like to you, and plan out the steps necessary to move through this project.

Once we complete the Roadmapping Session, I’ll deliver a report to your team that reviews our shared understanding of what this project looks like and your vision of success. Additionally, my team will contribute their insight and experience towards this project, identifying the different directions that you can take to achieve your business goals.

The roadmapping session is a 90-minute meeting that would include you, me, and any other decision makers on your side that will be involved in this project.

The charge for a Roadmapping Session is $X. To move forward, here are three potential dates for the Roadmapping Session. Can you let me know which of these dates works best for you?

  • Date 1, Time 1
  • Date 2, Time 2
  • Date 3, Time 3

(If another time works better, just let me know, and I’ll work around your schedule).


At the completion of the Roadmapping Session, you’ll have validated that this is a client that you want to work with, you’ll have a deep insight into the inner workings of the client’s business, and you’ll understand the business goals behind the project and the client’s vision of success.

… What other information would you need to write a winning proposal?

“I don’t want to put all this work into writing a proposal… only to have the client have a completely different set of expectations for the project!”

Outside of reclaiming unpaid time and turning it into paying work, what’s valuable about a Roadmapping Session is getting a high-level view of the client’s needs, expectations, and available energy for the project.

If you’ve ever wondered like this:

“How can I, as a consultant, balance the goals of the project with the client’s perception, budget, and energy/level of dedication to the project?”

Then by incorporating a Roadmapping Session early on in your sales pipeline and/or proposal writing process, you’ll be able to specifically identify the goals of the project, know the client’s available budget, understand the client’s vision of success, and see how much energy they’re willing to dedicate to the project.

“What if the client expects…”

During the Roadmapping Session, you should move the client through a specific series of questions to better understand their project. These should be questions that will let you understand the client’s goals, the business outcomes behind the project, and the client’s definition of success for the project.

By asking these questions in the Roadmapping Session, you’re able to specifically understand the client’s expectations before you write the proposal. If their expectations are off (they want to invest $1 and get back $100), you have the opportunity to recalibrate their expectations to what you’re able to deliver for their budget.

Imagine a client that wants to invest in a website redesign, but not search engine optimization or other traffic generation strategies, and expects to see their website traffic increase by 500% in the first month. Once you uncover this expectation, you can educate the client and recalibrate their expectations, saying something like:

“It’s wonderful that you want to increase your website traffic. That’s awesome! But if that’s the expectation and outcome you’re targeting, perhaps a different type of project would be best to produce that result for your business. That could look like…”

It’s about having, at the start of the project, a clear direction of where you’re going. And to get that clear direction, you’ll need to stop and ask the client for directions:

  • Where does the client want to end up?
  • Where is the client right now?
  • What does success look like for this project? For their business?
  • What would failure look like?

“I’m tempted to try this — but I’m scared about what the client would say…”

Let’s look at the potential outcomes of testing a Roadmapping Session on one lead in your sales pipeline. First off, the lead can either say “Yes!” or “No thanks,” right?

Option A: The Client Says “No thanks”

You propose a roadmapping session and, after considering it, the client decides that the Roadmapping Session isn’t a good fit for them or their business.

In that case, that could mean…

  • The client didn’t see enough value present in the roadmapping session to invest in it for their business.
  • The client isn’t a good fit for your services.

For the first option, one of three things could have happened.

  1. The client might not have seen enough value in the outcomes you listed for the Roadmapping Session and, because of that, decided to not invest.
  2. Alternatively, you might have dropped the ball on communicating the value present in the Roadmapping Session.
  3. Finally, the price might not have been right for the client to ‘impulse buy’ the Roadmapping Session.

You can correct these by increasing the value you present in the Roadmapping Session, better communicating the value that’s already present, or adjusting the price to better fit with your market.

For the second option (“The client isn’t a good fit for your services”), that’s a perfectly fine outcome to come to from proposing a Roadmapping Session.

Some percentage of clients who want to work with you just aren’t the right fit for your business. If the client disqualifies themselves by saying “No” to a Roadmapping Session, instead of investing hours of time in discovery, needs assessment, and proposal writing, you’ve been able to eliminate them from your pipeline earlier on.

Option B: The Client Says “Yes! Let’s do it!”

If the client decides to move forward with the Roadmapping Session, woohoo! That’s great!

You’ve reclaimed unpaid time and turned that time into a paying project!

You and the client get to work together on an initial, small project, building up trust, and validating that the two of you can work well together.

You gain a deep understanding of the client’s needs, business goals, and intended outcomes, that you can then wrap into the proposal for the larger project.

… That’s all sounds pretty good, yeah?

How do I get started with this? What’re the next steps?

First, outline what deliverables make sense with your Roadmapping Session. A Roadmapping Report that highlights the outcomes for the project? Wireframes of the website? User stories? Something else? Depending on your industry, try and figure out what would be most valuable to the client.

Then, choose a price for your Roadmapping Session. It doesn’t matter what price you choose, you can always increase that number down the line. I started out charging $250 for my Roadmapping Sessions and, after three sessions, determined that $500 was a better price for the time I was investing, the markets I was working with, and the information I was delivering.

Finally, pick a lead in your sales pipeline and call them up. Tell them that, as a next step, you recommend moving into a Roadmapping Session, to better understand the business goals behind the project. When you pitch the lead, see how they respond. Write down the objections that they raise and incorporate those into your next pitch.

If they’re a client that’s worth working with, they’ll see value in the Roadmapping Session and decide to move forward.

And if they aren’t the right fit for you, you’ll be able to disqualify them as a lead earlier on in the sales process, saving valuable time that you can invest elsewhere in your business.