Freelancers and Consultants: Start Selling Paid “Roadmapping” Discovery Sessions

What Is Proposal Writing Costing You?

When I discovered a quarter of my time each month was spent writing proposals, I was shocked and started to dig a little deeper.

What was our proposal close rate? About one-in-four or 25%. Not so bad.

But then I did the math. If I was sending out 8 proposals in a month, six of them (or 30 hours of work) were wasted effort.


Then I started to think about where we were spending time creating a proposal.

  • Meeting with the prospect
  • Discussing the problem with the prospect
  • Exploring the problem
  • Identifying, evaluating, and refining potential solutions
  • Estimating the price for the project
  • Writing out our recommendations for the project
  • Researching the prospect
  • And then writing the proposal itself

All necessary steps.

As one consultant I spoke with put it:

It seems like clients have this idea that they can just approach us with an idea in their mind for the project and that we’ll be able to just ‘spit out a number.’

But, really, to present a proposal for the project, you need an estimate for the project.

You can’t prepare an estimate without understanding the problem and the different solutions available.

And you can’t understand the problem without meeting with the prospect and exploring and discussing the problem.

All valuable steps. All time consuming steps.

For a typical proposal, it would look something like this:

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

A lot of time invested, but time invested understanding the problem they were experiencing and the best solution for them and their business.

But with only 1 in 4 proposals being accepted, I wanted to understand why people were turning down my proposals — and what prospects I shouldn’t be writing proposals for.

How Many Prospects Should You Not Be Writing Proposals For?

I started looking at our proposal close rate: 25%.

I had tracked the last year’s proposals in a spreadsheet and noted the reason we lost the proposal (I made a habit of always exploring with the prospect why they had decided to go in a different direction rather than work with us).

Looking at the data, I saw patterns start to stand out:

  • Prospects were telling us they didn’t have the budget… after we gave them the proposal
  • Prospects were saying that ‘now isn’t the right time’… after we gave them the proposal
  • Prospects were asking for the moon and the stars… and turning us down saying that the proposal was higher than they expected

Almost 50% of the projects we lost were due to reasons — budget, timeline, expectations — that we should have been able to identify before we invested the time in writing a proposal.

If we were able to identify those ‘bad fit’ prospects before we started writing the proposal, our proposal ‘win’ rate would nearly double from ~25% to more than 50%. And we would get there by writing fewer proposals.

How You Can Identify ‘Bad Fit’ Prospects

I vowed to stop wasting time writing proposals for bad-fit prospects or projects. But how?

What I discovered through research and conversations with other consultants was that this was a problem we all were experiencing:

  • Large amounts of time spent writing proposals
  • Clients sharing project killing information (like budget or timeline) only after we’d delivered the proposal

I didn’t know what the solution should be. I vowed to find out.

How A 37-Year Family Business Taught Me How To Get Paid For Proposal Writing (and stop writing proposals for bad-fit prospects)

And then the air conditioning in my car stopped working.

I know next to nothing about cars. I once put the spare tire on backwards when I got a flat while giving my new girlfriend a ride to work. That was a fun goof-up.

So, because I know next to nothing about cars, I called a professional, just like clients call on us as professionals to help them solve problems.

I called up a car air conditioning repair shop and scheduled an appointment to bring in the car. The conversation went something like this.

Air Conditioning Repair Shop: What’s wrong?

Kai: The air conditioning doesn’t work.

Air: And when did this start?

Kai: I dunno? A few weeks ago, I think?

Air: And when did you last have the air conditioning serviced?

Kai: You’re supposed to have it serviced?

Air: Okay, the next step will be a diagnostic service. It takes 4-hours, so you’ll get your car back this afternoon, and after that we’ll have a report showing what’s working and what’s broken and an estimate for fixing what’s broken. The diagnostic service will be $100.

I was floored — not at the price, but the idea!

I, the customer, had no clue what the source of the problem was. I just knew the solution I needed: Cold air. In my face. On demand.

The Air Conditioning Repair Shop had no clue what the problem was. After all, how could they? I had literally shown up with a car with a not-working air conditioner and shrugged my shoulders when they asked about the problem.

How could they know what the problem was without doing a diagnostic service? How could they know what price to quote me for the repair until they had figured out what the problem was?

Likewise, how could I, as a consultant, know how long a project would take, how much to charge my client, or what problem my client was actually experiencing (and what solution made sense) until I had diagnosed the problem?

I happily paid the service fee — it ended up being a simple repair — and was on my way.

I was now fascinated by the concept of a paid discovery session. I thought it could help fix what I saw as broken about the proposal writing process in freelancing.

The Three Major Wins, For You, By Providing A ‘Discovery Service’

By providing a discovery service, you’re able to:

  • Discover exactly what problem your client is experiencing. Through discovery, you can discover what the problem is and how to solve it best, giving you better information and insight when you write your proposal.
  • Write fewer proposals! Stop writing proposals for clients who don’t have a budget, have a difficult timeline, or don’t have a problem that you can solve
  • Spend less time writing proposals. Because after a discovery session you already understand the problem, you can be much more efficient at writing the proposal.

Eliminate Bad-Fit Clients By Charging For Your Discovery Service

You should charge for your discovery service. Just like the air conditioning repair shop charges for their service.

Charge for the value you’re providing.

By charging for your discovery service, you immediately eliminate clients who don’t have a budget. You immediately surface that objection.

On one project, it was only by telling the client “There’s a $500 fee for the discovery session” that I learned that they had no budget and, in fact, were potentially going out of business next month. (I was happy to not write that proposal!)

Get Paid For Writing Proposals By Offering Paid Discovery Sessions

When you go through a paid discovery session — I like the label ‘roadmapping session’ — you’re compensated for:

  • Meeting with the prospect
  • Discussing the problem with the prospect
  • Exploring the problem
  • Identifying, evaluating, and refining potential solutions
  • Estimating the price for the project
  • Writing out our recommendations for the project
  • Researching the company
  • And then writing the proposal itself

As you should be.

You’re compensated for the time you’re putting into understanding the problem and writing your proposal. Win or lose, you are paid for your time.

Prospects who don’t have the budget, don’t have decision-making power or have already selected another vendor will self-select out, leaving you working with just the best prospects to work with

Because you’ll better understand the problem at hand, you’ll be able to write a better proposal, meaning a higher percentage mom your proposals will be accepted (and sometimes the proposal isn’t even required - you may already know the company, your client for the Roadmapping Session, so well, that you can say “We need to do X. It’ll be $Y., ” and they’ll say “Sounds great, let’s do it.”)

Implementing paid discovery sessions transformed the way I did business.

Gone were the hours researching and writing proposals. Instead, when a prospect contacted me, I could direct them to a roadmapping session as the best place to start.

Now, I was able to write fewer proposals, charge for discovery, spend less time writing proposals, and have more of my proposals accepted.

Presenting “Quick Start Roadmapping Sessions”

But how do you implement Roadmapping Projects for your business?

What goes into a Roadmapping Session? What questions should you ask? What should you charge? What are the deliverables?

How should Roadmapping Projects differ from industry to industry? How would a developer’s Roadmapping Session differ from a copywriter’s or a designer’s?

What're the most important pieces you have to implement? What can you safely ignore?

And how are you supposed to know if it’s even working?

"Btw, your roadmapping sessions material is AWESOME! I read the first chapter and already sold two sessions. :-)" — Customer of Quick Start Roadmapping Sessions

With Quick Start Roadmapping Sessions, you’ll get specific, step-by-step, ‘do this, not that,’ guidance on how to implement paid discovery “roadmapping projects” for your business:

Everything You Need To Know To Run A Roadmapping Session

  • The goals of a roadmapping session and what goes into running and delivering a roadmapping session
  • How to pitch a roadmapping session to a prospect
  • How to execute on a roadmapping meeting (pre-meeting, during the meeting, and after the meeting)
  • How to take the information gathered through the roadmap and translate it into deliverables and a proposal

Selling A Roadmapping Project

  • The best times to present a roadmapping session as an option to a lead (hint: it can be as early as the first conversation)
  • How to transition a client from an initial conversation to a paid roadmapping session
  • How to establish the value of this session in the mind of the prospect
  • Scripts and direction on how to respond to prospect pushback
  • How to position your roadmapping session as the first product that your clients purchase before moving forward
  • How to transition from "Send me a proposal" to "Let's roadmap this."
  • How to pre-sell yourself for the post-roadmapping engagement in the mind of your client
  • A simple sales funnel for presenting prospects with your roadmapping session
  • How to present a roadmapping session as the first step in a longer term relationship
  • How to make roadmapping projects the default option for your prospects
  • How to define the value of a roadmapping session to the client — what they’re getting, how this will reduce future costs, etc.

How To Price And Charge For Your Roadmapping Session

  • The best way to price a roadmapping session (fixed price, custom/variable, time, value…)
  • ‘The rule of 10%’ when pricing your roadmapping projects
  • How to know it’s time to raise the price on your roadmapping session
  • Value-Based Anchoring: What it is — and why you can use it instead of Value Based Pricing 99.9%

Coordinating The Pre-Meeting

  • The exact details you’ll need to know before starting a roadmapping session (Audio Lesson)
  • Pre-roadmapping session, how to best frame the roadmapping process with the client and set expectations
  • Examples of how to sell a Roadmapping Session to a client
  • Answers to common questions and issues clients have about roadmapping
  • The initial pre-meeting questionnaire that you can send out to collect information for the meeting
  • The best thing I added to my roadmapping project this year (a video recording that I share with the client)
  • What to ask clients to prepare (and share with you!) before you meet

Running The Meeting

  • The Standard Operating Procedure that I use to run my Roadmapping Projects (that I print out and have with me for every Roadmapping Project — available as a document for you to edit and a PDF for you to print)
  • The specific questions to ask during the Roadmapping Session to uncover the expensive problems the client is experiencing
  • The best way to stay in control of the conversation during a roadmapping session

Your Roadmapping Deliverables

  • A list of the different deliverables you can optionally include in your roadmapping session (depending on your discipline)
  • The easiest way to identify the most valuable deliverables to include in a roadmapping session
  • Post-roadmapping session, how to best walk the client through the deliverable document to ensure that they are more likely to accept the proposal.
  • The best thing I added to my roadmapping projects this year (a video recording that I share with the client)
  • Creating a project timeline and setting proper expectations around the timeline with the client
  • How to properly set client expectations for the outcome of the roadmapping session

Selling A Project From A Roadmapping Session

  • How to ensure that every deliverable from your roadmapping session sells your other consulting services
  • The three different ways of presenting your deliverables — over email, on a call, or on a video call — and the benefits (and costs) of each
  • A sales script you can use over email, on the phone, or in person to sell the next engagement
  • How to turn your notes from the roadmapping session into a proposal
  • How to pre-sell yourself for the post-roadmapping engagement in the mind of your client

Advanced Strategies

  • Direction on how to ‘systematize’ 99% of the roadmapping session process into something that can be done by another employee that you train
  • An overview of ‘remote’ roadmapping projects: how to run them and what tools to use
  • How much time to budget for a roadmapping session project
  • How to present roadmapping projects as a standalone product (and the advantages and challenges of selling only roadmapping project)
  • Selling a Roadmapping Session if you’ve never sold one before (and don’t have any results to share)
  • What people get wrong trying to do roadmapping project
  • How to help a prospect differentiate a paid roadmapping session from a ‘free’ proposal
  • The exact details you’ll need to know before starting a roadmapping session (Audio Lesson)

What Do People Say About "Quick Start Roadmapping Sessions"?

Here's what customers have to share about their experience with the material.

"Quick Start Roadmapping Sessions helped improve my process to understand what clients really wanted"

Over time I had come across a number of your blog posts and a few podcast episodes. If I did not get those resources I would have never known about the Roadmapping Sessions resource. The timing was also helpful, I had a variety of complex projects to plan out and generally knew about roadmapping.

The book was a fun read, the working session outlines, questions, and examples in the book helped improve methods for working with clients. The roadmapping session provided an option for dealing with clients who want to meet but are not serious about a project or don't fully know what they want or need.

The fact that you had a "quick start" document, the questions, and the working session outlines gave me a quick solution I could start using the next day when I had to meet with a client. Then after taking the time to absorb the book, I was able to further refine and improve methods for understanding client needs.

The quick start documents, the mistakes to avoid document, and the "15-minute guide to 'why' conversations" were all excellent bonuses. Having the working session and other meeting outlines helps provide a scaffold to follow and adapt as needed.

Thank you for making the roadmapping book and resources!

— Brian, B2 Technologies

With “Quick Start Roadmapping Sessions” you’ll receive…

Included with Quick Start Roadmapping Sessions are materials to help you before, during, and after the roadmapping session. You’ll receive:

  • An overview process diagram of the entire roadmapping process, from ‘a lead has contacted me’ through ‘follow-up on delivery of the proposal’
  • Direction on how to quickly get started running and selling roadmapping projects to your clients
  • Advice on the top mistakes to avoid with roadmapping projects
  • Roadmapping Session documents, including a pre-meeting assessment questionnaire, a meeting agenda, and an example post-meeting deliverable document
  • A questionnaire for you to send your client to fill out before the roadmapping session (so you have all the information you need ahead of time)
  • Specific questions to ask during the roadmapping session
  • An example deliverable template to fill out and send after a roadmapping session
  • An example proposal template to fill out and send after a roadmapping session
  • Email swipe files to use before, during, and after the roadmapping session
  • Checklists to follow for the roadmapping session process
  • An over the shoulder look at how I run through the questionnaire template, the deliverable template, and the proposal template

“Quick Start Roadmapping Sessions” is available for $179.

Order 'Quick Start Roadmapping Sessions' for $179

Here’s How To Order “Quick Start Roadmapping Sessions”

First, click the link below.

Then, complete checkout, paying with either a Credit Card or PayPal.

After that, your order will be confirmed.

Quick Start Roadmapping Sessions will be delivered to your inbox within 10-minutes of your order. If it isn't, just reply to your receipt and I'll help track down the issue.

Order 'Quick Start Roadmapping Sessions' for $179

The ‘Smile On Your Face’ Guarantee

Your order is protected by the “Smile On Your Face Guarantee.”

I want you to have a smile on your face.

You can order this product with the confidence of knowing that you’re protected.

If you review the material, practice it, try it, and then decide that this isn’t right for you and your business, just reply to your receipt and say “Kai, I’d like a refund” and you’ll receive a refund in full.

Because I want you to have a smile on your face.

  • You’ll be smiling after reviewing “Quick Start Roadmapping Sessions” because you’ll see exactly how to implement roadmapping projects in your business to get more clients or
  • You’ll be smiling because you were protected by the ‘Smile On Your Face’ guarantee


What’s unique about ‘Quick Start RoadmappingProjects’?

Quick Start Roadmapping Sessions is short and concise. I want to give you useful, actionable information.

Quick Start Roadmapping Sessions is built around giving you the documentation, instruction, and examples you need to start offering roadmapping projects.

You still need to handle selling the roadmapping session and getting the leads.

Quick Start Roadmapping Sessions will give you the information you need to understand how to offer and deliver roadmapping projects for your clients.

Here’s How To Order “Quick Start Roadmapping Sessions”

First, click the “Add To Cart” button below.

Then, complete checkout, paying with either a Credit Card or PayPal.

After that, your order will be confirmed.

Order 'Quick Start Roadmapping Sessions' for $179


Order Quick Start Roadmapping Sessions, a guide on offering paid discovery sessions to your prospects and clients. Order for $179 today!: