Quick Start Roadmapping Sessions


Quick Start Roadmapping Sessions covers just the essentials you need to know to start selling, delivering, and running ‘paid discovery sessions’ instead of writing proposals for free.

One day, I get a little fed up.

It was 8 PM at night. I was sitting in my favorite coffee shop, drinking some peppermint tea, and I had a problem.

I had four proposals to write that night. It was Thursday. Each was due Friday.

I wanted (and needed) the projects, so I sat down and started writing the proposals.

Altogether, it took me about 6-hours to get the proposals finished.

I sent the proposals off, caught up on sleep, and the next day woke up with two questions at the top of my mind:

  1. How much time do I spend writing proposals?
  2. How many of my proposals convert into paying projects?

I dug into my data. I looked into my CRM (these days, I use Pipedrive as my CRM). I looked into my Timetracker (Freckle).

And what I found shocked me.

Each month I was spending 10-hours/week writing proposals. That meant one-quarter of my working time each month was spent writing proposals.


Next question: How many of my proposals did I win? I looked at my proposals, I looked at my conversation history, and I looked at (and updated) my CRM.

I won 33% of the proposals I sent out. That meant I was losing 2/3rds of the proposals I sent out. Or, winning 1/3rd of the proposals I sent out.

I did the mental math.

I was spending 26-and-two-thirds hours, each month, writing proposals that got turned down.

If I was billing myself at a rate of $100/hour, I was spending $2,666.66 of my money (and time) to write proposals that got turned down.

What a waste.

Eliminate Bad-Fit Clients By Charging For Your Discovery Service

When you charge for your discovery sessions, you immediately eliminate clients who don’t have a budget. They will immediately raise that objection and you can eliminate them as prospects.

On one project, once I told the client:

“There’s a $500 fee for the discovery session to understand the problem, meet with the members of your team, and write up the proposal with price estimates”

Then I discovered that they had no budget and, in fact, were potentially (90%) going out of business next month.

I was very happy to not have wasted time writing that proposal!

The Three Major Wins You Experience When You Start Charging For A Paid Discovery “Roadmapping Session”

When you start charging for your time by providing a Paid Discovery Session as a service, you experience three amazing benefits:

  1. You’ll get paid for writing proposals. Because creating a proposal is part of the deliverables in a Roadmapping Session, you’ll be paid what you’re worth when you write your proposal.
  2. You’ll know exactly what problem your client is experiencing before you write the proposal. During the discovery session, you can uncover the actual problem the client is experiencing (not just the situation they described to you at first) and write a proposal that solves the problem your client actually needs help with.
  3. You’ll write fewer proposals! When you start charging for your “Roadmapping Sessions,” clients who don’t have a budget, have a difficult timeline, or aren’t really interested in working together will suddenly disappear. That means you’ll stop writing proposals for clients that wouldn’t have been a fit, saving you massive amounts of your time.

Write Fewer, Better, More Targeted Proposals With “Roadmapping Sessions”

When you go through a paid discovery session (“Roadmapping Session”) you’re compensated for the time you invest in:

  • Meeting with the prospect
  • Discussing the problem with the prospect
  • Researching the problem and the situation
  • Identifying, evaluating, and refining potential solutions
  • Estimating a range of prices and scopes of work for the project
  • Researching the company, reviewing their needs, and writing a proposal

You should be compensated for the time that you spend and the value that you provide.

When you’re writing a proposal for a prospect, you’re providing a lot of value to the prospect. You’re giving them recommendations on how to solve their problem. That’s valuable insight and expertise that you are contributing. Why do that for free?

Because you and your prospect (now, client) will be spending the time to better understand the client’s current situation and problem, you’ll be able to write a better, more targeted proposal.

Because you’re writing better proposals for prospects that are a better fit for working with you, you’ll see a higher percentage of your proposals be accepted.

And with Roadmapping Sessions, sometimes the proposal isn’t even required.

Because you’ve already worked with the client on a paid project (the Roadmapping Session), the next step may be as easy as saying “Alright, so we need to do X, Y, and Z. I recommend we tackle X first. It’ll be $Dollars.

And the prospect will say “Sounds great. Let’s do it.”

“Btw, your roadmapping sessions material is AWESOME! I read the first chapter and already sold two sessions. 🙂

An anonymous buyer of Quick Start Roadmapping Sessions

Presenting, 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 Sessions” for your freelancing or consulting business.

“Btw, your roadmapping sessions material is AWESOME! I read the first chapter and already sold two sessions. 🙂” — A buyer of Quick Start Roadmapping Sessions who asked to be anonymous

What should you do to start selling Roadmapping Sessions?

It’s easy to talk at a high level about Roadmapping Sessions, but how do you approach it step-by-step?

  • What should you charge?
  • What are the deliverables?
  • What documents do you need?
  • What questions should you ask?
  • How do you sell a Roadmapping Session to a prospect?
  • What are the common objections to Roadmapping Sessions?
  • How should Roadmapping Sessions differ from industry to industry? (Should a developer’s Roadmapping Session differ from a copywriter’s or a designer’s?)
  • What are the most important pieces of a Roadmapping Session that you have to implement? What can you safely ignore?

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

Get Answers To Your Roadmapping Questions With Quick Start Roadmapping Sessions

Quick Start Roadmapping Sessions is available for $[price_roadmapping]. It has answers to all of your questions on how to implement, sell, and deliver Roadmapping Sessions in your business, as well as a Roadmapping Resource Library full of templates, agendas, and questionnaires for you to use to get started.

Order Quick Start Roadmapping Sessions for $[price_roadmapping]

When you sell a Roadmapping session for $500, $1500, or $5,000+, you’ll have made a very considerable return on your investment. (Yes, it happens — I’ve sold a $10,000 Roadmapping Session and a colleague recently sold a $5,000 Roadmapping Session)

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.  — Brian, B2 Technologies

What You’ll Receive When You Order Quick Start Roadmapping Sessions


The Book: Quick Start Roadmapping Sessions

A step-by-step process to offer, sell, and deliver paid discovery sessions that help you understand what your clients really want. (PDF, ePub, and Mobi). You’ll also receive free updates for life.

Roadmapping Sessions Essentials

Bonus #1: Roadmapping Essentials Guide

You’ll get a ‘do this, not that’ guide to roadmapping sessions, with a ‘cheat sheet’ for all of the included templates. Here’s what one person who bought Quick Start Roadmapping Sessions had to say on the Essentials Guide:

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.  — Brian, B2 Technologies

Kurt Elster Ethercycle Roadmapping Interview

Bonus #2: Kurt Elster on “Roadmapping Sessions at Ethercycle”

Watch this video interview (and read the transcript) with Kurt Elster on how they use Roadmapping Sessions at Ethercycle.

Roadmapping Overview Webinar

Bonus #3: “Roadmapping Overview” Webinar

Watch this 50-minute pre-recorded Webinar (with Q&A) giving you a detailed overview of the Roadmapping process.

Top Roadmapping Mistakes to Avoid

Bonus #4: “Top Roadmapping Mistakes to Avoid” Primer

Use this Advisory Sheet to avoid making common mistakes with your Roadmapping Sessions.

Roadmapping Email Swipe File (1)

Bonus #5: Roadmapping Email Swipe File

Review these 11 emails in PDF form. Then, copy and customize them in your copy of the Google Doc Swipe File. Now you know what to say and how to say it.


Bonus #6: Roadmapping Resource Library

You’ll have everything you need to get started with Roadmapping Sessions with this resource library:

  • Meeting Agenda
  • Report Template
  • Pricing Estimator
  • Sales Page Template
  • Deliverable Planner
  • Standard Operating Procedures


Bonus #7: Video Walkthroughs of Resource Library

You’ll watch ‘over my shoulder’ in these video walkthroughs of the key resources included with Quick Start Roadmapping Sessions

  • Roadmapping Project Report Template
  • Roadmapping Project Questionnaire
  • Roadmapping “Agenda” and “SOP”
  • Roadmapping Project Report Template


Bonus #8: Questionnaire Template with Video Walkthrough

The “Roadmapping Questionnaire” is key to the entire Roadmapping process. You’ll get a Questionnaire Template to use as a jumping off point as well as a swipe file full of recommended questions that you can add in. You’ll also receive a video walkthrough of the Questionnaire, highlighting important features and benefits that this particular Questionnaire Template offers you (and what your own customized Questionnaire should feature).

Order Quick Start Roadmapping Sessions for $[price_roadmapping]

Learn Everything You Need To Know To Run A Roadmapping Session

  • Chapter 1: Read this first! Everything you need to know to get started (and then some) (Page 1)
    • Okay, uh, hand-raise, what is a “Roadmapping Session”? (Page 2)
    • Roadmapping Sessions: They’re for non-technical and technical projects (Page 5)
    • Roadmapping Sessions: What’s in a name? (Page 6)
    • Roadmapping Sessions: They’re a type of “Packaged Service” (Page 7)
    • Why offer Roadmapping Sessions? (Page 7)
    • Putting a “SPIN” on it (Page 9)
    • The importance of asking “Why?” (Page 12)
    • You are probably already doing all of this for your clients already (Page 16)
    • “Fuck you. Pay me.” (Page 16)
    • Roadmapping Sessions help you work with better clients (Page 20)
    • Clients want you to offer a paid discovery process (Page 24)
    • Follow this recipe for your Roadmapping Sessions (Page 26)
    • Let our powers combine… (Page 32)
    • Do these steps next… (Page 33)
    • Getting started with a paid discovery “Roadmapping Session” (Page 34)
    • Why should a client invest in Roadmapping? Discovery reduces risk! (Page 35)
    • How folks typically plan Roadmapping Sessions (Page 37)
    • Recommended Roadmapping Resources (Page 38)
  • Chapter 2: How do you charge for a Roadmapping Session? (Page 40)
    • Pricing Roadmapping Sessions (Page 40)
    • Two Pricing Methods for Roadmapping Sessions (Page 41)
    • How you know it’s time to raise the price on your Roadmapping Session service offering (Page 47)
    • What about value-based pricing? (Page 48)
  • Chapter 3: How do you sell a roadmapping project? (Page 50)
    • How do you transition a client from the ‘initial conversation’ to the paid roadmapping session? (Page 52)
    • How do you establish the value of a roadmapping session in the mind of your prospect? (Page 54)
    • Let’s talk about prices! (Page 63)
    • “TL;DR Risk For Me” (Page 67)
    • How to position your Roadmapping Session as the first service that your clients purchase from you to start moving forward (Page 69)
    • How to transition from “Send me a proposal” to “Let’s Roadmap this” (Page 71)
    • How to pre-sell yourself for the post-Roadmapping engagement in the mind of your client (Page 74)
    • A simple sales funnel for presenting prospects with your Roadmapping Session (Page 75)
    • How to make Roadmapping Sessions the default option for all your prospects (Page 76)
    • “What’s a Sales Page I can use to sell Roadmapping Sessions?” (Page 77)
  • Chapter 4: What do you do once the client has paid? (Page 79)
    • The Pre-Meeting Phase (Page 80)
    • Roadmapping Standard Operating Procedure (Page 81)
    • The other phases of a roadmapping project (Page 81)
    • How should you frame your ‘Roadmapping Process’ in the mind of your client? (Page 82)
    • What if the client has a question you don’t know the answer to? (Page 83)
    • What if the client asks “Why do we need a Roadmapping Session?” (Page 84)
    • Setting expectations about the outcome of the Roadmapping Session (Page 86)
    • The Questionnaire (Page 87)
    • What to ask clients to prepare (and share with you) before the first meeting (Page 87)
    • Reviewing The Questionnaire (Page 88)
    • Preparing For Your Meeting (Page 89)
  • Chapter 5: The Questionnaire (Page 90)
    • What do you include in a pre-meeting questionnaire? (Page 93)
    • Example Roadmapping Questionnaire (Page 94)
    • Filling out your “Customized Questions” (Page 96)
    • Frequently Asked Question (Page 97)
    • What if you need to deliver a ‘slimmed down’ version of The Questionnaire? (Page 102)
  • Chapter 6: The Working Session (Page 103)
    • Working Session Overview (Page 104)
    • Your Roadmapping Meeting Agenda (Page 105)
    • Running a Working Session (Page 107)
    • Controlling the conversation (Page 108)
  • Chapter 7: Synthesis (Page 110)
    • Reviewing information (Page 110)
    • What’s the problem? (Page 111)
    • What’s the solution? (Page 114)
    • What’s the plan? (Page 116)
    • Determining the best plan (Page 120)
  • Chapter 8: What Deliverables should you include? (Page 121)
    • What kinds of deliverables are there? (Page 121)
    • The Report (Page 123)
    • What deliverables do you need? (Page 125)
    • What deliverables should you include in your roadmapping project? (Page 129)
    • How can you know the most valuable deliverables to include? (Page 129)
    • How should you walk your client through the deliverables? (Page 131)
    • Should you include a proposal with your deliverables? (Page 131)
  • Chapter 9: How do you translate all this into a proposal? (Page 133)
    • Discovery helps you write better proposals (Page 135)
    • Translating the Roadmapping Session into a proposal (Page 137)
    • What questions should you ask to learn about the most important things from the client? (Page 141)
  • Chapter 10: How do you deliver this to a client? (Page 142)
    • The delivery (Page 142)
    • The deliverable meeting (Page 143)
    • Identifying hidden stakeholders (Page 144)
    • The proposal delivery (Page 145)
    • The meeting to review the proposal (Page 146)
    • Going for the sale (Page 147)
    • Follow-up (Page 149)
  • Chapter 11: What should you do after the Roadmapping Session? (Page 152)
    • Follow-up on the Roadmapping Session (Page 152)
    • Send them a proposal (Page 153)
    • Ask them for a testimonial (Page 153)
    • Ask them for a referral (Page 154)
    • Add the client to your Sales CRM for Follow-up (Page 154)
    • Publish your testimonial (Page 155)
    • Publish your case study (Page 155)
    • Refine your Roadmapping Project (Page 156)
  • Chapter 12: Advanced Roadmapping Session Tips and Tricks (Page 159)
    • Systematizing your Roadmapping Session process (Page 159)
    • Running remote Roadmapping Sessions (Page 161)
    • “Can you sell ‘Roadmapping’ as a standalone product?” (Page 163)
    • Thank You (Page 167)

Order Quick Start Roadmapping Sessions for $[price_roadmapping]

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


“Btw, your roadmapping sessions material is AWESOME! I read the first chapter and already sold two sessions. :-)” — A buyer of Quick Start Roadmapping Sessions who asked to be anonymous

With Quick Start Roadmapping Sessions you’ll receive…

Included with Quick Start Roadmapping Sessions are materials to help you before, during, and after your Roadmapping Session.

One of the major benefits that buyers have repeatedly called out is that they were able to buy Quick Start Roadmapping Sessions and start selling (and delivering!) on their Roadmapping Sessions within a day (though I personally would say ‘a few days’ is a realistic expectation. You do you).

When you order, you’ll receive:

  • Checklists to follow for the roadmapping session process
  • Specific questions to ask during the roadmapping session
  • Advice on the top mistakes to avoid with roadmapping projects
  • Email swipe files to use before, during, and after the roadmapping session
  • An example proposal template to fill out and send after a roadmapping session
  • An example deliverable template to fill out and send after a roadmapping session
  • Direction on how to quickly get started running and selling roadmapping projects to your clients
  • A questionnaire for you to send your client to fill out before the roadmapping session (so you can start learning about their situation before you meet)
  • An overview of the entire roadmapping process, from “A lead has contacted me” through “What to say when you follow-up after delivering your proposal”

Quick Start Roadmapping Sessions is a hybrid product, with a book, supporting video, templates, and a resource library.

Order Quick Start Roadmapping Sessions for $[price_roadmapping]

“What’s unique about Quick Start Roadmapping Sessions?”

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 Sessions, now, for your clients.

You still need to do the marketing and selling of your Roadmapping Sessions to your prospects. This book will give you the tools, templates, guidance, and instruction that you need to get started.

After reading Quick Start Roadmapping Sessions, you’ll know what steps to take to offer and deliver Roadmapping Sessions in your business.

“What makes you qualified to tell me about my business?”

  • I’ve worked as an independent consultant for 10+ years
  • I’ve given talks at sold-out conferences on two continents on the topic of consulting
  • I’m frequently interviewed for my thoughts on what it takes to grow a successful consulting business
  • I’ve written 4+ books and created multiple videos courses on marketing for freelancers and consultants
  • I write a daily column for consultants with actionable advice on how to build market habits to fill your pipeline with leads
  • I’ve coached over 400 freelancers and consultants 1-on-1 and in group settings on how to get more leads for their business
  • I hosted Make Money Online (http://makemoneyonline.exposed) a 100+ episode podcast about running an independent consulting business

“Wow, $129 for a book! That’s robbery!”

Is this material “worth” $129?

No — if you think of it as “paper and ink.” (Or… digital paper and ink).

But that’s not what I’m selling.

What I am selling is information.

When you purchase this, you’ll receive actionable, specific, targeted information on what to do to implement Roadmapping Sessions in your business today.

More information than I give away when I’m paid $1,000 as a guest speaker.

More advice than if we jumped on a 1-hour phone call for $300 (https://kaidavis.com/call/)

“Are ‘Roadmapping Sessions’ effective? Does this work 100% of the time?”

Roadmapping Sessions are a very effective way to:

  • Get compensated for your time
  • Work on an initial small project with a client
  • Eliminate ‘bad-fit’ clients earlier in your process
  • Avoid writing proposals for clients without a budget
  • Develop a rapport and relationship with the client, through a small initial project
  • You get out what you put in. You still have to do the work. I’ve included everything I could think of to help you on your journey. It’s up to you to move forward.

“Is this a magic bullet? Will my business be transformed?”

There are no magic bullets.

Roadmapping Sessions are a wonderful way to better understand a client’s needs instead of writing a proposal, and also ensure that you are compensated for your time.

Roadmapping isn’t a magic bullet that’ll print money for you. It is an effective way to get paid for your discovery process — and, while you’re at it, formalize your discovery process into something that will impress your clients and help you get the information you need.

“Why is this so short? Most business books are around 80,000 words.”

Quick Start Roadmapping Sessions is focused on the ’80/20′ core information that you need to know to feel confident and comfortable implementing Roadmapping Sessions in your business.

Let’s be honest: when was the last time you sat down and read a Very Long Business Book cover to cover?

What I’ve done with Quick Start Roadmapping Sessions is give you the ‘80/20’ on what you need to know to get started selling and delivering Roadmapping Sessions.

My “Smile On Your Face” Refund Guarantee

I want you to have a smile on your face.

If you are less than 100% satisfied with your purchase, just email me and say so.

Once I hear from you, I will immediately click “Refund” and return 100% of your money to you, no questions asked.

“Who is this not right for?”

This is not right for you if:

  • You’re looking for a ‘done for you’ option
  • You’ve never sold your services before as a freelancer
  • You’re not comfortable having a ‘business’ or ‘why are we doing this project?’ focused conversation with your client
  • You’re not comfortable telling people “The first step to working together is a paid engagement. It’s $X. Would you like to move forward?”

Order Quick Start Roadmapping Sessions Today

Quick Start Roadmapping Sessions is available for $[price_roadmapping].

If the email template for how to tell a client you start with a paid roadmapping session alone saves you two hours in a year that you’d otherwise waste writing a proposal and you charge $100/hour, you’ll have made back the cost of Quick Start Roadmapping Sessions, right there.

And if you go as far as selling a Roadmapping session for $500, $1500, or $5,000+, then you’ll have made a very considerable return on your investment.

Order Quick Start Roadmapping Sessions for $[price_roadmapping]

Risk-Free Money Back Guarantee

When you buy Quick Start Roadmapping Sessions, you’re protected by my risk-free money back guarantee. If you aren’t satisfied with the product, just hit ‘reply’ to your purchase receipt and let me know. I’ll refund you 100% of your money. (I may ask a few questions to learn how I could improve the product).

Kai Davis

Have a burning question? Looking for some advice? Think of something that you’d love to see included with this product?

Email me directly at kai@kaidavis.com.




— Kai Davis

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