Use this ‘trick’ to learn what keeps your clients up at night

by Kai Davis | Last Updated: October 28, 2020
Use this ‘trick’ to learn what keeps your clients up at night

When you start selling roadmapping — paid discovery — as a productized service, you’re defining a process that allows you to dive into your client’s brain and learn what their needs, worries, fears, and problems are before you write your proposal or prepare a quote.

When you run a roadmapping discovery session for a client, you’re providing structure for the client. You’re saying

It’s vital for me to understand what’s happening, what the problem is, and what outcome you’re looking for. To make sure I know that — before I write a proposal — we need to start with this discovery session.

When you go through a roadmap, you’re taking the time with your clients to pause, have them reflect on their current situation, and share what’s keeping them up at night.

Maybe your client is coming to you for a refresh on their brand and a new logo.

But is the need for a logo keeping them up at night? Or is it something deeper and more impactful?

Whatever is keeping them up at night, when you host a discovery session with your client, you’re able to dive in and better understand the problem from their side of the table.

At the heart of a roadmapping session is a Roadmapping Questionnaire. Your roadmapping questionnaire is a document you can send to your client ahead of your first meeting for them to fill out with their answers.

I love the roadmapping questionnaire because it helps you understand the immediate problem they’re facing, where the unknowns are, and the impact that the problem is having on their business.

You can then review their answers, prepare a laser-focused meeting agenda, and dive in to map out how to fix the problem at hand.

When you understand:

The problem they’re facing

Why fixing this problem matters

The impact that the problem is having on their business

You understand where the value is for your client in working together. And that, my friend, lets you write a powerful proposal and price yourself with accuracy and confidence.

The Roadmapping Questionnaire Template included with Quick Start Roadmapping ( is pre-written so you can get started using it immediately.

And with over a dozen questions in the template (and dozes of additional questions in the included swipe file), you’ll be able to customize your Roadmapping Questionnaire to work well with your clients. (Included are questions on qualifying the client and their project, establishing the budget, and understanding objectives.)

Learn how to sell, run, and deliver Roadmapping Sessions in Quick Start Roadmapping:



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