diff --git a/content/roadmaps/111-design-system/content/107-tooling/100-development/100-component-catalog.md b/content/roadmaps/111-design-system/content/107-tooling/100-development/100-component-catalog.md
index 4ef9752fbba3..6450a95a58bd 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/100-development/100-component-catalog.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/100-development/100-component-catalog.md
@@ -1 +1,3 @@
-# Component catalog
\ No newline at end of file
+# Component Catalog
+
+Isolate your UI components’ environment outside of your product codebase to make sure they’re not dependent on any global dependencies and can be easily reused.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/100-development/101-documentation.md b/content/roadmaps/111-design-system/content/107-tooling/100-development/101-documentation.md
index 7d8b3af51547..c4befcff68a0 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/100-development/101-documentation.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/100-development/101-documentation.md
@@ -1 +1,3 @@
-# Documentation
\ No newline at end of file
+# Documentation
+
+Having your code documented is key to driving adoption and reducing the load on the contributors.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/100-development/102-code-style.md b/content/roadmaps/111-design-system/content/107-tooling/100-development/102-code-style.md
index c2753d4c62a5..1d5a8d627615 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/100-development/102-code-style.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/100-development/102-code-style.md
@@ -1 +1,3 @@
-# Code style
\ No newline at end of file
+# Code Style
+
+Having a defined code style helps align the way code’s written in the system and increases development velocity. It should be automated with the tools provided for each platform.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/100-development/103-unit-testing.md b/content/roadmaps/111-design-system/content/107-tooling/100-development/103-unit-testing.md
index 94ee45331df1..77bbb64bf7d9 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/100-development/103-unit-testing.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/100-development/103-unit-testing.md
@@ -1 +1,3 @@
-# Unit testing
\ No newline at end of file
+# Unit Testing
+
+Every part of the design system should be covered with unit tests. Once your system’s adopted, any change in the isolated environment may affect how the product works.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/100-development/104-accessibility-testing.md b/content/roadmaps/111-design-system/content/107-tooling/100-development/104-accessibility-testing.md
index 8e93fac42b54..5ec7e1447c4f 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/100-development/104-accessibility-testing.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/100-development/104-accessibility-testing.md
@@ -1 +1,3 @@
-# Accessibility testing
\ No newline at end of file
+# Accessibility Testing
+
+Design systems should cover accessibility as much as possible. Making this automatic reduces the risk of inaccessible components or user flows in the product.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/100-development/105-semantic-versioning.md b/content/roadmaps/111-design-system/content/107-tooling/100-development/105-semantic-versioning.md
index 6b7b034763dc..855d3d37506d 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/100-development/105-semantic-versioning.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/100-development/105-semantic-versioning.md
@@ -1 +1,3 @@
-# Semantic versioning
\ No newline at end of file
+# Semantic Versioning
+
+Version your code with semantic versioning that dictates how version numbers are assigned and incremented.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/100-development/106-release-strategy.md b/content/roadmaps/111-design-system/content/107-tooling/100-development/106-release-strategy.md
index 6b89c428e5c8..96af665031b0 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/100-development/106-release-strategy.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/100-development/106-release-strategy.md
@@ -1 +1,3 @@
-# Release strategy
\ No newline at end of file
+# Release Strategy
+
+Design system releases should be automated and ideally use scripts ran locally or in remote CI pipelines to prevent broken releases.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/100-development/107-commit-guidelines.md b/content/roadmaps/111-design-system/content/107-tooling/100-development/107-commit-guidelines.md
index 641eed230c43..ddf8169bb501 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/100-development/107-commit-guidelines.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/100-development/107-commit-guidelines.md
@@ -1 +1,3 @@
-# Commit guidelines
\ No newline at end of file
+# Commit Guidelines
+
+Automate the generation of your changelog by adopting a commit message guidelines that categorise and define the changes being made.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/100-development/108-pr-templates.md b/content/roadmaps/111-design-system/content/107-tooling/100-development/108-pr-templates.md
index c6498f60ff87..ffe21acff591 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/100-development/108-pr-templates.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/100-development/108-pr-templates.md
@@ -1 +1,3 @@
-# Pr templates
\ No newline at end of file
+# Pull Request Templates
+
+Create pull request templates that outline the change being proposed to facilitate productive discussions.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/100-development/109-contribution-guidelines.md b/content/roadmaps/111-design-system/content/107-tooling/100-development/109-contribution-guidelines.md
index 1ac60054df4d..56612e5e4bee 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/100-development/109-contribution-guidelines.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/100-development/109-contribution-guidelines.md
@@ -1 +1,3 @@
-# Contribution guidelines
\ No newline at end of file
+# Contribution Guidelines
+
+Define the process of contributing to the code of the design system. Document everything in a discoverable place to make it easier for everyone to contribute.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/100-development/readme.md b/content/roadmaps/111-design-system/content/107-tooling/100-development/readme.md
index 90c64e52f95d..78864b924d51 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/100-development/readme.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/100-development/readme.md
@@ -1 +1,3 @@
-# Development
\ No newline at end of file
+# Development
+
+One of the main challenges in developing a design system isn’t building the components. It’s making your code stable, easy to read and contribute to.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/101-design/100-design-editor.md b/content/roadmaps/111-design-system/content/107-tooling/101-design/100-design-editor.md
index 9b2ee69ffa6d..1c8a45fc32f6 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/101-design/100-design-editor.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/101-design/100-design-editor.md
@@ -1 +1,3 @@
-# Design editor
\ No newline at end of file
+# Design Editor
+
+There are many design editors available in the market today with the most popular names being Sketch, Figma and Adobe XD. If you're unsure which route to go down it's often best to speak with your team.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/101-design/101-plugins.md b/content/roadmaps/111-design-system/content/107-tooling/101-design/101-plugins.md
index f39a3a0c3855..b3acf15523bb 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/101-design/101-plugins.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/101-design/101-plugins.md
@@ -1 +1,3 @@
-# Plugins
\ No newline at end of file
+# Plugins
+
+Most popular Design Editors (Sketch and Figma, especially) come with third-party plugin support. Whilst it's best to use the editors in-built tools for laying out your components, plugins can bring in a range of useful data to populate them.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/101-design/102-version-control.md b/content/roadmaps/111-design-system/content/107-tooling/101-design/102-version-control.md
index 27f303ff054f..f6979a47d1a1 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/101-design/102-version-control.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/101-design/102-version-control.md
@@ -1 +1,3 @@
-# Version control
\ No newline at end of file
+# Version Control
+
+Having your design versioned with semantic versioning will allow you to easily align design with development, roll back faulty changes and release changes in code and design at the same time.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/101-design/103-contribution-guidelines.md b/content/roadmaps/111-design-system/content/107-tooling/101-design/103-contribution-guidelines.md
index 1ac60054df4d..a7b9d58334b5 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/101-design/103-contribution-guidelines.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/101-design/103-contribution-guidelines.md
@@ -1 +1,3 @@
-# Contribution guidelines
\ No newline at end of file
+# Contribution Guidelines
+
+Define the process of contributing to the UI and UX of the design system and document it in a discoverable place to make it easier for everyone to contribute.
diff --git a/content/roadmaps/111-design-system/content/107-tooling/101-design/readme.md b/content/roadmaps/111-design-system/content/107-tooling/101-design/readme.md
index f936956a2eb5..9bcdf2b0a5f6 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/101-design/readme.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/101-design/readme.md
@@ -1 +1,4 @@
-# Design
\ No newline at end of file
+# Design
+
+The UI and UX in a design system need to be tied to development as much as possible. The tools in this checklist should help designers and developers work better together.
+
diff --git a/content/roadmaps/111-design-system/content/107-tooling/readme.md b/content/roadmaps/111-design-system/content/107-tooling/readme.md
index 689c85d4f21b..9a7ec64db05b 100644
--- a/content/roadmaps/111-design-system/content/107-tooling/readme.md
+++ b/content/roadmaps/111-design-system/content/107-tooling/readme.md
@@ -1 +1,4 @@
-# Tooling
\ No newline at end of file
+# Tooling
+
+To make things efficient for anyone using your design system, make tooling essential. Find the workflows where you can integrate things with the tools people use. This helps organically spread your design system and make it crucial to people’s daily work.
+