Cheat Sheet: Project Kick-Off

My cheat sheet for kicking off new projects

Photo by Jonas Denil on Unsplash


I regularly spot the same things in projects that make me think “I wish we’d considered this earlier”.

This post is a checklist for myself to think about when kicking off a new project. Some items apply when joining an existing project too.

It’s currently in draft format and needs reorganising, but I want to get it out there.

I plan to keep this post updated as I think of new things to add or change over time.

Pipelines and CI/CD

  • Static code analysis in pipelines
    • Linters?
    • Sonarqube?
  • Automated accessibility testing
  • Can you go to prod on day one?
  • Can you avoid branch-based CI and focus on trunk-based development?
  • If you absolutely must generate release notes, can you automate this in your pipelines?
  • Your pipelines should fail if they find dependencies with known issues (using something like npm audit)

Monitoring, Logging, Observability and Alerting

  • How will you know when something has gone wrong?
  • Can you include both correlation IDs and customer-journey IDs in your logs from day 1?
  • Do you need Google Analytics on your frontend?
  • Is Instana something you should look at using?

Other stuff

  • Feature flags/toggles - will they be easy to add if you need them? Why not just add this capability from day 1?
  • Is your team skilled at outside-in TDD? If not, can you coach them during the project?
  • Does the problem you are trying to solve actually need software written?
    • Is there an open source tool that already solves the problem at hand?
    • What’s the smallest, leanest MVP you can get away with?
  • Can you set the codebase up such that a developer can clone it, build it, and run the tests locally with little to no effort?


  • Remember that your job is to write software that is easy to change and maintain.
  • Clean Architecture - is this an option?
    • Can you get away with a hexagonal monolith?
  • Does your architecture allow for blue/green or canary deployments?
  • How much infrastructure work can you outsource to existing solutions, or at least write as code?
    • Serverless framework - will this work for you?
  • Where are the high-level boundaries in your domain?
  • What are your obvious initial integration points?
  • Are your VPCs, and all related network and security boundaries, laid out in a logical fashion and, if needed, easy to change later?
  • If you are using a cloud provider like AWS, do they have a simple, recommended infrastructure pattern you can follow?
  • Do you need to ship data to a data warehouse?
  • Do you need different read and write models?
  • Do you need to think about CQRS?
  • Do you really need a document DB? Or is this software inherently mapping entities that are more relational?
  • Can you automate dependency updates somehow?
    • Dependabot?
    • Renovate?


  • Can you achieve your goals using boring technology?
  • Can you choose one language that will work in all areas of your code?
  • Is your chosen language/stack/framework etc. a popular and proven one that you can easily hire for later on?

Team shape

  • How close can you get to your customer?
  • What’s the smallest, leanest team you can get away with?
  • Can you get a product owner and a few real users on your team?
    • How do you know what your users actually want and need?


  • Do you need fancy processes, scaling frameworks, Scrum masters etc.?
    • Or is your team disciplined enough to take a simple Kanban approach without needing “management”?

Main sources for this post

Scott Edwards
Engineering Manager / Lead Software Engineer

Lead software engineer, engineering manager, and beginner guitarist. I also have a strong interest in long-term investing.