You were asked to build a website? Does it seem it will be a larger one? It might be the case it will actually not be a website but a webapp. It might need a team to actually do it. Well, better prepare answers for these couple of questions :-)

Vision and requirements

• Is there a short document explaining why this piece of software should exist and a concise description how it would accomplish that?
• Do we have a place for collecting and prioritizing requirements?
• Are non-functional requirements written somewhere?
• Do we have a schedule or milestones which describes at least roughly what will be done when?

Communication

• Can you think of any expectations that are not described by current requirements?
• Will the customer collaborate with us on a regular basis? ^[1]

Technical environment

• Does anyone from the team have a specific know-how which is necessary / effective to leverage for successful completion of the project?
• Will there be a reasonable return of investment from learning and implementing new technologies? Would it be easier to hire new people with such skills?
• Are there existing systems like CMSes or APIs that needs to be integrated?
• Are there existing URL addresses or domains that needs to be redirected to new ones once the new website will be released?

Infrastructure

• Is there a possibility that currently running systems will be negatively impacted after deploying this new application on target domain?
• How will we host our website or application? Is it possible to change it now or in the future?
• What are the pros and cons of chosen hosting environment over some more traditional choice?

Users

• Do we have some existing analytics data?
• How many users do we expect first day, first month, first year?
• Which browsers and their versions are going to be supported?
• Would the project suffer from missing accessibility features? Is it a subject of regulation?
• Is it any good to provide users with a chatbot and is it worth the effort and possible performance issues?
• Are there any use cases for our website/application to be used without JavaScript enabled?
• Do our users need more language mutations and other internationalization adaptations? Will we need to support a RTL language?
• Will we need to build multiple variants of the software for different users/customers?

Code

• What is/will not be in a version control system? (like secrets, documents, etc.)
• Is there a README.md file which has enough information for any developer to run the application, test it or prepare it for production?
• Does every developer have an automatic way of formatting new code? (in editor on save, precommit hook)
• Is there a process in CI that checks common code style issues for every change? (i.e. linting)
• Is there a process in place that ensures that all code is checked for quality? (code reviews, automated tests and checks)
• Does every developer know when and how a code review is needed and when it is appropriate to merge? ^[2]
• Are there some automated checks for security? ^[3]
• Is there a CI/CD pipeline that deploys every change? (continuous deployment)
• Is there a preview environment for every change and is it practical to have them?
• Do we have know-how when and how to use unit testing, integration testing or end-to-end testing?
• Do we use the right programming language for the job?
• Which framework do we use, what it solves and what problems it does not solve?
• Is there a way to generate some boring boilerplate code?
• Do we have a set of testing data?
• Can we develop against this data set without even running the database?
• Will there be only one version of the software at a time? Or will we have to support multiple versions with following maintenance?

Runtime

• Does the web app handle redeployments of static assets seamlessly?
• How will the web app handle a breaking change in backend APIs while an old version of frontend code is still running on the client side?
• How is the cache on the CDN level invalidated?
• Do we send correct security headers?
• Do we send correct cache headers for HTML, data requests and assets?

SEO

• Does every page have its canonical URL? ^[4]
• Does our canonical URLs end with or without a slash? Do all redirects, sitemap items and links target this canonical URL?
• Do our domain default to www prefix?
• Do we need more control over Google results, and will we use Google search console? Will we use structured data?
• Which website analytics solution will be used? Will we try to project for missing data (blocked by users or usage before consent) and how?
• Do we have a complete sitemap?
• Do we have a robots.txt? Does it contain only necessary records?
• Do we have a page on the site for every frequent search term?
• How are we managing third party scripts? Do we need Google Tag Manager? How much will be the performance influenced by third party scripts?
• Does the application respond with correct response codes? An unknown URL should be 404 etc.

Performance, UX, a11y

• Is it OK to display loading spinners for 10 seconds on a 3G network before displaying the content?
• Will we have to do image preprocessing? Will it be a hosted solution? Do we care about resolutions and formats of those shipped images?
• Is it useful to measure Core web vitals regularly/automatically?
• Will we use progressive enhancement techniques? Does our team have knowledge to do so?
• Are we going to optimize the amount of generated CSS? How?
• Can be the desired set of fonts optimized in order to prevent Flash of unstyled fonts for most users?
• Which level of accessibility will be our target? Do we have someone who understands accessibility on this level?
• Do we have a plan for hallway usability testing? ^[5]

Design

• How does our design process look like? How are responsibilities distributed among designers, developers, marketers, product or UX people?
• Do we need our own design system?
• Which tools and techniques we will use (preprocessing, postprocessing, feature detection, polyfills, CSS structure and layering, scoping, reset, RTL support…)?
• How will we approach responsive design? Mobile or desktop first, strict set of media queries or more fluid techniques, leverage container queries?
• Which set of icons we will use? Will it play well with our framework of choice?
• Do we have a live web with our style guide?

Legal

• Is it necessary to have a cookie consent on the website?
• In case we need a cookie consent would it be beneficial to use a third party solution? Will we use the analytics from that solution for something?
• Do we need to implement something extra in order to comply with privacy laws like GDPR?

Maintenance

• Where will we track tasks and bugs?
• How can our customers report bugs?
• Do we have an automated system for reporting runtime errors?
• How are our production systems backuped? When was the last time we have done a restoration from those backups?
• How often there is a change in some data or source code? For how long will our system handle the increasing frequency of change?
• Which types of changes would our architecture allow easily and which would be hard?
• Do we have a place for writing down maintenance procedures? (E.g. updating dependencies, data schema migration, adding redirects, etc.)
• Who manages credentials and how? Do we need to use an external service for them? Do we need to rotate them?
• Is there a single place (like a URL) which anybody from the team can visit and see important links or other useful information about the project? (I call this a project signpost)
• Do we need to track special events in the system, like conversions?
• Do we have a way to automatically check for links that accidentally targets PAGE NOT FOUND?
• Does our monitoring, logging and tracking solution solve real problems?

Marketing and sales

• How does marketing or sales strategy correspond to a release date of our product?
• Do we focus enough on feedback from users, developers, investors?

The bottom line

This is not an exhaustive list, although I was trying to be complete—based on my experience. BUT keep in mind that it is also critical to maximize the amount of work that does not need to be done! ^[6]

Notes