I’m tired of non-profits getting burned. At tech conferences, so often the happy hour conversation turns into a tech therapy session. As fun as it is to rant against clunky systems, it frustrates me that the people doing some of the most important work are often the ones most hampered by technology. Knowing what to ask for in redesigns can help ensure that the technology decisions being made meet the immediate needs of the organization, but also have an eye for the future. Often times organizations don’t know what to ask for. So, here is a list of questions to be asking yourself and your developers as you work through a redesign. # Maintainability The maintenance required varies amongst tools. Also, the way a site is built informs the level of effort to maintain it. Make sure that the system is built using best practices and is well documented to ensure people new to the system can easily familiarize themselves. * What maintenance does this system require? * Who will be maintaining the project after launch? * What skillsets do those maintainers need to have? Do they already have those skills or will some professional development be required? * How common are those skillsets in the broader world if you ever change maintainers? * What budget do you have for maintenance moving forward? * How is the site being developed to ensure it is clear to understand for new people to work on? * How is the site documented? * Where will that documentation live? * How will it be updated? # Control Over Data Technology is constantly changing. Your tools will change as well. Working with Drupal, for example, new versions come out necessitating migrations. If the tool is proprietary, learn what is done with your data and how easy it is to migrate that content to another platform. Ask colleagues using that tool to get the real answer. * What control will I have over my data if I use this tool? * Is my data shared with 3rd parties? If so what data and for what purposes? * How will my data be structured to optimize it for eventual migration? # System Flexibility There is oftentimes misunderstanding around what can or cannot be customized with redesigns. Too many times have I heard the story of a site launching that looks beautiful. It matches just what was defined in the design phase. However, when a content author goes in to change out or update a particular piece of content it’s hard coded or the content they want to use breaks the design. It’s important to know what you have control of and what is baked into the site itself. * What can I update and customize? * What are the limits of the content I should use in x feature of the site? # Scaling Similar to the inevitability of migration, it’s ideal to budget for updates over time. Systems can be designed and developed with an eye for the future. Clean, discrete, structured components will allow for new features to be added without incurring technical debt. To move this from the abstract to the concrete, bring up specific features and functionality you might want down the road. How would those features be built in? Are there decisions being made now that could preclude future features from being added? What requirements will future features need to meet in order to work with the system being built? If we wanted to add x feature 3 months from now, how would the current system accommodate this? Don’t see a question you think is essential to a successful redesign? Add it to the comments section. With a constantly shifting terrain, it’s important that the technology we use is flexible, maintainable and scalable. Asking these questions will help make that happen. And who knows, maybe we’ll even see a drop in happy hour therapy sessions.