I recently had to work on a sizable change in a platform that had not been maintained in years. It took me months to complete it, but I got it done.

Below is a list of points that I have seen overlooked but that I consider important when tackling a sizable project.

  • If it is not exploratory work, then ask for acceptance criteria.
  • If someone tried before, you need to understand why the project failed. You need to have an answer for this before you attempt to do it. Otherwise, you’re simply trying to do the same thing and are expecting a different result. What has changed so that doing the same thing will succeed this time?
  • If there are salvageable parts in the previous attempts of the project, use them and save yourself and the company some time and effort.
  • If the change means offloading responsibility/effort/time/pain onto a lot of people/teams, ask why do it this way? Especially if the current situation is a consequence of decisions made by you or your team, then consider bearing the pain and taking it upon yourself to do the hard work. For an organization, it’s usually better to centralize pain.
  • A project is more than the technical part. Having the technical part down is just half the equation. One key ingredient is having buy-in from all the stakeholders. You won’t have buy-in if you’re causing the stakeholders more pain. However it is easier to have buy-in if you’re making their lives easier.
  • Break the project down into pieces. It’s easier to troubleshoot and fix breakages when the parts are manageable. Be Agile. Start with a Minimum Viable Product if possible. Successfully implementing the changes in chunks builds confidence in the project.
  • Communicate with upper management. Explain if a change (or a piece of it) is low or high risk and its impact so that they can decide if it is appropriate to take on the risk or delay it to another time or at least provide you with the requirements of what they consider a mitigation for the risk. Speak with the person that has the power to define the risk appetite.