Evaluating Different Über-Simple Project Management Solutions

In my ever-evolving attempt to bring the processes of project management and good process, which I learned working at bit software companies like Autodesk, to the day-to-day realities of producing websites for smaller, individual clients, I am going to evaluate a handful of possible tools to help me and my clients communicate.

In my ever-evolving attempt to bring the processes of project management and good process, which I learned working at bit software companies like Autodesk, to the day-to-day realities of producing websites for smaller, individual clients, I am going to evaluate a handful of possible tools to help me and my clients communicate.
Some of the problems I am trying to solve:
  • I cannot always find client’s emails easily
  • I am not always sure if client received my email
  • Client is not always sure if I received their email
  • Client makes comments on site in email, sometimes in vague terms, and the tracking of these fixes becomes a headache
  • Client provides website copy and images via email—often having to manage large files through email, and with no version control
  • Client does not have a sense of what “sign-off means”—as many times and ways as possible, I want to reiterate the sign-off concept
  • Client is not aware of their own deliverables as “drop-dead” dates, and may generally be unfamiliar with the idea of sticking to deliverable dates (me or them), as being a top priority
So turning that all around to a list of things I want (what a concept! ;-), I am looking for:
  • A system that unifies all project communications simply and easily in one place.
  • A system that allows clients to easily upload all project files, with clear naming conventions, and clear, automatic versioning on all files—ideally, in folders or some other structure that is coherent with the site map—therefore, it might allow me to set up this structure before the client uploaded the files. In an ideal world, this system would always have exactly one of every file in question—because what often happens is, the client will upload version after version of certain files, and then I have to be the one to sort out which is the latest version of any file. Instead, the system and the process should make it unavoidable to have the latest version.
  • It must parrot all communications—file uploads, status changes, messages, etc.—to email automatically. This is because email must become the fallback system that alerts the client of any changes. At the same time, the system must strongly encourage the client to use it. For example, some systems will say “you have a new message,” and then provide an email that allows the recipient to go and see the message. (Other systems, like ThreadBox, allow you to fully utilize email, if that’s what you’re going to do, but still automatically record it all in the system.)
  • If possible, it would be great if the system reiterated the idea of project phases, and that we are currently in Phase X—but I am not sure if this should really be a system’s job).
  • A system that allows clients (or me) to enter “defects”, a-la a traditional defect tracking system.
    • But this system needs to be very, very simple, otherwise, they will not use it. (In addition, I have become spoiled, and to not wish to work with a clunky old “web 1.0 system”.)
    • Ideally, this system would have enough control over statuses that I could give the client a “reporter”-level account, where they could report issues, but I would have to approve them, simply because they might duplicate an issue (clients often do not have the perspective to see that a pattern repeating on seven different pages is actually the same issue appearing seven different times!).
    • I could then “approve” the issues, and they would get email on this, or change the status, or break them out into separate smaller issues. Then, when I fixed the issues, they would get email notification about that.
Ideally, the system(s) would also:
  • Send reminder emails to the client on any milestones they had—as well as ones I have—several days before the milestone was due. (I am not sure if it makes sense to expose an entire project management system, in the more complex sense, to the client—with exhaustive lists of tasks. But on the other hand, I would love to have a system that highlighted the basic  milestones—with task ownership on each milestone.)
I am seeing that the more I can do to highlight the idea of project phases, of serious deadlines, and of their (and my) deliverables, the better. What I am starting to realize is, as long as I am working with clients who are not already part of a big corporate development or marketing department, I may be dealing with people who have never thought about this kind of process.
Therefore, I am dealing with a situation of needing to educate about the process, simultaneous with implementing the process. Therefore it must be:
  • Clear and Simple (as immediately gettable as possible)
  • Automatic (email notifications send automatically, for example)
  • Consistent (reiterated throughout all contact with me, and all my documented procedures, practices, etc.)
  • Unavoidable (as in, This is the way I work. This will ensure your success, and our success together. If you are not willing to work this way, this will not be a good fit. This type of process allows me to keep costs down, and speed the entire process of development to a successful outcome.)
The systems I will need:
  • A messaging system
  • A file management system
  • A defect tracking system

It would be nice if they were all together in one thing, but I’m not sure that is required.

Next: My Solution

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Chris