How We Manage the Project

When we built DropSend, we learned that good project management can be the key between going way over schedule or delivering on time (and budget).
When it comes to project management, here’s the important stuff:
- Milestones
- Project assets like logos, graphics, wireframes, etc
- Messages
- To-dos
In order to manage all this, we swear by Basecamp, a great tool from 37signals. There’s a free version if you only want to manage one project, and then it moves up to $12/mo. (We’re on the $24/mo plan, so we can manage 15 different projects at a time.)
The reason why Basecamp is integral to the process of building this web app is because we have to manage three freelance teams (Jason - Designer, Dave - Developer, BitPusher - Server Team). Doing it all over email just gets too confusing. It’s great to know everything is in one place.

One of my favourite parts of Basecamp is the Milestones area. It really helps me understand where we’re at with the project. The screenshot above shows all our completed milestones. Late Milestones are red, and upcoming ones are yellow. Seeing a bunch of green ones (completed) really makes you feel great and top of things! (And of course, seeing red ones makes you panic!)
One thing we’ve learned is to reply to messages quickly. If your designer or your developer asks you a question (usually over Basecamp) then reply straight away. They may be working on the project in the evenings, or at the weekends (as they are freelance there’s no reason why they should work on it 9 - 5) so this may mean checking e-mail at the weekends. Whatever you do, to keep the work flowing, answering queries fast is the key.
How did you design the UI? A certain program? Or on pencil and paper? I don’t really see a blog entry describing the UI design process?
Comment by Jokester — May 16, 2006 @ 10:09 am
We sketched the UI on paper, and then translated it into PowerPoint. Then we handed the PowerPoint slides over to our developer and he built simple XHTML (with a tiny bit of CSS).
Comment by Ryan Carson — May 16, 2006 @ 12:46 pm
Once you have finished the UI (which it looks like you are close to doing) what will it be like graphically wise, can we expect something nice and light like basecamp?
Comment by James Deer — May 16, 2006 @ 12:56 pm
I am starting to find out what basecamp can do for the development process.
I have been meaning to post it somewhere. . . but the biggest question mark I have is the billing process. I hope that when you get to that step, you share that process.
Comment by Hal! — May 16, 2006 @ 6:40 pm
We found basecamp to be pretty noddy, frankly, when we tried it. It managed to do not-quite-enough for everything we needed. That was six months ago though, so it may have improved.
Frankly, I don’t think you can beat Trac for this stuff, and I’m surprised you aren’t using that instead.
Comment by Doug Winter — May 17, 2006 @ 5:47 am
Probably the most important entity in project management is tasks, you can assign to resources, with a start date, a deadline interdependencies and progress metric.
These are all missing from Basecamp. To-do’s can be assigned to people but that’s all! Not even a due date!
Wondering how you handle your time plan - milestones only ??
Comment by Harry — May 17, 2006 @ 9:34 am
Yup - the simpler, the better! We find that if you try to control a project too much, you spend more time messing around with the schedule, than actually getting stuff done.
Comment by Ryan Carson — May 17, 2006 @ 12:52 pm
Wait and see … :)
Comment by Ryan Carson — May 17, 2006 @ 12:52 pm
Harry,
>>SNIP>
You can assign a to-do to a milestone and of course a milestone has a due date.
Doug,
If you look at the to-do list jpg above you can see Trac is on there as being set up along with Subversion
Comment by Ebstar — May 18, 2006 @ 1:01 pm
Hi,
Congratulations, I liked very much your idea! I really believe on this business model!!!
How about posting the computers, laptops, cameras involved on the project?
Maybe a new section called “The Hardware”
Thanks.
Comment by Rafael Lima — May 19, 2006 @ 3:32 pm
Trac seems to have its place when working on a single project (and the SVN integration is nice), but when working with multiple projects I have been using Mantis. Sure, it’s not the best (and the latest version is considerably slower once you have more bugs in the database) but it gets the job done in a simple way.
There doesn’t seem to be a single ‘killer app’ in this arena - I’m interested in seeing more details about DevShop when it gets closer to launch (2 months ’til beta?)
Comment by Patrick — May 27, 2006 @ 5:16 am
I’m using Basecamp for a few weeks now and I agree with Ryan. Before, I was spending many hours a week just to adapt projects schedules.
I tried different softwares (MS project, a mac app I can’t even remember the name, iCal, …) and Basecamp works for me. It could seem to simple but, actually, you only need milestones and to-dos (general tasks, coding improvements, UI, bug list). Basecamp is also very handy for collaborative work (centralization of messages, e-mail reminders).
However, I can understand you may need more functionnalities (Gantt charts, deadline interdependencies, …) to manage big projects with many resources.
For billing, I’m using a small home-made web app (invoices that must be paid with days of delay, monthly turnover, all invoices from a specific customer).
Comment by Vincent — May 27, 2006 @ 7:44 pm
As a busy freelancer, I found this to be a very useful tool, that I can see becoming more and more important in the future.
Comment by Rob Palmer — September 24, 2006 @ 7:11 am