- When your source code repository is a chaos and you spend a lot of time finding things.
- When you don't know where to find the documentation of the project, or it is splitted among multiple places.
- When each time you're given a task, you spend hours reading documentation to understand what do you actually have to do.
- When the application is so messy you can't debug properly.
- When you ignore application logs because they don't properly log relevant information (or it is overwriten in case of cascading errors with the last one).
- When crucial information lies not on documents but on people and you have to ask and ask and ask again them.
- When you see something poorly coded in a few places (including newly created ones) and when you ask why it is done this way the answer is "because we've always done it this way".
- When deploying a web application relies on just one person and you don't even have IIS installed on your machine. *
And a more important signal of the problem is when multiple people end doing those "fixes" without previous agreement. Then you can almost be 100% sure it is a either a problem or a bad habit.
Life is not easy for us the developers. Please, don't make it harder by not listening to our better organization suggestions. After all, we're the ones that will be using all the resources most of the time.
* ASP.NET Web Development Server does a great job, but in some scenarios like for example using additional MIME types or having weird Web Services, it just can't replace IIS.