My IT career started out being a techie.  But over time it morphed into being a project manager.  It turned into studying business process, communication, and psyschology instead of just code, design, and configurations.

In this time I have learned that there are signs that things are going wrong in a software project.  The problem is that on the surface they seem very encouraging when they are exactly the opposite.
  1. No red flags.  You start looking over the moving pieces that are working together on a project and you don’t see any signs of things going wrong.  That’s not because there aren’t reasons to be concerned. It just means you don’t have the visibility you need.  It is the natural state of man to erode collaborative efforts by negligence or by will.  Every project I’ve been on has required time spent on addressing red flags so if you don’t see them you aren’t paying attention in the right areas.
  2. Words of optimism.  I was at a Microsoft TechEd conference attending a talk on software project management.  The speaker said that in project management “hope” was a derogatory four-letter word.  Touche.  It’s been my experience that people respond to uncertainty with optimism.  They “hope” to be done on time, “God willing” this or that will get accomplished, “probably” they’ll get what’s needed.  As a PM, I want to know something is going to be done, not wistfully dream of it. If people are speaking with optimism, time to dig in and find the uncertainty that underlies it.
  3. No objections.  You propose something and everyone in the room nods their heads in agreement.  Don’t think that no news is good news because with software projects it most certainly is not.  No news is no information, so bad news really. What are the odds that you can propose something before getting feedback and it just nailed it from everyone’s perpective with no changes needed at all? If people aren’t talking they aren’t paying attention or they’ve become detached. Get everyone’s head in the game.
  4. Deadlines are set with ease.  You ask for estimates and they have them for you johnny on the spot.  The quicker a person promises a delivery date the less time he or she spent thinking about the actual work involved.  Some things are pretty routine and ETAs can come on demand, but when you are doing something new it’s best to give people time to digest and then give an estimate later.  And don’t build out your schedule on the first “guestimate” unless you like a house of cards.
I don’t mean to be cynical.  Optimism has it’s place when it’s in the form of belief that progress will be made-not hoping good fortune will see you through.  And it is true that sometimes I’ve been looking for problems that didn’t exist because people really were ok with whatever was proposed.  But that’s minor compared to opposite.  Listen, if you have project where there’s no red flags, there are no objections, estimates were easy, and everybody is speaking positively, you either have a trainwreck or a 1st grade arts and crafts project. Point is, you need to believe that failure is possible in order to make sure you succeed.