I wrote a post a few days ago about how seemingly difficult projects are actually easier to achieve than projects labeled as easy.
In this post, I was more talking about a global approach to projects, projects here being any kind of thing you might attempt on your life.
Let's focus today on how this applies to management
I have consistently remarked that the projects that were labeled as hard were, in general, successful.
Easy projects however have the nasty habit of turning ugly at some point, and if not utterly failing, well, didn't succeed as well as they were supposed to. For example, every first release of a website tended to be a success (which doesn't mean that their birth wasn't painful), but every second iteration (which was supposed not to be as painful, since we knew what we were doing) birthed in equal, if not worst, pain.
Hard projects: top dedication
The main reason that I can think of is that when you know it's most likely that you are going to fail, you take the appropriate actions not to. You follow the process. You test, again and again.
The manager is permanently in the trenches, trying to figure what is going wrong and how to fix it. The team works overtime, is dedicated. It's bonded together at least by the fact that if one screws up, everybody screws up. I hope they are more bonded by the fact that they are doing something great (doing the impossible is most always great), but hey, you take what you can.
Perhaps it's going great because the team is actually thrilled by what it's doing, perhaps because it knows it's screwed if it fails. The result is here: even though it might involve much pain, the project will most likely succeed.
That's easy. I'll do it before lunch
Ever heard that? Ever said that? When I hear (or say) that, something blinks in my head. Warning: this is not going to be done. And if it's done, it's most probably going to be botched.
Easy stuff is hard to do because you have to treat it as hard stuff if you want it to stay easy. And since we are humans, this is seldom the case.
When I hear the "That's easy, it's going to be done in an hour", I usually add in my head things like "If I have nothing else to do", or "While chatting about last party" or "While playing Solitaire".
I hear: "That requires 10% of my intellect to do. I won't dedicate 100% of my brain to do it. In fact I probably won't even dedicate 10% because I'm just bored".
You are just not going to get the same dedication. Boredom, carelessness resulting of routine, you name it. The task would be easy if your people devoted themselves 100% to it, as they would on hard projects. But it's not going to be the case. Not unless you intervene at some point.
It's the manager's fault too
Same thing applies to the manager. On a hard project, he is going to be in the trenches. At any given moment he'll have a perfect understanding of what everybody is doing, what is left to do, what is the next thing that is going to screw up.
On an easy project, well, he is going to be monitoring loosely what is going on, but chances are that he is going to be more busy on that hard project that is going on at the same time. Hence he is not going to do one the of the most important thing he has to do: "We're screwed!" prevention, AKA problem detection. And the easy projects turns bad, because really it was a hard project in disguise, but it looked nice on the outside.
The calm before the storm
I learned with time that when everything goes smoothly, it's time to ask yourself where you are screwed. It is not normal in our job for things to be easy and go smoothly. When it does, it usually means that there is a problem you are not conscious of that is lurking in the dark waiting for the perfect moment to rip your project apart. Routine is one of our worst enemy.
With people from Sales, of course.