Have you ever had someone look at and ask “So, what’s the hardest part of your job?” I have, more than once. Honestly, I wish they wouldn’t. The things I find hardest are simply not what I would like to admit to. The hardest of those, by far, is probably one which public admission to would get me canned as a project manager. You see, the hardest thing in the world for me is to stick to the plan when a risk manifests itself into an issue.

What does that mean? It’s simple, really. Like all project managers I spend a lot of time planning with the team for what will happen when something goes wrong. I work with the technical team to plan out approaches to technical risk. I work with the executive team to plan out ways around political risks. Lawyers and auditors, managers and the great white elephants all get their say. In project lingo, we “mitigate the risk.”

It’s a natural human tendency to forget these “mitigated risks.” We’ve spent days discussing the blessed things. Sometimes weeks. Then one or more of them suddenly occur, at the worst possible time, in the worst possible way, usually when the team just pulled one or more all-nighters struggling to get the system operational. Everyone’s tired. The executives want everything fixed then they want someone to blame the failures on. The junior team members curled up in the corners hours ago and everyone wants to go home.

It’s the project manager’s job to remember the mitigation plan and act on it. In the face of everyone, including his own bosses, desire to do what is expedient he has to stay on target. No matter how much it hurts the team in the moment, he has to push them to execute the plan, whether that plan involves the deployment of another software patch, a whole-scale rollback of the newly deployed system, or a call to the CEO telling him his company will be off line for the next 24 hours.

I find this difficult. It’s not that I’m not stubborn as a rock. I am. It’s not that I don’t remember the plan. I remember the way to my 1st grade class room; I can remember something we hashed out a few weeks ago. It’s not even that I mind suffering myself. What I do not like, though, is watching my team suffer for what will undoubtedly turn into a major failure.

On one hand we have honest suffering. People work hard, put a lot of themselves into their jobs, and sacrifice their time on the altar of business in order to make these things work. Watching all of that time and effort go down the drain honestly makes me sick. I hate it. I’ve always hated it. It would be easy to do the expedient thing and stop the suffering immediately rather than push people to do the right thing.

On the other hand, I also know that a major failure is generally a resume generating event (RGE) for someone in my position. It’s tempting to let someone else step up into the forefront, claim the immediate victory, and let everything go to hell in a hand basket. That someone else, often an executive, can define victory however he likes.

Unfortunately my job as the project manager is not to stand aside. Empathy and fear both have their proper place in my heart, but my job is to work out the right thing to do and then if necessary force others to execute when the time comes. If that forces me into an RGE, so be it.

It’s not easy, though.