One of the things that people have mentioned to me in the past regarding my event management skills is my reaction time. They say, “You are always on top of things when they go wrong. How do you do it?”

My response never fails to make them laugh. I offer, “I always assume something is going to go wrong. I may not know what it is but when it does happen I’m ready to fix it.”

That may sound like a cynical take on planning and operations but it’s served me well for many years. Why is it that things we spend so much time working on always seem to go off the rails?

Complexity Fails

Whether it’s an event or a network or even a carpentry project you have to assume that something is going to go wrong. Why? Because the more complex the project the more likely you are to hit a snag. Systems that build on themselves and require input to proceed are notorious for hitting blocks that cause the whole thing to snarl into a mess of missed timelines.

When I was in college studying project management I learned there’s even a term for time saving: crashing a project. Not literally crashing the project into something but instead looking for ways to trim the timeline and work through issues. Why is this a common term? I’d hazard a guess that very few projects actually stick to their timeline. It could be a parts delay. It could be a team taking longer to work through an issue. Mercury could be in retrograde during sunspots. Whatever the case may be, projects are designed to have floating timelines.

This imprecision built into project planning made me realize that the only way to be really sure that something would get done properly was to anticipate the errors and work through them. Part of the way to prevent these issues is to reduce complexity. You may not be able to work through every potential scenario where something is going to go sideways but you can almost always tell where the problems will arise. Any module of work that has lots of moving parts or lots of people with specific deadlines is going to be a trouble spot. The more components that depend on each other means a greater chance that any one of them slipping will cause a delay that requires attention.

If you have a project or are planning something that has complicated steps for a specific goal, try to break those down into more simple things that don’t depend on each other. Have a team that needs to write a report based on the research from another team? Don’t bundle those together. Have the writing team working on things that aren’t dependent upon the research team just in case the data isn’t delivered. If you’re building a house and you are planning on having things done that require a roof being installed you should have a plan for what happens if the roofers are behind or the shingles don’t arrive on schedule. Finding these extra bits of complexity and eliminating them will go a long way toward solving recurring sources of frustration.

Be Prepared for Problems

The motto of the Boy Scouts is “be prepared”. It’s something I constantly remind the youth in the program weekly. Be prepared for what exactly? It doesn’t matter what if you’re properly prepared. You don’t have to be prepared for every possible scenario but you need to have the flexibility to address a wide variety of potential problems.

Take information security, as a prime example. How will your enterprise be breached? There’s almost too many ways to consider. New zero day? Backdoor password installed years ago? Phishing your key employees? Good old fashioned malfeasance? The list of things are endless! But the results are always the same. Attackers look for things of value and either steal them or disable them. Thieves steal and chaotic souls cause chaos. The entry is unknown but the results of entry can be quantified and considered.

You may not know how they’ll get in but you know how to stop them once they do. That’s why you should always assume you’re under attack or already breached. If you construct the system in such a way as to prevent lateral movement or even create policies to keep data safe at rest you’ll go a long way to preventing unauthorized users from accessing it, malicious or otherwise.

Is assuming that you’re always under attack kind of paranoid? Yes, it is. However, if you assume you’ve been breached and you are wrong all you’ve done is ensure that your data is safe and secure. If you assume you’re not and you end up being wrong you get to spend a lot of time cleaning up and sending emails to your boss and your resume to the next place where you get to make all new assumptions.

Tom’s Take

The optimist in me wants to believe that you can plan something so well that there isn’t a chance a problem can happen. The realist in me knows the optimist is crazy. That doesn’t mean I should just stop planning and hope for the best when I need to tap dance my way out of a problem. Instead, it means that I need to consider all the possibilities and try to have an answer for them, event if they’re remote. That way I’m never caught off guard by the wackiest of issues.