It’s always more complicated than it looks.

Case in point: Houston

Your hypothetical challenge: Bring the city back on line. What does this entail?

Lots and lots of lots and lots, that’s what.

Understand, I know nothing at all about civil engineering, or emergency management, and not all that much about enterprise risk management. What I do know is that nobody else can keep the list of everything that has to come back on line in their head either, let alone the interdependencies that could lead to creating a proper Gantt chart.

Oh, by the way, a half hour of Googling failed to uncover anything resembling a disaster recovery plan for the city of Houston. An emergency management plan yes, a recovery plan no.

Which isn’t necessarily bad management. As with IT’s ancient habit of trying to create comprehensive software designs before beginning to write any code, so disaster recovery plans of metropolitan scale or larger for disasters of inordinate magnitude are probably pointless. If, that is, they do much more than list the organizations that need a recovery plan, specify what one should encompass, and insist they have them.

Even then there are limits. As everyone who’s involved in disaster recovery and business continuity knows, a plan that isn’t tested isn’t a plan.

And along came Harvey.

Case in point: New York City.

I worked with a client there several years ago, enough that a corporate apartment made more sense than staying in hotels. The result, though, was that for a couple of years I qualified as a resident, meaning I owed New York City taxes. These were (1) substantial, and (2) business expenses, not directly deductible from my Minnesota state tax bill.

This sawed me off. Until, that is, I saw a sign in the midtown Whole Foods that explained New York City creates enough garbage every day to fill the Empire State Building.

It occurred to me then that I had not the slightest idea how to go about removing that quantity of garbage every day, and that garbage removal is far from the most complicated challenge in running New York City.

As I had no idea how to run NYC I certainly had no idea how to run it at a lower cost, which meant I should put up and shut up. I benefited from services I didn’t even know were being provided. My New York City tax burden was how I paid for them.

Case in point: Any legacy retirement

Over and over again, companies make this mistake: They decide to retire the ancient mainframe batch COBOL system the whole company has been running on for forty years. And from this decision comes a logistical nightmare, because no matter how you go about it, you can’t shift the entire company from the old system to a replacement at the flip of a switch. It has to be phased and staged.

And no matter how you go about the planning it turns out many business areas will be running in a mixed environment for a year or more.

But unlike New York City or Houston, a lot of this complexity is a self-inflicted wound, the result of looking at exactly the wrong end of the horse.

The problem is the decision to retire the mainframe. Not that the company should stay on it. No the problem is that this focuses everyone’s attention on what they’re migrating from. In addition to the logistical migraines this thought process creates, it results in something even worse than the planning nightmare: When the project is done and the mainframe has been retired, the business runs pretty much the same as it ran before it invested the zillion or so direct dollars, plus sweat and opportunity costs, that were needed to make it all happen.

Much of which would have been avoided had everyone focused on the opposite question: What to migrate to.

Even better, they should be focused on how each business manager at every level wants to run his or her part of the business differently and better, leading to an applications portfolio plan that will mostly let them do so.

Taking this approach, things still aren’t simple. They are, however, simpler — a lot simpler, because (for example) moving Sales to a modern CRM system is, at a minimum, clear in what has to happen.

And moving Sales to a better sales process that’s possible because of the modern CRM system’s features has actual business benefit beyond a modest reduction in the IT operating budget.