I’m amazed that this is what happens every. Single. Time. And yet we plow ahead with this kind of projects like we have no idea it’s the usual outcome.

A couple years and millions over budget later, we rediscover this axiom. I really don’t get it. And try to warn about this, you’re labeled as not a team player or whatever and paint crosshairs on your back for the next round of layoffs. It’s just soul sucking.

The details about the day-to-day operations disappear quickly as you move up the hierarchy.

My boss recently had a meeting with a large customer of us, we deliver a product used heavily by one of their departments. Here's roughly how that went down:

My boss: "Well, what about when you do orders of type X?"

Manager: "Oh we don't do those"

My boss: "Really?"

My boss brings up the order list and filters on type X, finds at least one entered each day by user ABC

Manager: "Oh... so that's what she does"

So that information was lost in just one level.

This is why we try our best to get the actual users involved when discussing requirements with a customer. I don't think I've ever experienced a project where at least one of the users haven't brought up some edge case the manager wasn't aware of or had completely forgotten.

On the flip side, the projects where the users are left out of it until it goes live never goes well. We'll get it fixed eventually, but there's always pain for far longer than necessary.

Trying to do those two is a clear signal of incompetence.

General Marshall, Eisenhower's superior also delegated broadly, while making key decisions as to the timing of the invasion, which units would be involved, and making sure all the disparate organizations involved were used to the best effect. Again, delegating broadly, as a good commander should.

This goes on and on up to Roosevelt himself, the Commander in Chief at the time. Does he know jack about the tide tables on Omaha beach? The range of a German 105mm howitzer? Of course not. Yet he clearly mandated the important decisions.

All three of these leaders were clearly EXTREMELY competent.

Most of my work right now is trying to eke information out of customers about their ERP system so we can get it connected via EDI or to their Ecommerce system (shopify whatever).

So we go live, with a whole process revolving how payments are accepted - and then within an hour there's a problem. Nobody mentioned that certain customers have a different payment workflow!

Back to the drawing board, except we're already live.

This happens again and again.

This is what big corp suppliers like IBM, Oracle or SAP thrive on. CEOs and executives not actually knowing the intricacies of their company, and underestimating the risk of creating a very expensive second system effect.

The fact is the higher you go the concerns separate. I think the army motto was "go 2 levels up". You're a grunt, you need to know what your platoon and your company are up too and what the goals are so that if you can't follow the plan directly, you can still hit the objective. This is good because no plan army or business, survives reality without changing.

In the same way, you can only go so many levels down.