1. Start with a mostly manual, people labor based, system that works well (handing Joann receipts) 2. It begins to not cost-scale well with growth (department size increases) or a salesmen comes around with a service that offers to do the same thing for less (Concur) or both 3. The company switches to reduce costs 4. The new service is cheaper partly because it offloads work onto employees (filling out travel expense forms) and by cheaping out on the experience (not caring that the forms are not easy to understand and the system is annoying to use) 5. Employees now have to spend time doing a task they never did and their experience is worse

And it stays in this state forever because the observable costs (service cost vs some number of Joann's) are less. The fact that expensive employees (A department full of Phd's) are now wasting time and being annoyed by this system are not seen. The hours used to fill out those forms and lost productivity due to anger are never accounted for. Also the higher ups are detached because they still have their own personal Joann's taking care of everything.

In the reimbursements example, the goal shifted, by design. The environment moved from high-trust to low-trust as the department grew, and the aim moved from "keeping people happy" to "spending less money"/"not being taken advantage of". Not defending it -- I hate paperwork like this -- but it seems almost inevitable as groups of any kind grow large enough and you actually can't assume good faith anymore.

I would do the typical thing of "take picture of receipt, upload receipt, specify how much it cost, etc.", and for the most part it was seemless and it would be sent to my bank account.

One time, I bought a box of Fiber One bars at a CVS Pharmacy and expensed that. I got a phone call from the billing department asking why I would expense something like that and I said something like "because I don't usually eat that healthy during business travel and I suspect you can guess the reason after that". They told me they would get back to me, and then I got an email telling me that they rejected the expense report and I would have to file it again to get the rest of my stuff reimbursed.

I can be a pretty petty dude, so I filed it again, completely unchanged, I get another phone call telling me to remove it, and this repeated two more times. Eventually I complained to my manager and he was able to get them to let me expense it and it all worked out.

I find it amusing, because the box of Fiber One bars was less than five bucks. I suspect all the time that they wasted of theirs and mine probably cost considerably more than the $5 would have saved from not covering it.

Just to ensure you know that Joan was not technical, because old.

Similar for me in the corporate world, in the 80s, I just had to save the receipts and give the to the Department Admin. Easy as pie.

Then that all changed in the 90s. Everytime I traveled, using the 'canned' system provided to us, you could spend days trying to fill in the forms. It would ask you for all kind of codes no one knew to supply.

Multiply that by 10s of employees, there is no way firing a Dept admin and contracting that out saved any money. It has to cost the company 2x or 3x as much as one admin costs. And that is a low-ball estimate.