The U.S. Nuclear Navy, for all of its many flaws, gets this right. Generally at least once a year, the head of Naval Reactors - a four-star Admiral - tours every vessel, which may include a brief underway period. During this tour, the Admiral will talk to the engine room watchstanders, with all senior leadership removed. They’ll ask how daily life is, what they find challenging or annoying, what they like, etc. There’s obviously a lot of self-filtering (though sometimes not - Navy Nukes are not known for their social graces) that occurs, and also what a junior watchstander finds annoying may just be a required part of the job, but some useful signal is gathered.
Even outside of the nuclear program, one standout example was Admiral Zumwalt, who as Chief of Naval Operations implemented 70 different changes over his tenure as a direct result of talking to sailors, all of which were designed to improve quality of life, efficiency, or communication.
Why would you when all of the reports you're getting from your managers are 5/5 stars and "everything's great". Once an organization gets large enough, the information that reaches C-suite has been filtered through so many layers that it barely resembles reality anymore, even when you remove malice from the equation.
He was put there because he was with the company for years before and he led other departments fine.
Since he can't evaluate anything IT related himself he relies on 'advice' from the people beneath him who try to get the most budget for their departments by overstating how important they are.
This layer beneath him is mostly product managers, RTEs etc... (We are SAFE Agile! Developer Velocity, Woohoo!).
They also don't know much about computer and if they do it's very domain specific, such as SAP or so.
These people try to fight for budget by overstating their importance. They demonstrate this by having more apps and more people relying on them.
"Look we handled 2000 support tickets, the company would grind to a halt without us!".
Never mind that having 2000 support tickets is a bad thing. And also mostly caused by their shitty apps.
This keeps going on and on. I have 10 years experience as engineer and wanted to see "the other side" but it's so exhausting.
A few months back a 'privacy officer' asked why the first and last names of our employees were in the Active Directory and ordered them to reduce the privacy risks.
They failed to specify what risks. Couldn't articulate them even when asked. They also didn't say when the risk would've been reduced 'enough'.
The team was panicking as they were now 'non-compliant' with company policy.
I had to intervene personally to make sure this single directive didn't derail our entire company.
I’m constantly having to fight people to not add new, inactionable alerts as knee-jerk reactions to incidents. I swear the thought process is “an incident happened, we added a new alert - look, we’re proactive!” instead of, you know, fixing the root causes.
The people who start a company care deeply about the problem they're trying to solve.
The first N employees also care - they're willing to risk working for start-up because they can see the potential and want to help.
But then you hire, say, an accountant. The accountant doesn't care about your mission. You are just another client to them. You need someone to staff the phone or sweep the floors or design the logo or whatever. Why should they care? You're not paying them to care, they're not invested in the company nor its success, and they believe nothing they do for the company will change their personal fortunes.
Then, before you know it, you have a couple of floors filled with people who have no incentive to care.
It is incredibly difficult to run an organisation where everyone is mission driven.