I know that feeling
Not the free flights, never had one. And not just in the techie part of my job, though there were a good few of those. But in the education ( the main) part of my job too. I used to get the brass angry by asking those awkward questions. Like the launch of the borough wide anti-bullying policy. I simply asked how they were going to follow it up once the publicity and campaign leaflets were over. Cue hissing, intakes of breath and angry looks from people in shiny suits. Or the Healthy Eating when I asked why they were setting the initial target at every child eating 5-a-day, which seemed unlikely since some of our kids never ate any, instead of aiming it at the ones who ate none a day first. More intakes of breath Or the complicated plans for the roll-out of a new broadband contract that had lots of time scales, but no underlying explanation of how they could be met. No intakes of breath that time. Just patronising smiles and reassurances by " people who knew".
(The bullying policy did fade, so did the healthy eating: And the broadband targets? They weren't met either).