The DPE that we used 90% of the time was (is) a very fair guy but the higher you get on the ratings totem pole the tighter he got and I’ve done 4 rides with him myself. CPL ME add on, CFII, MEI and ATP.
On the latter three he was brutal.
Even though I knew him for over 10 years already I never expected any special treatment.
My initial CFI passrate with him was 66%. CFII only one ever failed.
Never had a MEI applicant fail.
Then again I didn’t sign anybody off with 5 hrs either.
More like 15-20 and I’d break into your house at night and wake you up and have you recite the definition of Vmc.

If your school uses Santa and quotes you 5hrs for your CFII and come checkride day and Santa is not available and they use a real DPE, get ready for a day of reckoning.
School doesn’t want to lose face and your instructor says you’re the greatest and you end up getting clubbed like a baby seal.

This literally just happened to me today. I failed my CFII oral because I showed up unprepared. I’m upset because the same things I was unprepared on are the same things I asked my instructor on the very first day of CFII training and I was told to “not bother with it”. For example, on Day 1 I asked my instructor for advice on syncing my lesson plans with the PTS. He literally told me to not worry about either of those things and just focus on the IR ACS. I listened to him. Obviously that was a big mistake. Also, I was completely unaware that there was a new form for filing an IFR flight plan. I used the old one, and my instructor even checked it and said it looked perfect. The DPE roasted me for being a CFI who showed up with outdated information. I feel terrible

I'm having flashbacks from All ATP's!
Think 66% of my checkrides were pushed before I felt ready.

Your instructor sounds like an ***hat.

Here's the important question for hiring, though: what will you learn from the experience? There is something to be learned from such an experience to make you a better pilot overall.

Why do airlines or other companies harp so much on failed check rides?
How many people have an unblemished record? Of course there are some. But THAT is way more rare than someone with a (gasp!) failed checkride in their past.
And sometimes, that may have occurred 20 years ago, or more. How long do you have to answer for it?
Does something (whether it was your fault or not) from 1999 matter that much today??

Same reason that we have a 1500 hour rule.

Yes i’m still really upset about this because I take being a CFI as well as my flight training very seriously. It really ****ed me off when the DPE said to me “how can you be a CFI and be this unprepared. This is very unprofessional and you’re expected to be teaching students.. just how do you expect to do that?”. When my CFII told me that I was perfectly ready for the checkride, I was glad and continued to study hard with what he told me to do. Had he not told me to ignore the PTS and my lesson plans, I absolutely would have continued to use those resources. But, with him being the CFII, I trusted what he said.

I’ve thought about that same question. I guess I learned it’s better to over-prepare. I’m honestly not sure yet how to word that one out for future airline applications.

Don't most people have no failures?

Most probably have no 121 failures. I think most have at least 1 GA failure usually Private, Instrument or CFI

PRIA goes back 5 years for previous companies and I think checks FAA failures/violations on your entire record