That's not how the bond market works (for the most part). Lots of bonds (including some risky bonds) price above par but will have a correspondingly low interest rate such that their yield is in line with other similar bonds.
Bonds have a face value (which you get paid at maturity) and a coupon (interest payment calculated as either a fixed percentage of face or as a spread over an underlying rate * face)[1]. Both of those components matter to investors and factor into the so-called "yield to maturity" of the debt. The bond price dropping means that the secondary market is demanding a higher yield to maturity on the debt.
The main drivers of that price are the underlying risk-free rate of interest (which compensates investors for the difference in utility between having cash now and having cash in the future and essentially arbs out between all the different risk-free or near-risk-free instruments they can invest in) and the credit spread (which compensates them for the likelihood of default and arbs out with other instruments of similar riskiness and the prices of things like CDSs).
In the 1yr T-bill example, almost all of the price discount you are quoting is about the risk-free rate of return. So say the rates were at 4% when a 10yr note was issued, we are now in the final year and rates have gone up since then, then the price of the bond would drop so that investors get a yield-to-maturity on this bond that is approximately the same as other instruments of equivalent maturity.
The WeWork example is going to be driven by the credit spread - how likely WeWork's is to default and how much investors would be likely to recover in that event. The price going down is to do with the credit spread widening and therefore investors demanding a higher interest rate to compensate.
[1]I'm simplifying a lot here given all the weird and wonderful types of bonds you can get.