Interesting! I assume that 'failure' means going off the back of the treadmill? In other words, falling off the pace.
Ok, so if your coworker is going faster than 5K pace, and made it to 20 min once, that means his 5K is slower than 20 min.
Likewise, if you are going faster than 5K pace, and you made it to 18 min, that means your 5K is slower than 18 min.
So, you guys are running maybe 2.5 or 3 miles?
The workout, then, is as hard on you as doing a 2.5 or 3 mi time trial. Decent workout, maybe not advisable to do more than once per week. Could be a fun part of a training system, if well planned out.
I'm not an expert on this, but If I'm not mistaken, I believe this effort is similar to a race effort or a VO2max session. Racing can be an important part of training but should not be done too frequently. VO2max work, if I understand it correctly, would get better results if broken into repeats versus one long effort.
One of the reasons being that running all-out for 18-20 minutes (as a workout) is more likely to tear you down than build you up, again if I understand the concept correctly.
Another reason being volume of the workout. The "faster than 5K pace on a treadmill to failure" session, I'm guessing, is 2.5-3 miles of running. Compare that to, say, 4-5 x mile repeats at VO2max pace with equal time recovery. More volume, less stress on the body, more benefit.
Sometimes it's important to remember that there difference between being a "workout king" and training properly for good results.
tl;dr It all depends on the purpose, frequency, and context in training.
Anybody who knows more than me, please correct me if I went wrong anywhere in my thinking.