This is most likely going to sound weird, and I'm sure I'll step on a few toes with this, but here goes.
The problem really isn't training, I think the problem is experience.
In the training environment, if the performance charts dictate a climb to 410 and if the pilot respects the high/low speed margins, it's "supposed" to be able to achieve the altitude.
As any pilot knows, your anticipated performance and your actual performance don't always match up.
I'm not sure how to specifically train a pilot that if you've got an abnormally high alpha near your peformance limit, chances are that you've probably already exceeded it and need to respond before the aircraft responds for you.
Training is based upon 'reacting to an annunciation' and pulling out a checklist than it is doing detective work and figuring out what the real story is.
A few years ago, in recurrent, we had a second-stage engine failure. Basically secure the engine, determine that the departure airport requires a divert to our takeoff alternate and go thru the engine shutdown procedures. Very simple, trucking along to our takeoff alternate, the captain decides to open the crossfeed valve to keep the fuel load balanced and we lose the other engine.
Fuel contamination. Is there a fuel contamination annunciator? Nope. A procedure? Maybe. But as you're drifting down, you'd certainly better divide the cockpit, close the fuel crossfeed and fight like heck to get the engine restarted - if it even will restart.
Ok, back to the CRJ...
In flight, you can look at the cruise page (at least on the series that we have in the MD-88) and see what the "MAX FL" is, which is normally the maximum attainable flight level taking into account your performance based upon whatever the operator has programmed in as a margin index.
Push the button, "Yeah, we can make it" and go.
However, if the performance of the aircraft (slow speeds, high alpha, etc) might suggest that one of the crew should pull out the Operations Data Manual (it's a Delta word for 'performance manual') and take a peek at how many G's of protection you want and what the low speed and high buffets are. At times, you may only have a +/- 15 knot margin between a high speed buffet onset and low speed buffet onset.
The inflight characteristics of a straight-wing Beech 1900 where you rarely get up to FL250 and a swept-wing CRJ up in the high 30's/early 40's are two completely different animals. The Fl250 limit on the 1900's isn't performance, it's the ability of the aircraft to perform an emergency descent within a specified period of time to a prescribed altitude. But I presume the 410 limit on the CRJ's is more engine/wing than it is descent-based like the 1900.
Ok, I'm rambling. Time to forage for food.