This would have been better if it had been posted in the Corporate or Part 135 forums as you will find answers from many more pilots who fly into ASE. Perhaps a moderator can move it.
The weather conditions in ASE are highly variable. Some days are very pleasant with almost no wind or clouds. However, other days (especially during winter) marginal ceilings/visibility requires constant monitoring of the weather. There also can be moderate or worse turbulence in the mid 20's and down during your final descent into the area.
Aspen is not a trivial airport to fly in and out of. The combination of close-in high terrain, variable weather conditions, and aircraft performance limitations require a great deal of pre-planning and consideration. You should request simulator training in Aspen instrument procedures during your next training event, as well as seriously discuss these issues with an Aspen-experienced pilot.