After you do it long enough and use a hand priming tool, you can tell by feel. However, if you use a press it can be tough to tell. They make primer pocket gauges with go and no go ends.
From Brownell's:
Stop guessing about your primer pockets. Know for sure with the Swage Gage Primer Pocket Gauge. Available for Small or Large primers. Check primer pocket depth and diameter. Use the "Go" end of the gauge to check primer pocket depth, if any crimp is properly removed, and if the primer pocket is loose. If it feels loose on the "Go" end of the gauge, use the other end of the tool, the "No Go" end, to test if the primer pocket is too loose to hold a primer. If the No-Go gauge slides into the pocket, then you know to junk that brass.