This achievement is story based, you can't miss it. It comes after the first heist when you rob the jewellery store prior to meeting Lester, after scoping the place out, and getting hold of equipment, you do the heist.
The heist can go differently depending on which way you choose to do it, quietly and quickly, or all guns blazing. Once it's done and you've escaped back to Lester's, the achievement will pop.
NOTE: There's a strange phenomenon happening just lately with the Achievement system on the Xbox One. Achievements aren't popping visibly or audibly, but they do. Your console has to be connected to Live, so if they don't pop, check your Internet connection, and the Xbox Live status page at http://support.xbox.com/en-US/xbox-live-status
They DO pop correctly, as I obtained them on the 360 version.