I'm not a security pro I am strict about security. Your question precisely reaches the core of IT security: trust. As i see it one should never assume that Bob can be trusted. Sure, Bob might be a really nice and trustworthy guy. He's worked at your company for 20+ years. However, the person "Bob" is entirely irrelevant in your IT infrastructure.
Bob uses arbitrary 'relays' that permit access. Relays can be anything: a password, certificate, hardware token, iris scan, DNA. They're keys that permit access to your system. If your question is about verifying the identity of the person who is using a key, the only honest answer probably is that you'll have to be in the same room. In all other cases I think you mustn't assure yourself that that Bob really is Bob and currently not being held at gun point while gaining his access. So in your IT infrastructure design plan the logical thing is not to refer to "Bob": an entity gained access to your site.
Because you can only really know that 'an entity' gained access with a key that you passed out in the past the proper perspective probably is to limit the number of doors the key can open. The more keys you pass out the less doors they open.
OpenVPN also has an option to permit only one concurrent connection per key. Then if Alice does log in with Bob's key while Bob is already inside, Alice is denied access. Unfortunately this also means that Bob can't login when Alice is logged in with Bob's key. So you should configure your system to inform you of concurrent login attempts from multiple source IPs. And kick off both when some violation occurs so Bob will have to dial for help.
The point is: don't assure yourself of things you can't be sure of and keep this in mind when designing your security plan. Assume there's always a smarter person out there, way ahead of you, who can't wait to prove you wrong... just 'for the lulz.' :-)