If you’re being considered for this position by the boss with “over an entire life worth of experience difference” more than you, then trust that experience in their hiring judgement too.

There are SO MANY THINGS that simply cannot be taught. Maybe your boss would far rather teach a guy how to do advanced sysadmin tasks than try to teach him how to own and operate a working conscience, for example, or have to depend once again on a technical genius who lies constantly and fails to show up on time. Maybe he likes that you’re learning – and you’re actually continuously doing the unseen tasks of teaching yourself – and not just coasting on some very thin laurels you constantly repeat to everyone so that no one EVER forgets you’re a genius, even long enough to refill your coffee. And those are just examples; there are many, many more where those came from.

See, employees have a lot more to offer than the actual job skills. Those are just the first step for a seasoned manager. And sometime they’re not even as important as the other skills you’re discounting as unimportant. This boss isn’t thinking of you in this position because he likes constant hemorrhoids and anal bleeding; if he’s thinking of you in this position it’s because he knows you can make a go of it, learn on the job, and not make his life hell while you constantly lie about what you can do (including the personal five-finger employee discount program you created for yourself and think no one knows about).

Maybe he likes that when you say you’re gonna do something, you either do it as planned or keep him apprised of actual progress. Maybe he likes that he can trust you with outside clients, and knows you won’t show up in the C-suite in flip-flops with a bag of Fritos and then stare at some suit-wearing highly-paid CFO’s bodacious rack for the whole meeting while he’s trying to get or keep the funding that is what keeps you both in a job. Maybe he just likes that you don’t lie when you fuck things up, and look actively for solutions instead of engaging in immature emotionally self-protective behavior to the extent no one wants to work with you. Again, lots more examples where those came from.

But whatever his reasons, if you trust his experience, and he seems like a decent person and good manager, then trust his managerial expertise too. Just tell the truth about where you are, regarding both skills and concerns. Don’t exaggerate. Maybe let him decide if you’re a good fit before you turn him down, lol. IOW, if it’s ever offered, don’t turn this advanced position down on the sole basis of your inexperience.

Effective managers know the difference between good employees and bad ones, and chances are almost perfect that HE learned on the job too. So if he wants to hire you for this, even knowing your true level of skill, he’ll make sure you have support just to save his own ass – and you can ask about the kind of support you’ll have in the job yourself. Hope this helps.