I like the interviewers use of "cloudy settings" in this invu... as that's my opinion of a lot of cloud computing. Cloudy, with a chance of meatballs.
The fundamental question you have to ask yourself, when considering cloudy deployments is this: *when* your link breaks, what won't you be able to do. If that's crippling, then you need redundancy on your uplink from (say) your office -- yes, I have seen fairly large deployments where office apps and email were outside the building.
Yes, I have seen incidents where *triple* uplink redundancy was not enough.
And even if it is, does the added cost of triple redundancy on your uplink eat whatever cost savings you expected from the cloud? While "you can go somewhere else and reach everything" is great, most 100-seat companies don't have another 100-seat building empty somewhere to go to... and "everyone can work from home" isn't always as efficient as you'd like.
So the sun may be behind those clouds, somewhere, but as I hope you'd expect, you do have to look for it, and make sure you know where it is, before heading into the clouds.
Oh, and understanding that *there are no actual clouds involved* (as I'm told a real study of real Americans says a majority believe) is helpful too.