Do I have that sort of problem...?
No, not really. I usually end up GM'ing and I don't particularly try encouraging anyone to play any certain class. I have my restrictions (no monks or psionics, for example), but what I allow...I allow.
In fact, while I don't think it's the worst thing in the world to try to encourage certain classes before the game, I do believe anyone who starts throwing encounters at a party with no other purpose than to make someone play a certain class is a bad GM indeed.
"You lack a cleric? Well, have some undead!"
Bad GM, bad.
I don't bother trying to make my players play one thing or another. I prefer they play what they want. Heck, my Ravenloft game - where it's arguably even more important to have a cleric - has no cleric. It has a Ranger/Bard, Rogue, Aristocrat/Fighter, and an Aristocrat/Wizard. The party healer's the multi-classed Bard. The undead smacking is nearly non-existent.
A game should, after all, reflect the party, at least in part. It's supposed to be fun for everyone. So I shoot for a compromise, if I can. Run the sort of story I want and mesh that up with what the party's playing.
Of course, they may not be prepared for all encounters - but it's because it makes sense for the encounter to be however it is, not some set up based on what the party does or doesn't have.
There's no denying that a party without a cleric is lacking someone important. But it's more important that everyone's playing what they want as a PC. A GM has the entire game world to suit to their tastes. A player should at least be able to play what they essentially want instead of someone being pigeon-holed into the Cleric.
Of course, a party death or two may change their minds. But I never run encounters specifically encouraging a certain class to be played should a death occur and think it's in poor taste to do so with that specifically in mind.