Mostly you can tell by the fact that plants that are considered reliably hardy in your zone, & grown by many people here on the forum in your zone, DIE in your garden over the winter, either never returning in the spring, OR by trying to return in the spring by sending out one sickly sprig & then quickly dying off, & they do these things for you over multiple attempts at growing them. Believe me I have plenty of experience with this. Why this happens is somewhat a matter for speculation. My experience has been that plants labelled with cautions about drainage (beyond the "moist but well-drained" nonsense that is on so many labels) may have considerable difficulty overwintering in my garden, despite zone compatibility. In addition, plants labelled for zone 6, which some people around here can grow, will almost NEVER survive winter for me, unless planted under the eaves at the highest point in the yard. Zone stretching is painful here. I blame this on "winter wet". My definition is somewhat broader, however, than Whaas's is. I can have this problem just about anywhere in my yard. I garden on very heavy compacted clay - where everything drains slowly. I have gardened on this clay (I still don't call it soil) for over 15 years now, constantly amending & improving it, with some gains, but a lot of plant losses. In very cold, consistently cold weather, with good snow cover, my losses are now usually slight. In a year with freezes, ice storms, occasional snow cover, odd warm spells, followed by winter as usual, losses are high. My theory is that many of these plants survive my winters, just not my sometimes nasty autumns & wicked springs. To combat winter losses I use every trick in the book. Amending soil & planting under the eaves I have already mentioned, & raising beds is certainly helpful, along with selecting plants that are moisture loving (remember most of these still need some air in the soil), always picking major shrubs and trees compatible with clay, & planting high, using mounding & little shelves, etc. I find that rock works the best, big rocks, little rocks, gravel & grit & granite fines, in the soil and on top of the soil. Commercial products like Profile (fired ceramic bits) can do wonders but are expensive. We could not keep a front curb tree alive in our (very non-urban) setting (probably because of the piled snow Whaas mentioned, rather than the dry heat so often associated with these locations) before we discovered it. A mailbox planting is out of the question, I'd have to raise the mailbox too high for the mailman. :))

A French Drain and lay big snow-shoveable flat pavers on top of the gravel or rock as stepping stones. Both the gutters and the surface water feed into it. YouTube it. You can get supplies anywhere. They make them ready made even. Pipes let water in and then down and out where you want it to. You gotta have a grade going downhill. If there is no downhill then a sump pump.

If it the actual drain (floor drain?) and not the discharge tube, you need to treat it like any other blockage. If you don't own a drain snake, call a plumber.

Locally we have contractors specializing in site prep for new construction. I would contact one of them for grade solutions and referrals for concrete contractor. .