What is a good way to DM when the party searches for something?

I am newer to DMing and was hoping to get some advice on an aspect of the game I feel poor at.

My players have had multiple instances in the story where they are looking for something / someone. Examples being:

My issue thus far, is that it feels as though its more of a chore then a cool goal to try and find the thing. They roll for perception to see if they can find stuff, and then that tends towards it.

I think an additional part of this is that one of my players has a familiar that they use to fly up and obviously gives them a large advantage at searching (though to make it very clear, I am happy they are doing that because that is a very good application and what they wanted fantasy wise to get out of their familiar).

For this upcoming search for this dragon cave, I want it to be a bit more of a game, more choices and intrigue. I've thought about getting a mountain map with a cave entrance somewhere, but I worry that walking around a map when not in combat doesn't really serve much of a purpose (because we play in person). So I am not entirely sure what to do to make searching for things more interesting and feel less like a chore.

The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure. When the outcome is uncertain, the dice determine the results.

So, if they will inevitably find the dragon cave, there is no need for an ability check; you simply say: “After searching the mountain for several days, you are standing at the opening of a giant cave. This must be it! What do you do now?”

Otherwise, it's a failure, which means the character or monster makes no progress toward the objective or makes progress combined with a setback determined by the DM.

Now, as you’ve described the challenge (find the dragon cave), there are no consequences of failure. But if you want to (“want to”, not “have to”) you can set different challenges:

But those are different challenges from just “find the cave”.

Every character likes to feel that they are the one to solve the puzzle or fix the problem. If everyone rolls perception and you hand them the answer, none of them feel the sense of accomplishment that triggers the dopamine.

I like to get as many characters involved as possible. Rather than jumping right to the Perception check I ask each player to tell me what their character is doing. A Ranger might want to look for tracks, the wizard sees through the familiars eyes, the thief might listen, the barbarian might just stomp off up the mountain. Let them all give you the actions that you can then weave together to give them the answer. Maybe the wizard does roll perception, but the ranger and thief have different skills. Use the rolls to make a story.

Perhaps the barbarian (who rolled a one) dislodges a stone higher up the hill that struck a boulder that emitted a hollow sound that the thief with his 19 heard. The ranger checks out that area and with his 17 sees some scorched stones and a drag mark that lead to the secret door. While they are searching the door, the familiar give warning that there are orcs approaching the barbarian.

I think of the dice as improv prompts, not yes/no answers.

Here's how I do it.

First step is to decide how hard the search should be; is this going to be a major part of your session or is it just a precursor to a bigger piece of plot or somewhere in between?

That informs:

a) The number of successful ability checks the party will need to amass in order to succeed in the larger goal (of finding the thing they are looking for)

b) The DC of the check

Pick some suitable skills for doing the search: perception and investigation are obvious ones; but depending on what they are looking for and the environment they are in; survival, nature, medicine, animal handling and arcana could also be relevant.

Come up with some ideas for the clues they might find when rolling specific skill checks - blood left behind by their quarry for a medicine or animal handling check; some invisible (to the naked eye) runes for an arcana check etc. (Feel free to come up with these on the fly if that's your thing, but I like to have at least a small bank of ideas prepped ahead of time)

Come up with some adverse events which could happen to the party while they are searching; perhaps they stumble into a hunters trap and need to escape (athletics/acrobatics checks or take damage), or maybe they disturb a giant wasps nest and end up in a combat.

To run it based on the above, you need to describe the scene to the party and ask what they do. Based on what they try decide on an appropriate skill check from your prepared list. If they succeed, describe the clue they found and ask what they do next. If they fail, pick an appropriate consequence and run it; once that's resolved, they can continue the search. Once they succeed a number of times equal to the previously decided number of successes they need; describe them finding the thing they were looking for.

If it's possible for the party to fail to find the thing you will also need to decide how many failures they are allowed before you inform them that their search is unsuccessful; you'll also need to decide what the consequences of that failure are.

If finding the thing is crucial to the plot and you don't want them stuck in a loop of fighting giant wasps over and over again until they succeed; throw in some extra encounters which can contribute bonus successes eg perhaps they come across an injured villager - providing any amount of healing (spell, potion or medicine check) to them allows the party to ask the villager for help in their search - perhaps they saw the thing the party seeks and can provide directions. This adds an additional success to the parties tally.

You can use this to effectively cap the number of checks that are required for the party to complete this section of your session.

There are many, many ways to play DND and there is no such thing as bad-wrong-fun. But with that said, DND still very much shows its war-gaming roots and it is stereotypically centered on fighting with the rules predominantly centered on fighting.

Sometimes having minor challenges along the way solved a simple roll so the party can get on with the fighting is not a bad thing. It is perfectly fine to roll perception. On success, the search is over and they can move on to the next part, which will often be a fight and to most parties will be more fun. This is quick and rewards players for optimizing and using skills their characters should have.

Obviously, if finding the thing is necessary for the plot to advance then failure cannot be permanent. But perhaps failure means they take so long that a random encounter happens in the meantime. Perhaps failure means they must camp for the night before trying again offering opportunities for attacks or other non-combat complications. Perhaps they encounter a trap or natural obstacle when they fail.

You can at least narratively enhance a search by asking the players exactly how they do it. This can help with adding complications if you want to.

In your particular case, one way they might search is the flying familiar. But that won't always be an option. If the flying familiar is a large bird, it probably can't meaningfully fly in a building, cavern, or similar enclosed area. It might even have a hard time flying in a heavily wooded area and the canopy might make flying above it unproductive.

Then they have to decide. Do they stay together to search but in a way that takes them more time which could lead to complications such as an enemy fleeing? Or do they split up, which might lead to a much smaller group being ambushed or ending up in peril? Are they in a situation that allows for a more creative search?

For that matter, even if they send out the familiar, the familiar might encounter its own obstacles.

Also, remember that the complication doesn't have to be a clear obstacle. Maybe they stumble over something and find things they weren't looking for such as valuables, a person in need of help, potential encounters they can charge into, or avoid. A complication could be an opportunity.

All of these things at least narratively add detail to the story and give you opportunities to add complications or challenges directly related to their choice if you want to.

What's your players' wishes?

There's many a way to play D&D. Hopefully, you've got a good idea of what your players want out of the game, as you ran a session 0 prior to the campaign to align everyone's expectations. If not... better late than never.

Some groups play D&D as a hack & slash. There may be some role play, of course, but it's not a detective game. A couple rolls, perhaps a reward for ingenuity (or inspiration) let them avoid spending too many resources ahead of time/corner the dragon in its cave rather than getting corner on the plain, and off to the big fight we go.

At the other end of the spectrum, you've got the detective games. Sometimes it's all about intrigue, diplomacy, with just a little bit of magic/fight thrown in. Think spy novel, like the James Bonds of old. Or it's detective games ala Mist/Monkey Island. Clues scattered around the place, with false leads mixed in, and the players having to reconstruct the truth from the pieces only to realize that the dragon was the very mayor who invited the party in in the first place.

If your group is more hack & slash, any protracted search will just bore them. If your group is more detective-y, a single roll will disappointed them.

You have to know what your group wishes for, to determine your goal with the search.

What's your goal with the search?

Is the search just a means to an end? As in, of course they need to go and fight that dragon, so they're going to search for the cave, find the cave, and then the real fun begins.

Is the search an opportunity? As in, of course they're going to fight the dragon, but they'd have a much better advantage in the cave -- where it can't really use its flight -- than in the open.

Is the search an attrition step? As in, of course they're going to fight the dragon, but how much resources will they have to expand prior to the fight will change how easy/hard the fight will be.

Is the search a quest of its own? As in, nobody's ever located that cave. And there's kobolds and wolves running amok on that mountain, and perhaps an owlbear. There's a few rumors of rangers looking to take down the dragon too, though, if you were to find them, they may be able to assist you in some way... Oh, and unbeknownst to the players, there's a cult looking to acquire a dragon heart for some ritual of theirs. Race on!

And from there you can determine the steps.

Perhaps it'll be a single roll, you'll get the heading, and off to the cave we go.

Perhaps it'll be a bit more "interactive". A good roll will allow the players to find a more direct path, to avoid obstacles/distractions, and arrive better rested, unseen, etc...

Perhaps it'll be a lot more difficult. There's many a cave in the mountains, so it's all great that the familiar spotted 5 of them already, but which is the dragon's? Maybe a bit of thinking would help narrow down the choices? The small one is surely too small. And isn't it tuft of furs next to that other one? Dragons don't have fur!

Perhaps it'll be a quest of its own. What do the locals say? Which side of the mountain has the dragon be spotted on? What does the wizard knows about this type of dragon: do they prefer low or high altitude? Small or large caves? Maybe an old crone would have some wisdom to share? Maybe the dragon can be baited then followed? Or is known to show up every few days from which point it can be followed? And in the meantime, what other dangers does the mountain present?

Really, the search itself can be just as intricate as you wish it to be. You can put arbitrary consequences (and thus opportunities to avoid them) on the way, depending how the players fare.

It all depends on your goal, which itself should depend on the type of campaign you agreed to run with your players.

Though... circling back... even if you agreed to a quick hack & slash a bit of searching would spice things up, and even if you agreed to a detective-y campaign, not everything has require days of investigations & preparation: perhaps the mystery starts with the dragon hoard, after all, so there's no need to make it too complicated.

Also... do know your players. Some groups have a tendency to overcomplicate everything. No need to make it too complex for them in the first place, then, they'll come up with their own obstacles.