It is rare in a game of Dungeons & Dragons that you’re not attempting to succeed at a goal. There may be odd encounters which are unexpected, but typically your party is working towards something, either self-generated or a task given by others.

It helps to agree on what that goal is!

Even an expedition into a megadungeon typically has a goal, such as these: Find the entrance to the next level. Find the best treasure and take it! Find where the dragon lives!

Work out what that goal is and if there are any secondary goals you’re trying to attempt.

Then, determine how you might accomplish that goal. Can you research the layout of the area? Find out who might be there?

Here’s a few things to think about:

• Where are we going and what’s the layout?
• Who will be there to oppose us? Will anyone be friendly?
• What are we trying to accomplish? What part of that should we do first? (Can it be broken into smaller tasks?)
• What does each of us bring to the table? Are there individual tasks we should do?
• What do we do if something goes wrong?

That last is quite important. Plans go wrong, and they can go so wrong that your characters all perish in the attempt! This is less likely if you’ve got a plan for escaping – and you can identify that now’s the time to use it!

Here’s one final thing to make planning easier:

Ask your Dungeon Master if your plan sounds reasonable.

Most DMs – at least, I hope it’s most – are more than happy to look over your plan and point out things that don’t work, often because they’re based on something you don’t know but your character does. If you’re playing a soldier, your character probably knows the layout of typical forts, even if you (the player) doesn’t.

Ask your Dungeon Master about things you’re not sure of. If the DM told you something earlier and you can’t remember it, ask the DM to repeat it! (Also, make notes! Discuss them with your friends!)

This is all in the preparation stage. Do the work then and you won’t have to worry so much about improvising once you reach the adventure.

Also, as suggested by Steve Kenson: It helps for the DM to repeat the plan back to the players, just in case the DM has misinterpreted something. (I’ve seen this happen – where the players have a very reasonable plan, but it goes wrong because the DM thought something else was happening).

Once the adventure actually begins, the DM is unlikely to be so helpful, because by then they’re trying to run the opposition. Yes, they likely want you to succeed (though challenged), but it’s difficult to both offer advice and run the enemies at the same time.

However, if you’re really stuck, ask your DM if they can give you some suggestions.

Plans are unlikely to go as you expect – that’s the fun of the game – but if you have one, then at least you and your friends do have an idea as to what’s going on, and ideas on how to recover when things go off the rails!