“I try to climb the wall … that’s an 8.”
“Nope. You try, but you can’t find enough of a grip to actually get far.”
“I try again!!”
The way I look at scenarios like these is a two-step process.
First, if there’s no in-game reason why the party can’t just ram their head against something until it works, just let it work. If there’s no real reason they can’t just keep running into a closed door until it eventually breaks, let that happen, no roll needed. But if there’s maybe someone on the other side, or someone who might hear, or something else in the world that you know of that makes time an issue, that’s when the rolls happen.
Next, whatever roll happens represents the party’s best effort at doing that specific thing in that way, at that particular approach to the issue. (Side benefit: the party strategizes and uses the best person for the job.)
By all means, try again … but do something different the next time around.
Easy and simple, and you’ll never end up going around the table with each player rolling until the thing finally works.
Also … I’m publishing a new adventure tomorrow, Silent Screechers! It’s a short jungle island one-shot for 5th level, and I’m super excited to hear folks’ stories about how it goes at their tables! I even got it professionally laid out and it looks phenomenal (queue double excitement from me). I’ll send you an email when it drops, and I’ll link to it for a few days in the regular roundup. I don’t have a Patreon or anything like that, but if you’d like to support the work I do (and want a fun adventure to boot), I’d appreciate checking it out!
Subclasses, Part 3 – Wizards of the Coast
Setting Up a Marching Order in D&D 5e – Dungeon Solvers
The Grendleroot in Avernus – Sly Flourish
The Sapphire Dragon is available now on D&D Beyond – @DnDBeyond
AL Campaign Rules Update | February 2020 – Adventurers League
How to Play an Archfey in D&D – RJD20
Designing One-On-One Adventures – Norse DM
The Value of Traps and How to Use Them in D&D 5e – Dungeon Solvers
Wisdom Under Fire: An Australian Charity Adventure [BUNDLE] – DMsGuild – $22.42
Scientific Secrets of Saltmarsh – DMsGuild – $6.95
100 Temperate Wilderness Locations – DTRPG – $1.99
Now get out there and tell a story!