GM Tips: The Inmates are Running the Asylum - PCs as Settlement Leaders

As a player, the best tabletop roleplaying gaming experience I’ve ever had was my first play-through of Lost Mines of Phandelver. After routing the Redbrands from their stronghold, my Dragonborn Eldritch Knight, Hilmark, through a series of calculated power moves and deeds that benefitted the frontier town, eventually became mayor of Phandalin. Becoming the leader of the town was clearly not part of the 64-page module, it was not something the DM had planned, it wasn’t something the other players had encouraged. It was simply what Hilmark had wanted and I had helped make happen. The only thing more fulfilling than winning the throne of Phandalin was running the up-and-coming frontier town. Having now been on both the player and GM side of the party taking a leadership role in a settlement (and on the game design side with Organic Towns), here are my best tips for making the most of it.
Roleplay Public Perception - Throngs of commonfolk gather outside the castle to protest an unpopular war against the woodland gnoll clans. Merchant line up in the throne room to plead their case for restoring a long-inaccessible bridge. Dwarves cheer and toss rose petals onto the road in front of the party, thrilled over the profitable expansion of a silver mine. As a GM, one of the best things you can do to make a party-ruled settlement feel real is to roleplay citizens to show what they think of the party’s decision. Doing this through roleplaying rather than exposition will make their decisions feel much more consequential.
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Trouble in Paradise - There has never been a human settlement on this planet where everyone agreed that things were going well - and that definitely shouldn’t be the case for your player-run settlement. Thing about 2-3 issues that are important to the settlement that residents are either stressed about or argue with each other about at the tavern. Are they worried about rust monsters destroying difficult-to-obtain farm equipment? Are they upset over taxes or do they argue about whether improved roads or a new harbor should take priority? Determining what these issues are will help guide what problems you are presenting to the party that they must solve.
Utilize Advisors - When presenting settlement problems to the player leaders, one way to go about it is to have residents approach the party - perhaps during public hours at the town hall. This can work well because this allows you to present issues via roleplay rather than exposition. However, I think a better way is to present settlement problems in something akin to a small council meeting. Create 2-3 NPCs to advise the players, all representing different interests. You can then roleplay discussions between the advisers which (unlike the public townhall version) let’s the party hear two sides to the issue at hand. For example, if there’s demand in the settlement to lower taxes, an advisor can advocate for each side. public approval and happiness vs affording a military expansion and a bridge repair. This strategy will make their decisions feel consequential and like there are no good choices. As GM, this is the most you can hope to achieve.
Consequences - As the player leader make decisions on behalf of the settlement, it’s important to show the consequences of their actions - good or bad. If they raise taxes, show disgruntled citizens and laborers constructing new buildings. If the party bans brothels, show about appreciative conservative temple worshippers and a sudden uptick in crime as brothel workers seek to make money elsewhere. The last thing you want is for players to make what feels like a difficult decision and then they see no repercussions from the town one way or another.
What's your best tip for making the most of player-run settlements? Let me know in the comments below!
-Shane