Here is my iterative concepting process of how I got to the final design of "the Conductor". The Conductor is the manifestation of death itself, in my team's game concept for our project at Breda University of Applied Sciences.
In our game, which takes place in the Mexican Revolution in the early 1900's, the playable character has died and wakes up on a train to the afterlife. On this track, the train stops at the 5 Stations of Grief where the player needs to complete a set of tasks to help his fellow passengers, and to help himself get to terms with his own demise.
The Conductor is the embodiment of death in this game's narrative. The Grim Reaper of this world. They control the train the characters find themselves on, but isn't necessarily an antagonistic force. They might be unsettling, but simply spectate in dark amusement and gives the player cryptic hints.
I like to iterate as widely as possible, and slowly narrowing down depending on feedback, when concepting for characters. I worked in rounds, asking for the opinions of my team every time and continuing with what gets the most positive feedback. Working on this character was satisfying, because I feel like I was able to properly go through the iteration process.
( For the image where I had overpainted the conductor into a 3D block-out, that block-out was made by https://maarten_samson.artstation.com/ )

The conductor in context. (3D block-out used for overpaint by https://maarten_samson.artstation.com/ )