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If a UX director asks this question, he wants to see how much of real UX designer you are, and how methodical you approach this task. A good UX designer needs to understand the real problem first. Based on the information given we can only make broad assumptions. A hypothesis based on limited data is a good starting point, but before we jump to premature "solutions", the first task is to do more digging. We need to ask questions (and do research) to understand the actual problem before we can propose a a fitting solution - a user experience that truly solves the unique problem these four people have in their specific situation (it might even turn out that they don't need to cross a bridge at night but need something completely else, but let's not go that far here). So - based on the information given, we don't know what type of bridge it is (does it have a railing, is the bridge lit, short, long, is there even pavement or gravel and potholes, is there traffic, etc...), we need to understand WHY only one person can walk on the bridge and whether the people even need to walk (they might be able to drive, maybe there is a bus that can transport them). Where is the flash light, what type of flash light is it And who are these individuals? What is the relationship between these people? Do they all have the same motivation to cross the bridge? WHY do they need to cross the bridge? Is that really what they need, or do they have a different problem? Also, are they all on the same side? Why do they need to cross the bridge at night, do they have to cross the bridge every night or just once? Etc. etc. -You get the point. In addition: What are my resources to get them over the bridge? Which technical and business opportunities and constraints do I have? In which time duration do I have to get them cross the bridge? Fun exercise for a UX candidate. Minder