Start with how the person actually works.
If they're regularly traveling or moving between locations, something useful on the go makes sense. If their coffee mug is permanently attached to their desk, you already have a clue. If they live in graphic T-shirts and hoodies, look for a design with a message that sounds like them.
Then think about what part of business they identify with.
Sales. Execution. Persistence. Preparation. Building something from scratch. Pursuing the next opportunity.
A message about closing deals could be perfect for one person and completely wrong for another. The same applies to a bold motivational design.
The closer the product and message fit the person, the less generic the choice feels.
You don't need a list of 50 ideas. You need to know who you're buying for.