What is your biggest challenge? 

This sounds like a very good question to pose to your employees, whether they are working in your customer service department, prepress, accounting. It sounds good because it expresses care and concern. I agree that it’s a good question if you want to express care and concern—but I don’t think it’s a good question to ask if you want to really understand what YOU could do to best improve the daily work life and productivity of your employees.

An employee sees your business from their unique point of view, and by design. You are looking at your business from a very different perspective. The best way to figure out what your employees’ challenges really are is to observe them in their daily workflow(s). The word “observe” is important here. Do not ask your employees to describe what they do in a conference room. Go to their workspace and observe; do not interject, try not to impact the situation, only observe it. This is where you will find gold in the form of people doing things the way they’ve been doing things using the tools they know how to use for years.