The challenges you’ll find in any organization come in two flavors:

Type 1 Challenges often sound like restatements of the organization’s overall mission, and employees will openly acknowledge them often. For example, a software company trying to build a better web browser may cite technology barriers as a major challenge. These are obvious, and you may be working on some of these challenges as part of your core responsibilities. Don’t stop digging here.

Type 2 Challenges are the real deal, and you won’t hear about them during the interview process. A Type 2 Challenge for the software company above might be, “We have zero brand recognition and don’t know how to market our products.” That’s a much scarier problem for the future of the business than some technological hurdle. These are the kinds of things you need to be on the lookout for...