Whatever you choose to ask the person interviewing you for a job, make sure to take note of one thing: Whether they offer any downsides to working at the company.
Every job features pluses and minuses. You might work with brilliant people, for example, but on a shoestring budget. Or you might have millions of dollars’ worth of resources, but the infrastructure you manage sprawls across multiple offices. The company as a whole might have problems breaking into mobile with a successful app, or aligning all its divisions to tackle some massive strategic issue. There are infinite possibilities.
If your interviewer avoids talking about any downsides—or refuses to acknowledge there are challenges at all—that’s a potential warning flag. It hints at a corporate-wide issue with transparency, and perhaps even a dangerous blindness to internal faults.
Corporate downsides, of course, aren’t a bad thing—it’s just a question of whether you regard the particular company’s as interesting challenges, or whether it’s a potential deal-breaker. A company that faces strategic issues, such as trying to pivot in an aggressive market, offers lots of opportunities for an ambitious tech pro to leave his or her mark. But if the downsides don’t seem surmountable—for example, the company refuses to stop using an antiquated technology stack—then it might not be the position for you.