Q: How can you tell if someone has the ability to handle ambiguity?

A: During negotiations class tonight, I had my class do a cross-cultural negotiation in which norms and customs were not fully understood by one party.

The key takeaway from the case was this: ambiguity does not always look gray. Quite often, ambiguous situations look pretty darn black-and-white! It’s only after you’ve taken the time to explore another perspective that some of the nuance starts to appear.

Given this, one can imagine how challenging a strategic (and politically sensitive!) leadership role can be for someone who consistently misses the nuance of a situation… the leader who is a bull in a china shop cannot help but leave a wake a wreckage!

I thought I would follow up on my posts about ambiguity and hiring lousy people with a note on how to assess one’s ability to handle ambiguity…

Here are three quick ideas for your interview process:

1. Start by not explaining the interview process, and watch what the candidate does. Does she immediately seek clarity? Does she get nervous? Does she jump right in with both feet, without asking anything? Or does she move forward carefully, occasionally probing, until she gets a feel for what’s going on and can take charge?

2. Ask open ended questions; similar to leaving the process itself vague, leave your questions vague. Does he provide a short, terse response and then wait silently for more prompting? Does he launch into a confusing, jumbled story? Does he start strong but then get lost in the “middle” of what he was saying? Or is he able to provide a high level framework for his answer, and then take you along for the ride all the way to a sensible conclusion?

3. Ask about the best and worst bosses she ever worked for. Did she prefer the boss who provided her lots of structure or who gave her opportunity and resources? Does she look back and appreciate a boss’ style in hindsight, or does she hold fast to her original opinions?

Of course, there are other questions you can ask in the same vein as these. Also, no single question will provide a definitive answer. But by paying attention to how the candidate structures his or her responses over time, trends will start to appear, and these trends can provide excellent insight into how this person will likely respond to job-related ambiguity, whether stemming from cultural subtleties, political sensitivities, or strategic uncertainties.

These suggestions may seem simple, but wielded appropriately, they will yield a wealth of useful information!

Jason Seiden is Co-founder and CEO of Ajax Social Media, a training company that shows professionals how use social media to work more effectively.