I was having a conversation recently with a client who was asking my advice on interviewing for a key position on her staff, and it made me think of an unstructured conversation.

She asked me how to know during an interview whether you can truly trust a person to deliver what you need in the role.

What I often find is that interviewers will ask a series of questions about all kinds of things to get at skills, behaviors, problem solving, attitude, motivation, but they fail to ask the one most important question.

What is “THE” critical interview question?

First you have to think about what it is you really want to know. 

In this case it was how do you know if you can trust a creative person to deliver if they are not accustomed to tight project management on their work? 

This came up because I mentioned that sometimes you need to manage people differently to get the best motivation and results from them, and that judging a creative person on how effectively they manage projects might not get you the most creative person!

Any in this case, the one key question is to ask the thing you really care about directly:

Give me an example about how you worked on a large project and describe your preferred way of managing your work and finishing on time? Why does that work for you?”

This is exactly what you want to know about, so why not just have a conversation about this most important thing?

It helps to have an unstructured conversation

This got me thinking about this idea I always talk about, which is how an unstructured conversation, while it might feel messy and uncontrolled in the moment, is where all the magic is.

It’s how you find out just what people really think.

A great many business leaders avoid unstructured conversations because they find it threatening to hear what people really think. After all, they just might disagree with you, or doubt the things that you think are important.

But, and this is particularly true in an interview, wouldn’t you rather know?

When an interview becomes a good conversation

Many times interviews are very structured conversations. You get a bunch of information, but little insight about how the person really thinks or works, or what they truly care about.

But if you are willing to have a real, authentic, unstructured conversation with a person, you will get to know what you can expect from them on a much more useful level for making a hiring decision.

Here are some questions that might help to open up an unstructured conversation in an interview:

  • Here is our current strategy, what do you think? And why?
  • When you had your most challenging job, what was hard about it? And why?
  • When you think of a success you had, what was it that made you most proud? And why?
  • When you are having a bad hair day and feeling unmotivated, what do you think about? What do you do? And why? Can you give me an example?
  • When you determine that there is risk in a project you are working on, what do you think about? What do you do? and why? Can you give me an example?

This is important: Don’t miss out on the best information thinking that an interview needs to be a rigid process. Think about what you truly want to know from this person and then be willing to just talk about it!

Patty Azzarello

Patty Azzarello is an executive, best-selling author, speaker and CEO/Business Advisor. She became the youngest general manager at HP at the age of 33, ran a billion dollar software business at 35 and became a CEO for the first time at 38 (all without turning into a self-centered, miserable jerk). Patty is also the founder of the Azzarello Group, which works with CEOs and leadership teams to help their businesses (and people) get better at what they do. She is the author of the best selling books: RISE: 3 Practical Steps to Advancing Your Career, Standing Out as a Leader (and Liking Your Life), and MOVE: How Decisive Leaders Execute Strategy Despite Obstacles, Setbacks, and Stalls. Follow Patty on Twitter @pattyazzarello or connect with her on LinkedIn.