Through the years, I've been on both sides of the interviewing table. When I've been the interviewer, I wanted to find the best ways to not only get a handle on a candidate's real experience and skills but also to get a window into his or her personal make-up, especially for management roles.

Even though interviewing is a flawed process in many ways, it is still the way it's done. There are a lot of strategies for how to be a good interviewer as well as how to be prepared to be interviewed and answer the hard questions.

For better or for worse, there is one question that seems to have stood the test of time:

"What's your biggest weakness?"

Early in my career, I feared this question. As an interviewee, I was scared that I might expose some huge gaps about myself that would take me out of consideration for the job. As an interviewer, though, I've found that I like it more and more because it gives me a window into someone's self-awareness, humility, and willingness to keep it real.

Most of us are answering it the wrong way but thinking we are outsmarting the question.

Early in my career, I received coaching about how to deal with this difficult question. In essence, I was coached to take an actual strength but cleverly disguise it as a weakness. That coaching might sound very familiar because it is really prevalent out there.

Underlying that coaching, though, is the flawed perception that you are not allowed to show real weaknesses, gaps, or development areas, and that any acknowledgement of these will immediately disqualify you.

Last time I checked, I have a laundry list of weaknesses (my wife and kids would be happy to be cited as references here). Those weaknesses haven't gotten in the way of my success all the way up to high leadership levels. I don't think I've been faking people out for all these years.

Your "weakness-proof" answer doesn't help an interviewer really get to know you.

Here are some real answers I've gotten when I've asked this question:

"I'm a perfectionist. I just want things to be really great so I'll work tirelessly to get it exactly right. That's a weakness I'm working on."

"I work too hard and can be too dedicated."

"I just care too much."

Those responses may even sound familiar.

I certainly can't always claim to have made the best decisions or have used the best judgment (weaknesses I'm working on just to be transparent and self-aware), but I don't remember the last time I told a candidate that I couldn't in good faith hire someone who was going to be too dedicated or work too hard.

Or tell them that I just wasn't looking to hire people who cared a lot, much preferring to bring on people who didn't care one way or the other as long as they got paid at the end of the week.

What do you have to lose if you take a risk and answer the question with a real weakness?

Ironically, I have found that some of my best hires have been the people who have been really honest about what they don't know, what experiences they haven't had, or challenges they have experienced where the outcome wasn't everything they had hoped it would be. That's real.

I interviewed a young manager years ago who told me that he was really bad at dealing with conflict, especially when it came to performance challenges with his team because he wanted everyone to be inspired and excited about their work.

I hired him because he had a lot of other great things going for him and had the self-awareness and managerial courage to be open about something he needed to work on. It also helped both of us manage expectations and build the right development plan for him when he joined.

So maybe the next time you get asked the hard question about your weaknesses, give a real one.

You obviously don't want to depict yourself as a walking buffoon, but take a risk and talk about something real. You might find that a savvy interviewer will be happy to hear it.

Published on: Apr 19, 2017