The One Question That Will Expose a Person’s True Character

Danielle West
The Startup
Published in
4 min readJan 7, 2021
Image by Erik Lucatero from Pixabay

As the year begins our social media feed is full of triumphs from the previous year and new year resolutions that are often conveniently forgotten within the first three months of the year. Why are we so bad at staying focused on these goals? One reason for this may be down to the way that our brains work.

Cognitive or unconscious brain biases such as illusory superiority and the Dunning-Kruger effect enable many to conveniently ignore flaws and overemphasize their abilities. The former tends to do this in comparison with others; this is where we tend to feel quite smug as we scroll through social media or believe we are better drivers on roads where everyone is trying to navigate their best with the help of Google Maps. The latter is often preceded by “Hold my beer…” and goes on to populate the Darwin Awards. Although these biases can prevent us from falling into a hopeless pit of despair around our true abilities, they also can impede our growth by keeping us in a fictional comfort zone. The best way to combat this delusional stagnation is to look unflinchingly at our own failures which is about as fun as getting a root canal.

Examining our failures has become fashionable to the point of cliché with various Ted Talks and even the Michael Jordan documentary the Last Dance, yet we still find it difficult to examine our own shortcomings despite posting countless quotes on social media or spouting platitudes to long suffering friends, family or colleagues. We are continuously inspired by the mistakes and subsequent learnings of others but struggle to admit to our own. How can any of us hope to learn from our mistakes if we refuse to acknowledge them in the first place?

Image by www_slon_pics from Pixabay

When I interview candidates for my team, I always ask two questions to ensure a growth mindset and collaborative team culture. The first question is:

How have you failed?

For me, this question is far more telling than your experience, GPA or LinkedIn profile. I already know what your achievements and strengths are since they are listed in your CV, but I want to know how you frame failure. Do you take responsibility for your failures to learn from them and grow as an individual? Do you blame others for your mistakes? Or worse, does the question trigger you and send you into a defensive spiral of denial? How you respond will give me a sense of how you perform under pressure and within a team. As a manager, I want my team to work collaboratively in a safe environment where people feel comfortable in admitting to mistakes so that they can go on to succeed. This is how growth works. If you aren’t able to admit to a mistake, how likely are you to repeat it?

This question not only works for job interviews but also for dates, screening business partners, baby sitters, dog walkers or anyone who you are bringing into your circle of trust. The way someone responds to this question gives you a good sense of how they respond to adversity and also how honest they are with you as well as themselves.

Image by Adabara Ibrahim from Pixabay

The second question I ask is:

How do you feel about telling your manager that they’re wrong?

This question is related to the first as it demonstrates the candidate’s ability to point out a senior teammate’s failure. Authority bias is great for managers that favor yes men or sycophants but can actually be quite devastating as demonstrated by the Challenger Space Shuttle and the Avianca 52 flight. Failure and error are inevitable for everyone, including authority figures.

Image by FelixMittermeier from Pixabay

As a manager I need the team to feel comfortable with telling me where I have failed, preferably before the misstep actually occurs. Ideally this will be told along with possible solutions along with data or evidence to support their theory of potential disaster as well. And when I ask candidates this question it reminds me that, I too fail and that in these failures I learn and improve with the help of a good team.

It is critical to understand that our failures do not define us but how we respond to them is indicative of our character. And in these reflections we find the tools that we need to succeed are earned in the trenches of adversity rather than handed to us on platter in our comfort zones.

“You cannot measure a man by his failures. You must know what use he makes of them. What did they mean to him. What did he get out of them.”

-Orison Swett Marden

Thanks for reading. You can also find a link to the audio for this article on Anchor or Spotify.

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