Hiring Lessons From Annie Duke: World Series Poker Champ

A version of this article previously appeared in Forbes.

Earlier this year, I had the pleasure to hear Kit Cooper interview World Series of Poker champion Annie Duke. Annie touched upon a number of compelling topics covered in her latest book Thinking In Bets (published Feb, 2018), including how she provokes job candidates to show their true colors during interviews so she can read their “tells.”

It is clear that Annie enjoys interviewing candidates, a role in which she makes people uncomfortable in order to peek into their souls.

Find The Tells

The seasoned executives Annie interviews have well-rehearsed responses to the trope of conventional interview questions. Thus, little insight is gained from obvious and expected questions that do not pierce these seasoned applicants’ veneer.

To counter the polished sophistication of the folks she is interviewing, Annie sets the tone by throwing the candidate off balance. For instance, she might ask, “Was there traffic? Why are you late?” or “You’re early, but that’s ok.” despite the fact that the candidate is on time.

Her intent is to put the candidate on their heels at the outset and see how they deal with the mild stress that comes from someone not following the normal social conventions of polite conversations.

She then asks questions that have no answer to see how the applicant responds to ambiguity. According to Annie, “I’ll ask them morality questions to make them show true emotions. Things like the trolley dilemma.” Like a Buddhist Kōan, the respondent’s thought process matters more than their answer. This approach also allows Annie to assess the candidate’s demeanor and attitude while they struggle to find the right answer.

Typically, the candidates report back to the potential employer that the interview was a negative experience. In some cases, Annie’s clients express dismay that she would treat a senior executive candidate in such an off-putting fashion.

However, everything changes when Annie then tells the employer, “I thought they did an excellent job. You should hire them.” When Annie shares the insights she gained by opening up a window into the candidate’s soul, the employer’s attitude changes. Suddenly the logic underlying Annie’s unconventional approach becomes apparent

When previously miffed candidates are told that they received Annie’s stamp of approval, they typically rewrite history and describe the experience as challenging but rewarding. Annie concluded by noting that once these interviewees accept the job, they feel like they have joined an “exclusive club.”

Find Their Inner Child

Similar to Annie, during my days as an entrepreneurial executive, I attempted to understand who the candidate was when they graduated high school, in order to assess who they are as an adult.

I would ask myself, “Am I speaking with a shy boy who spent his High School years writing in his journal or a boisterous verbal bully who used her wit to hide her insecurities?” The characteristics I assessed to determine who the candidate was included: creativity, risk profile, curiosity and desire to win.

Although I wasn’t as sophisticated as Annie in my approach, I also relied on non-typical questions designed to determine who the candidate really was, such as:

• Did you move around a lot as a kid? If so, did you enjoy relocating?
• What were your parents’ greatest personality failings? <children often overcompensate to avoid what they perceive as their parents’ shortcomings>
• How many siblings do you have? Are you the youngest, oldest, middle child?
• What was your nickname growing up? If you could have picked a nickname for yourself in High School, what would it have been?
• What were your parent’s aspirations? Which of their dreams remained unfulfilled and why?
• Did you become proficient on a musical instrument? Do you still play?
• When you were in fourth grade, what was your dream occupation?
• Who was your favorite teaching in High School? What caused you to remember them so fondly all these years later?

Most of my hiring was done in a startup environment. Thus, a candidate’s willingness to share whom they really were helped me understand how well they would fit in with our startup family, where everyone worked in close quarters and on multidisciplinary teams.

Insight In Numbers

I also found that group interviews can also be an effective way to gain insight into someone’s soul. In one-on-one interviews, the applicant is always on. They maintain eye contact; smile at the right times, say what they think you want to hear and generally make a concerted effort to keep you from knowing what they are thinking.

In group interviews, maintaining an unflappable facade is more difficult, as the interviewers who are not in the midst of asking a question have the luxury of observing the applicant. Top negotiators often prefer to work in teams so that one team member can observe body language, devise questions, take notes and analyze the applicant’s responses, while the other interviewer is engaged in conversation. You can gain similar observational insights through group interviews.

Changing the environment is also an effective way to encourage someone to speak more openly about who they are, as opposed to the traditional discussion over a desk. Go on a walk, head out for coffee; anything that breaks the interviewing norm will help you better assess the candidate’s suitability.

Job Hunting With A Rifle Or Shotgun?

I always asked candidates to describe the other companies they were targeting in their job search. This will gave me insight into the applicant’s true career goals — if my company was the only startup on their list, it caused me concern that they may actually be more comfortable at a large company. This question also helped me sell the benefits of the position I was filling, by allowing me to more effectively sell against the applicant’s other job opportunities.

Negative Selling

Another tactic I used to determine a candidate’s entrepreneurial inclinations was negative selling. For instance, I might say, “You certainly have a great skill set, but I am not sure we can afford you.” This sets up your future salary negotiations and gives the candidate a chance to reach for the opportunity, by explaining why they are an ideal fit for the position. If they aren’t genuinely motivated to work on your team, it will be obvious in their response.

Free Consulting

I also assigned promising candidates meaningful homework during the recruiting process and before making a job offer. For instance, I might ask them to research a potential new market, analyze a competitor or assess a new distribution channel. I always selected tasks that added value to my company’s efforts and avoided, bogus, make-work projects.

There are several potential positive outcomes from this approach: (i) free consulting, (ii) the candidate becomes engaged in your business and thus can hit the ground running once hired, and most importantly, (iii) it results in a work product by which you can judge their abilities. Prospective employees who are unwilling to engage in such assignments might be a poor fit for a high-energy environment.

Try Before You Buy

One of my investments, TaxJar, effectively utilizes trial periods as a recruiting technique. Such trials are mutual. If it is apparent that the relationship is not working, the potential employee can move onto a more appropriate opportunity, without the emotional pain associated with departing a full-time gig.

You can follow John on Twitter: @johngreathouse. You can also check out his hands-on startup blog HERE.

Image credit: John Greathouse