Moneyball For Remote Hiring: Identifying Key Personality Traits That Predict Success For Remote Attorneys

Written By: Eric Fox, Director of People Analytics, Hire an Esquire

Before Cambridge Analytica and a Facebook data breach made personality profiling front page news— “moneyball” for Major League Baseball (MLB) and the National Football League (NFL) was proving the effectiveness and accuracy of industrial psychology-based personality testing. Both MLB and the NFL famously and successfully leveraged decades of outcomes-based research on personality testing to predict job performance.

The talent drafted or recruited by both professional sports teams and law firms largely determines their success.  Smaller law firms have less room for error in hiring than their larger counterparts with each new hire having a more significant impact on firm output and culture. Further, many modern, business-forward small firms are increasingly using a virtual office and remote work structure, adding another variable to the hiring equation.  Here’s a high-level overview of how small firms can leverage some of the insight and research available to the pros to create their own winning team.

About Personality Testing

In Industrial psychology, personality is measured through both “qualitative” and “quantitative” means. Personality inventories, surveys where job applicants are prompted to agree or disagree about themselves, are quantitative (e.g.  “I am good at making new workers feel welcome” and “I enjoy influencing other people,” align with extraversion).

Qualitative measures of personality are best gauged by asking candidates specifically framed questions about past experiences. How candidates frame and answer these open-ended questions provides key insight into their personality traits.  For extraversion, an interviewer would ask a candidate to “Describe a time you won over a client who was reluctant at first” and to detail the context of the situation, what they did, and the result.

Most commercially available personality tests measure and score general traits, providing little relevance and guidance to hiring for a specialized role.  And, often a consultant must interpret the results and apply them to a specific industry and role.

Our Method

I joined Hire an Esquire when the company was looking for a dynamic and scalable way to perfect an attorney’s “fit” for a role beyond the typical hiring and screening processes. These produce limited success rates in all industries and are highly subject to bias. Getting the exact fit, on demand, was of key importance with most of our roles being temporary and many being staffed with short (sometimes same day) timelines amidst an urgent deadline.

Since 2016, we’ve been developing and refining proprietary qualitative and quantitative personality assessments for our network based on traits and attributes shown to predict performance in the legal profession and specific roles within. These results combined with other predictors of performance such as references, reviews, skills, and background assist in gauging the roles and environments where an attorney will be most successful. The matches that instantly appear on Hire an Esquire when you post a job take into account an attorney’s strengths against the specific requirements of your role.

So that you can do your own qualitative assessment of potential remote candidates we’ve detailed key traits, extensively shown to predict performance when workers have a great deal of autonomy as do remote contract attorneys. We’ve also included sample questions and what to look for in a candidate’s answers.

Four Traits to Look for in Remote Workers:

1. Openness to experience: predictive of performance in ambiguous and self-directed situations. People high in openness are creative, adaptive, flexible, and enjoy independence.

Interview Question:

  • Describe a time where you had to deal with an urgent or unpredictable situation
  • Please give an example of a difficult change you experienced at work

What to look for in answers: The candidate took effective action without needing to know the total picture or all of the facts and imposed structure (for self and others) to focus the situation.

Potential Flags: Paralysis and/ or a negative view of the uncertainty or ambiguity, extending deadlines or looking to others to find and execute the solution to difficult obstacles.

2. Proactivity: involves scanning the environment for opportunities and acting upon them. Self-starters and continuous learners are high in proactivity.

Interview Questions:

  • Describe a time when you took initiative to get something done at work
  • Tell me about a time you had to update your skill set to perform effectively

What to look for in answers: A clear understanding of spotting an opportunity and the implications prompting action, anticipating changes in work demands and acting upon them before being prompted or before it was necessary.

Potential Flags: The candidate only took action when prompted, the passing off of new duties to others,  not adjusting their own methods.

3. Conscientiousness: a universal predictor of job performance. People who are conscientious are planful, organized, disciplined, and consistent. For remote contract roles, they excel in efficiently prioritizing work and ensuring deadlines are met.

Interview Questions:

  • Please give an example of exceeding an agreed upon standard
  • Tell me about a time when you have had to organize a significant work project

What to look for in answers: The candidate should have shown a great deal of effort and persistence in completing their work.

Potential Flags: The candidate did not display a methodical or persistent approach.

4. Agreeableness: interpersonal sensitivity, compassion, and politeness. People who are high in agreeableness are modest, sympathetic, and compliant. Because the trait emphasizes working with others, it may seem counter-intuitive to predict performance while working alone. However, studies have shown that because people high in agreeableness are more compliant, they show greater intensity in following rules and urgency in making deadlines.

Interview Questions:

  • Give an example of when you had to manage a difficult relationship at work
  • Describe a situation where you gave time to help others who had work-related problems

What to look for in answers: The candidate showed a high sensitivity towards the interest of others, uncovered what made them tick and therefore found common ground to resolve issues.

Potential Flags: The candidate passively accepts the situation and any difficulties associated with it. Answers that indicate the situation was handled with aggressiveness or arrogance.


Are you considering a remote hire for your next legal role? Download Hire an Esquire’s free infographic to learn the four primary reasons you should be.



Judge, T. A., & Zapata, C. P. (2015). The person-situation debate revisited: Effect of situation strength and trait activation on the validity of the Big Five personality traits in predicting job performance. Academy of Management Journal, 58(4), 1149-1179.

Major, D. A., Turner, J. E., & Fletcher, T. D. (2006). Linking proactive personality and the Big Five to motivation to learn and development activity. Journal of applied psychology, 91(4), 927.

Author Bio:

Eric Fox is the Director of People Analytics at Hire an Esquire, and an alumni of Baruch’s Industrial-Organizational Psychology graduate program, where he studied predictive analytics and personnel selection under Harold Goldstein and Charles Scherbaum, the creators of the NFL player assessment test. Utilizing the methodology from his teachers, he applied these concepts to the practice of law to predict attorney success.

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