Technical Recruiting and Hiring

Hiring for Conscientiousness

Why startups should hire conscientious people—and how to find them
Ozzie Osman (Monarch Money)
▪︎ 28 minutes read time

Thinking things through

Photo by Ümit Bulut on Unsplash

This post is part of a series of invited writings that give a personal perspective on the challenges of technical recruiting and hiring.

What might a shift supervisor in a factory outside of Cairo, a nurse at Stanford Hospital, and a software engineer have in common?

Before we delve into that: some background. As I was helping write the Holloway Guide to Technical Recruiting and Hiring, I had a chance to interview some of the best engineering leaders in Silicon Valley. I realized that most of them had a unique “theory of hiring”—some “secret ingredient” that they looked for when hiring and building teams that had helped fuel their success.

After a bit of self-reflection, I realized that I had developed my own implicit theory of hiring, and that the one trait I prized above all else was conscientiousness. Here’s how I got there and why.

Finding Dhameer

I’ve spent most of my career in tech (particularly, building software for consumer products), but I had a bit of a detour at one point. I spent a couple of years helping out with my family business in construction manufacturing, spending most of my time handling operations at a precast concrete factory in the industrial city of Helwan outside of Cairo, Egypt.

Management in the manufacturing industry (especially in a country like Egypt) is very different from management in the software industry. The work is a lot less intellectual and a lot more physical. Some of the work at a factory requires a high degree of skill, but it’s usually less about thinking and more about doing—welding, operation/maintenance/repair of equipment, that kind of thing.

A lot of management theory would predict that for these types of more routine, well-defined tasks, rather than inspire employees and give them autonomy, managers should simply use rewards and punishments.* And that’s how that factory worked: people were told what to do, monitored, and given bonuses if they did it well or a docked paycheck if they didn’t (imagine docking a software engineer’s paycheck if they introduced a bug!). Everything was designed around extrinsic, rather than intrinsic, motivation.

So imagine my surprise when I met El-Hajj Yasseen, one of the workshop supervisors. Yasseen showed up early and didn’t leave until his work and his team’s work were done. His shift consistently produced better quality than the other supervisors. If there was a problem, he was on top of it. Other supervisors would bark instructions and threats at their team to get things done. Yasseen’s team was much more organized, and if something wasn’t getting done, he would just do it himself. Yasseen worked hard and he cared about his work. In Arabic, we would say Yasseen had Dhameer—“a conscience.”

I knew Yasseen years ago, but thought of him recently when my family had to spend a few nights in a hospital’s ICU while a loved one recovered from a lung-related condition. Every twelve hours, a hospital shift change would occur, and we would have a group of medical staff helping take care of our loved one. The staff included physicians (residents, fellows, and attendings), with whom we’d have brief interactions, in frequencies inversely proportional to their seniority. But the people we spent the most time with were the hospital nurses.

When a new shift started, within just a few moments of a nurse entering our room, my wife and I could tell how this shift was going to go. Let’s take Sabrina. Sabrina checked on her patients regularly. She handled their needs delicately. She talked tenderly to them and to their loved ones, and went above and beyond to make sure that everyone was as physically and emotionally comfortable as possible. Sabrina cared. Sabrina had Dhameer. After Sabrina’s shift, my wife and I appreciated and admired her so much that we were left questioning our own career choices. Should we have worked in the medical industry? The character with which she worked inspired us.

On the other hand, Amy (let’s call her) was almost robotic. She had a checklist of things to do, vitals to check, and that is exactly what she did. If we needed something or had questions, we’d usually have to ask Amy two or three times, potentially risking what appeared to be an eye roll. It’s possible Amy was just having a bad day, but it definitely didn’t seem like Amy cared. We all (even Amy) seemed to breathe a sigh of relief when her shift ended.

What makes people like Yasseen and Sabrina different from people like Amy? Bringing a conscience to your work means working conscientiously—as Dr. George Simon put it, “Conscientiousness is mindfulness guided by conscience.”* Conscientious people have a desire to do good work, and are self-motivated to perform well regardless of whether someone is watching over them. They are action-oriented, dutiful, and careful. This might sound like a vague catch-all for a bunch of positive behavior, but it’s actually a “big five” personality trait that many people believe is ingrained, hard to change, and testable.

Conscientious, ambitious, or insecure?

Is anyone who works hard conscientious? Before zeroing in on conscientiousness as a hiring trait, I used to look for people who had high intrinsic motivation, or internal drive. I’ve since learned that internal drive can come from several different sources, and though from a distance these types of drive may appear similar, in reality, it’s worth distinguishing them.

One type of drive comes from personal ambition. Ambitious individuals, like conscientious people, work hard and aim for impact and achievement. The difference is that ambition tends to be ego-driven. Ambition works well as long as a person’s individual success is tied to their team or company. But, given the choice, ambitious individuals will do what benefits them personally. They may engage in workplace politics. They might bail on their team when the going gets hard.

Another type of drive comes from insecurity. In her book Leading Professionals, Dr. Laura Empson, a Director at London’s Cass Business School and a Senior Research Fellow at Harvard Law, identifies insecure overachievers. Like conscientious people, insecure overachievers work hard—sometimes too hard—in an attempt to overcome their insecurities. And in fact, some professional services firms deliberately seek out and try to hire insecure overachievers.

Unlike conscientious people, however, I believe insecure overachievers are much more prone to burning out, because they are driven by a negative force (insecurity) instead of a positive one (care for their work). Empson states that these insecurities “can lead to extreme conformity and the normalization of unhealthy behaviors.” That might be OK for certain law firms or investment banks (or at least, the cartoonish version of them often presented in the media), but that’s not the type of team I’d want to risk building.

In short, ambition, insecurity-driven overachieving, and conscientiousness can all be sources of drive or intrinsic motivation, but they are different. Does that mean that those sources are mutually exclusive, or that you should avoid hiring people with ambition or insecurities? I don’t think so. I think it’s possible for a person to be intrinsically motivated by multiple sources—perhaps all three, or more. The key is being able to spot if someone is ambitious and/or insecure, and lacking conscientiousness.

Conscientiousness vs. engagement

If you’ve managed or worked with enough people, you’ve definitely come across people that might seem to exhibit high motivation in some situations but not in others. They seem to care about their work, but suddenly something changes and their drive seems to diminish. They switch jobs or teams, experience a shift in management, or go through some other event that triggers a change in their work habits or the quality of their work. So if conscientiousness is indeed a general personality trait, what explains such variability?

There is a difference between conscientiousness and engagement. Engagement can vary based on things like a person’s tasks, their relationship with their manager, their morale, how valued they feel, and so on. Even people with low conscientiousness can experience high engagement in certain contexts. In fact, some of the most brilliant people I’ve worked with can be stellar when they’re engaged, but toxic when they’re not. Engagement is highly dependent on context. Conscientiousness, on the other hand, is a general trait that tends to remain constant, even as situations change.

Employee engagement has become a management topic du jour (just Google “workplace engagement” to see what I’m talking about). I think the modern workplace has over-indexed on engagement; it’s highly important, and we should spend a lot of time on it, but if you hire the right people, it’s a lot less of a challenge. I’m definitely not saying you shouldn’t care about employee engagement at all. Hiring people without caring about their engagement is basically just an attempt to abuse their work ethic—which might work on insecure overachievers, but in the long run, won’t enable you to hire and retain talented, conscientious people. And ultimately, as a conscientious leader, caring about your colleagues should be one of your top priorities.

Skill and will

So how does conscientiousness fit into the overall picture? Let’s put together a simple model by starting with Andrew Grove’s “skill-will” framework. In High Output Management, Grove says that someone’s effectiveness at a task is a function of both their “skill” (their ability to do the task) and their “will” (their willingness to do the task).

Will and skill

Grove would call skill a person’s “task-relevant maturity.” Personally, I wish Grove had been more specific. I think there’s more to skill than just ability. Skill has two components, a dynamic and specific one (experience) and a stable and general one (intelligence). Experience grows with, well, experience. The more you perform a particular task, the more you learn about it and the more equipped you will be to perform that or similar tasks in the future with more success and less time and energy. If you write a lot of Python code for consumer web apps, you will probably get pretty good at writing Python-based consumer web apps.

But I also believe some people are just more naturally inclined to perform well in certain types of tasks. In other words, there is a more general component to skill. For decades, cognitive psychologists have debated the existence of an overarching and ingrained “general intelligence”: the idea that some people are smart and some people are not. I don’t think intelligence is that general. Personally, I subscribe more to Howard Gardner’s theory of multiple intelligences, which posits the existence of eight different kinds of proclivity (like logical-mathematical intelligence and verbal-linguistic intelligence). If you score or perform highly in one of these areas, and a task requires that kind of intelligence, you will generally be more likely to perform it well, regardless of your experience. Talented software engineers are probably high in logical-mathematical intelligence.

Experience and intelligence

So we’ve covered skill, both in the specific and the general sense. What about “will”? That’s where conscientiousness comes in. As I’ve discussed above, someone’s motivation can be broken down into two components: engagement (specific) and conscientiousness (general). Conscientiousness determines a person’s base level of motivation and how much they care about work. Engagement is context-specific. Conscientious people may experience times of lower or higher engagement, but as a general rule of thumb, they always care about their work and perform it to the best of their ability.

Conscientiousness, engagement, experience, and intelligence

Finally, in my opinion, no framework for assessing candidates would be complete without including values alignment (which, mind you, is different than “cultural fit”). Values are fundamental ideas and beliefs that guide a person or organization’s motivations and decisions. In some sense, you could view conscientiousness as a value, but your team probably has many other implicit or explicit values that govern how people communicate, what they prioritize, and how they act, and it’s important to consider whether a candidate shares or can augment your team’s values. We have a pretty solid subsection on values alignment in the Holloway Guide to Technical Recruiting and Hiring, with thoughts and contributions from people more knowledgeable than I am.

Conscientiousness is missing from startup hiring

While I incorporate all of the above five factors (relevant experience, intelligence, engagement, conscientiousness, and values alignment) in any hiring decision, I’ve found conscientiousness to be especially important and often overlooked.

Most of the hiring I do tends to be at technology startups. At startups, change and flux are constant. A startup goes through highs and lows, and may need to reinvent itself as it pursues growth and success. The tasks needed at any point in time may also vary dramatically over the course of a startup’s life. If you build a team of conscientious individuals, they will be more inclined to perform to the best of their abilities throughout all of these changes, and do it in a way that is sustainable for both themselves and for the team.

So how do you test for conscientiousness?

When reading Laszlo Bock’s Work Rules! and doing research for the Holloway Guide to Technical Recruiting and Hiring, I dug into one of the citations he uses to justify Google’s interview methods: a meta-analysis conducted in 1984 that aggregated across multiple other studies. One of the authors of that paper wrote an updated version in 2016, and after analyzing data across the past 100 years of studies, concluded that “a combination of a GMA test and an integrity test (which measures mostly conscientiousness) has the highest high validity (.78) for predicting job performance. Another combination with high validity (.76) is GMA plus a structured interview, which may in part measure conscientiousness and related personality traits.”

These are some of the questions I use to test for conscientiousness in candidates. Hopefully you’ll see a theme in all of these questions. Conscientious people value their commitments to others, whether those others are their teammates or their customers. Their successes and failures are more about impact and duty and less about ego or personal accomplishment.

Sample questions:

Ask them to walk you through a past failure. How do they define failures, and how do they react to them? Beware of people who define failures from a purely ego-driven perspective (like, “I failed to get a promotion”). Look for people who define failures by their impact on their commitments (to team-mates, to users/customers, et cetera) and who will move mountains to avoid (or fix) such failures.

Ask them about a time they weren’t able to meet their commitments. Use this more specific version of the previous question to get a general sense of how they feel about their obligations to others. How hard do they try to meet them? How do they feel if they can’t? Do they own (at least part of) the problem, or just assign blame to others?

What motivates them to work, and what does success mean? Is success about doing good, impactful work for their team and company? Or just about their personal success? Also, do they balance long-term success and short-term success? Conscientious people are less likely to optimize for short-term, cosmetic goals.

Have them tell you about a time they worked on something they didn’t enjoy. If something is important for their team or their company, are they still willing to swallow it up and do it? Or, instead, do they find ways to avoid doing it, or doing it but being resentful about it?

Look for evidence of side-projects or things that go above and beyond. This is always a good sign. Of course, be understanding of people’s personal situations—not everyone has a personal and professional life that allows them the luxury of side projects. That said, I believe most conscientious people will have evidence of these types of projects, even if they are doing them as part of their day job.

What triggered them to leave past (or current) jobs, and how did they go about leaving? Are they thoughtful about what they work on? Do they bail quickly on their teams without any regard for transition plans?

Support what you value

When you start testing for conscientiousness, you’re going to see a marked difference in the quality and longevity of your hires. It might also be time to look at your teammates and colleagues, and at yourself—who do you know who has Dhameer? Who around you inspires others? When you find them, first of all, tell them. Hiring conscientious people is a start—but you also need to create an environment where conscientiousness is valued. If you can do that, it may be the spark of your own Dhameer at work, lighting a fire in others.

Ozzie is co-founder and head of engineering at Monarch Money. He has built products and engineering teams at companies including Quora and Google. He is the lead author of the upcoming Holloway Guide to Technical Recruiting and Hiring.

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