Surround Yourself With Good People Using These 12 Questions

An often-overlooked skill most of us could stand to improve is our judgment of others.

Is there any way to judge people better and quicker? Pexels

An often-overlooked skill most of us could stand to improve is our judgment of others. The choices we make about our colleagues and associates form the foundation of our personal fulfillment because, in the end, we are just the sum of our interactions and experiences with others.

My first company grew to over 700 employees. During that growth, I learned that everything we do and everything we are is influenced by the people with whom we choose to surround ourselves. It’s taken me many years of taking the right steps—and several missteps—to see how the successes I’ve had in my business career and personal life ultimately reflect the quality of the decisions I’ve made about people. American writer and activist Rita Mae Brown once said, “Good judgment comes from experience, and experience comes from bad judgment.” I’ve found that a lot of bad judgment revolves around people.

My definition for good people is those who are committed to continuously cultivating the values that help them and others become the fullest possible versions of who they are. Herein lies a conundrum: goodness is about positively influencing others, but our own ability to do so is significantly shaped by those who influence us. How we treat others is a function of our memories and experiences—good and bad—of our treatment at the hands of other people.

If you want to become a better judge of people, you have to look beyond competency or status. Famous names and important titles are the easiest way to assess measures of goodness, but perhaps the least useful. What we really need to do is get a sense of a person’s character and values, and in particular, whether they espouse the values I’ve identified in my book Good People—truth, compassion, and wholeness.

You make judgments about people all the time, whether or not you realize it. You hire new employees, meet new people, interact with prospective partners, and court potential investors. You develop and deepen your relationships every day. Each instance is a moment of people judgment.

With enough time, most people can develop a pretty keen understanding of another person’s character and goodness. But that’s just the thing—it takes a long time. Is there any way to judge people better and quicker? Over the course of my career, I have used an almost embarrassingly large array of tools, diagnostics, and frameworks to analyze companies. But none of them specifically addressed how best to judge and develop good people.

The following twelve questions, however, will do just that. They’ll help you look past brand-name credentials—that irresistible shorthand for judging others—and help you focus on a person’s authentic character and values.

1. Is This Person Self-Aware?

Self-awareness is the nucleus of success and happiness. Ask yourself, is this person intellectually honest about who she is, and about her strengths and weaknesses? Are her thoughts, words, and actions consistent? The core of self-awareness is honesty and consistency in what someone says, believes, and does. My advice is to look for people who are willing to put down on paper what they say they’ll do and then actually follow through on it.

2. Does This Person Feel Authentic or Obsequious?

Few things are worse than phony praise. We’ve all been in a situation where the presentation feels over the-top, obsequious, or even staged. Good people do not feel compelled to tie themselves into knots in order to impress others. When good people offer praise or criticism, it comes across as authentic, genuine, and in the service of objective truth. So ask yourself, does this person seem down-to-earth, unafraid, and comfortable in their own skin? Be wary of those who alter their core behaviors among different sets of people.

3. What Is This Person’s Talk-to-Listen Ratio?

Many of us find self-confidence intoxicating, but we should be careful if a person talks more than he or she listens. Is this person drunk with self-importance? Is he indifferent to what others have to say? Does he believe he has nothing to learn from others? Listening is among our most important learned skills, and I’ve found that listening and caring go hand in hand. One good litmus test for assessing whether a person is a good listener is to follow the example of Dominic Barton, managing partner of McKinsey & Company: note the number of times in a conversation a person uses the pronoun “I” versus “we.” Another red flag to watch out for is the “topper”—someone who always has to “one-up” the last person who spoke in a conversation.

4. Is This Person an Energy Giver or Taker?

An old Chinese proverb says the best way to get energy is to give it. We all want to work with lively, passionate, and inspiring people who will help energize our teams to do their best work. The next time you’re at a cocktail or dinner party, try to assess whether the person sitting across the table from you is the equivalent of an energy vampire. Ask yourself, does this person chip away at skepticism and brim with positivity, or does he exude cynicism and negativity? Energy givers are more likely to listen compassionately to other people’s ideas because they approach the world with an open mind. If you want to have fun with this exercise, try asking yourself, what song would this person be? Do they come across an uplifting and energizing “fight song,” or do they remind you of the most depressing tune you know?

5. Is This Person Likely to Act or React?

Some people become critical and defensive when asked to do something outside of their job description or everyday responsibilities, while others jump in at once, push forward, and try to solve the problem. This is a fundamental difference between individual contributors and team leaders. Try to maximize the number of the latter in your inner circle, and be wary of those who reflexively react negatively to new tasks. Think hard about what jobs the person you are evaluating would be willing to take on, large or small, and how collaborative you think they’d be in getting them done. I’ve never forgotten a phrase an old business school classmate of mine liked to say: “Action, not reaction, please.”

6. How Does This Person Treat Someone He Doesn’t Know?

Closely watch how a person interacts with strangers, drivers, waiters, and colleague. Does she engage with the people serving her or treat them as social and professional inferiors? Can you picture this person coming to a stranger’s aid? Many of the good people I know consider equality one of their core values. On the other hand, I’ve found that condescension, brusqueness, rudeness, and snobbery often derive from a tacit fear that, in the end, we’re not as special as we think we are—that in different circumstances, with a few unlucky breaks, we wouldn’t be in the impressive roles or positions we find ourselves in today. Kindness to strangers is a critical indicator of empathy, which is absolutely essential to effective teamwork.

7. What Is This Person’s Spouse or Partner Like?

We are known by the company we keep. If you are considering hiring an important employee, invite the candidate out to dinner with his or her spouse or partner. What can you learn about the candidate from the person with whom they’re closest? If you’re bold, consider asking the candidate’s spouse or partner how they would describe the candidate’s best and worst qualities, they gauge how their lists match up. It’s also important to gather references not just from those names listed by the candidate, but also from others with whom you have common connections.

8. How Does This Person Respond to Setbacks?

Personal history matters. In my last book, my coauthors and I found that roughly two thirds of successful entrepreneurs experienced some form financial or social hardship early on in their lives, in part because developing resilience in response to adversity is a key predictor of success later in life. I’m not saying anyone should willfully struggle or court failure, but it is important to consider how someone transforms low points into opportunities for learning. Good people codify lessons from life’s challenges, reflect on what was inside and outside of their control, and ask themselves, “What would I do differently next time?”

9. What Has This Person Been Reading?

Reading frames ideas, ignites new thoughts, and adds complexity and nuance to familiar perspectives. As we gain knowledge, we better comprehend the vastness of what we neither fully know nor understand. The realization that so much of the universe is yet unknown should spark our intellectual curiosity. As E. O. Wilson once said, “Our sense of wonder grows exponentially. The deeper the knowledge, the deeper the mystery.” The most interesting, soulful people I know read often and widely. Reading also helps us connect to others via stories, metaphors, and parables. The better read someone is, the better she is able to use the powers of analogy and storytelling to clarify complex ideas and contextualize her place in the wider world.

10. Would You Ever Want to Go on a Long Car Ride with This Person?

Can you imagine driving cross-country with this person? If you set aside professional skills, references, and other workplace commonalities, could the two of you get along, agree, laugh, and sit comfortably together in silence? This question helps reveal how you would feel about this person as a long-term colleague or partner. It reminds us to think hard about the “who” a person is, rather than “what” they are. Yes, competencies matter on the job for day-to-day tasks, but the car ride test ask us to reflect on the value of our relationships in the long run. And uncovering the “who” of another person requires allowing that person to get to know you, as well. Perhaps by testing whether your own willingness to break out of your workplace role and open up with a colleague, you’ll learn something about yourself, too.

11. Is This Person Comfortable with His Idiosyncrasies?

Most people are much more interesting than what they do for a living. To use a baseball analogy, our core personality has much more to do with our curveball than our fastball. It is our quirks, oddities, and eccentricities that define us, rather than our conventional qualities. When evaluating a job candidate, try to gauge whether this person is at ease with idiosyncrasies. Does he seem embarrassed, self-conscious, even furtive? Does this person place a premium on conforming with “the establishment” or seem distressed by other people’s weirdness? We all function best when we feel free to be ourselves. In some cases, simply being true to ourselves—to our own idiosyncrasies—can make us good. One of the highest forms of truth is living as our real, true selves.

12. Is This Person Multidimensional or Multidisciplinary?

An inability to navigate between, around, and across diverse fields of learning and experience is a true handicap in the business world. When I was an undergraduate at Harvard, I was lucky to take several courses by the late evolutionary biologist Stephen Jay Gould. I vividly remember the week Professor Gould introduced the class to the concept of “spandrels.” Spandrels are an architectural feature (the “webbed” space between two arches) but Gould redefined the word in terms of evolution, describing it as an “accidental,” positive by-product of some other evolutionary change rather than a feature of an organism’s essential function. Birds, for example, originally grew feathers for thermal warmth—only later were they adapted for flight. The takeaway is that we should embrace in-between and unexpected creative spaces. We should embrace the spandrels. Like well-read people, multidisciplinary people approach the world with unconventional perspectives that open up new possibilities and allow them to solve problems more creatively.

If we ask these questions of the people who surround us—and more important, if we honestly ask these questions of ourselves—we will inevitably see that there is much work to be done on our journey and quest for goodness.

Anthony (Tony) Tjan is CEO and Managing Partner of Cue Ball. He leads the firm’s overall direction and is involved across deal development activities, including on-going guidance and mentorship to the leadership of Cue Ball’s portfolio companies. Tony is one of the World Economic Forum’s Global Leaders for Tomorrow and has been a speaker at the TED conference. His new book, Good People: The Only Leadership Decision That Really Matters, is available now.

Surround Yourself With Good People Using These 12 Questions