Dear Rachel,

My boss has just promoted me from a job at a desk at an advertising agency to a position where I will have more contact with clients. I’m a shy person by nature, but my boss seems to believe that I have My boss just promoted methe skills to chat up clients and make them want to work with us. The problem is that it takes me a long time to feel comfortable with people, and until I do, my conversation is stilted. I’m afraid I’m not going to do a very good job. Does the Torah have some advice on how to develop people skills?

Painfully Shy


Dear Promoted,

First of all, congratulations on your new job! Your boss could have picked someone more naturally outgoing and gregarious, but she chose you, which means that she appreciates your particular attributes.

“Shy” is a more judgmental term for “introverted.” Introverted people usually consider what they’re going to say before they speak, are more sensitive, listen more attentively and don’t overwhelm the people they’re with. It could be that your boss saw that these qualities would be advantages in your new position.

That being said, you are right that the Torah is the ultimate people-skills manual, so I will be happy to share with you a few of its tips. This advice can help you upgrade the rest of your relationships as well.

1. Love Yourself

The commandment to love your neighbor as yourself means you have to love yourself first. When you love yourself, you can then love others, and others will love you back. When you appreciate your strengths and fine qualities, others will too.

2. Smile

The Talmudic sage Rabbi Yochanan teaches that smiling at another person is greater than giving him a glass of milk, because a smile nourishes the soul.1 In the same vein, in Ethics of the Fathers, Shammai says to greet everyone with a pleasant countenance.2 A welcoming and encouraging smile and expression goes a long way to making people feel good. Smiling sincerely will not only help you win over clients, it will also give their spirits a lift.

3. Develop a Good Eye

Having a “good eye,” an ayin tovah, is one of the most important aspects of a relationship. According to Rabbi Eliezer in Ethics of the Fathers, it is the most important attribute for us to acquire.3 When you meet someone, try to find something about that person that you like, even a minor detail. Then keep your mind focused on that detail, trait or behavior. The person will feel the positive waves of energy washing over them.

4. Find Something You Have in Common

Another interpretation of the mitzvah to love your neighbor as yourself is, “Love your neighbor who is as yourself.” It’s easier to love another person when you have things in common. Look for those things in your clients. What are the traits that you most value and admire? Think about the common qualities that bring you and your friends together. Is it a desire for self-growth, a drive to contribute to the world or to have fun? Or is it an ambition to succeed? When you can pinpoint the qualities and motivations that you value in the people you talk to, you will find it easier to speak the same language.

5. Find Something the Other Person Can Teach You

The sage Ben Zoma says, “Who is wise? He who learns from every person.”4 There is no one from whom you can’t learn something. Taking an interest in other people’s interests and experiences makes them feel important, and gives you an opportunity to learn something from them. It also makes them more open to learning something from you.

6. Focus on What You Can Give

Focus on what you can give the other person, not on what you want from them. “The world is built on kindness,” King David tells us in Psalms.5 There is a Breslov chassidic teaching that says: “G‑d says, ‘All I ask is that you do kindness for one another.’” G‑d created the world for kindness, and that includes the kindness we demonstrate in business relationships.

7. Create a Partnership

Ask yourself how the two of you can create something wonderful together. King Solomon taught that “two is better than one.”6 Learning in yeshivahs is typically done in pairs, because the give-and-take between two people is exponentially more productive than one person learning or working alone. When we work together, we help each other make up for our weaknesses, and we support each other’s strengths. When you come to a client with the attitude that you are working together towards a common goal, you are creating a partnership.

8. Be Hospitable

Show genuine concern for the other person. Hospitality to clients is like an extension of the mitzvah of hospitality to guests. Are they hungry, thirsty, cold, tired? Do they prefer to meet in an office, at a restaurant, in the park? What time is good for them? Do they want to listen, or do most of the talking? Can you drop them off somewhere?

9. Be Modest

A shy person is unlikely to brag or boast, and arrogance is the trait most loathed by G‑d. A soft sell not only works better with your personality, it will probably be better at convincing the client. As King Solomon said, “The words of the wise are heard softly.”7

10. Be Honest

Be impeccable in your honesty and integrity. Distance yourself from falsehood. People will forgive many slights, but if you lie, cheat, or steal their time, money or affection, it will be virtually impossible to build up trust again.

Insight, sensitivity, sincere caring and integrity go a longer way than charisma, overconfidence and a winning sense of humor.

Polish the diamonds of your personality with the wisdom of Torah, and your people skills will shine through.

Good luck,

Rachel