"It Ain't the Heat, It's the Humility:" Jewish Leadership for the 21st Century An ELI Talk by Hal M. Lewis
(ג) וְהָאִ֥ישׁ מֹשֶׁ֖ה ענו [עָנָ֣יו] מְאֹ֑ד מִכֹּל֙ הָֽאָדָ֔ם אֲשֶׁ֖ר עַל־פְּנֵ֥י הָאֲדָמָֽה׃ (ס)
(3) Now Moses was a very humble man, more so than any other man on earth.

כדרך שחלק לו הכתוב הכבוד הגדול וחייב הכל בכבודו כך צוהו להיות לבו בקרבו שפל וחלל שנאמר ולבי חלל בקרבי ולא ינהג גסות לב בישראל יתר מדאי שנאמר לבלתי רום לבבו מאחיו ויהיה חונן ומרחם לקטנים וגדולים ויצא ויבא בחפציהם ובטובתם ויחוס על כבוד קטן שבקטנים וכשמדבר אל כל הקהל בלשון רבים ידבר רכות שנאמר שמעוני אחי ועמי ואומר אם היום תהיה עבד לעם הזה וגו' לעולם יתנהג בענוה יתירה אין לנו גדול ממשה רבינו והוא אומר ונחנו מה לא עלינו תלונותיכם ויסבול טרחם ומשאם ותלונותם וקצפם כאשר ישא האומן את היונק רועה קראו הכתוב לרעות ביעקב עמו ודרכו של רועה מפורש בקבלה כרועה עדרו ירעה בזרועו יקבץ טלאים ובחיקו ישא וגו':

Rambam, Laws of Kings and Wars 2:6

Just as the Torah has granted him great honor and obligated everyone to revere him; so, too, has it commanded him to be lowly and empty at heart, as Psalms 109:22 states: 'My heart is a void within me.' Nor should he treat Israel with overbearing haughtiness. For Deuteronomy 17:20 describes how 'he should not lift up his heart above his brothers.'

He should be gracious and merciful to the small and the great, involving himself in their good and welfare. He should protect the honor of even the humblest of men.

When he speaks to the people as a community, he should speak gently, as I Chronicles 28:2 states 'Listen my brothers and my people....' Similarly, I Kings 12:7 states 'If today, you will be a servant to these people....'

He should always conduct himself with great humility. There is none greater than Moses, our teacher. Yet, he said Exodus 16:8: 'What are we? Your complaints are not against us.' He should bear the nation's difficulties, burdens, complaints, and anger as a nurse carries an infant.

Psalms 78:71 refers to a king as a shepherd: 'to pasture, Jacob, His nation.' The prophets have described the behavior of a shepherd (Isaiah 40:11): 'He shall pasture His flock like a shepherd, He shall gather the lambs with His arm and carry them in His bosom."

Greatness and humility, in the Jewish tradition, are not incompatible. They complement one another.
-R. Louis Jacobs, "Humility in Judaism," The Jewish Religion: A Companion (1995).

In other words, humility is not the enemy of self-esteem, but of pride.

-Byron R. Sherwin, Jewish Ethical Values (2015), p.93

Humility is not a question of thinking less of yourself. It is a question of thinking of yourself less.

-Larry Bossidy