4 Leadership Lessons from History’s Greatest Ladies

Stephanie Mickle
5 min readAug 21, 2019

Women have been ruling empires, commanding armies, and generally leading in ways big and small for millennia. Leadership comes in many shapes and sizes. In my book, Follow the Leader, I define it as using your talents to build relationships and influence, but that can take many forms. So ladies, if you’re looking to conquer the world, you have a wealth of role models.

1. Queen Boudica — Activism

Boudica in her chariot leading her army

From the Romans perspective, Queen Boudica of the Iceni was the Celtic upstart who led the British to burn three of their settlements. But a less biased look reveals a mother who turned her personal tragedy into a movement against colonial oppressors. Upon her husband’s death, the Roman governor disregarded local law and seized the control of her lands. When she protested, he ordered soldiers to assault her and her daughters. Enraged, she rallied her people in the largest revolt the Romans would ever face on the islands.

Instead of letting oppressive acts cow her, Boudica turned the injustice against her family into a flashpoint. At once, she turned herself into a symbol of the brutality of Roman rule and the face of the fight against it. In her we can see the suffragists who endured prison for voting, the Freedom Riders who revealed the ugliness of the Jim Crow south, and the mothers who stand up to the gun lobby which stole their children. Granted, Boudica’s movement involved more chariots than contemporary examples, but it was a different time.

2. Theodora of Byzantium — Networking

Theodora with others in mosaic

If you take away one lesson from the life of Empress Theodora of Byzantium, let it be this: always be ready to network. Though a humble actress and former prostitute, young Theodora met and became the beloved of Justinian, future emperor. They had nothing in common except that they were both fans of the blue chariot racing faction or deme. So the next time you see someone influential at your local party meeting, sports stadium, or protest, introduce yourself. Who knows what will happen?

Becoming empress was only the beginning of Theodora’s successes. Here, she teaches us the second lesson of networking: never throw away a relationship. Using connections from her disreputable years, she served informally as spymaster. When the plague ravaged the empire and sent Justinian into a coma, she single-handedly held the empire together — taking drastic actions and never doubting her authority. With her spy network, she uncovered plots, recalled dangerous generals, and served as a symbol of continuity and unity in Constantinople's darkest hour.

3. Catherine the Great — Avoiding Impostor Syndrome

Catherine in military dress riding a white horse

Taking on a leadership role can be daunting. Oftentimes, a woman can be the most qualified person in the room and still not believe that she is good enough to even apply for the position of team manager or supervisor. As a result, overconfident, unqualified men take the reins and the whole team suffers. If women want to get ahead, more of us need to accept that we are better than our bosses.

Tsarina Catherine the Great of Russia certainly took this lesson to heart. She witnessed her incompetent husband, Tsar Peter III, run her adopted country into the ground and squander countless opportunities and relationships. Instead of despairing, she made plans. Then, when Peter was away from Moscow preparing to lead Russia to a military disaster for personal gain, Catherine struck. Having won the support of local garrisons, she marched on the capitol, convinced the Synod to declare her Empress, and won the support of the people before Peter even knew what was happening.

Catherine greets supporters on the day of the coup

Did the new Empress agonize over her qualifications? Maybe. As she spoke to the people of saving Russia from foreign rule and foreign religion, Catherine was well aware that, like Peter, she was born in Germany and only a recent convert to Russian Orthodoxy. But we know she did not let such worries keep her from leading Russia to a golden age of peace, prosperity, and reform.

4. Cheng I Sao — Team Management

Portrait of Cheng I Sao

Tired of seeing monarchs on this list? Then this entry should be a breath of fresh air. After all, Cheng I Sao was a pirate queen — completely different. Her exploits reveal an under-discussed element of leadership: team management. Part of being a leader is equipping your team to perform their tasks effectively and reflect well on you as their leader. At first, our image of backstabbing buccaneers makes pirates seem like the hopeless cases. But that just shows how much influence Cheng I Sao had.

When the fleet commanders of the 70,000-strong pirate confederation named her leader, her first act was implementing a law code. Her new rules put to death any pirate who raped a captive, stole from his coworkers, or disobeyed orders. With this discipline, she was able to coordinate her fleets to push the confederacy to the point where it controlled all trade from the Gulf of Tonkin to the Pearl River Delta. But she also wasn’t afraid to change careers when she felt the time was right.

Cheng I Sao in a print battling Qing sailors

When the Qing government finally managed to muster a fleet to trap hers and exposed the cracks in her coalition, she decided to go straight while she had the strongest bargaining position. In the end, she agreed to stop raiding if the Qing pardoned her and all her sailors, paid her a bribe, and allowed her to keep a personal fleet for legitimate trade. Without the strong, ordered team she developed, such a deal would have been impossible. Just imagine what you could accomplish with a solid team at your back.

Discover more leadership lessons here: https://stephaniemickle.com/book-follow-the-leader/

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Stephanie Mickle

Author, Follow the Leader: Believe in Yourself. Craft Your Future. Mickle Public Affairs Agency. @stephaniemickle www.stephaniemickle.com