Proverbs and Sayings on Leadership [With Meaning and Example]

Proverbs and sayings are popular nuggets of wisdom, often in circulation for centuries and even millenniums. This post contains proverbs and sayings on leadership, divided under three categories.

If you’re looking for more proverbs and sayings, you can find plenty of them in the resource below. It contains proverbs on topics such as life, family, friends, love, health, happiness, money, hard work, time, time management, teamwork, leadership, business, education & learning, and more.

1. About leaders and leadership

An army of sheep led by a lion would defeat an army of lions led by a sheep.

An Arabic proverb. This proverb exemplifies importance of leadership. A strong army (lions) led by a weak leader (sheep) can lose to a weak army (sheep) led by a strong leader (lion).

Example: The next CEO hasn’t held any leadership position in a large organization. I hope the board doesn’t regret its decision because an army of sheep led by a lion would defeat an army of lions led by a sheep.

It is easy to find a thousand soldiers, but hard to find a good general.

A Chinese proverb. Leaders are not easy to find. Retain them at whatever price it takes if you’ve them.

Example: The Vice President was all set to leave Google and lead Twitter, but Google somehow convinced him not to leave as it knew that it’s easy to find a thousand soldiers, but hard to find a good general.

Better be head of a dog than tail of a lion.

People often get lost in large organizations where they become just one of the cogs in a large wheel. Sometimes people get frustrated with bureaucracy of large organizations and sometimes they struggle to find meaning in their lives as they go through the daily rigmarole. Better is to be an important cog in a smaller organization and make tangible impact.

Example: My friend recently shifted from a large software company to a start-up. His reason was simple: Better be the head of a dog than the tail of a lion.

If you are not the lead dog, the view never changes.

This Canadian proverb finds origin in dogsledding, where, but for the lead dog, the dogs only see the rear of the dogs in front of them. You should be watchful for stagnation at workplace, the reason why many leave large organizations to join smaller, fast-growing organizations. For example, in China, many have left Alibaba to join TikTok.

Example: As customer service representative, I’ve been doing the same work for donkey years now. If you are not the lead dog, the view never changes.

The higher the monkey climbs the more he shows his tail.

An incompetent leader gets exposed soon: The higher an incompetent person rises in an organization, the more his incompetence is exposed.

Example: After the recent promotion, the official, who somehow rose in ranks despite lack of merit, now headed a much larger department. As a result, his incompetence was now exposed to far more people. The higher the monkey climbs the more he shows his tail.

The next two proverbs tell that leadership isn’t a cushy role. One has to be constantly on toes.

The highest branch is not the safest roost.

Those in the highest positions can be vulnerable as many aspire to replace them. Second, if the person is replaced, it’s not easy to find a similar position because of paucity of roles at the top. (That’s one of the reasons for large severance packages of senior executives.)

Example: In earlier times, kings used to be on their guard all the time, suspicious of plots to overthrow them. The highest branch is not the safest roost, after all.

Uneasy lies the head that wears a crown.

Those in leadership positions can be weighed down by responsibilities and insecurity of losing their position. So, leadership positions aren’t as cushy as people from outside believe them to be.

Example: The Vice President in our division was quite a busy and harried person, regularly reviewing our progress against the targets and answering to the top management. Uneasy lies the head that wears a crown.

2. Managing people

Managing people is an important leadership task in any organization. Here are few proverbs on how good leaders manage people.

A man is a lion in his own cause.

People do well when they’ve some personal interest in the work they’re doing. For example, they may be assigned a task that interests them.

Example: If I was put in digital marketing, I could have done wonders for the organization. After all, a man is a lion in his own cause.

It is good to make a bridge of gold to a flying enemy.

This proverb has been written in the times when wars were common. It says that defeated enemy should be given an easy path to flee. Otherwise, he may inflict great loss in the desperate bid to save himself. The proverb applies to workplaces as well, not in fighting with competitors but with parting employees. Employees who have resigned or have been asked to leave should be treated with politeness and respect, helped with all the leaving formalities, and even assisted in finding the next job. If they part ways amicably, they’re less likely to badmouth your organization and may even give business as an alumnus.

Example: The Company has retrenched more than 20 employees because of the pandemic, but we need to make sure that they part on as good terms as possible. It is good to make a bridge of gold to a flying enemy.

Only the wearer knows where the shoe pinches.

Only the person who is experiencing a problem knows its cause and extent. Good leaders should try to understand cause of the problem and help the person, and not judge in any way. In other words, they should be empathetic.

Example: Tom: He seemed to be off-colour in the meeting today. Maybe he didn’t prepare because he doesn’t care about these meetings. Jerry: We don’t know anything about the matter and therefore shouldn’t speculate. Only the wearer knows where the shoe pinches.

Before criticizing a man, walk a mile in his shoes.

Similar to the last one

3. Other traits of leaders

If you want peace, prepare for war.

If you utilize the peace time to get better at war, your adversaries will hesitate in waging a war on you, and hence the time of peace will stretch.

Example: We’re in a competitive industry. Therefore, we should use this time of high growth and less competition (time of peace, in other words) to shore up capital, diversify, invest in revenue streams of future, and hire good talent. If you want peace, prepare for war.

Tomorrow belongs to people who prepare for it today.

You can dominate in future by planning and then putting in the work today.

Example: Some countries are investing heavily in modern technologies such as AI, genomics, and electric vehicles. Tomorrow belongs to people who prepare for it today.

Straws tell which way the wind blows.

A seemingly non-significant event may indicate the course of future events. Good leaders keep their ears to the ground for seemingly insignificant, yet important, events.

Example: Before iPhone, BlackBerry was the preferred smartphone, especially for working professionals. Within few years of iPhone’s launch, employees at RIM (Company that manufactured BlackBerry) started keeping two phones: a BlackBerry for the workplace (for obvious reasons, they couldn’t use another phone for work) and an iPhone for personal use. This was an indication (straw) that iPhones were on an explosive growth curve, but RIM failed to see which way the wind was blowing. Within few years, it lost almost all its market share.

Coming events cast their shadows before.

Similar to the last proverb

He who thinks too much about every step he takes will always stay on one leg.

A Chinese proverb. Indecisive persons will deliberate on every step so much that they’ll rarely take a task to its logical conclusion. It’s fine to look at pros and cons, but average leaders hesitate to step into unknown, and that’s where outsized returns are.

Example: Steve Jobs stepped into quite a few unknowns by having swiping – and not keying in – and other features in the first I-Phone. His action clearly contravened the proverb he who thinks too much about every step he takes will always stay on one leg.

The best armour is to keep out of range.

An Italian proverb. The best armour is one that keeps your rivals at arm’s length. Peter Thiel, one of the founders of PayPal, Palantir, and Founder’s Fund, in his book Zero to One, argues that founders should aim to create highly defensible positions which will keep the competition at bay.

Example: Facebook bought Companies such as WhatsApp and Instagram to keep potential competitors at bay. After all, the best armour is to keep out of range.

After victory, tighten your helmet chord.

A Japanese proverb. There is no room for complacency. Get down to the work after the victory. Jeff Bezos, the founder of Amazon, calls it Day 0 mentality.

Example: Our Company has won a major deal worth $600 M, but we can’t relax as many more deals are up for grabs, with the competition gnawing at our heels. After the victory, it’s time to tighten our helmet chord.

When winds of change blow, some build walls and others build windmills.

When things change, some get overly defensive (build walls), but leaders are optimistically cautious. They adapt to change and find opportunities (windmill) where others see threat.

Example: Whereas most Companies nearly froze for several months into Covid-19 pandemic, few changed their business model to keep going. When winds of change blow, some people build walls and others build windmills.

Discretion is better part of valour.

It’s better to be careful than show unnecessary bravado, which may result in grave loss. In other words, leaders know when to retreat and when to persist.

Example: Sensing adverse battlefield conditions, the commander ordered his troops to retreat. Discretion indeed is better part of valour.

A good retreat is better than a bad stand.

Similar in meaning to the last one

Revolutions are not made with rose water.

It’s not possible to bring about drastic changes by pleasant, easy, or peaceful means, or without causing damage or suffering.

Example: The government raised tax rates to fund its infrastructure expansion plan, which led to discontent among people. Revolutions are not made with rose water.

Distance lends enchantment to the view.

When we get stuck in the day-to-day work, we fail to see the big picture. Taking break and seeing things dispassionately from a distance can tell us if we’ve deviated from our intended path. Such breaks can help us detect slow poison that creeps into our personal and professional lives and take corrective steps. (Slow poison – bad habits, for example – creeps in slowly into our lives without us realizing it.)

Example: When leading Microsoft, Bill Gates used to take breaks for few days from his work twice a year to think about the big picture. Distance lends enchantment to the view.

Vision without action is a daydream. Action without vision is a nightmare.

A Japanese proverb. If you’ve vision or an idea to make positive change and you don’t do anything about it, you’re merely daydreaming. Conversely, if you act without vision or idea, you may unleash something harmful.

Example: Lot of people have brilliant ideas to make positive change in the society as an individual or by launching an entity, but they fail to act. On the other extreme are people who act according to a misguided vision and cause, intended or unintended, harm to others. Rightly said, vision without action is a daydream. Action without vision is a nightmare.

If you must play, decide on three things at the start: the rules of the game, the stakes, and the quitting time.

A Chinese proverb. If you decide to enter the fray, set the boundaries beyond which you wouldn’t go.

Example: Uber decided to pour in, and lose, billions of dollars in its overseas markets to gain market share, but it eventually exited from most of these markets. If you must play, decide on three things at the start: the rules of the game, the stakes, and the quitting time.

Who makes himself a sheep, will be eaten by wolves.

If you behave timidly, get easily influenced, or accept injustices, people will take advantage of you. Once a path is picked, leaders don’t behave like a sheep.

Example: The team played on an unsure foot and hence lost the match. Who makes himself a sheep, will be eaten by wolves.