Leadership Trivia
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98 free Leadership trivia questions with answers — history quiz, new questions added Oct 2026.
Fifty-three leadership trivia questions with answers, written for team meetings, corporate training icebreakers and anyone who enjoys the history of how people lead. Half the set covers famous leaders: Cincinnatus handing back power after sixteen days, Shackleton's 720-mile lifeboat voyage, Mandela on Robben Island, Merkel, Thatcher, Mary Barra and Satya Nadella. The other half covers the ideas: Maslow's hierarchy, Tuckman's forming-storming-norming model, the Peter principle, servant leadership, OKRs, Six Sigma and the golden circle. There are also a few questions on the coaches whose methods crossed over into business, from John Wooden's Pyramid of Success to Vince Lombardi, and on the classic books, from Machiavelli and Sun Tzu to Covey, Collins and Sinek. Difficulty runs from easy to genuinely tricky, so a mixed group will find both quick wins and arguments. Every answer is checked against a cited encyclopaedia page. Play it free here, see your score, and share it with the colleague who keeps quoting Drucker.
30 of 98 questions with answers and explanations. Play the quiz
Q 01Who wrote 'The Servant as Leader', the 1970 essay that popularised the phrase 'servant leadership'?
Robert K. Greenleaf
Robert K. Greenleaf. A retired AT&T executive, he took the idea from Hermann Hesse's novel Journey to the East, in which the travellers' humble servant, Leo, turns out to be the head of their order.
Q 02According to the Peter principle, employees in a hierarchy tend to be promoted until they reach what?
Their level of incompetence
Their level of incompetence. A study of sales staff at more than a hundred firms found the joke holds: the best sellers were the likeliest to be promoted, and then the likeliest to do poorly as managers.
Q 03Parkinson's law, first published in The Economist in 1955, states that work expands to fill what?
The time available for it
The time available for it. Parkinson backed the joke with Royal Navy figures: between 1914 and 1928 the fleet lost two-thirds of its capital ships, while the Admiralty's officials grew by 78 percent.
Q 04Which MIT management professor contrasted Theory X bosses, who assume workers are lazy, with trusting Theory Y bosses?
Douglas McGregor
Douglas McGregor. His 1960 book The Human Side of Enterprise carried Abraham Maslow's psychology into business schools, arguing that a manager's view of human nature decides how he manages.
Q 05Bruce Tuckman's 1965 model of team development runs forming, storming, norming and then which stage?
Performing
Performing. Tuckman drew the stages from fifty published studies; when he revisited the model in 1977 only one of 22 newer studies had set out to test it, and he added a fifth stage, adjourning.
Q 06James MacGregor Burns, who set 'transforming' leaders against 'transactional' ones in 1978, was also a prize-winning biographer of whom?
US presidents
US presidents. His Franklin Roosevelt biography won a Pulitzer, but when the Kennedys cooperated on a 1960 life hoping for a flattering portrait, Burns called John F. Kennedy 'casual as a cash register'.
Q 07Which Scottish essayist behind the 'great man theory' wrote that history is 'but the biography of great men'?
Thomas Carlyle
Thomas Carlyle. He made the case in six public lectures in 1840; Herbert Spencer later answered that great men are products of their societies: 'Before he can remake his society, his society must make him.'
Q 08Which now-common business term is management thinker Peter Drucker credited with coining?
Knowledge worker
Knowledge worker. Drucker foresaw an economy in which brains would trump brawn, and in 1999 he was still calling the productivity of such workers the biggest challenge facing management.
Q 09In Abraham Maslow's 1943 hierarchy of needs, which need sits at the very top?
Self-actualization
Self-actualization. Maslow never drew the famous pyramid: it first appeared in a 1960 business-journal article by consulting psychologist Charles McDermid, and management textbooks spread it from there.
Q 10The subtitle of Daniel Goleman's 1995 bestseller Emotional Intelligence says it can matter more than what?
IQ
IQ. Psychologists Peter Salovey and John Mayer had framed the idea in a 1990 paper; Goleman's book made it famous, and he went on to tell executives that it is the sine qua non of leadership.
Q 11In Stephen Covey's 1989 bestseller The 7 Habits, what is the first habit?
Be proactive
Be proactive. Covey put it first because every other habit rests on it: drawing on psychiatrist Viktor Frankl, he argued that between what happens to us and how we respond lies the freedom to choose.
Q 12Whose public-speaking course became the 1936 bestseller How to Win Friends and Influence People?
Dale Carnegie
Dale Carnegie. A Simon & Schuster man who took the 14-week course had a stenographer type up the lectures to talk him into a book, which has since sold more than 30 million copies.
Q 13Jim Collins's Good to Great names its focus-on-one-thing concept after which animal?
Hedgehog
Q 21UCLA coach John Wooden, who won ten NCAA titles in 12 years, taught players his 'Pyramid of' what?
Success
Success. Wooden defined it not as winning but as the peace of mind of knowing you made the effort to be the best you could, and called the pyramid 'the only truly original thing I have ever done'.
Q 22Which NBA coach, nicknamed the 'Zen Master', won 11 championships as a head coach?
Phil Jackson
Phil Jackson. The nickname came from a coaching style steeped in Eastern philosophy and Native American practice; it brought six titles with the Chicago Bulls and five with the Lakers, after two as a Knicks player.
Q 23Which English club did Sir Alex Ferguson manage for 26 years, winning 13 Premier League titles?
Manchester United
Hedgehog. Collins took it from Isaiah Berlin's essay on the ancient saying that the fox knows many things but the hedgehog one big thing; he found his great companies were led by hedgehogs, their rivals by foxes.
Q 14In Simon Sinek's 'golden circle' from Start with Why, 'Why' comes ahead of which two words?
How and What
How and What. Sinek drew the three as rings with Why at the centre, and argued that Apple and Martin Luther King Jr. won their followings by starting there, with a sense of purpose, before saying how or what.
Q 15Psychologist Kurt Lewin described three leadership climates: authoritarian, democratic and which third?
Laissez-faire
Laissez-faire. French for 'let them do', it leaves every decision to the group with no part played by the leader; a 2004 review pooling 87 studies found such hands-off leadership went with worse results.
Q 16Who wrote Team of Rivals (2005), a study of Abraham Lincoln and his cabinet?
Doris Kearns Goodwin
Doris Kearns Goodwin. Her title refers to Lincoln handing cabinet posts to William Seward, Salmon Chase and Edward Bates, all of whom he had just beaten for the 1860 Republican nomination.
Q 17On which island did Nelson Mandela spend 18 of his 27 years in prison?
Robben Island
Robben Island. Put to hard labour in a lime quarry there, he secretly wrote the first draft of his memoir Long Walk to Freedom and had it smuggled out; he walked free from Victor Verster Prison in 1990.
Q 18To which island did Ernest Shackleton sail a lifeboat from Elephant Island to fetch help for his stranded crew?
South Georgia
South Georgia. The boat landed on the uninhabited side, so Shackleton and two companions crossed its unmapped mountains on foot to a whaling station, and all 28 men of the Endurance were saved.
Q 19Which American carmaker made Mary Barra its chief executive in January 2014?
General Motors
General Motors. She joined its Pontiac division in 1980 as an 18-year-old co-op student and never left, rising over three decades to become the first woman to lead a major carmaker.
Q 20Alexander the Great was tutored by which philosopher until the age of 16?
Aristotle
Aristotle. His fee was a city: Philip II rebuilt the philosopher's hometown of Stageira, which he had destroyed, and Plutarch says Alexander later slept with Aristotle's edition of the Iliad under his pillow.
Manchester United. The club had gone 26 years without a league title when he delivered his first in 1993, his seventh season in the job; he retired in 2013 with 38 trophies.
Q 24Which political treatise, written in 1513 but published posthumously, argues it is safer to be feared than loved?
The Prince
The Prince. Machiavelli wrote it months after the returning Medici had him jailed and tortured, then dedicated it to a Medici in the hope of winning back a post; it was printed five years after he died.
Q 25Sun Tzu's The Art of War ranks what above winning every battle?
Bloodless victory
Bloodless victory. The treatise calls breaking the enemy's resistance without fighting the supreme excellence, treats combat as what is left when other plans fail, and calls besieging walled cities the worst policy of all.
Q 26Which Roman emperor wrote Meditations in Greek rather than Latin?
Marcus Aurelius
Marcus Aurelius. He kept the Meditations as a private notebook, written partly on campaign in central Europe, and probably never meant anyone else to read it.
Q 27The Roman hero Cincinnatus is celebrated for winning a war as dictator and then immediately doing what?
Returning to his farm
Returning to his farm. In Livy's telling, envoys found him at the plough when they came to offer him supreme power; a society of Continental Army officers took his name, and the city of Cincinnati took theirs.
Q 28What was Angela Merkel's profession before she entered politics after the fall of the Berlin Wall?
Scientist
Scientist. With a doctorate behind her, she worked at an East Berlin research academy until 1989, was an East German government spokeswoman within months, and 16 years later became Germany's first female chancellor.
Q 29Before Jacinda Ardern in 2018, who was the only elected head of government to give birth in office?
Benazir Bhutto
Benazir Bhutto. Pakistan's prime minister had her daughter Bakhtawar in January 1990 and, by her own account, was back signing files a day later; Ardern's baby arrived on 21 June, Bhutto's own birthday.
Q 30The Super Bowl trophy is named after which coach, winner of the first two with Green Bay?
Vince Lombardi
Vince Lombardi. He took over a Packers team that had won a single game the season before and made it champion five times in nine years; the trophy was renamed for him after he died of cancer in 1970.