60% of new managers fail within the first 24 months of their promotion.

Most managers are not set up to win. Instead many are promoted into management because of their exemplary skills as task executors. Organizations that pay no attention to management-specific skills when promoting individual contributors into management set their managers up for failure.

Challenges

One of the most charismatic engineers I’ve ever worked with used to say “Skill issue, get good!” whenever a technical solution was flaky. The advice also applies to leadership skills. There is a plethora of information on the tactics and strategy of leadership, so why do otherwise clever people fail at it? Their perspective is incorrect. If one seeks leadership opportunities for self-aggrandizement, money, or any other such weak and transitory reason, they will certainly fail, even if they have a Harvard MBA!

Conversely, those who make a public show of self-sacrifice for their employees and get dragged down into the implementation and execution that should be delegated to their lieutenants, also fail. This group prostrates themselves for the former group to use as a stepstool to their next venture. These “humble leaders” suffer greatly to retain the moral high ground (at least publicly, they are even more self-serving than the first group) and little else of note.

One Way In

Authenticity is the only way to succeed as a leader. This lesson is painless if one enters leadership with authenticity. Those who reform later on in their journey experience much pain from the messy work of severing their mask from their true face.

The one hope of Rome, L. Quinctius, used to cultivate a four-acre field on the other side of the Tiber, just opposite the place where the dockyard and arsenal are now situated; it bears the name of the ‘Quinctian Meadows.’ There he was found by the deputation from the senate either digging out a ditch or ploughing, at all events, as is generally agreed, intent on his husbandry. After mutual salutations he was requested to put on his toga that he might hear the mandate of the senate, and they expressed the hope that it might turn out well for him and for the State. He asked them, in surprise, if all was well, and bade his wife, Racilia, bring him his toga quickly from the cottage. Wiping off the dust and perspiration, he put it on and came forward, on which the deputation saluted him as Dictator and congratulated him, invited him to the City and explained the state of apprehension in which the army were.

– Livy, Ab Urbe Condita, Book 3, Chapter 26

Lucius Quincticus Cincinnatus was a farmer during the early years of the Roman Republic (519-430 BC). He came from a patrician family and had served as a consul but preferred a simple life close to nature. When a neighboring tribe, the Aequi launched an invasion surrounding a Roman army on Mount Algidus in 458 BC, Rome called upon her servant Cincinnatus. The Roman Senate, realizing the need for swift and decisive action to save their doomed soldiers, granted Cincinnatus the role of temporary dictator for a period of six months. Temporary, it must be noted, was a bit of a misnomer, as a dictator wielded total power over Rome and thus could refuse to cede their position. Cincinnatus heeded Rome’s call, he wiped the dust and sweat from his face, donned his toga, and accepted his role as dictator.

Working on a farm has less bullshit (colloquially speaking at least) than any other job in civilized society. The results of one’s actions directly provide sustenance or starvation. Participating in this process liberates one’s attention from trivial things such as appearances or norms. Cincinnatus embodied this spirit, deciding to focus only on what was important. Cincinnatus assembled an army and decisively defeated the Aequi. Just 16 days after becoming dictator, Cincinnatus abdicated his powers and returned to his farm.

Takeaway

The best leaders are simple minded. They avoid accepting unnecessary power knowing that it is a force multiplier for both good and bad ideas equally. Instead of focusing on accumulating power, they focus on developing a discernment for what is necessary and unnecessary. It is out of this discernment that they are able to shamelessly accept power when there is a necessity.

Strive to become like Cincinnatus. Out of a deep connection with the direct results of his actions, he developed a keen sense of what was authentic and what was bullshit. What results out of this refined sense isn’t courage, it is simply an inability to agree and be complicit when someone says that 1+1=3.