The Role of an Advisor

Leadership may feel like an individual pursuit, but you can't go it alone


“It is very lonesome at the summit!”
“Like a man's life, when he has climbed to eminence.”
— Nathaniel Hawthorne, 1860


Since humans first began telling stories to each other, we've been enamored with heroes.

From early epic poems like Gilgamesh in second millennium B.C. Sumeria and The Iliad and The Odyssey in 7th century B.C. Greece, we've allowed our imaginations to wander and to live vicariously through the lives of fictionalized heroes.

These beings of light and air do things we find ourselves incapable of doing. They succeed where we can't. They give us hope when there is none.

Consider how the legendary General Motors speechwriter and first editor of The Baker Street Journal Edgar W. Smith described the admiration of devotees of Sherlock Holmes:

"[H]e stands before us as a symbol – a symbol, if you please, of all that we are not, but ever would be. His figure is sufficiently remote to make our secret aspirations for transference seem unshameful, yet close enough to give them plausibility. We see him as the fine expression of our urge to trample evil and to set aright the wrongs with which the world is plagued. He is Galahad and Socrates, bringing high adventure to our dull existences and calm, judicial logic to our biased minds. He is the success of all our failures; the bold escape from our imprisonment."

Isn't this something we do with most heroes in history and literature? We admire their courage. We stand in awe of their wisdom. We celebrate their resilience.

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We wonder if we could be like them, or some part of them, if only for a moment, fleeting and fanciful as it might be.

We return to these stories again and again, finding them as comforting and comfortable as an old sweater, pulled on with the ease of muscle memory, warming our hearts.

Our heroes are often both distant yet relatable. Their special powers or the situation in which we find them may be unattainable or unrealistic, but if we look closely, we find glimpses of humanity—perhaps foibles and flaws—that give us hope that one day we might improve our own lot.

These brief snatches of their fallibility are gifts bestowed upon us by individuals who play an important but understated role in our heroes' lives: their sidekicks.

Perhaps "sidekick" is an imperfect word to represent their role. Sidekick connotes an inferior or a hanger-on, a buddy or buffoon rather than an equal.


“It may be that you are not yourself luminous, but you are a conductor of light.” — Arthur Conan Doyle, 1901


Thanks to his portrayal of Dr. Watson in 14 Sherlock Holmes films in the 1940s, Nigel Bruce permanently damaged the reputation of the sine qua non of sidekicks, taking a respected medical man and devolving him to the genus Boobus Britannicus.

Holmes wasn't the most warm-hearted of literary heroes, and his extreme intelligence comingled with his curt manner, drawing a further distinction between himself and his colleague. He managed to utter some back-handed compliments, but at the same time he indicated how essential he considered the man whom he called "my friend and colleague, Dr. Watson."

And thus, elevating his flat-mate to colleague status, Sherlock Holmes conferred upon his sidekick a more significant role.

Advisors keep us grounded. They act as a sounding board, listening as the leader bounces theories off of them and simply thinks out loud. Trusted advisors provide counsel, keeping leaders on a path that connects their execution to their vision. They're a source of encouragement and commiseration, when a leader doesn't have equals in an organization to turn to.

Turning to literature, here are some examples of what such counsellors-cum-confidantes do for their colleagues.

They keep us focused.

Sherlock Holmes knew that he had a powerful ally in Dr. Watson. He was not only his biographer (and therefore public relations man), but he added a perspective that Holmes himself couldn't appreciate by himself. From a storytelling perspective, Conan Doyle gave us a narrator to whom we can relate. We admire Holmes's powers, but we identify with Watson's voice.

“I am lost without my Boswell.” — Arthur Conan Doyle, 1891


They remind us of the importance of establishing, developing and maintaining relationships.

Speaking of Boswell and relationships… James Boswell was the famous biographer of Samuel Johnson, the lexicographer, writer, and distinguished man of letters. He was odd to some and heavily focused on his work. But he realized the power of relationships, and his friendship with Boswell was essential for telling his story more widely. 

"If a man does not make new acquaintance as he advances through life, he will soon find himself left alone. A man, Sir, should keep his friendship in constant repair." — Samuel Johnson, 1755


Advisors help keep our egos in check.

The vivacious and idealistic Don Quixote was perfectly complemented with the everyman  Sancho Panza. This humble squire kept his don rooted in practicality, making his point with his humor, application of proverbs, and earthy wit. At times, we all need to be reminded that humility is an endearing and powerful attribute of leaders.

"Modesty is a virtue not often found among poets, for almost every one of them thinks himself the greatest in the world." — Miguel de Cervantes, 1615


They teach us to be patient teachers, lifelong students, and servant leaders.

When Robinson Crusoe was stranded on an isolated island, he thought he had all he needed: shelter, supplies, food. And yet, he came to realize that he missed companionship. Upon meeting a savage who had also been stranded, he gave him the name Friday and began to teach him the English language and hunting skills, among other things. It took weeks and months to make headway, but he stuck with it.

At the same time, Crusoe realized Friday had much to teach him as well. He learned everything he could from his newfound companion, from topography to culture, and his own backstory. Even though he was white, he grew to accept that he could serve Friday as much as Friday could serve him.

"I had been so near obtaining what I so earnestly longed for—somebody to speak to, and to learn some knowledge from them." — Daniel Defoe, 1719


Heroes get most of the attention, yet their companions fill roles that make them essential not only to the heroes, but to us as well. They are confidantes and advisors, scribes and consciences, colleagues and consiglieres.

And to those around them, they are storytellers. They translate the actions of leaders to lessons we can take to heart.

However, they don't just show up on your doorstep or arrive through a cold call or email. Advisors who are worth every penny are those whom you trust. A trusted advisor is the one whom you'd call with a concern at two o'clock in the morning. The one who isn't afraid to tell you you're wrong. The last person in the room before you make the decision.

Every leader needs an advisor and confidante.

I’ll be back on Friday with another essay and links to helpful resources for paying subscribers. Are you one yet?

Thanks, and I’ll see you on the internet.


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