It’s the end of June, which for many organizations marks the end of the fiscal year and the time for employee development reviews. It’s a time for managers to critique what they did (or didn’t) do to develop the capabilities of their subordinates—and a time for subordinates to reflect on how well they sought and used the counsel of wise people. In other words, June is a time to reflect on mentoring. So much of employee development entails tacit learning. “Tacit” means “by touch.” Learning by touch is gained by watching how a masterful practitioner works, by working under the observation of an excellent guide, or by unobserved trial-and-error. As banker Walter Wriston once put it, “Good judgment comes from experience. And experience comes from bad judgment.” The point of mentoring is to provide growth in tacit wisdom while forestalling some of the cost of bad judgment.
How does mentoring work? What does it require of the mentor and mentee? What are some pitfalls? What does success look like? The aim of this post is to orient your thinking about mentoring. To heighten some points, I’ve included a story that makes this post longer than usual (it will take +/- 15 minutes to read). If you are in a hurry, skip to the conclusion.
A Case of Pitfalls to Avoid
At Darden, all learning begins with a case study. In that spirit, let me offer a case based on an excerpt from Mark Twain’s book, Life on the Mississippi.[1] Published in 1883, the book recounts his experience as a cub pilot on riverboats plying the Mississippi River from 1857 to 1859, when Twain received his pilot’s license. His mentor was Horace Bixby, a well-regarded pilot. Twain continued to pilot vessels until the Civil War broke out in 1861. Written as a humorous coming-of-age story, some chapters of the book yield lessons in mentoring and the growth of tacit wisdom.
After reading the following excerpts from the book, consider these questions:
- Who took the initiative to set up the mentorship? What motivated each party?
- What was the “contract” or understanding between Twain and Bixby?
- What was Twain’s learning task?
- What was Bixby’s coaching style?
- How did Twain’s attitude change over time?
- Was this a good mentorship? Judged by what standards?
Excerpts from Life on the Mississippi
“I planned a siege against my pilot, and at the end of three hard days he surrendered. He agreed to teach me the Mississippi River from New Orleans to St. Louis for five hundred dollars, payable out of the first wages I should receive after graduating [note that $500 paid in 1857 had the purchasing power of more than $18,000 in 2025[2].] I entered upon the small enterprise of ‘learning’ twelve or thirteen hundred miles of the great Mississippi River with the easy confidence of my time of life. If I had really known what I was about to require of my faculties, I should not have had the courage to begin. I supposed that all a pilot had to do was to keep his boat in the river, and I did not consider that that could be much of a trick, since it was so wide.
Now and then Mr. Bixby called my attention to certain things. Said he, ‘This is Six-Mile Point.’ I assented. It was pleasant enough information, but I could not see the bearing of it. I was not conscious that it was a matter of any interest to me. Another time he said, ‘This is Nine-Mile Point.’ Later he said, ‘This is Twelve-Mile Point.’ They were all about level with the water’s edge; they all looked about alike to me; they were monotonously unpicturesque. I hoped Mr. Bixby would change the subject. But no; he would crowd up around a point, hugging the shore with affection, and then say: ‘The slack water ends here, abreast this bunch of China-trees; now we cross over.’ So he crossed over. He gave me the wheel once or twice, but I had no luck. I either came near chipping off the edge of a sugar plantation, or I yawed too far from shore, and so dropped back into disgrace again and got abused.
The watch was ended at last, and we took supper and went to bed. At midnight the glare of a lantern shone in my eyes, and the night watchman said–‘Come! turn out!’ And then he left. I could not understand this extraordinary procedure; so I presently gave up trying to, and dozed off to sleep. Pretty soon the watchman was back again, and this time he was gruff. I was annoyed. I said: ‘What do you want to come bothering around here in the middle of the night for. Now as like as not I’ll not get to sleep again tonight.’
The watchman said–‘Well, if this an’t good, I’m blest.’
The ‘off-watch’ was just turning in, and I heard some brutal laughter from them, and such remarks as ‘Hello, watchman! an’t the new cub turned out yet? He’s delicate, likely. Give him some sugar in a rag and send for the chambermaid to sing rock-a-by-baby to him.’
About this time Mr. Bixby appeared on the scene. Something like a minute later I was climbing the pilot-house steps with some of my clothes on and the rest in my arms. Mr. Bixby was close behind, commenting. Here was something fresh–this thing of getting up in the middle of the night to go to work. It was a detail in piloting that had never occurred to me at all. I knew that boats ran all night, but somehow I had never happened to reflect that somebody had to get up out of a warm bed to run them. I began to fear that piloting was not quite so romantic as I had imagined it was; there was something very real and work-like about this new phase of it.
…It seemed to me that I had put my life in the keeping of a peculiarly reckless outcast. Presently he turned on me and said ‘What’s the name of the first point above New Orleans?’ I was gratified to be able to answer promptly, and I did. I said I didn’t know.
‘Don’t know?’ This manner jolted me. I was down at the foot again, in a moment. But I had to say just what I had said before.
‘Well, you’re a smart one,’ said Mr. Bixby. ‘What’s the name of the next point?’
Once more I didn’t know.
‘Well, this beats anything. Tell me the name of any point or place I told you.’
I studied a while and decided that I couldn’t.
‘Look here! What do you start out from, above Twelve-Mile Point, to cross over?’
‘I–I–don’t know.’
‘You–you–don’t know?’ mimicking my drawling manner of speech. ‘What do you know?’
‘I–I–nothing, for certain.’
‘By the great Caesar’s ghost, I believe you! You’re the stupidest dunderhead I ever saw or ever heard of, so help me Moses! The idea of you being a pilot–you! Why, you don’t know enough to pilot a cow down a lane.’
Oh, but his wrath was up! He was a nervous man, and he shuffled from one side of his wheel to the other as if the floor was hot. He would boil a while to himself and then overflow and scald me again.
‘Look here! What do you suppose I told you the names of those points for?’
I tremblingly considered a moment, and then the devil of temptation provoked me to say ‘Well–to–to–be entertaining, I thought.’
This was a red rag to the bull. He raged and stormed so (he was crossing the river at the time) that I judge it made him blind. Presently he said to me in the gentlest way ‘My boy, you must get a little memorandum book, and every time I tell you a thing, put it down right away. There’s only one way to be a pilot, and that is to get this entire river by heart. You have to know it just like A B C.’
That was a dismal revelation to me; for my memory was never loaded with anything but blank cartridges. However, I did not feel discouraged long. I judged that it was best to make some allowances, for doubtless Mr. Bixby was ‘stretching.’
…By the time we had gone seven or eight hundred miles up the river, I had learned to be a tolerably plucky up-stream steersman, in daylight, and before we reached St. Louis I had made a trifle of progress in night-work, but only a trifle. I had a note-book that fairly bristled with the names of towns, ‘points,’ bars, islands, bends, reaches, etc.; but the information was to be found only in the notebook–none of it was in my head. It made my heart ache to think I had only got half of the river set down; for as our watch was four hours off and four hours on, day and night, there was a long four-hour gap in my book for every time I had slept since the voyage began.
… At the end of what seemed a tedious while, I had managed to pack my head full of islands, towns, bars, ‘points,’ and bends; and a curiously inanimate mass of lumber it was, too. However, inasmuch as I could shut my eyes and reel off a good long string of these names without leaving out more than ten miles of river in every fifty, I began to feel that I could take a boat down to New Orleans if I could make her skip those little gaps. But of course my complacency could hardly get start enough to lift my nose a trifle into the air, before Mr. Bixby would think of something to fetch it down again. One day he turned on me suddenly with this settler–
‘What is the shape of Walnut Bend?’
He might as well have asked me my grandmother’s opinion of protoplasm. I reflected respectfully, and then said I didn’t know it had any particular shape. My gunpowdery chief went off with a bang, of course, and then went on loading and firing until he was out of adjectives. I had learned long ago that he only carried just so many rounds of ammunition, and was sure to subside into a very placable and even remorseful old smooth-bore as soon as they were all gone. That word ‘old’ is merely affectionate; he was not more than thirty-four. I waited. By and by he said–
‘My boy, you’ve got to know the shape of the river perfectly. It is all there is left to steer by on a very dark night. Everything else is blotted out and gone. But mind you, it hasn’t the same shape in the night that it has in the day-time.’
‘How on earth am I ever going to learn it, then?’
‘How do you follow a hall at home in the dark? Because you know the shape of it. You can’t see it.’
‘Do you mean to say that I’ve got to know all the million trifling variations of shape in the banks of this interminable river as well as I know the shape of the front hall at home?’
‘On my honor, you’ve got to know them better than any man ever did know the shapes of the halls in his own house.’
‘I wish I was dead!’
‘Now I don’t want to discourage you, but–‘
‘Well, pile it on me; I might as well have it now as another time.’
‘You see, this has got to be learned; there isn’t any getting around it. A clear starlight night throws such heavy shadows that if you didn’t know the shape of a shore perfectly you would claw away from every bunch of timber, because you would take the black shadow of it for a solid cape; and you see you would be getting scared to death every fifteen minutes by the watch. You would be fifty yards from shore all the time when you ought to be within fifty feet of it. You can’t see a snag in one of those shadows, but you know exactly where it is, and the shape of the river tells you when you are coming to it. Then there’s your pitch-dark night; the river is a very different shape on a pitch-dark night from what it is on a starlight night. All shores seem to be straight lines, then, and mighty dim ones, too; and you’d run them for straight lines only you know better. You boldly drive your boat right into what seems to be a solid, straight wall (you knowing very well that in reality there is a curve there), and that wall falls back and makes way for you. Then there’s your gray mist. You take a night when there’s one of these grisly, drizzly, gray mists, and then there isn’t any particular shape to a shore. A gray mist would tangle the head of the oldest man that ever lived. Well, then, different kinds of moonlight change the shape of the river in different ways. You see–‘
‘Oh, don’t say any more, please! Have I got to learn the shape of the river according to all these five hundred thousand different ways? If I tried to carry all that cargo in my head it would make me stoop-shouldered.’
‘No! you only learn the shape of the river, and you learn it with such absolute certainty that you can always steer by the shape that’s in your head, and never mind the one that’s before your eyes.’
‘Very well, I’ll try it; but after I have learned it can I depend on it. Will it keep the same form and not go fooling around?’
…So that question was answered. Here were leagues of shore changing shape. My spirits were down in the mud again. Two things seemed pretty apparent to me. One was, that in order to be a pilot a man had got to learn more than any one man ought to be allowed to know; and the other was, that he must learn it all over again in a different way every twenty-four hours.
…I went to work now to learn the shape of the river; and of all the eluding and ungraspable objects that ever I tried to get mind or hands on, that was the chief. I would fasten my eyes upon a sharp, wooded point that projected far into the river some miles ahead of me, and go to laboriously photographing its shape upon my brain; and just as I was beginning to succeed to my satisfaction, we would draw up toward it and the exasperating thing would begin to melt away and fold back into the bank! If there had been a conspicuous dead tree standing upon the very point of the cape, I would find that tree inconspicuously merged into the general forest, and occupying the middle of a straight shore, when I got abreast of it! No prominent hill would stick to its shape long enough for me to make up my mind what its form really was, but it was as dissolving and changeful as if it had been a mountain of butter in the hottest corner of the tropics. Nothing ever had the same shape when I was coming downstream that it had borne when I went up.
…It was plain that I had got to learn the shape of the river in all the different ways that could be thought of,–upside down, wrong end first, inside out, fore-and-aft, and ‘thortships,’–and then know what to do on gray nights when it hadn’t any shape at all. So I set about it. In the course of time I began to get the best of this knotty lesson, and my self-complacency moved to the front once more. Mr. Bixby was all fixed, and ready to start it to the rear again. He opened on me after this fashion—
‘How much water did we have in the middle crossing at Hole-in-the-Wall, trip before last?’
I considered this an outrage. I said–
‘Every trip, down and up, the leadsmen are singing through that tangled place for three-quarters of an hour on a stretch. How do you reckon I can remember such a mess as that?’
‘My boy, you’ve got to remember it. You’ve got to remember the exact spot and the exact marks the boat lay in when we had the shoalest water, in everyone of the five hundred shoal places between St. Louis and New Orleans; and you mustn’t get the shoal soundings and marks of one trip mixed up with the shoal soundings and marks of another, either, for they’re not often twice alike. You must keep them separate.’
When I came to myself again, I said–
‘When I get so that I can do that, I’ll be able to raise the dead, and then I won’t have to pilot a steamboat to make a living. I want to retire from this business. I want a slush-bucket and a brush; I’m only fit for a roustabout. I haven’t got brains enough to be a pilot; and if I had I wouldn’t have strength enough to carry them around, unless I went on crutches.’
‘Now drop that! When I say I’ll learn a man the river, I mean it. And you can depend on it, I’ll learn him or kill him.’
…Now when I had mastered the language of this water and had come to know every trifling feature that bordered the great river as familiarly as I knew the letters of the alphabet, I had made a valuable acquisition. But I had lost something, too. I had lost something which could never be restored to me while I lived. All the grace, the beauty, the poetry had gone out of the majestic river!
…A pilot must have a memory; but there are two higher qualities which he must also have. He must have good and quick judgment and decision, and a cool, calm courage that no peril can shake. Give a man the merest trifle of pluck to start with, and by the time he has become a pilot he cannot be unmanned by any danger a steamboat can get into; but one cannot quite say the same for judgment. Judgment is a matter of brains, and a man must start with a good stock of that article or he will never succeed as a pilot.
The growth of courage in the pilot-house is steady all the time, but it does not reach a high and satisfactory condition until some time after the young pilot has been ‘standing his own watch,’ alone and under the staggering weight of all the responsibilities connected with the position. When an apprentice has become pretty thoroughly acquainted with the river, he goes clattering along so fearlessly with his steamboat, night or day, that he presently begins to imagine that it is his courage that animates him; but the first time the pilot steps out and leaves him to his own devices he finds out it was the other man’s. He discovers that the article has been left out of his own cargo altogether. The whole river is bristling with exigencies in a moment; he is not prepared for them; he does not know how to meet them; all his knowledge forsakes him; and within fifteen minutes he is as white as a sheet and scared almost to death. Therefore pilots wisely train these cubs by various strategic tricks to look danger in the face a little more calmly. A favorite way of theirs is to play a friendly swindle upon the candidate.
Discussion, Readings, and Conclusion
The friction between Bixby, the seasoned pilot, and Twain, the 15-year old cub pilot, is both humorous and a painful glimpse into mentoring. Evidently, things turned out alright: the boy finally got his pilot’s license and had no mishaps along the way. Nevertheless, there was lots of Wriston-like learning from experience. This story suggests several points about successful mentoring.
- Motivation matters. Though Twain had “skin in the game” (a sizable payment to Bixby), he seemed motivated by the romance of piloting (“the grace, the beauty, the poetry”) rather than mastery of a difficult craft. The best mentors and mentees focus on mastery rather than romance; and they take the mentoring process quite seriously. Meet regularly. Show up on time. Take notes. This is work. The best mentees really want to improve and show their willingness to work at it.
- Be selective. In her book, Lean In, Sheryl Sandberg said that she regularly declined appeals to mentor other women—her time as COO of Facebook was limited and some of the candidates wanted a protector rather than a mentor. Mentors don’t want to waste their time: the mentee’s motivation and professional potential are decisive. But mentees should weigh the same criteria: motivation and wisdom of the mentor matter hugely in the success of the effort. Many years ago I agreed to mentor a professor at another university whose teaching evaluations had plummeted, only to discover that the guy simply did not care to teach well. Twain chose Bixby because he was one of the best pilots on the river. Bixby saw Twain’s eagerness (the “siege”) he also must have seen some potential.
- Clear expectations at the outset. Mentoring is not a one-and-done conversation. It is not psychotherapy. It is not a casual acquaintance. And it is not a protector/protégé relationship. It is a process of conversation over weeks/months or even years in which the mentor and mentee exchange technical knowledge, impart constructive feedback, share insights, and lend encouragement—all for the purpose of promoting the professional development and growth of the mentee. It is a relationship of trust and confidence based on telling the truth. But the mentor is not a fixer. The responsibility for results must be the learner’s. In The Road Less Traveled, Scott Peck recounts complaining about workload to his mentor. The mentor simply replied, “Well, I can see that you do have a problem,”[3] and left it for Peck to own up to the fact that he had created the problem through his own choices. Years later, Peck wrote, “We cannot solve a problem by hoping that someone else will solve it for us.”
- There may be no easy answers. I like to teach and mentor by asking questions—this strengthens the capacity of the learners to figure things out for themselves. The aim is not to make the mentee an order-taker. Yet as any parent knows from teaching a child how to drive, there may be situations in which the mentor should offer specific directions. In the story, Bixby monitored Twain, giving him the wheel and apparently leaving him alone (but standing behind a chimney to watch Twain)—but Bixby’s shouting and profanity yield poor exemplars for most professional settings.
- Be sensitive to differences: gender, age, seniority, race, and so on. The aim should be to help the learner find a resonant professional style consistent with their own strengths, rather than to clone what works for the mentor. To achieve that outcome, the mentor has to know the mentee very well: what are the person’s strengths and weaknesses, values, and skills?
- In the culture. As a novice instructor, new to Darden, I benefited from yearlong mentoring by a senior colleague, Professor William W. Sihler. We taught different sections of the same required first-year course. I sat in on all of his classes, and he sat in on all of mine. We shared teaching notes with each other and debriefed on the experiences. Some 40 years later, I handed off my long-standing second-year elective to a junior colleague: I observed every one of his classes (by video during the COVID pandemic) and talked with him each Friday to discuss the week’s classes and plans for the next week’s classes. For years, this kind of engagement between senior and junior colleagues has been common practice at Darden. Colleagues at other universities balk at the huge commitment that peer-to-peer mentoring takes. Yet mentoring is part of the secret sauce that sustains Darden’s mission, student-centered culture, and strategic position in the field of business schools. A mentoring effort is probably not sustainable over the long run without strong support among professional peers and strong beliefs that it will and must occur for the good of the institution and the individual. It must be part of the expectations for professionals that their work should include this activity. It should be part of the implicit contract for novice professionals that they participate. Annual performance reviews should acknowledge efforts in a mentoring process. Professional assignments should anticipate mentoring opportunities. It helps if the mentor is working in parallel on the same challenges as the learner. This would occur, for instance, if they naturally engage in consultation about their work. There, the mentor has a true incentive to replicate the learner’s work in parallel, compare notes in real time, and debrief shortly thereafter.
There is considerably more to be said about mentoring beyond the scope of this already long post. Suffice it to say, the literature on mentoring is huge. Here are some resources that have helped to shape my thinking on the subject:
- Maxwell, John C., 2008. Mentoring 101: What Every Leader Needs to Know, New York, NY: HarperCollins.
- Two books help to illustrate the process of mentoring and change leadership:
- Cottrell, David, 2002. Monday Morning Leadership: 8 Mentoring Sessions You Can’t Afford to Miss, Cornerstone Institute.
- Goldratt, Eliyahu, and Jeff Cox, 2024. The Goal: A Process of Ongoing Improvement. North River Press. This is a classic, used at Darden and many other business schools.
- Sandberg, Sheryl, 2013. Lean In: Women, Work, and the Will to Lead, New York, NY: Knopf. By the former CEO of Facebook (now Meta), it focuses particularly on the professional development of women, giving good attention to the role of mentoring.
- McCormick, David, and Dina Powell McCormick, 2025. Who Believed in You: How Purposeful Mentorship Changes the World, New York, NY: HarperCollins. Written by a “power couple,” (David was formerly CEO of Bridgewater Associates and now2 serves as U.S. Senator, while Dina was President of the “10,000 Women” initiative at Goldman Sachs and now chairs the Robin Hood Foundation) the book focuses on mentors and why leaders should devote time and effort to mentoring in their organizations.
- Ferrazzi, Keith, and Tahi Raz, 2-14. Never Eat Alone, Expanded and Updated: And Other Secrets to Success, One Relationship at a Time, New York NY: Crown. This book is less about formal mentoring, and more about connecting with other people. However, I suggest it here because the core of mentoring is gaining feedback. In the absence of gaining a formal mentor, engaging actively with others might help one gain perspective and fresh ideas on one’s own development.
[1] Excerpts are drawn from Chapters 6 through 14 of Mark Twain’s Life on the Mississippi in the digital version at Project Gutenberg. Copies can be downloaded free of charge from Project Gutenberg at gutenberg.org/cache/epub/245/pg245.txt, or from Hathi Trust at https://babel.hathitrust.org/cgi/pt?id=coo1.ark:/13960/t9x06p42z&seq=9.
[2] According to “CPI Inflation Calculator” at https://www.officialdata.org/us/inflation/1857?amount=500.
[3] M. Scott Peck, The Road Less Traveled: A New Psychology of Love, Traditional Values and Growth, 25th anniversary edition (New York: Simon & Schuster, 2003), 40.