How to Say Hard Things Gently

by Derrick G. Jeter

Intelligence, candor, and goodwill are the marks of a good conversation. Have you ever sat down with someone to discuss a topic and they where either ignorant about the subject, seemed to hedge and fudge in their language, or were haughty or indifferent to your perspective? They are usually talkative, but communicate very little. Whenever I encounter one of these small minded people I think of Abraham Lincoln’s quip: “He can compress the most words into the smallest ideas of any man I ever met.” [1]


When it comes to difficult conversations these three qualities—intelligence, candor, and goodwill—are especially important. All of us have been involved in difficult conversations . . . that is unless you were raised by hyenas, have never held a job, never dated anyone, or never had a single friend in your life.


For the rest us, we know that sinking feeling in the pit of our stomachs when we have to sit down and have one of those conversations where hard things must be said. I came across this letter, written by Eleanor Roosevelt to her forty-two-year old son, James, who was about to run for the governorship of California. He had notified the family that he and his wife, Rommie, wished to be removed from everyone’s Christmas gift list.


Sept. 22, 1949


Dearest Jimmy:


I am deeply hurt by your letter of the 16th and also frankly I was very angry. Through all the years Christmas at home was a joy to me and I hoped I had given to you all the feeling that it was a time for thinking of others even if we were far apart. It is never a burden to me. If you and Rommie find the expense too great or the burden too great of thinking beyond each other and the children, I shall accept your decision. In fact now no presents from you would be acceptable but I think it strange that you want to deprive me and others of the pleasure of thinking and showing our thought of you and your children in a tangible way.


This is the kind of high-handed, pompous action which loosens family ties and does not bind them closer. . . .


My love to you, dear



After receiving the letter, Jimmy wrote and asked the family to “forget we ever mentioned the subject.” [2]


Mrs. Roosevelt was not a mother to be trifled with. She could deliver it with the bark off!


Aristotle said there are three aspects to persuasion: pathos—the passions of emotion, logos—the logic of reason, and ethos—the character (goodwill) of the persuader. [3] This is not manipulation or deception. Persuasion is truthful. And I assume you have sufficient goodwill with the one you wish to persuade, especially when engaged in difficult conversations. So if you find yourself in a situation in which you have to say hard things to someone, here are a few techniques to help you say them gently.


First, to persuade others you must appeal to a higher purpose. Abraham Lincoln said it well:


When the conduct of men is designed to be influenced, persuasion, kind, unassuming persuasion, should ever be adopted. It is an old and true maxim, that a “drop of honey catches more flies than a gallon of gall.” So with men. If you would win a man to your cause, first convince him that you are his sincere friend. Therein is a drop of honey that catches his heart, which, say what he will, is the great high road to his reason, and which, when once gained, you will find but little trouble in convincing his judgment of the justice of your cause. If indeed that cause really be a just one. [4]


Second, to persuade others you must praise them. This is not flattery, but sincerity. It is, in the words of Fred Smith, “steam that rises from a warm heart.” [5] To persuade others you must recognize their good or you have no bases for your appeal.


Third, to persuade others you must appeal on a personal level. This is Aristotle’s pathos. Kenneth McFarland eloquently said, “What is in the well of your heart will show up in the bucket of your speech.” [6]


Fourth, to persuade others you must appeal to their reason. This is Aristotle’s logos. Peggy Noonan, a woman who knows a thing or two about writing persuasively, astutely observed:


Nothing is more beautiful, more elevating, more important in a speech than fact and logic. People think passionate and moving oratory is the big thing, but it isn’t. The hard true presentation of facts followed by a declaration of how we must deal with those facts is the key. [7]


Finally, to persuade others you must use the right words. Mark Twain said it well:


A power agent is the right word. Whenever we come upon one of those intensely right words in a book or a newspaper the resulting effect is physical as well as spiritual, and electrically prompt. [8]


There are many ways to handle difficult conversations. In a letter to Ms. magazine, a disgruntled wife, fed up with her chauvinistic husband wrote:


Dear Ms.


After working full time and attending ten hours of evening classes each week, I can’t begin to describe the rage I feel when performing 100 percent of the household duties—not to mention being zoo-keeper for an overly energetic Great Dane and a cat—while my husband leisurely reads.


Because numerous discussions on this matter have not changed the situation, I am continually searching for new tactics to help him see the folly of his ways.


In the meantime, I have found that the occasional lacing of his dinner with the cat’s food has done wonders for my spirit. Bon appetite!


Name withheld [9]


That’s certainly one why to handle a difficult conversation. But perhaps a better way is to appeal to a higher purpose, to praise, to appeal on a personal level and to reason, and to use the right words.


But if all else fails . . . there’s always the cat food!



[1] Abraham Lincoln quoted in James C. Humes, The Wit and Wisdom of Abraham Lincoln: A Treasury of Quotations, Anecdotes, and Observations (New York: Gramercy Books, 1999), 178.

[2] Eleanor Roosevelt, quoted in Dorie McCullough Lawson, Posterity: Letters of Great Americans to Their Children (New York: Doubleday, 2004), 199–200. James Roosevelt quote, Posterity, 200.

[3] See Aristotle, The Art of Rhetoric, trans. J. H. Freese (Cambridge, Mass.: Harvard University Press, 1926, reprint 2000), I, 2:3-4.

[4] Abraham Lincoln, “Temperance Address,” The Collected Works of Abraham Lincoln, vol. 1, ed. Roy P. Basler (New Brunswick, NJ: Rutgers University Press, 1953), 273.

[5] Fred Smith, You and Your Network: Getting the Most Out of Life (Waco, Tex.: Key-Word Books, 1984), 198.

[6] Kenneth McFarland, Eloquence in Public Speaking: How to Set Your Words on Fire (Englewood Cliffs, NJ: Prentice-Hall, 1961), 49.

[7] Peggy Noonan, “Just the Facts,” The Wall Street Journal, January 27, 2003, http://www.peggynoonan.

com/article.php?article=135, accessed 12 April 2008.

[8] Mark Twain, “William Dean Howells,” The Complete Essays of Mark Twain, ed. Charles Neider (New York: Da Capo Press, 2000), 400.

[9] Anonymous, “A Fed-Up Wife to Ms. Magazine,” quoted in Letters of a Nation: A Collection of Extraordinary American Letters, ed. Andrew Carroll (New York: Broadway Books, 1999), 270.