Thomas Jefferson’s 7 Step Guide to Successful Emails

Applying Jefferson’s Letter-Writing Skills To Your Outbox

Thomas Jefferson never actually wrote emails, but he did write 19,000 letters. With inflation, that’s almost 260,000 emails today.

In his biography Thomas Jefferson: The Art of Power, Jon Meacham looked at a particular letter from 1775 where Jefferson used his mastery of language and manipulation to turn an opponent into a strategic asset.

Blood had already been spilled in the Revolutionary War, and Jefferson’s Loyalist cousin John Randolph was packing his bags for the motherland. Using his letter-writing kung-fu, Jefferson wrote his king-loving cousin what seemed like a friendly personal note but was in truth a shrewd political play to change Britain’s perception of America.

I dig deeper into that letter to uncover the psychological techniques Jefferson employed two hundred years ago, and I lay them out in a step-by-step manual you can use today in emails, direct messages, and texts. Following Jefferson’s lead, it’s possible to not only get others to do what you want, but like it.

Step 1: Ask about something they love.

Jefferson started his letter by bringing up Randolph’s fine violin, which he was selling to Jefferson, and recommending material to wrap it. This created an instant feeling of familiarity and connection much more effective than a generic “hope you’re doing well,” and it was a nice disarming move that subtly said we care about the same things, so we must be on the same side.

This tactic isn’t about fooling anyone. People know when you’re writing because you want something, but making that extra effort upfront to connect with them personally will put them in a better mood to give it to you.

When to ask about something they love:
● If it’s been a while since you’ve written and you want to set a friendly tone.
● When you want to hide your sociopathic lack of interest in other humans.

When not to do this:
● When your message is so short it seems insincere: “Hi Steve, how’s your indoor soccer league going? Can I have one of your kidneys?”

Step 2: Pretend you don’t want to get involved.

Like George Washington and Michael Jordan, one of Jefferson’s greatest skills was false retirement. He told Randolph his second wish (his first being a restoration of America’s just rights) was:

“a return of the happy period, when, consistently with duty, I may withdraw myself totally from the public stage, and pass the rest of my days in domestic ease and tranquility, banishing every desire of ever hearing what passes in the world.”

Fat chance. This was a year before he wrote the Declaration of Independence, and 26 years before he became president. He very much wanted to get involved, but to be a successful politician back then you had to pretend you wanted nothing to do with politics and all you really wanted to do was farm.

Thomas Jefferson loved to watch his slaves farm.

You can enjoy the benefits of this attitude too, because nothing lends a greater illusion of importance and objectivity to your message than acting like you didn’t want to have to write it in the first place. Circumstances required you to step in and take action. You’re a reluctant hero, like John McClane in Die Hard. Or better yet, Danny Glover in Lethal Weapon, who is actually a perfect metaphor for Jefferson’s political career. Both groaned “I’m too old for this shit” when they still had at least three sequels ahead of them.

When to pretend you don’t want to get involved:
● When it’s bad news or not really your business but you can’t help yourself.

When not to do this:
● Thank you notes and cover letters.

Step 3: Set out to clear up confusion.

The world is a scary and confusing place. Or it was until you came along, Reluctant Hero. By stepping in and declaring, “I just want to clear up any confusion” or “I want to make sure everyone’s on the same page,” you offer everyone a beacon of hope guiding them to the safe haven of your Utopian world of understanding and clarity. Of course what you’re really saying is, “This is all just a misunderstanding that can be cleared up by you doing what I say.”

Jefferson’s entire purpose was to clear up Britain’s confusion and make sure they knew America was totally united and totally badass:

“I think it must be evident to yourself, that the Ministry have been deceived by their officers on this side of the water, who (for what purpose I cannot tell) have constantly represented the American opposition as that of a small faction, in which the body of the people took little part. This, you can inform them, of your own knowledge, is untrue. They have taken it into their heads, too, that we are cowards, and shall surrender at discretion to an armed force. The past and future operations of the war must confirm or undeceive them on that head.”

He wanted Randolph to pass on the message that America was a serious threat, but he did it by presenting himself like a wise family doctor prescribing a gentle laxative: friendly, knowledgeable, and there to help when you’re full of crap.

When to clear up confusion:
● When misperceptions might be hurting you.
● When an email chain becomes so tangled and confusing it needs a reset.
● When the strength of your revolutionary forces are underestimated.

When not to do this:
● When you could achieve the same thing by saying nothing.

Step 4: Stress how they are the chosen one.

After buttering his cousin up with fancy violin talk and making it clear his cause was important enough to stop farming and pick up his pen, Jefferson focused on what he wanted Randolph to do. He told him, “looking with fondness towards a reconciliation with Great Britain, I cannot help hoping you may be able to contribute towards expediting this good work.” Positive words like fondness, reconciliation, and good elevate Jefferson’s real message of “Be my willing pawn and do my bidding, quickly.”

Singling out your recipient and letting them know exactly what to do is key. This is why I’ve never started a forest fire; Smokey the Bear was very specific about my role in preventing them, and I was so flattered he recognized my special talent for not committing arson that I continue to oblige him to this day.

Jefferson was telling Randolph, “Only you can prevent revolutionary wars.” Spoiler alert: Randolph couldn’t pull that off. But he did manage to get Jefferson’s letter to the British Secretary of State for the Colonies. Through flattery, manipulation, and the keen ability to predict his audience’s response, Jefferson got a personal letter to his cousin all the way up the ranks of the British empire.

When to stress they are the chosen one:
● When you want one person to do something they’re uniquely positioned to do but might not realize it.

When not to do this:
● When it’s already obvious how they can help and restating it makes you look like an idiot for telling them what their job is.

Step 5: Lay out the stakes, and the consequences.

Jefferson expressed his desire for Randolph to spread the word about America’s unity and strength. Now, he had to explain why this was necessary. He did that by making it clear what hung in the balance – Britain’s place on top of the world:

“it will, perhaps, be in your power…to render service to the whole empire, at the most critical time, certainly, that it has ever seen. Whether Britain shall continue the head of the greatest empire on earth, or shall return to her original station in the political scale of Europe, depends, perhaps, on the resolutions of the succeeding winter.”

If you’re asking for something important, your audience wants to know why it’s important to you, what’s in it for them, and what’s at stake. Jefferson made it clear helping him meant helping Britain, too, and that reconciliation (still a possibility at that point) was in everyone’s best interest. But, Jefferson warned, if it wasn’t the kind of hands-off reconciliation he wanted, he “would lend my hand to sink the whole Island in the ocean.”

Also money. Oh, and cannons! Money and cannons, those are very important. And ships, too. But the ships had cannons on them, so do I count both? Actually the ships probably had everything else on them, too. So there we have it: money, cannons, and ships, plus what’s in the picture. Those are the weapons that won the American Revolution.

Your stakes and consequences may vary. If it’s a corporate email you can stress the impact on the bottom line. How much money can this initiative save? How much revenue is at risk if this project isn’t completed? How old is Danny Glover, and does that number truly exceed the maximum value for this shit?

When to lay out the stakes and consequences:
● If the stakes aren’t already clear, or you have compelling reasons for asking for something that won’t make you look bad.

When not to do this:
● Don’t threaten people or give them ultimatums in writing. That’s best handled in unrecorded conversations.
● Love letters. People are much more attracted to confidence than a list of bad things that could happen if they won’t go out with you.

Step 6: Ask a small favor.

This tip might be the easiest and most effective if done right.

In the post-script of his letter, Jefferson changes the subject completely by asking if Randolph might be willing to sell him some of his books: “P.S. My collection of classics, & of books of parliamentary learning particularly is not so complete as I could wish. As you are going to the land of literature & of books you may be willing to dispose of some of yours here & replace them there in better editions.”

What he is really doing is employing a psychological phenomenon later known as the Ben Franklin effect. As Franklin put it in his autobiography, “He that has once done you a kindness will be more ready to do you another, than he whom you yourself have obliged.” Franklin recounted how he completely won the favor of a political rival by asking him to borrow a “certain very scarce and curious book” from his library.

Two things are clear from these examples – 1) books are powerful things, and 2) our country owes its existence to some brilliant conniving bastards.

People love doing things for others when it’s easy, and especially when it appeals to their intellectual vanity. The thinking goes that if you do something nice for someone, your brain tells you that you must like them. You can try this technique, sparingly, to help people associate doing things for you with warm fuzzies.

When to ask a small favor:
● With people you haven’t dealt with much directly, so you can shape their perception of you.
● If you’re borrowing something you know you’re going to take care of and return promptly.

When not to do this:
● When the favor doesn’t require their unique resources or knowledge.
● If the favor involves driving you to the airport. That’s not giving anyone warm fuzzies.

Step 7: Remove salt and add sugar.

In Jefferson’s time, people made two copies of every letter – one to send and one to keep. By the time they wrote the second copy, they had a chance to rethink their words. Jon Meacham found that Jefferson deleted an “interesting threat” from the version he sent off.

If Britain took over the existing colonies, Jefferson said it could “mean the dereliction of our lower Country and establishment beyond the mountains.” The sentence was likely cut because the if-Britain-wins contingency wasn’t relevant to his main purpose, and threatening to run for the hills didn’t sound very badass.

Whenever I’m writing an important email, I always add the recipient’s email address last. That way there’s no way I can possibly screw up and send the email before I’m finished with the final stage: sugarcoating. This is your chance to remove anything that’s not relevant to your main point and soften any harshness or emotion that could overshadow your objective.

Sugarcoating isn’t about watering down your message – it’s about managing your audience’s reactions. You don’t want to sound angry, and you don’t want to make the other person angry. Whether you’re removing the profanity from an office email or proofreading your fiancee’s passive-aggressive texts to her mother during the wedding planning process, your life will be easier when you realize anger doesn’t get things done. You might think, “sure it does, people do what I want when I yell at them!” Maybe they do, but guess what? They hate you, and there are a billion things they’re not doing for you because you’re an asshole.

Jefferson knew the pen was mightier than the sword and must be wielded responsibly.

Thomas Jefferson cared too much about his popularity to alienate others in writing. If you find yourself in a situation where you need to say something truly nasty, you can always do what he did – have James Madison or someone else say it for you.

When to sugarcoat:
● Always.

When not to do this:
● Never. If your message is important, it deserves better than your first draft.


Sources: Thomas Jefferson: The Art of Power by Jon Meacham
Jefferson the Virginian by Dumas Malone



  1. Anonymous
    September 20, 2014 / 7:52 am

    I so enjoyed reading and relating to this piece.Excellent and full of good advice. Your perception of our founding fathers shows us the act of communication and how urgent it was that people conveyed the proper tone-of-voice in their correspondence. I also liked the way you threw in those tidbits of humor, which were quite unexpected the first go round, but were a happy thing to find throughout this post. You have a true gift of gab and the way you toss in and shake about the history of these men is spot on!

    • Howard Dorre
      September 21, 2014 / 9:23 pm

      Thank you so much for the kind words! I could go on and on about the process of letter-writing back in the day, and the strategic role it played in everything from love to war. Thank you for reading!

  2. J.J.
    September 22, 2014 / 12:18 am

    Excellent read. Jefferson was a man of many talents, like so many of the early were. Your discussion of his writing abilities reminded me of how he came to be appointed the primary writer of the Declaration of Independence. Adams was the chair of the Drafting Committee, but fully admitted that Jefferson was a better writer and more beloved by the people. Who knows how the course of history would have changed had Adams written the first draft, or appointed another to do so. By the way, I love the pictures in this post as well as your others. Very funny!

    • Howard Dorre
      September 22, 2014 / 5:17 pm

      Thank you for reading! I imagine if Adams had written the first draft of the Declaration, it would definitely have been…longer. Since the act itself was far more celebrated in its time than the declaration itself, I'm not sure how much it would have changed history, except maybe for Adams himself. It may have improved his popularity and legacy. I also wonder what impact dying on the same day as Jefferson had on his legacy — did it elevate him in the people's eyes to Jefferson's level of reverence, or did Jefferson overshadow him in death as he had in life?

  3. dogg724
    September 26, 2014 / 8:13 am

    This is a killer post. Such a strong premise for a blog to begin with and your take on the actual history is relevant, helpful, and correct. I wait until I can actually focus on what you write. That's my way of saying "you're shit kicks ass keep it up."

    • Howard Dorre
      September 26, 2014 / 5:26 pm

      Wow, thank you so much, I'll do my damnedest to keep kicking ass!

  4. Matt Neylon
    August 25, 2020 / 5:56 pm

    Where else can you find Thomas Jefferson and Smoky the Bear in the same story
    Well done again

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