Self Improvement

How to Email Like a Pro to Get Shit Done – The Mickey Way

I used to have a boss who didn’t understand email. The root problem was that he neither understood correspondence, nor the art of conversation. How he got to be my boss remains a mystery (but I have a few theories). So…

What didn’t he understand about email, you ask?

My boss thought that email worked fine if you typed all your thoughts into a single paragraph, using only an occasional period for punctuation. Furthermore, he wrote the entire email in ALL CAPS, which is off-putting at best.

I frequently rewrote his email for him. It never occurred to him that he should learn to correspond in any other fashion. He hardly believed me when I told him the email needed to be rewritten. (Of course, he did believe me because he returned for help, and sent my version as his own. He just never admitted he was wrong or thanked me for helping.)

This is not about sales or marketing

A lot has been written about email to make sales or expand your marketing reach. This article is about advancing projects, solving problems and getting stuff done when it’s your job on the line.

I’ve been working for 35 years, since before email, and have evolved and adapted to make email an effective and reliable tool that helps me do my job. Using the techniques I describe, you will worry less and produce more. And it’s no more difficult than having a conversation.

First things first: what is email?

Email is a form of correspondence, and correspondence is the one-sided form of conversation. When you converse (or correspond) with someone, you bring up a topic, you listen to their thoughts on the topic, and you share your own thoughts. If a decision (or action) is required, you then base the decision on the thoughts just shared with the other person.

At the risk of being pedantic, those principles of conversation are:

  • Bring up a topic
  • Listen to the thoughts and opinions offered
  • Share your own thoughts and opinions
  • Suggest a decision (or action) if one is needed
  • Confirm agreement (if needed)

That pretty much covers how all human civilization arranges and advances itself. When you send an email, you are participating in human civilization. But, being one-sided by its nature, it’s even more important to be exactly clear in an email about:

  • Topic
  • Your thoughts and opinions
  • Whether or not a decision is needed

As tempting as it may be to avoid confrontation, or to be chatty, don’t do any of that stuff. Stick to the topic and ask tough questions if needed. Tangential thoughts may ruin your chances of getting an answer. Most business correspondence is done via email, so it’s imperative that you are skilled in it if you want to flourish in your work.

Business conversations should be focused on reaching (or sharing) a decision, leading to an action for the business. Email is a great way to have those conversations, allowing the participants to respond at their convenience.

Here are a few rules for business email done The Mickey Way:

Rule #1: Put the topic in the subject of the email

Email has a subject line that’s displayed for all recipients. Put the topic of this one-sided conversation there. Write it in a clear and interesting way because this is your first and best chance to get the opinion, decision or action you need for your business.

Don’t reuse an old email’s subject line because you can reply-all and send it to a particular group. Go ahead and hit reply-all, but take the time to put the correct topic in the subject line.

Rule #2: Greet the recipient in the body of the email

Email has a To field which specifies one or more recipients. If the To field is crowded with names, most people will think somebody else is going to deal with email. This is called the Bystander Effect.

The Bystander Effect is when people witnessing an accident, crime or disaster will assume that someone else is going to take care of it.

You must combat the Bystander Effect by naming your intended in the body of the email. It’s best to do this as a greeting. Make it absolutely clear who you are talking to. This gets their attention, and is the next best chance to get what you need out of this email. It’s best to keep it simple, and here are three examples:

  • Dear Tom,
  • Felix:
  • Hey Bethany…

Don’t salute them with “Hey girl,” or “How are you?” or “What up?” Use a name. Use the name of the person whose attention you seek.

Rule #3: Repeat the topic in the first sentence of the email

Email is one-sided, so it’s your responsibility to share your thoughts and opinions on the topic to be discussed. But the recipient may have already forgotten the topic of the mail (which they saw in the subject line) by the time the email opens. I’m not kidding: it’s better to assume the recipient is under a constant bombardment of interruptions, and may forget in the two seconds it takes to double-click an email and begin reading it.

Often, people are skipping through email, trying to find high-priority things they need to do, and are just glancing at the sender and the body. The subject line may only get a cursory glance.

You must set the recipient’s context for this conversation by telling them the topic. Remind them why this topic is important. Tell them what’s at stake if they mess this up.

Here are a few examples:

  • Last week, I was asked to document the user interface requirements for the new cash processing system under development. You’re the designated subject matter expert on cash processing, so I need to speak to you about those requirements.
  • I received a call from our custodial vendor regarding the change in schedule for cleaning the bathrooms. It’s ultimately your decision, so I’m reaching out to you.
  • I’d like to take next Friday off on vacation

Don’t begin by asking about their weekend, or lamenting that you missed lunch the other day. If you don’t immediately hook them they are vulnerable to interruptions, and may never get back to your email.

Rule #4: Solicit the recipient’s opinion

It’s important to activate the recipient’s thinking on the topic, and the best way to do that is ask them what they think. Following on the examples from Rule #3, here are some ways to do that:

  • Do you think we should meet and discuss the requirements, or can we exchange the requirements document and develop them that way?
  • Do you have a plan for the bathroom cleaning schedule, or do you need more time to consider?
  • Do you think it would be okay for me to be gone next Friday?

Exception to the Rule

You may be informing someone of a situation, but no decision or action is needed. In that case, tell them that explicitly:

  • This is just for your information. We don’t have to decide this matter now, but I wanted you to be informed. I’ll let you know as things develop.

Don’t muddle the topic with mitigating factors; i.e., don’t give the recipient a reason to withhold their opinion. You might do this unconsciously because you are conflict adverse and regret putting the recipient on the spot by asking their opinion. For instance, don’t add, “I don’t know if it matters, but what do you think…” or “This in no big deal, really, but what do you think…” By couching the question to avoid conflict, you are granting the recipient permission to pull their punch. If they don’t have to commit, they won’t. Even if it’s a simple question like “want to go to lunch?”

Rule #5: Share your thoughts

This being a one-sided conversation, you must present your position on the topic. This gives the recipient something to react to, and helps them formulate a response. For example:

  • I think the requirements are complex and we would reach mutual understanding faster if we meet face to face. It will likely take two hours to get through them.
  • I will let the vendor know your decision, as it is entirely up to you
  • I have no meetings next Friday, and it won’t impact my work if I’m gone.

Exception to the Rule

If you have no opinion, say so. We are often just messengers in business, and merely connecting decision-makers. There is no shame in that, and it’s best for all parties to be clear about it. Claiming mastery of a domain where you don’t belong will confuse matters, at best. In the worst case, you’ll make an enemy at work.

Don’t be shy. If you have knowledge on the topic, say so, cite your sources, and be clear. No reason to pat yourself on the back. Similarly, if you’re confused or ignorant, say so. There’s no shame in that. Sharing vulnerability is a form of strength. The recipient should respect it. (The hell with them if they don’t.)

Rule #6: Explicitly suggest or ask for a decision (if one is needed)

If the topic requires a decision, then suggest one or ask for one, as appropriate. Be explicit about the need for a decision and specify deadlines. If you’re informing them of your decision, be clear about it so that they understand your position and reasoning.

Here are examples continuing from the previous ones:

  • Let me know by 3 p.m. today so that I can inform the project manager and arrange the schedule appropriately.
  • The vendor wants to know by noon tomorrow so they can make arrangements.
  • If you can let me know before lunch, I’d appreciate it because we’re trying to make plans for that weekend.

Don’t assume that the recipient will understand any deadlines or the basic need to decide. People are busy, distracted, and looking for things they don’t have to do. The email you sent to them is a candidate for something they can read and forget. Give them a reason to not decide and that’s exactly what they’ll do. And then you’ll only end up sending another email.

Rule #7: Thank them

Everybody is busy, or distracted, and the fact that they read your email should be rewarded. Thank them, and maybe even wish them a happy day. Here are a few examples I like:

  • Thanks
  • Thanks very much
  • Thanks for your time

Don’t overthink the thanking. I guess if telling people to make it a great day is your thing, you can add that. But I don’t. (I’ll say that stuff in person, in an actual conversation, but not in a business email.)

Do we have to follow all the rules all the time?

Of course, I break some of my own rules, or combine things when I’m confident I won’t muddle the message.

Not very email you send at work is a “business email.” You may be connecting with someone, or congratulating them, or fishing for opportunities, or scouting for danger. In fact, I’ll probably tell you how to write all of those, The Mickey Way, in the coming weeks.

Back to my boss

The reason my boss got away with not being able to email or correspond is because he had me do it, instead. After a while, I got tired of him asking, and I just stopped, feigning excuses or avoiding him. He went to other people in the office.

Eventually, everyone had been tapped to rewrite his crappy emails, memos and letters.

We made fun of him but he had the last laugh. When I tracked him down last year, he was a Vice President of a Chicago-based talent company. Well fuck it all, because that brings up…

Rule #8: If you can’t fucking write an email, get help

If you’re not sure about an email, ask for help. Find someone to discuss it with (in a conversation!). I do this with critical topics or in volatile situations. Thankfully, I can handle most email in my life and career, but when I’m nervous about one, I get a second opinion. Don’t be ashamed to ask for help.

Also, I don’t sweat hanging prepositions and split infinitives. If you don’t know what they are, that’s cool too. That is, your email doesn’t have to be grammatically perfect. But I will offer one more rule…

Rule #9: Sentences, paragraphs and DON’T USE ALL CAPS

Construct your email in sentences and paragraphs. If you have trouble with those, get help; but if you can talk, you’re probably using sentences already. Give yourself credit.

The trick with paragraphs is that they need to be built around a single idea with one or more sentences developing that idea: raising a point, making the counter-point, and wrapping up the idea so that the next paragraph can raise a different point. When in doubt, go with a shorter paragraph.

Often, the body of my business emails are four, one-sentence paragraphs, with a line in-between each to allow them to stand out; i.e., use white space. (You definitely don’t want to write it all in a single block of text without punctuation.)

And for the love of God, don’t use ALL CAPS.

Seriously, I could not believe that guy was a manager. And then he made God damn VP. Fuck.