How To Start Writing That Important Business Message

I was taught how to write a formal letter in elementary school. In retrospect, that seems about as useful in 2017 as learning the optimal way to craft a telegram.

Thankfully, writing has never been something that I particularly struggled to do well — but now that we're all writing more than ever, a whole new swath of the population is dealing with a relatively new (to them) phenomenon: writer's block.

And one thing that has never been easy to me, whether it's written or not, is reaching out to a stranger to ask for a favor. But I've had to get good at it, or at least comfortable with it — this is precisely what a journalist does every time he or she asks a new source to spend some time sharing information about a story.

There's nothing like having an important email to send and not knowing how to begin. (And despite my snark, I suppose occasionally something must be sent via snail mail, too.)

Have something important you need to say in a piece of business writing and not sure where to start? Here's how you can beat the block of writers everywhere.

The salutation

Don't feel bad if you get stuck on the first word. We've all been there.

In letter-writing days, there were a number of appropriate salutations to use. Here are just a few variations on "dear," the one that remains most popular today*:

  • Dear _______,
  • Dearest _______,
  • Endeared _______,
  • My dear _______,
  • My dearest _______,

This is probably not where you want to go in this day and age, where beginning an email with "my dearest" is best done as part of an inside joke with a close friend, if at all.

There is absolutely nothing wrong with "Dear," so use it as needed — even if it feels a bit unnecessarily formal to you (which it may to those who are unused to writing letters), the person on the receiving end likely sees "Dear My Name" so often during the day that it doesn't even register.

I suggest using a "Dear So-And-So" salutation for people you don't know well.

For the love of Pete, don't send an email to "Dear Marketing Manager" in this day and age. You should definitely do a bit of mild reconnaissance on your intended recipient before deployment (a little bit more on that below) and do your best to identify the actual human on the receiving end of your missive. Place a phone call if Google won't help you.

Once you've established a relationship, most recipients seem amenable to swapping out a more formal "Dear So-And-So" for a more endearing "Hi So-And-So." But when in doubt, always err on the side of formality.

The greeting/connection

You got your first two (or maybe three!) words written! Win.

Now you need an "icebreaker" — a sentence or two that will "hook" your reader and entice him or her to keep going. This is where a little sleuthing can become absolutely invaluable.

First: Have you met the recipient face-to-face — ever? If so, this is a perfect greeting to leverage. Refresh their memory as to who you are and how they know you (and it's really helpful if you can offer them some reminders about what they said or did, which will help them place you more quickly if they might be in doubt).

And then say something nice. It can be as simple as "hope you are doing well" and as targeted as a pronouncement of blessings on the eve of their daughter's wedding.

Here are a few examples:

  • "Dear So-And-So, This is Such-And-Such; we met at Lorem Ipsum's networking event in March. (Hope you enjoyed your vacation to Cancun!)"
  • "Dear So-And-So, This is Such-And-Such; we met in line for coffee at the goatherding convention. (How's that little pygmy goat of yours — did that ear issue clear up for her?)"

(When you exchange a business card with someone new, if you know you want to follow up, jot down how you met this person and a few notes about your conversation that you can resurface later. Showing people that you are paying attention to what they say can be a better referral than, well, a referral.)

But what if you've never met this person before? Here is where social media becomes your friend.

Find them anywhere they might have a social media presence — the usual suspects, like Facebook and Twitter, definitely apply, but don't neglect LinkedIn, which can provide some invaluable job history information. (And for some reason, it feels much less creepy to link in with someone on LinkedIn than it does to friend someone on Facebook — right?)

Then look for locations you've had in common, especially if you've lived in the same city as your target recipient. Schools and workplaces can be good indicators of where someone has been geographically in his or her life. If you've visited somewhere that your recipient has lived, that could be a good connection — although if it's a large city (like New York or San Francisco) and you aren't sure what part of the city is relevant, then consider skipping ahead to the compliment angle.

If you're already connected on social media, then it's not weird for you to mention something that the person posted about on Facebook (or wherever), so don't hesitate to use that as a tool, too.

When you send your email, introduce yourself first and then offer your connection.

  • "Dear So-And-So, This is Such-And-Such, the ABC at 123. We both attended the University of Missouri (and I think I might have used your master's thesis in my capstone paper!)."
  • "Dear So-And-So, This is Such-And-Such, the ABC at 123. I follow you on Twitter and saw your tweet about the bottomless pho deal at Pho 96 on Federal in Denver; I had the chance to eat there once and it was amazing."

One thing you should not do is tell your recipient that you discovered he went to such-and-such a school when you looked him up on LinkedIn. That's mildly creepy at best.

If your recipient does ask, then by all means disclose where you found the information — definitely don't hide it, which is also creepy — but I've personally been a little bit freaked out in the past when someone mentioned looking me up online before attempting to connect. "Hi Amber, I'm so-and-so, great to meet you! So I see on LinkedIn that you went to this school and worked there and there and there and now here." Whoa now!

It still worked; I responded — but here I am, remembering how I felt weird about it, so maybe don't precede your we-have-this-in-common statement with "I looked you up on the internet and here's a list of things I discovered..."

OK — but let's say you don't have anything at all in common with the person you are emailing. You have never met the recipient and you don't share any locations or possibly any (discoverable) hobbies in general. Now what?

Try to dig a little deeper and find examples of this person's online work. This could be an article or blog post that he or she has written, an event or promotion or even a public social media post or photo.

In an ideal world, the person you're sending the important business message to, even if a complete stranger, has enough of a public profile for you to be able to find something that he or she created and that you can compliment — and mean it; that's the key. Introduce yourself, then deliver that (sincere) compliment.

If there is truly absolutely nothing that you can think of to say in praise of this person — why are you sending him a message? Because he's accessible? Smarter people than I have suggested you rethink that strategy.

Don't make the compliment a generic "this was great" — try to find something about the work that truly resonates with you and that you can praise from the heart.

Some examples for this greeting could be:

  • "Dear So-And-So, This is Such-And-Such, the ABC at 123. First — I thought the survey report that your team published last week was the most insightful research on remote employee engagement that I've seen; I've already implemented some of your experts' suggestions and think they have made a real difference in my own company."
  • "Dear So-And-So, This is Such-And-Such, the ABC at 123. Can I start by saying that I think the philanthropic work you instigated at your organization is really making a difference to the community? I am an especially big fan of the food bank you funded and want to thank you for caring enough to do it."

Don't go overboard with compliments — that is obviously insincere — but a well-thought-out "hey, good job with that thing, there are people who see you doing it and appreciate it" before you jump into the meat of your message can be the difference between a reply and ... not.

The ask

Now you've got your target appropriately set up to ask them ... what? Do you know what you're asking?

I'll dig into this more at some point in the future, but understand this: You've just wasted your time crafting a greeting that's going to hook and engage your recipient — and you don't even know why you're doing it. Back up!

Scrap it all and start here if you don't have it nailed yet. Knowing exactly what you want to ask will help you get a long way toward identifying the appropriate person for your message, timing it correctly and deploying for success.

Is all this always necessary?

Absolutely not; these are just ideas to get you started in the event that you can't think of what words to put on the screen (or page) when you have a message to deliver.

My assumption is that (like me) you get most nervous when you're sending a message to a stranger or when the stakes are highest. Once you've moved past the "stranger" part of the relationship, it's much more acceptable to shorten the process — but I'd argue it helps keep your email relationships strong if you can run through a truncated version of this format every time you have an "ask" to deliver.

Examples:

  • Hi Firstname, Congrats on the new product launch last week; I saw the photos and everyone looked like they were having a blast! Hey, about that project we discussed ...
  • Hey Firstname, Hope all is well and you're enjoying the new place! How'd the move go? I wanted to see whether you were still ...

And if you're like many writers (I suspect you are), the writer's block will ease once you've figured out how to start.

* I will be personally indebted to any reader who brings me a better "stranger-suitable" salutation than "dear," however, because I looked everywhere and couldn't find one that made me happy.