I originally posted this on my blog a little over a year ago. If it's interesting to you, I post new content there roughly weekly.

From time to time in your life, you probably need to reach out to someone.  This might be someone you barely know or used to know.  It might be a complete stranger.

But if you're reaching out to them, it's probably because you want something or need something.  And if they don't know you very well, you're on thin ice from the get-go with this outreach.  This is easy to get wrong.

Today I'd like to address one of the biggest thematic ways that we all tend to get this wrong.  We mess this up by giving people homework assignments.

No Finger Pointing Here.  We All Do This, Me Included.

Before I go any further, let me confess to sending long emails.  I mean, to be fair, I go overboard with everything in text.  I tend to epitomize Blaine Pascal's sentiment, "I would have written a shorter letter, but I did not have the time."

In blog posts (or books), that can be a virtue when properly harnessed.  In emails, usually not.  How often do you receive a wall of text in an email and think, "oh, sweet, let's dig into this?"

And yet, that's what I tend to do, unless I fight myself.  So understand that nothing I'm saying here is intended as drive-by judgment of others.

Rather, it's an examination of how we can fight the impulse to send self-serving communications -- ones that inadvertently create homework for the recipient.

Empathize with Your Email Recipient

I own, as a partner or sole owner, 3 businesses.  One of those has dozens of people doing work for us, and another has me partnered with 2 folks in close proximity.  With these two business, I have something like 20 regular client companies with different people working for them, and I don't know how many prospects.

This puts the number of people I potentially need to be responsive to at over 100, whether responding directly or delegating.  If all of them needed a lot of things in a week, I would work well over 40 hours just responding to them.

On top of this, I also have public-facing concerns.  I have social media (though these increasingly broadcast only), a blog, blog comments, books, and more Slacks than I can keep track of.  I'm a panelist on a podcast.  Oh, and I also have friends and family.

I say none of this to ask for sympathy or to humble brag (complain brag).  I love the businesses, the friends, the family, and the venues for public outreach.  And I also really do make a concerted effort to respond to everyone that reaches out to me.  (Ask my wife, who often asks "why are you still up" when I'm interfacing in these venues.)

I say this because, as someone with products, influence, and jobs to offer, I'm representative of who you might request a favor.  And I'm going to frame the rest of this from my perspective, which is also likely the perspective of someone that you're emailing.

I Guiltily Punt on Homework Assignments

When you reach out to me, I want to help.  Seriously -- I really do.

But I'm also confronted with a scarcity of time to respond.  I've long since put lots of productivity/inbox hacks into place.  I triage my inbox at most once per day.  But even that's not enough, so have to make cold decisions.

I ignore spammy things, time wasters, and recruiters who claim to have looked at my LinkedIn profile and thought it corresponded to a good Software Engineer II candidate.  But the rest, I try to answer.

In spite of my best intentions, however, I sometimes declare bankruptcy.  Say someone writes or comments on an old blog posts and asks for help with some bit of example code I wrote 7 years ago.

That lands in my inbox, and at triage time, I look at it.  I want to help.

I read the email, glance at the post, and then realize this is not something I can respond to in 30 seconds.  It'll require some work.  So I add a Trello card to my backlog and vow to revisit it someday.

But, as Creedence Clearwater once said "someday never comes."  I never look at my Trello backlog and think, "yep, today's the day I have time to necromance some old code, so let me just spend an hour offering free tech support."  Instead, I look at that every day, thinking, "I'll totally do that later."

Until one day, I admit I'm never going to do it.  Then I archive the card, feel guilty for a few minutes, and never think of it again.

And that's how your homework assignment emails to people wind up on the dust heap.

Let's look at some homework assignment examples, what makes them homework assignments, and what to do instead.

1. Complete Time Wasters

Hello, My name is Backlink Spammer, I'm the head writer over at a site that you should report to Google for paid links. I’m writing to you because I’d love to contribute a guest post to your site. I’ve been brainstorming some topics that I think your readers would get a ton of value from:

• Going back into the Workforce with Confidence after Having a Baby
• Top 5 Tips for Moms Returning to Work

I’ll make sure the piece overflows with information that can’t be found anywhere else. In exchange I'll be sure to share your site to my social media following (3k+). I'm sure you'd get some nice publicity. Let me know what you think and keep up the awesome job with your site!

This one isn't rocket science.

Whether it's this or the recruiter spammer, the homework assignment here would be making any kind of response to this outreach.  It would require me to compose an email explaining how my website isn't about career moms and trying to figure out what common ground we have.  I ain't doing that.

Instead of sending this email, just don't send it.  Or, more specifically, don't get into the business of blasting out templated emails in the hope of results.  This is like trying to retire by playing slot machines.

2. Asking People to Figure out How They Can Help You

Hey Erik, Long time no talk -- what's it been, 6 years?  Anyway, I got laid off the other day, and have decided at long last to hang out my shingle.  I've got a lot of recent experience with digital marketing, and I've been super into AdWords lately, along with some advanced Facebook techniques.  Anyway, if you have any leads for me, I'd love to hear about it!

This is a much harder one, because it probably comes from a friend and someone that I want to help.  It's also a super common networking email.

But think about what this actually asks of me.  I don't know much of anything about Facebook ads or AdWords, let alone who I might know that might want to hire someone to do these things.  I read this email and... now I have no idea what to do.

So it gets a Trello card and probably a response like, "oh, awesome, I'll totally refer people to you."  And then it languishes there until I realize I'm not going to do it.

Instead of asking for open-ended help, make a specific request.  Can I introduce you to someone?  Should I be looking for specific characteristics of a company to identify an ideal client?  How, specifically, can I help you?

3.  Information Overload

I won't cite an example here, so as not to send the word count through the roof.  But you can probably imagine the type of email I mean.  It starts out with information about some person or company or whatever, and just kind of keeps going and going and going.

In this situation, unlike the last example, you find yourself inundated with specific, non-actionable, and confusing information instead of a vague, open-ended request.  This just becomes overwhelming.

I have to give myself this advice all the time, fighting my nature.  But keep your emails brief, figure out exactly what you want, and make your request/purpose crystal clear.

If you really need to include a lot of information, make your point clear and have it stand out.  Underline it, or say it briefly in the first paragraph and tell the reader they can read on if they want more information.

4. Literal Homework Assignments

Hi Erik, I was reading your blog -- great stuff!  Anyway, I binge read the following post and compiled the following list of errata...

I know people doing this mean well, but, ugh.  This makes a series of assumptions, packed into one sentence.

1. There's some actual business value to going in and correcting typos.
2. I have time to do such a thing.
3. The list of errata is actually accurate and wouldn't mean me editing in mistakes.

And probably some things that I'm not even considering.

And, however you slice it, this is the closest adult thing to a literal homework assignment.  "I've taken the liberty of creating a task list."  When someone writes something like this to me, I generally respond with a simple "thanks for reading!"

You may cringe at the thought of something like imperfect copy (probably if you're not a regular informal content producer) and assume that others would do the same.  But they generally won't -- especially busy people.

So rather than send an email like this, just don't send it.  Nobody is going to offer you a job because you pointed out a CSS problem on their site or identified a typo on their careers page.

5. Incorrect Assumptions about Asymmetrical Time

Hello Erik, I love what you're doing with MS Test Report Generator, though it looks like your edits to it have fallen off a lot in the last 8 years.  Let's schedule a call and discuss how we can rev this thing back up.  I have some definite ideas for how we could whip this into shape and maybe even make it something that we can sell.

Again, this is flattering, nice, and offers some sort of value proposition to me.  So, nothing against it.

But it also assumes that I was just hanging around, waiting for someone to come and enlist me in an unpaid part time job.

The fact that I haven't touched that code in apparently 5 years (though I would have thought longer) doesn't register.  This offers me nothing tangible except a sunk half hour on my calendar and some unvetted scheme to resurrect a Sourceforge project with the vague promise of money.

If you want to do something like this, showing instead of telling would go a long way.  You could do some work on the thing in question and offer to do a demo.

Or you could just let the person know that you intend to extend it/build on it, and ask for advice.  Pick a low touch way to engage, let the person know that you like the work, and that you'd be receptive to some kind of collaboration.

But make sure you specify that this is all entirely optional and would be a favor.

The Common Theme: A Specific Request, Quickly Executable

Hopefully you're catching on to a theme, so I'll wrap here by generalizing the advice.  When you make some kind of outreach or overture, make the favor you're asking as clear as possible.

But beyond making it clear, make it something that the person will quickly understand and can quickly act on.  Making an introduction, scheduling a call, forwarding a resume -- that kind of thing.

It could be that whoever you're emailing has plenty of time.  But I wouldn't make that assumption.

If you're reaching out to them for something important, like a job, a reference, a referral or some business, they're probably a leader, someone with a sizeable network, someone with a lot of prospects, or just generally busy.

So when you email them, imagine that you're going to get about 10 seconds of their full attention before it starts to wander.  And then imagine that you'll have a few minutes where they make a good faith effort to do the favor that you requested.

Asking for a favor is fair game and what makes the world go 'round.  But asking them to do homework in order to do you a favor is a recipe for wondering why your outreach isn't working.