How to Ask a Busy Executive for Anything

[This is an excerpt from Debugging Teams, written by Ben Collins-Sussman and myself. If you like it, we suggest buying a copy for yourself. And your manager. And your team.]

Work in any big company long enough and you’ll find yourself in a position where you need to email an executive (or any busy person you don’t know) to ask them for something. Perhaps you need something for your product or team, or you are looking to right a wrong. Whatever the case, this is likely the first time you’ve ever communicated with this person. In this situation, almost everyone makes the same rookie mistake: they ramble, rant, and rave.

Fitz (while working at Apple) bought his mom a lemon of an iMac more than 14 years ago, and on the advice of a coworker sent a “short” email to Steve Jobs. Fitz had initially penned a mostly incoherent rant to Steve, which would have gotten him absolutely nothing — well, other than a pink slip. His coworker advised that Fitz keep it short and to the point, and to close with a call to action. This email served as a rough prototype of how to effectively ask an executive for help.

Date: Thu, 1 Feb 2001To: sjobs@apple.comSubject: Terrible customer experience with our hardware — what can I do?I would deeply appreciate if you could advise me on what I can do to
address this problem. This is embarrassing — both for Apple and for
myself.
I purchased an iMac for my mother last Mother’s Day — she is the
Vice-Principal of a Montessori school in New Orleans and uses an old
Macintosh at school. She was very excited to get the iMac, and has
even gotten funds for her school to buy iMacs for their lab.
However, the strawberry iMac I bought for her has turned out to be a
total lemon.
- In July, it went to sleep and never woke up. She brought it to an
Authorized Apple Dealer and they diagnosed the problem as a failed
logic board and replaced it.
- She brought it home, plugged it in, it started to boot, then she
got a sad mac and the tones of death. She brought it back to the
dealer. They diagnosed the problem as a faulty analog board and
replaced it.
- In September, I finally convinced her to use the sleep function
again (in lieu of shutdown/boot). The iMac wouldn’t wake
up. Completely unplugging the computer and plugging it back in
eventually got it to boot again. We have disabled sleep altogether
at this point.
- In December, the monitor started flickering colors from yellow to
green to blue. She brought it back to the dealer yesterday, and
that’s where it is now.
So that’s where I am today. My mother thinks I’ve pulled some sort of sick prank on her, is telling everyone she knows that her iMac is
junk, and no one I know that works at Apple knows what to do about it.
Is there anything that I can do to get her a working iMac (short of
purchasing another one)?
Respectfully,-Fitz

Less than 20 hours later Fitz received a call from someone who worked for Steve, and two weeks later his mom had a new (non-lemon-flavored) iMac.

When given a chance to help right a wrong, more often than not people in positions of power would love to do the right thing — even busy executives (many of them enjoy righting a wrong, and absolutely all of them understand the value of gaining a little extra political capital). Unfortunately, the email inbox of these people looks like a never-ending distributed-denial-of-service attack. And if they encounter an email from someone they’ve never met before that is 3,000 words of solid text with no paragraph breaks, the odds are good that they’re going to read 15 words in, press the Delete key, and then move on to the next email.

If, however, they can fix something by reading an email in 10 seconds and waving a magic wand (i.e., mailing one of their minions to Make It Happen), they’ll likely do it. They spend a few seconds delegating and they get a big pile of political capital from you in return.

After years of trial and error, we’ve found that shorter emails are even more likely to get a response.

We call this the “Three Bullets and a Call to Action” technique, and it will drastically increase your chances of getting action — or at the very least, a response — from just about anyone you email out of the blue asking for something, not just an executive.

(Warning: if you’re peanut-butter-hula-hoops crazy, this isn’t going to help get you an interview with the President of GE, a purchase order from Chevy for your laser-powered windshield wiper invention, or lunch with the director of sales for Whole Foods. This technique only applies to realistic requests)

If you ramble or put four completely different things in the email, you can be certain that they’ll pick only one thing to respond to, and it will be the item that you care least about.

A good Three Bullets and a Call to Action email contains (at most) three bullet points detailing the issue at hand, and one — and only one — call to action. That’s it, nothing more — you need to write an email that can be easily forwarded along. If you ramble or put four completely different things in the email, you can be certain that they’ll pick only one thing to respond to, and it will be the item that you care least about. Or worse, the mental overhead is high enough that your mail will get dropped entirely.

The bullet points should be short sentences (each one should fit onto a single line without wrapping), and the call to action should be as short as possible. If you want a reply from anyone, make it easier for the person to reply inline, preferably with a one (or two) word answer. Don’t ask half a dozen questions in one paragraph: limit yourself to a single question per paragraph, or ideally, a single question per email. Lastly, your email should be loaded with Humility, Respect, and Trust (HRT): polite, respectful, and devoid of grammar mistakes and spelling errors. If you positively cannot help yourself and simply must include more background or information, put it at the very end of your email (even after your signature), and label it clearly as “More details” or “Background.”

Illustration by Amber Lewis

In hindsight, we consider Fitz’s prototype email to be a bit too wordy — if we were writing it today, it would probably look more like this:

Date: Thu, 1 Feb 2001To: sjobs@apple.comSubject: Bad customer experience — can you help?- I purchased an iMac for my mother, a school administrator. She was
very excited to get the iMac and has even gotten funds for her
school to buy more iMacs for their lab.
- In July, Apple replaced a faulty logic board, and a month later,
the analog board.
- In September it stopped sleeping correctly, and in December the
monitor started to fail. It’s currently at the dealer.
My mother is telling everyone she knows that her iMac is junk, and no one I know that works at Apple knows what to do about it.Is there anything that I can do to get her a working iMac?Respectfully,-Fitz

This rewritten email eliminates a lot of the editorial color, but is now readable by a busy executive in 10 seconds.

In the course of our careers, we’ve used all of these techniques over and over again to get things done. The best part of it is that everyone who we’ve shared this story with now sends us emails in this format — everyone wins!

[This is an excerpt from Debugging Teams, written by Ben Collins-Sussman and myself.]

Founder & CTO: Tock, Inc. http://www.tock.com/ , Xoogler, Ex-Apple, Author, Co-founder of ORD Camp. Feminist. ✶✶✶✶ Chicagophile ✶✶✶✶ ‘No Formal Authority’ — HBR