How to Screw Up An Email Negotiation
December 3rd, 2006 (8:51pm) Anne Zelenka 27 Comments
In the new world of web work, you might find yourself negotiating by email over a job or project. Most of us know how to screw up phone or face-to-face discussions. Scotching plans by email requires a completely new approach.
Remember that email is asynchronous, impersonal, and only seemingly private. Use these characteristics to best advantage and you’ll never have to deal with a pesky email-negotiated business deal again.
Here are five unbeatable ways to screw up.
1. Make your emails as long as possible. This gives you the best chance of saying something stupid or offensive. It also increases the probability that your email will not be read in its entirety, thus setting the stage for later relationship-damaging and negotiation-destroying misunderstandings.
2. Don’t respond in a timely manner to emails you receive. Let the other person stew about what you’re planning or thinking. They might get so frustrated that they find someone else to work with. At the very least, they will doubt your interest in the job or project under consideration.
3. Learn to stalk, if warranted. If you find yourself on the other end of Principle #2 above and you’ve gone days without hearing anything, take a page from the Internet Stalker’s Handbook. Send email after email to your love… er… potential business partner. Tell them you can’t live without them. Make sure they know exactly how you feel, down to how your ingrown toenail reminds you of the pain you’ll suffer if you don’t get to work with them. Don’t, under any circumstances, send a quick and neutral follow-up note to check in. You need to escalate and suffocate not relate and motivate.
4. Never resort to synchronous means of discussion like instant messaging or god forbid, the telephone. (Except when deploying Principle #3, of course.) Sending an IM or picking up the phone is a bad idea. You might actually start to understand the other person’s point of view and they might understand yours. Worse, you could find yourself in a back-and-forth that leads to connection and agreement. Email’s strength is how it leaves long pauses between complete misunderstandings, allowing said misunderstandings to fester and grow until they kill the discussions outright.
5. If you suspect you have been insulted, you probably have–respond immediately in kind. Try the Shakespearean Insult Kit if you can’t come up with any good ones yourself. Calling someone a droning crookpated footlicker is sure to squash any chance at agreement. You probably won’t ever have to hear from that fobbing clay-brained cankerblossom again.
For extra credit and to ensure you won’t ever confront negotiation by email again, publish the entire thread on the web for everyone to read.
How do you find email as a tool for negotiating? Share your dos and don’ts here.

27 Comments Post your own comment
LG says: December 4th, 2006 3:21am
I’ve only ever negotiated one project by email: A Rent-a-coder job for a reasonably complex website. It wasn’t a disaster, but despite us both being fairly experienced contract negotiators, we’d both built in a whole lot of assumptions that we hadn’t necessarily communicated to the other.
Fortunately with plenty of goodwill on both sides we got to a satisfactory conclusion (And the coder agreed to do a number of things that we had assumed he would, and that he had assumed he wouldn’t for free), so it wasn’t a disaster by any means, but in future I’ll be making sure that the pre-contractual negotiations are more detailed and incorporated better in to the text of the agreement next time around.
susangpyp says: December 4th, 2006 7:57am
Excellent advice. It is very difficult to negotiate in email. Subtle remarks and nuances are lost.
Another tip is to make sure you use passive voice, misspell everything and have the worst possible grammar.
Talk down to your adversary and understand that negotiating is not about coming to a reasonable solution but about getting your own way no matter what.
Employ scorched earth techniques.
Go get em champ!
GigaOM » How to screw up an email negotiation says: December 4th, 2006 8:26am
[...] A tongue-in-cheek guide to screwing up negotations over email. [...]
borremap says: December 4th, 2006 9:32am
One little service that might make things more “linear” if you have to have these kind of conversations over email is 9cays (http://9cays.com). It brings all your emails in a nice threaded discussion format and creates a webpage for the whole email “conversation”. I used it a couple of times, gives you a good one page overview of the whole email discussion and is easy to keep for later referencing.
petegraham says: December 4th, 2006 9:52am
A great technique that I experienced in my previous job was when you asks a question such as “what time should we meet?” and the other person replies “yes” or some similarly monosyllabic answer that doesn’t correspond to the question asked, guaranteed to piss-off almost anyone.
E-mail Gone Wild « Pour Out says: December 4th, 2006 6:57pm
[...] Great post over at Web Worker Daily on how not to use e-mail. Don’t we all fall into these traps from time to time? I know I do. WWD, consider yourself del.icio.us(ed). [...]
extrapolater says: December 4th, 2006 7:16pm
Funny stuff. I like it. Especially escalate and suffocate.
How to screw up via email « Email Insights says: December 4th, 2006 9:24pm
[...] I read an absolutely hilarious article on “How to Screw Up An Email Negotiation” over at Web Worker Daily. [...]
enjoyyourbath says: December 4th, 2006 9:31pm
DONT, a true story:
So Firefox does this nifty thing where it saves other people’s passwords onto your computer and then you can view them from the Tools/Options menu. Some people who dont know this will accidentally save their password on your computer and not think much of it. Until you decide to stalk them and read their email. Then what happens is that you get careless. Then..you send an email from their account (b/c, after all, gmail windows look similar) to someone else, signing your name.
There just…aren’t words for that.
enjoyyourbath says: December 4th, 2006 9:32pm
“long pauses between complete misunderstandings”
yes, also, that’s VERY true!
Leo Archer says: December 5th, 2006 1:27pm
Ways to mess up an email negotiation
On the off chance you find yourself negotiating over email, here are a few tips on how to really mess up the negotiation: Make your emails as long as possible. Don’t respond in a timely manner to emails you receive.
How To Screw Up an Email Negotiation « Organizations and Markets says: December 5th, 2006 3:49pm
[...] From WebWorkerDaily, tips on how to screw up an email negotiation. Highly recommended. Generalizes easily to other kinds of email exchanges. [...]
the finance ninja says: December 5th, 2006 6:33pm
ha ha ha. This post is really funny. I always get into negotiatingly argumental emails. The question comes up, “Can I call you?” and you are like “No, I have to go”. Smart post. -fn
Distributed Work Advice « AOM.OCIS Student Networking Site says: December 8th, 2006 2:57am
[...] This humorous post is a gold mine of practical advice: How to Screw Up an Email Negogiation. I’ve been guilty of one or two of those items before, how about you? [...]
TameBay says: December 8th, 2006 10:40am
How not to answer an ASQ
As we draw ever nearer to Christmas and sellers’ time is at a premium, nothing is more of a pain than eBay’s “Ask Seller a Question” (ASQ) feature. Ensure that your buyers don’t make too much use of it with our handy hints:
Aaron Johnson » Blog Archive » Links: 1-15-2007 says: January 16th, 2007 2:41am
[...] Web Worker Daily » Blog Archive How to Screw Up An Email Negotiation « Quote: “Email?s strength is how it leaves long pauses between complete misunderstandings, allowing said misunderstandings to fester and grow until they kill the discussions outright.” (categories: emailsucks useIM email communication workplace rules business ) [...]
TameBay » Blog Archive » How not to answer an ASQ says: February 1st, 2007 2:00pm
[...] Inspired by Web Worker Daily’s How to Screw Up an Email Negotiation. [...]
asdir says: February 8th, 2007 7:16am
Hi
Web Worker Daily » Blog Archive How to Hold Impromptu Conversations on Virtual Teams « says: March 22nd, 2007 12:01pm
[...] isn’t a great replacement for these casual encounters. It may be too slow and can cause misunderstandings. Instant messaging is better, but can be an annoying and limited way of [...]
Beautyfil Mind » Blog Archive » Weekend Reader says: April 16th, 2007 2:48am
[...] appropriate for condolences or apologies. See Web Worker Daily’s take on email etiquette in How to Screw Up an Email Negotiation by Email. [The New [...]
Web Worker Daily » Blog Archive Tip of the Week: Don't Enter To and CC on Email Until Ready to Send « says: April 23rd, 2007 11:52am
[...] If you follow this advice, you might also avoid sending rants and flames that are better left in the Drafts folder. That’s a good thing — unless you’re trying to screw up business dealings by email. [...]
How to negotiate more effectively with anyone » Brazen Careerist by Penelope Trunk says: May 17th, 2007 9:27am
[...] of our lives to practice negotiations constantly – even, as Web Worker Daily points out,  in email. You can do it with a spouse, with a boss, with your neighbor who doesn’t clean the yard. The [...]
negotiation says: July 31st, 2007 7:04am
Had fun while reading…hope nobody will take this seriously :)
How to Screw Up An Email Negotiation at Conceptualist.com, By Sahar Sarid says: December 17th, 2007 10:03am
[...] Web Worker Daily: In the new world of web work, you might find yourself negotiating by email over a job or project. [...]
How to Screw Up An Email Negotiation - Domainly says: December 17th, 2007 10:20am
[...] Web Worker Daily: In the new world of web work, you might find yourself negotiating by email over a job or project. [...]
如何有效地与人谈判? - One Leo says: April 19th, 2008 2:58am
[...] in each of our lives to practice negotiations constantly – even, as Web Worker Daily points out, in email. You can do it with a spouse, with a boss, with your neighbor who doesn’t clean the yard. The [...]
Simon says: April 25th, 2008 8:47pm
There is probably room for e-mail in negotiations, such as fact finding, confirming understandings, etc. Just don’t use e-mail for the entire negotiation. Negotiations involve building trust, rapport, relationships, common ground, finding solutions, and all that gets quite inconvenient to do when the communication is not in real-time.