How to Screw Up An Email Negotiation


send emailIn 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.



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.

the finance ninja

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


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. 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.


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.


One little service that might make things more “linear” if you have to have these kind of conversations over email is 9cays ( 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.


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!


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.

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