Every week or so, I send out a free weekly newsletter where I provide heads-up of recent posts and critique (and sometimes rewrite) sales emails that readers send me. (I do this for free, so subscribe if you're interested).
Last night, while working on this week's newsletter, I realized that the sales email I was critique--one requesting a meeting with another person's boss--was an essential email skill for everyone, not just those working in sales.
Understandably, people are wicked touchy when it comes to their bosses. If you're working on a project with, or trading emails, with a contact, a request to get that person's boss involved sends up red flags.
First, the request implies that you believe that your contact lacks authority, which is a bit of an insult.
Second, it raises the specter that you might be trying an end-run and cutting your contact out of the decision-making process, thereby lessening his or her authority.
Third, and most important, such a request puts your contact in the position of recommending you to his or her boss and implicitly endorsing your agenda. Even if you don't accidentally blind-side your contact, you might screw up, which would reflect poorly on your contact.
A request to meet with another person's boss should be crafted so that it increases the benefit, to the contact, of setting up the meeting, while lessening the risk of doing so.
You accomplish this by putting yourself in the other person's metaphorical shoes and choosing your words and phrases to have that psychological effect.
To illustrate this, here's a slightly-edited, real-life "before and after" example. I'll give both versions in full and provide commentary on how they're different. Before I do that, though, read them both and see if you can sense the difference.
Version 1 (Original)
Wanted to reach out and recommend a meeting with you and your CEO so I can explain this to him.
Since this is a customized solution rather than a packaged application, I find that's an easier task for me to clarify any details than asking you to explain our entire solution in detail.
Let me know how to best accomplish that.
Version 2 (Rewritten)
Might I suggest a meeting between the three of us (me, you and your CEO) so that we can discuss the solution?
Since this is a customized solution rather than a packaged application, this would be an easier way to clarify any details rather than unfairly asking you to explain the solution to your CEO in detail.
Comparing The Two
On the surface, the two emails seem very similar. Both request a meeting with the CEO and make the point that the solution is complex and thus deserving of special attention.
However, the two versions "feel" different. The first version comes off as arrogant and faintly insulting, while the second seems more diplomatic. Here's why:
Version 1 With Comments
Wanted to reach out  and recommend  a meeting with you and your CEO so I can explain this  to him.
Since this is a customized solution rather than a packaged application, I find that's an easier task for me  to clarify any details than asking you to explain our entire solution in detail.
Let me know how to best accomplish that. 
1. The term "reach out" is biz-blab and thus best avoided but the real problem with this opening to this email is that it immediately establishes that the email is about something that you want, rather than something that the contact might want.
2. The word "recommend" is a huge red flag. Are you telling your contact how to handle his or her boss? Are you intending to make a recommendation over your contact's head? So this word comes off either presumptuous or dangerous.
3. The phrase "explain this" implies that the CEO is ignorant and needs things explained to him. People in general (and bosses, in particular) don't like having things explained to them. Your contact know this (we'll use this fact to your advantage in the rewrite.)
4. The clause "I find that's an easier task for me" is self-centered. The contact probably doesn't care what's easier for you, especially when it comes dealing with the contact's boss.
5. The sentence "Let me know how to best accomplish that" is a direct order. You've already implied that your contact lacks authority and now you're ordering your contact about? At this point, you chances of landing the meeting are approximately zero.
6. Thanking somebody in advance of that person actually agreeing to something is exceedingly rude. It implies that you're so certain they'll comply with your that you're already thanking them. How presumptuous!
Version 2 With Comments
Might I suggest  a meeting between the three of us (me, you and your CEO) so that we can discuss  the solution?
Since this is a customized solution rather than a packaged application, this would be an easier way  to clarify any details rather than unfairly asking you  to explain  the solution to your CEO in detail.
Your thoughts? 
1. The phrase "might I suggest" sets a deferential tone. You're not recommending but merely making a suggestion, which is much less threatening.
2. The word "discuss" doesn't carry the negative burden of the word "explain" and implies an equality of knowledge and perception.
3. The phrase "an easier way" rather than "easier for me" makes it clear that you have everybody's interest at heart, not just your own convenience.
4. My use of the word "unfairly" here is a touch of brilliance, if I do say so myself. That word positions the email as an attempt to help the contact avoid a difficult task.
5. Introducing the toxic word "explain" at this point positions what you don't want to have happen (no meeting) as something that force the contact to offend the CEO by "explaining" it, perhaps badly.
6. Closing with "your thoughts?" shows respect for, and deference to, the contact's opinion. This further lessens any sense that you're threatening the contact's authority.
The Art of Emailing
Since I've been helping people with their messaging, I've run across numerous similar situations that require the same sort of email finesse. Just out of curiosity, does anyone think a book or e-book of sample emails like the above would be useful?
If so, email me. I'd love to hear from you.