credit : http://news.discovery.com/human/life/message-in-a-bottle-found-76-years-later-130121.htm

The Art of Managing Up

How to write better emails to your boss

I've managed software engineering and product teams for a long time, and I have seen all sorts of email styles from my peers and team members. If you have a manager, it’s a safe bet that you've never asked her what the best way to communicate via email is. I've never been asked, but wished that I had.

Now is the perfect time to write this article, since I'm not currently managing anyone (I started my own consulting company and no employees yet). I can always point any future employee here. Please read this article, because this is the honest truth about how I, and probably most managers, prefer to get emails from team members. This article will help you avoid some awkward conversations. There’s no easy way to tell someone that he doesn't know how to properly write an email, and that he doesn't need to cc me for every task completed throughout the day.

Here is my advice

  1. Do ask your manager how she would like to get email communication from you. It shows consideration and respect. You get a opt-in effect and early buy-in. Of course, your manager expects to get email from you but it’s better if you ask how often and in what situation email is appropriate or unnecessary. It will get you points. It would be a delightful conversation because your manager probably has never been asked, and you two will have a good time talking about it.
  2. Do not cc your manager on everything that you do in the attempt to keep her informed. Your manager is just as busy as you are and she hired and trusts you to do your job. You already have specific meetings, status reports, or wikis to keep your manager informed. You don't need to cc again as FYI. You do not need to cc your manager when communicating inside the team or the project. You are expected to work efficiently and communicate effectively.
  3. Do cc your manager when communicating outside your team or your manager’s peers. Your manager needs to stay on top of external communications because there are no status reports from outside groups, and real-time email discussions help keep the pulse on the situation, bcc might be appropriate in this situation.
  4. Do not forward email with just FYI. If you are going to take the time to forward something, then take the time to explain your perspective on the need to forward the email, even it’s totally obvious to you. Believe me, your manager lives by email and gets 10x the email volume compared to you, so take the time take to explain why she should read just one more FYI email from you.
  5. Do not forward a long email with a long conversation thread and expect your manager to digest it all and make the appropriate decision or action because you forward it. It’s your job to provide the context and content to help your manager make the best informed decision possible. Do keep the original email thread at the bottom as reference but always provide a summary of the situation as you see it in a balanced and professional way, and most importantly, make it clear in the last sentence the expected action or decision.
  6. Do avoid long emails or emails with multiple important to-dos. If your email is more than one page long, then pick up the phone or walk into the room and talk. Break up email with multiple requests or multiple subjects into separate emails. It’s easier for your manager to manage emails and tasks this way. One task per email allows her to delete an email as soon as the task is completed. This way multiple requests can be handle independently, based on priority, and will not get lost.
  7. Do use and change the subject line as appropriate. The subject line and the closing lines are absolutely the most important part of the email, use them wisely. Email without subject line or bad subject line is an indicator of a disorganized mind.
  8. Do read and follow email etiquette. There are many blogs about email etiquette. Avoid ALL-CAPS, use punctuation, avoid texting shorthand , use smiley faces sparingly, etc.
  9. Context before Content. This is branding 101. Don't assume that your manager is up-to-date on everything that you do or knows the correct decision. Your manager hired you because you are the expert, her go to person for the challenge. Every email that you send to her is an opportunity to demonstrate your knowledge. Show her how you can analyze a complicated issue, and synthesize it to a few critical decision points, and have the strength and knowledge to take a position and make a recommendation. Take the time to craft a high quality email that provides the context of the situation and the content of the decision. Even if the manager disagrees with you, you have shown your experience and judgment. Be proactive with your opinion and recommendation, but be respectful and let the manager have the final say.
  10. Finally, this is the most advanced technique, write the email from your boss’s perspective, and write the email such that she can copy and paste then send it off to her peers, her manager, or the rest of the team. If you want that promotion then you need to show how you can think and talk like your manager. Your manager has to juggle more projects, situations, and people than you know. She spends ungodly amounts of time reviewing reports, spreadsheets, and writing emails to drive a project to conclusion. Anything you can do to help would be highly recognized and appreciated. So write emails like your manager and you are on your way to earning that promotion.

In summary, as a manager, I want to see fewer, higher quality and more thoughtful emails that respects my time and demonstrate your value. The advice is not just for email to your manager, it’s good advice for all email communicating with everyone in and outside team. Practice them and you'll go far.

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