Emailing “Up the ladder” can be daunting.  Each rung adds risk.  What is the right length?  How detailed should you be?  How do you get approval for your project, purchase, or proposal?  How can you be sure they will even read it?  What if they don’t respond?

A few simple strategies will help you communicate effectively with supervisors and CEO’s alike.  Check out these email recipes, and season to taste.

☑ Make an altitude adjustment.

The higher up the ladder you go, the more people and projects there are competing for your attention.  Keep that in mind when communicating up.  It’s a lot like flying: the higher you go, the larger something has to be to get your attention.  Until you know individual preferences, stick with the main points for CEO’s and work your way down to detailed work instructions for the front line.

☑ Include an informative subject line.

Make your subject line specific, and NEVER leave it blank. 

  • “Meeting notes” is not as helpful as “Agenda:15MAR Meeting w/Bob Smyth.”  
  • “Budget reminder” is not as informative as “Budget drafts due Oct 1.”  
  • “Project purchase” will not capture attention like “Upcoming $5k purchase.”

Keep the subject line brief.  My phone shows maybe 30 to 40 characters, then “…”.  Keep the subject as short as possible while still being clear.

☑ Begin the message with a summary.

Especially with long emails, dessert comes first.  Email is a poor medium to make a case or build suspense.  Start with a summary of the main points.  A good summary provides enough information to let the reader take action or decide to read more.  When in doubt, go with the 5 W’s + How (or how much).

Like the subject line, keep the summary brief.  Your summary needs to fit on one screen of a typical smartphone.  When in doubt, use this rule:  You get three sentences to make your point, and the last two don’t count.

☑ Use passive actions to keep things moving.

If you know what action needs to happen and you are emailing just to get approval, you may be setting yourself up for failure. Once you hit ‘send,’ you might languish in limbo waiting for a reply that may never come.

Passive actions work like opt-out email subscriptions: the action continues unless the recipient says “no.”  Specifically state in the email (the subject line if possible) when an action will happen if the recipient does not object, veto, or redirect.

Example: “Boss – the battery backup died. I need to replace it ASAP, so the database server doesn’t go down if we lose power. The cost is $2,000.  I will place the order Thursday if you don’t veto by then. Thanks.”

The Boss is a busy person. If they read the above email and have no objections, they can just delete it and move on, knowing that you already plan to do what is necessary.

Two important notes: (1) Do not try to use this while the boss is on vacation, and (2) give as much advance notice as you can.  If you need to act immediately and you think the boss must know in advance, CALL.

☑ Where to add the details.

Despite (or because of) your effective, succinct, attention-getting subject line, summary, and passive actions the recipient may want / need more details.  End your summary with “Details below,” skip a line or two for blank space, and add what you think is necessary.  If your explanation will go beyond a couple of paragraphs, consider attaching the details as a report in PDF or Word format.

☑ Extra point: If you forward, summarize.

Nothing is less likely to get a response than a long, forwarded email with nothing but “See below” or “What do you think?” or even just “?”  You may get a response, but you will wish you hadn’t.

The same general guidelines for ‘Emailing Up’ also apply to forwarding an email. Begin forwarded messages with a brief summary of the content, and the specific reason you have forwarded it.  Use passive actions if warranted, with the forwarded message becoming the “details” section.

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