When you have spent days, sometimes weeks and on the rare occasion – months, on a proposal or project how do you craft digital messaging that isn’t long, rambling, and pedantic? The longer and more complex the work, the harder it is to not write an off-putting wall of words that will never get read. It’s so frustrating because you tend to think, “all of these details are important, dammit. I want to show you the hard work, the sweat, the tears and thinking behind the success I’m about to communicate to you.” But reader for whom you are writing whether they be an employee, a prospect a customer or a banker likely already knows that you are capable, and this task was challenging.

In the digital age we all share the same values. Interesting, crisp, clear, and concise information. Time is everyone’s most valuable resource and biggest constraint. They think, “what the hell is this novella?! I have 3 minutes and there is no way that in that timeframe I will be successful in getting to what this is telling me, ergo I won’t read it.”

Done well, digital communication can be one of the best career builders and quick deal closer.


You must lead with a strong subject line. Don’t underestimate the implications of how we process our email. We don’t assess the overall content of the correspondence. No one gets that far. We judge the communication by the quality of the subject line. Think of it as the headline of a story or the cover of a book. If it’s strong the executive will read on. If its weak they will move onto something that based on a subject line looks more pressing.

What makes a good subject line? Two words: clear and actionable.

REQUEST: Please approve copy by Wednesday, September 21

REPLY: Input on Incentives for Q4

UPDATE: Executive Team Decision on Compensation

I don’t know how many people I’ve coached who plead with me on strategies to get face time with an executive or prospect to whom they’ve sent an email that hasn’t been responded to, but is urgent. Think of it in these terms…how annoying is it when someone calls you and leaves you a voicemail and then emails you five minutes later with the same information? Annoying right? Well booking a meeting to discuss an email is even more annoying to the executive without time.

To make matters worse more often than not when I ask, did you indicate in the email that this was time sensitive and/or urgent and/or response needed in the subject line…the answer is no. Help your time starved executive help you!


Now, despite succinctness being golden, let’s not forget that you are writing to a living and breathing human. Long and rambling salutations are slightly less annoying than an obtuse subject line – but in the same league.

Short and sweet will do but with a little personality and warmth.


Good morning, Sara, great job on the roll-out.

Hello, Mike. Another stellar sales quarter. Congrats to you and the team!


Next step – your first sentence is the summary that you are used to writing in a longer form presentation. It is the most important. If you consistently think about adopting the discipline of starting from the point of what you need to ultimately communicate, this will transform your communications the most. Before you channel your inner Ernest Hemmingway stop and really think about the one sentence that you need to convey.

If the entirety of the rest of the communication never gets read, your message would have been received in the very first line.

Here are some more examples:

  • Please find attached a first draft of the e-learning proposal you requested for your sales managers on executive execution and the most important finding is X.
  • This is your official reminder of our next Executive Team meeting via WebEx on Friday, October 4 at 11:30 AM PST where we’ll cover X, Y and Z – you need to be prepared to discuss.

The easiest way to ensure that you’ve got it all and haven’t overlooked key pieces…go back to grade 11 English: Who? What? Where? When?

Unlike longer form communications where I suggest drafting executive summaries last – write the first sentence, first. This is an email – not the proposal that might carry your business for the next decade. Don’t waste time drafting too any words only to try and cull them later. It’s a waste of time on both ends. Sit for a few minutes if need by and think rather than write. Inhale, exhale and think. It will save you time in the long run.

Okay – you have a subject line and a great summary sentence – this may have taken WAY LONGER than you think necessary (or are used to investing) but here is the good news – you are halfway done. All that is left is supporting statements.


A bulleted or numbered list, creates white space, quickly communicates key points and keeps the discussion on topic with the summary sentence. It’s not too daunting to dive in. Fear not graphics, charts or other ways to communicate without words if it makes the message more accessible.

Project updates with a dial showing overall status with a few sentences of interest are much better than 5 paragraphs of long form prose.


Last step is to close with specificity in action. You are writing to this senior person for a reason. Likely for their POV or opinion. Perhaps for their blessing. Sometimes to keep them current. Next to bad subject lines and rambling emails the other deadly sin is sending a communication to an executive with lots of great information but no ask or intention clearly laid out. These people are busy – they will read your email, not your mind. Unless you stipulate the thing that you want them to do, they’ll read the note and move onto the next one or run to their next meeting.

It’s incumbent on you to be clear and direct. Close with the next immediate step that makes sense based on what you’ve just written.

For example:

  • Please approve the project, based on this thinking by Tuesday, October 15 by replying with your agreement. If I don’t receive a reply I will book a meeting with stakeholders to ensure we have agreement before we proceed.
  • Please review and send me additional items you would like to see on the agenda by EOB Thursday, October 3. Thank you.

If you are struggling with any of these steps, you might need a meeting and not written communication. Its a good sanity check. It does take longer to write in this way. But it’s a heck of a lot faster than a back and forth and forth and back because you have missed being clear. Or the tarnish to your reputation when you inadvertently annoy an executive.

Put yourself in the shoes of your reader and write for them. Try and leave all of your ego around the work and complexities on the cutting room floor.

It is harder to be heard and effective in digital communication. You want to impress. Digital has made us all quick – stay ahead of the curve by being excellent.

Written by Anna Foat