Root Deeper TGIF Tip: Avoiding Sender’s Remorse on Email II, “Sleep On It”

In case you missed it, last week, here: TGIF 12/5/14 30-Second Rule is how to spend 30 seconds to give you a “second chance” to reconsider every email you send.  This week’s tip focuses on both giving yourself a longer time to “think it over” but also looks at choosing email timing to best integrate with your workflow overall.

Emailer’s Remorse?

Many of us have experience the great aggravation of sending an email and regretting it later.

Maybe we said something when we were annoyed. Maybe we realized later we misunderstood a point someone was trying to make and feel silly. Or maybe we sent the email to the wrong recipient!  There are literally millions of horror stories about emails we wish we could “take back”.

Particularly for people who can be “hot-headed” and send emails out of annoyance, it is important to build in space for reflection. In our hectic and harried days many of us can get cranky occasionally and “snap at” colleagues. This is not good, but it’s much worse if it’s an email that will forever be floating in cyberspace, and may someday come back to haunt you.

To keep from hurting your colleagues feelings, and to help you maintain your decorum at all times, you may be helped by Active Inbox.

This is the next tool I’d like to share to help you prevent Emailer’s Remorse!

Active Inbox: Is a “byproduct” actually their best selling point?

My friend George Bounacos from Silver Beacon Marketing clued me in to Active Inbox, so I want to share the wisdom.

Active Inbox is an email task-management program. It’s pretty cool, and allows you to flag emails for follow-up, indicate you’re waiting on a reply, and do other groovy things.

But for someone who wants to stop “shooting off” emails immediately but doesn’t want to have to “think about it” (EG remember to send something later) it has a handy feature which allows you to schedule it.  Instead of clicking “send”  you simply click “send later” and indicate if you want to send it 1 hour later 24 hours later or “first thing Monday morning!”

Does this email need to go out instantly?
Does this email need to go out instantly?

When will it make the most impact?

If you’re writing something at 9 PM on a Saturday night, and you know your boss has a smartphone and will get it instantly, do you really think it’s wise to send it immediately?

You may forget to send it Monday morning, so you want to “get it off your plate”.

But if you’re a new staff person, or working with a new client, it’s entirely possible your email will annoy them.

Despite what I thought when I got into consulting, your value to the client is not just how good you are at your job.  It’s also how good you are to work with!  If you’re emailing them at all hours and interrupting their lives, that may be a significant liability!  This is true, too, with employment situations.  People like to work with people they like to work with!

The beauty of email used to be it was asynchronous.  You can send it when it is convenient, and the recipient could answer when they logged onto their email.  It might be an hour later or it might be next week if the user wasn’t on email much.  It was a solution to the “interruption communication” of phone calls and “drop ins” without the need to “schedule ahead”.

Now everybody’s wired for sound.  When you send an email my phone buzzes. 24/7.  Some of us turn our phones off at night, but others are too “hooked in” and let them buzz all night.

Don’t be “that guy” who emails something totally not urgent at a time when people have their phones on in case of emergencies.

They will not read it immediately, or if they do they will be annoyed and/or forget to reply when they get to their desk Monday.


Part of it is learning your colleagues/clients and their styles. If they focus on writing and concentration in the morning, send it at lunch time or after.  If they like to “clear the slate” and deal with email first thing, then send it then.  It is amazing HOW FEW people pay attention.  If you are a junior staff person, and you take the time to understand your colleagues work habits and show yourself to be team-centered rather than self-centered, that will really make you stand out.  You’ll get more done, the work will go easier, and you help create an effective team or organization.

Active Inbox (and no, I don’t get a commission 😉 ) helps you do this.  Just click “send later” and schedule when you think the recipient would most benefit from receiving the email.

my email 2
If your email will get the best reception, and quickest action if you sent it Monday morning, why would you send it out on a Friday at 4:30 in the afternoon?

This goes to the overall point that I advise early-career staff and entrepreneurs of.  Don’t just do things to DO them.  Do them so they will be EFFECTIVE.

The goal is not “crossing it off your list”.  The goal should be doing things in a way that produce the greatest positive effect with a given effort!


The Early Bird Gets the Worm

Another advantage of email schedule management is that you can CHOOSE when the email goes out.  It may not be a delay for “second thoughts” you want, but some other function.

Many people, colleagues and clients, are “Early Birds”.  I am a night owl. I’ve been known to send emails at 3 AM Sunday morning.  While that’s just my “style” to email when inspiration strikes, it is not a good idea for many people for two reasons:

1. Some organizations have a culture where that would be considered “weird”.  If you are a junior staff member in an organization of 8-5 workers and you’re emailing in the wee hours of the morning, they’ll think something’s probably wrong with you.

My style is more brilliant “mad scientist”, and people expect me to be a bit eccentric as that’s part of my value as a partner is the “out of the box” “crazy ideas” that can really take things to the highest heights.  My clients also know I’ll do what I say I’ll do and I’ll do it well. So I’m not really worried about it.

But if you’re junior in your field in a position of needing to demonstrate reliability to co-workers or clients, or you want to “mesh” with a culture that is not your own, it may be VERY useful for you to send emails at 7:30 AM instead of 11:30 PM.

By scheduling things that conform to others’ expectations you keep them happy, and you get to work in the manner you’re most productive.

2. Drawing Boundaries

This is the one where I probably should adopt this practice of queuing things for the next day.

This is important: If you answer emails at all hours, people will expect you to answer emails at all hours!!!

There is research that shows that people will “push” expectations based on what they can get away with.  If you maintain strong professional boundaries, and only work within the hours you are required to work, and do things that are your job but not “everything” that someone might dump on you, people often will respect this.

As someone who tends to “go overboard” for clients, I find myself answering emails late at night when I should be sleeping, and replying on weekends to questions, etc..

If you always reply during business hours, people will expect you to reply within business hours.  This can often keep them from contacting you at “all hours”.  But it also takes the heat off of you.

When I took my first graduate management course, years ago, one of the fascinating things to me was the notion of the “social contract” that gets forged early in a work situation.  During the early period of one’s employment, expectations are set that will last for years to come.

Your behavior with respect to colleagues is viewed partly based on what you DO but also partly on what you to RELATIVE TO the expectations they developed early on in your time with the company.  We tend to be more “eager to please” and “go the extra mile” when we are in a new job or a new client relationship.  It is important to set appropriate boundaries though!  You can do more than is expected and really over-deliver but it may be good to set certain expectations that are viable for the long-term.

If you don’t want clients contacting you Sunday morning, don’t give the expectation that you’ll reply on the weekends!

My recommendation is that DO go the extra mile, and over-produce, but hold those emails to reply during business hours, unless there is a compelling “emergency” or reason to send during off-hours.

You can still work evenings and weekends as you want to for colleagues and clients, but there’s no sense giving them the expectation that you’re available 24/7 as they will be disappointed if you ever decide to change that.  It’s easier to set firm boundaries, then relax them later than it is to “take away” something people have come to expect!

So there!

I hope this post provided some ideas and insights into how you can use low-cost or free email tools to help make your life easier and help keep your colleagues and clients happy!


If you have any comments about this article, or want to see how Root Deeper Marketing can lend our experience and talents to your efforts, please feel free to get in touch!

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