Inbox Shadowing: Epic Email Management Hack Saving Hours Every Week

12 min read

US president John F. Kennedy was well-known for a unique and powerful skill: The ability to remember the names and details of almost every single person he’d ever met.

And although other leaders after him may have been charismatic, few possessed this uncanny skill (probably because they never read Forget Me Not: 7 Tips to Remember Names).

But once that precedent was set, there were expectations to live up to. And so, short of Kennedy’s extraordinary memory, many world leaders now deploy a special individual called a “shadower.”

A shadower is someone who walks the crowd with the president at important events, whispering pertinent personal information in the leader’s ear about approaching attendees.

For example: A shadower might inform the president that a California senator’s 19-year-old daughter is attending Princeton this fall. With this information at hand, the president is able to deliver a highly-relevant, personalized interaction to the senator, thus forming a deeper, more meaningful connection.

Can you see how something like this might be valuable? Now, let’s apply this concept to the digital world. Realistically, you probably don’t need someone shadowing you at board meetings or fundraising events; but there is another way you can leverage this practice in your email management: Inbox shadowing.

What is Inbox Shadowing?

Inbox shadowing is a unique email management concept we developed for our clients after learning many of them often spend an upwards of 3+ hours on email management each day, even with the Inbox Zero approach (which involves checking email 3 times a day with the intention of keeping the inbox empty).

The problem with most people’s current email management (or lack of) is that it’s often a productivity trap. Most people treat email management as a reactive task, operating on a “last in, first out” basis without giving any weight to the importance of individual emails.

And although sorting and responding to emails might feel productive, it probably isn’t the most productive use of your time. But it’s just one of those things that has to be done, right? Yes, but not necessarily by you. And that’s where this epic email management hack comes into play: inbox shadowing.

Put simply, inbox shadowing means empowering your assistant to manage your inbox as if they’re you. In other words, they become your digital “shadower,” making decisions about your email management based on their abilities and the context and permissions you’ve provided.

More specifically, a well-trained inbox shadower will do three things to handle your email management:

#1: Draft Responses to Emails They Know How to Handle

You may be surprised just how many emails can be handled without your direct involvement.

For example: If one of your board members asks for a 15-minute meeting next week, both you and your shadower know you’re going to say yes. So they can draft up a response accepting the request and, because your shadower would also have access to your calendar, they could even offer up some available time slots.

Then, at the end of the day, all you have to do is quickly review the draft they wrote and press “Send.”

#2: Label “Please Handle” Emails

Occasionally an email will arrive in your inbox that your shadower won’t be able to handle without your involvement. For example: You may get an email from a team member requesting your feedback on a project.

In these instances of email management, they’ll label the email “Pls Handle” so you know it requires some form of action from you.

#3: Label “FYI” Emails

In most cases, the majority of the emails that arrive in your inbox don’t require response or action. These “status update” emails are usually important, but aren’t necessarily urgent.

For example: You may get an email from another team member letting you know the project you assigned them has been completed.

In these instances of email management, your shadower will label the email “FYI” so you know all you have to do is give it a quick skim at the end of the day.

The Death of “Last In, First Out”

Properly implemented, this concept of email management results in a cleaner, more streamlined inbox that might look something like this:

And now you no longer have to reactively review every single email that comes in with the “last in, first out” approach to email management. Instead, your optimized email management workflow will look something like this:

  1. Review and send any and all drafts created by your shadower.
  2. Review and process all emails marked “Pls Handle.”
  3. As you find time, skim through all emails marked as “FYI.” Often, you only need to do this step once a day.

Ultimately, inbox shadowing enables a fundamental and positive change in your (once-tumultuous) relationship with your email management. Let’s take a closer look at some of the benefits of this effective email management concept.

The Benefits of Working with an Inbox Shadower

After years of implementing inbox shadowing with dozens of entrepreneurs, executives, venture capitalists, and business leaders, I feel confident in saying that the benefits of this email management practice are many; but let’s take a closer look at 5 of the most impressive.

#1: You Can Reduce Time Spent on Your Email Management by Up to 80%

Research shows that over the course of a day, the average employee checks their inbox 96 times and spends nearly 3 hours on email management. That equates to one email-related task every five minutes!

But as we’ve discovered here at Mindmaven, 60%-70% of emails don’t require your full attention or decision-making abilities. Therefore you can save between 50%-80% of your email management time by shifting the drafting responsibilities to someone you trust while you simply review and press “send.”

Why Don’t Shadowers Just Send Emails Themselves?

You might be wondering, “Well, why not have the shadower respond to the emails right away instead of drafting responses for me to send later in the day?”

Here at Mindmaven, we believe that being genuine is extremely important in relationship management; and in order to stay authentic, it needs to be you that actually sends the emails.

Outsourcing the sending of emails without your review is not only disingenuous, it can lead to mistakes, miscommunication and—in the worst-case scenario—distrust if someone discovers you aren’t answering your own emails.

Even though you still have to take the time to review the drafts before they’re sent, inbox shadowing can still significantly contribute to saving you 12+ hours every single week. This email management concept is even more powerful if you use your new-found time for Whitespace projects, allowing you to focus on the things that matter most.

Want to learn more about Whitespace Time Management? Download our free book, Whitespace: The Entrepreneur’s Guide to Proactive Time Management.

#2: You Can Free Your Mind from Distractions and Anxiety

One of the most rewarding parts of my work is seeing the sheer sense of liberation my clients feel the first time they work with an inbox shadower to revolutionize their email management. This is the first time they realize how enslaved they’ve been to their inbox.

Even with the successes some people have had with the Inbox Zero email management approach, many worry they’ll miss important information. But with inbox shadowing, that fear goes away because they know two things:

  1. Another set of (highly-trained) eyes are looking at emails ahead of you, and
  2. They’ve been instructed on best practices for anything urgent.

Having an inbox shadower who truly knows how to handle these urgent situations can even make or break a deal. Let me share a quick story to illustrate this:

The shadower for one of my clients, a prominent Silicon Valley venture capitalist, actually interrupted a meeting after a time-sensitive email came in.

Under normal circumstances, it would have taken my client 2-3 hours before they even saw the email, but the shadower’s quick decision allowed him to respond immediately and, as a result, win the deal.

Examples like this beautifully illustrate how an inbox shadower can eliminate email-related anxiety. You never have to waste time worried about missing vital information or losing opportunities because you know you have someone constantly watching your back.

#3: You Can Better Focus on What Matters Most

One of the most open “secrets” in Silicon Valley is that the most successful CEOs are those who focus solely on the things that move the needle most.

But if you’re not one of the demi-gods of the startup world, your day-to-day workflow is probably heavily influenced by your email management. The problem is, when your prioritization is driven by your inbox, you’re stuck working on things that are urgent but not necessarily important. Let’s look at a quick example:

Imagine you’ve finally carved out time for the incredibly important task of defining your marketing objectives for the coming year.

You’re 15 minutes in when you get an email from a team member: They need some time-sensitive support for a new hire and you need to write a follow-up email.

Without an inbox shadower, you’d have to stop the important work you were doing to focus on the urgent task in your inbox. With an inbox shadower taking care of your email management, you can rest easy and stay focused, knowing a draft will be created and all you’ll need to do is press “send.”

This concept of email management not only makes you more effective, it enables your team to be more effective because they’ll get the answers and support they need as they need it, rather than when you can get around to it.

#4: You Can Dramatically Increase Your Velocity

One of the most common reasons things don’t move as quickly as they should is because they get stuck in an executive’s inbox.

This isn’t necessarily because responding to the email requires a difficult decision; it’s just that there isn’t enough time in the day for them to get through all their emails while still moving the business forward.

But when you have a shadower who can “preload” your decision, you can just click “send” on simple emails. That way there’s no need to spend 30 minutes on your email management before getting to an email that only takes 5 seconds to act on.

When inboxes are processed more efficiently, this often not only increases the velocity of the CEO; it increases the velocity of the startup as a whole. After all: The velocity of a startup can never exceed that of its leadership.

#5: You Can Enjoy Deeper, More Meaningful Relationships

Many people in Silicon Valley—and likely the rest of the US—have grown used to the one-liner email. And while this type of communication is growing increasingly acceptable, that doesn’t mean it’s optimal. In fact, it can be very damaging to your relationships.

Don’t get me wrong: I’m a fan of brevity. But there are situations where putting a bit more time and thought into a reply can go a long way towards deepening your relationships and making people like you. For example:

Imagine somebody sends you an email asking to reschedule a meeting because their child is in urgent care.

A busy executive without an inbox shadower would likely respond with a one-liner like, “No worries, my assistant will help you set up a new time.”

An inbox shadower, on the other hand, has the time to respond with something more thoughtful and empathetic, such as:

“I’m sorry to hear your son is sick. As a parent myself, I know there’s nothing scarier than a child who isn’t getting better. I’m glad you took the initiative to get him to urgent care. Please keep me updated.”

In a world of one-liner emails, a message as meaningful as that is going to make a strong, positive impression on the other person and dramatically deepen your relationship.

The Key to Successful Email Management and Inbox Shadowing

All of this said, inbox shadowing isn’t right for everyone. But if you’re in any form of leadership—or if you spend more than an hour each day on your email management—the decision should be a no-brainer.

As long as you get yourself a properly trained inbox shadower, the benefits far outweigh the investment.

But the key, as I said above, is having the right shadower. Not every assistant has what it takes to exercise ownership over your email management. That’s why we at Mindmaven created the role of the Engagement Manager.

An Engagement Manager (EM) is a specially-trained assistant focused on getting you more leverage on your time, your relationships, and your resources. They’re specifically trained in inbox shadowing, in addition to a number of other unique and high-value skills.

If you think inbox shadowing (and saving 12+ hours a week) would be a valuable solution for your situation, we’d love to explore the possibilities with you. Click here to set up a free, no-obligation consultation call with one of our coaches!

We’ll look forward to hearing from you soon!

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