Dave Kerpen | 11 Simple Secrets to Handling Emails on Vacation
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11 Simple Secrets to Handling Emails on Vacation

11 Simple Secrets to Handling Emails on Vacation

Soon, you’ll be relaxing on a beach, cocktail in one hand, book in another hand. It’s summer vacation time!

But those emails just don’t stop coming in. Email communication is a blessing and a curse. It’s always-on, which gives you the opportunity to be productive anywhere and anytime, but also can keep you from turning it off when you want to. So how do you handle emails in preparation for and during your vacation?

To answer that question, I talked with 11 members of the Young Entrepreneur Council, an invite-only organization comprised of the world’s most promising young entrepreneurs. Here are the 11 best tips I got from these entrepreneurs on how to handle emails when you go on vacation:

1. Commit and Communicate

Everyone has a different comfort level when it comes to “unplugging” on vacation. Whether you’re stepping away from email completely, checking in once a day, or keeping your iPhone by your side, communicate that clearly and stick with it! Nothing is more confusing than getting someone’s “I’m unavailable for a week!” auto-responder and then getting an email from them 15 minutes later.

Brittany Hodak, Co-founder, ZinePak

2. Delegate

Delegate emails to an assistant that you trust. You can easily set up email delegation through Gmail so anyone can respond to emails on your behalf using their signature while being unable to access your personal password. Once you come back from vacation, you can review the messages that were sent and make comments to improve the process.

Liam Martin, Co-Founder, Staff.com

3. Utilize Out-of-the-Office Messages

If you’re truly trying to digital detox, just let people know. They’ll get it. Save yourself from having multiple emails from one person and potentially hurting relationships before it can happen.

Brooke Bergman, Co-Founder and Vice President, Allied Business Network Inc.

4. Check Every Morning

Check your email once a day early in the morning while others are getting ready, sleeping or when you have some personal time. Depending on what kind of vacation you’re on, if you do this and stick to it you will feel better about being away from the hustle and bustle of work. You will also still stay on top of any potential major issues or work emergencies.

Jason Grill, Founder JGrill Media | Co-Founder Sock 101, JGrillMedia | Sock 101

5. Keep Your Emails Short

Give yourself no more than one hour per day to answer emails. In this time, you should be able to respond to all urgent messages IF you keep each one brief and to the point. Your vacation is not the time for long, drawn-out explanations. In a situation where one is required, tell the person you’ll get back to them promptly when you return.

Alexandra Levit, President and Founder, Inspiration at Work

6. Give Them Your Full Attention for 30 Minutes

First, set up an out-of-office message. This helps manage expectations. Then, clear out no more than 30 minutes per day to check your email. You won’t be able to “attend” to emails on a regular basis so don’t try. But for those 30 minutes, give them your full attention. Process emails and put them in the right action category. You can work on them once the vacation is over.
- Ashish Rangnekar, CEO & Co-founder, BenchPrep

7. Create a Bat Signal

Before leaving for vacation, ease your team’s mind by creating a ‘bat signal.’ My bat signal is a text message. If I get a text, I know I need to look at my email immediately because something needs my attention right away. More often then not I never receive one, but the comfort of knowing I am never too far to answer an email is a relief for my team, my clients and myself!

Kim Kaupe, Co-Founder, ZinePak

8. Anticipate the Bottleneck

When you respond to your email, avoid posing questions with no clear next steps. For example, instead of saying, “Does Brian have the latest paperwork to move forward?” say, “Does Brian have the latest paperwork to move forward? If not, please get it from John. If he does, please ask him to submit it by 5 p.m. tomorrow.” That way, you aren’t the bottleneck, and your team isn’t waiting for you.

Phil Dumontet, CEO, DASHED

9. Consider Timeliness and Accessibility

Put alternate contact information in your email vacation responder. This should ideally be your assistant or someone who can respond to the questions in a timely fashion because there will likely be delays in your replies due to time zone differences or other activities. You can also provide alternative phone numbers or emails they can use to reach you if it’s urgent.

Gideon Kimbrell, Founder/CEO, InList Inc

10. Prepare Ahead of Time

While you’re on vacation, you should actually be on vacation. That means not answering emails or other communication related to work. That also means preparing far in advance to allow your company to operate without you. If you have to answer emails on vacation, you’re not truly prepared to take a vacation. You need to make changing that a priority.
- Mark Cenicola, President and CEO, BannerView.com

11. Flag Anything That Requires a Response

If it sounds simple, it’s because it is: Flag everything you need to reply to, and when you start going back through flagged items, start at the beginning.

John Roa, CEO, ÄKTA


These are 11 tips from successful entrepreneurs. For me, the most important secret is to not send email. The less email I send prior to and during a vacation, the less I’ll receive. (By the way, this is true 24/7/365, not just during vacations! Try sending less email, you’ll be amazed by the results!)

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