Using Technology to Stay Connected While Out of the Office

Our Panelists

Alexander Paykin (AP), Greg Siskind (GS), Dennis Kennedy (DK), and Allison Shields (AS).

What do you do in advance of taking a vacation to prepare for being out of the office?

AP: There’s just so much…

1. Set up auto-respond to email
2. Set up instructions for call handling with my receptionist service
3. Go through my calendar prior to planning a trip and make sure to clear my schedule
4. Update my availability on my calendar to reflect that I am  on vacation so that my automated calendar (Calendly) does not schedule new client consults during those days
5. Look into WiFi access at my destination
6. Look into cell (voice and data) signal at my planned destination(s) and decide whether to rent a satellite phone—especially important for international travel to less-developed areas
7. If traveling to countries with restricted internet access (e.g. Cuba, China, Russia), look into access to my cloud services (e.g. Clio, Google Drive, etc.) from my destination
8. Go through all the matters in my practice management system with my covering attorney to make sure all questions/issues are addressed prior to my departure

GS: Change my voicemail, try to catch up on email before leaving, change email out of office message. I may also download documents I need to read in case I’m having internet issues.

DK: I go out of my way to do backups of my computer files, including to several cloud services. I use a checklist to be sure to pack all cords, cables, and adapters I might need. And I make sure that my calendars and to-do lists show as empty.

AS: I try to plan well in advance when I am going on vacation; at least a month before I am going to be out, I take a look at all of the deadlines—not just up to the time I will be away, but for about two weeks afterward. This helps me plan to get as much done as possible before I go away. I know that additional things will arise while I’m gone and don’t want to be too overwhelmed when I return. For example, if I have something due within a few days of my scheduled return, I try to get it done—or at least get started on it—before I go away. That way I can be much more relaxed on my vacation, instead of worrying that I have a big project looming as soon as I get back. Before I leave, I schedule the most important tasks or projects that need to get done when I return, leaving time for catching up on email, calls, and anything else that came up while I was gone. This makes it easier to get back into work mode after my vacation and ensures I’m staying focused on my most important projects. I will also try to let my clients know in advance that I will be out of the office so that they are not surprised if they can’t get in touch with me.

Before I leave for vacation, I like to take some time to clean up my office, my email inbox, and my to-do list so that I know I haven’t missed anything and I can relax. It also makes it much easier to return to a clean office space and to see what new work has come in while I’ve been gone if I had things cleaned up in advance. This may mean working a bit late for a couple of days before going away, but it’s worth it.

If you must work while out of the office, what solutions do you employ?

AP: A laptop on WiFi or using my phone as a hotspot for anything that requires drafting or large document review, and a cell phone on its own for simpler tasks (e.g. emails, task assignments, calls, updates in my practice management system, quick reviews of documents).

GS: I have worked mornings from home for years so traveling is not that much of a change. First, get a hotspot from your phone provider. This means you don’t usually need to search for WiFi and you have a secure connection. I also have a MacBook which is light, fast, and has excellent battery life. I try and keep up with emails when I fly, so I subscribe to my airline’s internet service. We have web conferencing software so I’m often able to participate in meetings by video which helps make it seem a little more like I’m in the room. Our digital phone service has apps for my cell phone and computer that allow me to receive and make calls as if I’m at the handset in the office. In short, you can set up a remote office virtually anywhere if you’ve got the right software and internet or phone access.

DK: An important solution for me is letting all calls I’m not expecting go to voicemail, so I can deal with them on my terms when I want. Everything I do is available through cloud services these days, so those cloud services and mobile apps are key elements of my plan. I’m also a fierce advocate of using VPNs and other good cybersecurity practices, especially in hotels and any place with public WiFi.

AS: I try to keep work to a minimum when I’m on vacation, although there are certainly times when I have to work when I am out of the office. In those cases, I make an effort to limit myself to the “must do” items or projects and not get sidetracked into working on other projects or obsessively checking email. I may do a consultation with a potential client or a session with a client while I’m away, but I make sure to let them know that I am out of the office and that they shouldn’t expect any follow up until after I return to the office. If I am on a deadline for a column or article, once I’ve finished that project, I put work away for the remainder of my vacation. Otherwise, I may check email—at most—once a day, just to make sure there aren’t any emergencies, and then flag anything I need to follow up on when I am back in the office.

When traveling internationally is there anything specific you need to do to increase security and ensure accessibility?

AP: Four key tasks:

1. Pre-install VPN and make sure the VPN provider will work with the destination country
2. Make sure your computer drive and cell phone are encrypted
3. Run virus and malware scans on both devices prior to travel
4. Disable fingerprint and face ID prior to reaching first security checkpoint and replace (temporarily) with complex passwords

GS: First, most phone providers now have packages where you pay a small amount (AT&T is $10/day) where you get the same plan as you have in the US and don’t have to worry about long-distance or data charges. Note that not all countries are eligible as we learned recently when we got high charges because our phone was pinging cell phone towers just across the border in a country that wasn’t included. If you must use WiFi outside of your hotspot, make sure you’re set up with a Virtual Private Network (VPN) in order to ensure you’re connecting securely. Be very careful about using a computer in an internet cafe or elsewhere as your keystrokes and internet history may be tracked.

DK: First and foremost, you must understand any specific risks, traveler warnings, and advice for where you are traveling. There are many web resources with great tips and recommendations. I think that you need to ramp up the physical security of your devices to prevent theft or damage. VPNs, drive encryption, and selective file encryption are also important. Having a list of key info, numbers, and copies of documents with you (and backed up on the cloud) is something else I’d recommend. And, of course, you have to let your bank know that you are traveling abroad so they don’t shut down your payment cards, make sure you have the right power adapters (and backup batteries), and get an international calling and data plan in place for your trip.

AS: So far, when traveling internationally I haven’t had to worry too much about connecting to work or about sending or receiving sensitive documents or information. I do make sure to switch my phone to an international plan while I’m away so that I have access, and try to use only secure wireless networks wherever possible if I need to connect.

Do you need to travel with a laptop or is a tablet adequate? If you only travel with a tablet, what programs are critical?

AP: I prefer to travel with a laptop as most tasks I would do on a tablet I can do on my phone.  The only time I need something larger than my phone is when I need a full-sized screen and keyboard. In those circumstances, I find a laptop to be more effective as it has all the same software as the desktop and generally has more power and functionality.

GS: If you’re not doing heavy work and are just checking emails and web sites, a tablet may be fine. But make sure sites you need to access can be viewed on the tablet device you’re using. This has mainly been an issue over the years for Adobe Flash and iOS devices like the iPad and the iPhone. But as most sites have moved away from Flash in recent years, it’s less of an issue. I recently ditched my laptop for my iPad on a trip and all was fine. A key purchase was the iPad’s integrated keyboard case, which is excellent and made it seem like I was on a laptop. Now that so much of my work is in the Cloud and apps on my iPad allow me to access most documents, this worked pretty well. Some iOS apps are still not as good as their desktop versions, but most are perfectly fine.

DK: I have a 12” MacBook, which is thin and light, so it’s not a big deal to travel with it. However, if I’m not doing presentations or planning to do a lot of writing, I’ll leave it at home and travel with my iPhone and iPad. I’m planning to experiment with using only an iPad Pro for travel in the future. Cloud-based services, tools, and mobile apps are the key to a tablet-based approach. If you plan to do a lot of writing, you probably need an external keyboard for a tablet. If you match apps on your tablet with programs on your computer, I’m not sure these days whether you miss much in the way of day-to-day functionality with just a tablet. You’ll want to think through exactly what you will be doing on the trip and try to envision how you will do each task and where problems might arise.

AS: I have found that my tablet is of limited use when I travel—if I need something more robust than my phone, it is usually because I need a keyboard, and traveling with the laptop is much easier than traveling with a tablet and a keyboard. If I only plan to respond to a few emails while I’m gone, my phone is fine for that purpose. If I’ll be doing any kind of writing and will need the keyboard, my laptop is much more comfortable, and not that much more difficult to transport than my tablet.

Do you set an out of office reply while on vacation, and if so, what do you include in your away message?  Have you seen any particularly catchy messages used by others?

AP: I keep it simple and advise that: 1) I will be out of the office with limited access to phone and email; 2) Provide contact info of my covering attorney and paralegal for anything urgent; 3) Advise that while away, I will be responding to all emails within 24 hours and will respond with phone calls subject to time zones and other limitations.  I should also say that I only set up an auto-responder when I am traveling far enough out of the country that time zones become an issue. Generally, if I have travel within time zones where I am awake during normal New York business hours, I simply answer all my calls and emails on the go, as if I were in the office.

GS: Nothing too long. I usually just want to convey my dates of absence, that I’m not checking messages frequently (or that I am), and who a person can reach at the office in my absence. I don’t really try and get clever with the out of office messages, but recently heard this was a “thing” so may try and be more creative the next time.

DK: I’ve grown to believe that no one reads out of office messages anymore and they will send people emails anyway because they believe the recipient is actually reading their email. And they usually are. If I’m really going to be “off the grid,” I might set an OOO message that simply says that I’m out of the office and will return on a certain date. I never give details of where I’ll be. I keep it brief. Also, these days, if someone needs to reach me, they will text me or call me rather than email me. I did know someone who had an OOO message that said all emails sent to him were automatically deleted by the system while he was out and that people would have to wait to email him until he got back. We all got a laugh out of that and sent him emails while he was out because he usually responded to them.

AS: Yes, I always set an out of office reply on my email when I am on vacation or otherwise out of the office, and I include the date when I will return and/or when a response to the email can be expected. I also include whether I plan to check email regularly while I’m gone—it’s all about setting expectations. I will also put an out of office message on my voicemail, or forward my office phone to my mobile while I’m out of the office (depending on whether I want to be disturbed with work calls while I’m out). Either way, I will check voicemail daily, again, mostly for emergencies, although occasionally I will respond to a message on vacation with an email reiterating that I’m out of the office and that I will get back to the caller when I return. (Unfortunately, I find that most people don’t actually listen to the message when they call,  so often they still won’t realize I’m out of the office for an extended period of time). Finally, I will often set my out of office message and/or voicemail message to say that I’m returning to the office one day later than I am actually returning. This helps cut down on calls and emails when I first get back and gives me time to catch up.