Will Working Remotely Work? 7 “What If” Scenarios To Consider First

The goal: to make working remotely look and feel as seamless as possible for your boss, your colleagues, and your customers.



For almost two decades, I’ve helped organizations implement work life flexibility strategies. And I’ve learned that the difference between success and failure with any type of flexible work, including remote work, often comes down to contingency planning. In other words, answering the question “what if ‘x’ happens…” to as many scenarios as you can possibly think of upfront.

Nothing drives a manager crazier than to call an employee who is working remotely and not be able to or reach him her. Nothing depresses a remote worker more than to be consistently passed over for high-profile, last minute projects because it’s easier to give it to someone in the office.

It’s more difficult to address these situations after the fact than it is to plan how you could handle them in advance. Misunderstandings are minimized because everyone is on the same page. This doesn’t mean there won’t be unforeseen challenges that pop up. But for the most part, my number-one tip for successful remote work is to ask yourself, your boss, and your team, “What if…?” before you start.

The goal: to make working remotely look and feel as seamless as possible for your boss, your colleagues, and your customers. Everyone is already too busy doing too much work. You want to minimize the chance that someone will have to work harder so that you can work more flexibly.

Here are the most common and problematic scenarios that can be easily avoided with some pre-planning:


“What if…you are talking to someone from work on the phone and your dog barks?”

This is the top complaint I hear from managers about their employees who work from home: background animal (and kid) noises. I’m not sure why this drives them so crazy other than it’s a red flag that says “I’m not working in an official office,” and they don’t want clients or customers to know that. In the spirit of creating as seamless a transition as possible, try to keep your pets and kids separate from where you’re working.

“What if…your babysitter gets sick or your kids have a snow day?”

Remote work can’t be a substitute for child care. I’m consistently surprised by how many people struggle with this. The rule of thumb I follow is to handle child care the same way you would if you worked in an office. Have a contingency plan in place for what you will do if your sitter calls in sick or your kids have a snow day. For example, identify someone in advance who can come in to cover, and don’t assume it will be you.

“What if…someone from work (especially your boss) tries to reach you and you don’t respond immediately?”


I’m somewhat mystified by why managers expect immediate response from remote workers since people working in the office aren’t always at their desk. But for many managers, quick and easy access to you is a clear sign that you’re working, not watching The Price Is Right (which is their deepest fear). If you happen to miss a call or IM from someone at work, reply as soon as possible. Don’t offer a lot of excuses, just explain what happened: “I’m sorry; I was on another call,” or “I stepped away for a moment. How can I help you?”

“What if…there’s an important meeting scheduled in the office on your remote work day?”

Be flexible with your flexibility. In today’s volatile, ever-changing global economy, change is inevitable and we have to roll with it. This includes being willing to alter your remote working schedule periodically to accommodate important meetings or projects that require face-to-face interaction in the office.

“What if…your internet service goes down?”

Reliable technology is one of the keys to successful remote work. That includes a reliable internet and phone connection. If your mobile phone has spotty service, install a land line.  I your internet service is unreliable, get a backup mobile wifi card. You may decide that these investments are valuable insurance that supports your ability to continue to work remotely.


“What if…a last minute important project lands on your boss’s desk at the end of the day?”

Back in 1975, when critical customer information could only be found in paper files, last-minute projects had to be handled in an office. But today, most of information that you will need to respond rapidly to an important problem or opportunity can be accessed or shared remotely from the cloud. The challenge now is for your boss to think of you as these issues arise if you aren’t physically present.

The trick is to communicate often when you’re working remotely without being annoying. First, let your boss know that even though you are working remotely you’re available and happy to step in and help anytime.  Second, periodically (once or twice a day) touch base with a quick email or IM just to check in. That keeps you in the front of her mind should any challenges arise.

“What if…someone from work calls and you’re putting a load of laundry in the washing machine?”

I mention this scenario because it came up on a recent manager webinar I conducted for a client. The manager said, “I was on the phone with an employee who works from home and all of a sudden I hear a splash and a scream, then the line goes dead. I’m thinking ‘What the heck?’ Then she calls me and apologizes by saying ‘I was putting a load of laundry in and dropped the phone into the tub.’ See, this is why I hate people working from home.” The moral of this story is that if you’re working from home, then work. Yes, throw a load of laundry in, grab a sandwich, go to the bathroom, but make it fast and don’t do it when you’re on the phone with your boss or a client.


So much of this is common sense but surprisingly few people think these situations through beforehand and end up sabotaging their ability to work remotely.

What other “What if…” scenarios can you think of?

(This post was inspired by Microsoft’s “Your Office, Your Terms” campaign to support women and remote work.  Check it out)  Also, I invite you to connect with me on my Work+Life Fit blog and on Twitter @caliyost.

[image flickr user novencito]