“Can I work remote?”

I cringe. It’s Ian and Ian is a senior engineer. He’s a rock. He gets it done. I never have to ask him twice and, after six years, Ian has every right to ask to work remote. But I’m still freaked because my first thought when anyone asks to work remote is, “This fine person is a year away from either quitting or being fired.” Why? Because they’re asking to leave the Pond.

The Pond

When I think of communication in a large group of people, I imagine a pond. Small, round, slightly green water. You can see the edges of this pond and there’s a willow tree over there looking both informed and sad. Metaphorically, all the people in the organization are standing somewhere on this pond. Our positions are based on whom we know and where we are in the organization chart. When something happens in the company, when something noteworthy is said, a drop falls in the pond and creates a ripple.

The ripple is the piece of information traveling from one person to the others. Big drop, big ripple… travels further.

With me so far?

There is a constant flow of information in your company. That means there are constant drips in the Pond, creating various-sized ripples traveling every which way, bumping into each other, and transforming each other into slightly mutated ripples. These mutated ripples are the rumor mill, gossip, and all those small pieces of slightly bizarre information that cross your path during the course of the day.

If you’re in the Pond, you’re gathering data, whether it’s intended for you or not. It’s inevitable. It’s what we do as curious humans; we receive information, digest it, alter it, and then send it on its way tweaked to our own personal wavelengths.

A remote employee is not in the Pond. Yes, he’s on the mailing lists and he aggressively updates the wiki, but the subtle, unintentional, tweaked, quiet information that is transferred throughout the Pond doesn’t leave the Pond. There are those whose jobs it is to look at the Pond and attempt to relay the interesting ripples, but while these program and project managers are well intentioned, they relay poorly because they’re just single observers of ripples. Real information is never conveyed by the individual; we understand by listening as a group.

The group forms a collective picture of the state of the Pond – it’s a distributed picture understood by everyone, but never completely known by one. It is the unspoken royal “we” and this intricate, immeasurable thing is absolutely essential to how a group gets things done well.

Do you mean it?

Remote has to work. It’s not just Ian. There are bright people in your building right now who are going to want to return home to Colorado, and you’re going to let them because losing them is not an option. Also, there’s a planet full of talented people who will always be at a distance, but who represent huge, untapped productivity for your team. Your challenge is how to augment the remote employee’s absence from the Pond.

This article is about how to decrease the risk that you will have to fire your favorite employee who decides to become remote. I’d like to give advice from the other side, on how to work remotely, but I’ve never done it. I don’t have the personality. My professional satisfaction comes from being able to look those I depend on in the eye and ask, “Do you mean it?” There is essential content to be discovered in that stare that will never be fully conveyed in an email, IM, or tweet.

My belief is that without deliberate attention, the remote employee slowly becomes irrelevant to the organization. Through no fault of their own, they can be gradually pushed to the edge of what’s important. And when you’re at the edge, you’re an organizational shudder from falling over it. Failure happens at the edges.

Avoiding failure involves asking four questions before they leave:

1. Do they have the personality?
2. Do they have the right job?
3. Does the culture support it?
4. Do you have a remote friction detection and resolution policy?

The Personality

Whether the employee has the right personality to be a productive remote worker is a tricky call because most of your data about this person is based on working with them. What’s going to happen when you can’t see them? How are they going to react when you forget to include them in the staff call? How are they going to feel when the product launches and they aren’t there to celebrate?

This is what I consider.

Are they eloquent in email? Every bit of communication is more expensive with remote folks, so they’d better be good at it – no matter the medium. Can this person construct and convey a complex argument in a single email? Can this person make an important point… via iChat? Written communication is bereft of much of the intangible value of the Pond. It lacks the nuance of face-to-face communication, which means the author needs to be painfully explicit about the details. Can this person do that?

Are they self-directed? How do they deal with ambiguity? If you’ve given them crap direction, do they bump around for a bit before admitting defeat, or do they immediately ask for clarification? Many of the subtle ways you check in and error correct co-workers leave when they leave. If they’re in the weeds, are they going to ask for help? How long until they ask for help?

How detail-oriented are they? If self-direction indicates how they start a thing, their detail orientation is how well they finish. Is this a person who needs help across the finish line? Do they get lost in nonessential details? When you ask for a thing, are you getting the end result you expect?

How well do they know the Pond? We’ll talk about their job in a moment, but whatever that job is, it will have dependencies on people they are leaving behind. Does this person know how the organization communicates? Do they know both the organizational structure as well as the social structure? Are they asking you who to follow up with or are you asking them? Are they instinctively aware of whom they might piss off and proactively account for this in the first mail rather than after the flame-o-gram?

Do they need the Pond? Knowledge of the Pond is great, but does this person thrive because of the Pond? How much of their day are they spending talking with co-workers? Is this conversation essential to what they do or purely social? Which part of them are you going to socially amputate when they’re no longer in the building?

Are they reliable? I imply at the beginning of this article that it’s a senior employee who has a better chance at being successful remotely, but that’s not true. The ability to work remotely is not entirely a function of seniority; it’s also genetic. There are those who do it better solo. Their standard operating procedure is to simply get it done. Seniority can improve personal efficiency and the quality of the finished product, but I’ve discovered innate reliability at all levels of experience. There are people who simply do what they say they’re going to do.

The Right Job

Typical corporate logic dictates that a remote employee should work on a project that is separable from the rest of the team’s. The reasoning here is flawed. The belief is that the inconvenience of communication and decision-making latency around their distance means they should be separated and placed on non-dependent work.

Every part of that reasoning is wrong. Every part is another reason that remote fails.

My most successful remote employee was a perfect anomaly. He wrote standards — protocols. The heart of his job was to define a structured means of communication where the primary goal was the removal of ambiguity. He was a phenomenal communicator. He went out of his way to completely and promptly answer every email. 24 hours a day. When he visited, he took the time to do a complete circumnavigation of the Pond, vetting all the ripples he could find. He instinctively knew that the skill in defining a protocol is creating a structure that is going to meet the needs of right now, but also the unimagined needs of five years from now. And he applied that not only to what he wrote, but also to how he worked. He was a wonderful anomaly and he taught me that a remote job must be perceived, in all ways, as equal to a local one.

There should be absolutely no consideration of a person’s location on the planet Earth when considering the work you need of them. Each time the concern “Well, they’re remote” comes up, you need to turn the concern around and ask, “What about my company, my people, or the work makes remote an issue?” because that is what needs to be considered locally.

The Culture

How are those back in the Pond viewing the remote employee? The means by which Pond-based employees discriminate varies from the discreet to the direct, from the passive to the aggressive. The reason for this discrimination always boils down a single, fundamental tension: remote creates productivity friction.

The friction sounds something like this:

• “I don’t know what the hell this remote person is doing, so I’m going to assume he’s stumbling around the house in his underwear.”
• “This remote person is messing with my deadline or deliverable.”
• “He doesn’t answer his email.”

How long does it take to build a thing of quality? There’s a cost and the question is how is the remote worker affects this cost. Anything higher than the cost of a local employee creates friction. What was a 27-second walk down the hallway to yell at Bob about his crap code is a now 30-minutes constructing an email. Staff meetings start with a wasted 10 minutes trying to get the videoconferencing to connect. Every single communication with a remote worker costs more and generates more ripples in the Pond, and both their job and yours is to either make this cost go away or justify it.

Respect comes from knowledge and the question is: does your culture support a constant and consistent flow of knowledge to and from the remote worker?

Let’s find out:

• Have you created or implemented specific communication media for the team? Wikis? IRC? Are they used? Do different teams need different media? Are there too many and, if so, how are you going to anoint the one true medium?
• Other than the job, how are you encouraging other random interactions between local and remote folks?
• How often are you seeing these remote folks face-to-face? My vote is at least monthly.

Friction Detection

Remote friction is going to crop up. Just like interpersonal tensions randomly appear in the building, so does friction around remote employees. What are you doing not only to detect these, but also fix them? An example.

I hate meetings, but the brilliant thing about a meeting is that it’s full of people, and in a room full of people you never quite know what the hell is going to happen. The knee jerk reaction to bridging this meeting gap when there are remote workers is always, “We need good video conferencing software.”

After 10 years of hearing this argument, I’m calling fail. Video conferencing works when you need to talk to your kids during that trip to Chicago. It fills that visual gap, but all of the video conferencing solutions I’ve been a part of relative to a meeting create friction rather than remove it.

Yes, I can see Anne on the screen, but she’s flat. She’s also got this 1/10th of a second lag on the conversation, which doesn’t sound like a lot until you’re in the middle of that strategic rant about design and Anne chimes in, mid-sentence, with a bright thought that completely disturbs the creative cadence of your rant. That 1/10th of a second. Her inability to inject her essential thought at precisely the right moment. These micro-disturbances of the Force are a constant reminder that Anne’s not there. She’s being projected on the conference room wall like a well-intentioned screen saver. This isn’t just hurting the tempo of the meeting, it’s eroding her credibility.

In this case, surprisingly, less technology, rather than more, is better. Skype’s proximity to my computer and the usual lack of lag is far superior to video conferencing for 1:1s, and spending a little money on a quality Polycom is a fine solution for the staff meeting, but technology is a tool and never the answer.

Friction detection is paying attention to all the ways a remote employee interacts with the group and constantly asking, “Is this working?”

Another Pond

You, as the manager of people, are responsible for making the remote call regarding a person, putting them in the right job, and making sure the culture supports remote people. But the responsibility of delivering while remote is squarely on the remote employee. Yes, a remote employee answers to himself. At four in the afternoon when they run into an impossible problem, it’s almost entirely up to them to develop their plan of attack.

Working remotely isn’t a privilege; it’s work. And it’s the same work we’re all doing back at the mothership… fully clothed… in the Pond.