How to Maintain an Engaged Working Relationship When Working Remotely

Evaluate your situation on an ongoing basis and adjust as necessary

Building and maintaining strong working relationships with your managers is critical to your success in any job in any organization. That’s a tall order under the best of circumstances, and an essential aspect of effective loss prevention strategies. It’s even more challenging if you and your manager work in locations remote from each other.

Most managers and non-managers alike are so busy juggling their various responsibilities that they don’t usually make enough time for regular structured conversations, even if they are working side-by-side. Instead, most conversations probably occur ad hoc—during group meetings, in emails and voicemails, in passing, or when there is a big problem that desperately needs attention.

I call this phenomenon “management on-the-fly” or “management by special occasion.” There is no systematic logic to the timing of management conversations, in fact they are random, incomplete, and often too late to avoid a problem or solve one before it grows out of control.

The only alternative to being subjected to management on-the-fly is for you to get in the habit of having regular one-on-one conversations with every manager you answer to as part of your routine loss prevention strategies, even if you are working side-by-side with that manager. If you are remotely located from a manager for all or significant portions of your work time, then it is even more important, despite how challenging it might be, that you develop a regular, structured dialogue with that person.

Take the Initiative

I’ve heard countless stories from very determined individuals who’ve had to stalk their bosses from remote locations, calling every fifteen minutes until the boss finally answers. Or texting, faxing, Facebook messaging, scheduling two-way web-cam conferences, or even showing up at the boss’s location to try to get some one-on-one time. I hope you are not in that situation.

The best situation is for you and your boss to work out a protocol for a regular schedule of one-on-one meetings to discuss your loss prevention strategies whenever you can. Here are some best practices that you can apply if you don’t work in the same location as your boss:

  • Keep each other informed about when you’ll both be at a central location, such as the organization’s headquarters, so you can schedule in-person, one-on-one time.
  • Schedule occasional in-person meetings when it is convenient for you to visit your boss in his or her remote location or when it is convenient for your boss to visit you where you work.
  • If you have access to web-cams, schedule a regular one-on-one meeting via the web.

In the absence of in-person meetings or two-way web-cams, make good use of regular telephone conferences and various forms of electronic mail, such as instant messaging and email. Unfortunately, too often when people communicate primarily via telephone and electronic mail, they neglect scheduling regular one-on-one conversations and, as a result, their communications tend to be disorganized, incomplete, and random. Here are some best practices for using telephone and electronic mail to communicate regularly with your boss:

  • Schedule regular one-on-one telephone calls to discuss your loss prevention strategies, then honor them.
  • Prepare in advance of the one-on-one call. Send your boss an email recapping what you’ve done since your last one-on-one, the steps that you followed to get those things done, and any lingering questions or issues you have about those actions. Then outline what you plan to accomplish next, the steps you plan to follow, and any questions you may have about these upcoming actions.
  • Ask your boss to respond to your email in advance of your one-on-one conversation to help you prepare even further, for example, by including specific loss prevention strategies or any other items in the agenda that he or she would like to cover.
  • Send your boss a reminder via email or text message 30 or 60 minutes before the scheduled meeting.
  • Immediately following the call, send your boss an email recapping what you both agreed on in your conversation—the actions you need to take, the steps you plan to follow, the date and time of your next scheduled phone call, and the promise to send an agenda prior to the next meeting.

I’m often asked this question: “My boss works across the hall from me, but our entire relationship is conducted by telephone and email. What should I do about that?” My personal view is that conducting face-to-face conversations, at least once in a while, is much better than conducting your management conversations solely by telephone and email. I suggest following the same best practices outlined above, plus once in a while, walk across the hall and try for a face-to-face meeting. You can poke your head in and ask, “Did you get that email I just sent you?”

The Importance of Documentation

Even if most of your communication is through telephone and email, that’s better than nothing. And there is an advantage—you are creating a paper (or electronic) trail. Save those emails and you’ll have record of your ongoing dialogue with your boss about your loss prevention strategies and other work issues. If the emails are organized and thorough, then you might be able to print them and use them as check-lists, or use them as the basis for crafting work-plans, schedules, to-do lists, and other tools to help guide you in your work.

One of the hidden advantages of remote work relationships is discovering, tapping into, and leveraging the power of ongoing documentation. Just by documenting your ongoing dialogue with your boss in advance emails and follow up emails, you are tracking your own performance, giving yourself written records every step of the way. Over time, you find you have records going back months or years that reflect your assignments and performance of tasks, responsibilities, and projects. By communicating remotely with your boss in writing, you might find that you more often are working from a written plan and regularly updating your goals and timelines, routinely checking things off a to-do list and taking notes every step of the way. You will find you are constantly taking more thorough, organized, accurate notes, and then referring to those notes in subsequent conversations with their boss. In fact, you might find that you are keeping such close track in writing that your managers start to rely more on your written records than the manager’s own system.

If you are working remotely with a manager and you want to be considered meticulous and trusted by your boss, then you need a tracking system to document your own performance on a daily basis. Tracking your own performance in writing will add so much clarity to your management relationship. Simply talking about loss prevention strategies, expectations and performance is not enough. Writing down the details allows you to confirm with each boss, every step of the way: “I want to make sure I understand. This is what I’ve written down. Please take a look. Is this your understanding, too?”

Tracking in writing is a very powerful way to create a psychological commitment in both you and your boss to the expectations that you have agreed upon together. You and your boss are also sharing the experience of creating a written record that can be referred to later so you won’t have to wrestle with competing recollections.

Knowing that every expectation is included in a written record creates a lot of pressure on you to live up to the commitments you make. But it also puts important pressure on your boss to make sure that each and every time you are given an assignment, the expectations are spelled out clearly and the performance being tracked in writing consists of concrete actions within your control, not simply a bunch of numbers that are disconnected from the day-to-day expectations spelled out for your performance.

Beyond all that, your written records help you evaluate for yourself, and make the case to your boss, whether or not you deserve any special rewards or detriments due to your performance. Those written records become even more important in the event of a formal dispute because you will have a much easier time confirming, for yourself and your boss, whether or not you are being treated fairly in relation to your performance. If you ever need to get help from someone in HR, you’ll be in a much stronger position if you have kept a detailed contemporaneous record of all of your regular conversations with your boss. That documentation provides a paper trail to support your version of the facts.

Evaluating Performance

Tracking is also the key to taking charge of your own ongoing performance improvement. The constant self-evaluation that comes from tracking your boss’s feedback in writing will help you help your boss revise and adjust your loss prevention strategies.

For example, if your boss says, “You did a great job on A, B, and C, but on D, you failed fully to complete items D3, D4, and D5 on the to-do list,” you will know that your next goal is to focus on D3, D4, and D5. You need to talk through D3, D4, and D5 in detail with your boss right then, noting every single detail about what you will need to do to complete those items. In fact, that would be a good time to make a written step-by-step checklist for yourself for D3, D4, and D5 to use as a guide for completing and quality-checking your work. Later, you can use that same tool as a point of reference to guide your discussion with the boss when the two of you review your performance of D3, D4, and D5.

In order to make sure your performance is accurately and fairly measured, you need to be asking and answering, in ongoing conversations with your boss, the following questions:

  • Did you meet every goal that was set? Did you do all the tasks that you were required to do? Did you go the extra mile?
  • Did you complete the tasks according to the guidelines and specifications provided? Did you follow standard operating procedures? Did you go above and beyond the quality standards?
  • Did you meet the deadlines set in advance? Did you get the work done even faster?

If you have been helping your boss monitor, measure, and document your concrete loss prevention strategies on a regular basis, answering these questions should simply require a cumulative summary of your regular tracking. That is the most important data your boss can ever have about your true performance. Of course, your boss may also have additional data in the form of daily, weekly, quarterly, or annual reports that detail all sorts of performance information—from attendance to hours worked, customer complaints, sales data, and so on. Yes, your boss will use this information, too. The key is to help your boss understand what all those numbers really say about your actual performance; how they are tied…or not tied…to the real, concrete actions within your control.

Together with your boss, spell out expectations for your performance in terms of concrete actions that you can control. Keep track in writing as you complete each to-do item and meet each requirement, as you achieve each goal and beat each deadline. Regularly report to your boss exactly how and when your concrete actions met or exceeded the expectations you set together. Help your boss document exactly how and when your concrete actions met expectations every step of the way.

If you prefer to keep track using electronic tools, all you need is a database and a scheduling program that allows you to create a data record for each boss and/or for each separate work matter. As soon as you receive a new assignment or a change to an existing assignment, enter the information into the electronic record. Create templates for each of your managers, and for ongoing tasks, responsibilities, and projects.

The advantage of electronic tools is that they usually force some logic and organization into your documentation system. Also, your notes are captured digitally and are automatically dated and time-stamped. You can also cut-and-paste key email correspondence, including the back-and-forth messages between you and your boss that help document your performance, and keep that text right in the notes section of the appropriate record in your tracking system.

Whether you use a notebook or an electronic tool, you need to capture certain key pieces of information:

  • Expectations—Goals and requirements that were spelled out; instructions given or to-do lists assigned; standard operating procedures, rules, or guidelines reviewed; deadlines set and timelines established.
  • Concrete actions—Your actual work as you complete each to-do item, achieve each goal, fulfill each requirement, and meet each deadline.
  • Measurements—How your concrete actions are matching up against the expectations. Have you met or exceeded requirements? Did you follow instructions, standard operating procedures, and rules? Did you meet the goals on time?

When you are keeping track, remember that you are creating a contemporaneous record of your work performance. Never write down anything personal about a boss, a coworker, a customer, a vendor, or anyone else. Focus on keeping notes about your work, and your work alone. Use specific, descriptive language, such as, “Followed interviewing guidelines to interview three job applicants,” or “Submitted final report for XYZ project three days before the deadline.” Don’t use vague language or broad

“naming” words like “slow,” “successful,” “good,” “sloppy,” “incomplete,” or “difficult.” Stick to clear descriptions of concrete actions in terms of goals, guidelines, and deadlines.

Frequency of Communication

How often you should engage in conversations with any given manager depends partly on the nature of the work in which you are engaged with each of them. How often you should meet with a particular boss will also be determined by his or her particular style and preferences and also by what works for you. Every situation is different, but most of the time the short answer is that you should be meeting one-on-one with each boss more often than you are currently.

  • If you are working with a boss for the first time, you should meet more often.
  • If you are working with a boss on a new project, you should meet more often.
  • If you are working with a boss on a project with especially high stakes, you should meet more often.
  • If you are working with a boss on a project where there is a lot of uncertainty, then you should meet more often.

The last thing in the world you want to do is make bad use of a boss’s time by meeting more often than necessary or wasting time during those meetings. Keep your management conversations brief, straightforward, and to the point. As long as you conduct these one-on-one conversations regularly, there is no reason they should be long and convoluted. The goal is to make these conversations focused, efficient, brief, and simple. Prepare in advance so that you can move the conversation along swiftly. Once you’ve gotten into a routine with each boss, fifteen minutes every week or every other week should be all you need. Like everything else, it’s a moving target. Over time, you’ll have to gauge how much time you need to spend with each boss.

If things are not going well on a particular assignment consider meeting with your boss every day for a while. Don’t make the mistake of spending hours on tearful inquisitions, indictments, or confessions. Keep these meetings short and consistent. There’s a strong chance that things are not working out because you are not getting enough guidance, direction, and support. Once you spend more time with your boss talking through the work you are doing, you are likely to work through solutions for 99 percent of problems.

If things are going very well with your work, you may only need to meet with your boss every other week. But if you don’t spend at least that much time with that boss, then you don’t actually know whether things are going as well as you think as they are. All you really know is that no problems have come up on your’s or that boss’s radar screen. Spend those fifteen minutes verifying that things are indeed going as well as you think they are. And if in fact they are, then you still need to work with your boss to find out if you can make things go even better.

You’ll be shocked how much you can get done in fifteen minutes. Take any boss you have not spoken with in detail for a while. Spend fifteen minutes asking probing questions about the details of your work, and you will find some surprises. You’ll be darned glad you had that conversation. And you should be in a hurry to have another one.

Don’t forget to consider what day and time is best to meet with each boss. With some managers you may be able to schedule regular meetings at fixed days and times. But if your boss has an irregular schedule, then the best practice is to finish each one-on-one conversation with that boss by scheduling the next one.

Exactly how often, for how long, and when you meet with your boss is likely to be a moving target. You will have to evaluate your situation on an ongoing basis and adjust as necessary. One way or another, however, you can’t wait around to be managed on-the-fly or by special occasion anymore.

This article was first published in 2012 and updated in March 2016.

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