Tackling Tough Issues Remotely, When Your Boss is the Problem

We hear a lot about how virtual leaders can deal effectively with workplace conflicts and performance problems. (In fact, many people have written books on the topic, including me!) But we don’t hear nearly as much about how to confront tough issues from the remote worker’s point of view.

And that’s precisely what Sue Shellenbarger, Work and Family columnist for the Wall Street Journal, wanted to know when she contacted me recently for an interview. Since Sue’s questions were so insightful, I have paraphrased three of them here, along with a few replies. Sue’s column is slated to appear in print and online later this month.

What are some of the most common mistakes remote employees make in working with their managers?

Not asking for help soon enough. Unless you admit that you’re behind or need help, your manager may assume you’re doing fine. And why not? It takes a lot of time and energy to detect if someone is in trouble or feels overwhelmed. If you wait too long to admit you need help, by the time you do, you might affect everyone’s deadlines. Far better to call it early and let your manager know what you need to get back on track, whether it’s more time, people to pitch in, or a re-scoping of your work. Be explicit. Your manager is not a mind-reader.

Not establishing a clear delineation about what kind of decisions you can make or actions you can take on your own. You don’t want to go to your manager to get approval for every little thing, but on the other hand, you don’t want to make a decision and then find out that you didn’t have the authority. Talk through different scenarios with your manager to see when you need to consult with him first, and when you can act autonomously. If you worked alongside your boss, you would probably get a sense pretty quickly as to where the lines are drawn. But when you work remotely, these lines of accountability and authority can be very blurry. And they must be made explicit, for both your sakes.

Not understanding each other’s communication preferences. You have a habit of instant messaging your boss every time a question occurs to you, but your boss seems to take forever to respond, even when you’re pretty sure he’s online. Your inbox, on the other hand, rarely gets your attention more than twice a day, which irks your manager, who anxiously awaits your replies. The solution: Talk it through (not via email or IM!) to understand each other’s preferences, and your related rationale so you can create a viable communications plan, which may require a compromise from both of you. But mostly from you.

If you are being micromanaged from afar, how can you discuss this safely with your boss?

First, discover the reasons your boss needs frequent check-ins. Have other team members let her down recently? Does she feel her job is on the line if the team can’t deliver? Maybe you overpromised a few things lately? If your team leader is constantly “checking in,” this is a problem for both of you. A manager who requires frequent assurances that you will deliver on time, may have a hard time really relaxing without constant communications. For you, her “helpful prodding” may feel more like badgering, which makes you feel that she may not trust you. Schedule time for a conversation pronto, before the resentment gets out of hand.

Prepare for the conversation by making detailed notes about the number, frequency and nature of your manager’s inquiries. (Example: “I understand how important this project is, and I know that the team is counting on me to deliver on time. You have sent me an average of two emails each day for the last two weeks, and at least a few daily IMs, offering to help. Each time, I have responded that I am on track as planned and have politely declined your offers to help.”) Also note your track record for delivering projects on time, and your willingness to request help when needed.

Let your manager know how her steady stream of messages affects you and your work. How you say it depends on your relationship. (“I feel like you don’t trust me to keep my word, even though I’ve always come through. Plus, these messages disrupt my work and actually slow it down.”) Then pause for her response. She may be shocked to hear how many times she’s contacted you! Together, create a communications plan so that she can relax in the knowledge that you will come through on time. For example, you might send her an email at the close of business every day to confirm your status, or post your status in the team portal every other day. It may take a few times to get into the right rhythm. Check in with her once in a while and fine-tune if needed.

Your manager has scheduled a 1:1 virtual meeting to discuss “some issues.” How can you prepare yourself for a productive conversation?

First off, ask for a heads-up about what the “issues” are, so both of you can come to the table with relevant facts at your fingertips, thus creating a more level playing field.

Suggest that you set up a video call. Without seeing each other’s facial expressions and body language, you’re both only getting half the story. Make sure you have acoustical privacy when you take the call, and diplomatically suggest that your boss does the same, especially if he works in an office. Have a notepad and pen in front of you to take notes. (Even if you typically take notes via your keyboard, the sound of your key clicking may be taken the wrong way. Plus, the majority of people listen more deeply when they write what they hear, instead of typing.)

Once you have talked through the issues, suggest a few possible solutions to test the waters, and then follow up shortly again after the call, once you have had a chance to think more fully. Before you end the call, set a time for a follow-on conversation, preferably within a week or less. Also suggest other ways you (or he) can check in, if your schedules don’t easily align. If you don’t already meet for regular 1:1 conversations, now’s the time to lock in a regular day and time.

Dealing with tough issues when you work remotely calls for direct conversations that can be difficult even if you’re working face to face. But when you and your manager are not seeing eye to eye, those discussions can be downright scary. That’s when it’s time to grit your teeth and talk things through before small annoyances become big problems for both of you.