Communication challenges for remote managers and how to overcome them

We’ll add to this list as new comments come in. Some are obvious… Lack of face-to-face interaction with your team or the remote freelancers that you hire leads to communication issues, difficulty detecting burnout, not knowing how to communicate bad news to your team, stumbling upon different time zones management, asynchronous communication, and amorphous lines around hierarchy and decision-makers. But some are… unpredictable. Unseen until you experience it. Or just downright confusing. We’ll cover them all.

Communication is not really harder on remote teams, just different

You could easily argue both sides of a debate about whether or not remote communication is more efficient than working in an office (did you get that memo?), or vice versa. It’s always in the way we deliver it. No one is an expert at this yet, and interpreting text will always be done by humans who are emotional beings.

I started by writing a general “challenges” post and honestly spent so much time on just communication that I figured let’s just start there and keep digging until we hit the bottom.

Not talking enough

With your boss: Somewhere, your CEO read a LinkedIn post that all meetings are bad, and from hence forth all 1:1s with your boss are cancelled. Cool! The reality is, good managers meet with their team.

  • Reality: Unfortunately artificial roadblocks like this one cost more work for you, because you go from being led to being the leader. Lack of communication between leadership then becomes part of your role to solve. It becomes your job to tell your boss when you need their help and how, instead of them offering it and helping you remove other roadblocks. Managing up and down at the same time is exhausting. If your boss is a micromanager already, it will be difficult to shift their energy.

  • Actuality: Face time with your manager is essential because your relationship is based on trust and communication. In the beginning, you lean on them for training, then for projects, then for goals. To hit goals, you must also be able to rely on them for advice, encouragement, mentorship, and guidance. That is the apex steady-state of a senior employee-manager relationship. You can come to them at any time with anything, and they will help guide you.

  • How to solve it: Schedule specific ad hoc check-ins with your boss, even if it’s at the same frequency as your 1:1s were. This keeps your face time on the calendar at the rate you need to be adequately supported. Explain in the meeting agenda (in the calendar invite!) that you need face time to solve this one specific question with their input. In the meeting, make sure you stick to your agenda, explain the situation and ask for their help in how to decide to move forward. If they brainstorm with you, they’ll empathize more with your roadblocks and may offer to help remove them.

With your peers: New ideas seem to pop out of nowhere (but also seem fully fleshed out like people have been talking aobut it for a while but not with you?). Game changing information is shared with a small group instead of the wider teams that could use it. No trust me, we all love discovering major things that the client “already told So-and-so”, on the call, with So-and-so 🤦‍♀️

When DMs are so easy to slide into, how do you prevent side conversations with peers from becoming a game of telephone?

  • Reality: People feel safer sharing ideas in private. Or maybe they want to run it by one specific person first. Or maybe they’re just moving so fast they didn’t take the time to package up the notes and share them. People will naturally brainstorm in smaller groups, and sometimes naturally the conversation evolves into an idea. That idea might be approved by someone’s supervisor and told to run with it.

  • Actuality: When a new project impacts other teams, it can’t be made in a vacuum. Ideas must be brought to light and considered against a roadmap with scored priorities.

  • How to solve it: Be consistent with the rules and apply them to everyone, including yourself. If someone DMs you and you feel it’s an important piece of client info, immediately ask them to re-post it in the proper public channel. If it’s in the notes, ask the person responsible to remember to package them up and send them around.

    • Next, model the behavior you want your employees to show. Summarize the salient points of a meeting, share the notes, and diligently follow up on action steps. The more transparent you are, the more others will follow suit. Summarize thoughts carefully and move them from DM into proper spaces, so people feel like they can still be messy in private but deliver the final message in public.

Your team: In this reverse scenario, your employees are counting on you for training, expectations, coaching, and mentorship, in that order. Reduce frequency, sure, but you can’t cancel your 1:1s entirely just because someone has it dialed.

  • Reality: “10 woopsies wipes out 1 attaboy”, as they say in firefighting. Your employees will remember your criticism 10 times more than your praise.

  • Actuality: Employees will always need guidance, feedback and validation. You can only adequately give it to them if they trust you enough to communicate freely and honestly with you.

  • How to solve it: Keep your 1:1s with your team sacred. Adjust their frequency and cadence with care. Give your employee space to talk and truly listen, not just hear the words and wait to respond. Take the time to brainstorm. And always give positive encouragement.

Talking too much

Too many meetings: “Meeting creep” is a real thing. It’s hard to keep track of everyone and what they’re up to. You’re not going to prevent every useless meeting, but you can set forth principles about meetings and how much is too much.

  • Reality: You can’t control everyone and that’s okay.

  • Actuality: Meetings are necessary but must be worthwhile, even if that time is spent intentionally socializing.

  • How to solve it: In your 1:1s, visit your employee’s calendar on screenshare. Go through the next month and ask about every single meeting on their calendar. If it’s a regular meeting, challenge it. Could it be combined with another? Could the frequency or attendees be changed based on need?

    • Make it clear that you will not allow “I had too many meetings” as an excuse for missing a deadline. Make it extremely clear that it is in the employee’s hands to control how many meetings they accept in lieu of completing deliverables. If their calendar is more than 15% saturated with meetings (30% for managers), it immediately triggers a meeting triage.

On video: Is it… you? Can you hear your own voice for hours? Do you fill awkward silence with the sound of your own vocal chords flapping?

  • Reality: It’s hard to be a manager and read the room on zoom. You feel like you need to fill the void with encouragement and guidance and… I think I’m being repetitive here.

  • Actuality: Silence is powerful and listening is required.

  • How to solve it: Relish the awkward silence. Let 20-30 seconds go by with no noise. Look around and keep smiling, like you’re ready for someone to raise their hand at any time! And eventually, they will. If someone else chimes in, don’t iterrupt. Let it go and let them run with it. You want them to feel like they can be themselves around you and have the confidence to speak up and share without fear.

    • In your 1:1s, just listen. Let 20 minutes go by without saying anything, just nodding. Acknowledge that you hear the person and understand what they are telling you. Don’t solve anything. Just hear them out.

On video: Is it… them? Are you listening intently, the point has been made, but the mic stays in their hand? They just don’t let anyone else in? You’re obviously glancing at your watch on video to indicate, there’s 10 minutes left and this is supposed to be a collaboration, dude.

  • Reality: “that guy” is unfortunately, around.

  • Actuality: There is a professional, amazingly skilled interruptor inside you. Sometimes we have to just interrupt.

  • How to solve it: Trust your gut that you have listened and heard the person. If it feels like it’s someone who’s always the talker, who doesn’t let anyone get a word in edgewise, is first to respond, etc. Wait for them to complete their point and their sentence and then agree with them when they take a breath. When they breathe in, you have an opportunity to enthusiastically put punctuation on their point and then segue into what you need to communicate. “That reminds me that in the next 10 minutes we need to decide…” This strategy pairs well with effective video conferencing tips to manage discussions smoothly.

Being bad at talking (ineffective, inefficient communication)

Not comfortable working in front of you: Slack channel spinoffs are known to multiply like gremlins in water, and soon you’re wondering why #campaign-planning-2 has so much action going on and you weren’t invited.

  • Reality: This is a sign that your team does not feel psychologically safe “getting messy” in front of you. If your team claims the reason for the new channel is to “not bother anyone” then they are not comfortable in public. If people are bothered, they can leave the channel.

  • Actuality: I’m sure you would hate to realize this. But not everyone is going to like you. But, everyone should respect you and trust you if you give them reason to.

  • How to solve it: It’s up to you to create a psychologically safe place for people to work and contribute in public, and part of that is demonstrating consistently that it is safe to do so, by not immediately shooting down ideas or otherwise make people regret speaking up. To keep too many cooks out of the kitchen, decide the smallest group necessary to get all the viewpoints necessary to make a decision. That means you’ll have some channels with 3 people, knocking things out one after another. And some channels might have 30 people all contributing ideas. Either way, clear ownership and everyone practicing good communication etiquette means you won’t have to worry about who is saying what and where.

Adrienne Kmetz

Adrienne’s been remote since 2015. Content marketer for 18 years, Adrienne can’t stop and won’t stop writing. She resides on the western slope of Colorado with her two Catahoulas and loves to ski, hike, and get lost in the desert.

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