Leadership for the Virtual Office

Photo of woman on laptop and checking her phone

By Charles Meyer, Internal Consultant, Office of Strategic Consulting. In previous roles, Charles supervised telecommuters in multiple time zones for 10 years while leading the National Center for Media Engagement and a subsequent initiative to support veterans reintegrating into civilian life.

Supervising employees who are telecommuting brings unique challenges. Below are some lessons I learned while supervising telecommuters and leading teams with telecommuters through uncertain times.

1. Share frequently with your team.

During uncertain times, people crave information—and when they don’t get information, they start imagining the worst. Share what you know and are at liberty to share as often as you can. Acknowledge what you don’t know and resist the temptation to speculate. Even communicating “I have no updates for you since our last conversation” can be reassuring to stressed employees.

Tips for Information Sharing:
    • Let your team know where and when you’ll be connecting (e.g., via text, instant messaging, email, etc.).
    • Send a regular update to the entire team.
    • If you receive the same question from multiple people, create an FAQ or respond to these questions in your updates.
    • Don’t assume everyone reads campus-wide updates. If something important comes out from an executive, include a brief notice of it and link to the source. Avoid trying to restate, interpret, or summarize key communications from other offices.

2. Be clear about expectations.

When circumstances and contexts change, people can get discombobulated. Do all the same rules apply? Are staff supposed to email you if they are “out of the office” for some reason, or is instant messaging okay? Are staff expected to keep their instant message status updated? Aside from the change in physical location, is it business as usual? Are their work priorities the same, or are they supposed to pause some activities and prioritize new ones? Be as clear as you can, and if things are going to be in flux, say so. Above all, encourage everyone to keep doing good work under the circumstances.

Tips for Clarifying Expectations:
    • Let people know what won’t be changing.

Example: Our office uses Box for file sharing. As we moved to telecommuting, several people began putting files in Microsoft Teams instead, causing some confusion about where to find things. A quick reminder that Box is still our primary file storage solution helped.

    • Set expectations about what information they should share with you (and with each other).

Example: If the team is highly collaborative, it is helpful for everyone to know who is “in the office” and who is out. We use Outlook calendars for this information, and the expectation is that everyone continue to update their status in their calendars.


3. Be understanding.

Keep in mind that people are different, and they respond to change and crisis differently: some people freeze, others feel overwhelmed, still others take control and start doing things—even if maybe they shouldn’t. To the extent you can, engage your team in a conversation that acknowledges the situation for what it is and that lets them know it’s okay to feel whatever they’re feeling—what matters is how they respond.

Tips for Being Understanding:
    • Unless someone on your team is absolutely essential to the campus operations, if they ask for time off, grant it without question.
    • Check in at the beginning of every team meeting. Instead of asking “how is everyone doing?” ask each person individually how they are doing.
    • Take a one-question poll to gauge how everyone is doing. Let them see the results, so they can see that others are experiencing similar feelings.
    • Devote some time in team meetings to suggestions for coping, wellness tips, etc.
    • Pay explicit attention to wellness initiatives.
    • Take a deep breath before reacting to something you don’t like.

4. Connect, connect, connect.

Though we have numerous communication tools, people who are telecommuting can easily start to feel disconnected and isolated. It becomes tempting to imagine that everyone else has information they don’t or that others are convening virtual meetings or chats to which they are not invited. It’s not rational, but that’s not the point. Go out of your way to include everyone and to make it an expectation that others will be included as needed.

Tips for Connecting:
    • Check in on team chats and instant messages and see if all team members are involved. If someone is noticeably absent, connect with them immediately to see how they are doing.
    • Schedule the kinds of informal get-togethers that were happening in physical space.

Example: Everyday, anyone on our staff who was available would break for lunch around 11:30 in the breakroom. We now schedule “virtual breakroom” lunches via video. It helps to interrupt the solitude and monotony (especially challenging for those who live alone).


5. Use instant messaging to replicate casual hallway or breakroom conversations.

Check in with your team members casually even more than you normally would. Send an instant message to just say “hey, how was your weekend” or “how are you doing.” Casual check-ins go a long way toward continuing the rapport that normally happens in the hallways or breakroom. It helps everyone feel connected to each other.

Tips for “Hallway Conversations”:
    • If your usual practice was to stop in and greet others on the way to your office each morning, continue this practice in virtual space.
    • If you think of someone and want to check in personally, send a message while you are thinking of them.
    • If a topic comes up in email that sparks a conversation, ask the person to step into a quick video chat or just call them on the phone.
    • If you are chatting with one person and want to ask another to join you, do so—conference them in, invite them to the chat, or ask them to join a meeting in progress.

6. Use video for one-on-one meetings.

Instant messaging and email are great, but a video chat helps gauge someone’s body language and demeanor and can quickly give you a sense of how they might be doing. Non-verbal cues are especially helpful for high-context individuals, and seeing faces can help everyone connect more meaningfully.

Tips for Using Video for One-on-One Meetings:
    • Ask your direct report to tell you about their work space; let them know you are aware of their surroundings. Ask them how it’s working for them.
    • Ask them to list their current tasks or projects and share the screen with you. Together, work through the list and discuss what needs to be reprioritized given changed conditions.
    • If you see or hear background “noise” (a cat meowing, a baby crying, a partner wandering through the room), laugh with them. Acknowledge their situation and their lives; reduce stress about this sort of thing.

7. Stay positive, and assume positive intent.

Supervisors can feel disconnected, too. When you haven’t heard much from an employee, resist the temptation to assume the employee is being unproductive. Casting yourself in the role of productivity cop is not likely to go well for anybody. Embrace your role by creating the conditions for your team to be successful.

Tips for Staying Positive:
    • Reach out and connect with team members. Ask what, if anything, they might need from you or others.
    • Show that you care.

8. Focus on the work and outcomes more than on the clock.

In the office, it’s easy to see if someone is “in” but has just stepped away from the empty chair. Keep in mind that telecommuters do all the same physical things that people in the office do: they step away to grab food, use the restroom, stretch their legs, or get some air. And, recognize that some employees are juggling multi-person households that might include more than one adult working from home or a college or K-12 student engaging in online learning. As a supervisor, resist the temptation to assume that a slow response means someone is watching Netflix. They might just be fixing lunch—or absorbed in their work! As long as the work is getting done, be flexible about exactly when or how it’s happening.

Tips for Focusing on the Work:
    • Don’t assume that anyone is available at every minute of the day.
    • If you need something urgently, or by a certain deadline, let them know what the deadline is and trust that you will get what you need when you need it.
    • Check in to see how people are and what they need, but don’t micromanage their work. Check in on work progress only if this was part of your usual routine (and you need a status report).

9. Take care of yourself.

Your whole work life has been disrupted, too. As you think about how to help your team succeed under new conditions, take stock of what you need. Your supervisor may or may not be following the guidance outlined above—and that’s okay (they may be overwhelmed, in crisis mode, or otherwise preoccupied). If this is the case, use the guidance above to help you craft questions that you can ask of your supervisor—and then ask! Remember to “put your oxygen mask on first.” If you aren’t taking care of your own needs, you can’t look after those of others.


Other Tips?

We, too, are learning as we go. If you have comments, suggestions, or other best practices that have helped you, please share them in the comment box below.

2 thoughts on “Leadership for the Virtual Office”

  1. Work at home is exposing / exacerbating weaknesses in our internal collaboration. Where before we might not communicate well with one another, now it is really important to work together better. Some are resisting efforts to better work together and self-isolating (for instance, don’ t want to share calendar or use new software) while others are exploring all the options to improve connectivity. The uncertainty is challenging for people too – not knowing how long we will be working from home, whether or when travel will be feasible or conferences a way to accomplish our work.

    1. Michelle, thank you for highlighting one of the challenges of working remotely as a team. While there are certainly valid reasons for some people’s resistance to sharing their calendar (e.g., perhaps their actual “work time” now varies by the day due to balancing the needs of others at home), or using new software (e.g., having to ramp up technological expertise quickly can be overwhelming), there is also an increased need for staff flexibility in staying connected and collaborating. The Office of Strategic Consulting has expert facilitators on staff who can work with your team to identify people’s concerns and come up with strategies to address them. Please email us at strategicconsulting@osc.wisc.edu if you’d like to discuss this possibility further.

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