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Working Smoothly with a Virtual Boss

Keith Ferrazzi

Working Smoothly with a Virtual Boss

Learning & Development
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4 minutes
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October 5, 2020

The realities of doing business today often require that employees and their managers work from different locations. When you’re not co-located with your boss — especially if you’re separated by large distances and time zones — a different set of considerations comes into play, as you’ll never casually run into each other in the office hallway or by the water cooler. This was true long before the pandemic set in, and the lessons of the past year remain: You’ve got to change your approach to work with and adapt to the realities of having a virtual boss.

Here’s the good news: As long as you and your boss can develop trust, keep the communication channels open, and establish clear lines of accountability, there’s a good chance that you can work smoothly together. The process can even be extended to whole teams. We’ve collected great stories on remote teams at Go Forward To Work, a community of business leaders committed to gathering best practices during this fundamental shift in the way we do business. According to our research, the following best practices will help you successfully manage the relationship with your virtual boss:

1. Create a virtual contract

First, acknowledge that making your interactions with each other as productive and efficient as possible is going to require a proactive approach. You need to establish the ground rules. How? Start with an email to your boss. Try something like this: “I’ve attached an article that describes how virtual teams can work best together. Can we discuss it in our upcoming call to see if it’s how we want to work together?” What you’re doing is setting up a virtual contract that you can both agree on.

2. Establish rules for communication

People on virtual teams misguidedly assume that connecting more often — via more teleconferences, Zoom sessions, emails and the like — is the answer to the problems of distance. But the result is usually an acute case of screen fatigue and information overload. The real key to managing the relationship with your boss is setting an appropriate cadence of communications so you’re aligned on outcomes. Is it a daily call, or a weekly call? Set the frequency that works best for you and your boss, and have your boss confirm that cadence, keeping these two rules in mind:

  • Specify how quickly you both need to respond to emails and calls
  • Determine what follow-up steps should be taken so you never let important issues slip through the cracks

There are other rules to consider as well. Michael Watkins, professor, author and cofounder of Genesis Advisers, conducted research that found that having regular meetings helped set a rhythm in virtual team work. Here’s what also worked:

  • Sharing meeting agendas ahead of time
  • Starting and finishing meetings on schedule, or permanently baking in a 5-minute delay at the top of the hour for parents with kids at home to get them settled
  • Rotating meeting times so people in different time zones could share the load more fairly

3. Set clear goals and expectations

Think through your personal goals for your work: What would “hitting it out of the park” mean in one month, six months or a year? Spend some time reflecting and write down your performance goals and targets. Then, send them to your boss and have her sign off on them.

Then, in the cadence of meetings that you established in step 2, have frequent discussions with your boss to make sure you’re both checking in on your progress on a regular basis. It’s important to establish clear lines of accountability from the start. This means holding yourself accountable to what you said you’re going to do by when, and getting your boss’s confirmation from the beginning. Let your boss know that you believe feedback along the way is a gift.

4. Get personal

Next, build interpersonal trust. What binds virtual teams of any size together are the personal details — the similarities that lead us to trust the people around us — even when they’re far away. You can do two things to get personal:

  • Send an email to your boss that shares more about who you are. Human beings are social by nature — something that can’t be ignored in your virtual relationship. Use the email to tell them about what gives you energy inside and outside the workplace, your hobbies, etc. Ask your boss to reciprocate. Maybe you’ll find some interest that you could participate in together, such as a nonprofit you could volunteer for, or even a “World of Warcraft” game session to build teamwork and strategy skills in the off-hours.

  • Have regular, personal-professional check-ins at the start of meetings. Take no more than 30 seconds to share what’s going on personally and professionally in your life, including the happy events (e.g., family and career milestones) and challenges you’re facing. Don’t dismiss any opportunities to do check-ins; make them important and don’t be afraid to show some vulnerability: “Hey, let’s do a quick check-in. What’s going on?” This simple storytelling and social bonding builds empathy, trust, and camaraderie.

Research conducted by Northeastern University professors found that many employees working from home felt isolated or disconnected, making it difficult for them to develop personal relationships and trust. The study predated Covid-19 and its attendant health concerns, challenges of parents working from home with children underfoot, or learning remotely under the same roof.  It recommended informal social interactions like the ones described above to increase trust and build stronger connections.

5. Be generous

Go overboard to be of service to your boss. Generosity accelerates emotional bonding because it enables you to selflessly focus on your boss’ success, which strengthens the relationship. Start with acts of generosity that are about doing your job extraordinarily well, and then focus on those that go beyond your job. Concentrate on your boss’ personal and professional goals to deliver against his or her legacy. Finally, “get personal” and do small things that matter to your boss. Each act builds on the one prior. For example:

  • Beat a deadline. (Doing your job extraordinarily well)
  • Ask about skunkworks projects that you could get extra credit for working on. (Going beyond your job)
  • Ask what legacy your boss wants to leave and find a way to help him or her achieve it in some way. (Delivering against legacy)

6. Agree to be candid

Don’t be conflict-avoidant — it’s one of the most destructive attributes of many company cultures. And this is especially true for virtual workers, since you’re missing the regular face-to-face interactions that make it easier to develop strong relationships. Transparency and candor build trust, and should be negotiated in advance, as we said in step 3, when you told your boss that feedback is a gift. Always attack conflicts head-on. Ask for candid feedback from your boss and give feedback to him or her when appropriate. Nip any problem in the bud.

7. Tap into technology

Technology is sometimes labeled as a “distraction” that prevents us from really connecting. But when you’re working virtually, technology brings you together -- especially if everyone is camera-on. Seeing people’s faces during generous moments such as feedback or a personal-professional check-in can only reinforce the good parts of a relationship. Other technologies to consider using include:

  • Communication platforms (such as Slack, Microsoft Teams)
  • Online scheduling tools (like Doodle, Calendly)
  • Cloud storage and file-sharing tools (like Dropbox, Box, Google Drive)
  • Project management tools (like Asana, Airtable, Basecamp, JIRA)
  • Document co-creation tools (like Google Docs, Notion)
  • Virtual wormholes: 24/7, two-way video connections between two locations where “virtual office mates” can see each other continuously

Physical distance is not the death knell to effectively collaborating and forming strong relationships. In fact, it may be irrelevant altogether, because in many organizations where workers are co-located, relationships are often still strained. Why? What’s lacking is not physical closeness, but emotional closeness, clarity, and alignment. That’s why those who work virtually must take a proactive approach to close and overcome strategic and emotional distance. If you truly take these tips to heart, and put clear process and rigor around them, you can have a better, stronger relationship with your boss than the average face-to-face one, regardless of how far apart you work.


Keith Ferrazzi is Founder and Chairman of Ferrazzi Greenlight, which coaches teams and boards on increasing adaptability and collaboration to capture unexpected growth opportunities and avoid unsuspected risk. He is also a bestselling author on the subject of leadership and teams, and his latest book Leading Without Authority was published in May 2020. Go Forward to Work, from Harvard Business Press, is due in Spring 2021.

Learning & Development
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4 minutes
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May 16, 2020