Remote Team Challenges and the Stories We Make Up

“I used to have great relationships with my team before we went remote.”

– Many executives I coach.

I’ve heard this line from multiple senior-level executives struggling to connect with their teams. Their direct reports have also reported that they feel micro-managed and suffocated.

In a high-stakes business, with little margin for error, relationships are further strained by virtual work settings. Small talk is awkward at the top of a call and there is no “water cooler” to make everyone feel anchored to a space. There are no chances for an impromptu lunch. The thought of a virtual coffee sounds like a drag to most.  

So what happens? In the absence of those important in-office connections, we invent stories about each other to fill in the contextual gaps that are normally addressed when we have in-person social exchanges. So, what can we do? 

We don’t need to throw virtual happy hour parties to connect with your team (but if you do, please feel free to invite me!). More importantly, we must slow down and connect with an empathetic, curious mindset in order to gain efficiency and productivity. This is a daily practice. 

Below is a list of scenarios I’ve witnessed on teams, where people’s assumptions have created unnecessary friction and even compromised trust. I’ve included some NEW approaches to these situations that are rooted in empathy, vulnerability, and curiosity. 

Scenario 1: You see an “away” bubble on your direct report’s Slack.

Thought response: They must be taking a two-hour trip to the gym again. 

Reality: They decided to do focus work in lieu of responding to slack. 

NEW Curiosity-based Approach:  “I noticed you are off Slack a good portion of the day. When do you focus best, and what are the best times for you to be available to the team on Slack?” (This is assuming that the person is getting their work done.)

We make up stories about a colleague’s mood…

Scenario 2: Your manager shows up to a virtual meeting late and looks frustrated. 

Thought response: I must have done something wrong. 

Reality: In the office, you might have learned that an account fell through, and therefore understood the context behind that bad mood. 
NEW Empathy-based Approach:  “I could be wrong, but I’m noticing you seem a bit (frustrated), is there anything I can do to help? Is this still a good time to meet?”

We make up stories based on how vocal people are in a Zoom meeting…

Scenario 3: Team member does not contribute to a virtual brainstorm. 

Thought response: They are disengaged, surfing the web, or absent of ideas. 

Reality: This introverted person prefers to socialize his ideas quietly with one or two people before announcing them on a call. 

NEW Curiosity-based Approach: “I’m sensing holdback from you in our group brainstorms. How do you feel most comfortable sharing your ideas?”

We make up stories based on the perceived tone of an email…

Scenario 4: Your boss sends you back a deck with revisions and edits, but with little commentary. 

Thought Response: All you see is red ink, and you feel triggered and deflated. The tone feels cold. You think, “Why bother? They will change it anyway.” 

Reality: Your busy boss is moving too quickly and sees a meeting to explain edits as inefficient. 

NEW Vulnerability-based Approach: “I know it’s more efficient to for you to send me your revisions, but I’d love to learn your thoughts behind them so that I can make it better next time. Could we review it together on a call?”

We will continue to misread each other’s feelings if we don’t STOP making up stories and START using some vulnerability, curiosity, and empathy to gain clarity.

I’ll paraphrase what I just wrote: STOP making up stories and START getting curious.

 (And if you are going to make up a story, create one that evokes empathy in your heart.)

While fast meetings seem helpful in a busy calendar, we will pay for it by creating a team that is disengaged and dissatisfied. So you want success? Don’t be “all business.” Be “all human.”  It’s really that simple. 

To learn more about building success with empathy in a virtual office, contact me at

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I’m Cassidy Nasello.

I was once driven by stress, fear, shame, jealousy, self-doubt, and perfectionism – until I learned to recognize and combat my self-sabotaging talk. I bravely honored my inner truth and quickly saw that I could serve others as I served myself. My focus is strong and purposeful now. I want for you what I claimed for myself.

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