Secret to Managing a Remote Team for the First Time- Stay S.T.E.A.D.Y

It is easy to work remotely when you’re an individual contributor, responsible for your personal deliverables. It is like being the superhero in a movie where you save the day at the last moment just as the deadline is about to kill you. 

Things get more complicated when you start to manage a team. That is when you realize it is tough being Nick Fury trying to assemble and manage the superhero team of Avengers. 

The bigger challenge arises when the only time you can meet your team is on Google Meet. It is easy to discuss things on top of your head with your team when they are next to you. Else, you have an additional cognitive load of looking through the calendar, scheduling an invite, and getting ready for the Meet fatigue. 

I faced a similar challenge last year. It was the middle of the pandemic when I joined an eCommerce startup as a content manager. It was the first time I was officially responsible for managing a team.

Over the past 1 year, we have gone from a team of 2 to a team of 8. 

I have not met or seen any team members in person so far. Yet we have been surprisingly productive and built a strong internal team culture.

We love the work we do (most of the time! :D) with each other. Everyone is responsible, not only for their own deliverables but also to support the other team members as and when required.

It did not happen overnight, though. It was a steady process to come to this scale and speed. In retrospect, there were few key areas where I tried to focus actively to try to build and scale this team from 2 to 8.

I call this a S.T.E.A.D.Y framework to manage a remote team as a first-time manager.

1. Systems

You cannot scale the operations of any business without well-defined systems and procedures. This becomes critical in the creative team of a startup as well where you have to balance quality and speed. 

Initially, when we were just 2-3 people, we did not feel the need for a proper system to track our day-to-day work. However, as the number of requirements increased and the company grew, it became difficult to operate without being on constant calls to manage teamwork. 

This is where I first implemented a project management system using Asana. It was a simple team dashboard to have one view of all deliverables and tasks our team was doing. 

As a manager, this gave me a holistic perspective of team bandwidth and priorities at any given point in time. Initially, we were only 3 people using it so the effect was hardly incremental. 

However, I realized its impact only when we were 5-6. I had the whole visibility required to make decisions about our team priorities and timelines while planning with the other stakeholders in the organization.

The system has grown more sophisticated with time as I started using Zapier to connect Gmail, Google Sheets for automatic task allocation and even measure our approximate team bandwidth to take hiring decisions using Asana. 

However, it was the simplicity of the system for 2 people that allowed it to scale with the number of people in it.

2. Trust

I have had a terrible experience in one of my past companies. We had started remote work there long before the pandemic had kicked in. 

At one point, they mandated that we install software that tracked our computer screen and gave us alerts if we were sitting idle for more than 10 minutes.

I hated it. As someone who always gave his best and went beyond my role to get any work done, that decision shattered my dedication and respect for them.

Clearly, there was no trust. 

Based on this experience, I had vowed that if I ever led my own team, I’d trust my team to get the work done, not on how much time they spent on the laptop. 

Most of the people in the team are in their first or second jobs. That has never prevented me from giving them complete control over their work after the briefing and strategic guidance. 

The system set on Asana helps in the complete transparency of team tasks and empowers everyone to define their tasks based on their deliverables. This transparency and accountability in turn further helps in establishing trust within the team as there is no micromanagement required to get anything done.

I rarely need to call or follow up with any of them for any work they know they have to do. Of course, there is feedback involved but not on their time spent on the laptop.

3. Empathy- Practice empathy and kindness more often

In remote work, it is easy to forget and miss the personal circumstances of an individual. You never know what a person might be going through at their home as the boundaries between work and life can get blurred at times. 

At the time of the second wave in India in April-May, most of the team members were going through tough times. Sometimes it was due to COVID at home. Sometimes it was just the additional anxiety that comes in when all you hear throughout the day is the sound of ambulance sirens.

The most important thing one could do is to be extra kind and empathetic in the situation. It can be in the form of just weekly, personal check-ins beyond work to ask how they are doing or simply offering to help in work wherever you can. Communication plays a key role in such situations and if you’ve built mutual trust within the team, it gets easy to talk to each other beyond work.

The biggest thing with empathy and kindness is that most people see and acknowledge this in return. There was a time during a late evening meeting when an urgent requirement came up for a marketing email. I was already swamped with other things but at that time had no other option as it was a critical task. One of my team members rose to the occasion without me asking and volunteered to do it as he was already done with his work for the day. 

It is a huge thing to realize as a first-time manager that the team has got my back even when I falter at times (which I sometimes do). Mutual trust and empathy have made this possible for this level of understanding.

4. Action- Lead by action

The biggest fear I had while starting out as a manager was losing complete touch with the on-ground execution. I was scared of being the manager who just tells people what to do but has little or no skill to do it independently.

This is where I consciously made the call to spend at least 20-40% of my time doing things myself even if I could have delegated those things. 

For instance, I make sure that I still write content for at least 2 weekly email campaigns. It does not mean I am insecure about my place or skills within the team. It is more like I want to stay in touch with the ground reality and not forget the time and energy required to ship writing at scale.

In retrospect, this practice has helped me become even more empathetic and understanding of the team. At times, it has also helped me to push them extra to consistently raise the bar of speed and quality by sharing my own experiences, insights, and thought process to do things in a better and faster way. 

I think this is what they call leading by action and that is where I aspire to do in the future as well. 

Of course, I realize that as a growing manager and leader, there would be a time where I might not be able to do things on my own while juggling strategic meetings and setting overall direction to orchestrate the entire content engine. But you cannot make critical strategic decisions if you’re not in touch with the ground reality. In remote work, it is even easier to lose touch because you do not get to see or talk to people.

But this mindset of leading by action has helped in building and scaling a good team from scratch while setting examples.

5. Document everything

I have worked with almost 4 companies to date in India. I am yet to see active writing or documentation culture.

As an individual contributor, I never felt the need because I knew what I was doing. But I realized the true value of documentation during my time as a manager. 

It happened for the first time while setting up Asana. There were so many things in my head where I envisioned its right application for our context. It was easy in the beginning to explain them over a demo to the team. But it used to take an extra 1-2 hours every time a new person joined the team to explain the whole process. 

That is when I spent an extra 5-7 hours summarizing my approach to setting the system and giving step-by-step directions on how to use it. Not only my team but the company recognized the value of such a document. 

This is when I began documenting more actively- team manifesto (detailing team structure, responsibilities, challenges), templates, SOPs, and more recently, meeting notes. 

Now, every time someone requests a quick download of a meeting or what to do next, I just send them a one-pager or meeting memo to give the entire context rather than simply telling them what to do.

While going through the Write of Passage (an online course by David Perell), I got a chance to attend a workshop by Brie Wolfson. She talked about the culture of documentation and writing at Stripe and how it leads to structural and content transparency. (you can read the entire piece here)

I could relate to many things she said to my personal experience of limited documentation so far. I have already experienced the benefits of putting meeting agendas in writing in advance, SOPs, meeting notes, and guides like Asana walkthroughs. This has helped the team, especially the new members, get a super-fast understanding of how we do things on a day-to-day level.

Honestly, I regret not doing this very early in the job and only tried to do it 4 months after starting. Better late than never!

6. Yearning for Belonging- Acknowledge It

This is the trickiest part of the STEADY framework which I still struggle with. While remote work definitely has its advantages, it is tough to create a sense of belonging within the team when you screen apart.

But what is the meaning of belonging? I first came across the term when I read the book, Braving the Wilderness by Brené Brown. Belonging is the innate human need to belong to a tribe. In prehistoric times, banishment from the tribe meant death. While this might not be true in the present world, we still crave the feeling. 

Brené Brown says that this yearning for belonging is “so primal, we often try to acquire it by fitting in and by seeking approval”. This is a paradox that one cannot feel a sense of belonging until one is courageous enough to be themselves.

“Because true belonging only happens when we present our authentic, imperfect selves to the world, our sense of belonging can never be greater than our level of self-acceptance.”

Brené Brown, Braving the Wilderness

In a remote team, how does one acknowledge this yearning and build a culture where everyone can feel comfortable and courageous to be themselves? How do you enable individuals to be their authentic selves? 

Honestly, I do not have the right answer yet. But there are a few things I have learned along the way when I started doing this 2 – 3 month back. 

One thing is sharing bits from your personal life (whatever is comfortable) with your team in casual conversations beyond work. It can be sharing your creative projects, chatting about the book you’re reading, things you’re passionate about, or even just sharing how Monday blues are affecting you! 

I usually have these conversations in one-to-one 20 min slots with each team member, preferably on a Thursday or Friday. In these calls, we just chit-chat about the week gone by, major challenges, and any other things going in our lives.

It also counts when you can openly accept mistakes and share your struggles with a particular project or even personal challenges. It encourages others to do the same and helps them realize they are not alone.

It can be difficult to have these conversations in the beginning when you’re used to talking about work and productivity only. It is also possible you won’t be able to have these conversations with everyone. 

But it is essential in the long-term to create this level of comfort to acknowledge and respect this yearning for belonging within the team.

This is also where the trust you build within the team and the empathy you have for others will come into the picture. Without mutual trust, respect, and understanding for one another, you cannot create a sense of belonging. 

Path to a STEADY Manager

The biggest thing one can learn as a manager is to keep one’s calm and be steady when the boat is rocking with waves of endless work. The STEADY framework puts together tangible and intangible aspects of leading and managing a productive and effective team. 

  • Systems
  • Trust
  • Empathy
  • Action
  • Documentation
  • Yearning for Belonging

Together, the three things- building trust, practicing empathy, acknowledging and cultivating the yearning for belonging– form the non-tangible aspects of remote team building and management. 

Combined with the more tangible or practical aspectssetting simple systems, leading by action, and documenting everything- you have got a STEADY framework to build and manage a remote team as a first-time manager!

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