Transitioning to remote management, successfully

Overcome these common management obstacles when going fully remote

Elizabeth Tobey,Yellow Squiggle

The changes that swept the workforce during COVID-19 made me challenge everything I’ve learned as a manager. Over the past 11 years, I’ve overseen teams of all sizes around the world, including people with wildly different skills, backgrounds, and career stages. The pandemic gave me a unique opportunity to dispel many tenets of work we used to believe had to exist for success to happen and created a new set of guidelines that is helping me be the best manager.

In early 2020, as offices shuttered worldwide, I oversaw one employee and had two open roles. At the time, my employee lived in a different city than our headquarters and commuted to the office two to three times a week, making our transition to working from home slightly less painful than other businesses. Our company had a flexible work schedule (nearly everyone worked from home on Thursdays pre-pandemic), and some of our key leadership didn’t live in the same city as headquarters. Our parent company was located on the West Coast, and we were in New York City, so we had built a culture where navigating time zones, asynchronous work, and online meetings were the norm.

Despite having Google Suite in place and an active culture that thrived within Zoom and Slack, we still had to figure out how to communicate everything we needed to get done through these channels, which presented new hurdles for each team. I run a Marketing organization, so my challenges are uniquely different from those in Engineering, Design, Product, or Sales. But there are some common obstacles managers have to overcome when going fully remote.

Understand what drives your team

I’ve found the greatest success in managing a diverse workforce by understanding the key drivers of my team. Every manager needs to know not only what their employees’ strengths and weaknesses are, but also what drives them. This is crucial to helping create an environment where someone is high-functioning, happy, and excited to grow and develop within the company.

As a full-time remote manager, finding the time to build up connections and understand motivators became difficult. Conversation through digital means — be it written in a chat client or through a video call — is more a call-and-response interaction than a natural conversation, where body language, intakes of breath, or gestures can convey as much important information as the words being said.

So I decided to model the behavior I wanted to see by connecting with my employee spontaneously throughout the day. When I had an issue I was grappling with and wanted another set of ears and eyes, I reached out to my employee, checked in to see if they were in the middle of something where I would be breaking their flow,  and then quickly spun up a virtual room for us to meet. We didn’t create time-bound interactions, instead keeping that same “quick conversation” atmosphere many of us enjoyed in a collaborative in-person workspace.

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Open a wide window into your life

Work is so much more than the tasks we complete in a day. At the office, we enjoy going to lunch, taking a midday coffee walk, or holing up in a corner for some quiet. We browse the internet or chat with family members when we need a moment of respite. We get up and talk to colleagues about TV, sports, and trips.

I gave my team insight into my life to encourage them to openly discuss what was going on in their lives if they felt comfortable. The spaces between our meetings and projects and how we fill them are just as vital to the company’s success as the milestones, reviews, and reports.

Working remotely, for many, meant opening a wide window into our homes, something that can be daunting, and cause people to feel vulnerable. To make my team feel more at ease, I celebrated the benefits of working from home. I’m an avid bike rider, and I was open with my team when I took an hour in the middle of the day to complete my workout, something I could never have done from an office. I posted in our public channels when I had to dash out for an errand or walk my dog, and I let people know that my camera was off during our 12:30pm syncs when I was making my lunch.

“I think this strategy [of working in ways and at times that made people most productive and comfortable] is a large reason why we did not see a drastic hit to employee morale or productivity over the past year, and why our company steadily grew revenue and profit.” — Elizabeth Tobey

By normalizing that behavior, and inviting people to share as much or as little as they wanted, I aimed to remove any stress or fear related to enjoying the advantages that come with working at home. I wanted people to be able to work in ways and at times that made them most productive and comfortable. I think this strategy is a large reason why we did not see a drastic hit to employee morale or productivity over the past year, and why our company steadily grew revenue and profit.

Rethink the hiring process

I also had to take on an entirely new strategy for hiring. It had become clear that we could thrive as a fully remote company, so I permanently removed the requirement that everyone had to be in our office. I went through the same process of forming a hiring committee, and used the same methodology to form criteria for hiring candidates. However, I adapted the questions and interviews to suit a virtual meeting, making interviews 30-45 minutes with no more than two, and preferably one, interviewers with the candidate at a time.

When it came time to make offers, I went into great detail about expectations of the role as a remote employee, how our company functions, and its key selling points in this remote environment, while also explaining what we did before (and would likely do again) when folks came back to the office. That way, I was able to help employees feel confident that they would work well in the current environment and be happy in the future one.

This was important for both candidates, one of whom would be returning to the office, if she so chose, in the future. I wanted her to have an office environment that worked for her. For my other candidate, I wanted her to understand what would and would not change about her remote experience when others returned to the office, so she would still be able to thrive and work efficiently in that future environment.

Reduce anxiety through the onboarding process

Finally, I created an entirely new process for us to onboard employees and worked with others on the leadership team to roll it out to managers.

The onboarding process my team goes through takes three weeks. The first week is entirely about meeting folks and getting a lay of the land. The second week is guided by me, and sets up a second round of meetings to dive deeper into specifics and answer questions that came up in week one, and only in the third week do we start to build a plan for getting started on the role itself. This also sets expectations that the first quarter is about learning, making connections, conducting audits, and assessing current workflows or preparing proposals for programs that do not yet exist.

This new onboarding process included a comprehensive document with the information necessary to get started with our tools and systems to help new hires understand the business and the company’s history, objectives, and core projects. We also made sure to get employees the equipment they needed ahead of their first day, so they had time to set up before the first morning they were expected to log in. We also built out blocks of time for training and socializing, along with a healthy dose of time for new employees to read, set up technology, or otherwise decompress.

In a remote environment, it is not essential to deliver anything tangible or actionable immediately in order for me, as a manager, to determine if a new employee is being productive. I wanted to remove the anxiety caused by not physically seeing my new employee; I didn’t want to assume that without emails or documents, they were doing nothing. So I reinforced the idea that onboarding time was for learning by having check-ins multiple times a week to discuss how things were going, and I asked my new employees what they were finding most interesting and challenging each day. By being proactive in getting face time with new hires, I hoped to remove the fear that they thought I had more stringent expectations than I did.

Hiring is not a short-term gain — to develop an excellent employee, you have to allow them to settle in first, train them, and through the onboarding process, build trust.

Looking ahead

Fifteen months after we became a fully remote company, we’re still not back in the office, and we don’t have plans for when we will officially open it. I’m sure we will, eventually, but I do not intend to ever mandate that anyone will have to go into the office. Likewise, I don’t expect to artificially limit my talent pool again by mandating that candidates are within commuting distance to an office. I will transition back to being an in-person manager sometime in the next year, but I want that new definition to not require that I, or any of my employees, have to be seated in the same location to ensure the success of our team.

2020 showed us that valuable employees can adapt to anything if you treat them with respect, and work with them to provide the tools and processes they need for success. The most successful companies do not need in-person collaboration in an open office, around a water cooler, or in conference rooms. The best ideas do not happen only serendipitously because we are in the same location at the same time we are puzzling out the answer to a problem. And, equally important, it’s crucial to know that some people do prefer an office setting, and will always do better face-to-face, or around a table instead of on a screen, and that adapting work to the team you have is always the best way to succeed.

Adaptive tools, processes, and structure is essential to your team’s success, and it is imperative that managers create the culture they want to see by living it first.

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Fully remote? Here’s how to successfully transition to remote management
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