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5 Things I Learned in my 365 Days as a Remote Leader

For many people outside of the tech industry, remote working was an entirely new concept. I think it’s safe to say that it was a little easier for those of us lucky enough to work at Slack, a workplace messaging app that was redesigning virtual productivity even before any. this pandemic is not starting.

Having said that: there is a big difference between switch to telecommuting and joining a remote team for the first time.

5 things I learned in my 365 days as a remote manager

When I arrived at Slack in June of last year, I became part of a 35-person team made up of people I had never met before, not just one. I not only had to find a way to get to know everyone (which is hard enough as it is) but also to gain their confidence as a leader.

Now, a year later, I think about the tools, tips and philosophies that have made remote leadership not only possible but also fun.

At the end of the day, it’s about being “gracious” within the limits that have been placed on us. We can deploy the quality of “graceful” while embracing the new tools and technologies that have emerged along the way.

Here are five things I learned:

Don’t let productivity get in the way of team development

I had no idea how much I relied on sweet meetings – in the elevator, casually at someone’s desk, etc., to build the basic confidence needed to function as a real team. During the pandemic, the loss of those “water cooler” moments was seen as a sad but necessary sacrifice to keep people safe.

In the post-COVID world, the hybrid workplace is here to stay. This means that it’s up to us, as leaders, to make room in our messages for these natural moments to occur. If an informal conversation emerges during a structured period, so be it.

When hosting a meeting, know that it’s okay to let some of the more social conversations unfold. It is normal that you are not so productive. What you do is get to know your team, and maybe more importantly, get them to know you as well.

Remember: you can always schedule another meeting to discuss things that you haven’t reached.

Embrace the great “leveling effect” of remote working

In my last role at Boomi, my engineering group was based in Pennsylvania while the engineering group was based in San Francisco. Whenever I had a meeting with engineering, I would zoom in on a meeting that was taking place in San Francisco, where everyone was together.

Once we all started working remotely, it felt like the playing field had been leveled. We all face the same frustrations and complications, and for the most part, we all use the same technology to overcome them. This means that no matter where we are or what position someone is in, they have the same ability to connect to the conversation as anyone else.

This equal opportunity is one of those things we will need to pay attention to in the post-COVID work environment. As some workers remain distant while others return to the office, it is essential that we protect this level approach where everyone has an equal chance to participate in the conversation.

Integrate social

Believe it or not, the remote nature of our work in 2021 has led to the creation of a number of tools that make it even more Easier develop team bonds.

Slack apps like Donut gave me a way to engage the team on a daily basis, without them feeling too forced. I’m a huge fan of the chat prompts in our Team Slack channel that we get at the start of the day. My team seems happy to be committing to something that is both lightweight and directly integrated into their digital workspace.

Automate the important

Whether your team is remote or not, there are daily (dare I say tedious) tasks that cannot be overlooked no matter what is going on in my day.

Workflow generator

Whether it’s letting a new employee know about an existing project, or even just presenting it to the rest of the team, it’s critical that these messages get out quickly.

Using Workflow Builder has made it possible to automate all of our most important “maintenance” tasks. Automation tasks mean everything from onboarding and training to vacation requests.

Workflow Builder is about getting information where it needs to be when it needs to be there.

As an added bonus, Workflow Builder’s visual interface is a snap. Any team member can create a personalized workflow in minutes, no coding required.

Steps from apps to Google Sheets

Be gracious with your expectations

We have to remember that when it comes to the concept of “job performance”, there really is no benchmark for things like this. To say that last year was not easy is an understatement. Our employees have had to deal with spouses who lost their jobs, loved ones fell ill, and people across the country struggled financially.

It is almost impossible to discern what “high performance” means even today.

From a leadership perspective, the invisible stressors associated with a global health crisis are difficult to detect and even harder to involve.

This is where personal connection becomes really valuable.

If you’ve made the effort to get to know your people and given them the opportunity to get to know you, it’s much easier to share the things we struggle with and act with compassion. Because at the end of the day I’m a human being too, and it helps a lot when that compassion goes both ways.

steve wood Remote work

Steve Wood

Vice President, Development Platform


Steve Wood is the Vice President of Developer Platform at Slack. Steve is the driving force behind the continued success of the Slack platform, which offers integrations with over 2,400 business software tools. Previously, Steve was Chief Product Officer of Dell Boomi, where he led the company’s cloud and low-code development tools. He is also a co-founder of two cloud-based platforms, ManyWho and Informavores, which were acquired by Dell and Salesforce, respectively.



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