What Your Boss Needs to Understand About Working Remotely

05/07/2020 Posted by Jeremy

The novelty has worn off. The honeymoon is over. Zoom fatigue has set in. Just as weeks spent cooped up with significant others have necessitated relationship adjustments, it’s now time for an intervention with your boss.

How to Transcend the Flaws of Time and Space

I get it. Before joining the good folks at Knack, I worked at several companies who were terrible at Work From Home. Some specifically prohibited it as contrary to their culture. Another was forced to allow it to avoid attrition among key employees. And others pretended to embrace it but didn’t optimize for it.

The New Normal

Now that COVID-19 has forced everyone into the largest Work From Home experiment ever, misgivings have given way to reality. Even so, many companies view the experiment as merely something to endure before things go back to normal. Those fixated on the past are failing to see—or benefit from—the massive shift to remote work that will last long after COVID-19 fades.

If your company is new to remote work, it’s tempting to force staff into the same cadences that you had when you were all working in the same office. The same weekly meetings and morning standups, now in Zoom. But while this may seem like a way to maintain a sense of normalcy amidst the sudden demands of social distancing, it represents a failure to understand both the challenges and opportunities of the new normal of remote work.

The challenges can be obvious. Everyone has a life outside of work, and those lives can be messy. Childcare, errands and household duties can sometimes interrupt even when we work in an office. Once everyone’s at home all the time, those demands can be even more pressing.


Image courtesy of BBC

Of course, this can be frustrating for managers who are new to remote work. How are you supposed to get your employees on the same page at the same time?How can you be sure they’re working if you don’t enforce the time they’re online?

Part of the opportunity of remote work is that sometimes it’s better not to worry so much about time.

Knack has been exclusively Work From Home since its inception. We don’t even have an office. No white boards. No watercooler. 100% remote. We value relentless learning and are always questioning the status quo, so we are continuously optimizing how we work remotely. And while we don’t yet have it all figured out, we have been able to learn a few things along the way.

One key lesson? For employees to be productive wherever, you need to allow them to be productive whenever. Flexibility in space demands flexibility in time.

It’s also important to clearly define what productivity means to you. Is it time spent in front of a keyboard, or successful outcomes to projects or company objectives? At Knack, we cultivate a culture of trust, and expect our teammates to tackle what needs to be done (within reason) to drive outcomes, regardless of specific times online.

Collaboration Across Time and Space

Even though I had worked remotely before (from an island in Alaska, no less), starting at Knack was a bit of a shock. I tried to schedule lots of Zoom meetings and presentations to foster collaboration (and to prove I was doing stuff, if I’m honest) like I had at previous companies. While my new teammates were happy to jump on video calls to meet the smiling new guy, they patiently nudged me towards a better way.

Knack’s employees are spread across multiple time zones. I’m in Alaska time, which most people don’t even know exists. I’m currently awake at 3 AM because it’s light outside, because Alaska. The only other teammate currently online lives on a ridiculously idyllic farm in Portugal. (Hi, Robert!) Everyone else will be in and out through the day, but our team can somehow collaborate more efficiently and iterate more quickly than many in-office teams.

How? By embracing the asynchronous.

Robert Sleeping

Robert demonstrating the effects of time zones at a recent retreat.

Instead of always scheduling endless meetings to understand challenges, plan a project and assign tasks, Knack uses a variety of tools to let us accomplish the same things in a way that works for the varying schedules of our distributed workforce.

Living Discussion Docs

For in-depth discussions, we use Google Drive, Coda, and other platforms to foster asynchronous feedback. Regardless of the tool, a commonality is that they allow commenting and content collaboration by multiple users.

With traditional meetings, someone needs to set an agenda, get everyone together at the same time, take notes, and jot down action items. With asynchronous collaboration via discussion docs, all of those outputs happen automatically, but at varying times that work for everyone. And you’ll never find yourself trying to remember what someone said in a past meeting. Why? Because the doc is the meeting.

In our case, a Knacklehead will typically post a discussion doc with a rough outline or text, then share it with the relevant teams for feedback. It can be tempting to try to get the initial discussion doc as far along as possible before sharing, but we find it best to request feedback early and often. This allows us to iterate much more quickly, and perform course corrections before work is wasted heading in the wrong direction.

Feedback requests work best when they define the scope of input needed, a deadline, and potential blockers that the team needs to be aware of.


From Collaboration to Execution

Ultimately, our project discussion docs can result in a new process or workflow. Once that happens, we often leverage the same platform that our customers do.

We use Knack to keep our data in one place and accessible everywhere. It also helps us automate processes and makes our workflows run smoothly. Danielle, our head of product education, uses our platform to manage knowledge base updates and assets. Jessie, who works on our product and success teams, uses it to manage product requests and measure customer satisfaction. There are dozens of other examples, most of which were planned via asynchronous collaboration.

And because Knack is so flexible, it allows us to continuously adapt to new ways of doing things that we uncover through feedback in our living discussion docs.

Sometimes We Synchronize

The ultimate goal isn’t to force everything into asynchronous collaboration. The goal is to help our team do their best work. Sometimes we work asynchronously, but not always. Sometimes we still schedule meetings, but maybe not as often.

It can also be helpful to establish overlap hours for a portion of the day. In our case, we ask employees to try and be online between 11 AM and 4 PM Eastern. Some people like to start early and end at 4. Others will start at 11 and end later.

Establishing some overlap allows us to interact spontaneously in the Slack messaging app. Sometimes it’s professional feedback, sometimes it’s sourdough baking results, and sometimes it’s responding with goofy emoji.

1-2 times per year (when there’s not a global pandemic), we also plan an IRL retreat.

And yes, sometimes we even use Zoom. In the new Work From Home world, it’s still nice to see our coworkers’ faces once in a while. And if we help each other do our best work in a way that embraces the messiness of life, those faces will almost always be smiling.