How We’re Overcoming The Challenges of Working Remotely

Scaling / July 20, 2017 / Kristie

If you’ve tried working remotely as a company, you’ve probably experienced some challenges like staying updated on where projects are at and keeping a tight knit culture.


But that doesn’t have to stop you from giving your team the flexibility and increased productivity that comes with working remote.

We’ve slowly been transitioning our company to be accustomed to working more remotely. We started by introducing Tuesdays and Thursdays as work from home days for our dev team. The main reason was twofold; more flexibility and more focused work. To maximize productivity, we decided to move to a remote environment which provided not only the flexibility many folks appreciate but also a distraction-free environment where they could be more focused.

Once we saw how well that worked, we rolled out Tuesdays and Thursdays as work from home days for everyone. After adjusting some workflows and overcoming some of the challenges of remote work, we took it a step further.

Now our team works from home around 80% of the time, and only comes into the office Mondays, Wednesdays, and Fridays every other week. Our next step that we’re working towards is coming in only on an as-needed basis.

Benefits of working remotely

Working from home can benefit both employees as well as the company. Remote work means less travel time for employees, which has many benefits in itself. Ever met anyone that enjoys being stuck in traffic? Me neither. When your team doesn’t have to spend time and money commuting, it creates a happier work environment for them and reduces stress.

The cost of living is higher in the city than in the suburbs, so folks can own a home as apposed to having to rent. And different people have different lifestyles – some might want to live on a farm, a secluded home in the woods, or in the middle of downtown on the busiest street. Working remote gives people more flexibility to work where they want, and live where they want.

Another benefit for the company is that the talent pool increases when you’re not limited to location. There are even free resources available like Hubstaff Talent for finding remote talent.

Arguably the biggest benefit we’ve noticed is an increase in productivity since our team has been working more remotely. I personally get way more work done when I’m working from home because there are fewer distractions and I’m overall in a better mood. When I can start my day after a walk with my dog instead of being stuck in traffic, I’m much happier and in a better frame of mind to focus on my work. A more positive mindset plus more focused work means we get more out of our team than we would if they were working in an office.

The 2 main challenges of working more remotely

While working remotely has a lot of perks, it also comes with some challenges. Here are the two main ones we faced:

  1. Knowing what’s going on
  2. Keeping our culture

When you’re working in a remote environment, it’s hard to stay informed about what people are working on and how projects are progressing. Also, when people aren’t connecting, seeing or interacting each with each other, keeping a company culture can be a challenge. People can start to feel isolated and less engaged with the team and their work.

Overcoming the challenge of staying informed

Here are some things we do to make sure everyone knows what we’re focusing on as a company, where we’re at, and what people are working towards.

Monthly All Hands

At the beginning of each month, we have a company-wide meeting that can happen either in person or remotely via Zoom. These are usually an hour or two, and we try to include more than one presenter, so we’re updating everyone on goals for the company and within departments. We review our goals and metrics for the year, the quarter, and give a quick update on where we’re at for each of our priorities. We also use this opportunity to raise any new internal initiatives, company events, introduce new hires, etc.

Weekly Meetings

Each week we have a weekly meeting for the exec team and within each department. We review our goals, metrics, and where we are. We plan out our priorities for the week (or, depending on the department, two weeks), and discuss any bottlenecks that might prevent us from achieving our priorities. These meetings are usually an hour long so we have enough time to cover status updates, challenges or red flags, and discuss if any of our plans need adjusting.

Daily Huddles

We have quick stand up meetings daily that are usually only about 15 minutes long. We take turns celebrating victories from yesterday, our top priority for today, and any challenges or bottlenecks. The idea is that these are short and sweet so we know if any red flags need attention and so everyone is updated on priorities.

Internal Newsletter

Every month we send out a newsletter to everyone in the company as a short update from each department. The newsletter outlines what we have accomplished, any challenges that we’ve had to overcome, and what we’re planning for next month. We also include our stats for the quarter, who has a birthday or work anniversary that month, and our employee “props”, which I’ve written about lower down in this post.

Collaborating/ Tools We Use

We use a variety of tools to collaborate, share project and task info as well as to stay updated on things. Here are the most common ones used within our departments:

  • Daylite: To track projects and delegate tasks and to check each other’s schedules as well as book appointments. We use the Team View to see what’s on each other’s plate. We have multiple shared Smart Lists for example, a shared calendar for email blasts and blog posts so everyone knows what’s coming down the pipes.
  • Confluence: To collaborate on projects and document decisions. We can comment on pages so we have the history of communication for the project, and can post design mockups, videos, etc. In our Marketing Team we also use Confluence to customize a dashboard of our weekly metrics, quarterly priority, and top 3 priorities for the week for each team member.
  • HipChat: To communicate one on one or in a room as a group on things that need discussions.
  • Zoom: To schedule video meetings where we need to discuss things or share our screens to draw out ideas.
  • iCloud: We use shared iCloud docs for editing and reviewing written content, sharing spreadsheets to track company metrics, etc.
  • Jell: We’ve recently started using Jell within some teams to post our daily victories, priorities, and challenges. We also use Jell to collect feedback from our team for weekly one-on-ones to gauge how people are doing, top priorities for the upcoming week, what’s working or not working, etc.

Overcoming the challenge of company culture

Here are some of the things we do to keep our team members connected and build our company culture.

Team Building Exercises

We schedule regular team building events like going to an escape room or doing trivia. By putting people together in teams that don’t normally work together, we create bonds between teams.

Cross-Department Teams

One of the problems many companies face is departments start working in silos; they stop communicating with other departments. This causes a lot of friction and can be bottlenecks. To combat this, we’ve started forming cross-department teams so we have people from different departments communicating regularly. This helps bridge teams together; leveraging different people’s skills to solve problems and helps us work more as a team instead of as different tribes.

Pair Discussions

We’ve recently starting having bi-weekly remote calls/meetings where we match people that don’t normally work together. We schedule 20 minutes at the beginning of the week and the end of the week. During the call, we have a short catch up on what’s going on in our lives, talk about each person’s top priority for the week, and any roadblocks. Then at the end of the week, we do another 20-minute call where we talk about how our week went, whether or not we accomplished that priority, and challenges we faced. This has been a really great exercise because it creates a stronger relationship between team members, builds empathy for other teams because we know challenges they face, and can even help problem-solve challenges by having a new perspective.

Learning Curve 

We started a book club about 6 months ago so we can read books together about self-development and business. We meet every other week either in person or remotely via Zoom for about half an hour. We chat about what we read, what we liked, disliked about the book, but most importantly – what we learned and how we can apply it to our work here at Marketcircle and our personal lives. By learning things together, we’re challenging each other and regularly finding ways to improve internal processes and decision making.

I’ve found these 3 books to have been the most influential:

The Happiness Advantage: The Seven Principles of Positive Psychology That Fuel Success and Performance at Work

How To Win Friends & Influence People

Great by Choice: Uncertainty, Chaos, and Luck–Why Some Thrive Despite Them All

The “Props” Wall

We took over a wall in the office and built what we call our Props Wall. The wall has a photo of each employee and under each person’s photo is their name, a fun title that describes their role (but with more personality), their birthday, a fun fact about them, and a little pocket for leaving each other notes (or what we call “props). The idea is that whenever we see someone demonstrating one of our core values, we write a note about how they’re living that core value. We then include all the “props” people got for the month in our monthly newsletter.

Meet Ups

Not everyone lives close to each other, but we encourage those who can to schedule meet ups so we build closer relationships with one another. We have a HipChat room for get-togethers so everyone knows when we’re planning a drinks downtown, or meeting up in a coffee shop to collaborate and work together. This doesn’t work for everyone, but for our Marketing Team, since we all live downtown, we’ve started getting together once a month for lunch during a work-from-home week.

These are just some of the things we do as a company to build our culture and help keep everyone in the loop, while gaining the benefits of working remotely. Have ways that you keep your company aligned when you’re not working together in the office? Tweet us and share your ideas!

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