The Remote Roundup December 20, 2021

The Remote Roundup December 20, 2021

If you have ever been looking for a remote work strategy you may have noticed there exists a huge gap in between great insights and everything else out there.

So, we created The Remote Roundup where we will scour the internet for the best remote work content and give our analysis on one article while ranking the top 4 blogs of the week. Plus a podcast!

For the weekly collection of relevant and high quality remote work news, jobs, podcasts, guides, and expert advice from remote work experts, subscribe to our newsletter: The Remote Times. 

Ok, let's get started with the top remote content for the third week of December.

Top Article: The Unintended Consequences of The Hybrid-Work Model by Jack Kelly at Forbes

future of work

As we come barreling down towards the end of 2021, it's essential to reflect on what worked and what didn't.

Companies like Ripplematch that might have been against remote work before realized that a remote work policy was integral to retaining current employees in the face of the great resignation and attracting new ones.

It was also the year of the hybrid work model.

Executives tried to figure out the best ways to utilize the office and create a flexible working experience for all their employees.

Some even are encouraging working from anywhere, like at Slack.

On the opposite side, in the face of a new variant, large companies have postponed the return to office dates.

And brought even more uncertainty for their employees in this "Shybrid" approach.

If there were ever a time to have a New Years' resolution in business, it would be now.

One that swears by 2022 their company will have a clearly defined flexible work policy and the systems and people to help implement it.

If that doesn't happen, here are the potential pitfalls.

1. Unfulfilled expectations-

  • Without a clear policy, the life of managers becomes increasingly complex.

  • Anytime they want to schedule in-person meetings, they will have to do it weeks in advance.

  • Attempting to coordinate with each employee's time will be a headache and may force some to think that a full-return to the office is the best answer.

  • This will violate employees' expectations of flexible work and cause many to leave.

2. Unnecessary surveillance-

  • Now that most teams are distributed, fully remote, or a hybrid mix, companies that don't trust their employees will get more invasive.

  • ExpressVPN already estimates that 80% of managers utilize software to track employee productivity and the online activity on company equipment.

  • A prediction from Gartner is that 75% of conversations at the office may be recorded by 2025.

  • Employees feeling like they are constantly being watched will be less motivated to perform, and the organization as a whole slows down.

3. Resentment among employees-

  • You need intentional communication that encourages others to always include remote workers in meetings and operations, or you set up your company to develop in-office cliques.

  • Ones that exclude remote workers from important conversations and promotion opportunities.

  • It goes the other way too. The in-office employees will grow to resent the remote people for working while traveling or in differences in living standards.

  • They will wonder why they have to share a San Francisco apartment when someone lives comfortably in their own house on the coast in Maine.

4. Continued misconceptions-

  • Manager's roles will become even more ambiguous and stressful as they now have to worry about vaccine mandates, maskwearing, and who gets to work from home on certain days.

  • If they don't get rid of the pre-pandemic notion that attendance and long hours equal productivity they will start to question remote worker's sick days or vacations. Even asking why they need the time off.

  • If there are any bumps, they could be quick to blame remote work and how it decreased overall productivity.

The point is, don't fall into the trap that many companies have this year of giving up on the future of work because it's challenging to coordinate.

There needs to be a company-wide acceptance that they can be more agile and their workers will be happier if they have a clearly defined flexible-work policy.

If 2021 was the year that everyone experimented with different working arrangements, 2022 would be the year that companies allow everyone to work remotely.

Hybrid has too many variables for organizations to get right consistently without adopting a remote-first mindset.

Top Blog Posts

4. The TimeCamp Blog gives a detailed definition of flextime, what it is, and how to manage it.

flex time


Flextime is a working arrangement where employees can set their hours around their personal life. It enhances worker health and is the number one benefit that prospective talent is asking for.

Time Camp goes over every aspect of this arrangement in the different forms it appears. From job sharing to comp time.

They explain the benefits from increased work-life balance to improving cost-efficiency for the business. The challenges if it isn't implemented or practiced correctly are mismatched expectations between the worker, their employer, and their close friends. 

The most important thing to do when creating a flextime policy at your organization is creating clear guidelines. 

3. The Workplaceless blog answers the question if remote teams can be creative

can remote team be creative


A popular myth is that remote teams are less innovative than in-person teams. Why?

Because they don't have the same serendipitous interactions as teams do when they are working in the office. The random conversations at the water cooler or in the cafeteria that led to breakthroughs in important projects or designs.

But let's be honest, how many times did you have an epiphany while getting your Monday morning coffee and talking to Jake from accounting about his weekend? 

New research has come out from the Scientific American that actually hybrid an remote teams can gain an innovative advantage over in-person teams. They can have the same type of spontaneous innovation through virtual brainstorming sessions and intentional communication.

This is all without the downfalls of in-person collaboration in the office where often the loudest people are the ones who are heard, there is more tendency to move towards a consensus rather than the best idea and its harder to achieve deep work focus time. 

Remote work is perfect for "Aha Moments" because it allows you to take a step back and make all the necessary connections in your free-time. To enable this creativity Workplaceless recommends gaining inspiration from your environment. You should also create an open and inclusive space for Brainstorming.

2. Luke Thomas of the Friday blog explains why a wiki should not be the home for your company.

team management


In this interesting article that relates to the future of remote operations, Luke Thomas, The CEO of, shares why wiki programs like Notion and Confluence don't scale for distribute teams of 50+ people. 

Remote work requires documentation. Everyone working on remote teams understands that their processes, ideas, and meetings should all be recorded in one central location.

When company first start out with a couple people most will keep everything in the Google suite. Anyone who has every used Google docs will tell you that this is terrible for organization as they only have folders and things get messy fast. 

The next step is that as the company grows they will start using a wiki solution and things seem great. That is until their organization reaches more than 25 people and that digital filing cabinet that has the company handbook and the onboarding flows and the marketing strategy, starts to break. 

The problem he says is that employees rarely will update the wikis on their own accord and it gets left delegated to one person or a few managers. The structure also starts to fall apart with so much information and adding a methodology for organization is just a bandaid solution. 

That is why more remote companies are moving to solutions like Friday as their digital HQ where everything can be integrated and reached from one place. It is dynamic and interactive and everyone contributes.

1. Joe Thomas of the Loom blog details the three ways to use async to get to $10B

asynchronous work


Joe Thomas is the founder and CEO of Loom and he whole heartedly believes you can scale a billion dollar organization asynchronously. Don't believe him? Well, that is how he got Loom to where it is today and he gives the examples of Figma, Gitlab, and Upwork to demonstrate it is possible for various organizations. 

The first example he gives is how Figma created their highly popular collaborative whiteboard called Figjam. They created it in just six months, entirely remote, and using internal and external feedback. For the internal feedback they made a channel where the entire company could post their opinions. For the external they had app testers send in videos.

He then explains how Gitlab creates an amazing asynchronous employee experience through their employee handbook. Clocking in at over 2,000 pages, it is a masterpiece is sharing knowledge communicating publicly, clarifying exactly what needs to be synchronous and challenges existing norms or assumptions in office work.  

His final example is of Upwork where they have built async features into their product to help facilitate the connections between freelancers and companies.

Upwork realized early on through surveys that synchronous collaboration tools like phone calls and required video calls weren't working and slowing down project completion times. They created voice recording features, copying messages and milestones to make the communication cycles shorter and save time. 

Best Podcast: Alastair Simpson, VP of design at Dropbox comes on the Remote First Podcast to discuss how they unlearned the way they used to work.

remote first podcast



On the Remote First Podcast, Alastair Simpson, VP of design at Dropbox comes on to explain how he has been leading the company's virtual-first initiative these past two years.

The fact that this transformation is Design-Led is quite unique yet it makes so much sense.

For remote work to function, there needs to be intentionality that only a designer would understand.

Alastair walks Daphneé through the exact framework Dropbox used for the switch to a remote-first mindset and how the company is handling their processes today.

To adopt this mindset he explains they had to unlearn their previous habits and ideas about how work should be performed.

Check out this week's featured podcast!


Like what you read?

If you want more content like this sent straight to your inbox every Friday then sign up for The Remote Times

And make sure to check out our other blog posts where we give key remote work tips every week! 

See you next year for 2022's first edition of the Remote Roundup! Expect a new format, new content, and more surprises in the future of work!

In case you missed it:

The Remote Roundup December 13, 2021

The Remote Roundup December 3, 2021


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Mark Gregory

December 20

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