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Why you can’t manage your remote workers the old way

And 8 things you need to change

Barrett Dilger

October 31, 2022

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Remote Manager

Business as usual is no longer a thing. The pandemic flipped everything on its head and ushered in what is commonly referred to as the “new normal.”  Some would argue that it changed everything while others might argue that it simply brought the inevitable sooner. Either way, businesses have changed forever, and therefore managing them has as well.

Have you felt the strain of this change though? Are you wondering why managing your team doesn’t get the results it use to? Is it a struggle to do what came naturally before? Are you trying to figure out what isn’t working, or why it doesn’t feel right?  Or perhaps you have full awareness that what you use to do doesn’t work any longer. But why?

There’s an entire thought process to get into here, but that would be its own article in itself.  To briefly summarize though, there are two types of work. Synchronous and Asynchronous.  Synchronous work is “in sync” with other workers.  This is where a person’s work is reliant on another’s and done at the same time.  If one person doesn’t do their job, then it creates a bottleneck and stops the entire process. Asynchronous work is the opposite. This is work that is independent of others and can be accomplished alone.  Various job types are sync or async by nature. Here’s the hitch though, most jobs have been thrown erroneously into a sync category by default.

Historically, businesses functioned in the same building. Period. There were office hours, and everybody showed up to the same place and worked those same hours.  It was just how things were done because there really wasn’t another choice.  There were very small changes to that methodology, but mostly those were outliers, and the majority of businesses ran things the same way. There really wasn’t incentive to not operate in a synchronous manner. It’s how everybody was used to working.

Until it wasn’t.

Cue the pandemic. A little viral spread and some lockdowns later, everybody got a taste of what it was to work at home.  A great population of the working force was exposed to an asynchronous workflow.  And they loved it.

You mean I can pause my work to go water my garden?  I can work at night when I focus better? Yes, you can.  The big factor in that is they got to decide what worked best for them. They were masters of their own domain.  In full control. In most cases, their productivity skyrocketed.

Naturally, their managers hated it. 

I can’t “see” you working, so I must assume you aren’t! Most managers think their employees do less than when they are in the office, whereas most employees actually do more. Old school management didn’t adjust well to this change. It is based on a synchronous style, and it simply doesn’t fit async workflows. The historical way of managing just didn’t work. 

There were no visual cues in the office because nobody was in the office. There were no quick comments in the hall as you passed each other. Techniques used to manage their employees went out the window.

Basically, all the measurements of being in person are now gone when you manage a remote team.

Bad Manager

That is why you can’t manage remote workers the old way. The synchronous way.

In my opinion, this is currently the biggest issue in the job market right now. Simply put, there’s a tension between trying to put things back to pre-pandemic status (spoiler: that’s not going to happen) and workers who aren’t taking a job unless they can do it on their own terms.

There is a solution though.

The old dogs need to learn new tricks.

Sync style management just doesn’t work in the current work environment. Managers need to adapt their styles and techniques. It won’t be easy, as most managers and workers lack historical experience with it. Rest assured, it is the proper way to tackle this challenge.

The onus is on management though to establish what a functioning team looks like, and then present that as the structure that remote employees need to work under.

Modern working environments have evolved and old-school methods of managing need to evolve with them.

Here are our 8 tips for how to manage remote workers effectively:

  1. Focus on Communication
  2. Pick the Right Technology
  3. Use a Project Management System
  4. Set Official Procedures
  5. Allow Flexible Work Schedules
  6. Measure Productivity with Results, not Work
  7. Review and Reflect
  8. Meet in Person

Focus on Communication

Tip 1 is without a doubt the biggest of the list and is comprised of many subtopics. The first step is to recognize that remote communication is more difficult than in person.  That may seem fairly obvious, but what it translates to is that you need to double down on communication.  Whatever you think is enough communication to manage properly – double it.  Your team needs it, and you need the feedback. This is your primary tool now to manage effectively.

Communicate
Establish how you want to communicate, and its priority of importance.

This may vary from company to company but as a general rule of thumb, video calls are the top priority in communication. Follow that with standard audio phone calls, and further by direct chat messaging.  Email wraps up the tail of the list. Need something done? Email it off. Need it done now, jump on a video call.

Use screen recordings

Communicating in chat and email is difficult sometimes. There’s a nuance to communication that is lost…which is why we added emojis. 🤦  Remember though, a picture is worth a thousand words. You can easily send screenshots, and even notate them. Better yet, send a screen capture video. We are partial to Snagit, but there are other tools that doe the job equally as well, such as ShareX.

Create a meeting schedule.

You should have regular meetings to keep the team connected. The frequency might differ from company to company or team to team, but weekly is a good target.  Daily might be too much, or just perfect if you have a fast-moving project. Always have clear goals for your meeting to make sure they are productive. Nobody likes having meetings just for the sake of having meetings.

You might need to shift your habits though.  You know those status meetings where everyone updates on what they have accomplished and what they are doing next?  Progress tracking doesn’t technically need to be live.  Again, maybe your business or projects are better suited to be handled that way, but if you can’t define exactly why, then they probably aren’t.  Is there a reason why their “reporting” can’t be an email for you to review at a time that works for you? You can get back to them with thoughtful notes for moving forward and how you will address blockers that slow their work. You can then update it in your project management system (more on this to come) so the whole team is updated. 

Think about what you need to meet on, and those key meetings should be the scheduled live ones. Major project updates, conflict resolutions, and new team member additions should all be live meetings.

Focus on collaboration.

Set your team up with collaboration as the foundation. Give them good, and easy, ways to work together with files and documents. There is no one size fits all, and you might need to implement multiple solutions for different groups or alternate solutions for different projects. Doing this is critical, not just for getting the job done, but also for preventing frustration and burnout.

Make sure to set up a virtual watercooler.

You get the analogy. People in the office would run into each other at the watercooler and stand around chit-chatting. Maybe about work. Maybe about their kids or what they are doing this weekend.  You need that. It builds camaraderie.

Implement that in your virtual office by having an always open chat room where people can relax and chew the fat. You can also schedule a virtual meeting once a week for people to show up and NOT talk about work. Just to hang out, grab a drink, and socialize.  That time will pay back in spades when it comes to overall job satisfaction, team quality, and productivity.

Virtual Watercooler
One warning though.

Be aware of message overload.  The constant ding and message alerts are known to bring on fatigue.  Set your rules, and let employees silence or snooze under certain circumstances. Absolutely promote turning off notifications after hours. If you provide a work phone number (one that routes to their PC or mobile via VoIP) you can schedule this for them so it’s never an issue.

Pick the Right Technology

Confused Tech

Picking technology that provides a solution you need is one thing but picking one…let’s just say… that doesn’t just tick people off is another.  Sorry if that sounds harsh, but it is serious. If you expect your employees to use these apps daily, then make sure to do your due diligence and vet them first. Make sure they actually do what they say they do. Make sure they are set up properly with optimized settings. If you don’t then this will majorly increase user frustration and will add to the use of Shadow IT (when your employees pick their own apps to use, instead of your approved ones) and therefore increase your risk of a breach. We’ll get to that more later.

The number one reason employees dislike remote work is because they feel disconnected.  This overlaps with the communication topic but is more focused on how you communicate.  Are they set up with a good camera and screen so meetings aren’t a painful experience? Did you choose a chat platform that is easy to use and fits their needs? Did you make sure that shared files are organized properly so they aren’t always searching around?  Data shows that employees waste about an hour a day searching through their storage and chats looking for files. Choosing the right tech to accomplish communication and collaboration is essential.

Most importantly with your tech in mind, setting up your infrastructure to be secure is on top of the list.  When businesses implement remote working, they are significantly more vulnerable to data breaches. With only 44% of businesses providing cybersecurity training, it’s no wonder that 20% of breaches came from remote workers.

You need to ensure that your network is secure, your users are secure, and that they connect securely. You need to implement robust cybersecurity layers to decrease your risk of data breaches. 26% of businesses don’t have a solution in place to detect and stop ransomware attacks on their workstations. That’s just wrong.

Part of that process is establishing your approved, official application policy. This policy isn’t just a “preferred” list but is the mandatory list of what to use. Anything unauthorized is considered Shadow IT and should be addressed immediately to keep your business locked down and secure.

Use Project Management System

With in-office work, you could skate by not using a Project Management System.  With remote work, you really need to use one.  And when I say to use one, I mean actually use it.  I know, you’re hesitant. I can relate as well. I’m a spreadsheet guy myself so naturally gravitate there for management, but the benefits of project management software are undeniable. Yes, it will be a pain at first but it will find it becomes a very effective tool and gives you great visibility to your projects.

If you need to look into one, Asana, Basecamp, Jira, and Monday.com are popular choices. If you want to stick with Microsoft Apps since you probably already have them, you can create Team Channels for projects and integrate Planner for your tasks.

Project Management

Set Official Procedures

When I wrote about better offboarding of your employees, I talked about how you should establish a culture of documenting workflows. You should already have the major framework done, but your employees can keep the nuances updated so it’s clear to anybody else what needs to be done.

This is so important, and even more so when dealing with remote workers.

To execute work efficiently, you need to implement systems. The work, its criteria, and related workflow need to be documented.  Breaking the work down into a process, and if possible as an easy-to-reference checklist, will bring consistency to the outcome.  This structure ensures that people are aware of how and when work needs to be completed, and how it relates to other team members and their work.  As your business grows, this process will scale with it. Without it, the work will become harder to do and manage, and your team will suffer.

Allow Flexible Work Schedules

One of the most attractive things about remote working is a flexible work schedule.  To keep your team happy and productive, make sure to allow a flexible work schedule. There’s multiple ways of handling this, and remote work is just one category. Define what works for your business and build your team around it.

Communication is key in this regard as well.  You should know your team and their schedule. Maybe one person works 8 hours straight, but they shift by an hour because they get their kids to school. Another might split their day and not be available in the afternoon. It just means talking about it.

Work Schedule

It’s ok to have mandatory times as well.  There might be times when the team needs to collaborate in real-time. You scheduled your team meetings every week (as discussed above) that they need to attend. These are mandated work times.

Having structure is good, and needed, but remember to stay flexible.

Do you have team members in other time zones? Are you allowing for breaks when your employee feels they need to take a break? Are you remembering that “Work From Home” doesn’t necessarily mean “Work At Home”?

The focus here is on efficiency, not on how long somebody is working.

Hot tip to consider: be aware of people working multiple jobs.

In this modern work era, there have been people deciding to take on two remote jobs at the same time. 

From a business perspective, I think overall the feeling here is negative in nature, that working multiple jobs would be not working “fully” for you.  With no other context, I’m apt to agree. Multiple full-time jobs would spread somebody thin, and probably not give you their best work. Depending on the work, it might even create a conflict of interest.

However, think about it this way; if somebody worked in the office 40 hours a week and had a side hustle nights and weekends, would you care?  So now that they have flexible hours and the workday is not so clear cut, does that make a difference? Maybe you are happy with their output, so you are just glad to have them on your team. It might not make a difference to you. If it does though, think about how you will handle that scenario in case it arises.

Either way, remember that you are measuring their results, not minutes clocked in.

This brings us to our next topic.

Measure Productivity with Results, not Work

A major challenge in remote management is tracking productivity and accountability.  As an operations guy, I swear by the creed, “You can’t manage what you don’t measure.” Measure everything. Better to have too much data than too little.

Doing so for remote workers is a difficult task though. There are tech solutions for this, but they aren’t a golden answer. These tech answers can track everything: Applications used, mouse movements, keystrokes, and pretty much everything you do on a computer. 

Should you do this?

Only you can make that call. Sure, I just said to measure everything. You need to make the decision for your business about what is relevant though. What are your KPIs? Is keyboard use a proper reflection of those?

When we tell people to do their jobs, we get workers. When we trust people to get the job done, we get leaders.

Simon Sinek

As Simon Sinek has said, “When we tell people to do their jobs, we get workers. When we trust people to get the job done, we get leaders.” Maybe workstation use isn’t the best measurement. 

On the other hand, monitoring doesn’t have to be your guiding principle. Maybe you have an employee that is twice as productive as the average, but with half the workstation usage. Knowing this you might be able to start looking into it and asking questions why.  Not to praise or reprimand anybody, but to explore how your company can become more efficient.

No matter which direction you go, make sure to be clear in your goals. You aren’t trying to micromanage tasks, you’re tracking productivity and accountability. If this isn’t abundantly clear, you are essentially using synchronous management on an asynchronous workspace. The result will be “digital presenteeism” where employees present themselves as if they are available or working at specific times, rather than actually being productive.  It’s the equivalent of somebody walking around the office holding a file folder. They “look” like they are working because they are holding a file folder, so nobody questions it. 

You don’t want that scenario where people are focusing on looking like they are working. You don’t want smoke and mirrors. You want trust. With trust, you get people focusing on doing their best instead and achieving goals.  Always remember you are measuring results, not work.

Review and Reflect

Reviews have always been part of the management process.  It remains very relevant with remote workers as well.  Never underestimate that one-on-one conversation and the impact it has.  You should be guiding each employee to success – theirs, yours, and the company’s.

Don’t stop there though.  Implement a 360 review as well. Not only review the worker but ask for feedback from their perspective.  How are the employees they deal with frequently? How is management?

Where on a daily/weekly basis you are measuring how hard and efficiently the team is working, the review process is to measure feelings, perceptions, and advantages. You’re looking for strengths and weaknesses for everybody, and then catering to their strengths.

Meet in Person

This one might seem counterintuitive for a “remote work” scenario, but you really should meet in person when you can. Perhaps during year-end holidays makes perfect sense. If your team is widespread maybe a summer schedule would be better. But pick a time during the year and gather your flock.

Have a party, go on a retreat, do something to celebrate your team. 

The result will be tighter camaraderie and a better understanding of each person. Seeing each other in-person allows everyone to get to know each other in a different light. In-person you pick up on nuances that you don’t on camera or in chat. You get little details of personal preferences that you wouldn’t get otherwise. You see non-verbal cues in how they react and learn what they like and don’t like. You really get to know them.  And when I say “you”, it isn’t just you but your entire team.  It’s a team-building process that is immeasurable.

Hopefully, you resonate with these tips and see their power. If you aren’t doing some of them (or any of them) you should implement them now to improve your management of your remote team. You will certainly see the ROI quickly.


If you have any thoughts to share on the topic, drop them in the comments section.  It’s never a one size fits all, so I’d love to hear what you do that I missed, or what your experience has been.

As always, if you have any questions or needs for the technology side of management, feel free to reach out and see how we can help.  You can always schedule a 15 min consultation on our live calendar, no strings attached.


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