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Best Investment for an Entrepreneur in 2021

Don’t worry this isn’t a new years post about how the best investment in 2021 is in yourself. Although there may be some truth to that common answer I want to take a more objective view about where is the best place to deploy capital in 2021 for your business. 

  • Is it in the stock market… ARK ETFs are booming, TSLA, new SPACs?
  • Is it in cryptocurrency?
  • Is it in precious metals?
  • What about wine, art and trading cards?  

All of the above at/near all time highs in terms of their price.

What I would argue is the best place to look is in an asset class that has…

  1. Increased in quality in 2020
  2. Reduced in cost in 2020
  3. Is Low risk & has High probability of a return

My argument for the best investment in 2021 is people… 2021 the best investment opportunity is building your team. 

Currently, we have 30 team members on the payroll and many more working as freelancers with plans for growth in 2021. 

Why do I argue that the best investment opportunity is human capital?

Lets look in more detail at the dimensions that would make it a good investment… quality, cost and risk/reward. 

Increased in Quality in 2020

With the increase in the unemployment rate and significant movement of employees between sectors we have seen an improvement in the quality of available applicants to job postings. 

Compared to other possible investments I can think of few where their quality increased by the amount the available labor pool did. If the quality of the available candidates is correlated to the unemployment rate (obviously a massive simplification) then the quality of the available labour is up 75% compared to this time 1 year ago. 


Reduced in Cost in 2020

As the unemployment rate went up AND people started looking at alternative lifestyle choices…. Working 70+ hour weeks in the city not seeing their family started to not make as much sense. 

People are re-evaluating their decision between money and lifestyle… if you can meet that need with a fliexible employment offer that values them then total compensation does not need to directly compete with their previous roles.

The labour statistics also point to falling wages… 

“In some countries where they are available, labour statistics point to falling wages. In Australia, nominal average wages of workers aged 50 to 59 years old declined by 3.2% between the week ending March 14, 2020 and the week ending June 13, 2020.”


Low Risk and has a High Probability of a Return

This one becomes a little more debatable/unique to everyones situation…if you pay wages and nothing productive gets built then its a complete loss. 

Everyone needs to make this decision on their own and it is outside the scope of this short article. 

My greatest investments have clearly been getting the right managers on the team. 

However, getting this wrong also leads to some serious pain that isn’t just financial. 

Summary and My Take Away:

As a result of this thought process we are ramping up hiring for a few roles (writers, editors and a business manager). These new team members will be tackling a couple new projects and putting some additional horsepower behind some projects that have gained great traction in Q4. 

5 Step Personality Assessment Team Building Plan Free

As companies continue to work remotely many of us are faced with the question of how do we work with our teams remotely better? 

Today I am going to share what we are doing using the DISC Assessment for Team Building purposes. This works directly into our system for how to manage staff remotely.

Some people on our team really enjoy the small chat, sharing jokes while others just want to get to work and be left alone. 

It is not JUST up to the leadership to understand everyone but if the team works with each other we all have a responsibility to understand how each of us are most effective. 

So… how are we going to go about improving our teams performance with a personality assessment? 

We are using the remarkably accurate DISC Assessment tool, create a personalized action plan off of the results and share the findings with the rest of the team. 

What is the DISC Personality Assessment?

Here are the steps to implement this assessment we are using with our team… 

DISC Assessment for Team Building Steps

Step 1 – Prepare the Team DISC Assessment Plan

In this step decide on the following items…

  1. Who on the team is going to complete the assessment
  2. How is the assessment going to be completed?
    1. Free Online Options – such as my favorite
    2. Paid Consultants or Paid online options
  3. Is taking the assessment required? In my case I have decided to not make it required although encouraged. 
  4. Setup Google Sheet to share results
    1. See example here

Step 2 – Introduce the Team to The DISC Assessment Plan

Share with the team why we are doing this and how it is going to get done.

/// my email ///

Hi Team

As mentioned on the morning call I continue to be impressed with how the team is performing remotely. 

The purpose of this email is to layout the plan for taking the personality assessment discussed so we can work even better together. The team we have now is crushing through work and we definitely have the core team to keep building from.  

Through this process, we might even finally find out what is wrong with all of us 😉

2 parts in this Email:

  • ONE – The Plan
  • TWO – My Experience and the Why

ONE – Create The Plan

  1. Go to this site –
  2. Take the 10 min survey
  3. Read your results and see if you agree with them
  4. Optional – Add a link to your results in this google doc – LINK
  5. Add your direct reports to the sheet and share this email with them
  6. Review each of the entire team members summary with a focus on your direct contacts (manager and reports) – read post at AWI on debrief process
  7. We will discuss one persons results at each of the morning meetings (with myself going first) – read post at AWI on sharing process

The end result is every person will have taken the DISC assessment, shared with the entire team their results and created an action plan adjusting work to focus on strengths and mitigate weakenesses. 

This will also allow us to better understand how to work with each other most effectively.  

TWO – My Experience and the Why

As you can guess I am usually fairly dismissive of this soft stuff. However, when I completed it I was like holy shit this is spot on. Get out of my head computer! 

I am a big believer in doubling down on strengths and putting systems/people in place to mitigate weaknesses. 

The level of accuracy of the assessment certainly supported what were strengths and weaknesses. As a result, I am putting more effort into systematizing parts of the business. 

For example… this very effort is a systematic way to put in place an efficient way for us to better understand our differences and allow each of us (myself included) to work more effectively with everyone. Ideally leveraging a strength of mine (systems) to mitigate a weakness of mine (communicating I care about the team).

I welcome feedback and look forward to this process. 



Step 3 – Everyone Completes a DISC Assessment

Each person goes in and completes the DISC assessment entering their results into the spreadsheet. 

  • Go to
  • Complete the assessment
  • Read the results
  • If you agree with them and are okay sharing with them team enter into the spreadsheet

If you want you can add in a comment if there is anything you think is worth noting.

Step 4 – Debrief at the Weekly 1:1 Meeting

At your weekly 1:1 with either your manager or a direct report review the summary of the assessment and debrief. 

Consultants have gone in DEPTH on this debrief process –

For our purposes, I believe a shortened version consistent with an OODA loop is sufficient…

  • Observe
    • Any issues taking the assessment?
    • What did you think of the assessment?
  • Orient
    • Did you find it “fit” you?
    • What parts did you relate to the most?
    • What parts did you disagree with the most?
  • Decide
    • What changes to your work would play to your strengths and mitigate your weaknesses?
    • What changes to how you work with the team would play to your strengths and mitigate your weaknesses?
  • Act
    • Add a list of action items to the weekly sheet (or Trello board if used) for tracking to completion

Step 5 – Team Building Share at the Morning meeting

At the morning meeting, I would like to have one person each morning share their findings. 

5-10 min and some version of the agenda (your time to share):

  • Personality according to the tool – abcd
  • My thoughts on if it fits me
  • Any insights
  • How I am adapting my work to play to my strengths and mitigate weaknesses
  • How I am adapting how I work with others to play to my strengths and mitigate weaknesses 
  • Comments from the team

My hope is this team-wide, efficient approach to personality assessment will have a positive impact on both the quality/quantity of individual output while also providing a framework for helping us work better together. 

I am looking forward to the process and seeing how it goes. 

If anyone has had experience with this process in another organization comments below would be greatly appreciated! 

Ice Breakers For Remote Teams

This article is part of a series we are doing on remote work, a relevant topic in today’s times. With social distancing becoming the new normal, social isolation will also start to take place, especially when it comes to team building. When you are forced into remote work, you might find yourself with a lot of questions. You might have many things you feel like you need to do, and very little time to get it all organized. This article will focus on a simple part of this process – getting your employees familiar with each other through some simple team building introductions.

For more topics on how to best run a remote team checkout these articles…

How to Manager Remote Staff

Always On Video Solutions Reviewed

This article will hopefully give you the tools so you can have your team working together like this…

Not this…

When it comes to coordinating remote team members, often the most difficult part is getting them on the same page. This all starts with the introduction. This is a very simple part of any working relationship, but is more important than you may think. First impressions are everything, and if people feel connected to their virtual team from the start, they will be more willing and motivated to hold themselves accountable to the standards of their co-workers. 

In this article, we will cover some fun ice breaker questions and games for setting up your remote workers. These team ice breakers for remote team will get your employees introduced the right way. These are fun activities, which are easy to introduce, and will hopefully help things progress into a great working relationship. Let’s get started. 

20 Ice Breakers For Remote Employees

Tell Us About Yourself 

I know, this one’s a little boring, but it’s also by far the most common team building exercise, so good to get it out of the way first. A basic introduction probably is composed of “tell us a little bit about yourself”. We know, it might not be what you came to this list for, but it’s still a basic, effective and important introduction. If you just want to keep things simple and straightforward, consider this one. 

Two Truths and a Lie 

Maybe the second most common introduction game, this one has stood the test of time because it’s so fun and engaging. In this one, the participant tells two truths about themselves, and one lie, and the others guess which is the lie. This is great because it involves interaction with all the participants, which really makes them remember what the other person said. On top of that, these are fun icebreakers and often hilarious. If you really want to get these details drilled into people’s memories, consider this game. 

Favorite Food 

Here’s a simple question that surprisingly opens a pretty real discussion. Simply asking people about their favourite food or restaurant, you create an instant common ground, as well as some friendly competition. You’d be surprised just how much food can connect people, and since it is something that everyone is passionate about, it is a great question to ask off the bat. Immediate team bonding over common interests. 

Would You Rather? 

Always have a fun list of “Would You Rather?” questions on hand for virtual ice breakers (safe for work of course!). These questions are funny and really get people thinking. Keep it simple, because you’d be surprised just how entertaining the responses can be! Additionally, it encourages others to chime in with their thoughts, and laugh along. 


A unique factor with distributed teams is that everyone can be in a very different place in the world! That’s why simply asking where someone is from can be a fascinating exercise with remote teams. People will be very interested to see that they might be communicating with others all over the world. From there, you can get into deeper discussions about the favourite part of their hometown, and they can find some common ground with others from all around the world. 

Have You Ever?

In this game, you ask some simple, interesting questions to the group, and anyone who has done it will stand up. It’s easy, and best of all it basically hands the interaction to the group. No one really has to think about anything besides whether they have done it, and the whole group will learn something new. This is a great way to learn about people in a quick, organized manner. For remote teams, you can use video conferencing and have your team raise their hands instead of standing. 

Favorite Music

Music is another one of those things that connect people, similar to food above. You can learn a lot about someone by their favorite band, song, or genre. These building activities will instantly connect people, and have them feeling some common ground with other people who may be miles away. To mix it up a bit, you can ask “Who was the last artist you searched for on your music streaming service of choice?”.

Tell A Joke

Keep it safe for work of course! A joke can be a great way to break the ice. Have someone share their favorite joke, and see if you can get the team laughing. You can even start out with a joke before everything gets started, to loosen tension and break the ice for everyone. When it comes down to it, nothing unites people like some laughter. 


Another simple way to get people talking is to ask them about two similar objects (like ice cream vs. pizza) and ask them what their favorite is. This is a great game because it’s easy, but also generates a lot of healthy competition as people defend their favorite things. People find common ground amongst some healthy rivalry, while learning about each other as they go. 

Rock, Paper, Scissors

How about a quick rock, paper, scissors tournament to get things started? Have everyone play, with the winner advancing. It’s a fun game because everyone knows how to play, and you can get the remote team building started with some healthy competition as well. 

Draw Something

If you tell people to have a note taking pad and paper handy, it can be a fun start to have people draw their favorite animal (or any other fun ideas you can think up). The results are relatable, and often quite hilarious. It’s a really fun way to get things started and to have a shared, interesting experience. 

Favorite Hobby

Another classic question, finding out something about a person outside of work is always a great place to break the ice. This gets people talking about something they are truly interested in, instead of just jumping right into work. It also helps unite people, and lets them know a fun detail about the people they are working with. 

Don’t Laugh

This one is simple, first one to laugh loses. It can be a great way to break the tension that is almost always present upon first meetings. It is also easy because it doesn’t require anyone to speak, simply give them a fun game before they get started. 

What Is Your Role?

This one is a bit more organizational focused, but with remote teams it often can get confusing who even does what. By starting off by allowing everyone to explain their role, everyone gets a chance to introduce themselves, but you also get a way for everyone to understand which role on the team each person plays. 

Share a Photo or gif

Everyone has smart phones these days, so why not give them a chance to share a photo on their phone that they really like. It can be of anything, and they get a chance to explain to the group why it is so special to them. Of course, it’s important to make sure everyone is comfortable with the game beforehand, and can sit out if they like. 

How’s the Weather There?

Another fun game to play with remote teams is simply to ask how the weather is there. Because everyone might be in such different locations, it can be fun to compare what it’s like outside and this really helps to show how varied remote teams can be. When it’s snowing somewhere and sunny and warm elsewhere, that can be a real conversation starter! 

Who’s Your Team?

Sports is another way in which people find common bonds and playful rivalries. Asking about their favorite sports teams is a great icebreaker activity to open discussion. If they aren’t sports fans, they can always say something about the city they’re from. It’s a great way to let people get a gage of where everyone is from, and understand the truly “remote” nature of a team. 

Past Experience

We don’t want to risk any ice breaker questions sounding too much like an interview, but asking people about their past experience can be a great opening question so people can learn about each other. 

5 Quick Facts

Sometimes you can even send the participants a quick list of questions beforehand. You could send them 5 of any of the questions above, and have them rifle off 5 quick facts about themselves at the start of the meeting. This is a great way to quickly learn a bunch about the others, and they can figure it out beforehand to avoid being on the spot. 

Introduce Yourself

We saved the most basic for last, the open ended “introduce yourself”. A classic question that is surprisingly broad. Give people the chance to say a few short things about themselves, and see what happens. Sometimes the most classic ice breakers are the ones worth pursuing, especially when you don’t know the dynamic of your team yet. 

Important Considerations

Often the icebreaker that you choose is really more dependent on the situation at hand. There are various types of virtual groups, and various levels of professionalism you might expect from your team. This makes it difficult to know what level of sharing people are comfortable with right off the bat. We think these three key considerations are very valuable in choosing whether you want to err on the side of humor or professionalism: 

Is This The First Time Meeting?

Not all ice breakers take place on everyone’s first time meeting. Maybe this is simply their first time working remotely, or maybe many of them have shared experiences before. Regardless, it is often the case that everyone loosens up a lot more when they have met each other before. 

For this reason, you might want to avoid some of the more humorous ice breaker games and questions when it is everyone’s true first time meeting each other. This is for the simple reason that it might make some uncomfortable. When in doubt, pick a game you are sure everyone will enjoy. 

How Old Is Everyone?

The dynamics of a group will often change a lot depending on how old everyone is, or more specifically, how familiar is everyone with remote technology? Of course, we aren’t meaning to make broad generalizations on age, but it is often the case that people aren’t as comfortable joking around when there are large age differences. Your primary concern is finding an icebreaker that keeps everyone comfortable, so considering the different generational dynamics is often important. 

What Is Your Industry?

Simply put, different industries often have different standards of professionalism. Often, people enter meetings (especially first meetings) with an idea of keeping things quite professional. This is especially true in more “serious” professions that involve higher stakes. Keep this in mind when deciding on an icebreaker. They can be a great way to loosen tension, but don’t pick something that is inappropriate for the situation. 

Time Constraints

A final issue is time constraints. Depending on the size of your team, it may affect how simple or how complex you may make your icebreakers. You have to consider how long it will take everyone to answer, and you don’t want to run the risk of anyone losing interest, or of running out of time to get to the heart of the meeting. We included several options on our list which run a range of time to complete, and you can choose the one that best suits your needs. 


Overall, you just need to pick the icebreaker that you think fits the situation. Evaluate the dynamics, and decide what you want out of your remote group’s initial meeting. So take some time to sit down and really figure out what you are wanting out of this meeting, and pick an icebreaker to match. We’re confident you can find one in our options above. 

Thank you for reading our list of ice breaker games for remote teams. Remote teams present a special issue in getting everyone acquainted, as you often don’t get the opportunity to meet them in person. But with a good icebreaker, you’d be surprised how quickly everyone can come together! 

Frequently Asked Questions (FAQ)

Q: How do you make a team call fun?

A: Turning a virtual call into a fun activity for a team member can be easily done by incorporating the ice breakers included in this article. Pick one and start off your next meeting or call with it!

Q: What are your top tips for team building with remote teams?

A: Incorporate an all-hands meeting every morning with your team, especially if the majority of your employees are working remote. Within these you can include the ice breaker ideas above multiple times with everyone – having your colleagues learn more about themselves brings everyone closer together and keeps people on their feet for every meeting. 

Q: I’m not great at coming up with ice breaker questions. Do you have any good examples I can use?

A: Of course! Here’s some great group icebreakers to improve communication and build an overall better company culture:

If you had to delete all but three apps from your smartphone, which ones would you keep?

You can have an unlimited supply of one thing for the rest of your life, what is it?

How would you change your life today if the average life expectancy was 400 years?

What would you be found doing if the police unexpectedly breaks into your home in the day?

If you could be in any movie, what would it be and what character would you play?

If your life were a hero’s journey, who would be your antagonist and what’s stopping you from winning?

If you had to eat only one type of food for the rest of your life, what would it be?

If you could know the absolute and total truth to one question, what question would you ask?

If you could choose any historical figure to be your imaginary friend, who would it be and why?

If you could choose to remain one age until you die, which age would you choose and why?

If you could choose any person from history to be your imaginary friend, who would it be and why?

If you can go back to college again, would you take the same course that you finished or try out a different one?

If you could live anywhere on this planet without having the leave anyone or anything behind, where would you live?

If you could add a word to the dictionary what would you add and what would it mean?

If you had to identify one person who completely changed your life, who would it be?

If you could go back to your younger self, which age would it be, and what would you say?

If extraterrestrials landed on earth and offered to take you with them, would you go?

If you can go back to any of your younger selves, at what age would you choose to go back to?

If you could travel to and live in any time period in history, where and when would you live?

What is something that you believe in that most people probably don’t believe in?

If you could visit anywhere in the world, regardless of budget or time it took to get there, where would you go?

If you could commit any crime and get away with it what would you choose and why?

If you could have the power of teleportation right now, where would you go and why?

Use a word that begins with the same letter as your first name to describe yourself and why?

What’s something that someone has said about you that has really stuck with you?

If you could buy any .com domain, what would you buy and what would you use it for?

Tell us a book or movie or video you’ve read or seen lately and which you would recommend?

4 Always on Video for Remote Teams Tools Reviewed

Coronavirus is rapidly accelerating the way we work. Many businesses, team members, and organizations will now have to rely on remote work for the majority of their employee communications. As a result, you can expect video tools to see a massive surge over this time. 

One of the best (and definitely unique) options for managing remote staff is always-on video. In this article, we will explore this technology. We will examine what it is, the pros and cons, how to use it, and quickly review the best tools on the market. So let us get started. 

Tip – When you have this solution setup be sure to start off on the right foot with some ice breakers for remote teams.

What is Always on Video for Remote Teams?

One of the major downsides of video for remote teams is the hassle involved in setting it up every time. Making sure everyone in your virtual team is at their computer, making sure everyone logs in, connecting, you get the idea. With always-on video, you have exactly that, a video portal that is always turned on and ready to use. 

This may take a variety of forms, but often it is situated in an area of a room that someone can go up to and instantly connect with their team. Because it is already switched on, they simply need to press a button and they will be connected with the team. This allows a level of integration similar to that of an office. 

Always-on video takes different forms as well. You can add extra levels of reachability and availability, depending on what works for you. You can choose to have the software “on” but to require people to notify others when they want to talk. Alternatively, you can have the cameras and communication devices on at all times, similar to a real office. Additionally, you can choose how many people are involved in the video conference at all times, from everyone at once, to one-on-one meetings. 

Benefits to Always on Video

The benefits to always-on video collaboration are quite robust. They encompass the benefits of normal video conferencing, but have the extra benefits of extra-connectivity. 

Firstly, let’s talk about video conferencing benefits. When you’re working with remote teams, there is nothing like meeting face-to-face. Sometimes, you need that extra level of human interaction in order to really get things done. This accomplishes something that email or even the phone cannot. Video conferencing adds that extra level of social interaction and interconnectivity that people need to stay connected. 

It is also great for productivity. There is nothing like sorting things out with a conversation. A back-and-forth with email can take forever. With a video conference, you can quickly sort out your issues and have people on similar pages. 

Next is organization. Things can quickly become separated when people are working remotely. Keeping everyone in the loop is crucial, and you need to be able to stay in contact with people to make this possible. People can understand their tasks, deadlines, as well as how others are contributing. 

Always-on video provides even more benefits that simple video conferencing does not. By having the software always on, the problems associated with sorting out connections, logging in, and time of meetings is not an issue. Since everyone is committed to being fully reachable through the always-on software, you can quickly drop in and out with any questions or concerns you may have. 

Overall, always-on is simply a more interactive and connected version of video conferencing, and probably more so than any form of remote communication. If you are looking for the ultimate integration for monitoring or organizing your remote business, then always-on video tool may do the trick. 

Downside to Always on Video

Of course, no evaluation would be complete without also examining the drawbacks of a certain technology. In this case, the drawbacks of always-on technology are mostly that which are akin to remote work in general. Sometimes, it is simply not a substitute for in-person communication. 

However, when you don’t really have an option, you have to make do with what you can get. It is tough in times where meeting in person isn’t practical, but luckily people tend to get more and more accustomed to these technologies over time. 

In terms of always-on video specifically, there is often the hurdle that people simply don’t like to be connected at all times. They may feel it represents a lack of privacy or a lack of trust from management that they will get their work done.

This is why it is so important to set up a system that you and your employees are both comfortable with. You need a process that works for everyone. Everyone should understand that the system is simply for sharing information, and not as a means of “spying” on employees. The whole process should be built on a foundation of trust, with the communicated goal of having everyone work together toward a common objective.  

Alternative – Scheduled daily standup / status meetings on video

Always-on video conferencing might be a good option for you, but it also might not. Depending on your team and the type of work you do, you might be comfortable with an alternative arrangement. You should weigh your options, and also talk it out with your team if necessary. Remember, the goal of this is to have everyone communicating effectively, and to do this everyone needs to be comfortable. 

One alternative is a scheduled daily video call. By having it scheduled, people don’t have to worry so much about dropping everything and doing it. It won’t be an interruption, but rather a planned part of their day. You can structure these meetings so everyone knows what to expect. It’s a great time to catch up on objectives, works in process, and talk about future goals. 

Finding the method that works best for you is key. 

4 Best Always-On Video Tools

You might be thinking that this sounds great, but what technologies can you use to put this in action? In this section, we’ll outline our top choices of always-on video software. Technically, most video-conferencing softwares have an always-on option. It is just a matter of how you set up your portal. For always-on, you will simply leave one of these programs running, and allow people to jump in when they want. 


No list of video conferencing platforms would be complete without the most obvious – Skype. Skype gained its popularity by being innovative, but it kept its popularity by adjusting and keeping up with the market. With Skype, you have the major bonus that most of your employees have probably used this program before. 

Skype supports group video calling for up to 50 people, and even more if you have a paid subscription for a business account. No matter how you want to structure your video conferencing, there is probably an option on Skype. There are even screen sharing options for when you have to show people what you have been working on. 


GoToMeeting is a paid service, but often you have to make an investment if you want that extra functionality. GoToMeeting simply offers some usability that other programs do not. 

With GoToMeeting, you get everything you’d expect with something like Skype, but most features are a bit more fleshed out. There are plugins to integrate various programs (Salesforce, Google Calendar, Office 365). There are many advanced features so that you can set up your meeting exactly how you want, and include whoever you want.  


Probably the second most popular option on this list, most of your employees will probably have used Zoom before. Zoom is great because it is another free software, but has all the features you would expect from a more sophisticated program. It includes up to 100 participants at once, which is a big bonus if you have a large office. 

There are a wealth of features to make your experience more seamless, such as screen-sharing, whiteboard sharing, instant messaging chat, and annotations. Zoom also offers heavy encryption options, so you don’t have to worry about your team collaboration meetings being secure. 

Google Hangouts

Google Hangouts is a great video conferencing tool, but don’t expect the wealth of features to be had with some of the options above, especially if you opt for the paid version of any of these software’s. However, if you simply need to have a conference with a small team, Google Hangouts could get the job done. It is easy, intuitive, and free, and sometimes that is all you need. 


It really depends on evaluating your needs when considering any of these options. You need to know what kind of software you actually need, because there is a chance you will be paying for features that you don’t actually use. 

So before you begin this search, take some time to sit down and evaluate your needs. By this, we don’t mean what kind of video conference software you need, but how you actually intend on communicating with your remote employees to keep them organized and motivated. Once you know what you actually need, you can easily plan out a software that matches these needs. Your decision becomes simplified, and your system of managing your employees becomes much easier. 

Frequently Asked Questions (FAQ)

Q: How many people need to be involved in your remote meeting?

A: It really depends on who the necessary personnel is for the meeting in question. Unless you are setting up a company-wide meeting to address a large matter or go over specific policies with everyone, then always be sure to include only the necessary people in your video meetings in order to keep it efficient and communication clear. 

Q: How not to fail with transitioning to remote in 2020? 

A: Communication and clear procedures are two of the most important factors with remote work. Whether or not your team has experience with remote work, making sure you have consistent and clear communication (such as a scheduled daily standup meeting) with them will lead to a successful and effective team. 

Q: What challenges have you encountered building a remote team?

A: The main challenges have been communication and tracking work. Both of these are easily solved through tools like always on video and cloud storage for files such as Google Drive. 

Q: Where do you store all of your files, and make sure the entire remote team have access to them?

A: Almost any cloud storage software will work, however Google Drive offers some great online storage, making it accessible to anyone who needs to view it, and is easy to use due to it’s integration with G-suite. 

Q: How else do you ensure your remote team is engaged, challenged and successful?

A: Keeping everyone up-to-date with daily updates and weekly meetings are two of the best ways to ensure everyone is engaged. A weekly meeting with an always on video software allows your team to have something they own and can communicate to you on a weekly basis which helps you stay in the loop with what they’re doing and keeps them feeling responsible for their own tasks.

Q: What advice would you give to a team considering to go remote?

A: Ensure you have all the proper software’s and tools in place, such as always on video and a cloud-based file sharing system, like Google Drive. Then make sure to create and share the procedures to using these with your entire team. After that, implement strict policies for communication and schedule daily and weekly meetings with everyone.

For a complete list of our SOPs on how to work remote have a look at this guide to managing a remote team.

How to Manage Staff Remotely and our 7 Essential Collaboration Tools

Whether you are looking for a solution on how to manage staff remotely for the first time or looking to improve your current systems, this procedure will help show you what has worked and what hasn’t worked. 

Recently due to the Coronavirus, and for obvious reason, I have had some “real world” entrepreneurs ask me questions about how to best manage their staff as they begin working remotely to do their part with social distancing. 

My hope is that I can help contribute to the current situation by essentially open-sourcing all of our procedures for effective remote work. 

My team has been managing 50-100+ full-time employees, part-time employees, and contract team members working remotely for years. We have had some incredible system failures (theft) and also some huge wins (getting invited to a team members wedding in Bangladesh) with managing remote staff. Overall, we have managed almost 200k hours of remote workers on one platform alone: UpWork.  

  • 172k hours managed
  • 2398 people hired
  • 91 active remote workers
  • Over $1M Spent

This has all been done through working remotely on one platform. Here are all of our systems to help you get set up to be effective with remote workers!


In this article, I’m going to lay out how we work by breaking it down into 3 parts. 

ONE – Tools: What tools are needed or optional to manage remote workers efficiently and increase productivity.

TWO – Setup: How do you get remote workers setup and excited about the system

THREE – Ongoing Communication Cadence: A system is useless if it isn’t used

I picture this being the most useful for a manager/leader that is taking a semi-remote team of 3-15, that work off of a laptop, communicates via email, typically sitting beside one another, to… a fully remote team, no longer in the office. If a more helpful guide surfaces, I will be sure to try and reference it for additional reading. 

LinkedIn Remote Work Training – Made Available for Free

Please feel free to share and comment so we can try to help as many virtual teams get over the hurdle of remote work. 

For a couple other useful articles on the topic checkout…

Icebreakers for Remote Teams

Always on Video Options Reviewed

ONE – Essential Tools for Remote Staff

These are the tools we use. 

NOTE – Many of these tools have made special pricing accommodation during the coronavirus pandemic to help facilitate remote work.

Security & Password Sharing:




Time Tracking:

Other (used on specific projects)

TWO – Setup To Manage Staff Remotely 

This can be the most daunting part of getting remote staff working and managing them effectively, especially if your staff is located within different time zones. 

I will do my best to recommend the sequence of getting things set up so it doesn’t disrupt your company culture. 

Change Management Warning: Managing this much change for someone can be challenging, so below will outline the order of adoption that I would recommend. 

Setup Part A – How We Use Slack – Our Slack Setup Procedure

Getting setup on Slack or a similar team chat solution is a great first step. 

BUT, if you don’t plan or put some thought into the onboarding process, then it can turn into chaos. 

Below is the email I sent to the team to communicate how we are going to transition to and start using Slack. In the end, the transition was successful and people really took to it vs a standard email. 

Hi Team

Slack will become the new standard team internal communication tool – late to the party but now is the right time. 

Objective – Streamline communication across all people and all projects in the organization resulting in improved productivity, communication and culture. 

Good References:

Case for Action – As we have more people overlapping between projects and working remote, it becomes more important for us to have standard methods of communication. On any day I might communicate with people using… email (one of 3 different logins), telegram, in person, google chat, skype and text msg. This is a problem with others as well working on multiple projects. Slack will not completely fix the problem but will help. 

Actions Items for All:

  1. Install slack on your computer and phone
  2. Join the channels you have been invited to
  3. Say hi and drop a gif in a channel you have been added to 

What is Slack?

Slack is made up of channels and is essentially a group chat. 

How Will We Use Slack?

I have created a table below with input from many of the managers on…

  1. #Name of the Channel – the channels we will have on launch
  2. Purpose – How we will plan to use the channel
  3. Owner – Who is responsible for that channel being used as intended
  4. Users – Who will be in the slack channel

As with all things this will take some initial uncomfortable work as we break old habits.

1DailyDaily – 3 sentence update – done yesterday, plan for the day and any issuesJonCore Team – In House Employees & Critical Few Support
2Random Fun Lots of GIFsNarcisIn House Employees
Project 1 – admin team
Project 1 Manager
Project 1 – operations team
Project 1 Manager
Project 2


Slack Tips:

  • Before you send an email, text, telegram message… think – Can this be done on Slack?
    • See the tips below on when to use Slack
  • Set slack to open automatically on your computer
  • If you want a new channel to send a message to Jon requesting it and why
  • Great gifs can be found at make sure to do the Giphy integration so that you can easily insert a GIF with the shortcode “/giphy keyword”

Slack vs Email vs Meeting:

Reference –

When to Slack:

  • If you need a quick answer on something simple
  • If you want to share & collaborate on something in real-time
  • If you need an immediate response
  • If you want to share something random, funny or off-topic

When to Email:

  • You need to include someone external on the conversation
  • You’re sharing something longer with lots of detail
  • You’re sharing something pretty important and want to underscore that importance
  • Something more private then what you want everyone on the slack channel to see

When to Meet:

  • You need to discuss a sensitive issues
  • You need to talk through complicated projects or subjects where people are likely to get confused
  • You’ve been discussing via Slack or email and the discussion has dragged on with no clear next steps or consensus
  • Brainstorming ideas
  • Structured Team Meetings:
    • Weekly 1:1
    • Weekly Business Meeting
    • Monthly/Quarterly Review/Strategy or OkR Meetings

When to do None: (most of these are for me)

  • Asking about a task that isn’t overdue and is correctly assigned by whatever method that business is using (ie weekly sheet)
  • Friday at 11:00pm asking for an answer in under 24hrs unless there is a fire
  • Asking a question whose answer is easy to find on Google.

Now that you have your backbone of asynchronous communication setup for your remote team it is time to move onto the next step. 

Setup Part B – Security & Password Management

Setting up your remote work security policy is important, however you may not have one and creating a robust policy from scratch will require too much time and effort before you need it. Below, I’ll go over all the essentials in order to implement solid password management for remote workers.

Here are the basics …

Part B-1 – Setup Password Manager

With a remote team, you will need to share login and access information. If you have ever emailed a password, entered into a spreadsheet or shared one through online chat, you are doing it wrong! 

There are a couple of great options out there. We have found 2 that lead to the highest productivity and effectively priced:

  • One Password – Fully featured password manager with lots of ability to restrict team members from seeing passwords, logins, etc..  
  • Team Password – Less expensive and a great option for sharing less critical passwords with a larger number of team members. 

Once you have signed up decide on the vault structure and who will have access to specific logins.

Here is an example table to create before you sign up. 

Vault NamePurpose of VaultWho To Provide Access To
Project 1 – FinanceAccess to payment processing and bank accountsOwner, Controller/Bookkeeper
Project 1 – AdminAccess to logins required to control administrative accountsOwner, Manager
Project 1 – TeamAccess to the logins required for each teamOwner, Manager, Team Members
Team Member NameAccess to any critical accountsOwner, Manager, Team Member(s)

If this structure is followed, then the login for any team member is fully controllable by the Manager and you will never find yourself in a situation where access to a login is unavailable causing the business to grind to a halt. 

TIP – Even if you don’t think you need it make a vault for the person so they have someone to put a misc login that isn’t their personal vault (we don’t want anyone using their personal vault). 

Part B-2 – Security Best Practises

Like any tool, applying strict guidelines and discipline around it always makes it stronger.

Below is our 12 step password and security check. 

  1. Are ALL work-related passwords stored in 1password?
  2. Are passwords randomly generated (i.e. high strength)?
  3. Is your 1password Emergency Kit saved on your computer?
  4. Is your 1password Emergency Kit saved on a back-up (external) device?
  5. Have you turned off your “auto save password” switch on all internet browsers?
  6. Are any work-related passwords saved on your internet browsers?
  7. Are any work-related passwords saved on your computer?
  8. Are Google Drive documents shared with anyone outside company team members? If so, who?
  9. Do you have a procedure for cold/backup storage?
  10. Do you have a VPN on your computer? If so, is it on during work hours?
  11. Are any personal logins or passwords saved to 1password?
  12. Do you ever use your laptop and/or phone on public wi-fi? (Rule of thumb: never login to public wi-fi. Either use a hotspot, VPN, or don’t go online.)

Part B-3 – Assign “Security Auditor” to do a monthly audit

We have an internal security auditor who does a monthly check with all team members and remote workers (who have access to passwords) to confirm we are following our internal remote work security policy. 

Here is an example of our verification process for the security audit:

Download a Copy

Setup Part C – Time Tracking

There are 2 main systems to use for time tracking. The first is:

UpWork – If we hire someone on Upwork (which as mentioned above we do A LOT), we leverage the platforms built-in tools.

Clockify – This is a FANTASTIC freemium tool whose functionality for this free model is sufficient. There are paid alternatives like Timedoctor, but after using both I see no reason to not use the free Clockify option (at least in our case). This may vary depending on your needs. 

Get started with Clockify

  1. Decide on your structure: this will likely be similar to how you have 1Password set up. For us, we have everyone on the same team and then allocate their time to different projects. Look at the “getting started” articles shared by Clockify
    1. Introduction to Clockify
    2. Onboarding checklist
    3. How to track billable time
    4. How to track time with a team
    5. How to track project profitability
    6. How to track team productivity
  2. Sign up here (free)
  3. Invite team members
  4. Create projects
  5. Assign team members to projects
  6. Confirm your controller/bookkeeper has access 

Setup Part D – Documents, Files & E-Signing

How you manage access to the documents and files people need to work will be very much unique to each company.

Most companies will need to decide between: 

  • Remote Access – Ctirix
  • Cloud-Based Microsoft Office Documents – Dropbox or Microsoft Offerings
  • Full Cloud-Based – Google Drive 

Whatever is the lowest pain point of change is likely the best option for your situation. 

For us, we are 99% Google Drive/Gsuite, with some documents (typically larger Excel files) shared via DropBox. 

If you haven’t made the move to Google Drive and its free options, then now might be a great time to make the change. 

Document Signing for Remote Workers

When dealing with remote employees, document signing is something that is obviously more challenging because people are not located in the same area. 

We have used a few different solutions, but landed on PandaDoc as being by far our favourite. 

The ability to have templates, users and rules makes this a very easy solution. 

Many other businesses that require proposals to be sent and signed will likely want to look at Proposify or the other one we use, Qwilr.

Setup Part E – Meetings

A LOT of buzz has occurred around video conferencing and certainly, this increase has been warranted and makes sense in today’s technology and remote workforce.

However, there are many solid and (mostly) free options out there. 

  • Zoom – Getting an unreasonable amount of love right now in my opinion… it is fine but don’t see how/why it is so much better than other less expensive options
  • Skype – An original chat/video platform that is used by many
  • Google Hangouts – A great option for anyone using Gmail or GSuite

Like anything, it is best if you can pick one and decide that is your go-to for the team. Jumping from one platform to another can get confusing and messy, not to mention it can make your team look unprofessional to clients. 

Which Video Conferencing Solution is Right for your Team?

If it is just your team and you know who you will be speaking with, then Skype is one of the best options. On the other hand, if you need to do conferences with other tech-savvy people then Google Hangouts is a great option. Finally, if you require a little more robust solution with access to specific controls, etc then Zoom is better. 

Here is a comparison of solutions for always on video for remote teams.

PART 3 – Effective Remote Staff Communication and Collaboration

If you don’t yet have a meeting cadence, I highly recommend you decide on one now to provide structure to your remote workers. 

All the tools above are useless unless there is a system around how to use them to manage staff.

This typically revolves around a series of meetings each with a specific objective. Our system is based off of several great books, including Traction, anything Scrum/Kanban/Agile and the OkR goal-setting framework.  

Based on the books above, here is the basic structure of meetings for our teams (which are currently 100% virtual):

Daily Standup Meeting or Update for Remote Teams

Also referred to as an all-hands meeting, this should be either on a video conference call or the Slack daily channel. The update should quickly cover 3 things for each person.

  • What was done yesterday?
  • What is the plan for today?
  • Are their any issues preventing you from completing your daily tasks?

Make it snappy and take any issues offline to resolve them 1 on 1.

Weekly One-on-one Meetings with each Staff Member:

Of all the meetings this is by far the most important! 

Any staff/company alignment failure can typically be traced back to a root cause of not having a good enough weekly one-on-one meetings that flagged the issue early enough to be addressed. 

The weekly one-on-one meetings follows this agenda:

  • Biggest win – What was the staff members biggest work win over the last week? 
  • Issues, Questions and Concerns – Is there anything they need to discuss, such as pay, HR, team issues etc. Non-work but workplace issues can go here to ensure they don’t gather energy in the dark. 
  • Training – Progress and discussion against any training initiative. For instance, a book, topic or Udemy course. 
  • KPI’s – List of the KPIs they are responsible for and the results. Typically no more than 5 at a time.
  • Summary of what was done last week and the plan for next week – Same as the weekly business meeting but not in as much detail.
  • Tracking of any special assignments – If it is not on the weekly then they are not responsible for it. Since we tend to drop a lot of different tasks on staff, this is where it should always get caught. 
  • Hours worked review (if hourly) – Link to Calendly and the number of hours worked that week.
  • Feedback – NOT ANNUAL but weekly coaching opportunities with some quick improvement feedback. This is not always easy so here are some helpful tips. Ideally, this is always constructive, but if an issue needs to be addressed, then it is done here. 
  • Tasks for the manager to do – What does the staff member need their manager to do to ensure that they can complete their work/tasks? It gets listed here. It’s obviously important to set the tone that work on the weekly gets crushed so your team members aren’t delaying tasks. 

As with almost everything, this lives in a Google Sheet (you can also use Google Docs, but Sheets is much easier to organize) and a column is inserted each week so that the most recent week is right beside the first column. Tasks can be added to the projects Trello board during weekly meetings. 

It’s important that the staff member completes the sheet before the meeting in order for all 1:1’s to be done effectively and quickly.  Each meeting should take 15 – 30 minutes. 

As my staff like to say only an engineer would create a spreadsheet and consider it an aid for human interaction. But everyone that has bought into the system has either immediately or come to really appreciate the structure and clarity this meeting provides. 

Part of the magic of the daily and weekly meetings is they dramatically cut down on all the important, but time-consuming logistical questions that can pop up as a manager. By collecting and responding to issues and tasks during the weekly, you will avoid getting bogged down with menial questions multiple times a day. 

Weekly Business Scorecard Meeting:

This meeting is very metrics-driven, with a review of a kanban to-do list that lives in Trello. 

Agenda (varies for each business):

  • Mission/Vision/Values recap – 2 minutes
  • OkR Reading (equivalent to rocks for the Traction fans) – 2 minutes
  • Sales & Operations Scorecard –  revenue, calls, output outstanding etc, PnL review, cash flow requirements, etc
  • Marketing Scorecard – posts, social media, podcasts etc complete
  • TO-DO List that is on a Trello kanban board prioritized into 4 columns with each to-do assigned to someone with a deadline. This has been a significant upgrade from a to-do list that can seem to grow infinitely and doesn’t help prioritize the immediate tasks people are responsible for during the week. Additionally, moving the card from to-do to done in the weekly meeting is fun! The result is the entire team has 52 sprints in the year to do things that help grow the business.
    • Backlog – Great idea… but don’t have time right now (add it into the backlog)
    • To Do This Week – Add in your to-do’s what you are going to get done for the project this week (this is your sprint) 
    • Done – Move the cards you completed this week into this column
    • Completed/Archived – Once a task is done for 1 week it gets moved to the completed/archived column 

Here is a great guide for a different take on this meeting –

Monthly Performance & Quarterly Goal Setting

This meeting is mostly focused on two things:

  1. PnL Review for Last Month – If we are doing the weekly correctly, there shouldn’t be any surprises. 
  2. OkR Goal Progress Review – This is where people will identify if they are at risk of achieving their OkR and additional resources will be brought in to help if needed. 

The books Traction and Measure What Matters both go over this meeting in great detail. 

At the quarterly meeting we do a review of the successes of the previous quarters OkR’s and then set the next quarters. 


As managers struggle with team members going remote we will all need to find ways to adapt. 

My hope is that by essentially open sourcing how we manage staff remotely companies will be able to be just a little more efficient. 

If there are additional guides you think I should be including here please let me know. 

Good Reading:

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