June 4, 2019

Remote Work Playbook

(aka how to get your team started with remote work)

A friend who runs a couple of businesses in Lagos, Nigeria recently asked me to document a guide on how to introduce remote work to his team and I wrote this up. They found it helpful so I thought I might as well share it with y’all as this applies to any business out there who is curious about remote work.

This guide aims to document how to get started with introducing a remote first culture into your company based on my experience running and working in remote teams in the last 4 years.

Why should you give remote work a try? If you’re not convinced of the fact that remote work and having a distributed team is the future, please read this book Remote: Office Not Required and buy it for your employees and managers.

Okay, so you’re sold on remote work, you’ve read up on it but you’re not sure how to get started?

Here are some strategies and tools that have made working remotely work for me and the companies I’ve worked with.

Accountability - you need a rock-solid process

The number one concern managers have with remote work is - how do you trust that the employees will do any work while away from your physical office? At least when they are in the office, you can see/monitor what an employee is doing.

This is a valid concern so I’m going to start by saying that remote work hinges on trust between employees and managers.

Why do you have employees you can’t trust?

Also, if you’re not sure how you’ll maintain accountability for your remote teams, consider this: how do you keep your teams accountable now?

If you think it’s by seeing the tops of their heads sticking up out of their cubicles, you may need to reconsider more than your policy on remote work. In the end, you have to be able to measure the results - the output of what you and your employees do, and not just the input in the form of hours spent in a certain chair.

Here are some ideas on how to create a rock solid process on accountability:

  • Have clear quarterly OKRs and KPIs: These must be documented and further broken down into tasks in a project management tool for each department and members of the team. As a manager, there should be one central place where you can track every project and tasks that each member of your team is working on at a glance. The responsibility for who documents a task should fall on the task owner and the line manager.

  • Daily stand-ups: This is common in the software development world and I think this can be made to work in other fields. The process involves every member of the team (including the manager) giving an update on the day. Some teams run it first thing in the morning to give an update on the previous day and set the tone for the current day. While some run it at the end of a workday. Each team member quickly provides answers to these 3 questions in relation to the tasks they’ve been assigned:

    • What went well?
    • What didn’t go well?
    • What are the blockers?

This provides accountability so that everyone is in the loop on what each member of the team is working on and there are no surprises at the end of the week. If there are any blockers, a member of the team can chime in to suggest a fix. Any conversation that spans more than 5 mins can be discussed in another meeting with the parties involved. A stand up should typically take between 30 - 45 mins based on the size of the team.

  • One-on-ones: This is a scheduled and recurring bi-weekly one on one meeting between an employee and a manager. The ideal goal of this is for a manager to check on the pulse of each member of the team on a professional and personal level. Check this out for a detailed how-to guide on one-on-ones. Whether you’re remote or not, introducing one-on-ones can be great for the culture of the company. I’ve been on both sides and I’ve found 1:1 super helpful as an individual contributor and as a manager.

  • Peer one-on-ones: This involves creating a system that matches 2 of your employees randomly to have a chat and get to know each other better. The idea is to get every member of your team to meet and foster engagement among your workforce. I will recommend that this must be implemented if it’s a fully remote company. Otherwise, your employees in different department might not get to interact with each other. This fixes the problem where your employees only interact about work - organising peer one-on-ones create an opportunity for them to get to know each other outside of day-to-day work.

  • Have a company-wide weekly update where each department including management and CEO give a 5 mins update on what happened this week. In my experience, this fosters a culture of accountability from the top. Each employee can see that everyone in the company including management is held accountable. No department wants to be seen as slacking, so there can be an overall productivity boost from this alone.

  • Performance Reviews: This isn’t unique to remote work. You should do this whether you’re remote or not.


Remote work requires good communication and process documentation to work so only people with strong written and verbal communication skills will excel at this.

This will take some time for teams that are new to working remotely, but to make remote work, your team (at all levels) need to be great at communicating clearly.

Here are my tips for documentation and communication:

  • Create the habit of documenting every task item. This should start from the top. As a manager, if you want a team member to work on a task, the first thing you should do is to create a card for it with all the details, then assign the respective team member to it. Ensure that updates and collaboration regarding that task happen in the comment section of the card or via an appropriate project/task specific communication channel.

  • As an individual contributor, is there something you just did that you think a colleague would have to do at some point in the future, would this have been easier and faster if you had a document to consult? If your answer to both questions is yes, write documentation for the thing and store in a common place where your team can access. Notion is a great place to store this. You should also share the link in your instant communication channel so your colleagues are aware.

  • As a manager, watch out for the questions that your team always ask you or their teammates. My rule of thumb is, if at least 2 - 3 people on your team have asked you about the how or why of something more than once, and the answer is almost always the same (or there are a few options based on certain conditions), that’s a candidate of a process that needs to be documented. So, the next time you’re asked, you can just forward a link to them.

  • Err on the side of over-communication:

    • When you have to communicate something to a colleague, manager or a client, aim for clarity and hold no assumptions. This means when you explain or document something, someone with no prior context should still be able to understand what you’re saying.

    • Sometimes, instant messaging and texting might not be enough. If we’re collaborating on something and I notice there’s been a few back and forth on the matter and we seem to be circling around something that’s not clear, I opt for a video or voice call.

    • At the end of a meeting, recap the action points verbally if it is a voice/video call. Do the same in a written note and in your shared project management tool if it’s about an ongoing project. If it’s about a new project and no card exists for it yet, create a card for it or ensure that someone else is doing that.


All of the processes and strategies I’ve explored above can feel a bit overwhelming but don’t be alarmed, there are tools that have been created specifically with a mix of these processes in mind.

From my experience, in addition to email, Google Calendar and Google Drive, facilitating and managing remote work would require a mix of tools that can handle the following:

  • Project management / to-do list – keep an updated list of what needs to be done by each member of the team.
  • Schedule - keep track of dates, milestones, events, and even vacation time.
  • Instant messaging – chatting and questions for collaboration
  • Wiki, docs and files – store and shares documents.
  • Automatic check-ins – ask recurring questions - one-on-ones, daily updates / weekly team updates, 360 review cycle etc.
  • Productivity tracking and monitoring*

Project management

There are multiple players in this section but you only have to pick one.

Basecamp: https://basecamp.com Project management and team communication software. This software can handle almost everything on the checklists above except productivity tracking and monitoring. So, if you go with Basecamp, you probably will not need Slack for communication.

Notion: Notion – The all-in-one workspace for your notes, tasks, wikis, and databases. “Write, plan, collaborate, and get organized - in one tool.” It can become the central source for everything related to your business - to do lists, projects board, process documentation, etc.

Trello: https://trello.com For project management and documentation: “Trello lets you work more collaboratively and get more done. Trello’s boards, lists, and cards enable you to organize and prioritize your projects in a fun, flexible way.”

Asana: https://asana.com/ For project management: “Asana is the work management platform teams use to stay focused on the goals, projects, and daily tasks that grow business.”


Slack: https://slack.com For collaboration - instant messaging and discussions. “Slack is a collaboration hub for work, no matter what work you do. It’s a place where conversations happen, decisions are made, and information is always at your fingertips. With Slack, your team is better connected.”

Tip: create project specific channels and some fun/watercooler channels

Zoom: https://zoom.us/ Voice and video conferencing - Zoom is the ultimate tool for meetings because not all meetings have to be physical meetings.

People Management

Lattice: https://lattice.com/ For managing one-to-ones and performance reviews.

Donut: Donut.com It’s a Slack bot for creating an automated 1:1 matching roulette program instantly for your Slack team. This will help with organising peer one-on-one meetings.

Productivity Tracking Tools (Monitoring and Reporting)*

This is a tricky one. If you hire responsible adults with good work ethics and you trust them, I don’t think this is compulsory.

In all the companies I’ve worked at remotely, no one has made me install a monitoring and tracking tool and I have found no need to install in the team I’ve run.

However, I am aware that some companies enforce some time tracking software rules, especially for freelancers.

If you feel that you need to, one of these tools can be installed on official laptops with email reporting sent out to daily or weekly to the line managers.

Rescue Time: https://www.rescuetime.com/ An analytics service that shows you how you spend your time and provides tools to help you be more productive.

Because I’m a productivity data junkie, I personally use this tool to get insights into how I manage my time. I like the weekly summary email I get that shows me how many hours I worked in the week, and out of that, how many was spent doing my core task (which is software development), how much of my time was spent using distracting and entertainment applications, etc.

HubStaff: Hubstaff | Time Tracking Software for Productive Teams Employee work time tracker with screenshots, timesheets, & more. Helps you understand productivity issues and make data-driven decisions. I find this a little invasive because it takes screenshots but some managers love it for this very reason.

Not everyone and every job can be remote

Lastly, now that you have a process for accountability and you’re working on improving communication and documentation processes at your company, it’s also important to note that not every personality is best suited for remote work.

The personality that thrives at remote work: Are they independent, self-starting, entrepreneurial, and disciplined? Do they have basic digital skills? Do they have a bias for action? Do they have strong clear communication (written and spoken) skills? Are they good at, and do they enjoy, using technology to stay engaged with their teammates?

These are the questions you should aim to answer during your interview process.

Some people might check all these boxes and still might not want to work remotely and that’s okay. Remote work isn’t for everyone.

It also goes without saying that not every job can be done remotely. A way I’ve seen this measured is: if what an employee does is already 50%+ online, that job can be done remotely.

So what’s next?

  • Read the book recommended above first if you haven’t yet
  • Introduce the accountability processes
  • Start small - introduce a pilot phase of an optional work from home 1-day a week policy.
  • During this testing phase, ensure the employees working remotely are properly engaged and not second class citizens. Integrate them into everything that’s happening at the office.
  • Monitor and evaluate productivity and the impact of the newly introduced remote work on your team culture.
  • Keep evaluating and iterating on the process and tools until you find a good fit that works for your business and your employees.

If you have specific questions, I’m happy to have a chat and help with a walkthrough of any of the tools and processes.