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Managing Remote Teams


Remote work is getting quite a bit of spotlight lately. And it’s no wonder. There has been significant pushback in the remote-work movement for years. In the interview with Jason Fried, co-founder and CEO of Basecamp, 99u asked him how to help managers overcome this fear. 

“Some managers may wonder how you know work is getting done if you can’t see people. The only way to see if work is getting done is to look at the work.”

Jason Fried

Managing remote teams isn’t for the faint of heart. It takes courage – courage of vulnerability, courage to trust, and follow-up in accountability. The only way to really conquer uncomfortable situations is to face them. 

Let’s talk about what it takes to be a manager of a distributed team and an employee in a distributed team. I’ve reached out to some of my peers and colleagues in the distributed and remote work tech space for their advice as well. 

Trust but Verify

Trust is a vital factor in any type of work – remote work is no different. From the perspective of an employee turned freelancer, trust is a two-way street. I used to have a boss who watched my screen on Remote Desktop even though I was doing twice the work. It felt like betrayal. 

At the same time, not everyone has my kind of work ethic. Trust is a difficult thing to manage. It’s a lot like a secured credit card. The bank trusts you, you trust the bank. As communication grows and deadlines are met, both parties trust each other. 

If you over-verify you can be perceived as a micromanager which is bad for morale. If you are a micromanager it can affect efficiency and contribute to employee attrition. If this becomes a pattern in your hiring process there are one of two things that are likely causes: 1) you aren’t the right person to hire; or 2) you aren’t the right person to train. So there are pros and cons to both. 


Accountability is a normal part of life. Being accountable doesn’t mean we have to engage in hand-holding or babysitting. Viewing it that way is the wrong perspective. It’s your responsibility as a manager to oversee and provide guidance. 

Accountability can come in a few different forms. If you’re paying an hourly wage, then accountability is likely tied to a timesheet. The priority ends up being perceived by employees as “well, I’m here.” When work isn’t acknowledged or employees don’t have room to grow, apathy can be the result. Apathy is the antithesis of productivity. Ultimately apathy will increase employee dis-satisfaction, manager stress, and attrition. 

Another form of accountability is deliverables. A streamlined system of project management (and tool of your choice) with clear goals and delineated scope is the path to success. One of the things that impressed me while working at the advertising agency is that my accountability was tied to my deliverables. I had realistic due dates, clear guidelines, and was appropriately recognized for the quality of my work. Though I was on salary, being accountable for “my work” instead of “my time” was the right environment for me. I saw this as the opportunity to excel. I was proud of my promotion from Marketing Manager to Director of Marketing. 

Knowing what motivates your team is a huge factor in accountability. Some employees want to be recognized in front of their peers, others want bonuses or raises. Still more prefer freedom or work challenges.

One-on-One Conversations 

Team members are people. When you parent or teach children, you quickly become aware of what motivates one child and not the other. It’s no different in teams – remote, in-house, or distributed. Holding regular one-on-one conversations with each member of your team is a great way to gain insight into your company’s culture, their strengths and weaknesses, and potential.  

This type of communication establishes an open door policy that works. Many introverted people are intimidated about “going to the boss”, especially if they’re struggling with imposter syndrome. Being proactive as a manager means going to your team first. 

Straight from the Boss’ Desk

We love reaching out to our community. Here is some advice from our well-loved friends and peers on managing remote teams. We’d love to hear what helps you, too!

“Learn to see the people you thought you can’t see, and to be close to people who are far away, and the most incredible world is suddenly inside your home and head.”
Andrea Breanna

“Accountability is all about having a solid process of communication, forecasting and tracking. If that’s in place you’ll have successful projects no matter if you’re working from your kitchen or in your office cube. What you can’t do in this moment is put your head in the sand and hope it all just works out. Now’s the time for proactive communication and clarity with your team and clients / customers.”
Kori Ashton

“Trust. Invest in your employees well-being, be decent, and promote a culture of accountability. If you do these things properly then you don’t need to micromanage. Measuring outcomes vs. production becomes the norm.”
Joshua Strebel

“We have a daily slack standup channel (we call it #magicminute. Every morning we check-in with three things. 

1. Emotional check-in. How are you feeling? What are you struggling with? Anything we can do to help? 

2. One accomplishable task. What is your top priority today? The one thing you need to get done to feel like you have forward momentum. We used to do a list of three things- but right now it’s too much and gets overwhelming. So right now we just do one. 

3. What did you do yesterday? Did you accomplish the one thing? Why or why not? How can we work together to help? 

This helps us track not just our emotions, but also our overall progress. We use Asana to track projects overall, but this method helps us see that we’re taking steps every day and while one day might not be a productive as the rest- on an overall schedule we’re moving forward. 

But I think this boils down to recognizing this isn’t a normal working from home situation. This is working from home during a pandemic. Work will be different. Output will be different.

I think (as usual) the best way to adjust is by being human and empathetic. Recognize that this is hard for everyone and that business will be different for a minute. It’s easy to get stressed and try to overcompensate. Allow yourself and your employees to breathe and make the emotional adjustments they need.

When you lead by example you’ll have better results. You can’t pretend like everything is fine and nothing has changed and be the stoic leader while expecting your employees to be vulnerable.”
Amber Pechin

“While everyone on our team works from home occasionally, we do have a physical office that we are really missing right now. Usually, we have everybody in the office more days than not. So, while the remote working and technology aspect was easy to adapt to, the community aspect has been hard. Especially for me, as a hard extrovert. 

We have been super understanding of people’s schedules. A lot of us have kids and it is hard. Less expectations on turnaround. We have been using Slack to streamline communication for years. We have a daily stand-up in place that every team member takes part in. Basic stuff. Dash what’s interesting in your life? What did you accomplish yesterday? What are you working on today? What are your obstacles? 

Over the past few weeks, I have been mixing it up by inserting little contests into our daily stand-up to build community. The other week, it was riddles! The winner received dinner delivered for their family via DoorDash. Last week, it was a quiz about things in the office that we all miss. I sent out a little prizes from Amazon Prime to the winner and runners-up. 

Making it more about the people, and less about the work, is the key to getting through a difficult time like this. We’re all going to come out at the end of this tunnel. And the people who feel like they are supported are going to contribute more. This has been very hard for me personally. I can only wish the best for everyone else trying to keep a business running during this time.”
Jessi Gurr

“The key for us is to set clear objectives, goals, and milestones. I don’t care how much/little/when/where people work. My encouragement is to find what works best for that individual and then work towards the objectives. If the objectives are met, everyone will be thrilled. If they aren’t, we examine what might have gone wrong, re-calibrate, set new objectives, and try again. In some ways accountability in a distributed or remote culture is a system that requires regular calibration. Once you find the right input, the output takes care of itself.”
James Laws

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