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Remotely Operated: Managing Scattered Teams



Anjuan Simmons provides guidance for how managers can support remote teams and help them improve performance.


Anjuan Simmons is a technologist with a successful track record of delivering technology solutions from the user interface to the database. He combines his experiences working at Big 4 management consulting companies as well as small technology startups to implement practical solutions that can be understood and scaled across organizations.

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Simmons: My talk is titled, "Remotely Operated: Managing Scattered Teams." My name is Anjuan Simmons. I'm an engineering coach at Help Scout. I manage two software development teams at Help Scout. We're a fully remote company. In fact, Help Scout has been fully remote for all 10 years of its existence. I have software engineers across multiple time zones, stretching from Vancouver in Canada, to A Coruña in Spain. I've learned a lot about managing remote teams, and I'm excited about sharing those learnings with you. After all, we're living in a new era, which requires a lot from those who manage software development teams.

The New Era of Scattered Teams: Remote-First vs. Remote-Forced

We're in the era of scattered teams, while remote are distributed, or often used to talk about teams that don't work in the same physical location, I don't think those terms accurately describe our current reality. They're just a little too neat. These teams aren't distributed. They're not really remote. They're scattered. Also, something that doesn't get talked about enough is the fact that there are two types of remote work companies. The first type are remote-first companies like Help Scout, who have had the time to do the hard work of crafting a rich experience for their employees. The second type are what I call remote-forced. Meaning that they've been thrown into supporting remote employees. These remote-forced companies emerged in 2020, because of the COVID-19 pandemic. This tiny virus has radically changed work in ways that we've never seen before. Every industry has been touched by its spread. Nearly every company in the software development industry shut down their offices in early 2020, so that their employees could work from home and help contain the spread of the virus.

While remote-first companies experienced very little change, the remote-forced companies truly felt the stress of having their people scattered across the world. It was often up to individual employees to find a positive spin on the situation. In fact, many bought into the idea that working from home meant they could escape the noisy and interrupt heavy environments of offices and retreat to the Zen of their living spaces. The idea was that we could enjoy all of the creature comforts of home, while still getting things done. We could relax in our favorite spaces at home without worrying if someone would steal our lunch from the break room refrigerator. Also, there was no need to worry if our favorite tea was available in the break room because we fully controlled the kitchen in our homes. Also, we finally had a thermostat we could control and lived out our workday in our preferred room temperature. At least that was the idea.

However, the reality of remote work is that for many of us, we're not working from home, we're living at work. A large number of us had to manage new challenges, like raising children while managing all-day Zoom calls. In addition, some of us had partners who also had to work from home, which introduced new pressures on relationships. All of this was done while dealing with being forcibly physically separated from our work colleagues. Many people who operate in this scattered stance also deal with scattered thoughts and scattered emotions every day. I think that good remote management can make the difference between scattered teams thriving or failing. Working at Help Scout has provided me with the benefit of working at a company with a robust set of remote work policies.

I've been thinking of an analogy to describe what I've learned leading remote teams, and one emerged from one of my pandemic hobbies, and that's flying drones. This is a DJI Mavic Mini 2, and it's a lightweight drone that I bought a few months into the pandemic. I love flying it. As I've worked to increase my expertise controlling this drone, I realized that operating a drone, something designed to fly far away, but still be under my local management is similar to managing a remote team. Drones are designed to be remotely operated over large distances using a controller. In many ways, managers have to do a lot of the same things that drone pilots do. I'll use concepts from flying drones to describe how to effectively manage remote teams.

Self-Management - All Remote is Local

There are three general concepts I want to share with you. The first concept is, a good remote manager has to understand the importance of self-management. All remote is local. You can't control how the people you manage respond to working remotely, to how they respond to being scattered. They're going to have a wide variety of responses to the reality of working from home. However, you can control your response, and how you respond can go a long way towards helping your teams navigate being scattered. A key part of using a drone is the controller. This was the one from my DJI Mavic Mini 2. The controller totally operates the drone. Any issues with the controller will be immediately reflected in the behavior of the drone. If the controls that manage the drone's height, or direction, or speed malfunction, then you're quickly going to have an out of control drone that will not be able to do what it was designed to do. This is also true for managers with remote teams. If you experience errors in how you operate, then your team won't be able to benefit from your support.

Self-management is important if the team works where you work. It's also important if you are working with scattered teams. If the batteries in your remote control die, then you lose the ability to manage the drone. The same thing is true for remote managers. If you don't take care of yourself, then you lose the ability to take care of your team. That's why healthy teams need healthy managers. You have to do the work to take care of yourself. You have to get enough sleep. You have to manage your own stress responses. You have to stay hydrated and get enough exercise. The better your physical body operates, the better you'll be able to operate your team.

Second, you have to model the behavior you want your team to emulate. You have to model a healthy PTO, paid time off, and you have to schedule a few weeks off, or at least a few long weekends regularly on the calendar. If your team sees you taking vacation, then they will be empowered to take time off themselves. Also, if you're feeling stress, then you have to say, I'm feeling stressed out right now, I need to take a mental health day, or mental health half day. Again, the behaviors you model will be reflected in your team. If you take breaks to manage your mental health, your team will know it's ok to do it too.

Flying a drone in the United States means flying in a whole net of regulations that are controlled by the Federal Aviation Administration or FAA. It's vital for drone pilots to be in compliance with a support structure that controls what happens in the sky in which your drone is operated. The same things apply to remote teams, you have to make sure that you are maintaining air support. That means you have to stay in close contact with your management and with your leadership team. Your leadership team is trusting you to manage the team. If you show the ability to understand what leadership needs from the team, and if that is directly reflected in the outputs of the team, then you'll be better able to support and make sure the team is successful. I can summarize this concept this way. Self-care sets you up to be a better manager.

Communication - Strong Signals Cut through Noise

Let's go to our second concept for managing scattered teams, and that's communication. Strong signals cut through the noise. The entire reason why I can fly my drone and see it do what I expect it to do is because of the radio signal between me issuing commands, and the drone receiving those commands. It's vital that I remove any interference between the drone and me. Any other radio frequencies, microwaves, or even cell phone communications can disrupt my ability to be in sync with the drone. Communication is vital.

In software engineering, there's the concept of DRY, which is, Don't Repeat Yourself. However, as managers of scattered teams, we have to do the opposite. You have to do a different DRY, and that's Deliriously Repeat Yourself. You can't assume that just because you communicate something once that everyone on your scattered teams will get it. There are so many sources of interference between you and your team. There are just the regular distractions in the places where we're working now. There are things going on in the world that's still dealing with a global pandemic, and all kinds of noise in the environment of your team. It takes repetition to get the signal through. You may announce something on a status meeting over a video call, but you probably want to follow it up with a post in your communication tool, whether that's Slack, or Microsoft Teams or something else. You may even have to follow up doing one-on-one meetings with your team members.

Also, documentation is such a vital part of communication in a co-located team, but it takes on new importance in scattered teams. Your documentation has to be up to date. When people join your team, or something happens about an issue where they're not sure how to proceed, but you're several time zones away and hard to get in contact with, you have to have a great documentation system for helping them understand what to do. You need documentation for engineering standards, dealing with build issues, and all the critical functions of your team. Of course, we don't want to fall into excessive documentation. We need to always keep in mind the second agile value, that working software is more valuable than comprehensive documentation. However, that doesn't excuse us as managers and leaders from right-sizing the amount of documentation our teams need.

You also have to tailor your communication. That means understanding how people process information. Some people prefer to receive information visually, while others prefer to have it written down. Also, when you ask someone for a decision, some people like to get pre-reads to process beforehand, while others like to speak off the cuff. You have to understand how to tailor your communication to each person. Tailoring communication is important even when you're co-located with the team. It takes on really new urgency when you're dealing with scattered teams. A huge part of communication is nonverbal, and presented by body language. Since we're on video calls with our teams where we really only see them from the shoulders up, and sometimes not at all if they prefer to not live under the cyclopic stare of a live webcam all day, so we have to sharpen our communication as much as possible. We're not getting all those nonverbals. We have to tailor what we're saying so that we can clearly get our point across at every point of communication. Clear communication keeps your team moving in the right direction.

Person Management - You Have to Get Personal

Here's the third and final concept to understand when managing scattered teams, person management. That means you have to get personal. With this drone, I have to understand exactly how it works if I'm going to get the most out of it. I need to give it individual attention. This drone records pictures and video on a small storage card that I have to remove from the drone to put in my laptop to download the data on it. However, there are times when I forget to put the card back into my drone before I head out to record new drone footage. The card still is on my laptop. The drone can record pictures and video over the radio connection to my controller, which is usually my phone, but they're in much lower quality than if the card was in the drone and it could record in all the wonderfulness of full, high definition, raw content. When I fail to properly prepare my drone by returning the storage card to it, I get results that are far inferior to what it can do. The same thing applies to your scattered teams. You have to continually prepare them for what's ahead in order for them to be successful.

This preparation has to be done on a person by person basis. You can't just look after the team as a whole. You have to directly invest in each and every individual on your team. That means onboarding is so important. You may be thinking everyone on my team was onboarded a long time ago. However, consider this, have any major changes in how you write, deploy, or maintain code changed in the time that has passed since each member of your team was onboarded? Have your company policies, team compositions, and leadership structure changed? For many of you, all that's true. You may need to consider re-onboarding everyone on your scattered team. The company is probably different enough, that being successful now is radically different than the way it was when they were last onboarded. This is especially true if you're in a remote-forced environment. In fact, for those of you in a remote-forced environment, I highly recommend just re-onboarding everyone because things are so different.

Also, individual attention is so important. Just like my drone needs individual attention to make sure it's ready to go. You have to focus individually on each member of your team. That means robust and rich one-on-one conversations. That's where you talk to each person individually. Really, it's not a status update, because you have so many ways to get status updates. It's having time to meet with each member of your team, and understand who they are. What their hopes are. How they want to create a play-out even after they're done working with you. At Help Scout, we have a company tradition called a fika. It comes from a Swedish practice where you stop working, you get a nice beverage, maybe a pastry, and you talk about anything other than work. I love doing fikas with my teams, because when you can't connect in-person, it's important to find a sweet way to connect remotely.

Finally, there's recognition. You have to find ways to recognize individuals for their contributions. At Help Scout, we have a channel called warm fuzzies in Slack, where we call out exceptional work done by each person on our teams. We also have a spot bonus that managers can use to give just hard cash for those who truly go above and beyond. Giving individual attention to the people you manage mitigates the effects of remote isolation. That's the summary for this third concept.


These are the three categories of ways that you can effectively manage scattered teams. These are the three concepts, first, self-management. Self-care sets you up to be a better manager. Communication. Clear communication keeps your team moving in the right direction. Finally, person management. Giving individual attention to the people you manage mitigates the effects of remote isolation. You may have noticed that these are all good management principles for any team, whether you walk past them every day, or only see them on video calls. However, these principles take on greater importance when teams are scattered. Again, that's especially true for those of you who are operating in a remote-forced environment.

Questions and Answers

Hogbin: What book would you recommend for more information on tailoring communications? I think this came up when you were talking about the Deliriously Repeat Yourself.

Simmons: You really have to tailor your conversations to a variety of conditions, so that's the company you're working in, the company culture, to the individuals that you're working with. Some people like to have things written down. Some people like to receive things through video. I don't know if there's a book that I can recommend. A lot of what I've learned as a manager is just through the manager school of hard knocks, and the written books from that school. Unfortunately, I don't have a specific book. I do think that the idea, which is to know that there's no one-size-fits-all approach to anything in being a manager, especially when you do it remotely. I would say that, just being willing to be curious, and to be curious about the company that you're working in, the people who you're supporting, either your peers and your manager, is really the best way to go about this. By doing that, I think you'll see things that are different. Then you can find ways to flex when you find those differences.

Hogbin: Every manager I know believes that they should model the behavior they want to see, but when it comes to the heavy lifting, we often try and do too much. How would you get people to really understand that it's counterproductive and literally undermines healthy teams to do that, at least all of the time? Any suggestions on how to get people to grok, or understand that they need to take that paid time off or mental health day?

Simmons: When it comes to modeling for your teams, I think that there are a couple different nuances. One is, some engineering managers do write code for at least part of their day, if not part of their week. Some are more pure managers, where you're not writing code, but you manage people who do. I would say that, in the former, if part of your role as a manager is still committing code, then you do want to model all the great things about code hygiene. How you thoughtfully write your PRs, and all that. How you follow the process. I would say that you do want to refrain from being someone who engages in heroics. Don't be that person swinging in from the heavens and fixing all their problems. You have to be comfortable with letting people struggle. That's great modeling, when people come to you, and say, this is taking longer than I thought. Even if you know the answer, just say, take another couple days and see what you find. Giving people time to thrash for a little bit is something we're not comfortable doing. Because we always want to swing in and solve the problem, especially if you're the manager. That's really good modeling. That models that it's ok to not always have the immediate ready answer. That's my first answer to people there. Be comfortable with letting people struggle. Be comfortable even with people failing a little bit, because even that is an opportunity to learn.

Going back to the manager who doesn't write code, you're pure management. It's important to model what the organizational values are. I think one should be that healthy PTO, meaning that you yourself, take PTO. I know, early in my career, I was that manager where I would never take PTO, because I felt that I had to be there for my team. If something happens while I'm on PTO, then if they need me, then I won't be there. Actually, the opposite is true. If you model taking PTO, even taking that week off, maybe once a quarter or at least twice a year, then you're modeling a healthy behavior that your team will hopefully see you doing, and know that is safe to do. By doing that, you're actually going to help them take care of themselves. You're going to make them burnout resistant. You're going to be helping them to actually have a longer career in tech, because so many people, especially after 2020, are just getting to the end of their collective ropes, and either burning out now or about to burn out.

It's very simply the practice of just doing it, just simply taking the time off. Some people even say, during this summer, I'm taking every Friday off. If you have the support from the company, from your manager, then I think that's super healthy. It's actually even a little bit of a revolutionary act, and especially in America, where we're so hyper on, be on all the time, to have that little moment of revolt and say, no, I'm taking time off. Often, to start a revolution, you have to model the revolution. I would say, just model that.

Hogbin: Do you have any tips on how to open a discussion with your leadership or peers if they are modeling unhealthy behavior? One thing if it's yourself, and you are the manager trying to model for others, but what if there's other people in the company who just aren't getting it?

Simmons: The biggest benefit that most frontline managers have, not manager of managers, but managers of ICs, is that we have those detailed touch points with our people, the people who report to us, the people who we support. I'm a big fan of one-on-ones. I think that they should be done everywhere. I know they're not done everywhere, but I think that they should. You should be getting information from the people, the literal humans that you're managing, that you can talk to your management and say, "People are really coming to the end of their rope." Most people aren't going to say, I'm burned out, but you begin to just say, "I've observed this. We used to have very healthy, thoughtful PRs. They're not being done thoughtfully anymore." People are starting to just come to me and say, "I'm sick. I'm not going to come into work today." That's happened three weeks in a row with three different people. Begin to bring your observations and say, I think that the team is running a little bit too hot right now, and here are some of the things that I think we can do to help relieve some of the pressure. Then one is the PTO, and I'm starting first. By coming with your observations, and coming with your expertise, hopefully you'll be able to have that kind of dialogue and get buy-in.

Before you do this, and this is the old saying, dig your well before you're thirsty. Hopefully, you have a track record of the team delivering consistently over a period of time, because that way, it's easy. Then that typically means that leadership says, "Your team has knocked that out of the park. Absolutely. I understand that they're running hot. I'm happy to give you some time to work out this healthy PTO thing." You always want to make sure that you are making the purchase in those accounts before you make a withdrawal, as a friend of mine named Lavie, shared with me. You want to make sure that you are having that track record so that when you need to get some relief to share with your team, you have enough capital to spin on getting that relief.

Hogbin: You mentioned going to the well on this one, and you also said the importance of hydration. What are your personal tips for making sure you stay hydrated during the day?

Simmons: I have water that I keep literally next to me. These are two tumblers of water that I fill in the mornings and I drink. I'm a big fan of make your environment healthy. I have water nearby. I do have my coffee tumbler. The coffee tumbler is smaller than the water, because you should hydrate then caffeinate. Change your environment. Make it easy to get to water, just keep it one reach away, is my pro tip there.

Hogbin: A few questions around fikas, and how to do this when people may be tired at their end of the day. People end their workdays at different times. How, especially on a time distributed team, different time zones, how have you found how to fit it in? How do you get it to work?

Simmons: There are a couple things. At Help Scout I have a team that's stretched out from Vancouver to Spain, so multiple time zones. For fikas in particular, we have a couple things that work. We have an app called Donut in Slack that basically randomly assigns fika partners. That will go through. They don't know, these two people haven't talked in a while, and so it'll set that up. I would say to the degree to which you can automate that stuff, great, use that. My one-on-ones are really sacred. They are regularly scheduled. The vast majority of the people I support, they're done weekly. On fikas, you don't have to do them as often. You should have a fika or a fika-like experience with everyone you support roughly once every six weeks, definitely multiple times per quarter. It's not every week, like a one-on-one. It's not even fortnightly. I do think that having that regular fika where we just stop what we're doing, we just catch up and chat about everything except for work. That is very valuable. Then you should be able to do that on a regular cadence. Hopefully, the time zones aren't so expansive, and people aren't so busy that you can't find 30 minutes in a 6-week period to just connect with your people. If that's not the case, then there's probably deeper problems going on in your organization.

Hogbin: One of the things you mentioned was, even if you've done onboarding before or probably not the way that you're still working now, and this is a super interesting one for me as well, because I think, is it ever too late to redo onboarding? How do you handle onboarding new employees in a digital environment? I think Gabriel may be used to working in-person, and may be new to doing this online. If we're all going to redo our onboarding, what are some of your tips?

Simmons: At Help Scout, we are a remote company. Fully remote. There are people on my team I've never met in person before. I am spoiled in this. I'm spoiled in so many ways at Help Scout that we have a great people team that does this. We have a set of links to information that they can do offline. One of the biggest tools that we use at Help Scout to be a remote company is doing as much asynchronous work as possible. We do a lot of pre-reads, and also prerecorded videos, that the person going through the onboarding can digest according to their schedule. A lot of what we do is that we give immense amounts of trust, and then we give immense amounts of support. We do have a number of just pre-canned, either documents in our document management tool that the person can go through and read at their own pace. That really takes a lot of the weight off onboarding, meaning that we don't have to schedule bodies in space and time. We have a very rich set of documents and prerecorded videos that they can go through. A big part of their onboarding is those kind of, we're going to hop on a Zoom, and then walk you through X, Y, and Z. I think that's the way to do it is to try to be as asynchronous as possible. That does require a lot of preparation. More than likely, the first few people who you re-onboard, you want to create probably some of these artifacts. After that, they'll be ready to go. Then it will be easier to either onboard new or re-onboard current people in your company.

Hogbin: I feel really lucky that I have a fantastic manager who agrees with the importance of a one-on-one. We also do 15, 5s at the end of our week, which are no more than 15 minutes to write, no more than 5 minutes to read. Everyone across the team gets to read them. If your workplace doesn't have that culture yet, I think it's fantastic, but how might someone introduce a one-on-one or a 15, 5, or something that they hear about today and they want to try, but they're not in that manager position? How might they promote the idea? Any suggestions on that?

Simmons: I am super lucky as are you to have an environment where management takes on the task of creating this culture of one-on-ones, culture of those touch points. If you're not that fortunate, then I think you have to pull off what are called the reverse one-on-one. Meaning, you have to say, "Hi, manager. I work for you. I'd like to spend time talking with you. Can we get 15 minutes just to chat? I just want to get to know you." Lara Hogan has a great set of questions, literally called for that first one-on-one, ideally, the manager is asking the person being managed these questions. The reverse one-on-one, you're asking those questions. You're saying, "I obviously work on things with you, we've had a pattern of sharing, but do you prefer me to give you updates in process while I'm working on it." You're like, "Just wait till it's done, and I'll let you right into it." That's talking about communication style.

Then you may ask your manager in this reverse one-on-one, "When it comes to maybe feedback, or sharing, do you like to get feedback? Maybe I can Slack it to you, or do you like to just hop on a Zoom," or whatever you use for video calls and talking. That way you're getting a sense of your manager's style when it comes to receiving feedback. You have to do that. Then, that first meeting may be a little bit rough, but if you're doing it right, and if your manager hopefully is not a monster, then I think they might be like, "This is super cool." You say, "Great. Why don't we do this, if weekly works for you? I can set up a calendar for both of us and just schedule it. If we don't have enough to talk about, then we can make it biweekly. It's important to me that we stay in contact, because obviously, I care about your view of my performance and my work. This just helps me get a sense of that." They'll probably say, assuming your manager is not a monster, "Yes, great. I can give you 15 minutes of my time once a week." If that's not true, there are deeper problems we have to debug in your organization. I think pulling off the reverse one-on-one maneuver is hard, but if you're in this situation, then you can do it.


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Recorded at:

Dec 23, 2021