Managing Remote Teams: How to achieve together, when everyone is working from home

Managing Remote Teams

How to Achieve Together, When Everyone Is Working From Home

Lukasz Szyrmer

Managing Remote Teams: How to Achieve Together, When Everyone is Working from Home, 6th edition

Published by LAUNCH TOMORROW

Warsaw, Poland

Copyright 2020-2022 by LUKASZ SZYRMER. All rights reserved by LUKASZ SZYRMER and LAUNCH TOMORROW.

No part of this book may be reproduced in any form or by any mechanical means, including information storage and retrieval systems, without permission in writing from the publisher/author, except by a reviewer who may quote passages in a review. All images, logos, quotes, and trademarks included in this book are subject to use according to trademark and copyright laws of the Poland.

SZYRMER, LUKASZ, Author

MANAGING REMOTE TEAMS

LUKASZ SZYRMER

ISBN: 978-1-7817977-0-6

BUSINESS & ECONOMICS / Business Communication / Meeting & Presentations

BUSINESS & ECONOMICS / Organizational Behavior

SELF-HELP / Communication & Social Skills

QUANTITY PURCHASES: Schools, companies, and groups may qualify for special terms in bulk. For information, email [email protected].

Table of Contents

Introduction

Rethinking meetings

Quick challenge ideas

Why rethink meetings when going online

The impact of Where we meet online

Who needs to be involved

How to contextualize when remote

How to run successful meetings

How to move meetings online successfully

Top 15 tips when running your meetings online

What you can do now

Section takeaways

Rethinking motivation

Quick challenge ideas

Why alignment is linked with motivation

How to reduce ambiguity and why it matters

Forests, trees, and motivation

Why context drives people

Why department boundaries matter most

How to align or realign within a company

If the direct approach fails

How to break down silos in your company

What you can do now

Section takeaways

Rethinking productivity

Quick challenge ideas

So how do we know our people are working?

Why traditional productivity measures don’t add up

What we’ve got here is a failure to delegate

The wolf you feed

Given outcomes, teams can manage their own work

How to apply a team lens to output

Revisiting individual productivity

How to track productivity in real-time

When will the team be done?

What you can do now

Section takeaways

Epilogue

Appendices

Principles, quotes, and rules of thumb

Glossary

Bibliography

Resources

Notes

Introduction

Exploring an alternative way to achieve together–through others, who are all remote.

So glad to see everyone on the call

Work is fundamentally a social experience. As adults, we need each other to decide what is important, what finishing work ultimately means, and finally…to actually do the work. This ability to coordinate efforts socially was unique among primates; our ability to read cues enabled homo sapiens to build pyramids. The same biological and psychological messaging powered in-person collaboration in an office. While we lose much of this ability when working remotely, there are newer ways to collaborate as groups of humans over the internet. Highly effective and inclusive, these approaches also build upon how the human brain works, focussing more on cognitive ways to collaborate. Instead of taking a look at what makes remote work unique, this book examines what has stayed the same: how our relationships at work and the wiring of our brains help us define and achieve what’s meaningful–together.

As a tech leader, you’re no stranger to navigating uncharted territory and adapting to new realities. But leading remote teams presents a unique set of challenges that only the most cutting-edge technologies can’t solve on their own. These days, developers can get another job offer almost as fast as it takes them to commute into the office.

Gone are the days of impromptu whiteboarding sessions and lively discussions around the ping pong table. No longer can you rely on the serendipity of hallway conversations to gather insights, the energy of in-person workshops to generate ideas, or the visibility of being in the same room to keep your team on track.

Now, you’re tasked with keeping your team aligned, motivated, and productive across a matrix of Jira tickets, GitHub commits, and endless Zoom calls. It’s daunting.

Yet it also presents an incredible opportunity to redefine what leadership looks like in the digital age. To leverage the best of what technology allows with follow the sun progress across time zones. To connect and achieve, despite spending most of your time alone in your home office. To find new ways to listen to your customers, collaborate with your team, and drive your product forward – easily taking into account the complexities of a distributed workforce.

Who am I to be talking about this?

My name is Luke Szyrmer. I’ve worked and managed remotely over a decade to date. I’ve successfully led teams spanning multiple continents, time zones, and industries. I’ve seen what works and what doesn’t, in large companies and in fast growing startups. When building and when selling.

While I respect the value of rigorous testing in academic research, I’m a classic practitioner. I only care about theories that explain what’s going on, and that produce results in practice. This book started as an experiment, to solve specific problems I faced with slow progress on a distributed software team, trying ideas sourced from research to address my teams’ challenges. A lot of them weren’t useful or relevant, but this book contains the ones that are.

In practice, my secret sauce was leading teams by enabling them to thrive and collaborate, rather than extracting as much ‘value’ from each ‘human resource’ as possible. As a result, few of my team members wanted or needed to leave. In fact, I’ve had many employees return to my team after leaving for a competitor, rather than just leave. This mindset has remained effective as I’ve worked across a few different industries, as well as supporting startup executives across even more with similar challenges.

Instead of only looking at what makes remote work unique, this book examines what has stayed the same: how our relationships at work and the wiring of our brains help us define and achieve what’s meaningful–together. While it’s true we lose many of the cues we’re used to as human beings working in person, we can coordinate the efforts of tens or hundreds of people using techniques like collaborative editing in ways that were impossible offline.

This book is your guide to unlocking the full potential of your remote tech team, especially if you are involved in creative or innovation work requiring learning and experimentation to speed up delivery. Drawing on practitioner insights from agile methodologies, lean principles, and the latest remote leadership research, it offers a framework for building high-performing teams that can innovate, iterate, and deliver value faster than ever before.

In the chapters ahead, we’ll dive deep into three key areas of remote leadership through a tech lens, covered in 3 separate sections:

rethinking meetings

rethinking motivation

rethinking productivity

Whether you’re a seasoned CTO adapting to a fully remote model or a newly-minted tech lead looking to build your remote leadership toolkit, this book will equip you with the tools and frameworks you need to lead your team to success in the new world of work.

The journey ahead may be uncharted, but with the right mindset and approach, the destination is within reach: a thriving, high-impact remote team that achieves extraordinary results together, no matter where they happen to be located. By embracing the principles and practices outlined in this book, you’ll be on your way to building a remote tech team that is resilient, innovative, and ready to tackle any challenges the future may bring.

Let’s get started.

Rethinking meetings

In which we focus on where the action is and ensure that everyone can execute effectively

Now that we all agree, let’s get on slack to discuss why it will never work at our company.

Quick challenge ideas

The fastest way to learn something new is learning by doing. To introduce change to your teams, you need to start by trying something new yourself to figure out what might work.

The following are specific things you can try, to figure out if there might be a better way for you and your team to work. Put the book aside, and try doing one of these before you continue reading:

If scheduling a meeting, schedule it for twice as much time as needed. At the beginning of the meeting, suggest that you might not need all of the scheduled time. If you finish early, you’ll have that time to catch up on non-meeting work or just recharge.

Send an email suggesting a no meetings day policy for one day per week for your team. Trial it for a month. I like Wednesday, personally.

If you already use an online whiteboard, try running the whole meeting using the pen/pencil tool. Minimize the use of text. Draw your agenda as a pie chart. Draw options other people propose as you listen. And so on.

If someone says they haven’t had the time to prepare for a meeting, give everyone 10 minutes to prep during the meeting. For example, if you’ve prepared a report, give everyone time to read it before you discuss it.

If you have a data connection and the weather is nice, grab your phone, make sure you have your company’s meeting app installed, and take a walking meeting. Or work on your chat app as you walk.

If you have your company’s meeting app installed on your phone, work for an hour or an entire day from your phone only. Feel free to walk around the house, lay down, etc.

The aim here is to step slightly outside of your current routine(s). It might feel somewhat uncomfortable, but you’ll realize you have more autonomy than you assume.

Feel free to email me with any observations at [email protected].

Why rethink meetings when going online

To say the least, I was taken aback. I was noticing a pattern of silence in calls, even though we’d just returned from a productive in-person workshop with the whole team.

an old meme

One day, an operational standup call had over-run to about twice the scheduled length. During the call, my boss, an architect, and I were metaphorically pulling teeth. No one wanted to say anything. The architect even explicitly referenced the teacher played by Ben Stein in the 80s movie Ferris Bueller’s Day Off saying, Anyone? Anyone?

Immediately after we hung up with the team, I called my boss to do a quick post-game analysis.

You see what I mean, here, when I said they don’t seem involved, I started.

I don’t get it, he said. They aren’t saying anything unless we ask them directly. We pay them, and it’s part of their job to participate in meetings.

My stomach tightened.

I think we’re missing something here, but I don’t know what it is.

It wasn’t a team quality issue. The team was composed of people who were probably the best in the company. I had a lot of respect for each individual’s expertise from when I worked alongside them in the trenches. They were locking up exactly when they could contribute the most to the conversation and decisions. And I was pretty sure they were keen to be part of it. The new product initiative was started with a lot of fanfare. And to be honest, it was already almost an honor to be part of the team.

But I don’t think it’s a question of pay or anything formal, I continued. I had a team of 14 allocated full-time to this initiative. It’s not like anyone was pulling them off to different priorities. It’s almost like they are just really distracted, and this distraction even shows up during meetings. And presumably, it’s the same thing throughout the day. Or maybe they were afraid to speak up.

I couldn’t fall back on peeping to see what people had on their monitors, which worked for in-person workspaces. All I had to go on was what I saw happening. And what I heard during meetings. The intuitive mirroring of others’ emotional states didn’t work online. Feeling connection through physical touch, like a handshake bolstered with oxytocin, wasn’t there anymore. Granted, I was only meeting with the team as a whole for a small part of the week due to time zone constraints.

This was primarily about going remote. The human dynamic fell flat. It caught me off guard, and I didn’t realize how big of a task I had ahead of me. Instead of lacking empathy, I was overwhelmed. In the words of Erica Dhawan, author of Digital Body Language, I didn’t know what empathy meant anymore in a world where digital communication had made once-clear signals, cues, and norms almost unintelligible. If non-verbal communication in person makes up 90% of what we communicate, and only 10% is about the content of the message, then we are missing the building blocks of connection: posture, proximity, smiles, pauses, yawns, tone, facial expressions, and volume or losing it depending on the speed of our internet connection. For example, one research study found that with intermittent delays of 1.2 seconds, people were more likely to be rated as less attentive, friendly, and self-disciplined than if there was no delay.

Skip rethinking meeting dynamics at your own risk. Offices become less important, even if they are distributed. And meetings and company culture are woven into people’s personal lives and vice versa. All participants’ experience of meetings changes significantly in that case. This is true regardless of the symptoms you are seeing:

A lack of engagement

A company culture that doesn’t support change

An inability to finish things

Meetings are the first and easiest place to start diagnosis. They are practical and specific. Everyone is there anyway and sees what happens. This is particularly true for recurring meetings.

If you can fix one meeting, the positive impact accrues over many future months of work. For this reason, recurring meetings have a highly leveraged impact on productivity: a good one pulls it up a lot, and a bad one can drag it down. While they are not a silver bullet that magically makes all of your problems disappear, getting your meetings right means it’s easier to make decisions together and hold everyone accountable for them. With solid meetings, it’s a lot easier to dive deeper into motivation, productivity, and several other factors.

And once I improved online meetings after a lot of experimentation, the team came together. I didn’t need to organize meetings myself anymore; they were happy to convene without me if needed, but included me when they wanted my input. Team members supported one another. They owned the work they picked up. And with all of that working correctly, it made it possible to go after more ambitious goals.

Before moving on to the how-to details, let’s dig into why this worked for me in the following chapters.

Key takeaways

When moving online, meetings change significantly because of how we read body language and tone of voice.

Be prepared to rethink meetings from the ground up, to get them to work for you, your teams, and your company.

The impact of Where we meet online

When I was organizing an offsite for a team that seemed to be coming together after some struggle, I needed to get the flight details from everyone. Eighteen different people were flying into the target location from multiple airports and time zones. My boss asked that I put together a spreadsheet with all of these details so that we don’t lose anyone upon landing. It was totally understandable, but it felt like I needed to embark on an initial request, followed by a few days of chasing emails, until the last straggler would finally send me their flight times so that I could organize it in a spreadsheet. Just thinking about it made me tired. Instead, I had an idea. Even though Microsoft was the company-preferred supplier of internal tools, I created a Google Sheets workbook in my personal account and dropped the share link in an email to all the workshop participants. Within two hours, I had 18 individuals’ accurate flight details for both the flight in and out, along with several additional comments. Each person was the expert on their own flight. I just created a structure in which we could interact productively. I made it possible for them to contribute in parallel, and as a result, there was much less work overall.

I felt surprised, even energized, by this experience. At the time, it was the first visible step toward the team taking ownership of their work and output. It felt like a symbolic beginning of a larger shift.

The team members were stepping out of a company leadership style that was highly centralized. They were accustomed to having someone think for them, tell them what to do, and then nag them until they did it. Instead of directing them, I ensured they had the right environment and trusted they did the right thing (because it aligned their goals with the company’s). A supportive environment instills good habits that are repeated many times over and gets rid of destructive habits that undermine positive interactions.

My role was to optimize this environment to help the team achieve high productivity. In this case, my deliberate choice of a tool that allowed everyone to edit at the same time created exactly the right environment for collaboration. We could quickly get through minutae, and have more time for deep thought and discussion.

Structuring team interactions

Structure affects behavior and, ultimately, productivity. Ask any architect who’s