A Leader’s transition guide to Working from Home

My husband kisses me goodbye, starts his car, and drives into morning traffic. I wave, hug my warm mug and walk the 5 steps to my home office. I never thought I would be able to do it while in a leadership role.

I’ve been leading teams for years. And for years I’ve heard, and believed, that leadership cannot be done from home. How would I “walk the halls?” But in the last 6 months I’ve transitioned to leading a team that works from home, while I work from home myself. I now have colleagues and clients in Europe, Asia, and across North America. This was a deliberate move because I believe work-from-home will be the future of knowledge workers and I wanted a front row seat to how it’s done. For a long time, the lonely engineer who has one meeting a week was allowed to work from home. But with the advance of technology and culture, it is possible, nay, more effective, to not just work from home but also lead from home. Leading from home is different than leading by walking through the halls. And there is a way to set up a team for success when they work from home. So allow me to share with my observations and lessons learned while the transition is still fresh on my mind.

Photo by Mimi Thian on Unsplash

First, some context on my journey. For years I’ve been leading teams of Product Managers, with a sprinkle of members from design and marketing. I’ve led teams who are:

(1) Co-located, completely from top to bottom, so I can walk the halls.

(2) Hybrid, with co-location between PM, Design and Engineering, and remote reporting lines to leadership. I had to lead part of my team from afar, but each of my teams could have hallway conversations.

(3) Work from home, completely fromtop to bottom. Everyone is set up to work from home. There is a physical office in a HQ city and some people drop in a few days a week. But many prefer to work from home or co-working spaces. Half the company does not live in the HQ city, so they always dial in. Each year we all fly to one location for a one-week workshop.

Transitioning to work from home as a leader was not easy. But technology has finally caught up to support a work from home arrangement for knowledge workers. And working in the Hybrid environment has given me the foresight to screen for a team that would succeed in a work from home arrangement.

There are three aspects to enabling success when working or leading from home: 1) Home set-up, 2) Company Culture, and 3) Tooling.

Setting up your Home for Work from Home success

Photo by Jonathan Francisca on Unsplash

My first three weeks were rough. Working from home can be isolating and distracting at the same time. While it may seem easier to focus without interruption from co-workers, my mind wanders to the pantry whenever the work becomes challenging. My body was less happy too because I had less built-in walking in my routine as I often stay in the house all day. On top of that I had a time zone difference with my team, so my workday started at 5pm. After testing out a number of set-ups, I have found the following to be the most helpful:

• Set up a separate space as the office, away from the main area of the home. The space needs to have a door. Ideally it’s up a flight of stairs so there is a commute, even a short one. Working from the family couch may work for a meeting or two, but did not work very well on a sustained basis. It’s also more respectful to everyone else on the calls if you have good audio quality. There’s nothing worse than someone calling in from a cafe with a noisy background, especially if that person is leading the meeting.
• Set up the workstation with a treadmill, or exercise bike. Some people are disciplined about going for a morning run. I shy away from the cold air when it’s cloudy outside. But if I’m literally sitting on an exercise bike while I dial into every meeting, it’s easy enough to move my legs and get some bonus exercise.
• Set up social phone calls. Going to an office often means heading into town or a busier area where it’s easier to meet up for lunch with friends. Working from home means I’m in a more residential area. I would have to ‘commute’ to attend a social lunch, which is just enough of a barrier to keep it from happening too often. Since there are no water cooler conversations either, I’m no longer hitting my human-interaction quota each day to stay healthy. Scheduling social phone calls with friends really helped keep me sane.
• Pro-tip: Use two devices. You might dial in from the mobile phone on occasion while screen sharing from the desktop. This can greatly improve the audio quality. It seems mobile phones have better audio compression than laptops.

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Setting up your Culture for Work from Home success

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The culture of the company is paramount when it comes to work from home. With less face-time, norms and work styles have to change. With no serendipitous hallway brainstorms, deliberate effort has to be made to move random thoughts forward into an action plan. Here’s what I learned about setting up a company’s culture for work-from-home success:

• Autonomy, Purpose, & Mastery has to be the motivator for every employee. And leadership is responsible for ensuring this. This was explained in Dan Pink’s book Drive. While this ought to be true in every company, the truth is that at co-located companies it’s possible to get away without it for some time. Employees show up for work, they sit next to their peers, they do the work through social motivation. But in a work-from-home company it’s not possible to get away without it. As a leader, here’s how I think about the three.
• Autonomy refers to a clear delegation of authority. What decisions can the employee make on their own vs escalate to leadership? Being clear about this autonomy allows people to execute in their own time zone and unblock their own work. In a work from home culture that incorporates multiple time zones, this clear delegation of authority is particularly important. Otherwise employees can be blocked in their work for hours before a decision can be taken to unblock it.
• Purpose is the reason they show up. This may be different from the company purpose though. As a product leader, I work on creating a compelling company vision. As a people leader, I also tap into each person’s personal purpose, which may be different. Some join the company to help people. Some join the company to be a part of something bigger. Some join to have steady, flexible work that gives them a chance at mastering a skill. Making sure each person is compelled by the company vision is step one. But the second, more relevant step is understanding each person’s individual purpose so that I can align their deliverables with that purpose. When their purpose and deliverables align, I don’t have to look over anyone’s shoulder, ever.
• Mastery is their source of pride. Every person is an expert at something or interested in becoming an expert at something. In co-located companies it’s easier to spot each other’s strengths, but in work-from-home companies I need to deliberately call out these attributes in my team. When new hires join I ask them to write a “How to work with me” blog post that highlights their own strengths, so that others can come to them for those strengths. For those working on becoming an expert at something, I pull in people and resources who can help them build up that expertise. When work becomes a source of pride, I have a very happy, productive team.

• Get religious about Writing things down. With limited face to face interaction, different time zones and different cultures, it’s impossible to move the ball forward without writing things down, religiously. There are many tools that enable communication, and I’ll get to those in the next section, but more importantly, the culture needs to support the use of these tools. People’s habits would have to change. Every meeting, every decision, every idea thread, every discussion and more needs to be deliberately written down then kept in a place where others can see and add comments. Sometimes it’s written casually in Slack, sometimes the topic elevates to a Confluence page. Then someone needs to own that page, and actively integrate new comments into the body of the page and evolve the idea, decision, or plan. This means you need the next item, which is:
• At least one Strong Communicator on every team. Communicators are people who understand the channels of communication, and which to use for which type of communication. They’re the ones who know when it’s appropriate to send messages back and forth on Slack, and when that conversation should elevate to a meeting. They know when decisions can be closed by sending around a written DACI, or when a face to face discussion is necessary. Having a sprinkle of very strong communicators across different teams will help broker communication efficiency, and ultimately teach everyone else to make good judgments regarding communication mediums.
• Low egos. Giving people the benefit of the doubt. There is a greater chance of miscommunication in a work-from-home setting. Written messages sometimes come across differently than spoken ones. In addition to having strong communicators set at standard for communication, make sure you hire for low ego. These are people who seek to understand rather than jump to conclusions. These are people who engage in a time of tension rather than disengage.
• A Transparent, high-trust ethos. When communication is a bottleneck, the last thing you want is to create more ‘grapevines.’ Silos naturally form in any organization. In work-from-home settings, it’s even more important to shatter those silos. Take appropriate Slack DM (direct messages) and move them to the group chat. Shine light on decisions in progress that may affect certain employees. There is a tremendous amount of trust in operating this way. You’ll have to trust that sensitive information will not be leaked by your employees. You’ll have to trust that people will show up with low egos and keep the broader objective in mind when they read about decisions that may affect them. You’ll have to trust that people will stay constructive when they contribute to the conversation. You’ll have to trust that people are paying attention to the conversation in the first place.

Trust is an incredibly important aspect of leading a work-from-home team, and establishing that trust with and among the team is the most important job for any leader of a work-from-home team.

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Setting up your Tooling for Work from home success

When transitioning from a co-located team to a work-from-home team, there are only two main toolset areas to pay attention to. These are collaboration tools, and timezone management tools. You may be using many of these collaboration tools already. By transitioning to work-from-home, you will lean on these tools more and discover ways to use it that may even surprise you. Here are the most important tools in your work-from-home toolset.

Collaboration tools for the whole company:

• General Collaboration and social interaction (Confluence, Slack, Notion etc)
• Brainstorm tools for short 1–2h brainstorms (Jamboard, Miro, Trello, etc)
• Cultivating Culture (Google Meet, Zoom, Slack, Microsoft Teams)

Collaboration tools specific to Product and Engineering:

• Leading and Communicating Vision and WorkPlans (Dragonboat, Loom, Confluence, etc)
• Product demo and gathering feedback (Loom, Invision, etc)
• Tracking execution (JIRA, Dragonboat)

Timezone management tools:

These are mostly settings within your current calendar system rather than a new toolset. It also involves a coordinated use of the calendar so each employee’s availability and work hours are clear. I use Google Calendar but I imagine Outlook would have similar features as well.

• Multiple Timezone setting, so you can view 2 time zones at once next to the calendar
• Setting up a separate calendar to track vacations / out of office
• Setting up “work hours” so a moon symbol shows up next to your name when a meeting is outside your office hours.
• Grant permission for everyone in your organization to see the contents of your calendar. This speaks to the Transparent, high-trust ethos mentioned earlier. When my colleagues can see what my meeting is, it’s easier for them to schedule a group meeting over my 1:1 time, assuming that I can move that 1:1 easily. This requires a high-trust environment, and not everyone is ready to do this. But it saves me and my colleagues an incredible amount of time in scheduling. There is also an added benefit of understanding what others are working on. For example, during a meeting with my CEO, she observed on my calendar that I have a meeting with another executive later the same day. So she asked me to relay a concept she just shared with me to that executive, and to evolve that concept. This saves her the 30 min or more necessary to separately schedule time with that executive. It’s extremely efficient.

Lastly, since I work with multiple time zones, I have a separate app to show multiple time zones at once called Worldtimebuddy. I use it to find a time for those crazy meetings involving three extreme timezones.

As you can see, working and leading from home can take some transition work. But as I watch my husband pull into traffic again today, I have to say that it’s all worth it.

Connie Kwan offers VP Product as a Service for B2B technology companies. She coaches CEOs on product and brand story, roadmap strategy and work-from-home culture. Find our more at www.productmaestro.com