The one with remote work

Act 1

Paul has been working at WePayments for 5 years as a software engineer, he became a father 1 year ago, which required him to be home more often. Given his wife Paula’s family is in Seattle area and they have a very good weather and school system, the couple decided to move to Seattle from Chicago.

“Good morning.” Paul put down his stuff on his desk as walked into the office. It’s early in the morning and Paul usually arrives around eight o’clock, there aren’t a lot of people in the office yet, except Ryan on his team who also arrives in the office around the same time. Paul likes being early in the office, it’s quiet, and he has time to concentrate and start the day.

“Good morning Paul.” Ryan replied, eating his bowl of cereal while skimming through the news.

Paul is a principal software engineer at WePayments in Chicago, he has been at the company for 5 years, which is a long time for being at a software company. Paul started at WePayments when it was only a 50 people company, and today WePayments has grown to a 500 people company with lots of clients processing payments using their software. It was a wide ride, and Paul has been on plenty of projects throughout his time, and overtime grew into a principal software engineer role. It’s an influential and flexible role, Paul isn’t tied to any specific team, but rather, the company has certain initiatives that requires deep technical expertise, and Paul will be assigned to those initiatives for a period of time. When the initiative stabilizes, then Paul can move on to a different initiative. What Paul likes about the role is that he can utilize his knowledge on a variety of projects. What is challenging for Paul is that he has multiple projects at the same time, which requires a lot of communication.

Paul opened up his email, there are already at least a dozen of new emails waiting for his response, meanwhile, on Slack (chatting app), there are another dozen of direct messages or group chats waiting for his response as well. Most of these pending messages are about the recent project of data pipeline - as the principle engineer, Paul is architecting the overall design of the system. The data pipeline project is a strategic project for WePayments - as the company grows, there is a growing need to generate reports and perform data analytics effectively. Paul is used to the pressure, and he separate out pending communications in separate buckets - one bucket is “answering questions”, the other is “needs action”. He redirects most of “answering question” ones to the wiki page he created about the project, spend most of his time on items that “need action”.

Outside of work, Paul has another big thing is mind: his family. A year ago, Paul and his wife Laura welcomed their first child Sophie, and it has brought joy and exhaustion beyond Paul’s expectation. Nevertheless, Paul has been more at home spending time with his wife and daughter. Paul used to get drinks with WePayments co-workers after work but since his daughter is born, he has been skipping most of the after work socials. It was bad for Paul, in fact, every day after work, he can’t wait to be with Sophie and Laura - seeing the smiling face of Sophie makes his heart skip a beat, and he won’t trade anything for it.

Paul and Laura has their home in Oak Park, a Chicago suburbs, and Paul has been taking the train to work every day. Laura has been a staying home mom ever since Sophie was born. Taking care of a newborn is a full-time job, and it has been challenging for them lately - the winter in Chicago is windy and cold, and Sophie has already been sick once due to the cold weather. Laura’s parents are in Seattle, who can help out raise Sophie, and they have expressed interest in being more involved. In addition, the weather in Seattle is a lot better than Chicago, the two have been talking about moving to Seattle.

Paul thought about his discussion with Laura, and figured that a good first step is to talk to his manager Diana. He has a good relationship with Diana, still he’s not sure how she will feel about her working remotely, honestly, he’s not sure how he feel about working remotely himself.

“How’s your day going?” Diana asked Paul during their 1-on-1s.

“Doing well! We went to the zoo this weekend. Laura and Sophie are doing great. Sophie is growing really fast.”

“I know! Time flies fast! Did you have a good time at the zoo?”

“Yes, we did! Sophie was fascinated about the dolphins and we also watched a dolphin show together. It was fun.”

“Great! Glad you had fun!” Diana smiled, and the two had a pause, which usually means that it’s time to talk shop in 1 on 1s. Paul thought for a moment.

“So there’s one thing I like to discuss, that is the possibilities of working remotely for the company.” Paul finished the the sentence and saw Diana’s eyes light up a bit, he nodded and continued, “Laura and I have been talking about moving to Seattle, because we have family there, and also the weather is nicer for Sophie to grow up.”

“Yeah, family is important, and the weather is nicer there.” Diana added and agreed, in a way trying to encourage Paul to speak more.

Paul nodded to echo back Diana’s statement, feeling that it’s going well overall. The two again fell into a short pause, both seem to be deep in thought this time. After a while, Diana broke the pause.

“You are a great engineer Paul, and I think you will be as effective working remotely as if you are working in office. However, I’m a bit concerned about two things: how you will like working remotely full time, and how the team will adjust to having you remote but not in the office..” Diana paused there and looked at Paul, waiting for Paul to say something.

Paul agreed with Diana’s concerns, and honestly he doesn’t know how he will feel about working remotely fully for himself. He has worked from home here and there to take care of stuff (Laura is staying home full time so it has been a huge help), but he know that working from home completely is a different ball game. However, he has talked about this with Laura at home, and he has planned out a gradual transition.

“Those are valid concerns.” Paul replied, “and I have thought about how to transition to work remotely. How about I start working from home more often, like 2 or 3 days a week, to see if it works out for myself and the team?”

“That’s a great idea.” Diana nodded, feeling like they have reached an agreement.

Act 2

Paul continued to work at WePayment remotely (first a few days then full time), he has to adapt a different routine in order to work effectively, however, because his knowledge of WePayment’s eco-system and his position as a principal engineer at WePayment, the transition was relatively smooth.

After he talked to Diana, Paul also informed the team about his plan of gradually transitioning to work from home full-time. The team members are very supportive of Paul’s choice, and they seemed unconcerned if it will impact the team. For the first few weeks, Paul intentionally increased the days he works from home - first two weeks two days a week, then to three days a week.

At first, spending a major of time working from home was uncomfortable to Paul. He is used to see people face to face and interact with them in real life. Online meetings and chats have solved part of that problem - Paul still sees his team members daily, and was able to work get enough context on business and tech.

Another challenge Paul identified is that it’s easy to lose a “routine”. When people come to work in office regularly, people follow a routine - wash, get dressed, pack the bag, then go to work. However, working from home makes it easy to skip ‘routine’, and because of that, Paul felt that he was not completely in the ‘zone’ when working - part of his brain still feels relaxed and distracted. He noticed this problem and on the third week of working from home, he started to form a routine for working from home - he gets dressed, get coffee, and get into a work mode before actually start working. Having a routine ‘tricked’ his mind and body to get ready, and he felt getting more productive over time.

After four weeks of working from home most of the week, Paul finally made the decision to work from home full time. His work productivity, at least in his point of view, hasn’t been impacted by his change of style. Because Paul has been at the company for a while, he has technical domain knowledge for most of the systems at WePayments. Through chats and emails, Paul was still able to understand all the business context and engage in productive conversations online. One day, Ryan even messaged Paul saying that he appreciated that Paul has made the team feel at ease by being remote and proactive. “It’s like you are still working from the office!” Ryan joked.

Paul also started to like working from home more. Because he’s the only person around, he was able to focus more on the task at hand, without participating much of other chatters. Besides regular meetings such as daily standup, a short meeting where team members go around and report what they did yesterday and what they plan to do today, Paul is free to arrange his time independently. He appreciates that because it gives him more flexibility to prioritize his time on Laura and Sophie - as a father of a one-year old, he needs to take on a lot to help out raising the child. For Laura, she is happy to have Paul contribute more in parenting, even for a stay-home mom, raising a kid is a lot and as a couple working together, she is freed up to do more self-care, like sleep and exercise.

As Paul continues to work from home, and get a grasp of his own routine. The couple starts to talk about their plan of moving to Seattle. There are a lot to think about and plan, but the two feel like right about now is the best time to do it - Sophie is entering kindergarten at three, if they move now then they will have some time to get accommodated to Seattle. In addition, Paul is also contemplating about switching to a new company - he has been at WePayments for about six years, and given Seattle is a technology hub, he wants to see what else is out there. Also acquiring the ability to work from home gave Paul the advantage of applying to other remote friendly companies too. He told Laura that he will find a new job that enables them to move to Seattle before the actual move, and Laura agreed.

Act 3

Paul moved to a new company LemonBank based off San Francisco and started working remotely for them. He soon discovered the gap of remote work for LemonBank, and thought about ways to bridge that gap.

It’s been a while since Paul interviewed for a position, and he decided to be diligent about it. As a senior member of WePayments, he has done tons of interviews and knows the general flow of a technical interview. He drafted out a plan of “practice routine” that consists of coding practice and software design. In addition, he thought about what companies he would like to interview, he likes being in financial tech industry and wants to be a part of a financial tech company that has high growth as well as interesting problem to solve. And of course, the company must be remote friendly.

After a week or so searching, Paul compiled a list of tech companies in the Seattle and San Francisco area. On the top of that list is LemonBank, who provides a better and faster user experience for banking by shifting traditional banking to online banking. Paul applied for the technical lead engineer position on their website, and within a day, the recruiter got back to him showing the interesting. This is one thing about tech - skilled individuals are always in high demand. After the recruiter’s call, Paul had a technical phone screen with an engineer, he solved a small problem which took him about 5 minutes, after that, LemonBank flew Paul to a full-day onsite interview. The process was very similar to the one at WePayments, Paul finished the interview with ease, and got an offer next day. After a two rounds of negotiations, they locked on a compensation package, and given Paul is moving from Chicago to Seattle, they set his starting date to be in a month.

The whole job searching process only took Paul about a month. Laura was super happy to see Paul land a job so quickly (“Tech industry is really great!” She said, with a slight jealousy), and the two immediately started the plan of moving after Paul finalized his job offer. They found a 2-bedroom rental condo 2 miles north of Seattle, it has a reasonable price and closer to Laura’s family. In 2 weeks, the two packed up their stuff in a U-Haul, and drove cross-country from Chicago to Seattle.

The new home looks smaller comparing to Paul’s house in Chicago - they had a single family home in Oak Park, IL where they have two stories and a basement. This new home only has two bedrooms and two bathrooms, it reminded Paul of his first apartment with a roommate, when he just graduated from college. Nevertheless, they are happy and excited to start their new life together in a new environment.

Laura’s family are pretty happy to see them move, too. Laura’s parents couldn’t get enough of Sophie, and they invited Paul and Laura over during the first week they moved. Paul felt grateful that they have families around Seattle, and besides, the weather seemed nicer than Chicago.

A week after they moved into the new home, Paul flew to San Francisco to start officially work at LemonBank, he got onboarded to the engineering team who’s in charge of the saving account product - if a client puts money in a LemonBank and opens a saving account, it should yield a guaranteed interest to the client. To client it seems like an easy feature, but many things are happening in the background: as a start, LemonBank needs to wire the funds to a partnered bank and accrue interest in a different account for bookkeeping. Having worked at WePayments for a long time, Paul understands that payments technology requires many complicated workflow in the back office, and he has a feeling that LemonBank is challenged with different workflows, yet of the similar nature.

What’s more, Paul noticed the culture difference between WePayments and LemonBank - at LemonBank people seemed to be more intense and loaded with work. He introduced himself to the team, got settled with his equipment, but immediately got added to the technical design meeting next day. During that meeting, Paul heard a lot of timeline terms throwing around. “We need to finish tier-1 product features by mid March, which is in six sprints, and two sprints before March, we should start planning for tier 3 and 4 product features.” Given Paul is a tech lead on his new team, he knew that the expectation for him is quite high - not only he’s expected to ramp up quickly, and the team is expecting him to lead and guide the direction of the project.

Paul went on his flight back to Seattle feeling excited and concerned. He’s excited because he sees great opportunities in building cool, new products, he’s concerned because he has a feeling that the culture here is quite different. On top of that, he’s not sure how “Working from Home” will impact his productivity.

The first few days was a lot of learning and catching up, Paul spent a lot of time reading documents and installing the projects, he was able to get different apps up on running and had a solid sense of architecture. Just like many other tech companies, LemonBank has gone through fast growth and has accumulated a good amount of bad code, also known as technical debt.

As Paul started to work on features and take on more responsibilities, he noticed a few jarring things about being working from home. Although both WePayments and LemonBank use the messaging app Slack, the two companies use them very differently. At LemonBank, there seems to be more chatter about things other than work - family photos, where to eat in San Francisco, etc. However the conversations about work and business context is very limited. Most of the technical discussions and decisions happen in real life (IRL), rather than online.

Two weeks after Paul joined the saving accounts team, the team is trying to implement a new workflow to adopt Canadian dollars as another option of currency, in order to support LemonBank’s effort to go international. Paul knew that to enter international market requires a lot of financial regulations, but he was having trouble finding the product requirements around building to compile with those financial regulations. It’s not until he asked the product manager Marc on his team that he realized that the product manager had an organic conversation with one engineer on his team, and send the document to him without involving the whole engineering team. So the knowledge sharing is very fragmented.

As the only work from home “WFH” engineer, Paul felt this growing connection between him and his team, and he feels that the problem is not just within his team, but the whole culture at LemonBank: because the whole company is still 99% working from office, it has a bias towards real life communication than ensuring knowledge is shared to as many people as possible. Paul know that if he wants to be successful at LemonBank, he has to help shift company’s culture to be more “work-from-home” friendly.