Working Remotely: The Pros, the Cons, and How to Succeed

In this interview with Aleyda Solis, Hamlet goes into the ins and outs of working remotely, why he chose this for RankSense, and why it works so well. Watch the full interview on Remoters. 

RankSense is a fully remote business consisting of employees from all across the globe, including India, Europe, and the United States to name a few.

Note: This interview is from January 2020, prior to the COVID-19 pandemic.

Aleyda: When did you begin working remotely? Was there ever a time where you and your team were working together in a physical location?

Hamlet: RankSense is my fourth business. With my first two businesses, we had a physical location in the Dominican Republic, where I’m originally from. During this time we had a local staff of about 40 people in an office where we would meet in person. 

In my last business, I started playing around with the idea of a remote team. I had a challenge finding talent in the D.R., which was my primary driver for going remote. I would interview over a hundred people to fill a developer role just to come up short each time due to the scarcity of local talent. In the Dominican Republic, this strength was lacking. 

I ended up finding great developers in Europe. It was great, I could hire people through a freelance website called, Upwork. Although you may end up with a mixed bag of people, over time I developed skills on how to interview and qualify good people for a remote team. 

Aleyda: When you started RankSense, did you already know you wanted to pursue a remote business?

Hamlet: Yes. I knew what it was like to have people in an office and the implications of my time in the Dominican Republic. There are pros and cons, but I saw more pros from my constraint, the talent pool. That was my main challenge, but other factors like the need to have people supervising employees to ensure their jobs are getting done and the unproductivity of the 9-5 workflow made me decide to switch.

When you work remotely, you have to really trust your employees to work independently. These people are more focused on the tasks vs. people who just punch in from 9-5 to get paid and are unproductive. In a remote setting, the mindset is, “this is what I need to accomplish in order to get paid.”

As of now (the time of the interview), we have about 9-12 people who are working remotely full-time. They’re located in the U.S., India, Ukraine, Poland, and other European countries.

Aleyda: You mentioned before about this specific challenge, that when you’re working remotely, it may be hard to validate that the person is actually working since you can’t physically see them in the office. How did you manage to overcome this challenge with a team that is spread out all over the world?

Hamlet: It’s all about shifting the culture of paying people for their time to paying people for their work and outcomes. 

We organized the business around outcomes. We ask ourselves these questions: 

• What needs to be accomplished?
• Who can do it?
• When can they do it? 

From there we set a timeline to get it done. We also encourage continuous improvement by asking our team members, “I did it this way, but can anyone do it better?”

It’s a completely different mindset to operate a remote team. People are self-accountable and they can work whenever they want, where they want, as long as deadlines are met and the outcomes are great. 

Using the Agile methodology, we work in incremental “sprints.” When we have a project, we use Jira to break it down by who’s doing what. This system allows each process to be fully visible to the whole team and enables clear communication among us. Everyone can see each other’s workload so it’s easier to delegate tasks by who has time available.

In addition, we document each process using wikis and map out applicable training so that a formal procedure can be put in place for the future. This in conjunction with quizzes, projects, and certifications enables us to operate a more effective business that is result and outcome-focused versus time-focused.

Aleyda: I love that you mentioned two things: 

1. The cultural shift — Transitioning from getting paid to spend a certain amount of time somewhere to getting paid for specific outcomes or your productivity is something that we rarely hear. That continuous eight-hour timeframe we are given to “be productive” is not realistic any more.
2. The organizational shift — Being remote pushes better organizational practices of documentation, coordination, self-discipline, accountability, and transparency on what everyone is working on and the expected outputs.

When you hire new people, do they have experience working remotely? How do you prepare them to be a good fit for this type of work?

Hamlet: We typically do a mix. For example, right now we are experimenting with hiring local interns from the New Jersey area where we have our office and giving them the option to do both.

With RankSense, I started working from home for the first couple of years when my kids were small. Then, I started to find it difficult when my wife would think I’m not working since I was home. She would tell me to “do this”, or “do that,” and I couldn’t focus anymore. I used a company called Regus that I’ve been using for over seven years to rent a private office.

Even though I have to commute there, I still gain a lot. I’m a workaholic. At home, I would find it difficult to stop working especially since some team members have different timezones and often I would be up late at night working with them. It wasn’t healthy—I was sleeping very little and getting headaches often. I decided to just go to the office and only work when I’m there. It has helped me be much more productive with my time. 

I mention this office because we’re in the process of hiring local talent to help us with our socials and our blog. During interviews, I ask whether they would prefer to come into the office or work remotely. Often the response I get is along the lines of, “I live at school and can’t easily commute there. If I can work remotely, I can put in more hours.”

If you think about remote work, another thing we haven’t thought about is increased productivity. For traditional employees who go into the office, they consider the commute as part of their work since that is time they’re not doing things for themselves. By giving them that time back, employees often are willing to offer up more hours. 

My commute is only 10-15 minutes to the office, but I go there more for the purpose of isolation, to separate my workspace. I also go to local libraries sometimes where I can find more inspiration. 

Aleyda: At the end of the day, you have that flexibility. Often people ask me, “What about socializing with others? I can’t see myself working alone.” With remote work you have the control to ask yourself, “Where do I want to be?” and do just that without someone requiring you to be in a specific location.

Hamlet: I love the freedom that I get. I can go to New York, a cafe—I can work from anywhere.

Aleyda: What does your team prefer? Do you provide them the option to go to the office space you have or do they prefer to work from home?

Hamlet: They all prefer to work from home because of the flexibility it provides.

Aleyda: Until now, what is the biggest con you have found from working remotely? How have you overcome this?

Hamlet: My biggest frustration is the lack of constant communication with employees with respect to knowing when things are going wrong in their lives. I don’t know when they are going through a difficult situation in their personal life because they don’t tell you that though the chats. 

For example, we had an Executive Assistant working out of Arizona who was amazing in the beginning months but shortly began to downgrade her performance. We didn’t know what was going on. Unfortunately, we had to let her go since she wasn’t delivering on the things she had to do.

After letting her go, I was saddened to learn what was going on. She had a miscarriage and it was taking an immense toll on her mental health, as anyone would imagine. I felt so bad since I had already given her job to someone else. 

If I had known what was going on in her life, I would’ve tried to figure out a better way to deal with the situation like giving her some time away. If she would’ve been upfront with me that she was going through a hard time and needed a decreased workload, it would have been a different situation. With working remotely, everyone relies on each other’s accountability in order to keep that continual accountability with clients. 

That’s the hardest part. If you’re not meeting people face to face, you don’t know when they’re in good or bad situations. In a regular office environment, you can notice when someone is upset and ask them what’s going on. 

Aleyda: After that experience, have you decided to do anything different from what you’re doing?

Hamlet: I’m still figuring how I can work through this challenge. Prior to this, we have gotten all the employees together for a trip to New York. We had a very difficult 2017 and as a thank you, I wanted to bring everyone together to spend time as a team. Unfortunately, some team members were unable to get visas to travel to the U.S., so in the future, I’d like to plan a trip to Europe instead. I have people I’ve been working with for over seven years that I have yet to meet in person. 

I used to hate traveling—it made me very uncomfortable and threw off my energy, but I have gotten used to it just as I have with my speaking and writing. Naturally, I’m an introvert, but I’ve found a hack to get around this. 

I really enjoy programming and writing code. I use that as my excuse to do things that I don’t enjoy like traveling, speaking at events, etc. 

Aleyda: I like how you use the activity you really like as a vehicle to do the things you don’t.

Hamlet: With this hack, I’ve been able to increase the output of my written pieces and presentations at events. Before I would be too stressed to do these kinds of things but now I enjoy it since I’ve connected it this way.

I’ve been thinking of spending some time visiting my employees. I can meet with them in person while I’m traveling to build that personal connection.

Aleyda: Thank you for mentioning that. In general with the use of technology, we are losing that personal connection. We are all different and what’s critical is that we are accountable and acknowledge our own needs. Since we’re not pressured to be somewhere specific, it’s all on ourselves to do so.

Hamlet: Primarily, I just use my office to avoid distractions, but I do try to switch it up. I go to New York at least once a week or once every other week to meet up with friends and catch up. Nowadays, I’m spending a lot more time going to events.

I also attend a local chess club on Wednesdays and Saturdays where I have a good time with some guys. I enjoy taking my kids to activities and exploring things they want to see as well.

The one thing I wish I spent more time on is the gym. My whole family goes, but it seems I only make it there when I remember.  I still have to find a hack, like the one I found for speaking, that’ll get me into the gym. I love reading books and haven’t had the time recently to do that. I figure maybe I can use my love for books as an excuse to go to the gym by using Audible to listen to them instead. That way, I use something I really enjoy, books, to do something I don’t necessarily enjoy, going to the gym. That may be a way I can get there.

Aleyda: Besides Jira, what other tools do you use with your employees?

Hamlet: There’s a few. We use Slack for communication to keep everyone updated on what’s going on. Vimeo is another critical tool we use for training. We have our employees record a session with transcription and upload it to train somebody else. We also use the transcription as documentation to create internal wikis, it’s called Confluence, part of Jira as well. We also use Github as a code repository and Google Docs.

Aleyda: What would you say to companies that don’t believe in remote work? What tips do you have for companies who say it’s too challenging?

Hamlet: I think they have to start with a pain point. Most companies have a hard time finding top talent and that can be a main driver to consider remote. If you have a business in San Francisco or New York, you’re in a place where the competition for local talent is very tough and it’s hard to get really good people in your vicinity. One of the biggest things I think will move companies is acknowledging that you can hire the best talent across the globe if you have the right skills. 

That’s what I enjoy most. I get to work with amazing people that I can vet and ensure they are the best fit for the role no matter where they are in the world.

Aleyda: Thank you very much, Hamlet. 

Hamlet: Thanks for having me. I really enjoyed this chat and I’m looking forward to seeing you at another stage next year!

Aleyda: Looking forward to seeing you again soon!