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Richard O’Brien of Hoamsy: “Make everyone’s work and progress, visible to everyone else”

Make everyone’s work and progress, visible to everyone else. Transparency gets lost when we all retreat to our home offices and bedrooms for the workday. We found that by making everyone’s work accessible, and publicly tracked, it helps people understand where our company is at the time, where they stand in our timeline, and why what […]

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Make everyone’s work and progress, visible to everyone else.

Transparency gets lost when we all retreat to our home offices and bedrooms for the workday. We found that by making everyone’s work accessible, and publicly tracked, it helps people understand where our company is at the time, where they stand in our timeline, and why what they are doing matters.


We are living in a new world in which offices are becoming obsolete. How can teams effectively communicate if they are never together? Zoom and Slack are excellent tools, but they don’t replicate all the advantages of being together. What strategies, tools and techniques work to be a highly effective communicator, even if you are not in the same space?

In this interview series, we are interviewing business leaders who share the strategies, tools and techniques they use to effectively and efficiently communicate with their team who may be spread out across the world. As a part of this series, I had the pleasure of interviewing Richard O’Brien.

Richard is the Founder and CEO of the Boston based tech startup called Hoamsy. He leads the strategic and technical sides of the business overseeing the direction of the company as well as managing product development.

Background: Babson MBA Alumna, Class of 2020. B.S. in Mathematical Sciences with a minor in Business from Worcester Polytechnic Institute (WPI). Richard has previously co-founded two tech businesses — a social media platform, Litty and a mobile game app, Totem Tower.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I’d like to rewind to when I decided to go to grad school in Boston. I had a few months to move from New Hampshire to Boston and I thought a quick search online would lead me to my new apartment. I couldn’t have been more wrong. I wasted months wading through options only to end up paying thousands of dollars to an agent for an apartment that I didn’t particularly like. That was just the beginning of my woes as I realized that finding roommates and signing a lease were struggles in themselves.

So, as I sat in my first entrepreneurship class at Babson, thinking about the business I wanted to build, my thoughts landed on how much of a struggle my move had been. I had the experience of founding 2 tech platforms previously and I decided that for my next venture, I wanted to change the way people moved to make it less of a struggle. Now all I needed was a team. Soon enough, I met Nelly Lakshman, who faced exponentially bigger challenges moving from India to the US and Kaylin Goncalves, who faced the same challenges moving locally. Together, we went from an idea of making moving easier to the creation of Hoamsy. Hoamsy is a tech platform that makes moving easier by combining the search for apartments and roommates and everything in between into one seamless experience.

Can you share the most interesting story that happened to you since you began your career?

We started Hoamsy around March 2020, right when covid hit. We were forced to re-evaluate our startup on day 1. We thought we would get college kids returning to campus and large property managers, but covid caused both of those groups to go into complete turmoil. However, we found people who had lost roommates looking to fill rooms and nowhere to do so. That was our target group of Hoamsy back then.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My father advises a good path to follow is “always forward, never straight.” This means to always be seeking a path to better things and bettering yourself, but it doesn’t always have to be the straight and narrow laid out that everyone else has followed. Starting a startup in the middle of a pandemic is a great example of that, few would say this is the obvious straight path, like finding a standard job, but it’s a path forward, be it slightly unconventional.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’m genuinely grateful to my team and our interns. Nelly Lakshman and Kaylin Goncalves are strongest where I am weakest, and I could have never brought Hoamsy to the platform it is today without them. They are amazing at finding our messaging, understanding the customer, and helping our operations. Our Interns have been not only great additions to our culture, but they have taught us a lot about our business bringing in outside perspectives, as well as having been the extra pair of hands we desperately need to get work done!

Ok wonderful. Let’s now shift to the main focus of our interview. The pandemic has changed so many things about the way we behave. One of them of course, is how we work and how we communicate in our work. Many teams have started working remotely. Working remotely can be very different than working with a team that is in front of you. This provides great opportunity but it can also create unique challenges. To begin, can you articulate for our readers a few of the main benefits of having a team physically together?

Really uniquely, Hoamsy has been forced to be remote since right after the inception of our team, meaning our team has been born and bred completely digitally. Though we spent relatively little time in person, compared to digital, benefits include:

  • Easy Communication: it’s easy to find people, talk with them quickly, check in, not cut each other off, and overall read body language
  • More time together and understanding: In person people are only a few feet away, digitally, once the screen turns off, people are gone. Means you aren’t together as often, discourages collab a bit. Also, if you have a misunderstanding, less likely to go clarify digitally because it’s harder, to not only know you have one but also clarify it.
  • A certain “je ne sais quoi” — People often express how, “it’s easier to focus”, we feel “More in tune”, regardless of what it is, there is a definite effect on individual mindset when you are in person versus remote
  • Make All the points about the positives, negatives are the next question.

On the flip side, can you articulate for our readers a few of the main challenges that arise when a team is not in the same space?

First of all, you would feel less personal/human. People are just a screen because you don’t see them in real life, it can be easy to put less value on personal relationships and keep interaction to “just business”. Second of all, when we organize tasks and work together, it can be difficult to keep everyone on the same page with tasks without constant contact. Finally, when you go remote, the company culture would be affected because you lose micro interactions and there are limitations on group size etc.

Fantastic. Here is the main question of our interview. Based on your experience, what can one do to address or redress each of those challenges? What are your “5 Things You Need To Know To Communicate With Your Team Effectively Even If You Are Rarely In The Same Physical Space ? (Please share a story or example for each.)

1. 5 minutes making it personal, 2 times a day

  • One of the biggest challenges is the dehumanization of being trapped behind screens all day. Every day, we have at least two meetings where we check-in on work, and during those meetings we always take 3–5 minutes to talk about personal topics. News we saw that we think is interesting, does anyone have any plans, how are our pets doing, etc, etc.

2. Have Multiple Channels, not all for business

  • Having multiple channels of communication means that we facilitate more interaction between more people even if accidentally. One example is we have our siloed development and marketing meetings and slack channels, but also a general channel where all business updates get shared, and even a skincare channel for people on our team interested in sharing tips on that. It provides more ways to build relationships.

3. Be thorough in communication and constantly check

  • Many misunderstandings between teammates in digital communication comes from the inability to return to ask a follow up question. This means putting extra emphasis on answering questions before people part ways. Before any meeting ends, we always make sure to ask if anyone still has any questions.

4. Make everyone’s work and progress, visible to everyone else

  • Transparency gets lost when we all retreat to our home offices and bedrooms for the workday. We found that by making everyone’s work accessible, and publicly tracked, it helps people understand where our company is at the time, where they stand in our timeline, and why what they are doing matters.

5. Do a check-in

  • As a leader of a full remote team, I try to make sure I do a 1 on 1 check in with each team member at least once a month. There can be a tendency for things to get buried and for people to seem inaccessible when remote, but it’s important, especially in a leadership role to make sure everyone knows you are available for them, and ready to listen.

Has your company experienced communication challenges with your workforce working from home during the pandemic? For example, does your company allow employees to use their own cell phones or do they use the company’s phone lines for work? Can you share any other issues that came up?

Our company experienced 2 main challenges when building a remote team. The first challenge was lateness and webcams being off. We can all understand that it is tempting first thing in the morning to sit their sipping coffee with the webcam off, but it’s not respectful or productive. To resolve this we led by example, having our 3 founders always have our webcams turned on, and then politely asked people who would turn them off to turn them on, until it became a cultural norm. Additionally, it can seem inconsequential to be a minute or two late to a digital meeting, because you just pop in, but again it’s not respectful of others. So, we instituted a rule, that if you are late to a meeting you have to sing a song to everyone there that they chose. People immediately became on time, and it was a fun way of shaping culture.

The second challenge was a disconnect between marketing and tech, not being very clear on what the other was doing. To resolve this, we had 2 check ins a day lasting for about 5 minutes a piece where both the tech and marketing side would briefly talk about what they were doing often accompanied by a screen share.

Let’s zoom in a bit. Many tools have been developed to help teams coordinate and communicate with each other. In your personal experiences which tools have been most effective in helping to replicate the benefits of being together in the same space?

First of all, video conferencing has been the biggest tool in bridging the gap, we have multiple check-ins a day and often have people sitting in called working together. For better communication, we not only use video conferencing tools like Google meet, but also use Slack as our primary team communication tool, the ability to make separate channels is really powerful for organizing communication between parties and projects. Google Docs is our go to whenever we need to work on a project that involves developing marketing messaging or strategy discussion. And Trello is an excellent organizational tool that allows us to outline tasks, break them into checklists, assign members to tasks, create due dates and more.For the tech side, we need to do a lot of wireframing and design, Figma has been a great collaborative tool for creating designs.

If you could design the perfect communication feature or system to help your business, what would it be?

I feel like the perfect tool would be a little hologram of each member and their computer/work area. It would have all the efficiency of video chat and an ability to have VR interaction, so if someone needed to show you their work, you could really see it in real time, not just like a screen share. It would also have the more intrapersonal aspect of being in person, that the home office misses.

My particular expertise and interest is in Unified Communications. Has the pandemic changed the need or appeal for unified communications technology requirements? Can you explain?

I would say that Unified Communications, thought of as a suite of products, has been changed in the importance of integrations between them. We’ve seen products like Slack and Trello coming out with more integrations, but for a truly cohesive digital workplace, we need to not only be able to communicate on multiple different channels but be able to integrate them together. That’s one place the real-world still has a strong advantage, blending communication methods is easier and quicker if I want to, for example, show you details of a project and discuss its timeline in person, than it would be online.

The technology is rapidly evolving and new tools like VR, AR, and Mixed Reality are being developed to help bring remote teams together in a shared virtual space. Is there any technology coming down the pipeline that excites you?

For our business AR and VR are really exciting technologies as they become more mainstream. We are a moving platform, so being able to tour an apartment virtually in an immersive manner could mean game changing possibilities for our industry. That being said, there will always be limitations, for example, no photo, video, or even VR tour can tell you if an apartment smells like smoke.

Is there a part of this future vision that concerns you? Can you explain?

In a lot of ways a more connected world via AR, VR, and more could mean a less connected world. An ability to see anyone in VR also means less of a need to see them in person. There are certain intangibles to life that come with having face to face interactions that can be lost. But overall, I would say I’m more excited for the advancement and change, than scared of its implications.

So far we have discussed communication within a team. How has the pandemic changed the way you interact and engage your customers? How much of your interactions have moved to digital such as chatbots, messaging apps, phone, or video calls?

As our business was founded right at the beginning of the pandemic, we have built with fully digital in mind from the start. This means that one of our first tools was a chatbot for customers, as well as effective means of digital communication for people within our marketplace, like a messenger, adding video tours, and more. It’s also drastically effected how we prioritize for the next year, as we continue to consider — how we make someone make a high impact decision, like where they will live for the next year, in a fully digital context? How can we build in safeguards to protect against the inevitable shortcomings, and how can we be best available, even if it’s not in person.

In my experience, one of the trickiest parts of working with a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote team member?

Honest feedback can be difficult regardless of if someone is in person or online. For us it all comes down to culture. As a small team of less than 10 people, we focus on creating personal relationships, learning about each other as people, but I believe this can be done at all sizes. This means we take 5 minutes in the morning to ask people about their lives, webcams are always on when we are together, and more. With personal relationships, our team is more likely to be more understanding of each other’s work and feelings. Additionally, a major rule we have is to make actionable feedback. This means that we are not offering criticism, but improvements. We never say something is bad, we give feedback in the form of this is the improvement I’m looking for. I think these two principles are powerful in digital or in person, but we need to be more intentional about them in the digital world.

Can you give any specific ideas about how to create a sense of camaraderie and team cohesion when you are not physically together?

In my opinion, this is the most important aspect of creating an effective digital team. Here are some things we do to create a sense of camaraderie: We have 5 minutes of personal conversation at the beginning of day meeting and end of day wrap up. We also give people projects to work on together, even if sometimes they can be done alone. We have multiple channels of communication, we don’t make them all serious; For example, we use Google hangout, Slack, Trello, etc. We have a special skincare channel on Slack. We also give people the opportunity to bond with each other for one hour each week. For example, we have an event called Friday Fun on every Friday.

Ok wonderful. We are nearly done. Here is our last “meaty” question. You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

As an entrepreneur I think individual people have tremendous potential to create positive change in the world, just a number of factors often stand in the way. Fear of the unknown, self doubt, aversion to risk and more stop people from not only having their maximum impact, but also achieving their maximum happiness. If I could create a movement, it would be to have every single person start a business at least once. Even if 99% of them failed, having failed previously myself, I know there are a lot of powerful lessons to be taken from it, one the biggest being facing failure, and understanding there is nothing to fear. If everyone tried starting a business, just once, even for a month, I think it would have a powerful positive effect on the people and as a result the place we live :D.

How can our readers further follow your work online?

If you are looking for an easier way to find apartments or roommates around Boston or wanna know more about moving to Boston, welcome to our website: Hoamsy.com or shoot us an email at [email protected] . You can also connect with us on the socials, we are on Facebook,Instagram and LinkedIn!

Thank you so much for the time you spent doing this interview. This was very inspirational, and we wish you continued success.


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