Calvin Rosser: “Be thoughtful with what you say”

Pay it forward. A now-deceased mentor of mine taught me about the value of helping others as you navigate life. No matter where you are in your personal life or career, you can find ways to help others improve the quality of their lives. Life is much more enriching when you help others, so don’t […]

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Pay it forward. A now-deceased mentor of mine taught me about the value of helping others as you navigate life. No matter where you are in your personal life or career, you can find ways to help others improve the quality of their lives. Life is much more enriching when you help others, so don’t wait until you’re rich and famous to start giving back. Find ways to pay it forward every day.

As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Calvin Rosser.

Calvin Rosser is the Director of Business Operations at Mechanism Ventures, a fully remote startup studio that helps founders fund, launch, and scale ambitious companies. He is also the Founder of Life Reimagined, an organization dedicated to helping 10 million people live a more conscious and fulfilling life.

Prior to his current roles, Calvin graduated from Princeton University and spent his early career as an M&A banker on Wall Street and a team lead at a 1B+ dollars fully remote staffing company.

Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

Hi, I’m Calvin! My story began in Orlando, Florida. My dad disappeared early in my life, and while my mom did her best, we lived an unstable existence with very little money.

I didn’t know how poor we were or how well other people lived, but I did know that I wanted a more comfortable and stable life. I despised the world of scarcity, and I committed to finding a way out. So I spent my early life figuring out how to improve my circumstances. I ended up getting a full scholarship to Princeton University and graduated with a degree in public policy.

After college, I joined a big investment bank in New York to find my financial footing. I worked on mergers and acquisitions for private equity firms across the automotive, healthcare, and consumer retail sectors. Wall Street offered a steady paycheck, but I didn’t enjoy spending 15 hours a day in a cubicle doing grunt work.

I knew there had to be more to life, so I looked for a new path. I ended up joining Toptal, a fully remote staffing company, in a growth marketing role. That experience hooked me on remote work and scaling companies. I spent the next few years growing Toptal, leading teams, and traveling to dozens of countries. I recently paused my travels to settle in Southern California.

For the last year, I’ve been the Director of Business Operations at Mechanism Ventures, a fully remote startup studio that helps founders fund, launch, and scale companies. I work on everything from launching growth channels, to improving internal operations, to hiring great people. I’m also the Founder of Life Reimagined, an organization dedicated to helping 10 million people live a more fulfilling life.

While I’m not sure where my career will take me, I’ve found a nice sweet spot for the time being. I spend most of my time writing, podcasting, and helping early-stage startups with growth and operations. It’s a lot of fun.

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

I’ve been fortunate to work with great friends throughout my career. In 2018, I hired one of my best friends to be my number two. I convinced the company to fly him to Croatia to meet me for onboarding. We spent the next month onboarding him to the role while traveling through Croatia, Montenegro, Bosnia, Serbia, and Hungary.

Getting to travel the world and work with your best friends is so much fun. It adds a lot of meaning and joy to work, and I wouldn’t trade those experiences for anything.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I left banking to join Toptal’s growth team, I found the work incredibly engaging. I was learning the fundamentals of growing a business, and within a few months, I was managing tens of thousands of dollars in ad spend, managing a small team, and getting paid very well. The autonomy, pace, and practical nature of growth marketing work felt so much better than investment banking.

When I got my first performance review 6 months after starting, I learned that my colleagues thought I was far too serious. Someone said something like, “You do a great job of growing the business, but it’s important to remember that we’re not all APIs that focus only on results. You’re working with people.”

That feedback taught me an important lesson. I learned that fulfilling your core job function is not enough. You have to build meaningful relationships with your colleagues. From that point onward, I’ve spent a lot of time connecting with colleagues outside of just getting work done. This increased focus on relationships has served me well as I’ve moved from individual contributor to team-management roles.

What advice would you give to other CEOs or founders to help their employees to thrive and avoid burnout?

While it’s easy to expect people to manage their own energy, they often don’t. No one wants to seem like they’re struggling, so they often hide their struggles.

As a leader, it’s your responsibility to understand each individual and how that person may end up on a path to burnout. To do this well, you need to understand what motivates each individual, what triggers them, and how to create a psychologically safe environment for people to discuss challenges.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

I’ve managed remote teams across Growth, Operations, and Community for four years.

Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each?

Aligning a global team.

With the proliferation of remote work across the globe, it’s increasingly common to work on teams of people who don’t share a common location, time zone, culture or language. In this context, it’s much more difficult to align, motivate, and engage such a diverse group.


There are endless requests, messages, and things to do in the remote world. But as a leader, your mission is to drive results that translate your vision into reality. To do that well, you need to avoid the fallacy that everything matters equally. Multitasking and task-switching are ineffective and inefficient. They cost your team valuable energy, time, and results.

Digital miscommunication.

Because we aren’t physically present with colleagues in a remote working environment, we have fewer cues to understand the intent of our colleagues. So when we receive a Slack message or hop on a Zoom call, we’re more likely to misunderstand the intention and tone behind the message. If we assume mal-intent when there is none, that can cause unnecessary strain on working relationships.

Cultural differences.

In remote working environments, it’s common to work on teams of people with very different cultural backgrounds and values. For example, I’ve managed teams that span multiple continents and operate in over 75 countries. This environment is ripe for communication gaps and misunderstandings.

Managing burnout.

In a traditional office environment, it’s easy to rely on physical cues to sense when a team member is burning out, unhappy, or getting ready to quit. But in a remote environment, the lack of in-person contact means that you can easily miss these important signals. For instance, you don’t see the physical signs (baggy eyes, unwashed hair) or body language (rolling eyes, folded arms) that can indicate a person is burning out or unhappy.

Based on your experience, what can one do to address or redress each of those challenges?

Aligning a global team.

Good storytelling can help solve this challenge. Stories are an ancient art form that helped us survive and bond for thousands of years. Across time and cultures, stories have been used to educate, entertain, and engage people.

Because stories engage our emotions, they motivate us to feel and take action. They have the capacity to change attitudes, beliefs, and behaviors in ways that no other medium can. In an increasingly data-driven world, many leaders turn to logic and data to align, motivate, and persuade others. Without realizing it, these leaders are doing themselves a disservice. Because while facts and figures should certainly inform our decisions, they don’t make us feel. And if we don’t feel, we simply don’t care.

So to align a global team, build a culture of good storytelling. For example, lead with a story in every presentation. That can be a story of your vision, a story of something another person did, or a story of something you found interesting. You can also implement dedicated “storytime” on team calls. Have a rotating schedule and allow people to tell a story. When you see an initiative that went particularly well or something a teammate did that you want others to do, prompt the team to talk about it.


High performing leaders of remote teams have an eye for the essential. In a remote environment, the contribution you provide to the team and organization is far more important than the hours you spend working. Results stem from doing the right things, not doing things right. Effectively managing in a remote environment requires you to empower your team to prioritize and execute on the initiatives that deliver the most business impact.

As a manager, ask yourself and your team every day, week, month, quarter, and year: “What’s the one thing I can do such that by doing it everything else will be easier or unnecessary?” Ruthlessly prioritize that one thing and encourage your team to do the same.

Digital miscommunication

Digital communication provides us with fewer cues to understand the intent of our colleagues. Intent is important. It makes us feel safe with colleagues and helps us accurately interpret the information we receive. To mitigate the risk of intent issues in communication, you should:

  1. Be thoughtful with what you say. Before you send a message, try reading it from the perspective of the person receiving the message.
  2. Use emojis to soften the anticipated sting of an email or message.
  3. Meet face-to-face at least once if possible.
  4. Avoid sending a long wall of text: Record a quick video and send that instead.
  5. Ask people to clarify: “Sorry, I don’t think I understand, can you clarify?”

These techniques are not perfect, but they help.

Cultural differences.

To lead a global team, you need to understand how different cultures view work, think about feedback, treat hierarchy within organizations, and so on. You’d be surprised by how the place in which you grew up biases you to think about work in narrow ways.

Outside of learning through experience, read The Culture Map by Erin Meyer. It’s a great book that explores the many ways in which communication differs across cultures and how we can bridge the gap. This book will give leaders a head start on avoiding some common mistakes.

Managing burnout.

I mentioned this earlier, but you need to understand your people — what motivates them, what makes them unhappy, what they want out of work, what they’re dealing with in their personal lives, and so on. You can do this by getting to know people through conversations that focus on topics outside of day-to-day work projects.

If you think someone is approaching burnout, have a conversation with them. Start by asking questions and listening. Never assume anything about what’s causing the problem. The problem can be anything ranging from too much work, to a specific roadblock, to a personal health issue, to working on the wrong types of projects.

Once you understand the problem, you can offer specific solutions. The solution may include helping them to solve a difficult roadblock, offering tools or resources that may help, or getting them on new projects that align with their career goals. You can’t offer solutions until you understand the problem from the employee’s perspective.

Finally, you need to make people feel psychologically safe. If someone thinks they will be fired for having a bad week at work, they won’t feel comfortable talking about their struggles. You need to let people know that it’s okay if they need some extra help or time to step away.

In my experience, one of the trickiest parts of managing 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 employee?

You need to build a genuine culture of feedback and continuous improvement. There are many ways to do this, but an essential component is creating psychological safety for people who are giving and receiving feedback.

As a leader, you need to set the tone. Proactively ask for feedback. Talk about your mistakes openly. And never punish anyone for giving feedback. For example, imagine I just gave a big presentation as a leader. One of my teammates who worked with me on the presentation comes up afterwards and says:

“Hey, great presentation — I think it went well overall. About halfway through, I think you could have stated [x] more clearly and responded to the questions from [y] with more information.”

If I want to foster a culture of continuous feedback and improvement, I need to be careful with my response. The correct response is to thank the person for the feedback, ask clarifying questions, and change my behavior over time if it makes sense to do so. With this approach, the person will feel safe giving me feedback again.

If I start dismissing the feedback or justifying why it’s wrong, I won’t ever get feedback again. The person won’t feel that I’m actually open-minded and won’t go through the discomfort of providing me more feedback in the future.

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

Whenever possible, I recommend getting on a Zoom call instead of giving feedback over email or Slack. But if you can’t do that for one reason or another, I use the following structure — start with a soft intro, mention something good, note the area for improvement, explain why, and demonstrate appreciation.

For example, imagine one of my teammates sent something unprofessional to a client. I might say something like:

“Hi, hope your week is off to a good start! I liked how proactive you were in reaching out to the client. That’s an important account for us.

I noticed in your message that you included a link to a politically-charged Youtube video in your last email. While I think it’s great to connect with clients on a personal level, we generally try to avoid politically-oriented content with clients. We’ve had a few bad experiences with this in the past, so as a general best practice, we avoid discussing politics with clients.

Appreciate you working so hard on growing this account. We’re close to reaching new milestones with this client thanks to your dedication and work.



If you’ve built a culture of feedback and continuous improvement, this message will be received well.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic. Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

Try not to get paralyzed by information overload. Slack, Zoom, Trello, and other companies have made digital collaboration frictionless and cheaper. While these tools enable seamless remote work, they also come with lots of messages and alerts that can make it easy to get overwhelmed with information.

The speed of information can be overwhelming, and in some cases, paralyzing. So finding a way to filter through the noise and focus on what’s truly important is an incredibly valuable skill for the long-term.

What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?

Encourage people to create separation from work. When you go in and out of a physical office, there’s a natural separation between home life and work life.

With the flexibility of remote work, you can open up your laptop and work at any point in the day. So while you can enjoy an afternoon nap or workout without anyone shaming you, you can also find yourself working at ten or eleven at night from my couch.

In this new environment, you have to help people create healthy boundaries between work and life so that they don’t burnout.

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. 🙂

Pay it forward. A now-deceased mentor of mine taught me about the value of helping others as you navigate life. No matter where you are in your personal life or career, you can find ways to help others improve the quality of their lives. Life is much more enriching when you help others, so don’t wait until you’re rich and famous to start giving back. Find ways to pay it forward every day.

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

With respect to good leadership, I often revisit a quote from the founder of Walmart, Sam Walton,

“Celebrate your success and find humor in your failures. Don’t take yourself so seriously. Loosen up and everyone around you will loosen up. Have fun and always show enthusiasm.”

I have the tendency to accomplish goals and not celebrate them. I often take mistakes and failures too seriously. And I certainly don’t have enough fun on the journey.

Walton reminds me that life is too short to operate this way. Life and business are a lot more fun when you celebrate more, show more appreciation, and don’t take mistakes too seriously.

Thank you for these great insights!

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