Sammy Courtright of Ten Spot: Five Things You Need To Know To Successfully Manage a Remote Team

Celebrate/Reward/Recognize: running an early-stage startup means you constantly balance celebrating quick wins and road mapping long term plays. To ensure that we celebrate both, we have a #cowbells channel in Slack where teams post their monthly and quarterly goals, accomplishments (big or small) and celebrate them together.

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

Hailing from Australia, Sammy Courtright is the co-founder and Chief Brand Officer of Ten Spot, an all-in-one platform that helps companies connect, engage, and manage remote and on-site employees.

After finding it frustrating to stay healthy in a typical 9-to-5 environment, Sammy and her co-founder, Jonathan Cohn, teamed up in 2014 to create Fitspot, whose mission was to deliver wellness where employees needed it the most — at work. Renamed Ten Spot in 2020, the company not only rebranded to expand beyond wellness, but now offers a centralized solution for companies to increase their productivity, boost retention, and build a strong culture.

When COVID hit, Sammy learned that customers were facing a similar issue: how do we ensure employees feel like they work for the same company when they are not in the same place? Through research, she discovered that leadership was struggling to manage distributed teams. This led to Ten Spot’s expansion to the workforce engagement platform it is today.

With a BA in Fine Arts from the University of Miami, Sammy is a certified Pilates instructor who brings a blend of grit and imagination to the zillions of tasks that confront every startup. While she wears many hats, Sammy’s passion for building culture has created an atmosphere at Ten Spot dedicated to positive thinking and collaboration.

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”?

I’ve always been very creatively inclined, and in school, I studied theatre. However, at the same time, there’s always been part of my brain hyper-focused on solving problems.

Anytime I go into a restaurant or a store, I find myself thinking about all the ways it could be more efficient and scalable, and have even emailed the owners with my ideas (I know, I am that person). That is how I met Jon, my co-founder. Mutual friends introduced us and once I heard about what he was working on, I started telling him all the ideas I had to make it scale.

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

In our first few months of existence, an engineer who worked for us hijacked our entire code base and held it for ransom for 45 days. We learned, after the fact, that he had created a segment of the code using his personal email address rather than his work email address.

For 45 days, we literally had no insight into the product. We didn’t know who was using it or if there were any bookings–nothing! With legal assistance, the issue was ultimately resolved. It was a jarring (and slightly expensive!) lesson for us when it came to safeguarding and protecting the company’s intellectual property.

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?

Last fall, I was sitting in a cafe in New York, having a cup of coffee, and some guy I’d never met before approached me and said, “Sammy?” I was thinking, “I’ve never met this person before…right?” and replied, “Yeah?” And he said, “Ten Spot, right? My friend’s cousin sent me your pitch deck.”

Moral of the story: your pitch deck isn’t your business card. We always prefer it when people ask to share company collateral before sharing it with others!

What advice would you give to other business leaders to help their employees to thrive and avoid burnout?

This pandemic has put employee mental health front and center for most organizations. Research shows more people are putting in excessive hours at work and experiencing increased burnout because of the inability to separate personal and professional lives.

One of Ten Spot’s goals is to reduce employee burnout, and we’ve taken steps to optimize and improve our employees’ mental wellness and work with different schedules. For example, our live meditation, stress management, and fitness sessions are available at a wide range of times and then recorded, so they’re available to watch through our on-demand library.

The stigma around mental health and speaking up about stress at work, combined with concerns of economic instability, means we’re far from normalizing mental health conversation in the workplace. We’ve worked hard to ensure Ten Spot’s programming offers a breadth of variety for people to become more educated around this critical issue and build up their communication skills to advocate for mental health in the workplace. We’re providing the tools to talk about mental health at work — for our customers, internal teams, and in time, to extend this out more broadly — to help provide a safe space for those struggling and create a positive and open culture.

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?

Ten Spot has been managing remote teams since 2016.

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?

Onboarding: Many of us are hiring, onboarding, and training employees that we haven’t met or might not meet in person for a long time. Let’s face it; it is awkward for both the new hire and the employer.

Employee Connections: Think about all the interactions you have when you’re in person. Working remotely means we’ve lost a little spontaneity — those casual conversations that happen desk-side or while catching up over snacks or at the coffee station. Ten Spot recently conducted a national survey about employee productivity and engagement during COVID-19, and 52% said that they feel less connected to their colleagues right now. Those day-to-day conversations add up to build relationships between peers, strengthen teams, boost camaraderie, and help create happy and engaged workers. The focus now is how to recreate those moments virtually.

Company-Wide Events: When employees are remote, team-building events quickly fall by the wayside. There are many hurdles to overcome like Zoom fatigue, coordinating the events, finding the hosts, marketing it, and it may feel like a lot of work, but the upside is it can shape your culture.

Celebrate the Small Wins: It is easy to gloss over small wins when teams are remote, but more than ever, employees want to feel seen, heard, and recognized. If it feels like a hassle to get everyone together to celebrate, or you feel like you’re interrupting workflows with something that ‘doesn’t feel important,’ remember it is all-important.

Mission and Goal Alignment: This also aligns employees with their purpose. What are they here to do? Why is their success critical to the company? When everyone is remote, it is hard to gauge whether employees feel connected and are driving towards the same goals.

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

Onboarding: There is a need to recreate a way for employees to truly connect in a virtual world. When you begin to work for a company, you typically are introduced to a team, have the opportunity to share interests, join town halls and all-hands meetings. When you’re fully remote, you do not have that option. So how do we go about creating these connections? How do we recreate a lot of what we do when we are physically together, now virtually?

Many of the interactions that help you get to know the team and specific individuals come on a micro level such as chats by the coffee machine, elevator chatter, happy hours. One of the best ways to recreate this digitally is to enhance tools that employees are already using. From Microsoft Teams to Slack or Google chat, whatever you use, enhance what you’re working with as it is already a part of the fabric of your organization.

Employee Connections: The number one thing to remember is that you’re building a foundation for remote employees to have new relationships in the workplace and helping them to have a voice, which is even more important when they are remote. Are you creating these micro-moments of belonging? Are you helping to create empowering environments that allow employees to stay connected and collaborate?

Company-Wide Events: Ten Spot’s recent survey revealed 60% of the most productive and engaged workers are frequently offered virtual social work events during COVID-19 — and whether it’s a virtual trivia night, a cocktail crafting class, a scavenger hunt, a 15-minute group meditation — we’ve found the most success when these events happen consistently. Ideally, these are non-work-related events or experiences which means try to reduce the work-specific talk and encourage dialogue that will get people chatting.

We encourage all employees to turn their cameras and mics on. The best way to connect with someone is when you can see their face and make eye contact. And for any new hires attending for the first time, encourage people to introduce themselves with their name and department.

Celebrate/Reward/Recognize: Running an early-stage startup means you constantly balance celebrating quick wins and road mapping long term plays. To ensure that we celebrate both, we have a #cowbells channel in Slack where teams post their monthly and quarterly goals, accomplishments (big or small) and celebrate them together.

Mission and Goal Alignment: We communicate our company mission and strategy in every all-hands meeting. As a company, we focus on about three to five key metrics per department. These are measured quarterly but reviewed monthly. But we’ve also found short term goals to be successful.

We’ve found that 30-day goals force the team to be more action-driven and laser-focused on results. And most of the time, they implement a strategy that goes far beyond the 30 days removing the fear of it only being a 30-day initiative. It also is a really fun way to remind the team to celebrate small wins. We write the goals in Slack on the first day of the month, we bring them up in each weekly meeting, and on the last day of the month and we tell each other what actions we took and the end result. A few people have actually described it as ‘fun’ which is great!

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?

First and foremost, set the intention. Make it clear that this is a private call to provide feedback. Secondly, make it a video call where both parties have their cameras on. Then the employee can see your facial expressions and (shoulders up) body language.

Regardless of whether the employee works remotely or on-site, I follow a couple of key points outlined in the book ‘Thanks for the Feedback’ by Douglas Stone and Sheila Heen.

Before the meeting, I ask myself: am I trying to approve, assess, or say thank you? Depending on the answer, I can provide three types of feedback: appreciation, coaching, or evaluation.

Finally, I need to clearly understand what is my purpose or intention in giving this feedback. Is this to keep everyone on track? Is it to form a better understanding and relationship? Am I sharing this information to contribute to my employees’ professional development?

Answering this shapes the conversation and ensures we have a productive and clear conversation.

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

Giving feedback is a delicate interaction and sharing it over an email is tricky since there aren’t social cues to read. The most significant point to remember is to deliver the feedback with tact and humility.

It also means paying attention to your tone and upgrading the positivity of your language. It’s easy for someone else to read between the lines and interpret them from their perspective.

An excellent structure to follow is to start by showing appreciation at the beginning of the email, which infers that you appreciate some aspect of the work they have performed. Then provide the actionable and specific feedback you have to share. From there, it’s essential to focus on how you can move forward and finally highlight the progress that has been made.

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?

Treating this as business as usual. This is a unique situation, a global pandemic, where people are stressed about their health, their families, their kids, and their job. It is important to understand what employees are dealing with. I recommend communicating frequently to let your team know you are supportive and understanding of the circumstance.

Avoiding phone calls. Emailing, Slack, Teams, etc. are great but tone can get confused in text. Do not hesitate to pick up the phone to clarify a point or just to catch up with a colleague. When we were in person, when you walked by someone’s desk en route to the coffee machine, conversations would naturally occur. For some reason, the thought of calling someone on their cell phone can feel invasive but it’s a great way to effectively communicate.

Waiting for things to go ‘back to normal’. The hybrid workforce is here to stay. Proactively invest in technology that will enable your team to communicate and collaborate effectively whether they are on-site or remote.

Overloading teams with too much information. Whether we have Slack notifications turned on all the time because we’re afraid of missing an important message, or our phone notifications on for all apps, too much of something that is beneficial or useful can be harmful or even excessive. Some of the engaging aspects of digital technology and tools may even be addictive so it’s critical to make sure teams recognize this and we’re sharing ways to avoid information overload — this means encouraging time-outs from email pings or turning off notifications while working on tasks or projects that require deep focus.

Not normalizing time off
Employees who believe working from their phone during a family meal is the norm — or even expected — may not prioritize time away from their tech. But when team leaders make a point to overtly show they support a healthy work-life balance and praise employees for only working during work hours, they create an environment where everyone feels more comfortable stepping away from their phone and computer when they finish the workday.

Not supporting a digital detox
Taking regular breaks is critical for maintaining mental health. Offering employees the opportunity to sign a pledge committing to reduce any unhealthy tech habits can go a long way toward encouraging a healthy work-life balance. As a remote team, you can keep each other accountable by creating a pledge that includes specific steps to complete, such as a week-long digital detox to follow.

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?

Celebrate/Reward/Recognize: running an early-stage startup means you constantly balance celebrating quick wins and road mapping long term plays. To ensure that we celebrate both, we have a #cowbells channel in Slack where teams post their monthly and quarterly goals, accomplishments (big or small) and celebrate them together.

Flexibility: if 2020 taught us anything, it is that a hybrid workforce is here to stay. Employees are looking for job flexibility with the ‘it doesn’t matter when or how I do the job, as long as I get it done’ mentality.

Transparency: Antiquated communication tools can be a massive barrier to transparency. If you haven’t already, this is the time to improve your communication and collaboration tools, especially as distributed teams are the future. An investment in enhancing tools ensures that teams have an easy and efficient way to connect and share information, from successes to the, more importantly, the challenges. You might find that transparency leads to the team coming up with solutions together.

Purpose and passion: When you’re interviewing for a job, it’s essential to ask yourself: do you feel connected to the company, its mission, and the team? Are you excited about the problem you are solving? I’ve found it’s crucial to reiterate Ten Spot’s core values and mission in every all-hands meeting as it reminds everyone of what we are here to do. People tend to move to other opportunities when they feel like they are no longer challenged or excited by what the company is doing.

Strong co-worker relationships: We all know that when employees enjoy where they work, they want their friends to work there too. Referrals are a great way to increase your talent pool. Creating a culture that people want to be and stay a part of reduces employees running after the next best offer. Friendships in the workplace are an essential part of the equation. Whether it’s peer-pairing, mentoring, or team-wide virtual events, it’s crucial for employees to connect with each other to connect with the company.

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. :-)

I value education, and I don’t believe that learning should stop when you leave school. I recently read a report that said to remain relevant in the workforce and your job, you need to be learning and developing new skills at least every four years. This creates one of those challenges that I’d like to help solve, starting with Ten Spot’s customers.

Going back to school is expensive, and it usually doesn’t keep someone in the job market while attending, meaning learning and skill development needs to either occur on the job or with your employer’s support.

We are in the process of rolling out peer-to-peer learning on Ten Spot’s platform but envision it going beyond mentoring and expanding into important skills training. This can start with live sessions that are ultimately recorded and archived for use by new employees or anyone needing a refresher course.

I feel if we can help companies do this across the board, we’re helping make education more accessible. Employees can then learn and develop new skills without sacrificing their jobs and without their employers losing them.

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

“Life is inherently risky. There is only one big risk you should avoid at all costs, and that is the risk of doing nothing.” — Denis Waitley.

It is not easy running an early-stage company. I am, ironically, quite risk-averse. This quote reminds me to always take the plunge, make the tough decision, and speak up because any path taken involves risk.

Thank you for these great insights!