Anthony Doctolero of GroupGreeting: How To Communicate With Your Team Effectively Even If You Are Rarely In The Same Physical Space

Reliable and Appropriate Communication Tools. Importance of Employee Recognition. Company Transparency. Setting Clear Expectations. Team Support Systems & Training.

Weare 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 Anthony Doctolero.

Anthony Doctolero is a serial entrepreneur and founder of GroupGreeting, a digital greeting card service that is paving the way for its fast, convenient, personalized and eco-friendly approach to group greeting cards. Prior to starting GroupGreeting in 2009, Anthony explored launching several other websites. He stepped away from GroupGreeting for almost 10 years to raise a family, but returned to the business in 2018 alongside his wife. GroupGreeting has since been featured in Fast Company, New York Magazine, Refinery29, while Anthony himself was recently awarded a spot in Forbes Next 1000 List.

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?

Absolutely, honored to be a part of this series. I grew up in San Francisco and started my career in sales and marketing, but I always knew I wanted to start my own business. After I got married, I quit my 9-to-5 job and created a start-up where we built several different websites, but none took off. Then in 2009, I received a package from my friend’s wife and inside was a birthday scrapbook for her husband that was being sent around our friend group for signatures via postal service. It reminded me of how team members pass birthday cards around the office in a folder for others to sign. I thought, ‘there has to be an easier way to do this,’ and that’s how GroupGreeting got started. The concept behind our service is that it easily allows groups of people to personalize a card, share it with others to sign regardless of location, and send virtually on any date and time selected. Shortly after launching GroupGreeting, I ended up going back to the corporate world because my wife and I had started a family. But year over year, the business was slowly growing. Fast forward to 2018, I noticed the rising trend of remote and hybrid work and thought those businesses could benefit from a service like the one I created so I decided to leave my full-time job in the tech industry and focus on growing GroupGreeting.

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

When the COVID-19 pandemic began in early 2020, we were down to our last $2,500 in the bank. At that time, cities across the country were beginning to issue shelter-in-place orders and people everywhere left the office to work from home. Over the following months, we saw something we had never seen before at GroupGreeting — a nearly 4,000% increase in usage. Corporations, nonprofits, universities and government agencies were all searching for a new way to celebrate remote employee milestones — birthdays, anniversaries, and holidays — and they found GroupGreeting. Within 5 months of the start of the shelter-in-place orders, GroupGreeting had become the highest traffic greeting card site on the internet, even surpassing industry leaders. By summer of 2020, nearly 80% of the country’s Fortune 500 companies were using GroupGreeting.

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

One of my favorite life quotes is “Live life with no regrets.” When I was working selling tv’s in college, I was helping an elderly man. He asked a lot of questions and I was able to help him find the right tv for him. At the end of the sale, he asked me if he could help me with anything. I asked him if he had any life advice for me as I was getting close to graduating. He said, make sure to live life to the fullest, and spend as much time as you can with family and friends. When you get to my age and you’re on your deathbed, you want to be able to say you lived your life with no regrets. That is why I named my company Stergeron as it spells “no regrets” backwards. It’s a subtle reminder to always remember that man’s advice.

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?

When I made the decision to work full time on my business, I knew it was going to be a huge challenge to make it successful. I knew I needed help and that I wanted someone who would bring other skills outside of mine to the table. I looked no further than the person I woke up next to every morning, my wife, Stephanie. She is humble, hard working, bright, and one of the best decision-makers I know. When you start a business, there are many things big and small to do. She did many things I didn’t have experience doing and we collaborated on solving many things together. Over the next year and a half, we were able to grow our business month over month. And by the time our business experienced explosive growth during the pandemic, we were ready to capitalize on the surge in demand for our business.

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?

I think the benefits of having a team physically working from the same space is that it encourages collaboration, which can also lead to quick and spontaneous idea sharing. Another beneficial aspect of being in the same space is that it aids communication. Much of communication is non-verbal and so solving problems together live makes it much easier to do this in person. When you’re in an office with colleagues, it’s also easier to recognize and provide support.

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?

Some challenges that arise from not working in the same physical space as your colleagues and employees is that there’s less opportunity to develop a human connection with your team and peers. There’s no water cooler chat about the weather, TV shows or upcoming deadlines. In addition, there’s an increased need for self-discipline, with the potential for more distractions at home, all while dealing with motivational challenges.

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. Reliable and Appropriate Communication Tools — It’s important to have reliable and dependable communication systems in place. Working remotely can present challenges interpreting tone in written communications, especially when you’re providing constructive feedback. At GroupGreeting we communicate frequently with our team via email, phone, and we use messaging systems like Slack, Zoom, and Google Meet to communicate action items, challenges, successes, company updates, etc. with our teams across the board. In addition, it’s equally important to know when to use each communication platform with each other depending on the sensitivity of the information that needs to be communicated. For example, if I am delivering good news or positive feedback to an individual, or the entire team, I will want to do that using a video conferencing platform. I want my team to see my excitement while delivering company wins. It’s important to know what type of message warrants a phone call vs. an email, vs. a video chat.
  2. Importance of Employee Recognition — Even if your company has gone remote or hybrid, it is important to acknowledge, motivate and recognize hard work among your employees. As a strong leader, you should identify what exactly motivates your team so you can incorporate relevant practices into your business. Anything from company bonuses, employee perks, to direct positive feedback for a job well done, serves as a great motivator all around. We even use GroupGreeting within our team to show appreciation for one another. It’s essential for employees to feel appreciated and recognized for their hard work. It boosts company and employee morale and ensures that your employees feel appreciated. Now more than ever, retaining valuable employees is an essential key to the success of a business.
  3. Company Transparency — When employees are kept informed of how the company is doing, it improves overall performance, so I try to make it a point to keep them involved in sharing company goals, feedback, successes and failures. During the pandemic, our company heard from many groups and businesses who needed our services because they could no longer be with friends, family and coworkers in person. Hospital executives and staff wanted to celebrate frontline workers, school principals wanted to send appreciation notes to hard-working teachers, students and their families, and companies wanted to show appreciation to valuable employees to keep them motivated during hardships, all with the help of GroupGreeting. As our customers shared these personal stories with me, I in turn shared them with my team. It was inspiring for them to hear about how their work was helping people stay connected and show gratitude and appreciation towards others. This led to a better understanding of customer needs and increased productivity.
  4. Setting Clear Expectations — Managing any team, whether remote or in a traditional office setting, begins with setting clear expectations. It is essential that each company employee is made clear of what responsibilities lie within their job description, and what is expected of them in their current role. There are several ways to ensure that employees are aware of manager expectations, such as employees can receive a written job description that they agree to during the hiring process, or perhaps there’s a virtual or in-person training where expectations are explained during onboarding. Regular meetings with team members are also a good opportunity to refresh expectations and ensure there’s understanding on both sides.
  5. Team Support Systems & Training — I touched a little on this subject above, but I am a firm believer that happy team members equal happy customers, which equals a healthy business. When your employees feel good about their work environment and are trained properly with all the tools necessary to complete their tasks, you get better overall results. It’s essential for employees to feel comfortable to ask questions when something is unclear. I would never want any of my employees to feel like they couldn’t come to me with anything. Another way to show your team support is to show appreciation. It’s a big part of our company culture here at GroupGreeting!

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?

The communication challenge our company faces as a result of working from home during the pandemic is more about us lacking the face time you would ordinarily get while working together in person daily. Our team has doubled in size throughout the pandemic and we’ve hired people we’ve never met in real life. Technology has enabled this, but being remote you lose a lot of the moments you’d normally get to build rapport amongst a newly formed team. We’ve had to build in meetups over video to just chat and talk about anything other than work. These have helped, but it’s definitely a tradeoff we’re still trying to figure out how to make it work best.

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?

We tend to use Google Meet or Zoom for larger group video meetings. They both have gallery views so you can see everyone in the virtual room and also have fun things like virtual backgrounds that can add some fun and personality to the meeting. For more immediate and ad hoc discussions, we use Slack as an instant messenger and their Slack Video feature is good for whiteboarding and collaborating together. For fun and team building, we recently provided everyone with an Oculus Quest VR headset. This allowed us to hangout virtually to play charades, paintball, and other games.

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

Many of the features are already out there, but they are just scattered across different services because some do things better than the others. If I could design the perfect communication system, I would combine Zoom’s UI and smooth handling of video, Slack’s real time messaging ability to be seamless across all devices, and Gmail’s rich email and calendar features.

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?

The pandemic has been an accelerant toward a more digital world. The digital transformation we were already experiencing was put on overdrive. The increased need for unified communications technology has been pulled forward by 10 years and it’s led to the need for further innovation in this area. Now more than ever it’s important to be able to communicate across different mediums and have it all sync up across different systems. It’s important for communication across a team as well as facilitating the speed of business. I can’t wait to see what new types of advancements will be made in the next several years.

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?

While we have experimented with doing team building via VR, it was mostly clunky and still not something that is turnkey enough to do regularly. That said, I remain bullish about the technology and can still see VR and AR being the future of how things will be done, whether it is a team building activity or doing a sales demo with a client.

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

As with many new technologies, there usually comes tradeoffs. The one part that I am concerned about having all this virtual activity is the likely loss or skill of in-person communication. Things like looking at screens all day may affect maintaining eye contact, or being bombarded with constant visual stimulation may lead to shorter attention spans in person. All these changes in how we communicate will just need to be balanced against what we’ve done and been successful at for many years.

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?

Since our product is digital and self-serve, naturally our communication with our customers leans much more toward digital forms. And I would say the vast majority of our customers expect and prefer to communicate digitally. We have a digital support desk to answer emails, and we frequently answer questions via Instagram or Facebook direct messages. When we have customers who are purchasing our service for their larger organization, we sometimes get requests for video or phone calls, but it’s less than 10% of the time. Doing things digitally helps maintain a paper trail that can be referenced later if necessary and more people can view the responses without needing to be there to receive the information. Overall, most customer interactions whether support or sales related can be handled more efficiently via digital forms, but live video or phone calls can help when a customer has a question that is more complex and needs more explanation.

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?

It’s challenging to give constructive feedback over email or instant messaging as it’s often difficult to identify or even convey tone via words on a screen. For this reason, I always recommend having these important conversations with remote team members via video or at the least, phone. The other key ingredients to providing constructive feedback remain the same as it is in person. It’s important to be specific, keep it positive, make the conversation an open dialogue so both sides are heard, and provide specific examples of the behavior being discussed. Above all else, be direct and respectful as the goal is to provide the feedback so both sides come away with clear understanding and can grow from there.

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

We’re still learning here and trying lots of different things, but of the things we’ve tried, here’s what has worked. During our company team meetings, we reserve a slide and time to allow for anyone on the team to voice their gratitude for another teammate. These have been great because it allows others to show appreciation for each other in a public way. We also do weekly snack chats for whoever is available to talk about anything other than work. It’s helped us to learn more about each other and find things in common which is helpful in building a supportive team environment.

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. 🙂

I would want to create a movement that helped make it even more commonplace to show gratitude for one another in the workplace. As you mentioned earlier, one never gets to the mountain top alone. This is true in the workplace as well and so to help create a movement that reminds people that gratitude is critical in winning is my mission.

How can our readers further follow your work online?

They can follow us on Instagram, @groupgreeting

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


Make and Receive Calls To/From
Hong Kong No Matter Where You Are