Tony Perlak of Continued: “Trust ”

Trust — When at work, trust is such an important dynamic. Two common approaches for trusting others is to give trust out of the gate or to make others earn your trust over time. While different approaches certainly work for different people, the former — trust from the get-go — is paramount to succeed in forming meaningful and productive relationships with […]

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Trust — When at work, trust is such an important dynamic. Two common approaches for trusting others is to give trust out of the gate or to make others earn your trust over time. While different approaches certainly work for different people, the former — trust from the get-go — is paramount to succeed in forming meaningful and productive relationships with your colleagues in a remote setting. Without being physically present, you have to trust that your team members are present, productive, and accessible, or you will drive them (and yourself!) crazy.

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

Tony Perlak has over 25 years of experience as a highly accomplished and knowledgeable executive with profit and loss responsibility as well as extensive expertise in marketing strategy, product development, direct response, pricing and promotions, and financial planning and analysis across various subscription businesses. As Chief Executive Officer of LaCalle Group, the parent company of Continuedand Simucase, Tony is responsible for strategy, growth, and culture across the businesses.

Tony previously served in various marketing and finance management roles across a variety of industries with companies including Lockheed Martin, AT&T Wireless, Gate Gourmet, Nutrisystem, and Vonage. Tony holds an MBA from American University’s Kogod School of Business and a BA in Psychology from Bates College.

Tony lives in New Mexico with his wife, two kids, and two dogs.

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”?

It’s always fun to look back at my journey because there was no plan or linear, predictable trend in the points along the way — it really was more of a scatterplot with no correlation in the variables. I started working at a very young age at my uncle’s nursery and was convinced into my early twenties that I wanted to start up and run a garden center in New England. That changed upon graduation from college, as social work became my chosen profession until I pivoted into a pricing role in the wireless industry. This was the start of various roles in various industries in companies of varying sizes and in various departments! The common thread along the way was jumping at an opportunity — even if it seemed disjointed from my experience — if it posed the next challenge for me and made me both excited and nervous. My family has also been an equal partner in the process, so if a move to a different job or city wasn’t right for them, or the opportunity would have an adverse impact on them, we would pass.

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

I don’t know if it is the most interesting story, but it is certainly the most impactful! My first job out of college was working for a district attorney’s office in Massachusetts as a victim/witness advocate, a liaison role between prosecutors and the victims and witnesses of violent crimes. After a year on the job, I thought I had my sea legs and was doing quite well in the role, but I resigned because I had made the decision to move to the Washington, DC, area for work and graduate school. When I resigned, the director of the program said, “that’s a shame — in about three to five years you would have made a good advocate.” I thought about that comment during the entire seven-hour car ride to DC and ever since. It was a great lesson at a young age that you don’t know what you don’t know, and you can always keep learning and improving.

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?

After I moved to Washington, DC, I was working full time and attending grad school at night. That was an exciting and fun combination for the first year, but in an effort to complete my degree sooner, I started loading up with more classes and was taking the equivalent of a full time student load in addition to my job. Needless to say, I didn’t get much sleep for an extended period, and it took its toll. One night I got to school, grabbed my backpack from my car, and went to class. After classes and a study group, I walked back to my car and couldn’t find my car keys anywhere. As I got closer to my car, and with my friends making fun of me the whole way, I thankfully saw the keys sticking out of the driver’s door. I was relieved that the car wasn’t stolen out of a metro DC parking lot but then saw that the change had been taken from the ashtray and all my sporting equipment was stolen from the trunk. It was admittedly a small price to pay for such a careless mistake, and it taught me this: If you feel like you have taken on too much, and you are losing the basic ability to function as a result, you need to immediately reprioritize and simplify, or you will fail at everything. As humans, we are generally not good at recognizing our own boundaries or limits, but they do exist, and being aware of them is an enormous asset.

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

For me, two key strategies to help deal with stress are to ensure that I devote time to interests outside of work and embrace that it is OK to take breaks throughout the day to step away from my desk. I love to trail run here in New Mexico and hike with my wife and our two dogs. When time gets short, those are often the easiest activities to sacrifice, but they are also the ones where I have some of my clearest thinking and can work through business problems as I exercise or discuss them with my wife, so keeping them in the schedule is essential. As for breaks throughout the day, it is as simple as stealing a few minutes to walk the dog if you work from home or walking around the corporate campus in an office environment. Similar premise, those few minutes change your scenery and can allow you to shed some stress or even free up your brain to think of an issue from a different perspective.

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 just celebrated my six-year anniversary at LaCalle Group, and all six have been in a 100% remote work environment, which the company has operated under since its start in 1999. Prior to that, I spent 20 years at traditional brick and mortar corporate settings with large companies, but even that always involved collaborating with team members in various field sales offices or satellite facilities to get important work accomplished.

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?

As I spend more time in a remote setting versus an office, I have to admit that the challenges of managing a remote team have really blurred with the challenges of managing a team that you physically spend time with every day. If you take the setting out of it and focus only on the challenges and solutions, they are the same challenges and solutions; they just sometimes take some adaptability to better navigate through them in a remote setting. Here are five challenges that I have experienced:


When at work, trust is such an important dynamic. Two common approaches for trusting others is to give trust out of the gate or to make others earn your trust over time. While different approaches certainly work for different people, the former — trust from the get-go — is paramount to succeed in forming meaningful and productive relationships with your colleagues in a remote setting. Without being physically present, you have to trust that your team members are present, productive, and accessible, or you will drive them (and yourself!) crazy.

When the work gets done

In an office setting, it is easy to keep tabs on the progress of a project or even drop by and ask a colleague what they are working on that day. But in a remote setting, the random “bed check” can only be achieved through a ham-handed Slack message, which leads to the real question: Who cares when or where the work gets done as long as it gets done and gets done well? That was a mindset change for me when moving to a remote company. I also quickly identified that such questions were purely done out of habit, not purpose, so it was easy to stop!

Body Language (or lack thereof!)

In a past life, I was offered an opportunity to shift from a finance leadership role back to my beloved old discipline of a marketing leadership role, but during a time of duress at the company. Results for a key selling period were not what we needed them to be, and there were layoffs and some voluntary attrition, so my first meeting with the team was not under the best of circumstances. As I started my prepared notes, every set of arms in the room were either crossed or they were holding a phone as people texted each other in the room. Needless to say, the prepared notes got tossed out the window immediately because these visual cues told me everything that I was about to say to this audience was obtuse. In a remote work environment, we sometimes have the benefit of a video during calls but not always, and as the participant counts mount, you cannot simultaneously present and scan the Slack “Brady Bunch squares” for 20+ people to change your message on the fly!

Defining culture

This is my favorite challenge, because the answer can be simple, but it took a remote work environment for me to realize it! In many of my previous companies, culture was discussed a lot, but it was also completely subject to the ebbs and flows of the P&L. When times were good, culture was trumpeted! When times were bad, culture was marginalized. But through it all, “culture” was a single rallying cry or premise that everyone had to buy into, or in some cases, conform to. At LaCalle Group, we have turned that on its head a bit in that culture is not one thing that 138 people need to buy into, print out, and post on their office walls. Rather, culture is the contribution, individual identities, and uniqueness of our 138 team members and how we treat each other, and recognizing that each addition to our team adds to our culture with a new perspective. Implicit in this approach is allowing a degree of vulnerability, and back to the first point above, it requires trust.

Forming personal connections

During my time at LaCalle Group, I have heard many colleagues say that they are closer to their work family at our remote company than they ever were in an office setting. Alternately, I have also heard folks say that they have struggled to form personal connections with their colleagues, especially during the pandemic in 2020, when travel and all face to face meetings were cancelled at our company. It’s important to focus on connection in any workplace environment, but this importance can be magnified in a remote setting and takes an extra dose of creativity and intentionality to make it happen.

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

Going back to the idea of trust: Early on in this role, I would frequently hear the term “vulnerable trust.” Based on my experience, I received the term with a fair bit of skepticism, as being vulnerable in any way in past work environments would have carried significant risk! But at its core, if you are able to embrace the idea, and believe in yourself and in others, each of the challenges listed above can be overcome. Trust that the team will get their jobs done, even if they are walking their dog for 30 minutes at 10 in the morning or attending a yoga class at 2 in the afternoon. Trust that in the absence of seeing body language, your team members will give you open and honest feedback if they support what you are saying or disagree with it. Trust that you are incredible and can uniquely contribute something to a culture that no one else can. And trust that when you reach out to a colleague personally, they will reciprocate. Going back to my initial skepticism, it has evaporated over six years because I have seen all of the above in action across each of our team members and leadership team, and it has even strengthened as we have doubled in size as a team in recent years.

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?

Several years ago, we were primarily a text and audio-only company in terms of our communications tools, but today, with tools like Slack and Zoom, video is always an option and helps remove some of the body language visibility barriers. With that said, not every call is video, and not everyone is comfortable being on video. One amazing tool that we use at LaCalle Group is the Birkman questionnaire, which helps increase your emotional intelligence and understanding of your colleagues. Not everyone is motivated the same way, not everyone wants to receive critical feedback the same way, and not everyone reacts to change the same way. We often refer to each other’s Birkman reports and consult with our HR Director, a Certified Birkman Method consultant, to get a better understanding of our coworkers and how to best communicate with them. For critical feedback and other tough conversations, even in the absence of video, we are able to remove some of the discomfort by seeking to understand how the recipient will best receive and process the information in advance and adjust the communication accordingly. It is extremely powerful, effective, and respectful to think of how your colleague needs to receive the information versus simply preceding with how you think best to present it.

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

I tend to avoid providing constructive feedback over email or any text-based medium. Just because you are in a remote work setting does not mean that you cannot communicate directly with your colleagues! We have all experienced the ill-worded — and consequently ill-received — email in our careers, which results in a “but that’s not what I meant!” moment. The best way to avoid ambiguity or misinterpretation is simply to discuss the issue with someone directly. Sometimes an email recap of the discussion is then helpful to summarize and ensure that both parties left the discussion with the same understanding, but starting with an email significantly increases the probability that the feedback and even tone will be misinterpreted.

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?

Because our company has always been a remote work environment, we thankfully did not have a jarring workplace change in 2020 like so many others. But from our experience as a remote company, it is imperative that expectations are clearly set around communications, accessibility, and reliability, and there needs to be a flexibility and acceptance around doing things differently as long as the work gets done. The single biggest critical mistake that can be made is trying to copy-paste a pre-existing office culture, norm, or cadence onto a remote setting.

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?

There are so many company, management, and culture philosophies in play that can be effective or ineffective based on the organization and team. At LaCalle Group, we consistently try to start with the question: “What is best for our team?” From our core values to our benefits to our strategic initiatives, we approach everything with the belief that if we do our very best to build the best team and take care of them, traditional measures around customer satisfaction, innovation, turnover, and financial performance will thrive. A great example is an annual “benefits optimization” exercise that our HR team conducts. At many companies, such a thing would involve seeking to curtail benefits or at least reduce the expense of them. At LaCalle Group, it is the opposite. The exercise involves benchmarking our benefits portfolio against the celebrated and perceived leaders in employee benefits across various industries to see where we can improve. Examples from recent years include recognizing Juneteenth as an annual company holiday, establishing a wellness program with a certified wellness coach, improving our parental leave policy, establishing flexibility for all religious holidays, and increasing the company-paid portion for our medical plans. The results of the exercise have significant positive impacts in strengthening our culture because it puts meaning and action behind the company’s commitment to doing what is best for our team members and recognizes the diversity and individuality of each of them.

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. 🙂

Hunger and food supply shortages for millions of Americans is something that my family and I discuss frequently and seek to help eliminate, and it is an issue that is intensely visible in our new home state of New Mexico. Inspiration can come from anywhere, and my daughter had the interesting idea of making food and water a human right in our country. I understand that this can be extremely polarizing politically, especially in the current climate, but her premise is that if we are indeed a society, and we have a formalized government in place to provide certain services and essentials to its citizenry, how can a basic human need such as ample food and water not be ensured? When you also entertain that in the United States, 30–40% of our food supply is wasted, yet an estimated 15% of our population suffers from hunger, there are multiple viable solutions to the problem.

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

Theodore Roosevelt gave a speech at the Sorbonne in France in 1910 that is usually referred to as the “Man in the Arena” speech. A critical point for me in the speech is the notion that he would rather be among those who try and fail in their life than be among “those cold and timid souls who neither know victory nor defeat.” I still get goosebumps saying it now. This quote resonates with me because fear of failure is a fundamental human emotion for most of us. But for so many decisions that we make, the fear has a tendency to disproportionately influence our actions versus the real impacts of failure. For me, if the element of fear is not at least somewhat present in the decision that I have made, I need to question if I made the right decision. This applies to the notion of vulnerable trust, career choices, and even love!

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