Common Communication Breakdowns: Joshua Candamo Of Ensurem CIO On The Most Common Communication Breakdowns In Corporations And How To Avoid Them
An Interview With Cynthia Corsetti
Deadline-driven organizations commonly suffer from what I call “eleventh-hour communication.” This pattern of last-minute communication is caused by organizational procrastination, and the very nature of how work is managed. A long deadline, psychologically speaking, implies complexity or a lack of urgency — neither of which might be true.
In the dynamic world of business, where rapid decision-making, seamless collaboration, and innovative strategies are critical, effective communication is essential. Yet, we find that even in the most successful corporations, communication breakdowns can become a regular occurrence, leading to misaligned goals, misinterpreted strategies, and missed opportunities. In this series, we are talking to CEOs, COOs, CTOs, and other C-Suite leaders, to discuss what leads to communication breakdowns, and more importantly, how they can be avoided. As part of this series, we had the pleasure of interviewing Joshua Candamo.
Joshua Candamo is a technology executive with a track record of entrepreneurship and corporate leadership that spans over 20 years. He has an extensive understanding of modern technology, including a Ph.D. degree in Computer Science, and many scientific publications in the fields of Artificial Intelligence and Pattern Recognition.
Joshua is the author of Five Doors of Success, a book conceived from his engineering mindset and passion for helping people succeed in their careers. He describes a pragmatic system to achieve success, along with his experiences while using it and immigrating to the United States and navigating corporate America from a minimum wage job to an award-winning technology executive.
He lives in Tampa, Florida, with his wife, Trish. They have twin boys, Joshua and Jacob, and a third furry child named Cleo.
Thank you so much for joining us in this interview series. Before we dive into our discussion about communication, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
I’ve always been fascinated with solving problems. This started early in my life — almost as an obsession — with building blocks and puzzles, but it’s been a major driver in my career to this day.
The more complex the problems that need to be solved, the more I’m drawn to them.
And this is what brought me to a career in organizational leadership. I’m passionate about helping companies set strategic goals for growth, while motivating employees to bring their very best to the organization on an individual level.
Technology has been a common theme in every step in my career — perhaps because I think of technology as the ultimate problem-solving tool for humankind. Tech isn’t a replacement for people in problem-solving; it’s a tool to enhance our ability, efficiency, and effectiveness for doing so.
What do you think makes your company stand out? Can you share a story?
Ensurem is a young company in healthcare insurance, a space dominated by big established players and highly regulated products. Our vision is to provide retirement-aged adults with a simplified insurance shopping experience. Driven by a fresh perspective, with a focus on innovation and out-of-the-box thinking, we’ve seen major growth over the last few years. I joined the company as employee number 38, to help build the next generation of senior-centric insurance technology. Today, we’re one of the fastest-growing privately held companies in the Tampa Bay area, with over 350 employees. We were ranked #1 in 2020 and #5 in 2021 by the Tampa Bay Business Journal, and in 2021 we surpassed $40 million in revenue — all of which led to our sale to the private equity group 777 Partners that same year.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
If I had to credit a single trait for where I’ve gotten professionally, it would be my knack for deconstructing complex systems.
Starting in my youth, I found that I was good at systemizing complicated processes — putting together large puzzles, solving riddles, and using building blocks to create my own custom structures. Throughout my career, I’ve leveraged this same gift by continually building the expertise to solve more and more complex problems.
I’m a technologist at heart, with a Ph.D. in a subset of artificial intelligence called pattern recognition. Out of all the technological problems I’ve worked on solving, I’ve found that the most difficult always have to do with people and organizational constraints.
When I joined Ensurem in 2019, the company was less than three years old. It was started with the goal of simplifying the insurance-buying process for retirement-aged adults. The focus was innovation, specifically, how to modernize the industry and create cutting-edge technology to help seniors find the right insurance coverage at the best rate.
Let’s face it: you probably don’t think about technology first when you think about seniors and insurance together — probably not even when you think about them separately. Our challenge was building a tech organization that could become a disruptor in this space. When I deconstructed that problem, I soon realized that the main bottleneck wasn’t the technical challenges themselves; it was having access to the right people to solve them. That’s why I turned my attention to creating an organizational structure to hire, manage, and retain highly talented individuals.
Self-awareness is another trait that’s been extremely important in my journey, and it’s not as common as you’d expect. So, if you become a master of yourself, you’ll enjoy a massive competitive advantage in your career. Being mindful of my limitations has always served me well, as I don’t shy away from enlisting others to increase or complement my ability to deliver results. And that idea goes hand-in-hand with the final trait I want to mention. I truly believe that my word is my bond. If I say I’m going to do something, I do it. There is no better way to effectively build trust than through commitment and follow-through.
Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.
I sold my first business, K9 Bytes Software, to a small publicly traded company in 2011. At the time, I was facing the harsh reality of a small niche in a world that was rapidly moving towards cloud solutions, and I believed a larger company would be better able to invest in the technology needed to keep the business growing and thriving long into the future.
Within a year of the sale, most of my employees had been laid off. Today, this experience serves as a constant reminder that I must always think about the future, beyond what’s obvious. Not only about myself but about every member of the organizations I’m part of. I can’t prevent the future, but I can help people be ready for it. That sale taught me to proactively have those hard conversations when faced with uncertainty, to help people understand all possible outcomes, not just the best-case scenarios.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic question. Why is communication within an organization so essential? Can you recall a specific situation where effective communication within your organization led to a significant breakthrough or success?
Skilled business leaders know that communication is the single most important component of building professional relationships. Without communication, there’s no collaboration. Without collaboration, it’s hard to build trust, and without trust, there are no team dynamics.
While transitioning from mid-level to upper-level management, I was lucky to drive the reorganization of a company’s division, with the goal of optimizing team structure and fueling productivity. I opted to start with what I still believe is the most cost-effective way to foster communication: rearranging the office seating.
Distance separates people psychologically as well as physically. By bringing desks closer together, you can break down those mental barriers that negatively affect team building, while leveraging the natural positive social dynamics that come from proximity.
Although many other variables are important for fostering communication, including the availability of personal space, nature of the work, noise levels, office layout, even the quality of the furniture, proximity is the simplest — and one of the most powerful — variables you can control.
It didn’t take long for the seating arrangements to lead to a double-digit uptick in productivity across the department, measured by work completed vs. time spent across all ongoing projects.
As modern corporations evolve into hybrid or exclusively remote work environments, we still have a lot to learn in terms of low-cost alternatives to proximity for better collaboration.
Is there such a thing as overcommunication? Have you ever faced any challenges or backlash due to overcommunication, and how did you address it?
Yes, overcommunication can be a real problem if you allow it to be.
Providing unnecessary context or overly detailed information to someone who’s uninterested usually backfires. Especially problematic is oversharing complex information, such as technical details or information specific to a specialized domain to those who don’t need or care for it.
I’ve seen oversharing managers introducing unnecessary overhead, which leads to employee disengagement, as well as the oversharers being labeled as ineffective communicators. In both cases, I’ve found myself managing the problem the same way: with constructive feedback.
Most people don’t realize they’re overcommunicating. We’re constantly reminded of the positive effects of communication, but rarely trained on the backlash that can come from oversharing. My advice is twofold. First, provide feedback as quickly as possible, while the experience is fresh in the person’s mind. Second, help them reflect on the intended goal of their message, as well as the perceived experience of those hearing that message. In other words, was your communication effective? Providing actionable insight — rather than generic feedback — is the key to leading a meaningful change.
How do you strike the balance between over-communication and under-communication within the organization? What guiding principles do you follow?
Not sharing enough and oversharing are both problems you want to avoid. There is a “right amount” of information to share, but it depends on who you’re sharing information with.
You can’t closely manage every individual in your organization — and even if you could, you wouldn’t want to micromanage interactions. However, two effective techniques to ensure information flows efficiently are requiring clear meeting agendas and regularly reviewing overhead statistics.
I constantly challenge my management team to discuss the value of regularly scheduled meetings, and I ask them to try and maximize value while minimizing time spent.
The rise of hybrid work has brought new communication dynamics. How have you found this shift affecting communication within your organization, and what innovative methods have you implemented to adapt?
The COVID-19 pandemic has been the most disruptive change to any business environment in our lifetime. Suddenly, doing business as usual was no longer an option. As we at Ensurem switched completely to remote interactions, two main operational changes helped us adapt while continuing to grow.
First, all meetings with remote employees involved are held using video. We provide everyone with cameras, and we ask them to turn them on for all meetings. The idea is to maintain the psychological connection that comes from face-to-face communication. Video usage is reviewed monthly, with our entire technology organization consistently achieving a camera-on rate of over 90%, compared to all the time spent on calls. Although this was perceived as heavy-handed at first, now it’s the norm for the organization. After all, you can’t hide from people when you’re facing them across a table in a conference room. It’s the same notion, applied to a virtual world.
Another method I’ve had success with is trading outings for e-versions of traditional team-building activities. I’ve experimented with a Hawaiian-themed online video lunch, virtual pet meetup, hobby show and tell, and company-sponsored food delivery to employees’ homes. It’s tough to match the powerful effect of in-person team building activities. However, in remote environments, e-activities are your best bet. The last thing you want is inaction. In hybrid environments, a good compromise is to schedule regular virtual activities while trying to get the company, or departments, together when possible.
In an era of specialized roles and departments, how do you ensure that different parts of the organization are not working in silos, and what mechanisms encourage cross-functional dialogue? Similarly, how do you maintain a sense of unity and shared purpose among teams in a hybrid work environment?
The obvious answer is to build the organizational structure that works best for your business needs, along with the right processes for communication to flow organically.
The less obvious answer is to carefully embed communication as an integral part of organizational culture and offer employees a social platform to develop relationships. This is best accomplished by fostering an environment of teamwork over individual contribution and providing the time and platform for teams to socialize.
These answers apply to both co-located and remote teams, and a closer look shows they’re both about fostering communication at the individual level. To maximize organic peer-to-peer communication, one organizational variable is particularly effective: team composition, and in particular, team size. Why? Smaller teams are naturally better geared to face human biosocial limitations, reducing our natural socializing overhead and allowing members to build stronger relationships.
Ok, super. Here is the main question of our interview. What are your “Five Most Common Communication Breakdowns in Corporations and How to Avoid Them”?
These are the five most common types of communication breakdowns.
Number One: Eleventh-Hour Communication.
Deadline-driven organizations commonly suffer from what I call “eleventh-hour communication.” This pattern of last-minute communication is caused by organizational procrastination, and the very nature of how work is managed. A long deadline, psychologically speaking, implies complexity or a lack of urgency — neither of which might be true.
The solution is to switch from managing deadlines to managing progress regularly. This solution should be driven by your project management philosophy and tools. Focus on building an environment where progress is discussed daily, and you’ll see that people no longer wait as long as they can before they communicate.
Number Two: Information Silos.
Information silos refer to individuals within an organization who keep information to themselves. In my experience, it’s not always malicious or even conscious behavior; however, it still results in a lack of transparency and ineffective workflows, and if not managed properly, it can spread and become a systemic organizational issue. The better alternative to an information silo is a subject matter expert — a valuable resource for the rest of the team.
The most effective weapon against information silos is radical candor. Radical candor is a communication approach based on caring personally while challenging directly. The goal is to clearly articulate that someone who is known to hoard knowledge becomes an organizational problem waiting to be solved, then discover the source of the problem. If the behavior comes from a lack of awareness, then the solution will follow organically over time through continuous coaching. Otherwise, you may have a larger issue that will require additional hiring or extreme disciplinary actions.
Number Three: Positive Bias.
Positive bias refers to our tendency to share positive information and avoid discussing negative issues. It’s a common communication breakdown, and it’s most often caused by ineffective management practices or a lack of processes targeting transparency and continuous improvement.
The simplest solution to positive-biased communication comes from the top. You must foster an environment that embraces the sharing of information at all levels of the company — both positive and negative — by establishing the right processes to do so, while avoiding retaliation. A healthy corporate culture is not an excuse for not dealing with problems. Understanding problems is always an asset, and ignoring them is always a liability. The goal of transparency is not finding scapegoats, but continuous improvement.
Number Four: Rigid Chain of Command.
A rigid chain of command can quickly translate into ineffective communication flows. Organizational structures exist for good reasons, but when used to artificially constrain communication, they’re terrible for productivity.
The solution starts with senior leaders reviewing and crafting a culture of openness while setting good examples organization-wide. In my work with large insurance companies, I’ve seen the extreme effect of red-taping and bottlenecks originating from rigid chains of command. I’ve found it particularly effective to have more conversations with the employees who are closest to the issues at hand — while being careful to avoid sending the message that you’re trying to bypass their superiors. A useful question is, “Is there someone else I can include in my communications with you to help streamline this process?”
Number Five: Closed Organizations.
A closed organization does not provide enough or clear information about its inner workings — from goals, to corporate values, to reasons to take on some projects and not others. This isn’t about sharing sensitive information, but sharing enough so that everyone in the organization is engaged and energized with the direction of the company. Lack of transparency affects employees at all levels.
The solution is to become a more transparent organization that doesn’t shy away from explaining “the why.” This can be easily accomplished with regularly scheduled high-level meetings, as well as management training focused on effective knowledge sharing. Knowing why business decisions are taken can be extremely empowering to employees.
Last Thought:
Over my career, I’ve observed that all levels of management can be overly focused on productivity. Nevertheless, most communication breakdowns are also related to that same management. Instead of chasing productivity goals in a vacuum, start by looking at communication. Better productivity is a natural byproduct of better communication.
What role do you see for yourself as a leader in fostering a climate where employees at all levels feel comfortable voicing their opinions and concerns? Can you share an example where this openness led to a positive change?
More than anything else, I see my role as responsible for creating a platform of openness. The more impactful the observed issues, the more careful you must be that employees have the right places to safely voice their opinions and concerns.
I strive to make openness the default behavior, especially when a problem is observed. To this end, we train our employees on the process of reporting issues, and how we then analyze the root cause to foster incremental improvement as the norm.
Navigating the complex terrain of corporate communication must certainly present unique challenges. As a C-suite leader, what thoughts or concerns, related to this or otherwise, often keep you awake at night? How do these influence your approach to leadership?
If you want to move fast, you can’t be afraid to trip.
That means accepting failure, mitigating losses, and rapidly learning should all be integral parts of your operational culture. As a leader of fast-growing organizations, I’ve always chosen to foster information sharing rather than a utopian environment where failure doesn’t exist. Failure to disclose problems promptly is one of the worst communication challenges a company can face, and I’ve seen it cost companies millions of dollars. In simple terms, I like to drive towards the “see something, say something” mentality, in a systemic way at every level of the organization. When everyone is watching, and you have the right processes in place for information sharing, your company becomes better equipped to handle difficult and complex situations as they arise.
Can you share a piece of feedback or advice you received that significantly altered your leadership approach or philosophy?
A former boss asked me to research the theoretical benefits of “servant leadership” and contrast the findings with our current management approach.
Although the concept of servant leadership has been around since the 1970s, it’s gained tremendous popularity in recent years for its power in promoting teamwork and a sense of purpose among employees.
After hundreds of hours researching the topic, I’ll summarize for you the message I gave my boss, the same one I always share with my management team: Your management style won’t dictate your chances for success. There are no definitive, scientific studies that connect biological realities, management styles, and success.
After all, “To turn right, you can turn left three times.”
Your management style should reflect who you are. It will most likely change over time, and depending on the situation. Instead of worrying about how you’ll be labeled, focus on a balanced leadership approach. In one sentence my management philosophy is: If you set expectations clearly and coach as needed, all you have left to do is to be fair.
You are a person of great influence. If you could start 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 love to help every person in the world write a book.
To offer all the services needed, free of charge, so that everyone can create a high-quality book — from copyediting to publishing — and share something they feel worthwhile. Imagine all the wisdom waiting to be unlocked and the benefits it could bring to our society.
How can our readers further follow your work online?
Please connect with me on LinkedIn. I regularly write about success, leadership, and technology topics. I also invite you to read my book, Five Doors Success, where I delve deeply into some of the communication problems that can be a drag on your own career and personal success.
Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!
About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.
