Understand the problem thoroughly: Before making any decision, take the time to fully assess the situation. During the pandemic, for instance, we faced numerous challenges around remote work and data security. By thoroughly analyzing client needs, we were able to design solutions that addressed real pain points effectively.
As a leader, some things are just unavoidable. Being faced with hard choices is one of them. Leadership often entails making difficult decisions or hard choices between two apparently good paths. What’s the best way to go about this? Is there a “toolkit” or a skill set to help leaders sort out their feelings and make the best possible decisions? As part of our series about “How Leaders Make Difficult Decisions,” we had the pleasure of interviewing Haroldo Jacobovicz.
Haroldo Jacobovicz is a Brazilian civil engineer and entrepreneur with over 35 years of experience building businesses in technology and innovation. He founded his first company while still in university and has since focused on creating solutions that address practical challenges. In 2021, he founded Arlequim Technologies, a company specializing in computer virtualization. He’s also the chairman of e-Governe Group, a pool of Brazilian companies acting in software development for Governments. Alongside his work in business, Jacobovicz supports social causes in health, education, culture, and animal welfare, reflecting his commitment to giving back to the community.
Thank you so much for your time! I know that you are a very busy person. 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?
Of course, I’d be happy to share. My journey began in civil engineering, a field I initially chose because both my parents were civil engineers. My father, Alfredo, was also a professor, and my mother, Sarita, was one of the first female civil engineers in Paraná, Brazil — a true pioneer. I grew up inspired by their ability to build things that lasted, but as I studied, I realized my passion leaned toward technology and IT. I saw technology as another way to create lasting impact but in a more dynamic, evolving way.
During my college years, I founded my first company. It didn’t last much, and I had to close it after two years, but that failure taught me valuable lessons about timing and perseverance. I later worked for ExxonMobil and a state-owned company, Itaipu, which gave me a deeper understanding of market dynamics and client needs. These experiences built a solid foundation for me to venture back into entrepreneurship with renewed confidence and focus. Looking back, it was these early trials, and the willingness to learn from them, that shaped the entrepreneur I am today.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story?
Absolutely. My parents played a significant role in shaping my path. My mother, Sarita, inspired me with her determination and trailblazing spirit. She taught me to be bold and think ahead. My father, Alfredo, instilled a love for problem-solving and creativity. They encouraged me to pursue civil engineering and also taught me the value of ethics and community, which remain central to how I lead.
I also owe a great deal of gratitude to the ideas of Morris West, an author I discovered in college. His perspectives about subscription-based service models sparked a lifelong interest in creating long-term, mutually beneficial relationships with clients. Those ideas laid the groundwork for many of my business strategies, including my decision to focus on recurring revenue models in IT.
Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?
One of the most trying periods for me — as for many, many others — was during the COVID-19 pandemic. Almost overnight, the world shifted to remote work and online education. For tech and telecommunications businesses like I led at that time, it presented an urgent need to address gaps in mobility, performance, and data security. My approach during this time was to focus on identifying real solutions, rather than simply reacting to the crisis.
I divided my team into two groups: one focused on maintaining the quality of current services, and the other worked on developing forward-thinking responses to emerging issues. I made a point of maintaining open communication with both factors, ensuring alignment in our short- and long-term goals. We quickly adapted by offering solutions that addressed the immediate needs of our clients while preparing for the longer-term transformation of work and education. It was a time of uncertainty — but also an opportunity to rethink and strengthen trust with our clients.
It was then that we designed the first business model for the virtual computer addressed to companies, governments e final customers. The idea of having a solution for mobility with security, high-performance, easy access and technical support turned into a new company: Arlequim Technologies, founded by the end of 2021.
Did you ever consider giving up? Where did you get the motivation to continue through challenges? What sustains your drive?
I’d be lying if I said I never had moments of doubt. In my early career, when I had to close my first company, I questioned whether I had what it took to succeed as an entrepreneur. But I never saw failure as a stopping point. Instead, I viewed it as a lesson — a sign that I needed to improve, adapt, and try again.
What motivates me is the potential to create meaningful change, whether for a business, a public agency, or even an individual. I’m driven by the idea of turning obstacles into opportunities. When I see how technology can transform lives, it reinforces my belief that every setback is just part of the journey toward something greater.
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?
Selling Horizons Telecom was one of the toughest decisions I’ve had to make. I founded that company with a vision of building something lasting, and my philosophy has always been to grow ventures over time. However, I reached a point where I realized that stepping away from Horizons Telecom would allow me to focus my energy on developing new projects, particularly in virtualized computing technologies.
It wasn’t an easy choice — I felt deeply connected to the business. But in hindsight, it was the right decision for both me and the company. It freed me to pursue new ideas while ensuring Horizons to become part of bigger Brazilian telecommunications group.
What process or toolset can a leader use to make a choice between two difficult paths?
For me, the process begins with data. I track over 100 key performance indicators to understand the current state of my businesses and where improvements are needed. That data, combined with regular discussions with my teams, helps me weigh the risks and benefits of each option. I also believe in consulting trusted mentors and advisers when faced with particularly challenging decisions — they often bring perspectives I might not have considered. Ultimately, I rely on a mix of analysis, intuition, and alignment with my long-term vision to guide me.
Do you have a mentor or someone you can turn to for support and advice? How does this help? When can a mentor be helpful? When is this not helpful?
I’ve always drawn inspiration from my parents and authors like Morris West, but I also believe in the power of collective wisdom. A mentor can provide clarity when you’re too close to a problem to see it objectively. They can test your assumptions, help you consider alternative solutions, and share ideas from their own experiences.
However, mentorship isn’t a substitute for ownership of your decisions. A mentor can guide you, but as a leader, the final call — and responsibility — rests with you. It’s essential to take advice as input, not instruction.
What would you say is the most critical role of a leader when faced with a difficult decision?
A leader’s primary role is to stay grounded and ensure alignment between their decision and the organization’s long-term vision. This means communicating clearly with your team, setting realistic expectations, and being transparent about the reasoning behind your choices. It’s also vital to remain calm and composed. Your team looks to you for confidence, especially in difficult times.
Do you ever look back at your decisions and wish you had done things differently? How can a leader remain positive and motivated despite past mistakes?
Of course, hindsight there are always decisions I look back on with the benefit of new knowledge. For example, my first business didn’t last much partly because I underestimated the market’s readiness for the solution I was offering. But I don’t dwell on regret. I focus on what I can learn from the experience and how I can apply those lessons to future predicaments. Staying positive is about keeping your eyes on the bigger picture and remembering that every mistake is part of the learning process.
What is the best way to boost morale when the future seems uncertain? What can a leader do to inspire, motivate and engage their team during uncertaiun times?
Communication is key. In times of uncertainty, people look for reassurance and direction. As a leader, it’s crucial to maintain regular communication with your team, be transparent about challenges, and celebrate small wins along the way. I’m a firm advocate for encouraging collaboration. When team members see their efforts making an impact, they remain motivated and engaged, even in adversity.
Can you share 3 or 4 of the most common mistakes you have seen other businesses or leaders make when faced with a hard decision? What should one keep in mind to avoid that?
One mistake I’ve seen is clinging too tightly to an initial idea, even when the market signals that it is not ready. My first business didn’t last long because I didn’t account for the timing and readiness of the market, even though the business model itself was sound. Leaders need to listen to the market, remain flexible, and pivot when necessary.
Another common error is poor communication during tough times. When teams don’t understand why a decision is being made, it can lead to confusion, mistrust, and decreased morale. Transparency, even when the news isn’t ideal, builds trust and keeps everyone aligned.
Additionally, excess analysis can devastate a business. I’ve seen leaders hesitate too long because they want perfect data before deciding. While I believe in making data-driven decisions, there’s often a point where you have to trust your instincts and take action.
Finally, ignoring the team’s input is a fool’s game. Leaders who make decisions in isolation often miss valuable thoughts from their team. Engaging your team not only improves decision-making but also strengthens their buy-in and commitment to the chosen path.
Based on your experience and success, what are the five most important things a leader should do when making difficult decisions?
- Understand the problem thoroughly: Before making any decision, take the time to fully assess the situation. During the pandemic, for instance, we faced numerous challenges around remote work and data security. By thoroughly analyzing client needs, we were able to design solutions that addressed real pain points effectively.
- Rely on data but trust your instincts: I monitor over 100 key performance indicators to track business health. Data is critical, but there are times when instinct plays a role too, like when I decided to sell Horizons Telecom. The data supported the decision, but it was also a gut feeling about where my energy would be better spent.
- Involve the right people: Great leaders don’t operate in silos. When making difficult decisions, I rely on my team for their expertise and perspectives. For example, when we transitioned to subscription-based service models, it was a collective effort that allowed us to implement the idea successfully.
- Communicate transparently: When I sold Horizons Telecom, I made sure to explain my decision to my team and stakeholders. By being upfront about the reasons, I was able to maintain trust and ensure a smooth transition.
- Think for the long term: Decisions can be tough because short-term gains often conflict with long-term goals. I always try to align my decisions with the bigger picture — whether that’s building a lasting legacy or leaving a better world through technological advancements.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
One quote that resonates deeply with me is: “Every adversity is a step closer to achieving your goals.” I’ve seen this play out countless times in my career. My first business didn’t last, but the lessons I learned from that experience helped me build stronger, more resilient ventures later. It’s all about how you approach challenges. If you see them as opportunities to learn and grow, they can propel you forward.
How can our readers further follow your work?
Readers can follow my work through my companies’ official websites and social media channels. I’m also active on platforms like LinkedIn, where I share insights about entrepreneurship, technology, and leadership. Staying connected to the business community is important to me, and I enjoy engaging with others who share a passion for ingenuity and growth.
Thank you so much for sharing these important insights. We wish you continued success and good health!
Haroldo Jacobovicz Of Arlequim Technologies On How Leaders Make Difficult Decisions was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.