Daniel Gielchinsky of DGIM Law: 5 Ways Empathy Will Affect Your Leadership
An Interview With Cynthia Corsetti
Empathy leads to a better work-life balance among team members. We routinely encourage people to take time off, spend time with their families and friends and support involvement in community, religious and social organizations.
Empathy, the ability to understand and share the feelings of another, is increasingly recognized as a pivotal leadership trait. In an ever-evolving business landscape, leaders who exhibit genuine empathy are better equipped to connect, inspire, and drive their teams towards success. But how exactly does empathy shape leadership dynamics? How can it be harnessed to foster stronger relationships, improved decision-making, and a more inclusive work environment? As part of this series, we had the pleasure of interviewing Daniel Gielchinsky
Daniel Gielchinsky is a seasoned trial attorney with over 24 years of experience helping clients through commercial litigation matters. His background as a trial attorney in State, Federal, Bankruptcy and Appellate courts in Florida, New York, New Jersey, Delaware, and Texas affords him a unique advantage. Daniel has earned an excellent reputation for handling challenging shareholder and partnership disputes. His tenure on Wall Street and strong financial background allows him to successfully navigate the forensic accounting and valuation issues fundamental to these cases. Daniel is also well versed in real estate, foreclosure, construction, employment litigation and arbitration. In the insolvency arena, Daniel represents debtors, creditors, fiduciaries, committees, and other parties-interest in Chapter 7, 11, 13 bankruptcy cases, including those filed under the Small Business Reorganization Act. He is also well versed in assignments for benefit of creditors, receiverships, and out-of-court workouts. Daniel successfully represents financial institutions, investors, and landlords in cases involving Ponzi schemes, fraudulent investments, distressed hotels, large retail chains, and entertainment venues.
Daniel’s experience includes being a bankruptcy practice group leader and ‘Of Counsel’ at well-known law firms in the Northeast and South Florida, securing favorable outcomes for clients in high-stakes cases. With the leadership experience and accolades attained in his former roles, he owned and managed his own law practice for seven years before joining forces with Isaac Marcushamer to leverage their combined expertise and form DGIM Law. Daniel is acknowledged as a leading attorney by SuperLawyers, in both Florida and New Jersey, and in several prominent legal publications, including The Wall Street Journal, NY Post, Law360, Daily Business Review, Routers and Bloomberg Law. Daniel’s expert analysis has been featured in numerous interviews with national and international news outlets, establishing him as one of the foremost thought leaders in the Bed, Bath, and Beyond bankruptcy case.
An outspoken advocate through his leadership role with Autism Speaks, Daniel uses his courtroom skills and political connections to promote solutions for the needs of individuals with autism and their families. Daniel’s attitude towards community service, embodied by his role as an elected official, a senior leader of his synagogue, and board member of several organizations, is to do “service for the sake of service” and to prioritize giving back to the community. He balances his work life by spending time with his boys, practicing mindfulness, and pursuing his passions for motorcycles and sports cars.
Thank you so much for joining us in this interview series. Before we dive into our discussion about empathy, 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 knew from an early age that I wanted to be a lawyer. My father had introduced me to several of his friends and asked them to talk to me about their careers or take me to work with them. I gravitated towards the lawyers because I thought what they did was most interesting. While I was in law school I worked on Wall Street and had a great deal of exposure to corporate finance, so I thought I would become a deal lawyer. But by the time I graduated law school in 2001, the stock market had crashed, and no one was hiring first year lawyers to be transactional attorneys. But during law school I had been exposed to trial advocacy and I enjoyed that field very much. I accepted a position at a medium sized firm that gave me exposure to real estate litigation, commercial and civil litigation and bankruptcy. With my background in finance, I gravitated towards the complex commercial and bankruptcy cases that involved financial statements and projections, forensic accounting and fraud analysis, and over time I developed specialties in those types of matters.
Can you share the most interesting story that happened to you since you started your career?
In 2010, I was living in Manhattan and working at a regional New Jersey based law firm. My then-wife was also an attorney, and due to the trajectory of her career, she had proposed that we consider leaving the tri-state area and looking for jobs in South Florida. One night I happened to come across a documentary about the Scott Rothstein / Rothstein Rosenfeldt Adler law firm $1.2 billion Ponzi scheme, which was then unfolding in multiple courts across South Florida. Every significant South Florida law firm was involved in the case in some capacity. I found the story very interesting, so I started researched news stories and Court filings about the Ponzi scheme and read everything I could.
Several weeks later, I had an interview with the Bilzin Sumberg law firm, one of the most highly regarded law firms in South Florida. The practice group leader asked me whether I had heard about the Scott Rothstein Ponzi scheme, and of course, I was very knowledgeable and had plenty of information to share. I suppose the practice group leader was impressed with my knowledge, because a week later I had a great job offer and I joined an outstanding law firm. I have remained friends with my former colleagues at that firm to this day.
What do you think makes your company stand out? Can you share a story?
DGIM Law’s emphasis on our mission and core values, including making the law a healthier and happier place, is a big part of what makes our firm stand out. Rarely will you hear a law firm leader place so much emphasis on these values. One of the things that I take great pride in is hearing my team members call our firm “rehab for lawyers and legal professionals.”
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?
Empathy: I think the most critical character trait of a great leader is the ability to really listen and feel what your clients, colleagues, team members and those around you are going through, i.e. to put yourself in their shoes, and to consider their perspectives in your decision making.
Communication: Strong communication skills are very important for any business leader, and especially when we operate in a hybrid environment with many team members working from home. We are keen on making sure to have regular videoconference with and among team members to make sure people are kept in the loop and aware of how our cases are developing and what the expectations of each team member are. We also communicate very regularly with all our clients to make sure that everything we do transmits value. After all, a client does not leave our firm with a new car or a sandwich to show for the experience, but a result to a problem. With that in mind, we make that with each step along the way, our clients are kept informed of all developments and are involved in any significant decision making.
Organization / Attention to Detail: The law is a highly regulated profession, and running a law firm well requires a great deal of organization and attention to detail. We have systems in place to make sure that we comply with all sorts of legal and regulatory requirements as well as court driven and other deadlines. We also have strong financial controls in place to make sure that we can compensate and reward our team members for their efforts.
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.
The hardest decision I am often faced with is whether to take a particular new case. All businesses need a steady flow of revenue to survive, and with the life cycle of a case being 1–2 years, all law firms are constantly under pressure to “feed the machine” and bring in new work. But just because a given case may help pay the bills does not mean that the case is a desirable one. Sometimes clients present with entirely unreasonable expectations, or with ill motives that we can see from the outset as having the potential to create conflict with the client down the road or reputational issues with the judiciary. While it may be hard to turn down a new matter, I must keep the bigger picture and the longer view of things in mind and be sure the firm maintains a stellar reputation.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page. How do you define empathy in a leadership context, and why do you believe it’s a vital trait for leaders to possess in today’s work environment?
Empathy in leadership means choosing to lead with understanding first. It’s the ability to tune into what someone else is experiencing emotionally, mentally, or personally, and using that insight to guide how you support and respond. In today’s work culture, where burnout and uncertainty are common, empathy builds trust and safety. It helps teams feel grounded, valued, and motivated. Empathy is not about being soft. It’s about creating real human connection that moves the mission forward.
Can you share a personal experience where showing empathy as a leader significantly impacted a situation or relationship in your organization?
We had a team member go through some personal struggles and it began to show up in their work and communications with other team members. But I knew in my heart that this was a very highly valued team member who was extremely capable and loyal, and I was willing to bet that the personal struggle could be overcome with time and patience. We adjusted the team member’s role and responsibilities and created a supportive but non-intrusive environment that gave them the flexibility that was needed to deal with the personal issues. With time, the team member’s personal issues improved and resolved, and that individual has returned as a fully productive member of the team, stronger than ever.
How do empathetic leaders strike a balance between understanding their team’s feelings and making tough decisions that might not be universally popular?
Empathetic leaders don’t avoid tough calls. They simply handle them with care. That means being clear, honest, and direct while also acknowledging how the decision might affect others. You can hold space for emotion and still hold the line. When people understand the intention and feel respected, even unpopular decisions are easier to accept. It’s about trust through transparency.
How would you differentiate between empathy and sympathy in leadership? Why is it important for leaders to distinguish between the two?
Sympathy often feels like standing at a distance and saying, “I feel bad for you.” Empathy says, “I’m here with you, and I understand.” That difference matters. Sympathy can unintentionally create separation. Empathy builds closeness and accountability. Leaders need to be present and engaged, not just aware. That presence helps create teams that feel supported instead of pitied.
What are some practical strategies or exercises that leaders can employ to cultivate and enhance their empathetic skills?
Start by listening without interrupting or jumping to solve. Schedule regular check-ins that focus on the person, not just their role. Ask open-ended questions and make time to truly hear the answers. Reflect what you’ve heard to confirm understanding. Lead by example through vulnerability and honesty. People don’t need perfection. They need presence and care. They need to know you are actually listening.
How can empathy help leaders navigate the complexities of leading diverse teams and ensure inclusivity?
Empathy makes room for different lived experiences. It reminds leaders that not everyone starts from the same place or carries the same challenges. Empathy encourages curiosity instead of assumption. When leaders are willing to ask, listen, and adapt, it creates an environment where people feel safe being who they are. That safety leads to better collaboration, deeper innovation, and true inclusion.
Ok super. Here is the main question of our interview. Based on your experience and research, can you please share “5 Ways Empathy Will Affect Your Leadership”? If you can, please share a story or an example for each.
1. Empathy leads to higher employee engagement. I consistently see this across the board with our team members.
2. Empathy leads to greater innovation among team members who feel empowered to bring forward fresh, new ideas.
3. Empathy leads to a higher retention rate among team members, because they feel and know they are valued.
4. Empathy leads to a better work-life balance among team members. We routinely encourage people to take time off, spend time with their families and friends and support involvement in community, religious and social organizations.
5. Empathy leads to a greater feeling of inclusivity within the workplace. We routinely see and hear this from all team members.
Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?
Yes, empathy without boundaries can lead to burnout. Leaders who care deeply sometimes take on too much. The solution is to combine empathy with structure. Care for your team but also care for yourself. Stay grounded in your role, set healthy expectations, and delegate when needed. Empathy works best when it’s shared across the team, not carried alone.
Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?
I don’t think I have any concerns that are “keeping me up at night,” but I do spend a lot of time thinking about growth. What are the practice areas that we need to develop, who are the team members we want to add, and what can we do to attract those types of candidates.
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 have started that movement already, and it is one of our core values: to promote health and happiness in the law. This is a concept that seems foreign to many law firms and lawyers, but it is important to us and it’s an ideology that I want to promote, grow and someday become the norm in our profession.
How can our readers further follow you online?
https://www.linkedin.com/in/dgielchinsky/
https://www.linkedin.com/company/dgim-law-pllc/
https://www.instagram.com/dgimlaw/?hl=en
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.
