With clients spanning the United States and Israel, Ari Segal provides consulting services focused on nonprofit organizational strategy. Among his areas of emphasis are business planning, gap analysis, finance, and organizational diagnosis. He also delivers strategic pathways toward attaining sustained growth and optimizing performance. Ari Segal has created a strategic plan for the Ministry of the Diaspora of the State of Israel to institute the Global Beit Midrash program. This provides a springboard for civil dialogue and engages Jewish thought leaders around the world.
For the past seven years, Mr. Segal has provided Yeshiva of Flatbush with volunteer and professional guidance in areas such as transition strategy. He consulted with the head of school on change management pathways and delivered a comprehensive reorganization plan for the Lower School. He also helped reposition financial planning capacities and developed a budget forecasting tool and financial model.
Mr. Segal’s experience extends to a role as investor and co-operations manager with the Pentable Capital Opportunities Fund, a micro-fund targeting the real estate market. Ari Segal is the longstanding CEO and chief strategy officer of the Shalhevet School in Los Angeles, and was successful in turning around a struggling operation.
What is your typical day, and how do you make it productive?
My days always start early with morning prayers before I jump into my workload. Reflection inspires me to consider and zoom in on what’s most important and inspires me to contemplate where and why to apply my effort. I structure my schedule with strategic prioritization so that once I’m at my desk, I am confident my day is mapped out in the most effective and efficient manner; I don’t need to pause to question if my “busyness” is productive. I use time blocking to ensure my time is spent wisely, efficiently, and intentionally. Key tasks and meetings always stem from and align with broader goals with direct connections to core missions. I also input time in my calendar to periodically reflect and recalibrate as needed, remaining flexible as needed while maintaining clear focus on purpose and productivity. At day’s end, I consider how the day went and what changes I’d make moving forward and adjust accordingly. There is always what to learn from and improve upon.
How do you bring ideas to life?
Intentional delegation and collaboration are the bread and butter to bringing ideas to life. I strive to empower my team by clearly communicating goals and expectations and ensuring everyone is set up to successfully execute in their endeavors. A couple of central themes in my leadership model are collaborative refinement, collective ownership, and innovative problem-solving; when these strategies are implemented among the team, ideas transform into tangible outcomes.
What’s one trend that excites you?
I am particularly excited about the increasing integration of proven business principles and strategic thinking into nonprofit management. It signifies greater sustainability and effectiveness, enhancing our greater ability to nurture future leaders.
What is one habit that helps you be productive?
Intentional calendaring is, by far, one of the most impactful habits I’ve cultivated that yields higher productivity and achievement. Deliberately allocating a specific time for every professional and personal priority also reduces stress, as when navigating multiple highly demanding roles, the influx and sense of urgency of mounting matters can lead to overpowering overwhelm and paralysis. In order to manage all of my responsibilities and tasks, I refer to my calendar to keep me on track and to make sure I’m addressing and tackling all that needs to be attended to.
What advice would you give your younger self?
Looking back, I can see moments when I was so focused on maintaining a certain image or defending a position that I missed opportunities for growth and connection. The most profound leadership often emerges when we acknowledge our limitations and approach challenges with humility. Instead of thinking I needed to project a particular presentation of myself in order to control how and what others thought of me, I’d tell my younger self not to stress or worry about what others think about me and to concern myself more with what I, myself, think about myself. Impress myself, make myself proud, strive to improve myself by my own measures that I deem important and valuable. Integrity and self-pride are constructed on the inside.
I’d also tell my younger self to appreciate the journey rather than fixate on destinations. Early in my career, I was constantly looking toward the next achievement, the next position, the next milestone. While we are geared for growth, I now better understand that meaningful impact happens in my day-to-day interactions with others, that small decisions made daily add up, and that the consistent application of values are what contribute to our overall sense of satisfaction in ourselves—not just the headline moments.
Finally, I’d emphasize the importance of building genuine relationships starting from a younger age. The quality of your connections with others—based on trust, mutual respect, and shared purpose—ultimately determines your ability to effect change on a grand scale and across a wide plain. While technical expertise matters, emotional intelligence and relationship skills are truer multipliers of leadership effectiveness. My younger self would have benefited from this realization and would’ve enabled me to, by this point in time, have built an even grander and wider network of amazing people that I could have had the privilege of knowing today.
Tell us something you believe almost nobody agrees with you on?
Despite not necessarily being a fan of President Trump or some of his policies, I believe it is a travesty that he has not been given the Nobel Peace Prize for bringing about the Abraham Accords (and maybe a truce in Russia-Ukrainian war). Whatever you feel about him – even if you hate the man – the Peace Prize is intended to reward people who have brought about peace.
What is the one thing you repeatedly do and recommend everyone else do?
Prioritize diversity of thought and openness in communication within your institution. Creating an environment that values varied perspectives not only strengthens commitment to Jewish values where many of our esteemed Rabbinic leaders debated and disagreed with one another but also fosters deeper learning, expansion of thought, and social/emotional skills in ourselves, especially empathy. To exercise this value and cultivate such skills, I deliberately engage with perspectives that challenge my own thinking. In today’s world, it’s remarkably easy to consume only information that reinforces existing beliefs.
To make sure I don’t put myself into an echo chamber, I make a conscious, deliberate practice of regularly reading thoughtful arguments from people I disagree with—not to refute them but to understand them. This doesn’t mean abandoning principles or descending into relativism. Rather, it means approaching complex issues with appropriate humility, recognizing that truth is rarely contained entirely within a single perspective or narrative.
I recommend everyone deliberately adopt this practice because it transforms how we view and engage with others. In the process of sincerely trying to understand opposing viewpoints, people develop more compassion toward those who disagree, grow in their ability to find nuanced solutions to complex problems, and actually become more persuasive in their own positions. In a world increasingly defined by polarization, this willingness to engage across differences becomes not just personally enriching but socially essential.
When you feel overwhelmed or unfocused, what do you do?
I return to fundamentals. My foundation. Feeling overwhelmed is natural and expected, so when it starts to creep up, before it consumes me, I take a big breath, proverbially step back, and reconnect with my core purpose—why I do what I do, the reason I entered education, what values drive my work, and what ultimate goals I’m pursuing. This deep inhale coupled with a perspective shift often reveals that many “urgent” matters aren’t aligned with what’s truly important, and I make an intentional choice not to worry about them.
Practically, I’ve developed a ritual that helps reset my mental state. I get up from where I’m sitting and take a short walk, even if to refill my coffee; the forward motion triggers my brain to believe that I am making progress and advancing in some capacity, which breaks whatever stagnation, doom, or feeling of insecurity that may be taking place. A brief moment of disconnecting from technology also does wonders for resetting my central nervous system and reorienting my focus. It creates fresh mental space to reorganize my thoughts and allows me to return to my top priorities effectively. I also believe in the power of honest conversation. When I’m feeling especially overwhelmed, after doing the aforementioned, I’ll often reach out to a trusted colleague or mentor who can provide perspective. Sometimes, just articulating the sources of pressure helps reduce their power and weigh; and external viewpoints often reveal solutions I couldn’t see on my own.
Perhaps most importantly, though, is that I’ve learned to recognize overwhelm as an indication that something in my approach needs adjustment—whether it’s my expectations, my boundaries, my time management, my strategies, my coping mechanisms, my caffeine consumption. Rather than simply pushing through, I try to learn from these moments and make systemic changes that prevent similar situations in the future.
What is one strategy that has helped you grow your business or advance in your career?
Intentionality in every aspect of leadership has arguably been a profound factor in growing any organization I’ve been a part of. Approaching leadership and team building with deliberate intentionality, from calendar management to communication style to organizational vision, this strategy proves efficacious time and time again. And not only in ensuring the organization is thriving but also by transforming how I build relationships. Rather than casual or opportunistic networking, I willfully cultivate connections with people who share core values but bring diverse perspectives. These relationships have repeatedly opened doors to new opportunities, partnerships, and insights that have advanced both our organization and my career.
The beauty of intentionality as a growth strategy is its applicability across contexts. Whether leading a small team or an entire organization, consciously aligning actions with values and clear, concrete objectives creates momentum that propels both personal and institutional advancement. When I operate in this manner, it also inspires my team to do the same, leading by example and expectation. Together, we are a significantly more powerful dynamic and group; and growth is inevitable.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Early in my career, I made a mistake of thinking I had to be the “perfect leader,” or at least present a perfect image, and display ultimate confidence in my own unilateral decision making in order to gain the trust, respect, and the sense of authority that leaders possess. I didn’t quite understand yet that the opposite is actually true and required in order to achieve such an end goal. I geared more to a top-down authoritarian leadership style, which wasn’t my natural inclination but what I believed at the time was the best way to navigate my role.
In doing so, I made a significant misstep when addressing a controversial policy change. Convinced of the correctness of my position, I implemented the change with minimal consultation and then defended it against criticism rather than truly listening to concerns. The result was predictable in retrospect: resistance hardened, trust eroded, and what could have been a collaborative evolution became a divisive conflict. I had achieved a technical victory but a cultural loss—the exact opposite of effective educational leadership.
I overcame this failure by first acknowledging it publicly. I gathered the community, admitted my misstep, and then reopened the conversation with genuine curiosity rather than defensiveness. We ultimately reached a modified approach that incorporated multiple perspectives and, most importantly, restored trust in not only me as a leader but in a collaborative process.
This experience taught me several enduring lessons. First, how one implements change is often more important than the change itself. Second, resistance usually contains valuable information that can improve upon an original idea if one is humble enough to listen. Finally, I learned that leadership authority comes not from positional power but from the community’s trust—and garnering that trust requires transparency, vulnerability, and genuine respect for diverse perspectives. I now view that failure as one of my most valuable professional experiences and lessons. It fundamentally shifted my leadership approach from asserting authority to building consensus—not by watering down principles but by engaging sincerely with different viewpoints to create solutions with broader ownership and wisdom.
What is one piece of software that helps you be productive? How do you use it?
Calendar-blocking software has transformed my productivity. I personally use Google Calendar and Boomerang with the appointment scheduling feature, as it streamlines multiple systems I use via Google, but the specific platform matters less than the methodology of intentional time allocation. Before embracing this approach, I operated like many leaders I had learned from—responding to the loudest demands and addressing the most immediate crises, putting out fires as they popped up, with little proactive control over my schedule and tasks. I quickly realized that approach was unsustainable and would lead to burnout, so I learned how to properly block time for every significant responsibility in a more thoughtful, proactive manner.
This system serves several crucial functions. Firstly, it forces me to be realistic about time constraints—if I can’t fit something into my calendar, I must either delegate it or acknowledge it won’t happen. Secondly, it creates boundaries that protect important but nonurgent work from being displaced by daily emergencies. Thirdly, it provides psychological security by assuring me that every priority has its dedicated time. This way, I don’t have to carry the mental load of all my responsibilities at the same time. I can attend to on one thing at a time and better focus on whatever it is I am addressing.
I’ve extended this system beyond professional tasks to include personal priorities like family time, exercise, and personal development and learning. This holistic approach prevents the common leadership trap of sacrificing personal well-being for professional demands—a trade that ultimately undermines effectiveness in both spheres. The true power of calendar blocking isn’t just organization—it’s alignment. When your calendar visibly reflects your stated priorities, you gain both productivity and integrity.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
Start with Why by Simon Sinek fundamentally transformed my approach to leadership and organizational culture. While its core concept might seem simple—begin with purpose rather than process—the implications of this perspective shift are profound and far-reaching. The book’s central insight resonated deeply with my experience in educational leadership: institutions flounder when they focus primarily on what they do rather than why they exist.
Becoming crystal clear on the “why” before the “how” ensures an organization is appropriately focusing on creating the kind of establishment it’s ultimately aiming to. Understanding and communicating our core purpose profoundly affects how we lead, educate, and inspire those around us; gaining clarity on underpinning reasons behind behaviors and missions is a powerful benchmark from which to operate and build upon. Whether it be communicating with stakeholders, motivating colleagues, or designing curriculum or other business models, starting with “why” provides clarity that directs and elevates every interaction and decision. It’s not just a leadership philosophy but a functional communication framework.
On the podcast front, I regularly listen to How I Built This with Guy Raz. Each episode traces the journey of an entrepreneur or innovator, highlighting both triumphs and setbacks along the way. These narratives offer valuable perspective for anyone leading organizational change, demonstrating that even the most successful ventures encounter significant obstacles and pivotal moments of reinvention.
What both resources share is their emphasis on purpose-driven persistence—maintaining clarity about core values while adapting strategies to changing circumstances. This balance between principled vision and practical flexibility is essential for effective leadership in any field or business venture.
What’s a movie or series you recently enjoyed and why?
The Office remains one of my favorite shows. As much as it’s a farcical workplace comedy, I find its exaggerated portrayal of organizational dysfunction surprisingly instructive for my work as an educational leader.
Michael Scott, with his desperate need to be liked rather than respected, inadvertently illustrates how leadership motivated by personal insecurity rather than organizational mission creates unnecessary complications. Watching his well-intentioned but misguided attempts at management gives me an entertaining mirror to examine my own leadership tendencies.
What makes the show particularly valuable is how it uses humor to reveal truth. When I laugh at Dwight’s rigid adherence to rules without context, or Jim’s clever but sometimes disengaged approach to his work, I’m often recognizing behaviors I’ve encountered—or occasionally exhibited—in real professional settings. The comedy creates enough distance to reflect honestly on these dynamics without defensiveness.
I’ve even used clips from the show in leadership trainings to spark discussions about communication, organizational culture, and management styles. The farce helps demonstrate what happens when egos, insecurities, and misaligned incentives drive workplace behavior instead of shared purpose and mutual respect.
Most importantly, The Office reminds me not to take myself too seriously—a message I often share with graduating seniors. Some of my most valuable leadership lessons have come from moments when I could step back, recognize the absurdity of a situation, and find both humor and insight in my own missteps.
Key learnings
- Nonprofit institutions must embrace intentional leadership—moving beyond reactive management to align daily decisions with core values and long-term vision.
- Collaboration over competition creates stronger communities; businesses that share resources can simultaneously reduce costs and improves quality.
- Intellectual humility—the capacity to engage seriously with opposing viewpoints—has become essential in our polarized world and must be deliberately and effectively modeled and taught to students.
- The most effective leadership balances principled conviction with genuine openness to feedback and input from others, creating cultures where people feel guided, heard, and relevant.
- Sustainable success requires developing the next generation of leaders rather than centralizing authority; organizations thrive when leaders focus on building capacity in others rather than maximizing personal influence.