Tag Archive for: judgement

Skills that matter most for future leadersAs part of our mid-year roundup, we’re revisiting the answers women leaders gave when we asked them what skills will matter most for the future of leadership.

Their answers were wide-ranging. Some pointed to adaptability and learning agility, while others emphasized judgment, instinct, communication, empathy, execution and curiosity. Together, they offer a compelling range of perspectives on what tomorrow’s leaders will need most.

Adaptability and Learning Agility

“Adaptability is a leadership superpower. The next generation of financial leaders will not thrive by mastering one static domain,” says Laura Magyar, Partner at Patomak Global Partners. “They will need flexibility, openness to change, and the willingness to evolve alongside the markets.”

For Erika Irish Brown, Head of Talent and Engagement at Citi, that adaptability begins with learning.

“Future leaders will need learning agility above everything else. The pace of change is only accelerating,” she says. “What we do know is that the leaders who thrive will be the ones who stay curious, stay open and embrace change rather than resist it.”

Carey Ryan, Chief of Staff for Citi Technology Business Enablement, has reached a similar conclusion through her own experience.

“You quickly figure you’ll never know it all, because the world is always changing,” she says. “Instead, I found the key is to always be ready by learning how to operate effectively with uncertainty and always be willing to learn.”

Jamila Piracci, Founder of Roos Inovations, puts the emphasis on how we learn, rather than simply what we know.

“The ability to learn new things matters more than simply amassing new facts,” she says. “The real skill is learning how to learn differently.”

Judgment and Instinct

As AI reshapes professional services, Katherine Kirkpatrick Bos, General Counsel at Starkware, believes some skills will remain firmly human.

“AI is a powerful tool,” she says. “But it can’t replace instinct.”

For Kirkpatrick Bos, that instinct is closely tied to judgment and problem-solving.

“Judgment is hard to teach. Problem-solving, instinct, knowing when something doesn’t feel right—that still matters.”

Nancy Stern, Managing Director at Simplex Trading also puts judgment high on the list, alongside the ability to listen and make decisions amid an abundance of information.

“Strong listening skills, sound judgement and the ability to sift through vast information to make principled decisions will be demanded of our leaders,” she says.

And while vision remains important, Stern is clear about what has to follow it.

“Vision without execution doesn’t count.”

Communication and Human Connection

For Joanna Fields, CEO of Aplomb Strategies, the changing nature of work will make another skill increasingly important: being able to articulate your own value.

Looking forward, she believes the leaders who will thrive are those who can harness AI securely, protect data privacy, and clearly articulate their value in an increasingly automated world.

“As roles evolve, the ability to communicate your unique contribution will be paramount,” she says.

That ability to communicate extends beyond self-advocacy for Bos, whose role as General Counsel often requires her to bridge technology, regulation and law.

“You have to listen carefully,” she says. “Then explain things in a way the other side can actually understand.”

For Stern, meanwhile, leadership is ultimately about people.

“As markets evolve, so must leadership,” she says, pointing to the importance of empathy and “the ability to put others first.”

Curiosity and Complexity

Curiosity is another recurring theme.

For Brown, it is at the heart of learning agility: “The willingness to ask questions, seek out new perspectives and lean into what you don’t yet know.”

Pooja Prahlad, Head of Americas Equity Restructuring at Goldman Sachs, similarly sees curiosity as something leaders need to deliberately preserve as they progress.

“As you grow in your career, you end up teaching more than learning. It’s really important to stay curious and create the time for that.”

But Prahlad also offers a counterpoint to the increasing emphasis on speed and efficiency, particularly in the age of AI.

“Resist the pull toward quick, serviceable answers,” she says. “The distance to an answer is so short now, especially with AI. It’s easy to stop there, even when it’s not the best answer…Spend time to earn the answer.”

What Comes Next

There is no single answer to what future leaders will need most.

For Magyar, it is adaptability. For Brown, learning agility. Ryan emphasizes the ability to operate with uncertainty, while Piracci focuses on learning how to learn. Kirkpatrick Bos and Stern point to judgment, instinct and principled decision-making. Fields highlights communication and the ability to articulate value. Prahlad emphasizes curiosity and the willingness to sit with complexity.

And that may be the larger takeaway from the range of perspectives: the leaders who are best prepared for the future will not necessarily be those who know exactly what is coming.

They will be the ones equipped to meet it.

Katherine Kirkpatrick BosKatherine Kirkpatrick Bos, General Counsel of StarkWare, is excited about zero knowledge proof technology (ZKP), a revolutionary tool in cryptography. She explains that ZKP allows people to prove something is true without revealing underlying information.

ZKPs enable verification without disclosure—complete, sound, and private. While often discussed in the context of blockchain scalability and transaction speed, their possible use extends far beyond cryptocurrencies. Healthcare records, voting systems, and government services all rely on forms of verification that routinely overshare personal data. Zero-knowledge technology offers a path to redesign those systems around privacy by default.

“StarkWare is deep, cutting-edge technology,” she says. “These are some of the smartest cryptographers and developers in the world.”

This potential drew Kirkpatrick Bos to StarkWare, a company building cryptographic systems at the frontier of zero-knowledge technology. The work is not only about present-day challenges. StarkWare has also developed quantum-resistant technology—an increasingly urgent priority as advances in quantum computing threaten existing cryptographic standards.

“Quantum computing could break a lot of what we rely on today,” she notes. “Quantum-resistant code makes that significantly harder.”

Choosing the Right Room

Prior to joining StarkWare, Kirkpatrick Bos was in listed derivatives on digital assets. She was the Chief Legal Officer of Cboe Digital, a U.S. regulated exchange and clearinghouse for spot crypto and crypto derivatives markets; and General Counsel of Maple Finance, a capital efficient corporate debt marketplace which facilitates crypto institutional borrowing via liquidity pools funded by Decentralized Financial (DeFi) ecosystems. Kirkpatrick Bos was also a partner in the Special Matters and Government Investigations practice at King & Spalding.

Kirkpatrick Bos is candid about career inflection points. She has experienced the frustration of executing a plan within a business that wasn’t growing as expected—and realizing she wasn’t in the room where the real decisions were being made.

“That’s a difficult place to be,” she says. “Especially if you believe you could be doing more.”

The response, in her view, is rarely comfort. It is movement.

“It’s much easier to stay where you are than to start over,” she notes. “But if you want growth, you have to take that risk.”

She is especially direct about this advice for women, who are often encouraged—explicitly or implicitly—to value stability over advancement.

“I’ve always approached my career strategically. You have to understand what’s next.”

Mentorship, Integrity, and Judgment

Kirkpatrick Bos credits much of her professional grounding to early mentors, including a senior partner she worked with for over a decade at King & Spalding.

“He could be prickly,” she recalls, “but he inspired loyalty through integrity.”

That lesson—never compromise ethical standards—has stayed with her. So has the importance of seeing what is possible. Senior women who pushed boundaries in their careers made abstract ambition tangible.

“If you see it, you can be it,” she emphasizes. “If others are doing it, it’s not impossible.”

The guidance she now imparts is unsentimental and practical: protect your principles, make hard decisions when required, put your family first, and outsource what you can.

Leadership in an Age of AI

As artificial intelligence reshapes professional services, Kirkpatrick Bos remains skeptical of claims that judgment can be automated.

“AI is a powerful tool,” she acknowledges. “But it can’t replace instinct.”

Over her career, she has seen lawyers develop competence through experience—and others who never do.

“Judgment is hard to teach. Problem-solving, instinct, knowing when something doesn’t feel right—that still matters.”

As General Counsel, much of her role is translation: helping regulators understand technology, and helping technologists understand the law.

“You have to listen carefully,” she says. “Then explain things in a way the other side can actually understand.”

Why It Endures

There are always difficult days. Seniority does not eliminate friction; it reframes it.

What sustains Kirkpatrick Bos is the belief that the work itself matters—that she is helping shape the legal and regulatory framework for technologies that will define the next generation.

She imagines a future where people look back in disbelief at how much personal information was once routinely shared to prove a single fact.

Innovative technology, she believes, does more than improve systems. It keeps people engaged, even when the work is hard.

And in that sense, zero knowledge is not just a cryptographic concept—it is a blueprint for more thoughtful leadership.

By Jessica Darmoni