“Future leaders will need learning agility above everything else,” says Erika Irish Brown. “The pace of change is only accelerating. Today it’s AI, but we don’t yet know what we’ll be navigating tomorrow. 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.”
As part of The Glass Hammer’s Where Are They Now series, we are catching up with leaders we have spoken with before to see how their careers and perspectives have evolved over time. Erika Irish Brown, now Head of Talent Management and Engagement at Citi, has long been focused on creating opportunity and building inclusive workplaces. In this next chapter of her career, she shares how that mission is expanding as organizations rethink leadership, mobility and learning in an era defined by rapid technological change.
Q: What are you currently working on?
As Head of Talent Management and Engagement at Citi, my focus is on our global, talent centric approach to supporting our workforce—one that invests in people, creates opportunities for growth and fosters a culture where everyone can thrive.
Our team leads all of Citi’s efforts around development planning, talent designations, talent processes and succession planning. We also oversee enterprise coaching, our engagement activities including 12 global Inclusion Networks and Talent Management and Engagement Councils across each business and function.
Q: What is inspiring you to lead in the future?
What inspires me about leading into the future is the real momentum we’re building at Citi. We have a clear strategy, a leadership team driving meaningful change and a firm accelerating on every front, including technology.
AI is opening new doors for our people, helping colleagues find opportunities that match their skills and aspirations. As it becomes more integrated into how we work, it will continue to fuel growth, innovation and faster execution.
You can see this momentum in our focus on mobility. In 2025, we filled more than 55,000 roles with 44% coming from internal moves and promoted over 28,500 colleagues into new roles. And with initiatives like Development 365, more than 165,000 colleagues created personal development plans last year.
The combination of our strategy, our people and the possibilities technology unlocks makes the future incredibly energizing.
Q: What makes Citi special?
What makes Citi special is the combination of our globality and our focus on human-centered leadership. As the world’s most global bank, we have people on the ground in more than 90 countries, which gives us a unique level of cultural fluency. It allows us to connect with colleagues where they are, listen to their experiences and ensure our strategy reflects the realities of each market. Our clients tell us this reach is a true differentiator.
Our scale also means we tackle complex challenges across borders and offer a wide range of roles and career paths within one firm. That combination of global breadth and opportunity is hard to find anywhere else.
What also sets Citi apart is our leadership. Jane Fraser, our Chair and CEO, leads with a clear vision, and her leadership shapes a culture of understanding from the top. She is a trailblazer in financial services and the first woman to lead a major financial institution. Our global footprint – who we are, where we are, and the businesses we run—makes Citi a truly special place to grow and make an impact.
Q: What lessons in leadership have you learned working at the world’s most global bank?
I’ve had the privilege of working at several of the world’s leading financial institutions, and those experiences have deepened my understanding of culture and lived experience and reinforced that ambition and leadership show up differently around the globe. Leadership is packaged in all different ways, and that has underscored the need for our leadership frameworks to evolve.
We have to break the myth that there is only one archetype of a leader, especially when it comes to succession planning. Not everyone will say, “I want to be CEO.” Many people are quiet leaders, and that doesn’t make them any less ready for what’s next.
Leadership doesn’t begin with a title — anyone can lead, and leadership can be shown at every level. At Citi, we measure leadership against three principles: we take ownership, we deliver with pride and we succeed together. Whether you lead a large team or contribute as an individual, how you bring these principles to life is what truly matters.
Q: How have you navigated challenging moments, setbacks or self doubt?
Navigating difficult moments starts with remembering that meaningful and sustainable change doesn’t happen overnight. Impact builds over time. I try to focus on what I can control and release what I can’t. At the end of each day, its important that I am able to look in the mirror and know I used my voice—especially when it was uncomfortable or challenged the status quo. I believe silence is a form of endorsement; if I’m not willing to speak up, then who will?
Setbacks are part of the process, but I stay grounded in my competence and confidence. If you’re competent, you have every reason to be confident. Mistakes are okay as long as you take feedback, course-correct quickly and keep moving. Learning agility and making progress matters far more than perfection.
When things don’t work out, I remind myself that there may be something else in God’s plan. Faith helps keep everything in perspective. And if I can honestly say I fought the good fight and did my best on behalf of others, I can move forward with confidence.
Q: What skills do you think will matter most for future leaders?
Future leaders will need learning agility above everything else. The pace of change is only accelerating. Today it’s AI, but we don’t yet know what we’ll be navigating tomorrow. 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.
Being a lifelong learner is no longer optional—it’s a leadership requirement. The leaders who succeed will absorb new information quickly, adapt their approach and translate what they learn into action.
At the heart of learning agility is staying curious —the willingness to ask questions, seek out new perspectives and lean into what you don’t yet know. Curiosity keeps you growing, keeps you adaptable and keeps you ready for what comes next.
Q: Who inspired or influenced you most on your journey, and what did you learn from them?
My parents are my biggest inspirations. They set high expectations, especially around academics and STEM. My mother was a junior high math teacher, and my father rose through the New York City Housing Authority to become Head of Computer Services. In our house, if your grades weren’t where they needed to be, the question wasn’t “Did you try your best?” It was “What happened?”
They taught me to be a change agent. If something wasn’t the way you wanted it to be, you had the power and the responsibility to fix it. That mindset shaped me. You have agency. You can challenge the status quo. You can create opportunities that don’t yet exist.
They also taught me the value of effort and the associated outcomes. What you put into something is what you get out—karma. Education, hard work and smart risks can change your life’s trajectory. Those lessons—accountability, agency and effort—have guided my career and influence how I lead today.
Q: What invaluable, specific guidance have you received along the way?
A few pieces have stayed with me:
- Listen first. Let the culture shape your understanding. Listen to understand, not to reply.
- Invest in people. Exposure, opportunity and access change outcomes. Meet people where they are, lift as you climb and bring others on the journey with you.
- Lead authentically. People, including yourself, thrive when they build trust and feel psychologically safe.
- Challenge the status quo. Commitment and persistence pay off. Be brave and use your voice. Innovate.
Q: What do you impart upon those you mentor — or would impart upon your younger self?
Be ambitious, take stretch assignments and stay curious. Don’t assume your work will speak for itself — advocate for your own growth. And always consider the legacy you’re building. Making a difference doesn’t have to be grand; it can start with creating an opportunity for even one person to succeed.
Q: Has coaching supported you in your journey, and if so, how?
I have absolutely benefited from coaching. At Citi, executive coaching is a capability we invest in as part of our Talent strategy because we know it elevates performance; it’s not about fixing a problem. Just as elite athletes rely on coaches to refine their craft, high performing leaders gain so much from trusted advisors who help deepen self awareness, strengthen impact and navigate complexity with greater effectiveness. When we prioritize continuous development, we position our leaders and our organization to succeed in an environment that is constantly evolving.
Q: Looking ahead five to ten years, what kind of future are you hoping to help create?
Looking five to ten years ahead, I want to build on the true meritocracy here at Citi. My focus is on a deep, durable leadership pipeline where the next generation is prepared for and stepping into senior roles, ready to run the firm and succeed our most senior leaders.
Equally important is an environment where inclusion shows up in outcomes. Our leadership should reflect the communities and clients we serve, and every colleague should have the same opportunity to grow, to lead and to succeed based on performance, potential and ambition. If we keep investing in people and creating real mobility, Citi will be even stronger, more inclusive and positioned for long term success.
Q: What practices help you sustain energy and resilience?
Staying connected to purpose, spending time with my family and staying close to colleagues keeps me grounded and energized. And for balance, I carve out one hour of Orangetheory Fitness almost every day– the best reset is 60 minutes of self-care.
Q: What are you passionate about in your personal life?
Outside of work, I’m passionate about giving back, especially when it comes to youth development and community programs. My years with the Riverside Hawks — as a parent, board member and advocate — have been some of the most meaningful experiences of my life. I also serve as Vice Chair of the Bedford Stuyvesant Restoration Corporation, which has been a cornerstone of Central Brooklyn for decades.
Service has always been a big part of who I am. I’ve been an active member of Delta Sigma Theta Sorority, Incorporated for more than 35 years, and I’m also a proud member of The Links, Incorporated. And staying connected to my alma mater is important to me too, so I continue to give back through my work on the Columbia Business School board.
OP-Ed: International Women’s Day 2022: Burnout, Sustainability and What Matters?
Career Advice, International Womens Day, NewsAs we enter year three of the global pandemic, with so many of us doing extreme amounts of work, and some of us also still balancing childcare with covid related closures of daycares and schools, isn’t it time to ask ourselves how can professional women and men (and especially anyone who has second and third shifts with kids and aging parents) do balance and self-care, better? What matters? And what role do firms have in creating the workplace of the future that we are ready to be in, now? This International Women’s Day, the manifesto should be to take a day off. Tomorrow the work will still be there!
Overwork and Burnout
There is work and then there is overwork. Chances are if you are reading this article, you have spent at least some of your career in the overwork zone. You probably work in financial, legal or professional services, in technology firms, big pharma, manufacturing, media or Fortune 500. You are probably a go-getter, highly ambitious and very successful. You probably have engaged some of the usual methods and possess some of the characteristics often needed to get to the top, including old fashioned hard and long work, a competitive nature, cognitive smarts, higher than average EQ to read the room, and a belief that improvement is always possible. Possibly three generations of professional women are reading this article with similar, yet evolving, culturally programmed definitions of success regarding wealth, status and career ladder climb concepts.
Is the extreme achievement mindset in sync with your life goals, your health and mental wellness? Is overachievement about meeting other people’s standards or earning your worth?
Dr. Devon Price, like many of us, came to his senses regarding extreme productivity after a health emergency. He insists that we should stop valuing ourselves in terms of our productivity at work. In the book, Laziness Does Not Exist, he affirms that ‘we don’t have to earn our right to exist’ with overwork and endless achievement.
Advice includes to listen to your body and to forget grinding away all the time to meet arbitrary standards. By reframing what being ‘lazy’ means, versus the allure of validation through achievement, a healthier, happier you can emerge.
“Laziness is usually a warning sign from our bodies and our mind that we need a break.”
In an interview with NPR, he discusses why we rationalize working so hard, and how asking for help, and helping others to helps us, prevents tiredness from overwork but also facilitates us to be better , due to feeling less exhausted as “our brains take micro-naps either way.”
It isn’t just you.
In several recent studies, isolated overwork came up as the most demotivating factor and biggest reason people are quitting jobs. This isn’t new news. Back in 2017, Inc magazine reported on employees quitting when leaders overwork people, show zero empathy and don’t respect time when people are out of the office living their lives, but it is further accentuated by the pandemic. Microsoft conducted an employee indexing survey of 30,000 that resulted in a study called “The Next Great Disruption is Hybrid Work – Are we Ready?”
By looking at trends including desire for flexible work and hybrid structures, the study reiterated what their CEO Satya Nadella called the hybrid work paradox. This study reveals that while people want more flexibility and remote options, they also seek deep human social connection. The same study reveals that high productivity is masking employee exhaustion and overwork. It states measurable uptick over the course of the year – February 2020 to February 2021 – on volume of emails sent, 66% increase on people working on documents, and meeting usage on teams increased in volume and time on meeting applications.
Uncovering your own Competing Agendas
Isn’t it time you figured out what you want for you? Start with your values. Take a look at what matters to you on this worksheet – literally, pick ten words that mean the most and then rank them 1-10, with one being what you value most. Are your actions matching your values? Are you living a humdrum existence while your top value is adventure? Are you spending fourteen hours a day at work when your top value is family? Now is a great to re-evaluate what matters to you. Be yourself, everyone else is taken as the adage goes.
If you had trouble thinking about how all of this meets reality, or deciding what your values are , or felt conflicted, that is part of the journey too. Hyper achievement and superhuman productivity are sometimes part of deep developmental gremlins that have made their way into our heads over time, so we can’t see any other way to be, making them our base operating system with everything else being an app on top. Kegan and Lahey, Developmental psychologists at Harvard, really have a superb method in their book, Immunity to Change, to help you figure out what your unconscious mind is doing to you while you happily goal set in your conscious mind all day long regarding work, fitness and home life. We are all a product of whatever beliefs and paradigms that we have accumulated throughout our life and if your granny/dad/mother/friend told you words to live by, chances are you are doing just that, implicitly following some guidelines without even knowing.
What are your saboteurs? There is another easy way to find out what is going on inside your own head by taking this short quiz on “How we self-sabotage” by Positive Intelligence. It is key to understand what is going on with yourself and what your self-talk is likely to be telling you. Let’s start with the gremlins. If you have something like hyperachievement as your top saboteur, then it is likely you will justify the overworking with sentences like ‘I must be effective and efficient, and ’emotions get in the way of performance.’ Or if you have a high control saboteur, you might be telling yourself things like, ‘well if I don’t do it, who will?’ Or, that people need people like you to get the job done. Show yourself some compassion and a great book to understand how to even begin to approach such a daunting task is Radical Compassion by Tara Brach. It is normal to feel your feelings and that includes joy.
In short, honor yourself on International Women’s Day by taking stock of what matters to you now, and how closely your own life feels aligned to that.
We are starting a Spring coaching cohort in May for sustainable success in 2022. Cost is $3,999 per person and includes a yearlong program with 6 sessions of executive coaching, peer coaching and career development training. Limited spots, contact nicki@theglasshammer.com and write spring coaching cohort in the title of the email.
By Nicki Gilmour, Founder and CEO of theglasshammer.com
Nicki founded theglasshammer in 2007 to inspire, inform and empower professional women in their careers. We have been the leading and longest running career advice online and in person media company in the USA for professional women in financial services.
Sustainable Success in Sustainable Industries
Career Advice“What inspires me is building toward a world where efficiency isn’t dependent on awareness or manual control,” says Saha. “Where buildings aren’t passive consumers, they’re responsive systems. That future is technically possible right now. The gap is in how we think about this problem, not in the technology.”
We spoke with Saha about what drives her, what she’s learned building a deep tech company, and the future she’s working toward.
Start with the System, Not the Person
Saha’s path into energy didn’t begin with engineering. Her first job was in marketing, working on Earth Hour, the campaign where people switch off their lights for an hour to make a statement about energy. It was there that a contradiction became impossible to ignore.
“I remember seeing large commercial buildings fully running late at night — cooling systems, lights, everything on — in Cyber City Gurgaon. We were asking people at home to switch things off, while buildings around us consumed at a scale no individual action could offset.”
The dissonance stuck. “We expect people to behave like energy experts. Most people can’t, and realistically, they won’t. So why are we trying to change human behavior instead of fixing the system itself?” That question led to Enlog.
For anyone building a career in sustainability or deep tech, this reframe matters: the most durable solutions don’t rely on changing what people do. They change what the system does by default.
Clarity Is What Scales
The journey from that early question to a functioning company wasn’t linear. “Deep tech is not a straight path,” Saha says. “There are long gestation periods, failures, and iterations. Delivering something truly breakthrough takes that. It’s not about small deltas.”
What kept her oriented through it was a commitment to first principles thinking. “You come across many opinions along the way. But real collaboration happens with clarity and that’s how you actually scale.”
That discipline shows up especially during hard stretches. “In deep tech, cycles are long. You’re not just building a product; you’re building trust in a new way of doing things.” When momentum stalls, Saha returns to the ground truth: “What does the data say? Where is the real inefficiency? That clarity cuts through opinion and noise.”
The Two Skills That Will Define Future Leaders
Ask Saha what capabilities will matter most going forward, and she doesn’t name a technical domain. She names two qualities that are harder to develop and easier to underestimate.
“One is emotional intelligence, not just in managing people, but in navigating uncertainty without overreacting. The ability to stay clear-headed when the situation is genuinely ambiguous.”
The second is synthesis. “Leaders today don’t struggle from lack of information. They struggle from too much of it.”
The ability to take multiple signals — data, context, external shifts and quickly identify what actually matters is increasingly where leadership leverage lives. These two skills reinforce each other: emotional grounding creates the conditions for clear thinking, and clear thinking makes decisive action possible.
Let Your Team Raise Your Standard
When asked who has shaped the way she leads, Saha’s answer is her team.
“I’ve watched them go deep into problems that most people would have given up on, break down assumptions, question the obvious, come back with insights that changed how we think about the product entirely. That level of depth is rare. And when you see it consistently, it quietly raises your own standard. You stop accepting surface-level thinking from yourself.”
The environments and people you choose to work alongside don’t just affect output, they recalibrate your baseline.
Knock on More Doors — Simultaneously
The most useful advice Saha has received is also the most literal: knock on more doors.
“Whether it’s partnerships, deployments, or policy conversations, I don’t depend on one path. I keep multiple conversations alive simultaneously. Some open fast. Some take a year. But the moment you limit yourself to one or two, you’ve already slowed yourself down without realizing it.”
Career opportunity works the same way. A single application, a single mentor, a single network, these create fragility. Building in parallel, even when one path looks most promising, is what sustains momentum across the long cycles that meaningful work requires.
The Permission You’re Waiting For Isn’t Coming
Saha has spoken with over 800 students across colleges, particularly young women without access to strong networks early on. The pattern she sees most often has nothing to do with ability.
“Most of them are genuinely capable, but they’re waiting for someone to tell them it’s okay to go. That permission never comes from outside. That’s the thing I try to leave them with.”
Her other consistent message: go deep. “Don’t just execute what’s asked of you. Think about how what you’re building can scale beyond you. Ownership and scalability together is where real impact lives.”
To her younger self, she’d say the same: “You saw the problem clearly. You just needed to trust that seeing it was enough to start.”
A Different Kind of Sustainability
Saha’s vision for the next decade is specific: “I want to help build a world where managing energy becomes invisible. Where buildings understand and optimize their own consumption in real time — without waiting for someone to notice, without depending on manual intervention.” If that becomes standard, she argues, “efficiency, in that sense, becomes a primary energy source.”
As Saha puts it: “The real constraint in the next decade won’t be generation. It will be how intelligently we use what we already have.”
Powering the Future: Carey Ryan, Chief of Staff for Citi Technology & Business Enablement, Citi
People, Voices of ExperienceNicki: Since we last spoke, where are you now?
Carey: We last spoke for the first time about 10 years ago, which seems like a long time but feels like the blink of an eye. I’ve held a number of roles since then, all within Citi’s Technology & Business Enablement group (though the name has changed a few times).
Now, I am the Chief of Staff for Citi Technology & Business Enablement. This entails working across both our technology organization and the wider bank to ensure we are effectively communicating and implementing new technologies, both with the goal of strengthening how we work and streamlining the time it takes to get work done.
Nicki: How did you get there?
Carey: In my 20 years at Citi, I have learned the best way to grow is to embrace every opportunity, especially if it allows you to learn more about how a company works. All of the roles I have had have allowed me the opportunity to support key areas of the business, including risk and control, data, and cybersecurity, each of which are vital to ensuring impactful technology can be developed or invested in and scaled to the full firm.
Nicki: Can you share a little about your current work?
Carey: Lately, much of my focus has been driving adoption and awareness for our Citi AI tools, helping us find the best places to practically and responsibly implement AI. This work includes leading our AI Champion and Accelerator programs, which are made up of approximately 4,000 volunteers around the firm who dedicate hours each week to serve as Citi AI advocates.
I also spend a lot of time working with our technology communication teams, each of whom covers a specific but global vertical within the larger technology business. No communication initiative is turnkey, and we always work to find new ways to impactfully reach colleagues with the information they need, be it in-person mediums like executive town halls or roundtable discussions, or through digital channels like email or lobby signage. Technology is the largest organization within Citi, so it’s key to focus on communication to enable change and drive execution while strengthening our culture.
Nicki: Have there been any unexpected or interesting twists in your career trajectory?
Carey: I have always worked in or adjacent to the technology space so, even before I recognized it, I was always headed for a career in enabling companies to leverage new technology to strengthen how they operated. That said, the world looks measurably different than it did when I entered the workforce, and Citi is no different. Some of these changes came quickly, such as the introduction and integration of AI, that has demanded the need to quickly shift priorities without much advance warning.
Nicki: Have any of them taught you a valuable lesson?
Carey: Citi is a large company, so I have had the opportunity to work on many projects with many people. Given this, the two key lessons I would share that always keep in mind is to always remember the end goal of every project and to stay flexible.
Nicki: What inspires you to be a leader and your leadership style?
Carey: My favorite part of my role is collaborating with dedicated and passionate colleagues. Whether it be the implementation of cutting-edge software, the voluntary work of a small team creating new patented technology tool, or an analyst successfully completing their first rotation with the bank – it is the passionate, innovative and solution-focused people that inspire me each day.
As I have risen in my career, I strive to be a good mentor and reliable leader for all members of my team, regardless of level. I’ve been lucky to have had several mentors whose advice I still hold on to, and it’s important to pay it forward. I also can’t help but think of my teenage daughter, I want to set a positive example for her as well as for my teams of what is possible in their careers and how leaders should treat their employees. An example that, hopefully, they will one day share with their own teams and mentees.
Nicki: Since we last spoke, can you share any challenging moments, setbacks, or self-doubt you’ve experienced as well as how you have navigated them?
Carey: I’m not sure I can pinpoint just one moment, but every new challenge I am presented with comes with a bit of imposter syndrome when I do not immediately have all the answers. Almost everyday features at least one conversation about something that where either I’m not the expert or the topic is completely new to me. It can be hard to ask questions when you think everyone except you has the answer, but the ability to step out of your comfort zone and know that you add value is a skill that will never go out of style. Self-doubt is something everyone faces, and the unknown is allowed to be scary. The key is being confident in your own ability to learn and adapt to problem-solve when navigating an unfamiliar situation.
Nicki: What skills do you think will matter most for future leaders?
Carey: When I was younger, I always assumed the fear and anxiety I felt about the unknown would go away. That one day I’d wake up and know everything there was to know about my job. But you quickly figure you’ll never know it all, because the world is always changing. Instead, I found the key is to always be ready by learning how to operate effectively with uncertainty and always be willing to learn.
Future leaders must be willing to be agile and adaptive, especially as the pace of change in the world continues to increase. AI is a great example of this. It is an unavoidable technology, and we should be willing to integrate it into how we work.
Nicki: Can you share an invaluable, specific piece of guidance a mentor or someone you admire has imparted on you?
Carey: I’ve had a number of tremendous mentors over the years. What I admired most in all of them was not any guidance they offered me, but the way they all led through their actions. Each of them led with kindness and empathy, listened carefully and accepted all forms of feedback, and were more than willing to change course if something was not working.
Nicki: Has coaching supported you in your journey, and if so, how?
Carey: Yes, I’ve been very fortunate to have had several coaches throughout my career. Coaches who were mentors, coaches whose job it was to support me, and coaches who were my peers. Career coaching offers an objective view of your decision-making. This often leads to introspective reflection on ways you can reframe your thinking, which is invaluable.
We can all sometimes be so goal-oriented, but it’s critical to take a step back and reflect on if we are taking the right steps to reach these goals. I often find myself going into my coaching session with one idea of what we will talk about and coming out with an entirely new perspective. Sometimes, the external guidance that a career coach offers is what one truly needs to help unlock those ‘aha’ moments.
Nicki: We are excited to see what you do next at Citi; we wish you continued success!
Beyond the Performance Review: The Assessments That Build Self-Aware Leaders
Career Advice, Career Tip of the Week!But even with all that experience, there can be a moment where a promotion goes sideways, a team isn’t performing, or a stakeholder relationship never quite clicks. Where the question stops being what do I need to know and becomes what do I need to understand about myself?
That is where coaches who are skilled and qualified in psychometric assessments can be particularly useful as there is value in triangulating this data as a third piece to add to “you, according to you” and formal or informal feedback from others.
Why Self-Awareness Is a Strategic Necessity, Not a Soft Skill
Organizational psychologist Tasha Eurich, whose research involved studies with nearly 5,000 participants, found that while 95% of people believe they are self-aware, only about 10 to 15% actually meet the criteria when objectively assessed. In leadership, that gap has direct consequences for the people you lead and the outcomes you are responsible for.
For women in senior roles, the stakes are compounded. Catalyst’s well-documented research on the double bind describes a dynamic many readers will recognize: behaviors that read as confident and decisive in a male colleague are routinely perceived as aggressive or abrasive in a woman, while collaborative and approachable behaviors can be coded as lacking authority. The margin for misreading your own impact and for having your intentions misread by others is narrower.
Self-awareness, in this context, is political and strategic intelligence and creates an opening for situational awareness. Understanding how your behavioral tendencies are landing, and to learn to watch if there is a gap between “your intent and your impact” is the growth work in coaching. What you default to under pressure is integral to separating leaders who plateau from those who keep growing.
The good news is that this is not guesswork. At Evolved People Coaching, the four tools we use most often each answer a different question and we work with you to identify which one is the right fit for where you are right now.
Four Questions Every Leader Needs to Answer:
1. How do I naturally behave — and how is that landing in different situations with different people?
Tool: DISC Assessment
DISC maps your behavioral tendencies across four dimensions: Dominance (how you respond to challenges), Influence (how you engage with people), Steadiness (how you respond to pace and change), and Conscientiousness (how you approach detail and process). It is not a measure of intelligence or potential; it is a map of your default operating style.
What makes DISC particularly powerful is what it reveals about the distance between how you experience yourself and how others experience you. Consider a senior leader who describes herself as direct, efficient, and results-focused. Her DISC profile confirms a high Dominance pattern. Her feedback tells a different story: her team finds her unapproachable, and two high performers have quietly started looking elsewhere because they feel that their leader cannot hear their ideas and it is not worth it to bring up risks. She isn’t doing anything wrong by her own logic, but without understanding how her style lands with others and adjusting accordingly, she creates an impact she never intended.
This is the gap DISC is designed to close. Not by changing who you are, but by making your behavioral defaults visible so you can choose when to lean in and when to flex.
2. Is my team actually working — or just coexisting?
Tool: Five Behaviors of a Cohesive Team
Individual self-awareness will only take you so far if the team around you isn’t functioning. The Five Behaviors of a Cohesive Team, based on Patrick Lencioni’s widely used model, assesses team health across five dimensions: trust, productive conflict, commitment, accountability, and results orientation.
The tool operates at two levels. For intact teams, every member completes and debriefs the assessment together. What typically surfaces is a shared picture of where the team is genuinely cohesive and where it is performing a version of cohesion that is actually conflict avoidance or surface-level commitment masking real misalignment. For leaders who have inherited a team, are navigating a restructure, or aren’t getting the performance they expect from talented people, this version provides data where there was previously only intuition.
For individuals, a separate assessment helps you understand how you personally show up as a teammate regardless of whether your whole team is participating. This is valuable for leaders stepping into a new environment, those who have received feedback about their collaborative style, or anyone who wants to be more intentional about their contribution to team dynamics. Rather than waiting for the whole team to be ready, this version puts the insight in your hands immediately.
3. How am I actually landing with the people around me?
Tool: Qualitative 360 Assessment
A qualitative 360 goes directly to the source: the colleagues, direct reports, peers, and senior leaders are all stakeholders who experience your leadership every day. Conducted through structured confidential interviews rather than numerical ratings, it surfaces the specific behaviors that are building your reputation and the ones quietly working against you — patterns that no behavioral profile can predict, because they are grounded in the specific context of your organization and your relationships. There is huge psychological safety for the feedback givers because the data collected is anonymized and themed by topic so no comments can be attributed to anyone.
Used well, a qualitative 360 is not an appraisal. It is a rare opportunity to hear, in a safe environment, what people genuinely think and what they wish they could tell you directly. Given the depth of work involved, this is an assessment we typically offer as part of organizational engagements, but for the right leader at the right moment, it is one of the most powerful development investments available.
4. How can I change the behaviors that are hindering my highest potential?
Tool: Immunity to Change Mapping
The Immunity to Change Map process is a tool to uncover any hidden constructs in your subconscious mind that might be covert to you and therefore stopping you from doing the things you need to do to achieve your goals (that are overtly set in a goal setting exercise).
Nicki Gilmour, Founder of Evolved People coaching and theglasshammer.com states,
“Truly, this map is so useful early on in any work with our clients because it skillfully surfaces any or sometimes many implicit constructs that form a type of operating system or deep structure that left untouched, would result in most people wondering why they cannot do the day to day behaviors that would easily enable them to achieve their goal. This applies to any area of change, from working out to delegating work, to speaking up at meetings and even changing careers.”
Finding the Right Starting Point
These four tools address different levels of leadership insight: your default style, your team dynamics, your hidden limiting beliefs, and your real-world impact on the people around you. For most leaders, one will be the clear priority based on where you are in your career, what feedback you have received, or what challenge is most pressing. Our role is to help you identify which one that is, and to make sure the debrief and coaching that follows translates the data into something genuinely useful.
For organizations, our team development workshops use DISC, The Five Behaviors, and even Immunity to Change at a group level for leaders to build the shared visibility and common language that turns a group of talented individuals into a genuinely high-performing team.
The leaders who invest in this work consistently tell us the same thing: they wish they had done it sooner.
If you are ready to close the gap between the leader you are and the leader you intend to be, we would love to talk. Visit evolvedpeoplecoaching.com to explore our coaching programs and team development workshops, or get in touch directly to discuss which assessment is the right starting point for you.
Christina Bresani: Head of Mid-Cap Investment Banking, Wells Fargo Corporate & Investment Banking
People, Voices of ExperienceAsk Christina Bresani, Wells Fargo’s head of Mid-Cap Investment Banking, about a recent client visit and she’ll tell you about climbing into the cab of a semi-truck in high heels and passing a driving simulator test to show her client that she understood their business. That story captures everything about how she approaches her work: with genuine curiosity, a willingness to go wherever the client takes her, and an infectious enthusiasm that has sustained nearly three decades in investment banking.
After 25+ years as an M&A banker at two previous firms, Bresani joined Wells Fargo in 2024 as head of Mid-Cap M&A within the firm’s Global M&A business. In November 2025, she took on the expanded role of leading the firm’s Mid-Cap Investment Banking Practice focused on serving mid-cap clients and delivering investment banking products and services to the bank’s Commercial Banking clients. It’s a dual mandate she wears proudly, and one that plays an important role in Wells Fargo’s Corporate & Investment Banking growth strategy.
“When you love what you do, it’s easy to put your head down and keep doing it,” says Bresani. “But what I saw in Wells Fargo was a new challenge to do what I love and help build a leading corporate and investment bank that can bank companies along the whole spectrum of their growth – from mid-cap to large-cap and beyond.”
Building Something That Lasts
The challenge of building out and developing the Mid-Cap Investment Banking team is one that Bresani finds genuinely energizing. “Creating a strategy, building a team that’s going to be successful in the near term and the long term, is really inspiring to me right now,” she says. “That’s hiring people. It’s getting the strategy right. It’s keeping people motivated because when you are building something, it’s not always a straight line.”
She notes that the foundation of any great team comes down to one word: trust.
“The goal is to build a team with a talented group of people who have the same values and want to lock arms to be successful together. It’s not only about individual success, it’s about elevating the entire team and constantly learning from our collective successes and failures,” she says. “This has always been important to me as a leader and it’s central to Wells Fargo’s culture.”
A Career That Kept Saying Yes
Bresani started out as an analyst, fully expecting to spend two or three years in banking before figuring out what she really wanted to do. Nearly three decades later, she’s still there — and still surprised by it. “Every year I would say, ‘wow, I want to do this, I want to learn this, I want to get better at this,’” she says. “And I just kept going.”
She credits a great deal of that staying power to the mentors who showed up early and stayed. “I was really lucky in my early days to have two amazing mentors: both men. That’s important for young women in the industry to know – you don’t have to only have female mentors.” Those relationships, she says, were as much personal as professional. ” They were ‘work dads’ in the sense that they really guided me and cared about my professional and personal growth. To form those kinds of relationships really makes a difference in this business which can sometimes be tough”
The Moment That Tests You
When asked about setbacks, Bresani reflects on one of the most universal and quietly defining moments in a banker’s career: the first time a client pushes back hard.
“There is always a point in your career where a client doesn’t like you or doesn’t like the advice you’re giving,” she says. “The first time that happens, it’s really hard not to take it personally.”
Just recently, she watched a director on her team navigate exactly that situation. Rather than letting it become a crisis of confidence, Bresani chose to reframe it. “I told him: this is your pivotal moment. Here’s how we help you pick yourself up. Here’s your opportunity to really do your job.” She recalls her own version of that moment as a first-year director, when a mentor stepped in, defended her and then told her precisely what she needed to do better. “You have to learn that not everyone is going to agree with what you say, and you have to have a thick skin. But ultimately, this is a client service business. Not every client is the same, and you have to adjust.”
Fueling the Long Game
How does someone sustain nearly 30 years at that pace without burning out? Bresani takes it one day at a time and deliberately so. “It’s easy in this job to get overwhelmed with everything that has to be done,” she says. “I’m very focused on what needs to get done today, what can wait until tomorrow, and making sure I am prioritizing what is important versus being driven by what is urgent.”
But the off switch matters just as much.
“I have three children, an amazing husband, a menagerie of animals, and I am committed to exercise even if it means a 4.30am workout. I find a way to exercise because I need it. Whatever it is, it’s important to find those things outside of work that make you happy and fill your energy cup.”
Another factor to staying happy and healthy she attributes to friendship, a group forged at an all-women’s college that has stayed tightly bound across careers and time zones. “We have a text chain,” she says, laughing. “We build each other up. We laugh and say, ‘You will never believe what happened today,” She pauses, then finds exactly the right phrase for it: “It’s a group hug via text.”
Still Having Fun
When Bresani’s kids ask her about her day, they don’t want the deal mechanics. They want to hear about the people. “I come home and my kids say, ‘Mom, tell me about the people you met today,’” she says. “I meet the most interesting people.” That, more than any title or transaction, seems to be the through-line of her career. She still operates by a simple rule she set for herself long ago: “I’ll stop doing it when it’s not fun anymore. It’s still really fun.”
By Nicki Gilmour, Founder and CEO of theglasshammer.com and Evolved People Coaching.
Radical Candor: A Practical Approach to Accountability on Teams
Career Advice, Career Tip of the Week!That gap matters. Because when teams cannot reliably follow through on what they agree to, it becomes difficult to build momentum, make decisions stick, or deliver consistently as a group.
For many teams, accountability is one of the hardest behaviors to translate into practice. It is easy to agree, in principle, that teams should hold one another accountable. It is much harder to know what that looks like in real conversations, especially when relationships, power dynamics, and organizational pressures are in play.
Why Accountability Breaks Down
The Five Dysfunctions of a Team framework offers a clear model for what teams need in order to be effective and cohesive. Accountability sits near the top of the pyramid, build on a foundation of trust, productive conflict, and clear commitment. Teams first need to be able to have vulnerability-based trust, then healthy debate, then clear decisions. Only after that can people realistically hold one another accountable.
What the model does not always answer is how accountability conversations actually happen.
Even well-resourced, strategically aligned teams can struggle to sustain accountability. The challenge is not a lack of intent, but the nature of the behavior itself. Holding someone accountable requires naming something uncomfortable. It requires you to say, out loud, that an agreement was not met and to do it in a way that preserves the relationship, the trust, and the team’s ability to move forward.
When those conversations do not happen, the ripple effects go well beyond a missed deadline. People may stop raising concerns, stop pushing for clarity, and over time, stop believing the team can deliver on its shared goals.
So, if accountability is so central to team effectiveness, why is it so hard to sustain?
Because at its core, accountability requires uncomfortable conversations and many of us were never taught how to have them well.
A Framework for Accountability Conversations: Radical Candor
One useful framework for navigating these conversations is radical candor. Coined by Kim Scott in her book Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity, radical candor is an approach to communication that emphasizes two things at once: challenging directly while caring personally.
This is not the same as “brutal honesty.” In fact, in Scott’s framework, brutal honesty sits in a quadrant she calls Obnoxious Aggression, characterized by being critical without caring, or being clear but not kind. For example, public callouts, sarcasm disguised as feedback, or “I’m just being honest” used as an excuse to be harsh.
Radical candor, by contrast, is about having compassion while being transparent. It means being willing to say the hard thing while staying connected to the humanity of the person you are speaking with. It assumes positive intent, even when addressing negative behavior.
Scott’s model also includes two other quadrants that illustrate what it looks like when communication is not balanced between caring personally while challenging directly.
Ruinous Empathy sits in the quadrant of high care, low challenge. This is what happens when someone avoids giving clear feedback to spare feelings or keep the peace, absorbing someone else’s missed deadline rather than addressing it or letting a pattern continue because “they’re going through a lot right now.” It feels compassionate in the moment, but the person never receives the information they need to improve, and the team quietly absorbs the cost of a problem that was never named.
Manipulative Insincerity falls in the quadrant of low care, low challenge, and looks like “nice to your face, critical behind your back.” A team member agrees to a plan in a meeting but complains privately that it is unrealistic. A leader avoids addressing missed commitments directly while venting about them to peers. This behavior is particularly toxic because it erodes the trust that is fundamental to a cohesive team.
Radical Candor Is Not Just for Managers
While the revised edition of Scott’s book is subtitled “Be a Kick-Ass Boss Without Losing Your Humanity,” she is clear that radical candor is not meant to be hierarchical. It should be practiced up, down, and across. Teams are strongest when everyone feels responsible for naming issues and maintaining shared standards.
Practical Ways to Apply Radical Candor
Let us look at some examples of how to use radical candor to maintain accountability on a team, whether you are speaking with your direct report, colleague, or leader.
Leader to Direct Report
In this context, the leader’s role is not just to manage performance, but to protect the team’s agreements:
Here, care is shown through respect and support; challenge is shown through naming the pattern and its impact.
Peer to Peer
This is the kind of accountability that is truest to Patrick Lencioni’s use of the term in his Five Dysfunctions of a Team model:
The script above works because it opens with relationship, not accusation, and grounds the challenge in shared impact rather than personal frustration.
Direct Report to Leader
While giving feedback in an upward direction may feel risky given potential power dynamics, if psychological safety is present, it can reinforce shared commitments and strengthen trust:
When leaders invite and respond well to this kind of feedback, they model accountability as a shared value rather than a power dynamic.
Building Cohesive Teams in Practice
Accountability is not about policing behavior or enforcing rules; it is about protecting the team’s purpose.
Radical candor provides a practical way to do that without sacrificing relationships or culture. It creates a norm where people can name issues early, address them directly, and move forward together.
Ultimately, accountability is a form of respect. It says: Our work matters. Our goals matter. And we value each other and our team enough to have the conversations that matter.
Without it, teams may remain polite, but they will never become truly cohesive.
At Evolved People Coaching, the coaching arm of theglasshammer.com, we work with leadership teams who are looking to transform the way they work and bring their team to the next level. Our team development workshops draw on the Five Behaviors of a Cohesive Team framework alongside evidence-based communication approaches like Radical Candor, helping teams move beyond theory into real conversations. We work alongside teams to build the trust, language, and habits they need to navigate conflict productively, hold one another accountable to shared commitments, and deliver meaningful results together.
Contact us to learn more!
Powering the Future: Erika Irish Brown, Head of Talent Management and Engagement, Citi
PeopleAs part of The Glass Hammer’s Where Are They Now series, we are catching up with leaders we have spoken with before to see how their careers and perspectives have evolved over time. Erika Irish Brown, now Head of Talent Management and Engagement at Citi, has long been focused on creating opportunity and building inclusive workplaces. In this next chapter of her career, she shares how that mission is expanding as organizations rethink leadership, mobility and learning in an era defined by rapid technological change.
Q: What are you currently working on?
As Head of Talent Management and Engagement at Citi, my focus is on our global, talent centric approach to supporting our workforce—one that invests in people, creates opportunities for growth and fosters a culture where everyone can thrive.
Our team leads all of Citi’s efforts around development planning, talent designations, talent processes and succession planning. We also oversee enterprise coaching, our engagement activities including 12 global Inclusion Networks and Talent Management and Engagement Councils across each business and function.
Q: What is inspiring you to lead in the future?
What inspires me about leading into the future is the real momentum we’re building at Citi. We have a clear strategy, a leadership team driving meaningful change and a firm accelerating on every front, including technology.
AI is opening new doors for our people, helping colleagues find opportunities that match their skills and aspirations. As it becomes more integrated into how we work, it will continue to fuel growth, innovation and faster execution.
You can see this momentum in our focus on mobility. In 2025, we filled more than 55,000 roles with 44% coming from internal moves and promoted over 28,500 colleagues into new roles. And with initiatives like Development 365, more than 165,000 colleagues created personal development plans last year.
The combination of our strategy, our people and the possibilities technology unlocks makes the future incredibly energizing.
Q: What makes Citi special?
What makes Citi special is the combination of our globality and our focus on human-centered leadership. As the world’s most global bank, we have people on the ground in more than 90 countries, which gives us a unique level of cultural fluency. It allows us to connect with colleagues where they are, listen to their experiences and ensure our strategy reflects the realities of each market. Our clients tell us this reach is a true differentiator.
Our scale also means we tackle complex challenges across borders and offer a wide range of roles and career paths within one firm. That combination of global breadth and opportunity is hard to find anywhere else.
What also sets Citi apart is our leadership. Jane Fraser, our Chair and CEO, leads with a clear vision, and her leadership shapes a culture of understanding from the top. She is a trailblazer in financial services and the first woman to lead a major financial institution. Our global footprint – who we are, where we are, and the businesses we run—makes Citi a truly special place to grow and make an impact.
Q: What lessons in leadership have you learned working at the world’s most global bank?
I’ve had the privilege of working at several of the world’s leading financial institutions, and those experiences have deepened my understanding of culture and lived experience and reinforced that ambition and leadership show up differently around the globe. Leadership is packaged in all different ways, and that has underscored the need for our leadership frameworks to evolve.
We have to break the myth that there is only one archetype of a leader, especially when it comes to succession planning. Not everyone will say, “I want to be CEO.” Many people are quiet leaders, and that doesn’t make them any less ready for what’s next.
Leadership doesn’t begin with a title — anyone can lead, and leadership can be shown at every level. At Citi, we measure leadership against three principles: we take ownership, we deliver with pride and we succeed together. Whether you lead a large team or contribute as an individual, how you bring these principles to life is what truly matters.
Q: How have you navigated challenging moments, setbacks or self doubt?
Navigating difficult moments starts with remembering that meaningful and sustainable change doesn’t happen overnight. Impact builds over time. I try to focus on what I can control and release what I can’t. At the end of each day, its important that I am able to look in the mirror and know I used my voice—especially when it was uncomfortable or challenged the status quo. I believe silence is a form of endorsement; if I’m not willing to speak up, then who will?
Setbacks are part of the process, but I stay grounded in my competence and confidence. If you’re competent, you have every reason to be confident. Mistakes are okay as long as you take feedback, course-correct quickly and keep moving. Learning agility and making progress matters far more than perfection.
When things don’t work out, I remind myself that there may be something else in God’s plan. Faith helps keep everything in perspective. And if I can honestly say I fought the good fight and did my best on behalf of others, I can move forward with confidence.
Q: What skills do you think will matter most for future leaders?
Future leaders will need learning agility above everything else. The pace of change is only accelerating. Today it’s AI, but we don’t yet know what we’ll be navigating tomorrow. 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.
Being a lifelong learner is no longer optional—it’s a leadership requirement. The leaders who succeed will absorb new information quickly, adapt their approach and translate what they learn into action.
At the heart of learning agility is staying curious —the willingness to ask questions, seek out new perspectives and lean into what you don’t yet know. Curiosity keeps you growing, keeps you adaptable and keeps you ready for what comes next.
Q: Who inspired or influenced you most on your journey, and what did you learn from them?
My parents are my biggest inspirations. They set high expectations, especially around academics and STEM. My mother was a junior high math teacher, and my father rose through the New York City Housing Authority to become Head of Computer Services. In our house, if your grades weren’t where they needed to be, the question wasn’t “Did you try your best?” It was “What happened?”
They taught me to be a change agent. If something wasn’t the way you wanted it to be, you had the power and the responsibility to fix it. That mindset shaped me. You have agency. You can challenge the status quo. You can create opportunities that don’t yet exist.
They also taught me the value of effort and the associated outcomes. What you put into something is what you get out—karma. Education, hard work and smart risks can change your life’s trajectory. Those lessons—accountability, agency and effort—have guided my career and influence how I lead today.
Q: What invaluable, specific guidance have you received along the way?
A few pieces have stayed with me:
Q: What do you impart upon those you mentor — or would impart upon your younger self?
Be ambitious, take stretch assignments and stay curious. Don’t assume your work will speak for itself — advocate for your own growth. And always consider the legacy you’re building. Making a difference doesn’t have to be grand; it can start with creating an opportunity for even one person to succeed.
Q: Has coaching supported you in your journey, and if so, how?
I have absolutely benefited from coaching. At Citi, executive coaching is a capability we invest in as part of our Talent strategy because we know it elevates performance; it’s not about fixing a problem. Just as elite athletes rely on coaches to refine their craft, high performing leaders gain so much from trusted advisors who help deepen self awareness, strengthen impact and navigate complexity with greater effectiveness. When we prioritize continuous development, we position our leaders and our organization to succeed in an environment that is constantly evolving.
Q: Looking ahead five to ten years, what kind of future are you hoping to help create?
Looking five to ten years ahead, I want to build on the true meritocracy here at Citi. My focus is on a deep, durable leadership pipeline where the next generation is prepared for and stepping into senior roles, ready to run the firm and succeed our most senior leaders.
Equally important is an environment where inclusion shows up in outcomes. Our leadership should reflect the communities and clients we serve, and every colleague should have the same opportunity to grow, to lead and to succeed based on performance, potential and ambition. If we keep investing in people and creating real mobility, Citi will be even stronger, more inclusive and positioned for long term success.
Q: What practices help you sustain energy and resilience?
Staying connected to purpose, spending time with my family and staying close to colleagues keeps me grounded and energized. And for balance, I carve out one hour of Orangetheory Fitness almost every day– the best reset is 60 minutes of self-care.
Q: What are you passionate about in your personal life?
Outside of work, I’m passionate about giving back, especially when it comes to youth development and community programs. My years with the Riverside Hawks — as a parent, board member and advocate — have been some of the most meaningful experiences of my life. I also serve as Vice Chair of the Bedford Stuyvesant Restoration Corporation, which has been a cornerstone of Central Brooklyn for decades.
Service has always been a big part of who I am. I’ve been an active member of Delta Sigma Theta Sorority, Incorporated for more than 35 years, and I’m also a proud member of The Links, Incorporated. And staying connected to my alma mater is important to me too, so I continue to give back through my work on the Columbia Business School board.
Futures Industry Gathers in Boca to Discuss Where Risk Management Ends and Gaming Begins
NewsThe Futures Industry Association (FIA) held their annual FIA Boca conference in Boca Raton, Florida March 8-11, 2026. The annual gathering brings together institutional investors and professionals in the listed and over-the-counter derivatives markets with an emergence of digital asset firms and retail brokers joining in the past few years.
One of the hot topics this year was the rise of prediction markets, which can be a useful risk management tool enabling participants to hedge against uncertain future events. However as these markets evolve, there is growing concern about when they cross the line from risk management tools to gaming and speculation?
A Repackaged Product
From a structural perspective, prediction market contracts are not new. Many of them are variations of instruments the financial industry has traded for decades. Most operate as fully collateralized products known as binary options. Binary options are contracts that only pay out a fixed amount if a specific event occurs. The buyer will only lose what he spent to buy the option if the event does not occur.
“Everyone is looking for what is next,” says Jim Kharouf, Chief Marketing Officer at IncubEx, which designs and develops environmental derivatives. “We have seen the evolution from the institutional derivatives to e-minis, and options to zero-day contracts and so on. Prediction markets, and even crypto, are more examples of the next layers of innovation.”
While versions of these contracts have existed since the late 1990s, new players have brought a wave of excitement, and potential for scale and scope. Last year, the CME Group announced a partnership with Fanduel (they hired former Chicago Bulls player Scottie Pippen to promote the products at this year’s FIA Boca conference.) Another recent partnership between InterContinental Exchange and Polymarket has brought additional buzz to the prediction market space. Other notable names include Robinhood and Draftkings.
The collaborations represent a shift in the derivatives markets. These exchanges, which traditionally service institutional and professional traders, are introducing event-based trading to a much broader audience with consumer facing platforms. While the foundation of the product has stayed the same, it is the entrance of new participants and the events in which they are trading on, which has brought up these pressing questions.
A Natural Progression
Christopher Hehmeyer, a derivatives industry veteran who was most recently CEO of Warwick Capital, says that we must reframe the issue in terms of public perception. He wonders whether the American public sees a meaningful difference between trading a contract on the next Taylor Swift concert and taking a position in gold.
“It’s gaming on U.S. entertainment versus risk management,” he says, explaining that betting on pop culture events may feel closer to traditional gambling than financial trading.
However, Hehmeyer also points to prediction instruments that serve a clearer economic purpose. Weather contracts, for example, allow businesses and individuals to hedge against environmental risks that can be difficult or expensive to insure.
Contracts tied to weather outcomes are traded on platforms such as Kalshi, a regulated U.S. exchange that offers event-based contracts on topics ranging from economic indicators to climate data.
“If insurance is too expensive, the option to buy a weather contract hedging against a hurricane is a type of risk management,” he says. “That’s not gaming.”
In that scenario, a business located in a hurricane-prone region might buy a contract that pays out if a storm strikes its area. The payout could offset revenue losses caused by the disruption, functioning similarly to an insurance policy.
This illustrates the central challenge regulators face. The same financial instrument can be used in very different ways. A coastal business might use a hurricane contract to hedge real financial exposure, while a retail trader in another state might simply be speculating on the outcome.
The debate therefore often centers less on the structure of the contract and more on the underlying event being traded. As prediction markets expand, this distinction is becoming increasingly important.
A Regulatory Impact
Finally, another complication is the regulatory framework itself. In the United States, prediction markets exist in a complex environment overlapping financial regulation and state gambling laws. Some contracts are treated as derivatives, while others may be restricted depending on how regulators interpret their purpose. Also, states may lose out on potential tax revenue, if there isn’t regulatory certainty and federal legislation, as trading activity shifts to platforms that operate outside of traditional gaming structures.
While prediction markets may be part financial innovation and part speculative entertainment, it is clear that the underlying idea is gaining momentum. As technology makes it easier for individuals to trade on real-world outcomes, prediction markets may become an increasingly visible part of the financial landscape. It is now up to the regulators and policymakers to decide where the line is drawn between real-world risks and betting on the unpredictable.
Powering the Future: Joanna Fields, CEO, Aplomb Strategies Inc.
PeopleBy Jessica Darmoni
“Future leaders must not only understand technology but wield it responsibly to protect reputational integrity in a world where data breaches and automation carry profound consequences,” says Joanna Fields, a financial market veteran who remains focused on enterprise risk management.
Fields has almost 30 years of experience spanning global asset classes such as equities, derivatives, fixed income, futures, treasury, digital assets and capital markets as well as experience with decentralized physical infrastructure networks (DePIN), telecom and utility industries. She has built a reputation not only as an enterprise risk management expert, but as a leader in market structure and financial governance. She sat down with The Glass Hammer to discuss the importance of resilience, reinvention and a human approach to leadership.
The Art of Balance
“This may sound like an unlikely beginning, but I started out as a professional ballerina,” says Fields, who has led market structure initiatives and designed risk governance frameworks.
As a dancer, she learned aplomb, which is the art of balance and stabilization under pressure. She learned teamwork, discipline, and the necessity of believing in yourself even when the spotlight felt overwhelming.
Fields may never have gone into finance, if it weren’t for a car accident that halted her dance career.
“It was a devastating moment and made me redefine not just my profession but my identity.”
Supported by her father’s steadfast commitment to the Socratic method of education which encouraged questions, analysis, and critical thinking; she took a risk into the world of finance and technology.
Fields started her career in market regulation at the Chicago Board Options Exchange and the International Securities Exchange. She went on to hold Head of Market Structure roles and lead compliance departments at Deutsche Bank Securities, Inc and Credit Suisse First Boston.
Her contribution to financial markets, as she describes it, has been “keeping it safer.”
Fields is good at identifying patterns of fraud and misconduct. She has developed surveillance tools to strengthen governance frameworks and has helped institutions avoid “gotcha” regulatory moments.
She believes there will be pivotal themes in 2026 including; how to use artificial intelligence safely while protecting data privacy, the rise of DePIN, emerging regulatory frameworks such as the Genius Act, and the increasing sophistication of cybersecurity fraud.
In a rapidly evolving technological environment shaped by AI, blockchain, DePIN, and crypto markets, her ability to merge technology with risk oversight has become critical.
Rising with Support and Purpose
While Fields has many professional achievements, her greatest source of inspiration is a personal one. In 2022, her daughter experienced sudden vision loss.
“We spent countless hours in a hospital room navigating all the uncertainties. It was a scary and emotional time but my daughter remained unwavering,” she remembers. “She continues to believe that women can do anything, build anything and achieve anything.
They found that sports, in particular softball clinics at Northwestern with dedicated coaches, shifted their perspective.
“We focused on what was possible instead of what had been lost. We had a strong team of family and friends around us that reframed the adversity as a challenge to be met with collaboratively.”
Throughout her journey, Fields has learned that unexpected challenges are inevitable. What matters is the community you build and the confidence you develop in your specialty over time.
“It’s about who you surround yourself with and who will help you rise. Everyone stumbles. What defines a career, or a life, is how you respond to it.”
Leadership is about Legacy, Not Titles
Fields has also dedicated time to mentoring students from Barnard College and Columbia University. Her advice to young women entering the workforce is practical and empowering.
“Try to get two offers and negotiate the best one. Know your worth. You will spend eight to twelve hours a day at work; choose a team you enjoy and respect. Do not be afraid to take risks. And when you are right, stand firm—while remaining open to negotiation and alternative viewpoints. If you are wrong, own it. Clear communication and thoughtful articulation,” she emphasizes, “are foundational to leadership.”
When asked what impact she hopes to create, her answer is twofold.
“I want financial markets to be safer. I want to be able to use technology proactively against fraud and misconduct.”
Fields also finds satisfaction in seeing those she has worked with grow into long-term careers of their own.
“Leadership is not about titles but about legacy.”
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 asserts.
From ballerina to financial risk strategist, from navigating personal tragedy to mentoring the next generation, Fields embodies aplomb in its truest sense: balance, grace and strength under pressure.
The Return on Investment for Executive Retreats
Career Advice, Career Tip of the Week!Executive wellness retreats are often judged by their immediate costs: time away from work, financial investment, and short-term disruption. But their real return on investment shows up in longer-lasting gains such as clearer thinking, personal growth, and greater resilience. This makes them powerful tools for leaders operating in complex environments.
Below are a few takeaways when considering an executive retreat including: how participants can become some of your best friends, introducing you to new ideas and concepts as well as how retreats help you take action and strengthen a part of your brain called “the willpower muscle.”
A Social Media Algorithm IRL
In an era where algorithms shape what we read, watch, and believe, executive retreats offer something increasingly rare: a human algorithm designed for growth. The people you meet at retreats introduce you to new programs, ideas, books, music, leadership frameworks, and ways of thinking, but without the advertisements or agendas. Instead of being fed what reinforces who you already are, you are exposed to perspectives that gently, and sometimes uncomfortably, stretch who you might become.
Most leaders seek out retreats based on interests they already have, which immediately creates common ground. Whether it’s leadership development, wellness, strategy, or personal growth, you arrive knowing that everyone in the room has chosen to invest time, money, and attention into becoming better at something that matters. This shared intention accelerates trust.
Retreat Friends Can Be Some of Your Best Friends
What makes retreat connections particularly powerful, however, is not the similarities, but the differences. Retreat participants often come from outside your industry, geography, or social circle. They are people you would not naturally encounter in your day-to-day routine. That distance from familiarity creates space for impact. These individuals can influence not just what you think, but how you think and feel about your everyday life. Their questions land differently, their observations bypass internal defenses and their stories linger.
Over time, retreat friends often become some of your most meaningful relationships. They occupy a unique category, separate from family, colleagues, and long-time friends. There is little overlap, which creates a rare psychological safety. They can offer a clean perspective during moments of career inflection because they don’t know your boss, your board, your team or your history. It can be easier to share ambitions, doubts, and fears with people who hold no preconceived narrative about who you are supposed to be.
For executives, this matters because leadership can be isolating. The higher you rise, the fewer places exist where you can speak openly without consequence. Retreat relationships provide a neutral ground and one where insight is not filtered through politics or expectations. In those conversations, clarity often emerges not because someone gives advice, but because they listen without agenda.
Nothing Changes If Nothing Changes
Beyond relationships, retreats catalyze change in a more fundamental way. Awareness alone does not transform behavior. As comedian Theo Von succinctly put it, “Nothing changes if nothing changes.” Many leaders already know what they want to improve whether that be better health, stronger presence, clearer priorities or more balance. The challenge is not knowledge; it’s execution. Retreats create a structured interruption to routine that makes execution possible.
By removing leaders from their habitual environments, retreats disrupt autopilot thinking. They introduce friction, reflection, and intentional practice. Whether through guided discussion, physical challenge, or skill-building exercises, participants are asked to do something different and that is where growth takes place. Retreats provide a container where discomfort can feel purposeful rather than punishing, and experimentation can feel safe rather than risky.
Importantly, effective retreats do not exist in isolation from real life. The goal is not escape, but integration. The most impactful retreats help leaders translate insight into daily practice; how to bring a new habit, mindset, or leadership behavior back into boardrooms, meetings, and home life. Change becomes tangible when leaders leave with both inspiration and a practical path forward.
The Willpower Muscle
There is also a neurological dimension to this process. Addressing hard things quite literally grows the brain. Research points to the Anterior Mid-Cingulate Cortex, also known as the “willpower muscle,” as a key region involved in resilience, effort, and decision-making. This area increases in size when people engage in productive struggle, such as intense physical exercise or learning new skills. In other words, leaning into difficulty enhances cognitive agility.
Executive retreats often create precisely this kind of productive struggle. They ask leaders to confront limiting beliefs, test physical or mental endurance, and practice unfamiliar ways of thinking. The result is not just emotional insight, but biological reinforcement. Leaders who repeatedly choose to challenge themselves strengthen the neural pathways associated with persistence and adaptability, which are two traits essential in complex, fast-changing environments.
Choose Challenge Over Comfort
The value of executive retreats is not necessarily found in luxury locations or curated schedules. It is in the connecting of people, perspective, and purposeful discomfort. Retreats act as a living algorithm, introducing leaders to ideas and individuals they didn’t know they needed, accelerating self-awareness, and making change unavoidable.
For leaders committed to growth, retreats are not a break from real work. They are the work. They sharpen the mind, expand the network, and create the conditions where meaningful transformation can occur. In a world optimized for convenience, choosing a challenge and choosing people who challenge you, may be the most strategic decision of all.
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Nancy Stern: Managing Director and General Counsel, Simplex Trading
People, Voices of ExperienceBy Jessica Darmoni
“The (trading) industry is built on people working together,” explains Nancy Stern. “You have to think of your interactions as long-term relationships. Something that makes sense in the short term may not serve you—or others—over time. You always have to ask: what are the unintended consequences?”
That long-term view has shaped Stern’s approach at career inflection points, business strategies and regulatory guidance. After first speaking with Stern over 10 years ago, The Glass Hammer sat down with her to talk about where she is now.
Today, as Managing Director and General Counsel of Simplex Trading, Stern stands at the intersection of market structure, regulation, technology, and leadership. She is the first, and only, lawyer at the 20-year-old market-making firm, a role that requires both precision and perspective.
Building Legal Infrastructure in a High-Speed Market
Simplex Trading operates as a market maker in the fast-moving world of equity options, where milliseconds matter and volumes have exploded. They continuously buy and sell options to capture the bid-ask spread. The firm is connected to 17 exchanges and has traders on the trading floor at Cboe Global Markets.
Over the past decade, the equity options market has transformed dramatically. Retail participation has surged. Trading volumes have exploded. Zero-day-to-expiration (0DTE) options have compressed time horizons to a single day—sometimes blurring the line between investment and entertainment for retail traders. In this environment, risk evolves quickly.
“We are in the business of taking risks,” Stern says. “My job is evaluating those risks. You have to understand the full picture—but most importantly, you have to adapt.”
Simplex historically relied on outside counsel. As the business grew more sophisticated, leadership recognized the need for an in-house legal leader to manage risk proactively, implement processes, and help shape culture from within.
Stern stepped into that role not only to mitigate legal exposure, but to build systems that support sustainable growth.
Her mandate includes implementing new procedures, strengthening governance, and aligning culture with regulatory expectations, all while keeping pace with accelerating technological change, including the integration of AI tools that are reshaping industries at unprecedented speed.
“The pace of change continues to accelerate,” she notes. “The tools are new but in many ways, the challenges are iterations of what we’ve faced before. That’s what makes it exciting to put these new tools into practice.”
From General Counsel to CEO, and Back Again
The Glass Hammer first met Stern in 2015 as Executive Vice President, General Counsel and Secretary of Allston Trading. She went on to become CEO of the proprietary trading firm, which was then acquired by DV Trading in December 2021. After the acquisition she joined futures commission merchant and clearing firm, ABN Amro, as Chief of Staff and General Counsel until 2024.
Her earlier career includes partner roles at Katten Muchin Rosenman LLP and Gardner Carton & Douglas LLP (now Faegre Drinker Biddle & Reath LLP), where she built the legal foundation that would later support her executive leadership.
Transitioning from General Counsel to CEO required more than technical skill, it required self-awareness.
“Coaching was very important to me,” Stern reflects. As she prepared to step into the CEO role, she worked with an executive coach and encouraged her team to do the same. “Understanding your strengths and weaknesses is essential. Sometimes you need someone outside your organization to help you think clearly.”
That investment in self-knowledge became a catalyst for growth.
Resilience, Realism, and Knowing When to Walk Away
Leadership, especially in high-stakes financial environments, inevitably includes moments of doubt. Stern approaches setbacks with a problem-solver’s mindset, and with realism.
“You have to ask yourself: Is this a situation I can improve? Or should I walk away? Can I make this better, or would someone else do a better job?”
She describes herself as loyal and deeply committed however she also recognizes limits. Not every system can be fixed from within and not every environment is the right one.
For women navigating leadership roles, that distinction is powerful: resilience does not mean staying at all costs. It means making thoughtful, courageous decisions about where you can create impact.
Mentorship in All Directions
When asked who influenced her most, Stern doesn’t name a single figure.
“I’ve been fortunate to have mentors at every stage and from all directions,” she says. “Senior people, junior people, peers.”
She learned the craft of law from colleagues in law firms. She learned how to lead organizations by listening to those who understood the pulse of the business and the pain points of its people.
What does she value most?
“Anyone willing to speak the truth, even when it’s difficult.”
Now, she pays that forward. Mentorship is one of the impacts she most hopes to create.
“There are people with tremendous talent who just need guidance on specific questions. If I can help them move forward, that’s incredibly satisfying.”
What the Future Demands from Leaders
As markets evolve, so must leadership. Stern believes future leaders will need empathy and the ability to put others first.
“Strong listening skills, sound judgement and the ability to sift through vast information to make principled decisions will be demanded of our leaders,” she emphasizes.
Stern also believes that execution, the discipline to turn vision into reality will be crucial.
“Vision without execution doesn’t count,” she says.
In an era of accelerating AI adoption, shrinking time horizons, and increasingly complex market participation, those human-centered skills may matter more than ever.
Leading Into the Future
What inspires her now?
“New tools. New experiences. New ways to approach old challenges.”
Despite decades of experience across law firms, trading floors, executive suites, and boardrooms, Stern remains energized by evolution.
Her leadership is not about chasing speed but about thoughtful adaptation, long-term relationships as well as clear-eyed risk assessment and helping others grow along the way.
In industries often defined by volatility, Stern’s career is a reminder that sustainable leadership is built not only on expertise, but on empathy, integrity, and the courage to continually adapt.