Brokerage Roundtable: What Veterans Can Learn From Fresh Talent

October 7, 2025

Brokerage Executive Insights Featured National

Young brokers are proving that innovation and experience work best in tandem. Here's why mutual learning is key for long-term success.

Four headshots edited featuring Allie McCracken, Tobias Hipp, Benjamin Bouganim and Lexi Castellino — From left to right, top to bottom: Allie McCracken, Tobias Hipp, Benjamin Bouganim, Lexi Castellino. *Images courtesy of Transwestern, Kidder Mathews, Cushman & Wakefield and JLL, respectively*

Seasoned brokers often share their knowledge with those just beginning to forge their career paths. But knowledge transfer can go both ways, and when generations learn from each other, the industry grows stronger, creating space for innovation and collaboration.

Young brokers may have fewer years in the field, but they bring a different kind of expertise to the table. Quick to adapt and comfortable with the latest technological advancements, they help integrate digital fluency into daily operations, bridging traditional practices with modern workflows.

To explore how they’re adding value to senior teams, we talked with young professionals from top real estate brokerage companies, including JLL Associate Lexi Castellino, Cushman & Wakefield Senior Associate Benjamin Bouganim, Transwestern Vice President Allie McCracken and Kidder Mathews Senior Associate Tobias Hipp.

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What do you think are your strengths? Are there any technologies or skills that you master that your senior colleagues might not?

Bouganim: Coming into the business, I leaned heavily on digital research tools, data aggregation platforms, and social media to build relationships and uncover opportunities. Many senior brokers are experts at cultivating business face-to-face, and I’ve tried to complement that with a stronger online presence and use of tech to accelerate research, streamline prospecting, and position myself and my team as thought leaders. For me, platforms like LinkedIn and real-time market data sources have been instrumental in expanding my reach.

At Cushman & Wakefield, that blend of traditional expertise with newer digital strategies has allowed us to deliver more value to clients and stay ahead of how the industry is evolving.

Castellino: Since graduating, I’ve incorporated ChatGPT into my routine, and for tasks like market research, content creation and data analysis, I use JLL GPT, JLL’s proprietary AI assistant developed by our JLL Technologies team. I’ve found that my comfort with these newer technologies often helps me work more efficiently and could help bridge any potential digital gaps in the team.

I’m fortunate to be part of a team that prioritizes staying ahead of new technology. We’ve made it a point to stay curious and forward-thinking, keeping pace not only with today’s evolving trends but also with those to come.
—Allie McCracken, Vice President, Transwestern

Seasoned professionals often guide and mentor rising brokers—but what about the reverse? What fresh perspective or skill have you brought to your team that’s proven valuable?

Hipp: What I brought was eagerness to hit the market. Not knowing everything at first helped because it gave my mentor the chance to guide me toward what he knows it takes to be a great broker. I brought the energy—kicking in doors, hammering the phones, trying to source deals from nothing—and he helped me channel it into the right places. That combination pushed my professional development forward and showed us what we can accomplish together.

McCracken: No matter the level of experience, everyone can benefit from different perspectives. I’ve been encouraged to contribute ideas to pitches and projects just as any other member of the team would. This mutual appreciation for the diversity of thought fosters internal growth and ultimately leads to well-rounded solutions for our clients.

For Lexi Castellino, becoming a resource when it comes to using AI turned into an opportunity to add value to her team. Image courtesy of JLL

Castellino: It’s starting to get more common, especially when it comes to new technology/AI. I tend to find myself being a resource when it comes to using platforms like JLL GPT. My ability to turn things around quickly using AI has created immense value for my team, and it’s been an incredible opportunity to be able to share that knowledge back with others.

Bouganim: I’ve tried to bring a fresh perspective on branding and storytelling—whether that’s through creating concise client-facing materials or leveraging digital channels to share insights. My mentors have decades of experience and deep institutional knowledge, and I’ve been able to complement that by helping present it in ways that resonate with today’s decision-makers, particularly newer or international entrants to the New York City market.

Have you ever felt any resistance? What are the usual reactions you get when sharing a new approach with the rest of the team?

Hipp: I’ve been lucky to have one of the best mentors in the business. He tells me when I’m wrong and also reinforces when I’m taking the right approach. I wouldn’t call it resistance—if anything, it’s accountability. Whether it’s a meeting I’ve been chasing for weeks or knocking on doors unannounced, he’s ready to help secure the client, push the deal forward or close it so we can get paid.

When you’re young in this business, there’s always the challenge of proving yourself. But I’ve found that hard work, consistency and a willingness to learn from those ahead of me break down those barriers.
—Benjamin Bouganim, Senior Associate, Cushman & Wakefield

McCracken: I haven’t experienced resistance—only opportunities to expand my own mindset. Like many young professionals, I’ve faced moments of ‘imposter syndrome.’ My team’s response has been to encourage me to use my voice, knowing it benefits our collective growth. Removing the self-imposed restraints around speaking up has allowed me to grow as a professional and support my goal of continued development.

Was there a moment when your fresh perspective helped change a strategy or approach that felt outdated?

For Benjamin Bouganim, mentorship has been the cornerstone of his growth. Image courtesy of Cushman & Wakefield

Bouganim: One area has been client engagement. While phone calls and in-person meetings are still the foundation of our business, I’ve expanded how we connect by using LinkedIn, targeted email campaigns and digital updates. I’ve also started implementing AI to spot patterns in the market and flag areas where clients might have risks or opportunities they hadn’t thought about. We’re adding another layer of insight that helps us show up with more thoughtful, tailored advice.

McCracken: Many of the approaches that have been around for a long time remain in place because they work. In today’s environment, where new tools and techniques emerge at a rapid pace, our team focuses on finding ways to bring fresh perspectives to these tried-and-true processes while also incorporating new techniques that benefit our clients.

Hipp: New energy and perspective can always add value when you’re looking at strategy. I wouldn’t say I changed ours, but it’s improved as we’ve worked together. BOVs became sharper, valuations told a stronger story, and that helped win new business. We didn’t replace the process—we streamlined it to get better results.

Every generation reshapes workplace values. Today is about inclusivity, digital fluency, mental health and creativity. Have you seen these priorities reflected in your team’s culture?

Bouganim: Yes, absolutely. The industry has always been competitive, but I’ve noticed a greater emphasis on collaboration, inclusivity and work-life balance, particularly as new talent enters the field. Mental health, flexibility and authenticity are topics that now get more attention, and it’s clear that teams perform better when those values are embraced. That shift has made it easier for me to feel comfortable contributing ideas early on.

Whenever dealing with moments of “imposter syndrome,” Allie McCraken’s colleagues encourage her to use her voice and expand her mindset. Image courtesy of Transwestern

McCracken: Luckily, I’m part of an organization that recognizes that one size does not fit all and embraces evolving workplace dynamics. For example, digital fluency has become a key driver of efficiency and effective communication, both internally and with our clients. The long-term benefits include greater opportunities for synergy and the ability to build lasting partnerships.

Hipp: I was told coming in that this business is long hours, a lot of rejection and often a lonely grind. In a business where you eat what you kill, inclusivity doesn’t always show up the way it does in other industries. Where I’ve seen change is in digital fluency—being efficient with tech lets me pack more into the day. As for mental health, you’ve got to be tough and resilient if you want to make it. If you’re not mentally sound, you won’t last. Creative expression I leave to the pros, and our Kidder Mathews marketing team puts out material that’s above anything else in the market.

How do you view mentorship? Do you find it more valuable when it’s based on mutual learning?

Tobias Hipp’s energy and fresh perspective helped streamline processes to get better results. Image courtesy of Kidder Mathews

Hipp: I think mentorship is at its best when it goes both ways. My mentor always told me ‘Ask me anything at any time, and I’ll give you the answer, plus 20 other things you didn’t even think to ask.’ That kind of openness helped me pick things up quickly, but it also gave him the chance to see the business through a fresh set of eyes. When there’s trust and respect on both sides, mutual learning happens naturally.

Castellino: I absolutely believe the best mentorship relationships are built on mutual learning. While I value gaining experience and wisdom from senior colleagues, I also think my fresh perspective and familiarity with new technologies can add value to the relationship.

Bouganim: I think mentorship is at its best when it’s reciprocal. Mentorship has been the cornerstone of my growth and I’ve been fortunate to learn from senior colleagues who have been incredibly generous with their time and knowledge. At the same time, I’ve been able to bring my perspective, whether it’s around technology, branding or new ways to connect with clients. That kind of two-way learning not only accelerates growth but also strengthens the team dynamic and ensures we’re continuously adapting to a changing market.

McCracken: Mentorship has played a pivotal role throughout my career. It has always shown to be a mutual exchange of information, ideas and experiences across all levels. At its core, mentorship is driven by continual curiosity, which is a hallmark of growth that builds knowledge, wisdom and, ultimately, success.