Tasha Dickinson, Partner, Day Pitney

In an interview with Invest:, Tasha Dickinson, partner at Day Pitney LLP, discussed the firm’s strategic growth, the ongoing population boom in South Florida, and how evolving client needs are shaping legal services. “Day Pitney has been part of this market for a long time. We’re not new here, and that longevity is a key differentiator. We open offices where our clients need us,” she said.

What has most impacted Day Pitney’s West Palm Beach office over the past year?
The significant influx of people moving into Palm Beach County, along with anticipated tax law changes, has kept the firm extremely busy, particularly in the Private Client department.
This migration has also spurred demand across our real estate, corporate, and litigation practices. While I focus on trusts and estates, the growing population has increased legal needs firmwide — ultimately a positive development.

How does the work in Palm Beach compare with other Day Pitney markets?
In Palm Beach and South Florida, there’s a strong focus on private client work due to the area’s wealth and steady influx of new residents.
Day Pitney is particularly active in trusts and estates and the family office space, which intersects with corporate and real estate services. In contrast, our Washington, D.C., office concentrates more on energy law. In Connecticut, our attorneys focus heavily on insurance law, reflecting the state’s long-standing role as a hub for the insurance industry.

What issues are clients facing, and where are the strongest growth opportunities?
The sheer number of people now living in the area has caused some personal frustration for long-term residents. Things like restaurants, dry cleaning, gyms, and tennis courts are all the more crowded. The community is still catching up to the rapid population growth, and that’s created a strain on local resources.
In terms of growth opportunities, the biggest needs, and therefore the areas with potential, are infrastructure, healthcare, education, and workforce housing. Property values have risen so dramatically that it’s difficult for some to afford to live in the area. That creates a challenge because communities rely on a full workforce to function and grow.
We see opportunity in developing projects that expand infrastructure and build out the community to meet current demands.

What separates Day Pitney from other law firms in South Florida?
Day Pitney has been part of this market for a long time. We’re not new here, and that longevity is a key differentiator. Many firms are just now opening offices in Palm Beach County, trying to capitalize on the population growth. Day Pitney, however, already has a well-established name in the South Florida legal community.
Our size also sets us apart. We’re not a mega firm — we’re a midsize firm with more than 300 attorneys. That gives us the resources our clients need without the bureaucracy that often comes with a large international firm. We can be more efficient and responsive, which clients really value.
Another distinction is that many of our attorneys are from Florida. They grew up here and are deeply embedded in the community. That local knowledge matters. Other firms may be staffing their South Florida offices with attorneys relocated from New York or D.C., who may not fully understand the local market. Day Pitney has built relationships and trust here over many years.

To what extent is Day Pitney benefiting from business relocations, expansions, and population growth?
We’ve benefited significantly from the influx of people, especially within the Private Client department. I focus on domicile planning, so I work closely with clients migrating to Florida for tax reasons. Many are seeking relief from what they view as oppressive tax regimes in their home states, and Florida offers a more favorable environment.
But the growth isn’t limited to private client work. Real estate has been extremely active — people are buying properties, securing office space, and investing in developments. A common pattern we’ve seen is someone buys a seasonal condo, decides they like Florida, and then upgrades to a permanent home. That has driven a lot of real estate activity.
Businesses are also relocating to Florida. It’s no longer just individuals retiring and moving here. We’re now seeing entire business operations relocate, which has led to a substantial increase in corporate work. Our Family Office group has also been very busy as more family offices are being moved into the state.
And of course, with increased population and business activity comes more litigation. Disputes are a natural byproduct of transactions and growth, so we’ve seen a rise in litigation work as well.

What are some common legal mistakes clients make and why is seeking legal advice important?
The two biggest mistakes I see are doing nothing and failing to communicate.
Doing nothing often stems from clients thinking they don’t need legal advice, either because they believe they already know what to do or they’re simply hesitant to seek help. But failing to act can lead to costly issues down the road.
The second mistake is poor communication. In the private client world, that can mean not clearly communicating goals or facts. I always tell clients I’m only as good as the information I receive — if the input is flawed, the outcome will be too. Lack of communication within families is another common issue, and it often leads to litigation.

What is Day Pitney’s current approach to growth and expansion?
We are definitely in growth mode. We want to bring in more attorneys to strengthen the areas where we already practice here in South Florida, and we’re open to expanding into additional practice areas where there’s demand.
In terms of new offices, we’re very strategic. Unlike some firms that open offices just to have a presence, we open offices where our clients need us. So, while we’re open to expansion, it has to make sense from a client service perspective.

What are your biggest current challenges, and how do they reflect broader legal industry trends?
Hiring qualified candidates in this market is probably our biggest challenge — and that’s not unique to Day Pitney or even to the legal industry. It’s a widespread issue right now.
Even though it feels like COVID happened a long time ago, firms are still adjusting to post-pandemic operations. One example is the hybrid work model. We currently have attorneys in the office three days a week and working remotely two days. Whether that’s the best long-term approach is still being evaluated. Many firms are navigating similar questions and dealing with the lasting effects of the pandemic.

Are there any regulatory frameworks or legislative developments you’re closely monitoring?
While not regulatory in nature, we’re closely watching developments in Congress related to tax law. A significant change is currently set to take effect on Jan. 1, 2026, and if that happens, it will dramatically impact how I advise my clients.
When the new administration took office, there was an expectation of a temporary reprieve from major tax changes. That gave many people a sense of comfort. Now, it’s much less clear whether that reprieve will happen. As a result, there’s growing concern among trust and estates attorneys that a major shift in tax law could indeed occur, and if it does, the rest of 2025 will be extremely busy for us.

How is Day Pitney leveraging technology, including AI, to advance the firm’s goals?
We have an AI committee that is actively studying what AI can and cannot do within the context of a law firm. At Day Pitney, confidentiality and the protection of client data are of the utmost importance. As a result, the firm exercises heightened caution in adopting artificial intelligence technologies, maintaining stricter standards than many other industries to safeguard sensitive information and client trust.The integrity of our client information is paramount.
That said, we recognize that AI can offer efficiency benefits in certain areas. For example, it can assist with specific types of research, though this impacts the litigation side more than my own practice. We do have policies in place that restrict how AI can be used, and we don’t rely solely on it for substantive work.
Overall, it’s a work in progress. We’re open to the possibilities AI brings, but we are moving forward cautiously. It’s a powerful tool, but also a potentially risky one.

What is your outlook for Day Pitney and the legal sector in Palm Beach over the next two to three years?
I believe we’ll continue to see the same trends we’ve been experiencing, even though the broader market has softened somewhat. While South Florida hasn’t been completely immune to that, it hasn’t been hit as hard as other regions.
This area is still booming. People are continuing to move to Florida, and with that comes a steady demand for legal services. The momentum we’ve seen over the past five or more years doesn’t appear to be slowing down.
Our Latin America practice has seen significant growth. That complements our private client and family office work and reflects not just migration from within the United States, but also a rising influx of clients from Latin American countries.
We’re part of several global networks that support this work, and we’ve been doing a great deal in that sector. It’s become an important area of expansion for the firm.