Empowering Compassionate Advocacy: How Jackwin Legal Transformed Their Practice with ActionCOACH

When attorneys Kristen and Eric Jackwin decided to launch their own law firm, they were already well-versed in criminal defense, real estate, and business law. Yet, despite excelling in court and negotiations, they soon discovered that running a multi-faceted practice posed its own unique challenges. Hiring staff, building a team culture, and managing finances were not topics covered in law school. Undeterred, they took a calculated leap and founded Jackwin Legal, prioritizing “compassionate advocacy” to guide clients through everything from criminal charges to complex property deals. In parallel, they created Connect Esquire, a mastermind community helping fellow lawyers master the business side of legal practice. After partnering with ActionCOACH for greater clarity and accountability, the Jackwins’ journey became a testament to how strategic coaching and unwavering empathy can redefine a law firm’s success. 

FOUNDERS’ BACKGROUND & INITIAL CHALLENGES

Kristen’s introduction to criminal defense began with her father, a veteran attorney whose passion for helping “the little guy” inspired her early on. “He always taught me to see clients as humans first,” she recalls. In law school, she initially slogged through classes like Property and Civil Procedure until she discovered a genuine spark in Evidence and Criminal Procedure. Working alongside her father provided comfort and a steady income, but after nearly a decade, she felt called to build a different legacy—one she could shape with her husband, Eric. 

Eric, meanwhile, carved out his own reputation handling real estate transactions and estate planning. He approached problems methodically, thriving on well-documented systems and step-by-step processes. When he and Kristen decided to merge their skills under one firm, optimism ran high. They agreed they were “real entrepreneurs,” as Kristen put it, with multiple ventures in mind. Yet they soon discovered that leaving the safety net of Kristen’s father’s established practice presented more hurdles than they had anticipated. 

RECOGNIZING THE NEED FOR COACHING

Despite their legal expertise, the Jackwins quickly encountered roadblocks in three key areas: 

• Team Building: Hiring staff with the right legal skills was one thing, but ensuring they aligned with the firm’s values was another. “We don’t just need skilled lawyers,” Kristen explains. “We need people who truly care about the well-being of our clients.” 

• Business Acumen: Law school didn’t teach them how to run a business. “You don’t learn how to build an empire in law school,” Kristen says. “You learn how to interpret the law, not how to manage finances or lead a team.” 

• Fear and Transition: Leaving an established practice meant stepping into uncertainty. Kristen admits, “Sometimes I miss the security, but there’s nothing like working side by side with Eric, building something that’s truly ours.” 

As their firm grew, the Jackwins realized they needed help streamlining their operations, improving financial tracking, and creating a sustainable hiring process. They turned to ActionCOACH and began working with Coach Michael Dill in 2019. 

IMPLEMENTING THE ACTIONCOACH APPROACH

“ActionCOACH was that bridge between the vision we had and the operational structure we lacked,” Kristen recalls. “They guided us, step by step, on how to run the firm like a true business while keeping our integrity and empathy front and center.” 

With Coach Dill’s guidance, the Jackwins began by clarifying their core mission: “compassionate advocacy.” They recognized that authenticity in serving clients required a robust internal framework, including job roles, onboarding protocols, and measurable performance standards. As they built out these structures, they leaned on key ActionCOACH principles: 

• “Who Not How:” Inspired by the Dan Sullivan concept that tasks should be delegated to the best-suited person, not always done by the founder. They reworked their hiring process, instituting multiple interviews to screen for both competence and empathy. Kristen jokes that they used to ask, “Can you draft this motion?” but now they also probe, “How do you show compassion to a client in crisis?” 

• Goal Setting & Accountability: Through weekly check-ins and structured exercises, the Jackwins learned to set SMART goals for areas such as revenue, team size, and marketing reach. They began tracking their finances meticulously, a shift from Kristen’s earlier approach of “I bring in money and watch it go out. Now I want to see where it goes.” 

• Personal Development: Drawing from books like The Culture Code, 10x Is Easier Than 2x, and even The Success Principles, they refined their leadership style. Kristen especially credits these readings—and conversations with Coach Dill—with helping her move away from an “old school” mindset. “I saw how yelling or micromanaging was just me venting. That wasn’t leadership,” she admits. 

As a result, the firm moved from sporadic intake processes and random financial oversight to a cohesive system of lead tracking, staff performance evaluations, and client feedback loops. “We learned that if we’re going to deliver top-tier legal representation, we need top-tier structures behind the scenes,” Eric says. 

ACHIEVING RESULTS & KEY WINS

Steady, incremental improvements led to a series of tangible wins. The first milestone was team revitalization. By focusing on genuine cultural alignment—people who, in Kristen’s words, “truly care about the client’s well-being”—they finally built a roster they could trust. This team reflected the Jackwins’ emphasis on what they call “compassionate advocacy,” delivering thorough hand-holding in emotionally charged criminal cases while still bringing “firepower” to the courtroom. 

Recognition soon followed. Both Kristen and Eric were honored as Super Lawyers Rising Stars, an achievement they attribute partly to the renewed focus on professional growth. “It’s not just about listing your credentials,” Eric says. “It’s about having a consistent track record of great client outcomes and peer respect.” He notes that many fellow attorneys noticed the firm’s culture of empathy and began sending referrals their way, especially in criminal defense matters. 

Another key victory was the ability to diversify while maintaining quality. Eric further grew the real estate and estate planning side of the practice, establishing systematic checklists for every deal and will package. Kristen, in turn, refined her trial approach by using a “compassion meets preparation” philosophy. “There’s no such thing as an unimportant hearing,” she emphasizes. “We guide clients from arrest all the way to what we call ‘Criminal Justice Success.’” 

CLIENT VOICES & TESTIMONIALS

Throughout their journey with ActionCOACH, the Jackwins relied on pivotal moments of insight: 

Kristen on Leaving Her Father’s Firm: 
“I was helping build his empire, not my own. It was comfortable, but there’s nothing like creating a shared vision with Eric. That leap was scary—and absolutely worth it.” 

Eric on Personal Growth: 
“Reading books like Who Not How and 10x Is Easier Than 2x gave us the language to describe what we needed to change. Then ActionCOACH held us accountable. We could have read 100 books, but without that follow-through, nothing might have changed.” 

Kristen on Team Building: 
“We tried eight different hires before we finally got it right. Now, when I see a paralegal walking a client through a nerve-wracking court date like they’re family, I know that’s the culture we fought so hard for.” 

Eric on the ‘Magic’ of Alignment: 
“When both people in a marriage believe in growth, business, and service, it spills into everything—kitchen-table brainstorms become million-dollar ideas. We had to learn how to harness that for the firm and for Connect Esquire.” 

FUTURE GROWTH & VISION

The evolution of Connect Esquire has become one of the Jackwins’ most meaningful achievements. Initially a modest mastermind group, it now serves as a structured community where attorneys nationwide exchange best practices about hiring, marketing, and client care. “We realized so many lawyers feel isolated,” says Eric. “Law school never taught us how to run a business, so we built a network to fill that gap.” 

Ambitions for Connect Esquire include expanding its online presence, offering deeper mastermind tiers, and hosting live events that combine legal education with entrepreneurial insights. “Our big hairy audacious goal is to go national,” Kristen says. “We want attorneys everywhere to have access to a mastermind for lawyers by lawyers, so they can replicate what worked for us—minus the tears.” 

Meanwhile, Jackwin Legal continues to refine its internal processes, aiming to open more offices with the same ethic of compassionate advocacy. They see potential in other practice areas as well, especially if they find the right attorneys who share their client-focused mindset. “Ultimately, you don’t have to choose between empathy and success,” Kristen says. “We’ve shown you can do both with the right systems, the right people, and the right coach.” 

THE NEXT STEPS

Today, Jackwin Legal stands as a testament to the power of building a mission-driven law firm. By intertwining process-driven strategies with genuine empathy, Kristen and Eric have created a place where clients feel cared for and staff feel engaged. Their success extends beyond court victories, touching an entire community of attorneys through Connect Esquire. 

For those juggling big visions and daily operational headaches, the Jackwins’ journey provides a real-world blueprint. They demonstrate how strategic coaching can help integrate core values with financial viability, ensuring that growth does not undermine authenticity. “Whether you’re a lawyer, a doctor, or any professional, if you dream of entrepreneurship, you have to invest in yourself—and that includes a mentor who sees what you can’t,” Eric says. 

If you find yourself on the edge of a similar leap, reach out to book a discovery call today and begin your journey of newfound entrepreneurial success. As Kristen puts it, “We’d still be scratching our heads over payroll or marketing without coaching. Now we run our business with clarity, and that clarity lets us focus on what really matters—serving our clients and building an aligned future.”