About Us

Who We Are

Black Sail is a leadership advisory firm
focused exclusively on serving law firm
leaders.

Who you are

Our Mission

Our mission is to enable law firm owners to reclaim their time, enhance profitability and drive sustainable success through transformational advice.

Origins

Our Name Embodies Our Resolve

Black Sail draws its name from the legendary black sail of Achilles' ship, leading the way to Troy. This iconic image symbolizes determination, leadership, and fearlessness to venture into uncharted territories. Just as Achilles' black sail represented a formidable and decisive mission, Black Sail embodies the resolve and expertise required to lead law firms through transformative change.

At Black Sail, we are dedicated to helping you become the visionary leader you aspire to be, transforming your law firm into a thriving enterprise.

Our Founder

Tom Choberka

Principal Advisor

Jason Vanslette,
Attorney, Chair of Real Estate Division

“Tom’s progressive ideas along with his ability to master the human condition has contributed immensely to my career successes and expanding my client base both privately and institutionally."

Tom Mersch, Attorney, General Counsel

Tom’s knowledge and skills in marketing and business development have added value in every situation in which I have witnessed him participate. Tom possesses a high level of emotional intelligence and strategic thinking.”

Our Core Principles

We lead with generosity.

We have an “abundance mindset” and believe that helping others succeed is the greatest reward.

It means something.

Being our client, our partner or our friend, means something.
‍
All our work is focused on meaningful relationships, goals and transformative outcomes.

We believe the right questions provide the pathway to solving the toughest problems.

We uncover the underlying cause of the issue instead of just treating the symptoms.
‍
We listen deeply so we can offer unparalleled insight.
‍
We don’t offer advice until we have a deep understanding of the core drivers and challenges our clients are facing.

Objective advice is the only advice we offer.

Our advice comes without influence and is based on reaching agreed upon desired outcomes.
‍
We have zero conflicts of interest.

An elevated client experience.

We treat people and communicate with them the same way we want to be treated.

Excellence in every action, interaction and engagement.

How we do anything is how we do everything.

Our standards are elevated because high-performing people do not tolerate mediocrity.

We focus on prioritization and then progress.

Outside forces will shift a business’s priorities. We help you re-evaluate your priorities and re-focus your attention and resources.

We move faster.

We appreciate that time is our only non-renewable resource.

We move with urgency on matters that generate progress and accelerate outcomes.

We move quickly to eliminate biased, antiquated thinking and re-establish a culture of progress.

We embrace technology as the foundation that today’s businesses are built on.

We focus on user adoption and usability to create the most impact.

Outcomes over time.

We don’t bill for time; we share in the value of producing outcomes.

Mastery of fundamentals takes precedence over innovation.

When ready, we innovate to shorten the timeline of our desired outcomes.

Our confidence is born through our preparation.

We prepare until confidence appears, regardless of how long it takes.

The right answer is not always the best answer.

We are hyper-aware of the complexity of our clients’ problems and offer nuanced, tailor-made advice that considers the impact of game-time decisions.

A great idea without execution is worthless.

We don’t offer ideas without the blueprint, guidance, and support of how to execute them.

Black Sail offers a range of advisory service designed to address

The most pressing business needs of law firm leaders:

People, Personalities and Roles

We use science based personal assessments to share a deep understanding of your current team and utilize the same science for potential new hires and key roles within your firm. Our proprietary methodology helps you solve the “who” problem in your organization.

Business Development Strategy

Lead services and random event attendance are not the solution. Enhance your firm’s revenue and profitability through a real business development strategy that starts with your firm’s positioning.

Marketing Strategy

Stop wasting money on marketing with no cohesive strategy. Stop random acts of marketing. Optimize your marketing spend and improve overall effectiveness with strategic insights and unbiased recommendations.

Leadership Advisory

Get off the hamster wheel and become the leader you always envisioned you would become. Forget hype conferences and group therapy sessions. Get one-on-one leadership advice from a seasoned law firm executive.

Operational Excellence

Everybody knows they need to do this, almost nobody does it. Document, streamline and improve your firm’s systems and processes to maximize efficiency and productivity.