Why Lawyers Are Natural Challenger Sellers :: The Difference Between Service and Leadership

By Jane Southren

The legal profession has traditionally emphasized relationship-building and technical expertise, but what truly distinguishes exceptional lawyers in today's competitive landscape? From my experience, the most successful professionals across industries aren't those who focus primarily on relationships or hard work – they're the ones who challenge their clients' thinking and guide them toward better decisions.

Lawyers face a critical choice: remain in the comfortable role of service provider or step up as a strategic advisor who shapes client outcomes. The "Challenger" approach, originally identified in sales research, offers a powerful framework for lawyers seeking to deliver unprecedented value.

The Five Lawyer Profiles: Where Do You Stand?

Sales research from the Harvard Business Review has identified five distinct professional profiles. Each offer a striking parallel to how lawyers approach client relationships:

Relationship Builders (Lowest Performers)

The approach: These lawyers prioritize harmony above all else, avoiding difficult conversations and focusing on being liked.

Real-world example: When a client proposes a risky business strategy with serious legal implications, the Relationship Builder nods along and finds ways to implement the plan despite foreseeing problems, fearing that pushback might damage the relationship.

The limitation: While clients may enjoy working with these lawyers, they often don't receive the challenging guidance needed to make optimal decisions. Your clients don't need another yes-person – they need someone who'll tell them what they’re missing.

Reactive Problem Solvers

The approach: These lawyers excel at addressing issues as they arise, delivering reliable solutions to immediate problems.

Real-world example: When a client faces a contract dispute, the Reactive Problem Solver efficiently resolves the specific issue but fails to identify and address the underlying contract management system that caused the problem in the first place.

The limitation: While competent at putting out fires, these lawyers rarely help clients prevent them. According to a survey of Fortune 500 general counsel, 78% value proactive advice over reactive solutions.

Hard Workers

The approach: These lawyers pride themselves on effort, billing long hours and responding quickly to every client request.

Real-world example: A Hard Worker lawyer stays up all night perfecting a 50-page memo that answers every conceivable legal question related to a transaction, but fails to provide the concise, actionable guidance the client actually needs to move forward.

The limitation: Effort without strategic direction often creates more work than value. Clients increasingly report valuing efficiency and insight over sheer effort.

Lone Wolves

The approach: These independent-minded lawyers rely on their natural confidence and instincts, often breaking conventional processes.

Real-world example: A Lone Wolf might develop a brilliant legal strategy but fail to collaborate effectively with their client's internal team, creating friction that ultimately undermines implementation.

The limitation: Today's complex legal challenges require collaborative approaches. Technical brilliance means nothing if you can't work with your client’s team.

Challengers (Highest Performers)

The approach: These lawyers bring fresh perspectives, aren't afraid to push back on client assumptions, and take control of conversations to guide clients toward better outcomes.

Real-world example: Let’s say a technology client wants to quickly launch a new product. A Challenger lawyer would not only identify regulatory risks, but they’d present three alternative launch strategies that balance innovation with compliance. Ultimately, this protects the client from costly regulatory action.

The advantage: Challengers build deeper trust by demonstrating they value the client's long-term success over short-term comfort. In my coaching work with lawyers who've adopted this approach, client retention rates have increased significantly.

Why Lawyers Are Natural Challengers

The characteristics that define successful Challengers align perfectly with the best traditions of lawyering:

They Educate and Lead. Great lawyers don't just apply the law – they help clients understand it in the context of their business objectives. A Challenger-minded lawyer working with a healthcare client wouldn’t simply outline HIPAA requirements; they’d create a decision framework designed to help executives evaluate innovation opportunities against compliance considerations. As a result, the client would be empowered to make better decisions independently.

They Build Relationships Based on Trust, Not Harmony. If a client was considering an acquisition that carried significant antitrust risk, a Challenger lawyer would present a detailed analysis of the likely regulatory response. Though the client might initially resist this assessment, they would likely credit the lawyer down the road for saving them from a disastrous deal. Sometimes the pushback can be frustrating for clients, but ultimately the benefits of honest guidance become apparent.

They Take Control of the Conversation. Rather than passively responding to client inquiries, Challenger lawyers guide discussions toward critical issues clients might not recognize. A major transaction is daunting, but what if you presented a client with a risk assessment framework that could transform meetings in such a way that it changes the way your clients think about large transactions.

They Think Ahead and Anticipate Problems. A Challenger-minded employment lawyer always seeks to identify risks before they become problems.

They Add Strategic Value. Beyond technical legal advice, Challengers integrate business context into their guidance. For example, a real estate lawyer serving a restaurant chain doesn't just close deals – they analyze location data and recommend expansion priorities based on regulatory environments and market opportunities. Doing so, they become an invaluable part of the client's growth strategy.

Becoming a Challenger :: Practical Steps

Transitioning to the Challenger approach requires intentional skill development:

Deepen your commercial awareness: Invest time understanding your clients' industries beyond legal considerations. Read their trade publications, follow their competitors, and understand their business metrics.
Develop a point of view: For each client matter, formulate a clear perspective on the optimal approach, not just the legally defensible options.
Master strategic questioning: Replace "What do you want to do?" with questions that challenge assumptions: "What if we approached this from a different angle?"
Practice constructive tension: Become comfortable creating and resolving productive disagreement. Role-play difficult conversations before having them, if you’re nervous.
Create teaching moments: Develop frameworks and tools that help clients see issues in new ways, elevating discussions from tactical to strategic.

Overcoming Resistance

Some lawyers worry that challenging clients might damage relationships. However, my experience has shown the opposite effect. When delivered with genuine concern for the client's success, challenging guidance deepens trust rather than eroding it.

There is one key point of distinction to bear in mind. Challengers don't oppose client objectives; they elevate them by introducing new perspectives and approaches that clients hadn't considered. They don't say "no" – they say, "here's a better way."

From Service Provider to Strategic Advisor

The legal profession stands at a crossroads. As AI increasingly handles routine tasks and clients face increasingly complex challenges, the value of a lawyer lies not in technical knowledge alone but in their ability to guide clients through uncertainty with confidence and insight.

By embracing the Challenger approach, you can transform your client relationships from transactional to transformational. You will become not just a legal advisor but a strategic partner in your clients' success.

So, the question isn't whether you can afford to become a Challenger – it’s whether you can afford not to.