Why the Best Rainmakers Listen More Than They Sell

By Steve Fretzin and Susan B. Silverman

Why lawyers do not need to become salespeople to develop business, and how listening, trust, self awareness, mentorship, and leadership can create a stronger path to partnership.

Law school teaches lawyers a lot of things. How to analyze complicated issues. How to research. How to write. How to advocate. How to think critically under pressure. What it generally does not teach is how to bring in clients, develop people, build relationships, or lead a team.

Then lawyers reach the middle of their careers and suddenly those skills become incredibly important.

In this episode of BE THAT LAWYER, I sat down with Susan B. Silverman, a former commercial litigator who now helps law firms retain and develop mid level associates, strengthen leadership pipelines, and build more effective systems for long term growth. Remarkably, this was Susan’s first podcast appearance, and we covered an issue that I see constantly in my coaching practice: lawyers are often expected to develop business and become leaders without ever being taught how to do either one.

Susan and I agree on another important point. Business development does not require lawyers to transform themselves into salespeople. In fact, some of the most effective business developers succeed because they listen carefully, ask good questions, build trust, and develop relationships in ways that feel authentic to them.

Stop Trying to Become the Rainmaker Down the Hall

One of the biggest mistakes lawyers make when they begin developing business is looking at the biggest rainmaker in the firm and assuming they need to become that person.

Maybe that partner loves working a room. Maybe they speak at conferences every month. Maybe they play golf with clients, entertain constantly, publish articles, dominate LinkedIn, or seem capable of turning every lunch into a new matter.

That works for them. It may not work for you.

Susan emphasizes that business development is not one size fits all. Lawyers need to understand their own strengths and build strategies around them rather than attempting to copy someone else’s personality.

I have seen this repeatedly throughout my career coaching lawyers. Introverts can become exceptional rainmakers. So can extroverts. Some attorneys are outstanding at one on one networking. Others are strong speakers, writers, connectors, educators, or strategic relationship builders. Some thrive in industry associations. Others develop business by becoming indispensable to existing clients.

The question is not, “How does the biggest rainmaker at my firm do it?” The better question is, “What am I naturally good at, and how can I turn that strength into a repeatable business development process?”

That is a much better place to start.

Business Development Is More Listening Than Selling

Lawyers frequently tell me they hate selling. My response is usually some version of, “Great. So do I.”

Traditional selling creates all kinds of negative images. Pitching. Convincing. Pushing. Talking about yourself. Trying to get someone to say yes.

That is not how strong legal business development needs to work.

Susan describes selling in a way that aligns closely with my Sales-Free Selling methodology. Start by listening. Understand what the other person is dealing with. Ask follow up questions. Learn what they are trying to accomplish. Determine whether you can actually help.

The lawyer who walks into a prospect meeting thinking, “How do I get this person to hire me?” is already placing unnecessary pressure on the conversation. The lawyer who enters thinking, “I want to understand what is happening and determine whether I can help” approaches the meeting very differently.

That difference matters.

You talk less. You listen more. Your questions improve. You stop trying to force your solution into every situation. Most importantly, the prospect gets to experience what it might actually feel like to work with you.

Great Questions Can Be More Powerful Than a Great Pitch

Lawyers are accustomed to demonstrating expertise by having answers. Business development often requires the opposite skill: knowing what to ask.

If a prospective client describes a challenge, your instinct may be to immediately explain what you know and how you would solve it. But if you move too quickly, you may be solving the wrong problem.

Ask another question.

What has been happening? Why has this become important now? What has already been tried? Who else is involved? What happens if the problem continues? What would a successful outcome look like?

These questions accomplish something a polished pitch rarely does. They demonstrate curiosity and help the other person feel heard.

They also give you information.

You may discover that the issue is much larger than the prospect initially described. You may learn that another attorney is better suited for the work. You may realize that timing is wrong or that expectations are unrealistic.

That is why I frequently tell lawyers to diagnose before prescribing. You would not want a physician recommending treatment before understanding the symptoms. Lawyers should not approach prospective clients that way either.

Trust Often Requires a Little Vulnerability

Lawyers are trained to project competence. That makes sense when clients are trusting you with significant legal issues, but there can be a downside when professionalism becomes a wall.

Susan and I discussed the role vulnerability can play in building rapport. Vulnerability does not mean oversharing or undermining your credibility. It means allowing people to see that there is a human being behind the law degree.

You can acknowledge that you faced a similar career challenge. You can admit that you do not know something and will find out. You can talk honestly about lessons learned. You can show genuine curiosity rather than pretending you already understand everything.

Trust rarely comes from appearing perfect.

People tend to connect with people who are credible, interested, authentic, and willing to engage with them as human beings. That is particularly important in a profession where clients may already feel intimidated by the legal process.

Expertise may get you considered. Trust often determines whether someone actually wants to work with you.

Relationships Need Time to Become Business

Another mistake lawyers make is placing a stopwatch on every relationship.

They have lunch with someone twice and wonder why no referral has appeared. They attend three networking events and decide networking does not work. They post on LinkedIn for a month and wonder why the phone is not ringing.

Strong professional relationships rarely develop according to our preferred timetable.

Susan points out that relationships that eventually produce business can take years to develop. Timing plays a major role. Someone may like you, trust you, and understand exactly what you do but simply have no reason to hire or refer you today.

That does not make the relationship unsuccessful.

This is where desperation can become dangerous. If you enter every conversation needing business immediately, people can often feel that pressure. Your questions become less genuine because you are searching for an opening. You start evaluating people based on whether they can help you right now.

The better approach is to develop the relationship without forcing the outcome. Stay visible. Be useful. Follow up. Look for ways to help. Keep the relationship moving.

When the timing eventually becomes right, you want to be the person they already know and trust.

Why Mid Level Associates Reach a Career Crossroads

Susan’s work focuses heavily on mid level associates, and for good reason. This can be one of the most complicated stages of a legal career.

The earliest years often come with substantial structure. Associates receive training, assignments, feedback, and clear expectations around developing technical legal skills. Then, somewhere in the middle, the rules begin changing.

Now the associate may be expected to supervise junior lawyers, manage client relationships, demonstrate leadership potential, become more commercially aware, and begin developing business. At the same time, the path toward partnership may still feel unclear.

That can lead talented attorneys to question whether they are in the right firm or even the right profession.

Susan believes firms need more structured development during this period. Mentorship matters, but so does sponsorship. Associates need people who will not only provide advice but also advocate for them, create opportunities, and help them understand what advancement actually requires.

Without that support, leaving can start to feel like the only available option.

Don’t Make a Career Decision Without Understanding Your Options

When lawyers reach a career crossroads, they can fall into binary thinking.

Stay or leave.

Make partner or go somewhere else.

Remain at the firm or abandon BigLaw entirely.

Susan encourages lawyers to resist making major career decisions before understanding the full range of options available to them. Sometimes the issue is not the profession or even the firm. It may be a lack of mentorship, an unclear role, poor communication, a practice area mismatch, a missing sponsor, or a business development challenge that can actually be addressed.

Talking with someone who understands the profession can help a lawyer see possibilities they may not recognize on their own.

I think this lesson extends beyond associates. Lawyers at every level can benefit from outside perspective. When you are living inside a problem every day, your options can look much narrower than they really are.

A mentor, coach, sponsor, trusted colleague, or advisor can help you see around the corner before you make a decision that is difficult to reverse.

Making Partner Does Not Automatically Make You a Leader

One of Susan’s strongest observations is that law firms frequently promote talented lawyers into leadership roles without giving them meaningful leadership training.

A lawyer becomes a partner because they are an excellent attorney, generate revenue, have strong client relationships, or meet the firm’s partnership criteria. Suddenly they are expected to lead teams, delegate effectively, provide feedback, mentor associates, manage conflict, influence colleagues, and develop the next generation of lawyers.

Those are completely different skills.

As Susan puts it, “Making partner is a title. It doesn’t make you an effective leader. Leadership is a skill; it can be practiced, and it can be taught.”

I think that distinction is incredibly important.

Leadership should not be treated as something people either naturally possess or do not. Lawyers can learn how to delegate. They can improve at feedback. They can become better communicators. They can learn how to develop people and influence colleagues without relying solely on authority.

But first, firms have to recognize leadership development as something worth teaching.

Delegation Is Part of Becoming a Better Leader

Many successful lawyers struggle with delegation because their careers have rewarded individual excellence. They became successful by doing high quality work themselves, often under significant pressure.

Eventually, that becomes a limitation.

You cannot build a team if you refuse to let other people do meaningful work. You cannot develop junior attorneys if you fix everything yourself. You cannot create additional capacity for business development if every task continues flowing through you.

Effective delegation does not mean handing someone a project and disappearing. It requires setting expectations, providing context, allowing appropriate autonomy, reviewing work, and giving useful feedback.

It also requires accepting that someone else may not do the work exactly the way you would.

That transition from individual performer to leader can be difficult, but it is essential for lawyers who want to build practices rather than simply remain extremely busy attorneys.

Firms Need to Develop People Before They Lose Them

Law firms invest tremendous resources recruiting talented lawyers. Losing strong mid level associates can therefore be expensive in ways that go far beyond replacing one employee.

Institutional knowledge leaves. Client relationships can be disrupted. Teams lose continuity. Recruiting and training start again.

Some departures are inevitable and even healthy. But others may happen because the lawyer could not see a future inside the organization.

Structured development can help change that. Associates need clarity about what advancement requires. They need feedback before something becomes a serious problem. They need opportunities to develop business, manage relationships, supervise others, and build leadership skills.

They also need people who are invested in their success.

If firms wait until a talented associate submits a resignation letter to ask what could have been different, the conversation is happening far too late.

Business Development and Leadership Have Something in Common

At first glance, business development and leadership may seem like two separate skills. One brings in clients. The other develops people.

But our conversation highlighted an important connection between them.

Both begin with understanding other people.

A strong business developer listens to a prospective client instead of dominating the conversation. A strong leader listens to the people they manage instead of assuming everyone needs the same thing.

A good rainmaker identifies what matters to the client. A good leader understands what motivates and challenges the people around them.

Both require trust. Both require communication. Both improve through practice. Neither requires you to become someone you are not.

That should be encouraging for lawyers who believe they simply were not born to sell or lead. These are skills, not personality types.

Build Around Your Strengths, Then Develop the Skills You Need

There is no single model for becoming a successful lawyer, rainmaker, partner, or leader.

Your path may look completely different from the person down the hall.

Start by understanding your strengths. If you are a great listener, use it. If you are an exceptional writer, build visibility through content. If you connect well one-on-one, develop a strategic networking process. If you enjoy teaching, speak and educate. If you have strong client relationships, deepen them and look for opportunities to expand those relationships.

Then identify the skills you still need to develop.

Business development can be learned. Leadership can be learned. Delegation can be learned. Networking can be learned. Giving feedback can be learned.

You do not have to become someone else.

You have to become more intentional about developing the best version of the lawyer and leader you already are.

Key Takeaways

• Business development for lawyers is not one size fits all. Build around your own strengths instead of copying your firm’s biggest rainmaker.
• Selling does not have to mean pitching or convincing. Listening, asking better questions, understanding needs, and determining fit can create stronger business development conversations.
• Lawyers should diagnose before prescribing rather than jumping immediately into explaining their expertise or solution.
• Trust can grow when lawyers allow appropriate vulnerability and genuine human connection into professional relationships.
• Strong referral and client relationships can take years to develop, so lawyers should avoid placing immediate pressure on every interaction.
• Mid-level associates often face a development gap as expectations shift from technical excellence toward leadership, client management, and business development.
• Mentorship and sponsorship can help lawyers understand their opportunities and navigate important career decisions.
• Partnership is a title, not proof of leadership ability. Delegation, feedback, communication, and people development are skills that can be taught and improved.
• Firms that want to retain strong associates need to invest in development before those lawyers begin looking elsewhere.
• Leadership and business development share a common foundation: understanding people, building trust, communicating effectively, and listening carefully.

A Quote to Remember

“Making partner is a title. It doesn’t make you an effective leader. Leadership is a skill; it can be practiced, and it can be taught.” — Susan B. Silverman

Frequently Asked Questions About Lawyer Business Development and Leadership

How can lawyers develop business if they hate selling?

Lawyers do not need to rely on traditional sales tactics to develop business. A relationship based approach focuses on listening, asking thoughtful questions, understanding problems, developing trust, and determining whether the lawyer can genuinely help. For many attorneys, this approach feels far more natural than pitching services.

What is the best business development strategy for a lawyer?

There is no universal strategy that works for every lawyer. The strongest approach generally combines the attorney’s natural strengths with access to the right prospective clients and referral sources. That could include one on one networking, strategic partnerships, speaking, content creation, client expansion, industry involvement, or a combination of several activities.

Can introverted lawyers become rainmakers?

Yes. Successful business development does not require being the loudest person in the room. Introverted lawyers may excel at deeper one on one relationships, listening, preparation, thoughtful follow up, writing, niche expertise, and other activities that can produce significant business over time.

Why is listening important in legal business development?

Listening helps lawyers understand the prospect’s actual needs instead of making assumptions. Better listening leads to better follow up questions, stronger rapport, more accurate qualification, and a clearer understanding of whether the lawyer is the right person to help.

How long does relationship based business development take?

Meaningful professional relationships can take months or years to produce business. The timeline depends on the type of legal service, the strength of the relationship, the client’s needs, and timing. Consistent relationship building is generally more sustainable than approaching every interaction with an immediate expectation of revenue.

What is the difference between mentorship and sponsorship for lawyers?

A mentor typically provides advice, guidance, perspective, and support. A sponsor goes further by advocating for a lawyer, creating opportunities, making introductions, and helping that attorney gain visibility with people who influence advancement. Lawyers can benefit from both as they progress through their careers.

Why do mid level associates leave law firms?

Mid level associates can leave for many reasons, including unclear advancement opportunities, insufficient development, workload concerns, compensation, culture, practice fit, leadership issues, or lack of mentorship and sponsorship. Firms that create clearer development pathways may be better positioned to address some of these concerns before an associate decides to leave.

Does making partner mean a lawyer is ready to lead?

Not necessarily. Partnership recognizes professional achievement but does not automatically teach someone how to delegate, coach, provide feedback, manage conflict, motivate others, or develop talent. Leadership requires its own skills and should be intentionally developed.

Can leadership skills be taught to lawyers?

Yes. Skills such as delegation, feedback, communication, coaching, influence, team development, and conflict management can be learned and improved through training, practice, feedback, and experience.

What should a lawyer do before making a major career change?

Before making a major decision, it can be useful to clarify the actual problem, understand the available options, and speak with trusted mentors, sponsors, coaches, or advisors who can provide an outside perspective. A career crossroads may have more possible solutions than simply staying or leaving.

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About Susan Silverman

Former commercial litigator and business development expert Susan B. Silverman helps law firms retain top mid level associates, strengthen their leadership pipeline, and build systems that drive long term growth. Having experienced firsthand how firms invest heavily in early training but leave mid level associate development inconsistent, she acts as a trusted advisor to firm leadership to bridge structural gaps on the path to partnership.

Her work focuses on helping attorneys and firms recognize that business development, leadership, relationship building, and professional growth are skills that can be intentionally developed rather than abilities lawyers are simply expected to figure out on their own.

Connect with Susan Silverman

Website: https://susanbsilvermanconsulting.com/

LinkedIn: https://www.linkedin.com/company/susan-b-silverman-consulting-llc/home/

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