BE AN ASSERTIVE LAWYER

'Clients hire lawyers not only for knowledge of the law, but for leadership'

I remember my Grandpa Gabe shaking my hand as a boy. With a wry smile he would grip my hand with an iron fist, look me in the eye, and encourage me to grip his hand just as firmly. In his thick South Shore Long Island timbre he would say, “Give me a good handshake Jimmy!” He taught me that a firm and assertive handshake leaves a good impression. A weak handshake invites judgment. A strong plumber, not a lawyer, Grandpa Gabe understood the necessity of being assertive.

Being assertive may not always be seen as the greatest of character traits. Indeed, being assertive can upset people. After all, the Psalmist wrote that the meek will inherit the earth. I can’t argue with the truth of this statement. However, the meek are often in need of an assertive lawyer to fight for them. Herein lies the need of assertiveness in the practice of law. Your clients might have the good character trait of being meek, but you must be assertive on their behalf.

Assertiveness is not an optional trait in the practice of law. It comes with the role. Clients hire lawyers not only for knowledge of the law, but for leadership. They expect direction when uncertainty dominates. Silence in those moments does not feel neutral. It feels like absence.

Assertiveness is often misunderstood. It is confused with aggression. It is mistaken for volume. It is conflated with hostility. None of those are required. Assertiveness is clarity paired with action. It is the willingness to state what matters and to move toward it deliberately, even when the path is uncomfortable. Being assertive often is as simple as making it clear what your client wants and pursuing your client’s goals with singularity.

The assertive lawyer understands that leadership rarely announces itself politely. Someone has to set an agenda. Someone has to decide what question comes next. Someone has to say, out loud, what others are privately calculating. That responsibility frequently falls to counsel, whether invited or not.

Assertiveness begins with having a plan. Pressure without direction is noise. A lawyer who presses without purpose risks confusion rather than progress. Preparation creates confidence. Confidence allows directness. Directness moves the room.

Being assertive can look rude but it is not. Clients often want to tell us a long story with many unnecessary twists and turns. An assertive lawyer must interrupt them and ask for the facts that truly matter in determining the issue at hand. Once the issue is determined, it is easier to direct the client to tell the story in a more focused way. Clients generally grant lawyers permission to be assertive in ways they cannot be themselves. That permission is part of the professional compact. A client may hesitate to ask a difficult question. A lawyer is expected to ask it. A client may avoid confronting an uncomfortable fact. A lawyer is expected to surface it. That role is not always pleasant, but it is essential.

Those questions are rarely comfortable. They probe motives. They test assumptions. They expose inconsistencies. Yet truth is seldom self-evident. It emerges through pressure applied thoughtfully. The assertive lawyer applies that pressure without apology.

Sir Francis Bacon observed that truth emerges more readily from error than from confusion. Error must be confronted to be corrected. Confusion lingers when no one challenges it. Assertiveness cuts through that fog. It demands definition and insists on clarity where ambiguity has become a hiding place.

In depositions, assertiveness shapes the record. In negotiations, it defines the range of possible outcomes. In court, it frames the issues the judge must resolve. In negotiating a deal, assertiveness shapes the ultimate deal points that make it into the contract. None of this happens passively. The assertive lawyer decides what deserves focus and insists on addressing it, even when resistance follows.

Assertiveness also involves making the ask. Many outcomes hinge on whether someone is willing to request what they want plainly. Settlement discussions stall when parties speak around their goals. Trials lengthen when lawyers avoid committing to positions. The assertive lawyer asks directly, knowing the answer may be no. A clear no is often more useful than an ambiguous maybe.

This willingness to ask extends inward. Assertive lawyers challenge their own clients. They push for clarity where clients prefer comfort. They encourage better preparation. They insist on honesty, even when it complicates the case. That pressure is not always appreciated in the moment, but it often proves decisive later.

Good coaches are rarely popular during training. They demand effort. They correct mistakes. They raise expectations. Over time, athletes recognize that those demands made them better. The assertive lawyer occupies a similar role. Encouraging clients to be their best frequently requires discomfort, and sometimes resentment.

Some clients resist this. Some resent being pressed. Assertiveness risks friction. Avoiding friction, however, does not serve the client. The assertive lawyer accepts that leadership carries the possibility of disagreement. Approval is not the metric. Effectiveness is.

There is also a collective dynamic at work. In many rooms, everyone senses the same problem. Everyone sees the same flaw. No one speaks first. When someone finally does, heads nod. Relief follows. The assertive lawyer often provides that release. By saying what others are thinking, momentum returns.

Philosophers have long associated courage with speech. Aristotle described courage as action in the face of fear, not its absence. Speaking assertively often carries risk. It may offend. It may expose error. It may fail. Avoidance feels safer. It is rarely productive.

Assertiveness also guards against drift. Legal matters have a tendency to sprawl. Issues multiply. Focus blurs. Deadlines creep. The assertive lawyer pulls attention back to what matters. That discipline saves time, resources, and credibility, even when it is unwelcome.

This does not mean assertiveness is constant. Timing matters. A skilled lawyer knows when to push and when to pause. Assertiveness loses power when overused. Its effectiveness depends on judgment. Silence, when chosen deliberately, can be assertive in its own way. The lawyer who has mastered the skill of assertiveness waits to be assertive until the tipping point of a cause appears. At the tipping point, a subtle assertiveness pushes things your client’s way.

There is a moral dimension to assertiveness as well. Injustice often persists because people hesitate to challenge it. The legal profession exists, in part, to reduce that hesitation. Speaking up is not always rewarded. It remains necessary.

Assertiveness does not guarantee success. It guarantees participation. It ensures that important ideas enter the conversation. It gives truth a chance to surface.

In practice, assertiveness shows up in simple ways. Setting expectations early. Naming risks plainly. Interrupting a spiral of irrelevance. Asking the question everyone hopes someone else will ask. These moments define leadership more than grand speeches.

Being an assertive lawyer does not mean dominating the room. It means guiding it. It does not require certainty about everything. It requires conviction about what deserves attention. Clients rely on that conviction.

Benjamin Franklin put the concept in very descriptive terms: “If you make yourself a sheep, the wolves will eat you.” As lawyers, we come across wolves often. Wolves want an easy meal. Being assertive protects both your clients and you. Rights don’t stand up for themselves. Truth does not announce itself. Progress does not occur by consensus alone. Assertiveness supplies the necessary friction. In a world full of hungry wolves, let’s all resolve to be assertive lawyers.  ⬛

Jim Vickaryous is the managing partner of the Vickaryous Law Firm in Lake Mary and formerly represented the 18th Circuit on The Florida Bar Board of Governors.

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