Leadership Skills Development Exercise

Below are four leadership development exercises that will help you and your fellow lawyers test and improve your leadership skills. In addition below is a chapter on leadership development. Please send us any leadership exercises that you want us to post here to Herb@sbizgroup.com.


You are Chairman of a very large tax law firm. The firm has never articulated the “decision rights” within the firm. There is an Executive Committee which makes the hiring and firing decisions, deals with big issues like large investments in technology, real estate leases, and opening new offices around the US and abroad. The firm has an international presence and over 1,000 lawyers.

The tax law firm is approached by a very large accounting firm and asked to write opinions on a series of tax shelters. Your law firm has over America’s history written a substantial part of the tax code. It is clear the accounting firm will demand that the opinions be favorable to what the accounting firm wants to do with these tax shelters.

The lawyers who have been working on this accounting firms’ matters for over 50 years approach the Executive Committee and say they want to accept this work. The Executive Committee agrees and it comes to your desk. You study the tax shelters carefully and you believe the shelters will not pass IRS muster and you believe that the shelters violate some of the basic principles your firm has written into the tax code, such as the ability to take losses on investments must be tied to the amount of basis one has in an investment or the amount risked by the investor.

As Chairman of the firm, what do you do?

What are the leadership principles involved in how you make your decision?

What decision you make?

Do you take into account how this decision might affect your future longevity as Chairman of the firm or even being a member of the firm? Please answer why you should and why you should not take this into account?

And finally, how do you, as Chairman, use this situation to impress upon your law firm colleagues that the firm needs to develop a clear, written set of “decision rights,” and begin to allocate decision making authority among various departments, sections, or practices within the firm.

Please do not answer the main question as if it is only an “ethics” question. This is a leadership question that involves ethics, certainly, but also includes how you lead, how you make decisions, how you listen to others’ points of view, and how tough decisions can create an opportunity for a firm or organization to improve how it makes decisions in the future.



Your law firm has a large internship program for second year law students. You have a full-time internship director. Each intern has one associate and one partner supervise the intern. If the intern does well, you have historically always extended an offer to the intern for a full time job after graduation and you let them know in September after the conclusion of the internship.

The interns are told never to help another intern on anything since the purpose of the internship program is to see how the interns sink or swim on their own. One intern comes in with the highest grades in his class and an amazing work ethic. Every project he is given he writes a stellar memo, performs exacting legal analysis, and does it very quickly. However, you hear that in August, when another intern is struggling, he helps her and actually even writes some of a brief for her. She does not acknowledge his assistance in writing because of the rule against helping other interns, but she does tell her supervisors that he helped her. It is now September and the internship director, the associate and the partner supervising the intern, and the Chairman of the firm get together to discuss whether to hire the intern.

You are the Chairman and you are preparing for the meeting. What do you expect the director of internships to say? What do you expect the associate to say? The partner? The decision to hire or not hire is yours alone as Chairman. How do you run the meeting? If you choose not to hire the intern, what future results would that decision cause? If you do hire the intern, what would the implications of that decision? What should you have done as Chairman well before this meeting to deal with this situation?



You have a client, a small business owner, who takes “loans” from his company instead of income, which is legal since his company has a significant line of credit that it is into. The client is sued for child support and the child support guidelines call for child support to be a portion of “income.” Your client demands that you take the position that the money is not “income.” What do you do?

Note, this is a leadership, not a legal question. The leadership question is: Do you have a duty to lead your client? If so, how do you lead your client? Assume that whenever the line of credit is paid up, which is supposed to be for one full month each year, at that moment, the loan technically becomes income, but that will be months after the child support hearing.


FOURTH LEADERSHIP SKILLS BUILDING EXERCISE: Somewhat hypothetical but happening all across the country…

Your legal organization, be it a law firm, in-house counsel office, a nonprofit organization that has a legal staff, an advocacy group, a city, county, state, federal legal office, or judicial organization, has numerous lawyers. Historically, the staff has been divided into separate sections with many lawyers working on their own and little collaboration taking place among lawyers. In 2010 you hired five new lawyers, raising the size of the legal staff to 15. In addition, you hired five paralegals and administrative staff, raising that number to 12. You are noticing these new hires are all “Generation Y” people, also called “millenials.”(born from roughly 1980 on).

These new hires are different from the staff that has been working in your organization for years. First, they use social media, instant communication, laptops, want to work from home, and demand that they not be put into “silos” and be allowed to work across the entire organization. Second, they take independent stands and never do anything just because the “boss tells the them to do it.” Third, they do personal things, surf the internet, use “SIRI,” the iphone digital assistant to order flowers for their grandmother while at work, and they dress like slobs, unless they know they are going to court.

How do you deal with this?

This is not copyrighted material and can be reproduced freely. Please acknowledge Herb Rubenstein when you use this material.




In order to be a better leader, one needs to become familiar with examples of leadership behaviors that have proven successful over time. Within each category and specific behavioral item listed in this chapter, there is great room for individual variations and creativity. However, there is little room for the leader of a law firm, a leader of legal organizations, a leader of clients, or an advocate for a client to ignore the items listed below and still achieve passing marks in leadership. There are approximately sixty behaviors that researchers believe constitute good leadership practices.

Checklist 1: People Management

A successful leader is one who:

Clearly communicates expectations

Recognizes, acknowledges, and rewards achievement

Inspires others and serves as a catalyst for others to perform in ways they would not undertake without the leader’s support and direction

Puts the right people in the right positions at the right time with the right resources and right job descriptions

Secures alignment on what is the right direction for the organization

Persuades and encourages people in the organization to achieve the desired results for the organization

Makes sure not to burn out people in the organization, looking out for their well being as well as the well-being of the organization

Identifies weak signals that suggest impending conflict within the organization and attacks the sources of conflict effectively

Holds people accountable

Encourages the human capital development of every person in the organization through training, mentoring, and education, and allocates sufficient resources to this endeavor

Correctly evaluates the actual performance and the potential of each person in the organization

Encourages people in the organization to stand up for and express their beliefs

Creates a non-fear-based environment in which all persons in the organization can speak the truth as they see it without concern for retaliation

Is able to empathize with those he or she leads

Checklist 2: Strategic Management

A successful leader is one who:

Is flexible when necessary to adapt to changing circumstances

Sets, with input from others including all stakeholders, the long-term direction for the organization

Understands the organization’s competitive environment, social trends, competitors, customers, and all stakeholders

Correctly analyzes the potential risks of all decisions

Correctly analyzes the potential returns of all decisions

Has the ability to focus on specific problems without losing his or her ability to see at the outer edges, gathering worthwhile information that others miss or fail to see as significant or relevant

Understands the strengths and weaknesses of the organization and how to exploit the strengths and address the weaknesses successfully

Develops and implements strategies to improve the strengths and to combat the weaknesses of the organization

Identifies appropriate partners, strategic alliances, and outside resources to tap in order to help further the organization’s goals

Articulates the values of the organization and develops strategies consistent with these core values

Demonstrates a strong commitment to diversity and positive change

Demonstrates a strong commitment to creating and sustaining a learning organization (learning is the foundation for all sustainable change)

Checklist 3: Personal Characteristics

A successful leader is one who:

Lives with honesty and integrity

Selects people for his or her team who are honest and have high integrity

Has the will, passion, and desire to succeed

Possesses a willingness to shoulder the responsibility for success (without being a “thunder taker”) and failure (without casting blame)

Is innovative and open to new ideas

Is not willing to accept the ways things are because they can always be improved; is never satisfied completely with the status quo

Is smart, intelligent, emotionally strong

Is confident without being arrogant

Is an able negotiator

Is willing to be patient

Is decisive when necessary

Is able to think analytically

Learns quickly

Is respectful to all

Is perceptive and sensitive to the needs of others

Demonstrates diligence, discipline, and strong perseverance capabilities

Is comfortable with ambiguity

Is willing to be original

Takes informed and intelligent risks

Checklist 4: Process Management

A successful leader is one who:

Manages change

Promotes innovation

Secures resources

Allocates resources wisely

Solves problems well

Anticipates crises

Handle crises well when they explode

Creates and manages budgets well

Creates and manages timelines and work plans

Possesses and manifests great project management skills

Translates long-term visions into step-by-step plans

Measures results and reports them accurately

Recognizes quickly when a process or activity is not working

Redesigns processes as often as necessary to be successful

These leadership behaviors and categories apply to lawyers and people in the legal profession just as they apply to leaders in every profession and organization. One might want to rate oneself and others on a scale of 1 to 10 on each of these leadership abilities. Individuals in the legal profession might also want to use “360 degree feedback,” asking those with whom they work, including peers, superiors, and subordinates, to rate them on each of these skills and abilities.

Knowing the full extent of this checklist may remind the lawyer and those in the legal profession of the importance of certain leadership behaviors that they may not have considered important in the past. Each skill or ability can be learned and can be improved. Self-awareness of one’s strengths and weaknesses is a first step toward improvement and improving leadership. This list of leadership behaviors can be used by all types of legal organizations as criteria to evaluate their employees and their leaders. Workshops and seminars can be taken to improve each of these skills and we recommend that such education and training programs be approved for CLE credit. Now we turn to an area of leadership that has not received much attention in the legal profession: motivation.


Motivation Explained and Demonstrated

Literature from 1974 provides some useful guidance on motivating oneself and others. House and Mitchell in their article “Path-Goal Theory of Leadership” state that leadership generates motivation when the leaders show that he or she has the power and influence to improve situations and undertakes the following behaviors:

  1. is willing and able to increase the kinds of payoffs that subordinates want,
  2. shows its willingness to create rapport with subordinates,
  3. works to make the subordinate’s jobs easier and more likely to be successful,
  4. makes sacrifices on behalf of subordinates,
  5. gives acknowledgement appropriately, and
  6. creates goals and objectives that are intrinsically appealing to subordinates.

Research on motivation shows that the following twenty-two factors are all essential to creating environmental conditions supportive of leaders motivating those they lead.

  1. Subordinates understand the goals of the group and its leaders.
  2. Subordinates know what is expected of them.
  3. Leaders maintain a friendly yet disciplined relationship with subordinates.
  4. Leaders consult with subordinates.
  5. Leaders coach and mentor subordinates.
  6. Leaders listen actively to subordinates.
  7. Leaders keep subordinates accurately informed.
  8. Leaders exhibit the same ethics they demand of subordinates and are trusted by subordinates.
  9. Leaders endeavor to understand the situation the subordinates face.
  10. Leaders set realistic individual and collective goals for subordinates and challenge subordinates in a way that engenders strong, positive responses.
  11. Leaders take into account the feelings and emotions of subordinates and try to accommodate their personal needs.
  12. Leaders give encouragement to subordinates.
  13. Leaders help subordinates become better problem solvers.
  14. Leaders tell the truth to subordinates and demand the same from them.
  15. Leaders deliver punishment effectively when warranted.
  16. Leaders are perceived by subordinates as being fair.
  17. Leaders create a vision for subordinates that both is realistic, comprehensible, and challenges their imagination.
  18. Leaders use humor appropriately.
  19. Leaders express appropriate confidence in subordinates.
  20. Leaders know the capabilities of their subordinates, demand that they perform at their highest levels, and let subordinates know that the leader is monitoring their activities against that standard.
  21. Leaders undertake substantial effort to help subordinates grow into leaders.
  22. Leaders resign when they fail or when their subordinates are not motivated to success by the leader’s actions, thus allowing another leader to take the reins.
  • Certainly, being able to motivate oneself and others requires additional important attributes, including the following:
  • Recognizing and avoiding burnout in oneself and others
  • Improving the ability of participants to delegate and achieve results through the work and cooperation of others
  • Articulating and understanding group dynamics, followership, and factors in communications styles, strategies, and content that affect the response of others
  • Recognizing the power of building long-lasting professional relationships
  • Implementing strategies to create and elicit rapport
  • Appreciating the value of one’s reputation and its relationship to motivation
  • Calling forth the leadership potential in others and in oneself
  • Knowing the role of fair and equitable treatment of others in achieving and maintaining high motivation.

Motivation is a critical component of leadership. In the legal community, lawyers and leaders of legal organizations are called upon every day to motivate associates, motivate staff, motivate court clerks and personnel to perform their duties well, motivate their clients to help gather facts and witnesses, and motivate themselves to serve as models in the community. Although people may believe that teaching motivation skills is difficult, this chapter has outlined many of the basic elements that go into successful efforts to motivate others. Lawyers and people working in the legal profession with their heavy work schedules, demanding clients and judges, challenging cases, and large areas of responsibility would be well served to understand some of the key theories and basic underpinnings of motivation and become better motivators. Each person in the legal profession will need to find an approach to motivation that works in a repeatable fashion over time. Motivation is a key element in avoiding burnout and in producing great results in teams and workplaces. Lawyers are faced with one type of a motivation-oriented problem that is rarely faced by any other professional. Because lawyers work in an adversary system, lawyers must often motivate their adversaries, motivate third parties such as juries and judges, and motivate government agencies and other tribunals to treat their clients fairly. Thus, the arenas where lawyers earn their living have special motivation-oriented challenges far beyond the challenges faced by most workers and most professions in our economy.