Legal Coaching Explainer by Leigh Bailey

Legal Coaching Explainer by Leigh Bailey

Leigh Bailey, the Visionary and Founder of The Bailey Group, executive coach and development specialist, explores the ways in which coaching can improve an individual's performance and overall well-being. The piece offers advice for lawyers interested in engaging with a coach, utilizing case studies to illustrate how coaching can bolster and elevate lawyer development.

Reading Time: 5 minutes

I’m Leigh Bailey, the Visionary and Founder of The Bailey Group. I’m one of the most experienced executive coaches in the country, with an exceptional track record in guiding boards, CEOs, and executive teams toward peak performance. I’ve had the privilege of serving leaders across diverse sectors, including legal, technology, banking, financial services, insurance, advertising, marketing, healthcare, nonprofit, manufacturing, and beyond. 

What is your professional background and education? 

My professional background started with 10 years in banking and finance.  I was a front-line manager then transitioned to corporate Training and Development at Norwest Corporation focused on Sales and Management training. I observed that training could deliver information but not behaviour change. I was drawn to coaching because I wanted to make a difference in organizations and in leaders’ lives. I founded The Bailey Group 35 years ago. 

I have a B.S. in Mathematics with a Minor in Economics. My master’s degree is in Human Development with an emphasis in Counselling in Organizational Psychology and my coaching certification from New Ventures West.  

What benefits does executive coaching provide to the legal sector, specifically, private practice law firms? 

Few lawyers are trained to be effective leaders. Yet, Managing Partners and Practice and Administrative leaders require sophisticated leadership skills. Executive coaching offers customized leadership development for leaders in law firms in four key areas of leadership competence: 

  • Self-Mastery
  • Relationship Mastery
  • Results Mastery (working in the business)
  • Strategic Mastery (working on the business)

Coaching is helpful in building a strong team relationship between the Managing Partner and Chief Operating Officer. Benefits include enabling each to spend more time separately and together on achieving strategic goals (vs. spending time trouble shooting less important issues).   

Coaching is helpful in supporting Managing Partners to lead with courage, clarity and confidence A Managing Partner must take the lead in developing and communicating a clear and compelling future vision for the firm, aligning the Board and Practice Leaders to the vision, and holding the Board and Practice Leaders accountable for doing their part in execution. If the Managing Partner is more a politician than leader, he/she may be invested in pleasing firm partners rather than leading them.

The result is weak decision making and poor strategy execution. Too often, law firms aspire to grow via M&A asking for more revenue production or leadership time from partners without executing on these objectives. An executive coach will assist the Managing Partner to lead with courage, overcome resistance to difficult decisions, and hold the Board and other key leaders accountable. 

Coaching is helpful in building a cohort of aligned leaders including the MP, COO, Practice Leaders, and the Board. Alignment on strategy and key priorities is necessary for firm success. Coaching helps leaders at all levels to communicate clearly, foster improved employee engagement, and drive operating and strategic execution. It also helps to avoid Managing Partner and COO burnout caused by feeling that they are carrying the entire weight of leadership for the firm 

How can good governance help law firm owners, Managing Partners, and COOs to make better decisions and how can this be done through coaching?  

Timely and effective decision making requires that owners, Managing Partners and COOs are clear about their authority and accountability for making decisions. Managing Partners often seek consensus from the Board and other stakeholders for decisions rather than seeking input, considering differing points of view, and then making decisions in a timely way. Coaches help key leaders to learn decision making processes that lead to decisions that others will commit to and be accountable for executing. Coaches also help Managing Partners discern when it is time to “call the question” and make decisions that they own and must make. 

Why is leadership coaching valuable for law firm partners and COOs?    

Success as a COO requires both strong management and strong leadership skills. COOs must lead a team of experienced executives that is capable of driving business results for the firm. At the same time, the COO must have leadership and influence skills which allow her to act as a peer with the Managing Partner, owners, and the Board. Coaching helps COOs understand their strengths and development opportunities as leaders and to use this insight to build more productive and impactful relationships with the Managing Partner, Board, owners and direct reports. 

What type of firms and people have you worked with and why did they hire you to provide executive coaching?  

Full-service business law firms. Clients have included Boards, Managing partners, COOs, Administrative Service leaders (e.g., Chief Marketing Officer and team, Chief Information Officer and team), Cohorts of Practice Leaders and Individual Partners.  

The most common reasons they hired us include coaching the Managing Partner and Managing Partner/COO team and strengthening the partnership between the Managing Partner and the Board. 

When you first start working with a new client, how is that relationship established and how do you determine the business challenges and opportunities for that client as well as organizational culture and dynamics to help the client develop effective action plans?  

The relationship begins with separate discussions with the person to be coached and his/her leader regarding desired outcomes for coaching. Then the person being coached is interviewed regarding the expertise and demographics of a coach that he/she might prefer. Interviews with one or two potential coaches are set up with the person to be coached to allow him/her to select a best fit coach. A SOW is then prepared and signed which outlines desired outcomes and services to be provided. Most often the CHRO has been involved by this point and may be the person to sign the SOW.  Once the SOW is signed, a three-way meeting with the coach, person to be coached and that person’s leader is held to align on expectations and then coaching begins. 

Are there different stages and or processes with executive coaching and how are these determined?  

There are four stages to executive coaching: Assessment, Development Plan Creation, Execution of the Plan, and Measurement.  

  • Assessment includes both personality and 360° assessment using professional, reliable and valid assessments. 
  • Development planning is first done with the coach and coachee and then shared with the coachee’s leader to assure alignment. 
  • Plan execution involves on-going 1:1 meetings between the coach and coachee where issues are discussed, learning takes place, and new skills are practiced. 
  • The Bailey Group has developed a proprietary measurement process which measures both satisfaction with and impact of the coaching.

How do you manage your clients’ expectations?  

A list of expectations of the person to be coached and the coach are reviewed in the first session. These include expectations related to confidentiality, accountabilities, meeting cadence, scheduling and cancelling meetings, and other logistics. 

Is it possible to determine the results and successes of executive coaching and can you provide any examples of this?  

The Bailey Group has developed a proprietary system for measuring results of coaching. In addition, we use pre-and-post 360 assessment and customized surveys to assess impact. 

What are the biggest misconceptions about executive coaching?  

A common misconception is that the act of hiring a coach will somehow magically fix the “problem”. Behaviour change requires that the coach, the person being coached (i.e., the “coachee”), and the leader be clear, aligned and mutually accountable for achieving the coaching outcomes.  

A related misconception is that “confidentiality” means that the leader can’t be “in the loop” about the progress of the coaching. At The Bailey Group, our model includes on-going meetings, led by the coachee, with the coach, coachee, and the leader to maintain alignment and share feedback about progress (or lack thereof). 

Do you have a typical style or approach to executive coaching?  

Our approach emphasizes psychological safety, insight, challenging irrational or outdated beliefs, and being an accountability partner with the coachee for changing behaviour. Adults learn best when they feel it is safe to be vulnerable, authentic and to take risks. We use assessments to help coachees learn how they are perceived by others and to make sure their self-perception matches how others (their leader, peers and direct reports) see them. Changing behaviour requires recognizing and making conscious old habits and then intentionally choosing and practicing new behaviours. Coaches, to be effective, must be willing to respectfully challenge and hold coachees accountable when necessary.   

Leigh H. Bailey
CEO & Founder
The Bailey Group
Tel: 612-327-4030 

Published by: – July 2nd, 2024

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