Finding a True Reflection: A Guide to Executive Coaching for Lawyers

When I was promoted from my first in-house job, which was an individual contributor role, to be the leader of a team of lawyers and legal professionals, I thought I was ready to jump into new waters and would lead the team seamlessly. After all, I was a skilled lawyer who had deep expertise in the subject matter, and I had seen lots of other lawyers “supervising” during my time. However, I followed a model of “leading” that was destined to fail: I would make decisions. I would announce the decisions. And my team of lawyers and professionals would learn to do their work the way I liked it done.

What I quickly learned was that this is not leadership; it is a model of supervision (not leading) that does not build collaboration or inspire a team to innovate and deliver excellent results. I was lucky enough as that transition unfolded to work for a company that recognized the importance of high-end executive coaching for emerging leaders. My company engaged a world-class executive coach to help me navigate my new role over an extended engagement. It was the start of my journey to become an authentic leader and was one of the most transformative periods of my career, setting me on an entirely new path. It would also be the first of a number of coaching engagements I would embrace as my career unfolded, with each engagement focused on unique and targeted goals and transitions.

Because of the powerful impact of coaching on my development, when I speak or write on leadership for lawyers, I often highlight my perspective that coaching is an incredibly powerful tool for lawyers aspiring to lead. However, coaching for lawyers is still uncommon enough that I often get questions about how it works, how it affects lawyers in different stages of their career, and what considerations should be analyzed before undertaking a coaching engagement. In this article, I will demystify the different forms of coaching, and outline the considerations you will want to assess before engaging a coach to assist you in your career development.

Coaching in a nutshell

The first step is to understand what coaching is. A coach, in the career context, is a qualified professional who can partner with a coaching candidate on a range of developmental goals. These may include gathering data about themselves and their performance, growing their self-awareness, supporting the candidate in the identification and achievement of goals, providing real-time and candid feedback and analysis, and, in short, helping the candidate overcome any hurdles to achieve their full potential.

Coaches are typically engaged by the individual themselves, or the coaching candidate’s employer, and paid for their time on either an hourly or flat-fee basis. They partner closely with the candidate over a short or extended period, with one or more developmental goals in mind. Depending on the scope of the coaching engagement, the coach may engage other stakeholders (e.g., supervisors, peers, subordinates, and even friends and spouses) for feedback or insights over time, and may issue some type of work product (e.g., a set of feedback or other diagnostic reports) or no work product at all.

Different forms of coaching and how to identify the best one for you

Coaching engagements can come in many different forms, from very discrete engagements to full blown partnerships that last months or years. In their most discrete form, individuals may seek a coach to help them with a very specific issue, like improving their boardroom skills or better demonstrating their financial acumen. Mid-range engagements can come in the form of hiring a coach to guide you through your transition between jobs, coach you as you transition into a role of increased scope, or help you onboard into a new role. In their broadest form, coaching engagements come in the form of a multi-month, yearlong, or year-over-year engagement, during which the coach offers you support in the full range of your role and development goals. Many C-suite executives keep a coach on retainer to maximize their performance and development.

A coach may be the right fit for your development support during the following times:

• Making a move to a new stretch role outside of your expertise, or leading a team for the first time;
• Successfully launching your first C-suite role;
• Tackling any number of developmental complexities, from growing your self-awareness, to improving your communication skills, to increasing visibility or developing your business acumen;
• Learning how to grow and develop relationships with peers or subordinates;
• While in transition to clarify what’s next and how to get there;
• Learning how to thoughtfully build and resource a development plan, and how to fill out flat spots; and
• Gathering 360 feedback and leveraging results in a variety of ways to benefit your development.

Regardless of what your need is, it is critical to identify it and the motivation behind addressing that need, and what the impact will be in your career if you tackle it. It is also recommended that you pressure test the work you’re going to tackle with the right audience, for example your supervisor or your mentor/sponsor who can give you feedback about whether or not that work will truly benefit you in the ways you expect. In addition, and as discussed later, you can also test out these identified needs as you assess prospective coaches.

Assessing if you can benefit from a coach

Once you identify the developmental work you want to undertake, make sure that a coach is the right resource to support that work. I often have conversations with lawyers who think a coach sounds like a solution to any of their development complexities. Before you consider any coaching engagement, it is important to take a pause to consider if you can benefit from a coach and what you are trying to accomplish with that engagement. Coaching engagements are a monetary investment — and a significant time investment. Ensure that when you identify the work you want to undertake, that the tool fits the issue.

For example, if your development issues focus on the expansion of technical expertise or financial acumen, a coach is probably not the right fit for you. Your development investment may be better focused on leveraging the right educational opportunities or stretch assignments in your organization to gather those skills. Similarly, if you know that you are a person who — at this stage in your development — is not open to feedback and does not have the willingness to change, again, a coach is probably not the right tool. You should have a developmental need that is best fulfilled by feedback and reflective consultation with the right expert, and you must have a desire to make needed adjustments in your practices and development to evolve with the input of that expert coaching.

Types of coaches and how to find the right one

Coaches come in many shapes and sizes, and it is important to find the right one. As noted, you can find highly specialized coaches to support you in very targeted developmental needs, or you may be looking for a more robust executive coaching engagement to support you holistically. It is incredibly important to have a coach who you can trust, and is a good fit for you, in both style and substance. Some questions to ask yourself as you assess what kind of coach you need include:

• What are the developmental goals you are trying to accomplish?
• Does the potential coach have expertise in those areas?
• Are there certain coaching certifications I’m seeking?
• Does the potential coach have proven success in driving growth and development in those areas?
• Is the potential coach’s style a fit for me?
• Does the potential coach have clients that share my developmental needs?
• Does the potential coach have a format for coaching that is a fit for my desired investment (financial and time)?
• Do I know others who have worked with the potential coach and who may be able to offer me advice?
• Do I have relationships within my personal board of directors who can help me assess the fit of this coach for my situation?

There are a few different ways to find a potential pool of coaches for your issue. You can leverage your personal board of directors and network for referrals. In addition, there are several different websites that offer lawyer focused coaches that might offer you a starting point. Finally, you can also leverage your human resources department to help you find the right resource depending on your developmental need. Given the close and critical role a coach will play in your development, personal referrals are often the most powerful for overall success.

Once you settle on a list of potential coaches, you should do as much intel as you can on those coaches and their backgrounds and schedule an interview call with the potential candidates. During that call, you should express the topics highlighted earlier, as well as gather key information about the coach’s style, background, coaching areas in which they specialize, coaching process, and their qualifications and certifications, if any.

How to engage a coach and cost considerations

In advance of engaging and agreeing to terms with a coach, it is important to pause and consider whether you want this coaching engagement to be company sponsored. That sponsorship can come in two different ways, (1) investment of time or resources, and/or (2) investment of capital. If you desire engagement of your company in either or both ways, it is first important to discuss it with your direct supervisor, in partnership with your human resources team. Sometimes individuals can miss this important step and by doing so, eliminate the opportunity for your company to be a key partner during your coaching work and/or cover the cost of coaching.

Once you have aligned on whether you will be undertaking the coaching engagement on your own, or with some form of company sponsorship, you can begin to undertake the work of engaging your coach and agreeing on cost. Ensure that you have a robust and well thought engagement letter that outlines exactly what will be covered by the coaching engagement, and that clearly delineates the costs and how they will be paid. Coaching engagements can come in any range of costs, from a few hundred dollars an hour, to tens of thousands of dollars for a longer engagement.

You should consider the following topics in reaching a final agreement with your coach on the engagement:

• The fee arrangement for the engagement, who will make the payment, and when the fees will be paid;
• A potential “early out” if the coaching engagement turns out not to be a good fit at some interim point;
• Clear terms about how you will engage and communicate with your coach;
• Outline of what the phases of the coaching work will be and what work product the coaching engagement will generate;
• An identification of any 360 feedback tools and/or diagnostics that will be used;
• Confidentiality provisions that protect your information or make it clear how the content will be used;
• Clear understanding about what transparency, if any, your organization will have to the coaching work; and
• A provision that enables you to have and use the work well into the future.

Getting the most out of it

Coaching is a significant investment, regardless of the scope. Consequently, you should set yourself up for success to get the most of that work. That plan for success can include several different elements. First, start with yourself. Make sure that you are open and ready for the feedback that your coach provides and be prepared to grow. Always remember that growth can be uncomfortable and seeking out support along the way will be important to your overall success, both from your coach and from others. In addition, come to your conversations with your coach prepared with an agenda, either self or jointly prepared, and be ready to do the work. Make sure to keep notes of your coaching reflections in a separate notebook or in a file on your computer that you can reference for your progress, and to benchmark at the end of your coaching engagement.

Ultimately, coaching work is undertaken to move you along your career journey, and ultimately that evolution cannot occur in a vacuum. To that end, in many situations, it can be a powerful multiplier to share outcomes of your coaching work with relevant stakeholders to show (1) your investment in your development and its importance to you, and (2) provide understanding to others on how they can support you in your career growth.

Along those same lines, if your coaching is company sponsored or even company initiated, your organization will likely want to be engaged in different ways along with coaching engagement. That can include having transparency to the work along the process, gleaning understanding about how your supervisor, team, or the organization can support you in your development goals, or even getting a final report out on the outcomes of the coaching work and reset development and/or performance goals. Each candidate will need to be clear about her tolerance level for transparency along the way, and match that with the organization’s expectations.

Finally, it is important to understand that one of the most powerful things your coach can provide you is broader context about your organization, its leadership, and its strategy, and how you and your career development fit into those structures. If positioned in the right way, your coach can have access to your leader, and even expanded leadership, who can provide important feedback about your development goals and the way those goals, and the path you’ve mapped to achieve them, match up to organizational culture and opportunities on the horizon. In addition, they can often get data from within the organization, and feedback about the candidate, that the coaching candidate may not be able to obtain themselves.

Keeping your coaching work alive and using it to launch the next career phase

Once you complete your coaching work, don’t simply put it in a drawer and forget about it. That developmental work can provide you with refreshing perspectives over time, and it is good to dust it off at least annually. Make a note to review where you were, and more importantly, where you are, as well as where you are going. Capturing that investment and revisiting your developmental progress is part of the overall impact and value of a coaching engagement.

Moreover, development is a continuous improvement exercise, that must be revisited regularly and resourced in many ways. Your coaching work, whether discrete in time or over an extended period, can be a transformative experience that can alter the course of your career, or simply offer you a vision for your career that perhaps you could not have crafted on your own. Regardless of your goal, ensure you enter the process educated, as an advocate for yourself, ready to grow in response to feedback, and prepared to make the safest investment you can ever make — an investment in yourself.