By Milana L. Hogan

PDQ, June 2022

If you’re a member of the legal professional development community, chances are you know a thing or two about coaching. At a minimum, you’re aware that the practice is gaining traction in the industry. Some of you even have full-time, in-house coaches for your lawyers and staff.

My first real exposure to coaching was at a NALP PDI conference in Washington, DC, where we received a bit of a crash course in the basic principles, followed by an opportunity to give some of our new skills a test drive in small groups. I remember two things about that session. The first is that I found the practice surprisingly difficult. My knee-jerk reaction, after listening to someone explain the challenge they were facing, was to immediately offer up a solution.

Apparently, I am not alone in my struggle to get and stay in the coaching mindset. As Jessica Natkin and Jessica Hernandez reveal in their new book, Let’s Coach All the Lawyers: An Essential Primer for Professionals Developing Legal Talent, “it is not uncommon for your inner voice to be screaming, ‘just do it like this!’” Importantly, the coaching mindset requires you to accept the notion that “the coachee has everything they need to solve the problem themselves” and then “quiet your inner voice by shifting the perspective back to the coachee.” Let’s just say that is easier said than done for some of us.

The second thing I remember about that session is how effective it was. Luckily for me, the members of my small group had a far easier time than I did getting into the coaching mindset, and we were able to make great progress in a very short amount of time. We followed that session up with a few phone calls, and many years later, I still remember exactly who was in that group, what we discussed, and how helpful the experience was to me.

Target Audience and Basic Premise

I try to adopt a coaching mindset when I can, however — despite having such a memorable and promising start — I have not done much in the interim to hone my skills or incorporate other coaching techniques into my day-to-day work. If I’m honest about it, this is largely because there is a lot of information out there and the prospect of sifting through it all seems both overwhelming and daunting. If you and I have this in common, Let’s Coach All the Lawyers is the perfect solution for you. Natkin and Hernandez wrote this book to offer “shortcuts and strategies from the world of coaching to enhance the effectiveness of those supervising, mentoring, or developing lawyers.” The good news for all of us is that you can still effectively deploy a number of coaching techniques even if you don’t have the time or inclination to pursue a full coaching credential.

The book is very easy to digest with helpful, real-world examples interspersed throughout. Published by NALP, Let’s Coach All the Lawyers has been thoughtfully organized into three parts: (1) Enhancing Your Lawyer Development with Coaching Techniques, (2) Employing Coaching Techniques, and (3) The Legal Environment. Part One focuses on the benefits of coaching — the “why” — and explains what coaching is and how it differs from other similar approaches like mentoring, supervising, and counseling. There is good data here on the ways in which “coaching makes a tangible difference to the bottom line” in each of the following areas: performance management, business development, career progression, supervision, mentoring and professional development, and outplacement. Part Two gets into the meat of how you do it — starting with Natkin and Hernandez’s career development model for lawyers, which serves as the backdrop for that section. Part Three offers a deeper dive into coaching in the legal environment, including how coaching skills can inform firm programs and processes, such as orientation, feedback, and even partner coaching.

Best Part of the Book

Actually, there are two best parts of the book! The first is that it is written, very specifically, for people who attempt to do what we do (develop lawyers) in the context we do it in (law firms and legal departments). Many of the coaching materials I have seen to date focus on coaching in a broader context without addressing the many “idiosyncrasies” we can and do encounter when coaching lawyers (as opposed to non-lawyers).

As anyone who has devoted time to trying to understand the lawyer brain will know, lawyers can be a difficult audience. They are (and we train them to be) highly skeptical, far more so than the average human, and this can make professional development programming challenging to implement. As industry veterans who have collectively held nearly every role there is — from practicing lawyer to professional development professional to consultant — Natkin and Hernandez bring a wealth of experience and a deep appreciation for these exact challenges, recognizing that “coaching can be a tough sell in a type-A, profit-driven, traditional environment.” In other words, they get it (e.g., they make the business case for the role of coaching in the very first chapter, correctly intuiting that this will be, for many of us, a gating issue). They also have a section of the book on “The Uniqueness of Coaching in a Law Firm or Legal Department” in which they provide a very nuanced, evidence-based analysis, drawing on the work of Dr. Larry Richard, Professor Ken Grady, and others, that explains some of these “personal and institutional peculiarities” and provides some practical ways to navigate them.

For me, this is a huge selling point of the book as it saves me the trouble of having to consider whether these techniques make sense for lawyers and then if I decide they do, having to do my own “translation” work. Recently, I met with a very well-established coach who I ultimately did not hire for exactly this reason: he kept describing the benefits of coaching in terms of the employee/supervisor relationship and while there are certainly parallels, it does not adequately describe either the partner/associate relationship or the professional development professional/associate relationship. At the end of the day, I found myself wondering whether — despite his past successes — he ultimately would be effective at a law firm.

            The other best part of the book is the wealth of checklists, charts, and templates that can be used immediately and “as is” or easily repurposed and customized to suit your needs. For example, there is a great Values Analysis questionnaire that lists out 50 values and is designed to help lawyers identify the values that matter most to them — an exercise that can be particularly helpful in a moment of crisis. There is also a terrific list of Powerful Questions — the kind that provoke deep self-reflection — that can be asked at different phases of the process. Like most professional development professionals, I’m a sucker for a good checklist.

Coaching and Connectivity

The COVID-19 pandemic has changed the world in myriad ways — some of which are wonderful and present new opportunities for all of us, and some of which introduce new and unforeseen challenges. One of the obvious challenges the pandemic-driven, hybrid work environment introduces is what I often think of as the connectivity challenge. If we’re no longer together in person five days a week, how do we maintain the critically important, professional relationships that an apprenticeship profession like ours relies upon? I give a lot of credit to the law firm professionals who are tasked with trying to crack this code; it has not been easy. While there have been shining moments of creativity during this time (e.g., a brilliant and mind-blowing magic show and a bizarrely entertaining night of Zoom karaoke), I am confident that we’ve all sat through our fair share of awkward virtual social events that fell flat.

Interestingly, and I was very encouraged to read this, coaching can be a terrific vehicle for connectivity. In Let’s Coach All the Lawyers, Natkin and Hernandez suggest that “a coaching mindset can help bridge this gap by emphasizing more purposeful interactions, making a more concerted effort to schedule time with those we are developing.” Coaching interactions tend to be far more meaningful and worthwhile than “agenda-less” check-ins, no matter how well intentioned. It is far too easy “for people to slip through the cracks when you’re not seeing them on a day-to-day basis.” Deliberate, focused conversations with a coach can drive associate engagement by signaling the firm’s commitment to their well-being and success. As a result, Natkin and Hernandez argue, “coaching is a sophisticated and effective way to enhance engagement, and, ultimately, retention.” Coaching all the lawyers won’t solve all your connectivity problems, but it has the potential to help you solve a lot of them.

Overall Recommendation

I don’t think I’ve taken the time to write a book review since elementary school. My fifth-grade daughter, coincidentally, is writing one as well — an assignment for school — on Fever 1793. Because writing a book review is not how she wanted to spend her spring break vacation, she asked me why I would voluntarily choose to do this. I told her, honestly, that I felt compelled to let people know about a tremendously good resource written by two very insightful and impressive women. Is there anything more fun than recommending a great book to friends and then excitedly discussing it with them after they’ve read it? This feels a bit like that to me.

It is also worth noting that while its specific and informed focus on the lawyer as coachee is one of the things I like best about this book, the basic principles can be applied in any domain. Just this morning, when my five-year-old was struggling to tie his shoes, and I was tempted to take over and do it for him, thereby putting both of us out of our misery, I reminded myself of the basic premise that “the power of a coaching relationship lies in empowering the coachee.” This thought helped me resist the urge to rush in with a quick fix and to give him the space (and time and encouragement) to solve the problem for himself.

The bottom line is that Let’s Coach All the Lawyers is a clever, tight, super actionable read that you will plough through quickly and then continue to use as a reference again and again. It is as relevant and resonant a book on coaching for lawyers that I have seen, and one of the best PD-focused books I have read, hard stop. Please do yourselves a favor and add this to your bookshelves!

Dr. Milana Hogan is the Chief Legal Talent Officer at Sullivan & Cromwell LLP. She is the Immediate Past Chair of the Professional Development Consortium and serves as a liaison to the American Bar Association Commission on Women in the Profession. She is also the author of the book Grit, the Secret to Advancement: Stories of Successful Women Lawyers, published in 2016. She lives in Connecticut with her husband and four children, ages 5, 7, 9 and 11.