Executive Coaching for Attorneys

Are the same issues still getting in the way of your practice?

Is the billable hour causing problems at work and at home?

Are you in-house and struggling with navigating a corporate environment?

Are you ruminating about your career, wondering whether you are in the right place, in the right role, or in the right practice, and what the future will look like?

To be uncomfortably familiar with the edge of your limits is a feature of practicing law. You pack your caseload, responsibilities, and schedule to the very maximum and still accept more work along the way. You worry about whether work will continue to come in if you turn anything down. You also feel safe in being buried, in that it brings a sense of value and approval that you can showcase to others. Being able to tell clients and colleagues that you have more work than you can handle means that you are sought after, skilled, and worth it.

But when it comes to the actual work to be done, maybe you are also filled with doubt. Doubt as to whether this is the right approach, whether you missed something, whether you have the skill and knowledge to handle it, whether this is something you actually want to do, or whether you will have enough time and energy to do it. At the same time, you hesitate to express these and other doubts to your colleagues, clients, or others in your professional circle for fear of being perceived as incompetent, weak, or lacking the confidence that they want in their attorney or colleague.

Perhaps this has been the case for some time, and you are here looking for an executive coach that specializes in working with attorneys to help you build a more sustainable practice.

Law influences your sense of self, your relationships, and your career.

Practicing law is highly personal in that rather than your firm, your department, or your team, more often than not your clients and colleagues want to work with you. You know the cases, you know the history, your clients and colleagues trust you, and you know where to find everything. They all depend on you to solve, prevent, or mitigate their problems. They look to you for confidence and guidance in times of uncertainty when there is no clear answer or solution. Much of your work occurs in your mind, crafting strategies, responses, plans, and recommendations. As a result, you are personally needed, and in a very real way, you can work anywhere, at any time.

But sometimes you need help. Maybe you are struggling to get the clients and cases that you want. Or you blunder through communications and corporate politics, finding yourself on the wrong side of expectations in your annual reviews. Alternatively, you find yourself hitting a ceiling in your career progression or feeling some hesitation about the direction your practice is taking. Or maybe your ability to buckle down and grind through the work is no longer what it used to be and your outlook, relationships, and engagement have been suffering as a result.

If you are looking for support for these and other issues that reflects decades of experience successfully navigating a wide range of practice environments, Sidebar Counseling’s executive coaching specifically tailored for attorneys is right for you. Our approach combines both firsthand experience with practical, evidence-based approaches for navigating a variety of career-related challenges that are common among lawyers.

If this sounds like a good fit, all you have to do is fill out this form to get started.

For better or worse, being a lawyer is part of your identity.

It may not be great all the time, but being a lawyer is a large part of who you are. Collectively, we share common experiences, values, and views of ourselves, others, and the world. We all experienced law school, competed for rankings, ingrained in ourselves an instinct to issue spot, developed tendencies to catastrophize, cultivated a habit of judging ourselves and others, and established work and busyness as a currency for credibility and value. We are anxious and skeptical by nature because those characteristics are assets in practice. We argue because much of the profession is premised on an adversarial system, so we hammer the law when the facts are against us, hammer the facts when the law is against us, and hammer the table when everything is against us.

But this cannot be everything about who we are and how we operate. What works in the courtroom or the negotiating table often does not apply to how we manage ourselves as a person and a professional, or as a friend, a colleague, partner, or family member. When we are at the limits of our capacity, falling short of another expectation, facing the prospect of disappointing ourselves or someone we care about yet again, or missing out on another opportunity, we need to consider other ways of working. And sometimes it can feel as though doing anything else is impossible because we think we have already thought of all the possibilities. Which is why sometimes, we need to first overcome our characteristic fear of asking for help and reach out for support.

Over-commitment and over-engagement are common issues.

Especially in view of the foregoing, that lawyers tend to over-commit themselves to their work is widely recognized. The over-committed lawyer often underestimates the magnitude of new tasks and overestimates the resources available to them, giving rise to a persistent feeling of strain and anxiety. How often have you dwelled over your calendar, wondering how everything will get done? Further, where will the time and energy to invest in growth, changes, and improvements come from when you are already underwater?

Another characteristic of lawyers that is recognized in research literature is their tendency to over-engage in work. Over-engagement meaning a state where the dominant interest is in one’s work at the expense of every other domain of living and functioning. While work and career is a significant domain for many, the reality is that we also have other domains that reflect our emotional, relational, physical, and spiritual needs that must be met in order to live sustainably fulfilling lives. Consider the reality where you have more work than you could possibly accomplish while never feeling emotionally satisfied, closely connected with others, physically healthy, or spiritually content. Such is the potential reality of the chronically over-engaged attorney.

Executive coaching reflecting first-hand experience with managing these and other challenges can help you temper these characteristics while providing you with tools and strategies for achieving professional growth along with a more balanced life.

Executive coaching for professional growth and balance.

When your career centers on your ability to solve problems and push through times of difficulty, it can be difficult and frankly awkward to admit you could use a hand and seek help from others.

But executive coaching can provide you with perspectives, skills, and awareness that can give you what you need to practice more sustainably, make progress toward your goals, and pursue a more fulfilling life and career. Your executive coach can help you identify your strengths and weaknesses, the obstacles between you and where you want to be, and craft strategies for moving forward.

At the outset, we must first understand you, your professional history, your goals, and your motivation for seeking us out. We then dive into the details of your practice, routines, expectations, and habits to get a sense of how you currently operate. From there, we compare where you are now to where you want to be, and begin working through how we can connect the dots.

A tailored approach to executive coaching.

Leveraging more than 35 collective years of legal practice in various roles and environments with modern counseling skills, research, and best practices, we can draw from first hand experience in helping you:

  • Start your legal career off on the right foot, whether you are at a law firm, in-house, nonprofit, or government.

  • Transition between practice areas, locations, and roles, from coaches that have successfully lateralled internally across practice groups and offices of large law firms and externally to different firms and corporate roles, whether you are looking at pivoting to another practice group, moving to a different location, or ascending to greater positions of leadership.

  • Identify, evaluate, interview, and prepare for opportunities to move in-house, drawing from the perspectives of a chief legal officer of a domestic manufacturer with over $1BN in revenue and a former in-house counsel of a globally recognized CPG company.

  • Succeed as a law firm attorney or in-house counsel, from the collective experience of coaches with successful biglaw, boutique, domestic and international in-house, and solo experience, we can help you lead teams, be effective as outside counsel, manage corporate environments, and more.

  • Practice sustainably, from the perspectives of a C-suite executive and an attorney-turned mental health therapist, both of whom have first hand experience managing and overcoming wellness challenges while practicing law.

Ultimately the fit has to be right. If the experience and expertise at Sidebar Counseling can help you achieve your career goals we would be thrilled to be a part of the growth and development of your practice. If you have any questions about the services offered or would like to go ahead and get started, we encourage you to reach out.

You may have some questions about executive coaching…


What are the legal backgrounds of the coaches?

Matt previously practiced intellectual property law. He started his career in IP litigation at a large law firm in Milwaukee, lateralled internally to patent prosecution and moved to the firm’s Chicago office before joining Mars Wrigley Confectionery as IP Counsel. Matt later moved to Central Wisconsin, opening a solo intellectual property practice and joining Ruder Ware as Of Counsel before pivoting to a career in psychotherapy and coaching.

Edward is currently the Chief Legal Officer of a domestic manufacturer with revenues exceeding $1BN annually. Previously, he was the sole in-house counsel at JLG Industries and practiced commercial litigation at several large law firms and boutiques in Chicago. He mentored law students, attorneys, and professionals in non-legal roles before joining Sidebar Counseling as an executive coach.


How can you help me if my practice area/industry is different than yours?

There are consistent themes across practice areas and environments that consistently present challenges to new and seasoned practitioners alike, such as practice management, time management, communication issues, professional development, career progression, and so on. There are also characteristics and traits of lawyers in particular that can give rise to a number of issues regardless of practice area. The coaches at Sidebar Counseling are very familiar with these and other difficulties that attorneys face, including strategies and tools for overcoming them.


What are the benefits of 1/1 coaching over leveraging my own network?

The most important advantage is safety. As the coaches at Sidebar Counseling have no involvement in your personal or professional lives and maintain your information as confidential to the practice, you can safely discuss your true ambitions, fears, strengths, and weaknesses without worrying about whether doing so may impact your role or any of your stakeholders. If you are thinking about leaving your firm or your company, you can say so freely to us. If you worry about whether you can get through the next few weeks, we can talk about it. And so on and so forth.

In addition, we are trained and experienced specifically in helping lawyers like you work through professional challenges, and we have seen many examples of what does and does not work for different folks. Your time with us is focused on you and your well-being and success.

Achieve your career goals and practice sustainably.

If you want to overcome issues that are holding you back in your legal career and build up your confidence and performance abilities, we believe we help. To learn more about our approaches to executive coaching for attorneys, you can fill out the contact form and get in touch. We look forward to hearing from you.

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Executive Coaching
in Wausau

300 N 3rd Street
Ste. 302
Wausau, WI 54401

Virtual services are also available internationally.