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    Wisconsin Lawyer
    September 09, 2019

    Difficult Clients: When to Draw the Line

    There are many reasons to exercise scrutiny when accepting new clients. Learn how to identify prospective clients whose personalities and behaviors are likely to make them difficult or impossible to work with.

    Derek A. Hawkins

    angry caller

    Dealing with difficult clients is a ubiquitous rite of passage that comes hand in hand with the practice of law – or at least this is what I believed during my first few years of private practice. After all, as lawyers we are service providers; regardless of the legitimacy of a client’s gripe, “the [client] is always right!” (as so eloquently stated by Harry Gordon Selfridge).

    But I’ll be candid. I disagree with this sentiment; I believe this line of thinking is one of the most dangerous philosophies a lawyer, or any other service professional, can adopt. Sometimes a client is 100 percent wrong. Sometimes a client is a person who should have never become a client in the first place.

    What I find peculiar is that even when clients ignore their lawyers’ advice, are disrespectful, and engage in behavior that would be considered incredibly out of line in a nonprofessional social setting, lawyers tend to overlook unacceptable behavior, hoping that these clients will continue to refill their retainers, become references, or help enhance the lawyer’s professional network. The constant need to perform for the client and ensure his or her happiness, even at the expense of lawyers’ own well-being, has contributed to high levels of depression, alcoholism, and destructive mental health patterns for many people in the profession.

    No more! We can identify problematic clients early, attract prospective clients who align with our vision and temperament, maintain profitability, and more importantly, maintain our sanity in the process. Here is how to do it.

    Readily Identify Problem Clients

    Difficult clients come in many varieties; in my practice, I’ve categorized problematic clients into four main categories:

    Derek A. HawkinsDerek A. Hawkins, Marquette 2013, is trademark corporate counsel at the Harley-Davidson Motor Co., Milwaukee. He previously operated a Milwaukee-based private practice focusing in trademark law and served as general counsel for Markable Inc., an AI-based startup in Madison.

    1) The Haggler. You’ve rendered services to the client, you send an invoice, and the client tries to talk you into discounting your fee. Alternatively, at the inception of your engagement, the client asks for heavily or partially discounted services. These are signs of a client who does not value your work.

    Avoid the haggler by having conversations about fees early and often. Avoid negotiating yourself into a smaller fee and devaluing your services further. Unfortunately, sometimes close friends and family members are hagglers.

    2) The Forum Shopper. Some clients can’t take no for an answer. After coming to you for legal advice and receiving guidance that does not align with their desired course of action, they may ask for advice on the same issue from a colleague, another associate, or a partner, undermining your position and expertise even though they hired you to do the job.

    3) The Unblameworthy. Clients in this category might be the worst. These clients blatantly ignore your legal advice and engage in conduct that is detrimental to their legal rights and in direct contravention to the counsel you provided. However, despite your guidance to the contrary, you are blamed and the client fails to acknowledge their contribution to their own negative situation.

    4) The Never Satisfied. No matter the quality of counsel, there are some people who will never be satisfied. It can be very difficult to work with this type of client, so if you find yourself in a position where you are consistently butting heads with a client and it begins to affect your ability to provide the level of counsel to which you are accustomed, it may be best to terminate representation if, given your particular circumstances, doing so is allowable under the rules of professional conduct.

    Once you can readily identify the types of clients, you can begin to put together a systematic plan of action for dealing with difficult clients.

    Sometimes a client is 100 percent wrong. Sometimes a client is a person who should have never become a client in the first place.

    Create a Safe Space to Practice

    Far too often lawyers approach the attorney-client relationship as a client-driven dynamic in which lawyers are subservient to clients and their demands. Allowing the client to solely dictate the pace and details of work creates an unhealthy environment that is a breeding ground for negative outcomes. Overall, lawyers experience high levels of alcohol use disorders, and display signs of depression and stress at a rate that is more than three times the rates of other professional populations, according to a study conducted by staff of the Hazelden Betty Ford Foundation and the State Bar of Wisconsin.1

    Some of this could be due to the innate desire to be perfectionists and please clients, a natural extension of not being in control of the attorney-client dynamic. Lawyers who take some proactive steps early in the attorney-client relationship can begin to reverse some of the toxic effects that seem to be inherent in the practice of law.

    Codify Client Expectations. What are your practice’s stress points? This will vary depending on practice area and your workflow. However, identifying the elements of the attorney-client relationship that ultimately become hindrances to your practice can be a catalyst for creating policies that help avoid these hindrances altogether. Agreeing on one method of communication, placing adequate disclaimers in your engagement letter, setting billing policies – these are but a few areas for which having clearly codified policies can go a long way. Should a dispute with a client arise related to communication methods or billing practices, it is a point of comfort, and in some cases protection, to have written policies in place.

    Set Clear Boundaries. Unfortunately, when it comes to engaging in inappropriate conduct, some clients will happily toe the line if given the chance to do so. Codifying boundaries within your engagement letter and discussing these boundaries in early consultations will set the tone for your professional relationship.

    Are you comfortable with your clients sending text messages to your personal mobile device? Calling you after hours? Visiting your personal residence? Dropping by your office without an appointment? The answers to these questions will vary depending on personal preference and what is generally acceptable for your practice area, but the root message remains – set clear boundaries early and stick to them. After all, boundaries are only as effective as is their enforcement.

    Define the Scope of Work. Ambiguity can be a practicing lawyer’s worst enemy. Even when the scope of the engagement is abundantly clear, some clients will forget and expect the lawyer to perform work that is outside the defined scope area.

    Create a very detailed description of the work you are performing for your clients, to the extent allowable, and stay within the scope. If the client asks you to perform work that exceeds the original scope, notify the client that any extension of services must be memorialized in a separate agreement.

    Discuss Money Early. Determine if the client can afford your services. (This does not apply to pro bono services or volunteer legal services.) For paying clients, you will want to determine early on if your services are within their budget. If not, both the potential client and the lawyer should be able to walk away before expending additional resources. These conversations can be uncomfortable, but they are vital to ensure you are not put in a position where you allocate valuable time to a project for which you will never be paid.

    No Free Thinking. You will likely encounter clients who are very eager to get to work. After an initial consultation, they may flood your inbox with documentation and ask numerous questions seeking legal advice and deliverables. While it may seem time effective to begin immediately, doing so can create a dangerous starting point for the attorney-client relationship – making it difficult to determine which work was provided pre-and post-engagement.

    Make very clear that before you will render legal services, there must be a formal engagement that is memorialized in writing and fully executed by both you and the client. If you do not value your thinking and expertise, neither will your clients. Some clients will attempt to get as much free counsel as possible before paying. Be very clear in your consultations and engagement paperwork that you will not begin to provide any guidance until you are formally engaged and payment is rendered in accordance with your fee structure, whether it is a flat-fee structure or retainer.

    Allowing the client to solely dictate the pace and details of work creates an unhealthy environment that is a breeding ground for negative outcomes.

    Document, Document, Document. Memories are fickle, and when a dispute arises, exaggerated versions of the truth tend to flood the minds of even the most well-intentioned person. To avoid relying on such embellished recollections, be sure to document every interaction you have with clients. Write down the content of conversations, send emails to confirm clients’ understanding of advice and action items, retain notes and information clients provide, and save all voicemail messages in a readily accessible format. If a dispute with a client arises stemming from legal services, having meticulous notation of every interaction with the client will be a godsend.

    Keep Adequate Malpractice Insurance. If something goes wrong and a client wishes to hold you liable, you do not want to stress over your personal assets being on the line or having to fund your defense alone. Always keep malpractice insurance up to date, even if you practice law less than full time.

    Overcommunicate.In some situations, clients become irate because they feel their attorney is not providing them with the level of attention they desire and may expect. While this does not mean lawyers must check in with their clients every day, setting clear, reasonable touchpoints with clients and discussing how often they will occur will let clients know they are not an afterthought.


    Intentionality can drastically alter the dynamic of a law practice and the relationships between lawyers and clients. Instead of allowing the attorney-client relationship to ebb and flow based on the will of the client, control the relationship and be intentional with the way you attract and retain clients. Set clear guidelines and practices that filter out potentially problematic clients and that attract high-quality clients who will pay their bills to find and retain you. Doing so will result in more peaceful days and more enjoyable work.

    Meet Our Contributors

    What are you most looking forward to in the next month or so?

    Derek A. HawkinsOn the personal side, I am excited for back-to-school season. My kids are very excited to start school in the fall, which came as a surprise to me because thus far they have been raving about their summer vacation. That said, the back-to-school process has been a treat in recent years. My 6 year old loves getting new clothes and supplies. He will be attending first grade this year so I am very excited that he is eager to continue his education!

    On the professional side, I am looking forward to serving as vice chair of the State Bar of Wisconsin Intellectual Property and Technology Law Section board. In this new role, I am excited to work with my fellow board members to plan IP and technology-related continuing legal education programs for other State Bar members, coordinate outreach to law students at the U.W. and Marquette law schools to spark interest in a career in intellectual property, and serve State Bar members as best I can.

    Derek A. Hawkins, Harley-Davidson Motor Co., Milwaukee.

    Become a contributor! Are you working on an interesting case? Have a practice tip to share? There are several ways to contribute to Wisconsin Lawyer. To discuss a topic idea, contact Managing Editor Karlé Lester at (800) 444-9404, ext. 6127, or email Check out our writing and submission guidelines.


    1 Patrick R. Krill et al., The Prevalence of Substance Use and Other Mental Health Concerns Among American Attorneys, J. Addiction Med. (Jan.-Feb. 2016).

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