30 Things I’ve Learned After 30 Years as an Estate Planner

I began practicing estate planning in the spring of 1987. I had been out of law school for less than a year, practicing in litigation at a large, prestigious firm in Chicago, meaning that I largely spent my days looking at documents in cases in which one faceless corporation was suing another. As I remember the story (facts do get fuzzy over time), a partner came to me and said that he had a small piece of probate litigation that he didn’t want to be bothered with. I think the case revolved around whether life insurance proceeds needed to be paid because there was a suspicion that the decedent had committed suicide. I don’t remember the result but I do remember that I was intrigued that the practice of law actually involved living, breathing (or dead!) human beings and human emotion, something I had not encountered as a commercial litigation associate before that. I spoke with a couple of the partners in the firm’s Trusts and Estates Group and asked if I could do some work with them and they kindly agreed to take me on. My only encounter with anything having to do with estates up to that time had been one morning session in my Bar-Bri class preparing for the bar exam.

I ended up leaving that firm later that year and joined the firm that I’m still with now, over 29 years later. That alone feels very good. In that time I have gone from as green as green can be, eagerly chasing after any small matter I could get, to an ACTEC Fellow with a successful and sophisticated practice and what I believe is a nice reputation within Chicago’s estate planning community, if not beyond. I think I’ve learned a thing or two in that time and this article is my effort to put some of that down on paper. I assume many readers will nod their heads in agreement at some items and shake their heads in disagreement at others. So be it. Hopefully, there is at least something of interest to each of you.

The Client

1. Start every encounter with a firm handshake. Yes, it makes a difference, even if the person with whom you are shaking holds your hand like a fish. I think it sends a message of trust, good will, and presence, even though it is such a simple act.
2. Make eye contact as much as possible throughout the entire meeting with a client. Nothing says “I’m interested” as much as eye contact. And nothing says I’m disinterested as much as failure to make eye contact. Sometimes you can sense a bit of self-consciousness, both in yourself and in the person at whom you are looking, but get over that. Clients, and referral sources, appreciate the body language of eye contact, whether they consciously realize it or not.
3. Your cell phone stays in your pocket and the ringer stays off throughout client meetings. Either you’re present or you’re not and either the client is the most important thing to you at that moment or not. Looking at a phone is the surest way to let your client know he is No. 2, which is a good way of not having many more meetings with that client. If you need your phone for some reason, then let the client know up front and why.
4. Take good handwritten notes at every meeting. I am not good at remembering what I had for breakfast, let alone information provided by a client at a meeting months if not years before. Then, scan the notes into your server as soon as the meeting is over. There is no better preparation for a future client meeting than to review the notes taken in real time at earlier meetings. I do not like taking notes on a computer during a meeting because I think that you don’t listen as well, you don’t make eye contact as well, and the computer comes across as a wall between you and client.
5. As much as we like to deny it, not every client is equal. I endeavor to be responsive to every client, returning phone calls and e-mails as fast as possible. But the truth is that some clients pay faster, some have deeper personal relationships with you, some have more time-sensitive work, and some are just nicer to deal with. If you have two calls to return in a hurry and one is from someone who always says thank-you and pays on time and the other is from someone who doesn’t, then you owe it to the first guy to return his call first.
6. Not every matter is actually urgent, let alone an emergency. That’s not to say that you don’t need to treat every matter with respect and do your best to get it out the door as quickly, accurately, and professionally as possible. You do. It is to say that perspective is important both in terms of setting client expectations and your own stress levels. My experience is that far more important than getting every project out the door immediately or responding to every e-mail in five minutes is setting up-front expectations with the client. As long as those expectations are realistic and you meet them, you are typically golden.
7. That also extends to after the work is done. Clients love follow-up—the occasional check-in on a draft estate plan, the e-mail every few months reminding them to fund their trusts, the letter telling them about changes in the law. This is great client service. It can also be great CYA: you are building a record when they come back to you and complain that something didn’t get done.
8. If you can’t explain the plan to the client so that the client fully understands what you are doing, then no matter how clever it is, it isn’t worth pursuing. You are not always going to be there to hold the client’s hand. First, it is practically impossible to do so. And, second, the client is typically not going to want to pay you to do so. A client with a plan that gets him 70% of the possible benefit but who will engage in proper compliance and be satisfied with the plan is much better off than the client with a plan designed to achieve 100% who won’t.
9. Clients appreciate candor. For every client who is offended that you may suggest that a certain family member may not be the right choice as a fiduciary, ten others will appreciate your candor in raising it. I acknowledge that is a much harder thing for a young lawyer to do, particularly with an older client. Often that is because of an internal sense that you don’t have the appropriate gravitas as a 30-year old that a 50-year old would. Fair enough, though as discussed below, the sooner you think of yourself as an “owner,” the sooner you will get over that. The client may or may not agree with the young (or old!) lawyer’s advice but they will rarely resent it. Likewise, the experienced lawyer (nicer than saying older) who fails to use that experience in counseling a client on personal matters is doing the client a disservice and not earning his or her presumably higher billing rate.
10. I also happen to think that it is okay to share your own personal experiences with the client and not just those that derived from client experiences. Your clients are more comfortable knowing the person who is sitting across from them. You don’t need to share every last detail about your kids. That’s a bore for all involved. But letting the client know a little of what makes you you, what makes your soul into what it is, what informed your values, the lessons you learned from your own parents, and so on, makes for a much richer attorney-client relationship. It also helps your client to understand the biases inherent in the advice being provided, ultimately helping the client to make better choices.
11. To put that point another way, I think that helping a client to pass values from one generation to another is just as important as helping them to pass value. Obviously, we can do much more to effectuate the latter. But drafting documents divorced from knowledge of the client’s values and personal goals and pain points, no matter how technically perfect those documents may be, is only doing half of the job. The arc of my client meetings has changed a lot over the years, with much of my time now spent just talking to the client about his family and business and world view (this is when the part about sharing a bit about yourself comes in, as that certainly deepens those conversations). That contrasts with how I used to handle client meetings as a young lawyer at which I felt obligated to share and ask about every last technical aspect of the documents. Now I spend precious little time doing that. My clients will now sometimes ask, “Am I being charged for this chitchat?” My answer is a resounding “Yes,” because the plan they walk away with will be both technically excellent and a much better reflection of what really makes the person across the table tick.

The Lawyer

1. Go home for dinner. Many younger lawyers trying to build a reputation within the firm or trying to build a practice feel that they need to cram every hour of every day with work and effort. Sometimes that is true. Deadlines do exist. But most of the time that feeling is not based on any reality beyond fear or poor planning. I believe that I am a better lawyer, a better counselor, a better person, and generally happier with my life and career because I had dinner at home with my spouse and kids as often as possible. If I needed to work on a weekend or after my kids went to bed, so be it. If I needed to miss the occasional dinner, that was OK, but that should be the exception and not the rule. I also typically had breakfast with my kids before they left for school. Again, not every day but most days. It is certainly possible that had I worked those extra hours instead I may have had an extra client here or there or a bigger hours-based bonus. But, honestly, I doubt it. And the trade-off would not have been worth it.
2. When you’re on vacation, be on vacation. When I’m on vacation I set up a specific time or two every day to check my e-mails and voice mails. That’s appropriate for client service, and it probably reduces my own stress by getting rid of any uncertainty as to what is going on at the office. But I do my best to not spend my vacation reviewing or writing documents or on client calls. Sometimes it can’t be helped and I’m almost always reachable, but usually it can be helped with just a little advance planning. You will be a better and happier lawyer when you return to the office by virtue of having turned off while out. And most clients respect your need to recharge and to have time to yourself. They want the same thing for themselves.
3. Eat at your desk as little as possible. Ten minutes in a lunch room with a colleague or two has never actually resulted in a missed deadline. And just imagine how much cleaner your keyboard keys will be. And you never know what interesting tidbit you may pick up (gossip or legal idea) simply by interacting with your peers, whether clerk, admin, lawyer, or otherwise. I also believe in spending a few minutes each day walking the halls. The respect you will earn by simply showing that you are part of the firm and not set off alone in your own space is hard to calculate until those people you hang with in the lunchroom hang around to help you.
4. I think it is hard to properly represent a client when spending all of your time in your office. Volunteer your time for an organization (but make sure that organization speaks to you and your values and never do it, in my opinion, because you think it will bring a client to the door). Read. Get in great shape. Study art. Get angry about politics and then do something about it. Even just participating in firm management provides you with a broader view. It doesn’t matter what you choose to do as long as you use your mind beyond your immediate workload.
5. From the first day I walked into my firm I was told to think of myself as an owner. That may mean picking up a paperclip from the floor. That may mean for a young lawyer treating the assigning partner as your client. It certainly means taking responsibility for all of your work, all of your successes, and all of your mistakes. Celebrate the one. That’s healthy. And admit to the other. That’s healthier.

But ownership is mostly a mindset. How do you view yourself within the workings of the firm? If you are a file room clerk and you view yourself as an owner you will be the best file room clerk out there. If you are a lawyer and you “own” the matters you are working on, whether generated by your own client or someone else’s, you will provide an excellent product in a timely manner, well thought out, with great follow-up. That is how owners behave. I would also say to younger lawyers that there are very few supervising partners who will not allow you to take ownership of a project for that partner if you demand it and act on it. Most importantly, that sense of ownership is also recognized by clients.

1. Mistakes are okay. Own up to them, learn from them, and don’t make them again. No one ever learned from being right all the time. I actually hate the idea of perfection because then you have no room for improvement or goals to shoot for. How dreary that would be.

The Practice

1. If an estate planner’s job is to help a client pass wealth from one generation to another (and I am not admitting to necessarily agreeing with the simplicity of this definition), then the estate planner needs to consider every probable risk to achieving that goal. Taxes, for sure, are one. But taxes are hardly the only threat and are an increasingly small risk with changes in the federal exemptions. Taxes are also rarely the reason that a client loses sleep at night, despite the protestations of many of our bloviating politicians. The client’s ability to pass on wealth is much more likely to be affected by divorce, business partners, family dynamics, litigation, environmental concerns, malpractice threats, and dozens of other issues unique to each particular client.
2. Thus, while an estate planner needs to be a technically adept tax lawyer in both income and transfer taxes, that alone is almost never enough. I remember the day I learned this lesson. Back in the 1990s, during the real estate bubble that burst before the most recent real estate bubble burst, we had a client with all sorts of guarantees on real estate deals. About the same time we had a client with general partnership interests in reinsurance syndicates with substantial casualty claims. The threat to these clients had nothing to do with taxes. But that didn’t change the nature of our obligations to help the client preserve his wealth for the next generation. Instead, we quickly became asset protection lawyers, using trusts and other traditional and nontraditional estate planning vehicles to help those clients (while avoiding assisting in a fraud no matter what).
3. That lesson, for me, also helped change my career. It became obvious to me that technically adept lawyers, without more, are both easy to find and easy to replace. If I ever wanted to be financially independent, I needed to be just as entrepreneurial as my clients. I loved the feeling of becoming an asset protection lawyer because that is what the market demanded. In 2008 and 2012 we were great business succession lawyers. In 2009–2010 we were great protectors of the bottom line. In the early 2000s we helped LGBT clients navigate family dynamics and unfriendly tax laws. By 2012 or so that was no longer an issue. In the early 2000s because of a client situation we had the opportunity to counsel a bank on trust and fiduciary issues, a practice that we’ve continued to grow over the years. As baby boomers retire we become much more adept at dealing with options for IRAs. The list goes on, incorporating philanthropy, family offices, advice around marriage and divorce, offshore planning, and so forth. An estate planner who is able to react to market opportunities in that way is likely to have much greater intellectual satisfaction, a much better feeling about themselves, and a bigger bank account. And I believe that those who don’t react in that way are going to be dinosaurs based on the current Washington environment and market pressures.
4. Behaving as an entrepreneur has another advantage in that it leads to giving much greater thought to cross selling with your partners. My own career follows the 80/20 rule: 80% of my clients are straight estate planning clients and represent 20% of my income (actually less these days). But the 20% of clients that represent the 80% of income come from having taken an estate planning client and turning it into a general corporate client who eventually sells the business and starts a charity and gets sued by an unhappy investor and gets divorced, and so on. I could not have succeeded in turning that client from X to 10X without my partners’ participation. And by me bringing in my partners to help grow my clients, they bring me in to help grow theirs. Bigger clients for all means more fees for all. And on another level, no less important, it means deeper client relationships, which feels really good almost all of the time.
5. Although being a technical lawyer alone may not be enough to be successful, that doesn’t change the need to be a good technical lawyer. For an estate planner, that is a lot of work. You need to read the advance sheets and listservs. You need to attend conferences and do lots of reading on your own and attend study groups. You need to be good at research and remembering a lot of rules. If you are bored with the thought of those tasks before even starting, estate planning is not for you. You also need to be a consistent and excellent draftsperson. Clear, precise, internally consistent, direct. Because I don’t have a crystal ball, I also generally believe in drafting for maximum flexibility (for example, providing the ability to take advantage of changing landscapes). And, if you’re not sure how to say something, then say it in plain English. That almost always works.
6. If you don’t know how to answer something and let the client know that, the client will have that much more respect for the things that you do for them. I have yet to have a client be unhappy with “I don’t know, I’ll look into it and get back to you tomorrow” (assuming you get back to them tomorrow). I have also managed to deepen my client trust by bringing in outside counsel in areas where my firm could not do the best job for the client. Which of course means that you have now opened up a whole new referral source. If I bring a labor lawyer in to deal with a union issue for a client, I have every reason to believe that lawyer will bring me in when he recognizes that the owner needs an estate plan or corporate counsel. That proves itself over and over again.
7. I understood early on that if my business development plan was to wait for more senior partners to retire or die, I could be waiting a long time, and by then it might be too late. Part of the reason for this was that when I joined my firm the most senior partner was only 47 years old. I also had a young and growing family, and I was scared to death of not being able to support them. As a general rule I despise the notion of fear as a motivator or reason to do anything. Actions taken out of fear rather than of hope or desire almost always fail. BUT, in this one area of taking care of a family, fear is an amazing motivator. Fear leads to having hundreds of meals with CPAs and trying dozens of networking groups and sitting through God-knows-how-many encounters with bankers and financial managers and insurance agents. And 50 articles and 100 presentations. And charity events. And March Madness events. And. And. And. And, yes, over time you have built a pretty nice book of business. I don’t know any other way to do it. And I still do it today. No, I don’t love the hunt. I like most of the people I meet, but that doesn’t mean it doesn’t become drudgery sometimes. But I do love the kill, and you can’t have the kill without the hunt. You also become more focused over time. I may have met 200 accountants over the years, but if I hadn’t, I wouldn’t know the four or five I can consistently count on today to refer work to me (and to whom I can refer work with confidence). I may have met 100 junior trust officers over the years, but if I hadn’t, I wouldn’t today have the two or three who have achieved senior positions in their banks who can be counted on (with my ongoing attention) to provide fiduciary counsel opportunities. That said, I almost never meet with “cold” referral sources anymore. But I do have excellent young business-development-minded lawyers in my office to whom I can introduce those opportunities or bring to a lunch with one of my longtime resources who will also bring along an up-and-comer from his firm. The senior folks in my firm did that for me, and they have had my undying loyalty ever since. I’d be crazy not to do that for the good young people behind me.
8. A lesson I learned early on from my mentors was that no one is waiting in line to open a door for me. But once I made the effort to open it, there were plenty of good people behind me waiting to push me through. Forcing me to take primary responsibility for my own development was a gift. Knowing I could count on support in those efforts was something I now feel obligated, and thrilled, to share with others. And, obviously, as those young folks bring work in the door, why wouldn’t they look to me to help them develop it further? Plus, assuming I want to practice another 30 years (unlikely, but who knows) I am not aware of any firm that has survived over time without a focused concerted effort to continue to develop its younger lawyers. Developing young talent has another substantial advantage: I can work 2,000 hours all on my own matters, rarely using associates, and make $X. Or, I can work 1,700 hours, use associates to get work done for me, spend the other 300 (or less) developing business, and make $1.5X. The more you develop and leverage younger lawyers, the bigger that multiple will grow.
9. Do not be afraid to share ideas or clients with other estate planning lawyers outside the firm. They will share back and over time become excellent referral sources. If they have a conflict, who better to call than the guy who volunteered an idea or help along the way? In my practice, other than existing clients, other estate planning lawyers have been my best referral sources.
10. We are risk managers. Clients understand risk and reward, and most clients are not looking for risk-free solutions. I think it is essential to ask, what is the risk of taking a particular approach even if that approach may not be on all fours with the technical legal rules? Beyond the fact that next to nothing is risk-free (the client wouldn’t be seeing you if that were the case), risk-free solutions more often than not mean doing nothing. A trust officer wanting to take in a new customer can’t accept that answer. A distributor wanting to set up a warehouse operation in a different state doesn’t want all the reasons why it shouldn’t be done. She wants to know how to get it done intelligently while minimizing the risk. I was told early on in my career that “No” is almost never the right answer. Rather, “No, but” is what a client wants, as in “No, you can’t do it that way, but here is an alternative that carries this and that risk, which practically speaking is only going to arise under the following circumstances.” So much more value added to the client and so much more job satisfaction for the advisor.
11. A corollary is don’t be afraid to be creative in your problem solving. Clients are paying you for your mind. Just because others did it another way, possibly over and over again, doesn’t mean it can’t be done a different way for this client. Be bold. One of my favorite quotes in the world is from Mark Twain: “Loyalty to petrified opinion never broke a chain or freed a human soul.” I endeavor, imperfectly, to lead my life and my law practice that way. That said, an exquisite balance exists between pushing the envelope and not having your client be the test case. Our job is to find that balance, but fear of moving beyond conventional thinking will not help you do that.
12. I tell every young lawyer working for me on their first day on the job to never be a slave to the forms. My firm happens to take pride in having forms that are consistently used from client to client by everyone in the firm practicing estate planning. That results in great quality control. But that doesn’t mean that every form is perfectly drafted. I get really angry with younger lawyers who respond to a question about why they didn’t address an issue they found in the form with, “It was in the form.” Why not just roll over and play dead since you’re not using your brain anyway? Taking ownership, as discussed numerous times elsewhere in this article, should address that. But the other issue with forms, no matter how good ours may be, is that they do not, they cannot, address every client’s unique circumstances, values, and goals. Ninety-five percent of every trust for every client is likely to read about the same, but that other 5% is what adds value to the client relationship and what we are paid for.
13. Do engagement letters. Every time. They protect both the client and you.
14. Do the work. Bill in a timely manner. Collect within a short period of time. That is the fastest way to a successful law practice. If a client isn’t paying within a month or so of receipt of a bill, there is almost always a reason and it’s almost always not good. You are much better off addressing it quickly and head-on. If the bill is too high relative to expectations, be prepared to take the hit. And, if it is because of the client’s actions, let the client know that (hopefully before the bill is sent out), ask them to pay you for the extra work, but be prepared to take the hit anyway if they say no. You should not be afraid to fire a client who isn’t paying. VERY HARD to do. And, I am bad at this and I have paid the price for being bad at this.

Okay. That’s actually 31 things I’ve learned. But that’s because as long as I’m practicing the list can never be static. And this list is hardly exhaustive. These are just the thoughts that came to mind in the few days it took me to put this article together. The list will continue to grow and change over the years, and I’ll get more nods in agreement and more shakes in objection. But I think most of these lessons are tried and true and even with changes in technology and the law are not much different today than 30 years ago or than 30 years from now.