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The Dreaded Drive-By Delegator

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How reframing handoffs exponentially expands your firm’s capabilities.

In my law firm, I was known as the “dreaded drive-by delegator.”

Passing an associate’s office I barked, “Restate the Johnson file trust with a scenario six, review the prior trust to find whom to name as the successor trustee and see me when you’re done.” Rat a tat.

On my way down the hall to a client conference room I told my paralegal to “Make sure you call the Smiths to ask them about that problem we had about transferring their residence into the QPRT, and get their answer.” Rat a tat tat.

Tossing a stack of documents on my legal assistant’s desk, I asked to “Please create a transmittal letter to Hank and Tammy, listing all of the documents in this pile.” Rat a tat tat tat tat.

And so it went. I’m not one to shy away from delegation as many other professionals tend to be. Yet my handoffs didn’t provide enough direction, often resulting in misunderstandings that required repair. My frustration1 showed when mistakes were made, but those mistakes were my fault. How could I expect someone to read my mind? It’s a wonder everyone didn’t walk out on me.

I’ve since learned about the five levels of delegation. If you’re being clear to yourself as well as to the delegatee, voicing one’s expectations greatly enhances the outcome. Further, great delegation creates an even higher output and fosters collaboration, which leads to increasing personal and firm capabilities. More on that below.

Before examining the five levels of delegation, it’s important to identify why effective delegation isn’t common. As I mentioned, many professionals, attorneys leading the charge, shy away from delegation. They try to do everything themselves. That person I refer to as . . .

A Rugged Individualist

I’ve noticed that many estate-planning professionals are “rugged individualists.” They don’t trust others to take on tasks. It’s no wonder that so many of us have this attitude because the American school system promotes rugged individualism. In school, when you collaborate with other students on projects or test answers, it’s called cheating. Our system wasn’t made to instruct via group effort, in which individual strengths are maximized, creating something larger than any individual could accomplish on their own.

It therefore follows that once we graduate, we maintain this attitude into the workplace. Early in your career, for example, it was all on you, wasn’t it? You may not have had an adequate support team, so you worked late into the night. You learned to work efficiently. That’s what led to your success. Even better, every task was performed to your high standards.

But at some point, your practice grew. You felt like the guy on the Ed Sullivan Show spinning plates.2 Yes, I’m old enough to remember Ed Sullivan. He’s the variety show host who brought the Beatles to an  American audience.3 You doknow who the Beatles are, right?

But there are only so many tasks you can handle. Eventually, you grow weary and burn out.4 So you want to offload tasks, yet it’s not intuitive to do so, nor do you understand effective methods to achieve success.

I’ve spent the better part of two decades coaxing one of my law partners to hand off tasks that aren’t within his highest and best use. When you’re consistently performing tasks that should be handled by someone else, you’re eroding your firm’s productivity and profits. You hit a ceiling that you can’t break through unless you work harder and longer.

Why do so many of us refrain from delegation?

Four Lame Excuses

The four most common (lame) excuses I hear from estate planners about why they don’t delegate are:

  • “I don’t have anyone to delegate to.”
  • “I can do it faster myself.”
  • “In the time that it takes me to teach someone, I’ll have it done.”
  • “They won’t do it right.” (I translate this to “the way I would do it.”)

If you find yourself regularly uttering any of those phrases, it’s safe to label you a “rugged individualist.” Let’s examine each excuse.

I don’t have anyone to delegate to. Then hire someone. Seriously!

The corollary argument is, “I can’t afford to hire someone.” Like Cher’s Loretta Castorini does to Nicholas Cage’s Ronny Cammareri in the 1987 movie, Moonstruck,5 I feel like slapping the person, exclaiming, “Snap out of it!”

Why can’t you afford to hire someone? I have a couple of theories. You haven’t freed up the time it takes to prioritize your unique capabilities. How much more revenue would you generate if you spent more time with your most important clients, schmoozed your referral sources or created educational material on your website?

The second is that you harbor a scarcity mindset, as opposed to an abundance mindset.6 A scarcity mindset is one in which you fear that you won’t make payroll or there won’t be enough work to justify a new team member. When I hired Michael Hill as a young associate, I wasn’t sure that there’d be adequate work to keep him busy. He ended up working late hours just to keep his head above water, requiring us to hire more people. Shortly thereafter, he made partner.

Our minds are biologically programmed to watch out for and to expect danger. It dates back to early human existence when survival instincts were essential. The scarcity mindset feeds into our primal brain—hiring someone won’t work—is doomed to fail—the only person you can rely on is yourself. These thoughts are what the human mind naturally defaults to.

It’s not easy to develop an abundance mindset. It goes against the grain. Those who realize life is rarely a zero-sum game seem to find themselves atop the pyramid. Have you ever noticed that successful people seem to easily compound wins? I no longer worry whether hiring for a new position is necessary. I just know when we need it. Once you hire the right individual, the one thereafter becomes easier. If you find yourself unable to delegate to your existing staff whose numbers you feel should be adequate, you may have misfits that don’t belong in your firm. Here, multiplication by subtraction might work wonders.7

I can do it faster myself. Probably true. So what? I’m a faster typist than most of my staff. Should I therefore type my own letters? Estate-planning drafts? White papers?

Hopefully, you’re thinking, “no, of course not.” Why not? “Because it would be a waste of your valuable time and not your highest and best use to create more profits for your firm.”

Exactly!

When you hoard tasks, you’re not letting your team grow. Expect mistakes. They’ll happen. But it’s part of the learning process.

In the time that it takes me to teach someone . . .
This falls under the same rationale as the previous one. Let’s suppose that it takes you 30 minutes to explain how to accomplish a task that you can probably knock out in five minutes. You then take the time to instruct. Let’s also presume that you must teach this task over two more times on separate occasions for the same type of task before the lesson is learned, but the successive lessons are only 20 minutes, then 10 minutes. You therefore took an hour to teach someone a task that was performed three times. Those three tasks would have only taken you 15 minutes had you not taken the additional 45 minutes to instruct a team member.

Because you did take the time to oversee and instruct, however, you don’t have to do that task. Ever. Again. Someone else knows how to do it. Is that worth the extra 45 minutes that you spent? Absolutely!

They won’t do it correctly. Well, most of the time this translates to—they won’t do it the way you would do it.Does that mean it’s wrong? It might be, at first. If your student doesn’t learn the lesson plan, then perhaps you have the wrong student. See multiplication by subtraction.8

Assuming, however, that you’ve made a good choice with your delegatee, let them do their job. Nurture them to expand their own capabilities, which in turn, expands your firm’s capabilities.

What this speaks to, however, is a broader question. Aside from the lame excuses not to delegate, what are true obstacles to delegation? I can cite two. First, it doesn’t truly free you from the task when you must still supervise and review. You don’t want an embarrassing mistake to go out to a client.

Second, unlike my terrible drive-by delegations, to offload effectively, both sides must understand the expectations going into the project. Here’s where five delegation levels come in.

Five Delegation Levels

An approach to ensure that both you and your delegatee understand the level of responsibility for a project is to incorporate one of these five delegation levels. With each level, the amount of responsibility shifts from the delegator to the delegatee. Moving up the ladder requires increasing delegatee competency on their part and faith in your support team on your part.

As demonstrated above, rugged individualists don’t like letting go.9 Rugged individualists might find it easier, however, when they believe that the delegatee is aware of shifting responsibilities.

Level 1: Do exactly as I ask. When dictating correspondence, one of my now-retired law partners would begin, “letter to Mr. John Smith at 123 Main Street, Fort Myers, Florida 33901. Dear John…” The opposite of this might be how I may dictate a cover letter: “transmittal letter to John Smith…,” fully expecting my assistant to review the file to determine the address and base content.

Step-by-step, detailed instructions are required for Level 1 delegation. It leaves most of the work on the individual delegating and very little responsibility on the delegatee. A wrong address, for example, would have been my law partner’s fault and not their staff because the staff member was expected to follow their explicit instructions.

I make it known that Level 1 delegation isn’t what I’m looking for from my team and never to assume that my expectations are for this level.

Level 2: Gather information and let’s discuss. The next level imposes more responsibility on the delegatee because I’m asking them to gather information necessary to make an informed decision. Here the project itself may be somewhat ambiguous, and you wish to maintain ultimate decision-making authority. An example is when I instruct my associate attorney to research a tax issue that affects a client’s estate plan. We’re both in learning mode, and I want to discuss my associate’s findings, using their analysis and my experience.

Level 3: Make a recommendation—I’ll decide. The difference between Levels 2 and 3 is the expectation that your delegatee will ultimately make a recommendation. You’re looking for them to review, analyze and arrive at a conclusion that should be satisfactory to you, yet you remain responsible for the ultimate decision and its consequences.

Having a human resource professional review the firm’s health insurance benefit plans for next year illustrates this level. While I don’t want to spend the time necessary to sift through the available options to compare benefits, I appreciate someone whom I trust to do so, narrow the choices down to one or two within our budget constraints and then let me or my team of partners make the ultimate decision.

Level 4: Make a decision—I trust your judgment. Level 4 brings us to a much higher expectation for the delegatee. The delegator must have confidence and faith in the delegatee to make a good decision. The delegatee must also have confidence that they can successfully navigate and complete the task. You’re completely handing off the issue.

It’s important to incorporate strategies such as ensuring you’re available for questions; not underestimating the amount of time necessary to complete the project will provide confidence. While Level 4 may feel unnatural to the rugged individualist, and consequently feel riskier, it also provides a higher benefit by freeing up the delegator to work on projects that are higher level and better uses of time.

Level 5: Make whatever decision you like best, and implement that decision. Here the delegator washes their hands of the task. Rather than delegation, I view Level 4 and especially Level 5 as collaboration. Collaboration is when two or more individuals create something together that neither can create on their own.

For example, when building my firm’s estate-planning website,10 I became frustrated11 with expensive marketing firms that didn’t understand my law practice and took too long to create structures and post my material.12 I therefore hired in-house graphics, web design and social media experts.13 I don’t know how they do their work, nor do I care. I tell them what I want, give them the copy or media and let them do their thing.

I’m working in my highest and best use as I love to create educational materials and media. I’m offloading how it’s programmed onto my firm’s website or social media platforms. They also work on my consulting firm’s website14 that provides estate-planning attorneys practice development advice.

My team takes one idea that I may have and turns it into webinars, blogs, podcast episodes and articles.15 They’re now in the process of creating online instruction modules. There’s no way that I could create this without others who possess skills vastly different than my own. Level 5 delegation morphs into collaboration, thereby creating new capabilities.

Increasing the Firm’s Capabilities

When you collaborate, you’re increasing your firm’s capabilities. If I hung onto every task and decision affecting my firm, my firm’s ceiling would be my ceiling. It would limit the services we provide to our clients, how quickly and efficiently we can provide those services and their quality.

As another example, we have two asset alignment specialist team members.16 Their job is to help our clients fund their trusts, make beneficiary designations and transfer assets to accomplish their estate-planning goals. While I have a general understanding of the software they use, it would take me vast amounts of time to perform the services they provide for our clients. Instead, the attorneys in our firm direct these asset alignment paralegals on how we want a particular client’s assets held, and they do their work.

I don’t need to know how they do what they do. I just need to take a moment to review their work product to determine if it was completed correctly. When you’re looking for a “who” to do the work rather than “how” to do the work, you’re at the highest levels of delegation and collaboration.17

Annoyances Become Capabilities

In the early years of my law practice, my team consisted of me and one paralegal. Dorothy and I did everything. Estate planning. Probate. Trust administration. The works.

It was exhausting.

It got so bad that I almost quit the practice of law. “Surely there’s some easier way for me to earn the same amount of money,” I thought. Truthfully, I was right if I were to continue that path. Certain tasks became annoying to both Dorothy and me. As my practice grew, she became despondent at the number of telephone calls that she had to handle with each probate file.

“You realize there might be a surviving spouse, adult children beneficiaries, CPAs, investment advisors and appraisers all calling me on one file?” Dorothy complained. “How am I supposed to get my other work done?”

Her annoyance became a new capability when I hired a second paralegal just to handle probates. This enabled us to handle more volume. As I became frustrated trying to do too many things, I hired another attorney and more paralegals to offload more tasks.

Rather than delegating at Levels 1 or 2, most of my delegations are at Level 3 or higher. This results in my decreasing day-to-day involvement in the actual “how” of the tasks that I delegate. Today, I wouldn’t know how to instruct most of those tasks. Even now, we conduct production meetings to determine what automation and artificial intelligence capabilities might enhance our work product—making it faster, easier and cheaper to produce with better client results.

The attorneys I hired and eventually made partner also had different capabilities than me. With each annoyance that I confronted, our firm’s capabilities grew. And we continue to this day. If I try to do things outside my own unique set of capabilities, my team tells me to “stay in your lane.”

My goal isn’t to do more. It’s to do less. I want to operate within a very limited zone of tasks and projects that I enjoy while adding value to my firm and the clients we serve. As I enter my 34th year of practicing law, I find that I don’t enjoy some things that I once did. But with delegation and collaboration, I discover new, exhilarating projects that take my firm to an ever-higher level of service and client satisfaction.

Bottom Line

The result of using the five levels of delegation is to create freedoms for you and your team. Growth is only possible by allowing others to learn, make the occasional mistake and shoulder more responsibility. The best way to accomplish continued growth is to set clear expectations while determining each team member’s highest and best value using their unique capabilities. When everyone uses their capabilities, the firm’s capabilities expand, and client satisfaction grows.

Endnotes

1. In my worst moments, I’d raise my voice and/or slam papers down on my desk. I learned this isn’t how one exhibits good leadership skills.

2. www.youtube.com/watch?v=Cb6NS_F5xTE.

3. www.youtube.com/watch?v=jenWdylTtzs.

4. Bloomberg Law reports that 52% of lawyers felt burned out in Q4 of 2021, https://news.bloomberglaw.com/bloomberg-law-analysis/analysis-attorney-well-being-declines-with-burnout-on-the-rise.

5. www.youtube.com/watch?v=iLgMFwStTHc.

6. https://resources.strategiccoach.com/the-multiplier-mindset-blog/scarcity-vs-abundance.

7. See Shannon Waller with Janye Stymiest,Multiplication by Subtraction (The Strategic Coach Inc. 2019).

8. Ibid.

9. https://resources.strategiccoach.com/the-multiplier-mindset-blog/don-t-be-a-rugged-individualist-delegate.

10. https://floridaestateplanning.com/.

11. But thankfully, I progressed to the point of not throwing tantrums.

12. Is there any other type?

13. Imagine going from a state of caution when hiring another attorney or paralegal to hiring individuals totally unrelated to the law practice because you wanted those capabilities inside of your firm. That’s why I posit that it’s a lame excuse for a professional to complain they can’t hire someone they need.

14. https://4freedompractice.com/.

15. https://4freedompractice.com/learning-center/.

16. https://floridaestateplanning.com/assetalignment.

17. A great book on the subject is Dan Sullivan and Dr. Benjamin Hardy, Who Not How (Hay House 2020).


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