The first time we outsourced our bookkeeping, we hired a woman in Texas. She explained that our books were a mess and promised to “clean them up.”

We knew our books were messy before we hired her, but it was manageable. Our doors were open, payroll was processed smoothly, and the bills were being paid.

But then one day bills stopped getting paid and vendors started calling. Payroll wasn’t submitted on time. Our monthly reports weren’t appearing as expected.

Ms. Texas claimed the clean-up was complicated and time consuming. We’d be happy, she claimed, once she got all the extra work done and things got back on track.

Ugh. Of course I just had to drop out of my accounting class in college. I had asked my professor why debts are on the left and credits are on the right. “That’s just the way it is,” he told me. How would I ever understand something so irrational? I took a sociology class instead.

Let’s face it. Accounting is made-up nonsense. It’s arbitrary, random, and often illogical. But we have to do it.

I had to get the bookkeeping done or face the consequences, so I pushed on with the wacky Texas bookkeeper and hoped for the best.

Step one: Get the bookkeeping technology right

Explainer: we're QuickBooks users. Back when we first outsourced the bookkeeping, we used the server version of QuickBooks.

Before we outsourced to a remote bookkeeper, we moved the data to a QuickBooks hosting service in Seattle. The hosting service kept QuickBooks running for a small group of users.

(We couldn’t use QuickBooks Online back then because the product was new and it lacked features we needed.)

Bookkeeping technology (there are lots of options now) keeps getting better and better. That's good, because the fundamentals of accounting haven't changed.

The interface, reporting, menu systems, and dashboards have all improved. Bookkeeping tools make it easy for dumb lawyers like me to understand the money.

We use QuickBooks Online now. Some lawyers are in love with Xero, which is slick-looking product. TrustBooks has made trust accounting easier.

Accounting doesn't evolve much, so software experts focus on making products friendlier and easier for users.

The first step to outsourcing your bookkeeping is to subscribe to a cloud-based accounting tool.

The idea of having a bookkeeper show up at your office one day a week for a few hours is like something out of a 1990s sitcom where the accountant is the butt of the jokes (Norm, from the show Cheers, was an accountant. Am I the only one who remembers Norm?). It's routine now for bookkeeping to be done remotely.

Which cloud-based accounting software should you use?

Ask your accountant and let them pick. They’ll probably insist on a certain format for your tax returns (eliminating a lot of tax-time frustrations). If that conversation goes poorly, it’s time to upgrade accountants.

Thankfully, my accountant is software agnostic. He doesn’t care which product generates his reports as long as they meet his requirements.

Once you’ve chosen the software product, find a bookkeeper who's competent with that product.

Whatever software you choose needs to be cloud-based and accessible to everyone. You, the bookkeeper, and the accountant all need access.

You'll want to use the tool’s dashboard to stay on top of your numbers. Using a cloud-based product makes it all quick, easy, painless, and inexpensive. You'll get easy access to your data, plus you'll benefit from constant software improvements and backups.

I still talk to lawyers who hesitate to move their accounting to the cloud. These same lawyers often use their iPhone to access all kinds of cloud services. It's all the same cloud.

You're using cloud-based services for your online banking, phone calls, or when you order your medical marijuana delivery.

Loosen …

Every one of us has had a moment when we realized all the time we spent in negotiations was wasted. In retrospect, it should have been clear at the time. “There was never going to be an agreement,” we say to ourselves. “That person was impossible.”

“Know when to hold ‘em, know when to fold ‘em, know when to walk away, and know when to run.”

That’s from Kenny Rogers’ “The Gambler.” Go watch the video. It’s awesome. How do country musicians know so much? I don’t even like country music, but the songs are filled with lessons. But they aren’t the only source of wisdom.

She wants a law practice with a team she can trust to keep clients happy when she’s on vacation.

She wants to be able to take some time off with her spouse.

She’d like to tour Europe, and enjoy two months a year in a vacation home.

But she’s a control freak.

That’s how she describes herself. And she’s right.

Being a control freak has served her well. She built a thriving practice with a bunch of employees that generates a healthy revenue because she’s firmly in control. It’s works for her.

But her control-freak ways mean she has to show up. She’s the one employees turn to when a decision needs to be made. She’s the leader they’ve been trained to follow. Very little happens in her law firm without her input and seal of approval.

Uh oh. This control freak built a business with herself at the center. She’s the star her team orbits. When she takes a day off, the team defers making decisions or calls her on her mobile phone. They can’t move forward without her input.

You’re already seeing the problem, right? The control freak wants time away, but her team needs her presence to get things done. This doesn’t work out well.

Memorandum

To: Control Freaks

From: Lee Rosen

Subject: Freedom

Date: Today

If you’re a control freak, you’ve taught your team to depend on you for decisions and guidance. You can’t get away because you’ve tied yourself to the business like the cement block you wanted to tie to the body of that client you dreamed of dumping into the river.

If your vision for your law firm involves spending more time away, you need to toss your control freak approach into that river as well.

What’s the solution? How does a control freak let go?

If you’re a control freak, letting go is hard. It's fraught with upset and disappointment.

Despite your best efforts, the following will happen:

Instructions will be misinterpreted.

Deadlines will be missed.

The work product will deviate from your approach.

Mistakes will be made.

Clients will be upset.

Money will be wasted.

You will be upset, angry, and ready to give up. You'll believe things would have been done right if they'd been done yourway.

Sounds awesome, right?

But you have to let go if you want opportunities to get away from your business, disconnect, and feel comfortable knowing your team is getting the job done.

Your team needs to make decisions without you. If they can't decide, you can't leave. You can be present and make the decisions, or you can be absent and accept that they will sometimes fail to meet your standards.

The list above may have made you even more resistant to letting go. I feel your pain. Those concerns reinforce your desire to hold on tightly, stay in the center, and remain in control. After all, it’s your name and business on the line.

First, a reality check

Most of my control freak friends live in a fantasy world where they only remember the things that went well. When they’re in control, they tend to rate their team’s work highly. They see happy clients, an excellent work product, and deadlines being met.

Control freaks are great at seeing their outcomes through rose-colored glasses.

The reality is quite different.

Control freaks do their best to only see the things that go well. They ignore the mistakes, blown deadlines, upset clients, uncollected fees, high turnover, and arguments with their employees.

They blame mistakes on their employees, even though they tightly control the environment in which the employee operates.

Take off the rose-colored glasses. Welcome to the real world.

Things don’t go nearly as well for control freaks as their imagined, well-controlled fantasies lead them to believe.

I’m not saying control freaks screw up more often than other law firm owners, but they certainly don’t screw up less. Things can go badly in any law fir…

Tourists in India feel like dollar signs. Touts crowd around, shouting above the street noise, imploring tourists to buy whatever they’re selling. Feeling like a dollar sign is never a good thing. Tourists don’t like it. They feel less like humans and more like objects. As buyers, we turn into non-buyers quickly when the pressure cranks up.

Whenever I browse the web from this Airbnb in Bangkok, a message pops up on my screen.

“Your AIS Fibre Internet due date has passed. To check your balance and due date, please log on to your ‘my AIS’ app.”

Apparently my landlord isn’t paying his bills on time. Unfortunately, his current financial situation may impact his future financial situation. The same could happen to you.

The apartment is supposed to include access to the Internet and a pool. (The pool has been out of service since we got here. Please don’t mention the pool situation to my wife. It takes her 15 minutes to calm down.) The Internet is far more important to me than the pool (but keep that between us).

One day during our first week here, the Internet shut off for four hours. The owner paid the bill and the service was restored a short while later, but the interruption was disconcerting.

I suppose his bill-paying habits are irrelevant to our stay in his apartment, but this message popping up on my screen makes me wonder about his financial stability.

Knowing that our landlord is behind on his bills undermines our confidence in him. Does he forget to pay? Maybe his finances are a mess? Should we be concerned about anything else beyond the Internet?

Let’s face it: How you manage your money says a lot about you. It’s a common measuring stick, an important way we judge one another. It’s how we determine whether to trust someone to meet their obligations--financial or otherwise.

When we fail to pay our bills on time, people notice. They talk about us behind our backs, wondering about our situation.

Sometimes the reason we’re behind on our bills isn’t because we’re out of cash. There are many plausible explanations for a delinquent account, but failure to pay still makes people wonder.

They lose confidence in us. They gossip, which erodes trust.

Whether you’ve got $10 in your bank account or $10,000,000, you should behave in a way that shows financial responsibility. People won’t talk about the amount of cash you have, but they will talk about how you demonstrate maturity, reliability and trustworthiness.

People notice financial lapses. Don’t think we’re all too absorbed with our own issues to notice your struggles. We notice because it’s part of how we make judgements in a modern society.

The world changes quickly and our trust indicators evolve, but we still need to determine who to trust. Maybe something will replace human judgement at some point, but for now, we judge each other all day long.

I'm not a fan of worrying about other people’s thoughts. I try not to let their judgments drive my behavior. But trust is the currency of the legal profession. When you lose the trust of others, you're lost.

Money, too, is all about trust. There's no way people will trust you if you don't live up to your financial promises.

Money, trust, and your reputation are all bound together and that's not likely to change anytime soon.

Law firm partners judge their associates

I had two associates who clearly couldn’t manage their money. Both of them made me very nervous given that their work role required me to trust them to handle financial issues on behalf of our clients.

I never fully trusted either of them and they were never given responsibility without extra oversight.

How did I know they were financially out of control? The clues were obvious because our financial situations tend to leak out in different ways.

The fastest way people make it obvious they have a financial problem is when they panic about their paycheck.

Our firm deposits paychecks on the 5th and the 20th of each month. Usually the cash hits our employees’ accounts a couple days before. The funds for the 5th sometimes show up on the 4th or 3rd. Depending on weekends and/or holidays, the money might arrive earlier.

S…

In retrospect, outsourcing worked out pretty well for my law firm. Of course, it would have been much easier if I had known what I was doing at the time (which is why we recently created a course on outsourcing – so you can do it without all my challenges). When I started my firm, I had no idea how hard it would be to get employees to do what I needed. Getting results from other humans is difficult. It will never be easy. As the leader of your business, your goal is to get work done through others. You’ll have to go down one of three paths with your team…

In retrospect, outsourcing worked out pretty well for my law firm.

Of course, it would have been much easier if I had known what I was doing at the time (which is why we recently created a course on outsourcing – so you can do it without all my challenges).

When I started my firm, I had no idea how hard it would be to get employees to do what I needed. Getting results from other humans is difficult. It will never be easy.

As the leader of your business, your goal is to get work done through others. You’ll have to go down one of three paths with your team…

1. Managing

Most lawyers choose to assemble and manage a small team of lawyers. It can get ugly. Fast.

Managing people is hard. They don’t teach it in law school (or any other professional school, for that matter). From what I can tell, it’s barely taught in business school.

Management is mostly learned along the way. Many businesses plod along without good management, which is why we’re often frustrated by the purchases we make, the poor service we receive, and the attitudes of people who service our accounts.

For the same reason, we’re excited when we come across a business that does things right, on time, and as-promised.

Management is a never-ending headache. You never get to stop. It never gets easy. But it’s an essential part of getting results for discriminating clients.

The minute you stop managing your team, it will lose its edge and outcomes will suffer. You need endless patience, resilience, and persistence.

Lawyers who commit to managing a team have to learn as they go. In addition to practicing law, they need to become excellent people managers. Being able to lead a team is an incredibly valuable skill.

2. Outsourcing

An alternative to managing a team is to assemble autonomous service providers on an ad hoc basis.  Today’s technology and marketplaces make this approach easier and more accessible than ever.

You can staff a big project quickly with experienced experts and let them collaborate to reach a successful outcome. Instead of hiring generalists, you can hire specialists experienced in whatever challenge you face at the moment.

You can find excellent vendors to help you run the firm and handle client work. You might hire vendors to help with human resources, financial management, information technology, and marketing projects.

You might hire other lawyers to help with a particular legal problem or specialists adept at assisting lawyers with a particular problem.

If you commit to outsourcing, you’ll become an expert at sizing up new team members, organizing and managing their work, supporting them, and driving them forward.

You’ll become an excellent project manager. Being able to manage the disparate parts of an ad hoc team is also an incredibly valuable skill.

3. A hybrid approach

Most of us find we can’t hire in-house people for every role because the role is too small or it requires specialized (expensive) expertise. We can’t solve every problem internally, so we outsource some things.

At a minimum, most law firms outsource some accounting, information technology, and marketing. You might outsource more, but you’ll probably find yourself mired in a soupy mix of managing people, dealing with outsourcers (and their assignments), and coping with clients.

The hybrid approach leaves us in an awkward middle space without expertise in either management or outsourcing. We become semi-adequate people managers and semi-adequate project managers.

When we dabble on both ends of the spectrum, it can be difficult to gain clarity regarding the best techniques and tactics for each arrangement. We struggle with hiring and managing in-house positions, as well as using online marketplaces to assemble effective teams.

Unfortunately, those of us who take the hybrid approach typi…

There are lots of differences between us lawyers. We’re each unique in our own way. We have different strengths and weaknesses. We have a broad range of interests. We spend our time differently. We’re a diverse bunch of folks. But we’re a lot alike, too. We have many things in common, like education, that create a lot of similarities. But we also have some (counterproductive) things in common that hurt our practices, reduce our income, and make us unhappy. After working in the legal field for three decades, here are some things I’ve noticed about lawyers.

Hotels, like law firms, make promises to their prospective clients.

Those promises aren’t always articulated. Often, they’re implicit. It wasn’t until the first time I checked into a hotel room without a window that it occurred to me that "windows" were optional.

Your clients probably have their own beliefs about what's included in their representation, whether or not you say it.

One time, Lisa and I walked into a hotel room to find a shit stain on the white comforter. I’m serious--it was shit. I gave it the sniff test.

Every hotel needs to hit a threshold of basic acceptability: No bed bugs, blood stains, or horrific smells.

Beyond the deal-breakers, each guest has their own list of concerns. For instance, most of us want our hotel rooms to be safe, sanitary and smell nice. Those requirements convince us to put down our luggage and take a look around, but we still don’t commit to staying in the room.

Before we unpack our bags, we check a few more things. (Personally, I have a list of things I check before I'm willing to settle in.) If the hotel breaks one of those implicit promises, I’ll complain. Sometimes I’ll tolerate the revised promise. Other times I roll my bag down the block to the next place.

Each customer has a slightly different list of secondary priorities, and some willingness to deviate from their list. Everyone has different ideas of what’s critical (like those rock stars who demand a certain color M&M in their dressing room).

I call my personal list the “Holy Hotel Trinity.” Of course, it’s just my list. Yours (and your customers') will be different.

The Holy Hotel Trinity

The Holy Hotel Trinity reflects my priorities, though I've met lots of other travelers with similar concerns.

If the hotel doesn’t satisfy my list, I won’t necessarily walk right out, but it might cause me to write something nasty on TripAdvisor. Or complain. Repeatedly.

Once a hotel fails to meet my expectations, I start to see everything through a filter of disappointment. I’ll walk into the breakfast buffet with a more refined palate. I won’t tolerate a room service delay. And I’ll be far more likely to freak out when the hot tub is perpetually “undergoing maintenance” for my entire stay.

These are my Holy Hotel Trinity priorities.

1. Internet

We say we go on trips to “disconnect,” but we all know that’s bullshit.

Even hotels in rural Cambodia offer WiFi. “Here’s your complimentary welcome drink, a cool face towel, and the WiFi password,” said the young manager. I bowed in response to his bow.

Listen, you give me great WiFi and I'll give you a prayer-hands gesture all day long. I need the Internet as much as I need oxygen and Diet Coke.

2. Air conditioning

I’m not happy if the AC doesn’t work. (That’s also true of the heat, if we've make the mistake of going skiing or something when we could go to a tropical island.)

I like my temperature controlled. Like a lot of people, I have romantic notions about opening the balcony door and letting the cool ocean breeze blow through, but I quickly lock that door and turn on the AC. There might be mosquitos or lizards or something out there, so I'm going to crank the temperature down and sleep under the comforter.

3. Hot water

“There’s nothing like a cold shower on a steamy tropical island,” said no one, ever.

It can be boiling outside, but I still want my shower to be nice and warm. Cold water is a shock to my system, and I want a shock to my system from the shower about as much as I want it from the loose wire poking out of the electrical outlet: not at all.

I’ve learned the hard way to let the water run for a minute or two to see if it gets hot before I unpack.

These three items are my essential list. These are the things I care about beyond the apparent deal-breakers.

I'm a little picky, but not very…

Marketing is important. Having a plan is essential. Sticking to that plan can make the difference between success and failure. But plans get complicated. Complexity is the enemy of execution and the cause of much of our procrastination. When things become challenging, we put them on the back burner. If you execute this plan, you’ll build your practice. It’ll grow steadily. It’ll become more profitable.