Radical Approach for Control Freaks Seeking Freedom

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.

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 your way.

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.

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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 firm. Being a control freak doesn’t magically prevent breakdowns.

As much as we might deny it to ourselves, we screw up. We make mistakes.

Even when we run every piece of a process, we still end up with errors because we’re human.

Even with firm control, we can’t eliminate all mistakes. We simply screw up sometimes.

Yes, when we learn to let go, screw-ups will happen. But they would have happened anyway. When you let go, someone else on the team will do the screwing up.

We may see our team’s mistakes differently than we would see our own, but it’s all the same to a client. A mistake is a mistake. It doesn’t matter who made it.

Delegation is the path forward

If you’re a control freak, you need to delegate some of your decision making. You need to let go and coach others to step forward.

Let associates make case decisions.

Let the office manager make hiring decisions.

Let the bookkeeper handle the money.

And stop keeping the firm’s metrics secret!

You need to let others do the work and make whatever decisions are necessary along the way.

You might hesitate because you know your team will make mistakes. You’re right.

You need to find a way to delegate in a comfortable and reassuring manner. You need to let go without pushing your own control-freak buttons because that will tempt you to jump right back in when things get messy and/or you get nervous.

You have a strong track record of delegation

Letting go is easier than you imagine. I say that because you probably have a history of successfully delegating, even though you don’t see it that way.

You delegate all of the time:

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  • You delegate the management of your office space when you rent
  • You delegate to a real estate broker when you need to find office space
  • You delegate to night-time cleaning services
  • You delegate the maintenance of the office building
  • You delegate the delivery of your email
  • You delegate package delivery
  • You delegate the preparation of deposition transcripts
  • You delegate phone service management
  • You delegate to an accountant for your taxes
  • You delegate to a coffee service to keep you fueled
  • You delegate to a printer for business cards
  • You delegate to a technology firm for computer service
  • You delegate to a bank for, you know, banking
  • You delegate to court reporters for testimony transcription
  • You delegate to airlines and pilots to get you around

You might even go further:

  • You delegate marketing services and website maintenance
  • You delegate to copy shops for paper copies
  • You delegate to scanning services to scan paper
  • You delegate to exhibit vendors to make exhibits for court
  • You delegate to temporary agencies to hire a temporary assistant
  • You delegate to recruiting firms to hire associates
  • You delegate to facilitators to run your firm retreat
  • You delegate to restaurants to cook your lunch

You get the idea.

As much as you might believe you’re a diehard control freak, the truth is that you delegate constantly.

Someone dry cleans your suit, fixes your car, cleans your house, and provides you with clean water and sewer services. Someone probably mows your law. You even let someone clean your teeth and examine your wrinkly body parts.

These are your control-freak triggers

As you can see, you’re already a delegator. You’re only a control freak when…

  1. You think you know more than others,
  2. You’re in close proximity to the work, and
  3. You believe you can do it better.

Unfortunately, if those three triggers happen often enough, they’ll keep you from your vision of spending time away from the business (or working on the business instead of handling the day-to-day operations).

You’ve got to break the pattern by disrupting one of those three control-freak triggers.

Unfortunately, the first trigger (“you think you know more than others”) is the hardest to change.

Personally, I often think I know more than others. I’m often wrong, but that doesn’t slow me down.

The same is true of my belief that I can do it better than others (the third trigger). Again, I’m often wrong, but I rarely let reality get in the way.

We’re pretty good at letting go when the distance increases. Many of us believe we know more than our accountant, but we’re willing to stay out of the mix because the accountant is across town.

I suspect that if we were allowed to sit and watch as our accountant prepared our tax return, we’d offer all sorts of suggestions and ideas. Proximity makes a big difference.

So if you’re a control freak, attack your tendencies with an assault on “close proximity.” If you distance yourself from the work, you’ll slowly condition yourself to become comfortable letting go.

Radical 5 step delegation plan for control freaks

When you delegate to someone who’s physically far away from you, it goes by another term:


Outsourcing is nearly the same as delegation, but it doesn’t push your control freak triggers quite as hard. It’s a gateway drug that encourages you to let go. If you start outsourcing, you’ll experience a high when you don’t have to do things yourself.

You’ll persuade yourself to step back and put even more distance between yourself and your team. You’ll let people do the work you’ve trained them to do. You’ll let them make their own decisions, which fosters more learning and growth so they do an even better job for your clients and your firm.

Suddenly your vision of more time away is within sight.

Here’s your 5 step plan for making delegation via outsourcing work in your law firm.

1. Reduce your resistance

Put some distance between you and the work. Outsource it to someone far away. That’ll reduce the likelihood of tripping your control-freak triggers.

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Think of it like you think of your tax return. Ship the work off and let someone else do it.

Find someone in Ukraine to build your website.

Find someone in Delhi to do your billing.

Find someone in the Philippines to do filing.

Find someone in Cape Town to handle document review.

Use our outsourcing course to help you organize and outsource the work. Use websites like Indeed and Freelancer to find qualified professionals.

Put some distance (and time zones!) between you and your work so you can’t easily retake control.

2. Reduce team resistance

Expect some pushback from your team.

Outsourcing work (especially the work they handle daily) feels like a threat. Change is hard, even if they complain about you or the work. They’ll reinforce your hesitation to outsource by helping you find a rationale to turn back.

Over time, their resistance will wane. Outsourcing feels different than delegating the same work internally. Sell it as an opportunity to lighten the load. You need your team onboard, or it’ll all go poorly.

Get them to buy in by having them help you locate outsourcers, vendors and firms to handle the work. Have them develop specifications for the work and systems for managing it all.

As with all approaches to getting work done, there will be mistakes.

When mistakes happen, you want your team to react by helping you solve the problem that caused the mistake. You don’t want them to push you to bring the work back in-house.

You’ll only become better at delegating if you shift the culture toward your team solving their own problems.

3. Take baby steps

Change is hard. When you start letting go and outsourcing more work, you’ll find resistance in yourself and your team.

There will be a long list of reasons to turn back to your control freak ways. But your vision requires letting go and this approach of putting physical distance between yourself and the work has worked before, so it’ll work again.

Take small steps at first. Outsource one thing at a time. Get it to work. Like anything new it’ll take some tweaking and optimizing.

Instead of fully outsourcing your calendar management, get some help from a virtual assistant to set up certain events. Take baby steps as you build comfort. Don’t push yourself too hard.

Your resistance will diminish as you move forward. Control freaks aren’t good at letting go, so you have to move slowly.

Keep your eye on the vision you’ve created for your role in the law firm. Delegation is essential to that vision. Outsourcing is the path of least resistance in your quest to comfortably delegate your day-to-day activities. You want your team to work without turning to you for answers.

4. Systematize it

Outsourcing forces you to develop systems.

These systems look different than the ones you created for internal work. They’re more about preparing the necessary information to hand off and monitor the status of the work, and less about the step-by-step process of doing the work.

Systems for outsourcing are easier to create. For example, it’s easier to develop a system for sending the right information to the accountant to prepare the tax return than it is to develop a system for actually preparing the tax return.

Documenting systems for outsourced work is critical to the success of the outsourcing, but since the systems are simpler, you’re more likely to do it. Developing a culture which creates systems is critical to achieving your vision of being less involved in the moment-by-moment decision making.

Use the outsourcing process as an opportunity to shift the culture of your team toward documenting systems. The team will learn that systems are valuable, since they won’t be able to turn to you to solve every problem, make every decision, and fix every issue.

5. Watch yourself grow

Take note of your progress as you delegate through outsourcing.

Keep in mind that you’re using outsourcing as a gateway to better delegate to your internal team. You’re putting physical distance between you and the work to make this easier for you.

You’re taking baby steps, but it only helps if you learn from the experience and help your team learn along the way.

Give yourself some time to grow into letting go. Give yourself a chance to absorb and internalize the benefits of letting go.

You didn’t become a control freak overnight and you won’t reverse course quickly either. You’ll be tempted to backslide when you discover errors and discrepancies or suffer disappointments.

It’s hard to let go. It’s easy to take it all back under your control, but you must resist.

Keep a close eye on your progress as you let go. Celebrate the victories so you can start to see yourself less as a control freak and more as a master delegator. It’ll happen if you follow the 5-step plan.

Use what you learn about yourself

Outsourcing will encourage better delegation behavior within your team. You’ll get more comfortable letting go and they’ll get more comfortable making decisions without your input.

Trust will develop on both sides. The team will also see the benefits of outsourcing.

As you grow, push yourself further. You’ll find you can delegate even more: phone answering to a receptionist service; human resources to a professional employer organization; client surveys to a professional; bookkeeping to a service; brief drafting, legal research, and more to lawyer contractors.

You might become an outsourcing addict, outsource it all, and find yourself managing a small team of project managers who supervise the outside vendors. That’s not a common approach among law firms, but it has an appeal.

Keep letting go and you’ll move closer to your vision of having time away from the business, maybe for vacation or family time–or maybe for putting more of your mental energy to work on the business instead of in the business.

If you’ve created a culture and process that can’t function without your presence, change is more difficult than making a simple decision. You didn’t arrive at this point by accident.

You need to change your perspective and give yourself time to get comfortable doing things differently. You need to grow into a new role, in which you communicate your vision to your team and support them to get it done.

Abandoning your control-freak approach is a big change. The plan above will get you moving in the right direction.

Transitioning from control freak to delegator isn’t easy, but it’s worth it for the chance to go away on vacation and trust others to make decisions without your input.

Transitioning to a delegator may be the only way to achieve your vision.

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