Master Class: Achieve a 3-Day Workweek Through Delegation


A three day workweek? You might be thinking, that's too good to be true. But through the power of automation, outsourcing, and delegation, you can actually achieve the work-life balance you've been dreaming of.

In a webinar recorded on May 26th, 2020, Maddy Martin, head of growth and education at, was joined Jordan Ostroff, managing partner of JordanLaw, to discuss how business professionals from all industries can delegate the majority of their most annoying tasks, like appointment scheduling, and cut their workload in half so they can enjoy an ideal workweek. From understanding your role and identifying tasks for delegation to properly addressing your workload demands and prioritizing your projects, Maddy and Jordan list the steps you can work through to give yourself the gift of a lighter workload and a much easier workweek.

We've provided a full transcript of the video below, edited for readability, so you can read all about how you can delegate your most time-consuming tasks to lessen your workload and achieve an efficient workweek that gives you more time off. You can watch the full webinar by clicking on the video below. This webinar is also available to watch for free on YouTube. To watch more videos like this one, with tons of free tips for soloprenuers, small business owners, and more, subscribe to our YouTube channel!


Maddy Martin

Head of Growth and

Education at


Jordan Ostroff

Managing Partner at




Welcome everyone.

Thank you for joining us and a very warm welcome to Jordan Ostroff, who has become a really great acquaintance and friend over the last several months. We've had so many good conversations. I'm thrilled to have you here today. He is the owner of Jordan Law and LegalEase Marketing based out of Florida.

Just a quick introduction: I'm Maddy Martin, head of growth and education for

We host a lot of talks around running a better business because we facilitate virtual receptionists for calls, chats, and texts, too. I'm very happy to announce that we're 24/7, which helps with the responsiveness that we offer for a great deal of businesses in all practice areas, especially at this time.

We're recording this during COVID. When the hours and days blend together, people are looking for any opportunity to reach out to both marketing agencies and law firms and many other businesses just when they have the opportunity.

So, Jordan, welcome. Can you just share a brief bio of yourself and then we'll get into the topic today which is all about delegating down to a three day work week?


Sure. Thank you so much for having me and I echo your sentiments.

It's been really cool, which is weird to say while we're in a global pandemic, but it's been really cool to see the people that have continued to double-down on the marketing and the engagement and the follow-through.

And so, I love that you guys have started putting on this series. I'm honored to be one of the guests.

We did the same with our Facebook live show to just try and get out there and get in front of more people.

So, a little bit about me. I grew up in South Florida. I came up to Orlando to go to the University of Central Florida and I have never left Orlando since. I stayed here for law school, stayed here as a prosecutor, stayed here to open up my own firm, got married here, met my wife here, had a kid here, and all those wonderful things.

After running the firm, I realized that I had no idea what I was doing marketing-wise. I ended up six figures in debt from hiring, not necessarily bad marketing, but because I had absolutely no idea what I was doing. I couldn't convey to them what they should do and they weren't interested in helping me figure out what I needed.

They were interested in taking my money and I had made my decision. I own half the firm and my wife owns the other half. Our options were to find other jobs or for me to kind of figure this out.

That was in, I want to say, 2016 and 2017. Then, we had our kid in early 2018 and I said, “Alright, I'm just going to stop doing everything paid for marketing. I'm going to focus on meeting people so that if the cases go down, then great. We'll spend time with our kid, but we'll save $10,000 to $15,000 a month.”

And then I realize that it puts such a small dent in it because we were just yelling and throwing business cards off the roof of a building here. That would have been just as helpful.

Then I used that time to kind of learn what I was doing and then started helping other people. In January of this year, we opened up LegalEase Marketing. E-A-S-E cause I love dad jokes.

We have our dad joke in the name just in time for a global pandemic, which sounds like a bad thing, but turned out to be pretty good.

We've got a number of clients beforehand, smaller scale, and it really helped us work with people and provide free resources for people through the coronavirus. I would say, over the last four to six weeks, we’ve seen a huge uptick in people who are ready to get everything lined up, to get back out there and really capitalize. Now that things are slowly opening, it's been a really weird blessing in disguise.

Unfortunately, we've had so many people die. We've had such an economic hit on this.

Still, I think many of us will look back and see some positives from here simply because it got a lot of people being more tech-focused and got people also focusing on what’s important and realizing how important their family was, which is something that I've been lucky enough to be able to do.

I have a kid now and he just turned two in March. I've been working three days a week pretty much that entire time so that I can spend time with him.

And I want to share some of those tricks, tips, and guidelines so that you can have more time for whatever you want, whether that's working more, working less. Whether that's friends, family, sleep, exercise, or whatever. I think too often we, as attorneys, sit back and let our schedules get filled instead of taking charge of them.

Therefore, we are constantly busy even though we may not be achieving anything.


That brings up a whole other point about if you are spending time on meaningful work, but I think, just to start off the conversation with the mindset of Jordan, one of the things that I've always noticed about you is that you are very even-tempered.

You're very thoughtful in your approach to work. Even when we do live chat, or something, you're very well prepared. Just as prepared as anyone else would be. You would have totally fooled me if you said, “I work a hundred hours a week” for the amount that I see you producing.

Let's start with mindset. How do you set goals and get your mind to a place where you can delegate to the extent required to meet your goals?

Because I think that for many people, it's very hard to be a firm owner, especially in a small firm and especially in a business as ethically far wide regulated as the legal industry and owning a law firm.

How do you get your mindset and sort of that fear quelled to the point where you can achieve your goals? Where you can delegate to achieve them when it's not specifically legal work or maybe when it is so?



I guess let's start with the fear element. That's something that you just sort of have to get over through whatever means works for you.

My thing is if I woke up tomorrow and I wasn't an attorney, I'd be okay. I'd find something else.

So that's not to say that I run my firm by the seat of my pants or anything like that, but there is any other profession that is easier to make a living than being an attorney.

I'm convinced, and I talked to my doctor friends, and I'm like, “Look, you have to understand that if you were doing surgery and in the middle of it, another doctor was trying to kill your patient, that's what being a lawyer is like.” There is another side trying to kill you or ruin your case right in the middle of it.

So, I can't imagine a more consistently stressful job because most times, you don't have somebody actively working against you while you're trying to do your job and that's what got me over the fear.

It was just like, look, if I got disbarred or if I quit being an attorney tomorrow, I'd probably be happier. I'd probably live longer.

Whatever the positives are from it, everybody will have to find their reasoning to get over that fear because really it comes to the second part of your question. Like building that plan. That's where it has to start.

You need to sit down and lay out the plan of what you want your firm to look like, life to look like, and your bank account to look like.

And at the end of the day, you at least have to do the how, the what, and the when. How much money you need, when you want to work, and what you want to be doing.

But then, the more specific that you get with that plan, the easier it will be to make decisions that get you closer to that.

So, I tell people that's your definition of success and it may be mostly financial. It may be not as much financial and more time focused. It may be value focused.

Focus on the quality of your work by increasing the quantity of staff members and clients

You need to layout at least those three things and then see what else makes sense in the context of it. Otherwise, you have no idea where you want to get, so it's harder to figure out what steps will get you there.


Okay, when we talk about the outline of this webinar, we talked about having determined your best role, and that's probably also an influence in how to get there and how to implement it.

I think in law firm context, we see attorneys playing the rainmaker role, the admin role, the office manager role, and the managing partner role. How did that sort of buy into your framework?

I mean, before we started, you mentioned "I'm not practicing wise right now, but I could take a vacation", there's someone who's doing that. Where does that fit into, and how did you do that mental mapping of— what's the type of attorney that I want to be? And that could apply to other businesses too


So, basically, there's the age old adage, which is somewhat true.

If you can find somebody else to do this 80% as well as you can, you should delegate it.

While I don't know how that's going to apply a hundred percent of the time, it's a good place to start.

For example, I can find somebody who can attorney 80% as well as me. I can find people that make a better attorney than me because it's not my blue flame, it's not my passion.

What I've never been able to find anybody who could get that 80% mark was not necessarily marketing tactics, but vision. The vision for the firm, vision for the marketing, and vision for the client systems, etc.

So one, that had to be made.

And two, that's my blue flame. That's what I really enjoy. That's why I started a marketing company. I love sitting down and talking to attorneys about marketing and intake, and getting that client to sign up because we can all practice law differently.

We all do different areas of law. We all have different clients, but getting that client to like your firm and to want to hire your firm, get them signed up. It's going to be pretty consistent; no matter what you do, you just have to change how you make that emotional pole and make your value proposition, etc.

For me, both of those things fit in the same way.

I know a ton of great attorneys that are true solos and do everything themselves. I have no idea how they do it because I wasn't good at HR, and I wasn’t good at payroll, and I wasn't good at being an attorney while doing all those things.

So, for me, it was easy to bring on other people just because I saw the value in them doing something as well, or better, than I could do it.

That's not going to apply for everybody. There's going to be a part of you that will be an internal decision where you have to decide if you're okay giving up that control to have somebody else push your brand forward.

But, if you don't do that, you're going to work that much more and that probably is that much harder just because you're going to have to wear so many different hats and be the jack of all trades, master of none.

As a true solo, you're the custodian, receptionist, HR department, and the actual lawyer. You're so many things. God bless people that can do that. It just wasn't for me for so many reasons.


Well, what's interesting is you're bringing such a business perspective here and I just want to reference the Clio Legal Trends Report for a moment to frame this discussion.

That what you're saying is an anecdote, but it's not anecdotal in that the report showed that, year over a year, 86% of attorneys want to grow their firms in the next three years yet about 92% said that law school didn't prepare them for the business side of running a law firm and 76% say they lack the business acumen to run a law firm well.

Growing your law firm means you'll need more resoures

And all these things, I think contribute to, maybe not even taking a step back and identifying if are you really good and passionate about marketing for law firms or lawyers.

And that hasn't even been something that has sort of percolated to your brain yet because there is a strong identity in the amount of time and investment that it takes to become an attorney. I think for a moment, it would be helpful to also speak to the ethical component.

I know Kristin at LAWCLERK, the freelance lawyer network, very well. We've worked a lot together and there are many lawyer exchanges and networks around there. Did you start to sort of dip your toe in? Did you bring in a partner? How do we get around the ethical dilemma first and foremost?

For the lawyers who are here, to delegate some of those things— if you realize marketing is my passion or accounting or business growth and development is my passion, how do you make sure that your law firm is operating ethically if you're about to delegate some of that legal work?

Because that's often the things that are untouched when we talk about delegation.



The first step is a really good system. You have to have a good organized system in place. It can look like whatever you do.

You want it to look like it can be kept wherever you want it to be kept. It can be digital. It can be handwritten. It can be whatever, but without that, everybody else doesn't know what they're supposed to do and you don't know whether or not they did it.

That could be in a case management system with workflow, that can be a Tetra or from a Wiki page, that can be a three-ring binder that has a bunch of tabs on it that helps people figure it out. Without that, then you’re really just sending people off into the wilderness to fend for themselves as opposed to with the system.

It's not just, “Hey, here's this motion you have to write. Go have fun. Have it back to me tomorrow”. It's “Look, here's what you're supposed to do. Here are the templates we have. Here's what we're looking for here. Here's this”. And then you still have to, from my position, ethically review all of it.

Make sure it's correct. Make sure it's right. File it. If you're going to automate like we automate notices of appearance or HIPPA releases, something like that.

Do I read over all of them? I don't think so because really, it just needs a client signature and everything else is the same. For anything that has any resemblance of customization to that case, that's going to get read by an attorney a hundred percent, but the benefit is at my firm.

It can get read by a person who I met.

He was my law school professor that’s been a lawyer for 30 years because he’s the head of our business litigation department, as opposed to it being me who's been an attorney for eight years and really hasn't even been an attorney for the last two and a half years. I probably go to court six times a year and I probably take maybe four or five cases. I'm just trying to make it zero.

But with Coronavirus, and then I have a bleeding heart, so I hear the story of what somebody's going through and I want to help them. Sometimes, I can't pawn that off on somebody else.


Actually, that brings up an interesting point.

Framing our discussion, Jordan, I think of you talking about the three-day work week and it’s sort of the three days obliged work week.

There are two other days; true, they could be gardening or rock climbing or spending time with your friends and family, but they could also be doing pro bono work or working with clients that you otherwise would not have time and bandwidth to devote work to.

I think that it’s important that this three-day work week that you've delegated down to is something that can match a lot of different life and work goals and not just working less by definition.

Maybe you're someone who really does feed and grow on a five-day work week; but maybe you want to contribute to those other two days to less revenue-generating work that isn't required to make sure that you make your ends meet.

I think, oftentimes, it's a different target for everyone; what their revenue, their work goals are.

Let's talk a little bit about the fact that you are $200,000 in debt. You have a baby on the way. You have a marketing agency and you are taking over all your marketing work.

How did you determine what to tackle first in the face of so much opportunity and challenges? Who can take it on? Who do I trust to take it on? Especially without your decades in the legal industry, and how do you just get started? Do you dip your toe in? You look at the least risky and the biggest impact. What is your approach here?


So, there are three phases. We talked about the first phase.

I've got some notes over here. I just want to make sure I didn't miss anything.

The first phase is creating that plan we talked about. Once you have that plan, you know what you're building towards and, realistically, you can't necessarily build towards that in a straight line because I think the second phase is growth. And really, the third phase is delegation.

Because if it's just you, you have no one to delegate to, and you know that first hire may not be – you may have to delegate so many things that that position isn't designed for. You've got to grow into the size and the position to delegate everything properly.


So, from that standpoint, what I always talk about to people is, when should you hire somebody?

They look at it from a cost standpoint. I always look at it from an opportunity-cost perspective.

For us, for that first hire, I looked at where the cases were coming from. I was generating a good amount of cases. I didn't want to do the legal work. I wanted to do marketing. I wanted to be the face of the firm.

So I was like, “Alright, I'm going to hire a law student to do all of my e-filings and in exchange for that, I'm going to do two networking lunches a week instead of one. Then, I'm going to hire a paralegal to do these things and write my motions; and for that, I'm going to do now three networking lunches a week or do a happy hour Zoom hang out every week,” something along those lines.

At that beginning stage, you're trading off what you're doing for stuff that will either bring in more money or save you money so that you can get in that position to really have enough people to hit that true definition of success.

That is the true plan, that true road map. You can't really make the decision on what's the easiest and what's the best thing for me to delegate. You really have to go by what's the easiest thing for me to delegate, what's the cheapest thing for me to delegate?

Something along those lines, because you don't have the opportunity, like if we started this with venture capital money, then great, then every law firm would have a CEO, a COO, a CMO, and a CFO, as well as everybody who reports underneath them.

Where instead of that, I started a law firm with like $300 in my pocket and renting office space from somebody that I met when I was a prosecutor.

He was a defense attorney. You don't have the luxury that Uber has to have five billion dollars in venture capital money before the doors open and be able to lose money for the first, I don't know, five years of the program.

You have to make that decision based upon staying open, staying financed, and with the money that you have there.

That’s what I did at the beginning. It started with just me, and then we had a law student, and then we had a full-time staff member, and then my wife quit her other job to come work with us, and then we grew from there.

It was really at about that point, once I had her as a second attorney, that was really when I started being able to be more tactical in the delegation. Because at the end of the day, if s hit the fan, there was another attorney to go and do stuff.

When that isn't there, you can't really delegate as much because you still need to be able to do the legal work.


I think that brings up a really good point away from any three-day workweek discussion.

It’s critical that you have a backup, right?

Not just necessarily hire on the staff and your firm. In your business continuity plans and your disaster plans, if anything were to happen to you, you would need to have your clients served. You would need to have some sort of backup solution.

So for anyone who is here, who's maybe not targeting a three-day workweek or ready for that yet, it's still important to have someone who's identified as able to serve your clients, even if it hasn't been as formally structured out as Jordan describing.

Now, I think one thing also that Cassandra raised a really great question on is if you're focused, Jordan, on delegating the very first easiest lightest tasks, that means a fairly low-level person that you're delegating to, they may even be someone you find on Upwork or a freelance network, someone's kid.

If you're a professional who has college-aged kids or something, if you're bringing in those lower-level folks, whoever they may be, how do you prevent yourself from becoming the backlog?

Cassandra, this is something that I face personally. Any head of a department has faced this. Any head of a firm has faced this.

You delegate and then you have to train, monitor, answer all the questions to make sure that they're equipped with what they need; and that can feel like a whole heck of a lot of work. How do you not be the bottleneck?



So, the easy answer is it goes back to systems.

If you have that system in place, if you have their tasks organized, if you have a manual for them to follow, that's going to weed out so many questions.

The realistic answer is you need that first person to be a great hire because then they will build that for you with the questions that they do have.

So what I suggest to people is, no offense to Upwork or any of you that used it for that very first hire, but if you have a law school near you, that should be your first hire.

My first hire came back to our firm as an attorney. He did literally everything in the firm. He started out addressing mail and doing e-filing, and then he became a paralegal for his whatever it was two L summer into three L years.

He left to be a certified legal intern at the state for one semester and came back to work for us as little as he could during bar prep and then became an attorney for us because he was a great fit. Because he cared.

I think ten to 15 dollars an hour from a law student who wants to be a lawyer – you will get better work than twenty to twenty-five dollars an hour from somebody on Upwork or a virtual assistant or something along those lines, assuming that the position is anything remotely related to being helpful for them as an attorney.

They will genuinely learn on the job in a manner where they care about you and your firm and not losing them and getting their bar license at some point.

I worked for people super cheap and I learned so much.

When I was in law school, I actually worked for people for free and I don't do that now. I pay everybody. Some of them will just be ten bucks an hour as a law student for a semester; half of them finished and were like, “I realized I don't want to do this area of law. I don't want to do criminal defense. I don't want to do business law,” whatever the major practice they were working on, which is so helpful to them.

Just in learning, “Oh, I do want to do this. I do want to be an attorney here.”

And so that's right now, my paralegal and my director of first impressions. They took the L well; I guess they signed up for the L set and had to push the offset clause of the Coronavirus.

They were looking at going to law school in the next two years because they enjoy what they've done here and they want to hopefully be attorneys here. But if not, an attorney somewhere, just from the experience they've had. That's what I would suggest for that first hire is a law student. They will care more.


I have a couple of things. Also, Jordan, that's so great to add.

I've managed remotely now for three management positions.

I'll say that it's really important to identify the bottleneck because if someone doesn't have the information that they need to do the work – or are you the bottleneck because you need to review the work before it goes live? Like a blog post or something.

For me, I've realized that my tolerance is way higher for mistakes in blog posts and content that can be corrected because they can be updated and you publish to the website again and it's live and it's fixed. And no one even probably saw it anyway.

Let them sort of run with that, let them draft those things and build them. As long as they're not going to take the website down, the tolerance is pretty high for you not to review as much before it's live.

That goes for non-legal work, obviously. It's also important for people to write their own training manual, like Jordan was saying. We actually use Notion for that with

And it's important that when someone has just done something, it's really fresh in their brains. If you don't have a process for writing a blog post or social media or monitoring a marketing campaign or setting up Google Analytics or a new goal, for example, make sure that the person who just did that documents it If you haven't already.

Because obviously, when you're a solo small firm, it's very hard to take the time to document these things.

But when you're training someone, it can be their responsibility to document it and you can say, “You have ownership over this. So it is up to you how we organize these things and what do you think we should do?” And then they start to really care about it as part of their work.

And the last thing is to seek out the answer before you bother your boss. And that's something that you have to do when someone's already sort of on-boarded.

But if they have first sought out just to see if the answer exists, versus team members who always come to you first and you always respond to them, it's sort of pavlovian to train yourself to respond back to them. “Did you already look for the answer and you couldn't find it? Okay. Yes. Let's get on the phone and I'll train you,” rather than you always being the easiest first resort.

You're not always going to be available, and eventually, you won't be available a whole day of the week. What does that mean?

To me, that's been really helpful and proactive: check-ins with the team.

So now that we all have chat apps like Slack and Microsoft Teams, how easy is it now to be the bottleneck forty times a day when they think, “Oh, it's really easy to get in touch. Let me just send a quick Slack message, or chat, or Teams instant message.”

Then you get inundated continuously and that can be your entire day.

It's also helpful to tell your team, unless it's urgent, “Can you consolidate your questions at the end of the day or the beginning of the day? So I can review them while I'm having my coffee and I can answer them. Then your day is fully set up and equipped and I can be in meetings and not worry that I'm leaving you hanging.”

Because that's definitely something that I handle.

We’re on the Zoom call right now and what questions are accumulating from the team. They need to have peace of mind that I'll get back to them, but the more structure around that, the easier.

So I hope that helps and feel free to chat and ask if you have more questions about that, Cassandra.


Time-saving tips along those lines: video is your friend when it comes to building that training manual because you can either record your screen while you're actually doing it or literally take your iPhone on a tripod and stick it over your shoulder and record you doing it once and then that's the video for them.

You can get it transcribed later. You can have it edited later.

But you've added 10 seconds to start and stop this video, and then another 30 seconds to put it somewhere. But in terms of the actual time, you've done everything as you needed to do it.

You're not sitting down and trying to write it out while you're going through it or after you did it.


Those are really important to understand why you do things.

And I think, Jordan, if you can speak to that as an aspect of delegation, like how much do you need to bring people into, “The goals of this project are X, Y, and Z. Like, this is why we do social media marketing or this is why we're hosting these Facebook live events to build our community online.”

Because if you don't sell that, then you're just teaching these individual little tactics that never helped that person who you delegated to make decisions and even have ideas that are stemming from that goal that you told them about.

And they see the big picture and they can sort of operate and bring ideas to you that may facilitate the growth goals you have.



Yeah. From my standpoint, we are very revenue-driven.

Lawyers measure success by revenue, yet little actually value billing more hours

And I say that not necessarily from the standpoint that money is the end all be all, but there’s no problem that a business has that can't be solved with more money. You can hire more people. You can turn down more clients; whatever that you need, you need to focus on that.

And so, we talk to everybody as part of their job and in the context of generating revenue, whether that's actually doing the work on the case, whether that's providing such great customer service and such a great client experience that the client comes back, whether that's marketing the firm, whether that's getting them to write reviews, whether that's anything along those lines.

So throughout the timeframe that we have that client, they’ll get a couple of surveys. “How are we doing on the intake process? What can we work on?” What do they like? And anytime they mentioned anybody, which is almost never mentioning me, which is my favorite part of this; they'll mention the attorney they spoke to, they'll mention our receptionist, they'll mention our intake person.

Then we do a firm-wide email; “This is awesome, congrats to so-and-so. This is so wonderful.” We do the same thing to get reviews that mentioned other people's names.

We'll blast those out externally and internally and explain to them how this is a reflection of them doing a really good job at whatever their job is.

As a small law firm, you are always marketing. Everybody is on the marketing team because if they stink at their job, no one will hire the firm.

If they're great at their job, people are that much more interested in coming back, referring friends, writing that nice review, posting your stuff online, whatever it is.

And so, when you look at it that way, I think that helps everybody do a great job at their job, whatever it is.

Because they realize the positive benefit to the firm's bottom line, even if it's just them answering the phone when it rings, even if it's just them following up on those people to hire, even if it's just them taking that extra 15 minutes to send the client some interesting article that applies to their case.

Or when we were doing family law, we'd have some parenting coordinators that we work with consistently, so we’d send some information to the parent and follow up with the client who needed it.

Whatever that extra little white-glove, five-star service is, it's going to make a huge impact on the bottom line, by people being great at their job.



So let's move from the low-level tasks to, you know, higher-level tasks, mid-level tasks. How do you go there? Is it the same person or is it a new person? What's sort of your investment in their initial training, if it's not like these really easy, small, low-level tasks?



So the first part is you have to have the mindset that you cannot be essential to your firm and that may go completely against – we just had somebody leave. Maybe they feel strongly about that.


No, Sonia has to go. She'll be back, she said.


No, no, totally fine. I'm just, you know.

So we spend all of this time wanting to be the best attorneys, wanting to run the best firms, wanting to be wonderful. It's about us, we win these awards, whatever it is, but you have to have a firm where you are not essential. And then you have to have a firm where nobody is essential.

Because if, God forbid, somebody gets sicks, somebody takes vacation or maternity leave or paternity leave, whatever, if somebody is essential, everybody is going to bear that burden, you know.

If nobody is essential, and everybody can cover for everybody when that happens, so much better. So as you get past that growth stage, so it's not just you, maybe you have four or five people, then you can make the decision on what's going to be this person's job, what's going to be that person's job, and then what amI going to cross-train people on?

So we have everybody — they have their roles, they have their stuff, and then they're cross-trained usually on, like, a third of what's on other people's jobs just because that'll give us enough coverage.

The easiest thing is answering the phone. That's the thing that I think and, you know, I love that you're doing this with

Answering the phone is probably the most important thing for everybody in your life to do well just because you're going to have that day when there's a million people who call.

How many of you are on different Facebook groups, lawyer groups? You'll hear complaints about people being bad on the phone or a bad experience with someone at a firm or a marketing company or something along those lines.

Because it goes back to that conversation so that's a good place to start.

The other thing is finding people to work for you who are genuinely good human beings, which sounds like it should be easy, but unfortunately, it's not.

That's going to cover a lot of stuff, that'll overcome a lot of problems as well, if your staff genuinely cares about other people. Doesn't have to be you, it should the client, it should be the other people, the firm, it should be whatever it is. That's going to make them so much better at covering when somebody's sick or when somebody has to leave to go to a doctor's appointment.

And having that conversation with a client, you know a little bit more, kid-gloves or more understanding manner or whatever it is along those lines.

But that's— I guess, to answer your question— really, you need to get to that, maybe four people, to really start figuring out where those people fit in your plan.

The flip side to that is: what got you here may not get you there.

You may have somebody who is a great, you know, Jack or Jill of all trades who's a really good first hire. And we had this with a receptionist who we let go when we hit nine people because she wasn't great enough at anything to last in a spot.

When we delegated enough, she just, she couldn't keep up with the technology, she couldn't keep up with the systems, she couldn't keep up with all those other things so it was great when it was, you know, her and three of us because she turned over a lot of the problems, but when it got time to become an expert in something, she just didn't have it. And it still bothers me.

You know, firing somebody is the worst thing I ever have to do. Love it when it's firing clients, hate it when it's firing staff.

But you know, you have to be aware of, it's not just a the right person, it's the right person in the right seat and it's that seat being right long-term.

You know, people change, firms change, businesses change, technology changes, systems change. You know, sometimes you have to make that decision.

But you know, that's about the point that you can start delegating off the more serious stuff 'cause you can tell them, like, "Hey, you're going to be our lead paralegal so every motion is going to be written by you first so here's, you know, a law book, here's one of my law school books on writing business law motions or whatever. Read through chapters one, four, and six."

It'll help you with some of those things. You can spend more time training, you can do more specified training, you can do more – you know, you can make them less of a generalist and more of an expert.


So when you're— it's funny because you have two businesses. You have the law firm and you have the marketing agency and many law firms delegate to marketing agencies, as you're experiencing. You know, how do you position legal marketing from a delegation mindset where you know that a law firm has to delegate this, but it's not to an individual who they hire in-house to do the marketing, it's to an agency, you know.

When do you approach delegating to individuals and then, when do you look to agencies? That may be for marketing or bookkeeping or freelance lawyer help, paralegals, you know?



So, you have to look at value, not at price. That's the first mistake that people make.

People want to hire the cheapest accountant, or they want to bring in the cheapest staff member. That's not going to get you where you want to go. You need to go off value.

So for us, like, our accountant is— I don't want to say— is expensive, but he's worth it. Not only does he and his team do a great job, they also send us business so they're a really easy line item because I'm like, "Okay. I paid them, whatever its is, $6,000 last year to do payroll and books and taxes and all that. They sent us $15,000 worth of business, you know. Had I gone through paychecks, I would've saved some money, but really, it would have cost me money in the long run."

So in the beginning— it's interesting because you sort of bellcurve it. In the beginning, it's easier to outsource a lot of the stuff for smaller projects and maybe one or two staff members, but then as you continue to grow, it's easier to bring things more in-house.

And then it probably gets to the point where its easier to have your in-house oversee, you know, tactics from virtual — yeah. So the thing that we do for our marketing company that I— it's really, it's what I wish I had on day-one because we actually talk to the attorney about what they're really trying to do.

Who're trying to get in front of? What message are you trying to convey? What's your ideal client? What's your ideal case? What's your ideal situation?

And so they can then focus on being a really great law firm and we can focus on getting the right people in through the door when those things usually aren't – although there is an overlap between those things, it's a totally different mindset, you know.

Being a great lawyer and being a great marketer are almost completely different in a lot of respects. In other respects, they're at least not very similar.

And so it's one of those things where you have to look at it and see what's going to be the most valuable. You can spend a bunch of time learning to marketing or you an spend a bunch of time learning to be a lawyer or you can spend a bunch of time learning to be a great leader or you can spend a bunch of time learning to be a great business owner.

I mean, you have to make the decision for you and not care about what other people think. It has to be, "This is what's going to make me happy, this is what I want to work towards." And if it changes in three months, six months, a year, great! No problem.

But if you're not continuously working for what you want, you're not going to care as much, you're not going to be energized as much, you're going to get burned out fast.

If you're not going to, you know, put in that time, you're not going to care enough to make sure that you're going it the right way, at least in my experience.


Yeah. I think you make a really good point, Jordan.

And one of the other things that's sort of coming to mind is how do you know and how do you train your team— you talked about, you know, are they good on as people, do they have the right character traits, you know.

Skills are much easier to fill, character traits are way harder, if not impossible when you're already fully ready to train another person to do something differently in terms of their mindsets or their approach towards how much they care about things you care about, too.

But when it comes to, you know, hiring and identifying people, are there certain questions that you use? Do you want to make sure they have worked well with others and taken direction? Do you want them to be more go-getters? Like, is there sort of a personality type or a frame for bringing on these first people to help your firm that you use?



So phenomenal question and we're going to circle back to something we talked about beforehand.

So I try to get literally everybody in the interview, when they're interviewing here, at some point, to say, if all else fails and they can't find it the training manual and everybody is busy, to Google it. Like you talked about earlier, try to find the answer.

Like I want everybody to have that skill and if they don't answer that way, or if they don't have it, I pass just because I have to have— I don't want to micromanage. I don't want to manage, period. I have to, but I definitely don't want to micromanage.

In terms of background, look, I think Chick-fil-A is one of most well-run companies. I think they do a really great job, I think they have super nice staff, so if I'm looking for somebody to answer the phones or be client-focused, I look at where they were before.

Did they work at Chick-fil-A? Did they work at Disney?

We have Publixs over here, which is a supermarket that's known for being expensive, but really great customer service. Did they work for Publixs? Like I can use these gigantic companies that are making millions that, even on a $10/hr high school person, are training them on customer service the right way or the way that I want them to naturally fall back on.

And then I don't have to spend that money on the customer service, on the genuinely good human being part, I have to spend that on, "Now, let's take that to the law firm, let's take that to the client experience, let's take that to–"

You know, instead of somebody who can't find a can of peas, it's somebody who's not going to get to see their kid again. It's a different conversation, but really, you genuinely caring about that human being is going to be a transferrable skill across those things so look for people that have worked for companies that you really like and respect.

It could be competitors, it could be other law firms that, you know, you think do things that right way that have a great fit, it could be something totally different.

You know, we're in Orlando so Disney, Universal, SeaWorld employees get a ton of training on dealing with guests who are angry, who spent $10,000 on this vacation and now its raining, and they're pissed off and they're yelling at people. If you can deal with them, you can deal with somebody– with a law firm client.

So that's what I look for from those perspectives.


And when it comes to sort of getting started with a new employees or even a contractor or agency, like, do you use a trial period?

How do you sort of approach that getting-to-know-you, let's-start-working-together— like do you play out a lot of scenarios or do you actually have a probationary period where they start working for you and you both are starting to feel it out?


So we have a 90-day probationary period, which I've never really not exercised, like I've never had somebody hit 90-days and not hit day 91.

We had people who, within 3 days, we knew weren't a good fit and we were like, "Adios, see ya later."

But we always try to hire earlier. And so the reason for that is like, I want to give them a week or two weeks of just following everybody else around.

And then I want everybody to tell me how that person did and it could be like, "Look, they're super nice. And they were a little slow on this," or it could be, "They were great at it, but they were a little cold," and we'll make a decision on, you know, if that's somebody worth keeping.

Because for me, the whole point is having office morale, being high and having people that genuinely like each other, will help them work together better. We'll help them push our messaging forward. We'll help them run our systems better. We'll help them cover for each other.

And so I want them to be able to spend that time together during that training so they can see from somebody in action.

But also, we can see how they interact with that person.

I've had people come in, who we hired for attorneys spots, and they were super rude to my receptionist and they didn't have a job the next day because I didn't like that. They thought they were better than anybody.

Like, I don't think I'm better than anybody. I just took out a bunch of law school debt so I get to be an attorney as opposed to not, I mean, that's the— to me, that's the only difference between me and my receptionist is I took out a bunch of student loan debt and she didn't so.


I mean, I think that that mindset is really admirable, Jordan, and I love how down to earth you are and how you make the legal profession so accessible with that mindset that, you know, that you're just another human being. I really ascribed to that.

I'm wondering now that we have about 17, 16 minutes left, how do you keep things off your plate and don't let scope creep, sort of, happen?

There are new projects, you take ownership of them and all of a sudden, you know, that "I'll work a couple hours in the morning," becomes a half day, becomes a full day back on your schedule or a whole Saturday.

How do you maintain the things that are off your plate? Do you have sort of like a check-in on a regular basis with yourself and, you know, maybe your wife or other stakeholders to say, "Okay, what's everyone's workload balance like, or your mix?"

I mean, how are you sort of doing that gut check and also making sure that someone you're about to delegate more to can handle it and you're not setting them up for failure?



So let me answer that question a little circumspectly and then we'll get to it.

Really you have to look at it as 99% of law firms are going to do that process, are going to assign tasks in three ways: you're going to have email, you're going to have a case management system or a task management system, and you're going to have a calendar.

And so you have to look at the difference between those three things because that's going to help answer your question directly.

From my standpoint, an email, that's a task list you don't control. People send you emails and now, it's something that you need to do.

From the case management system, that's the task list you do control so you can assign tasks to people, workflows, you know. You have control of what gets entered in there.

And then, your calendar really becomes when those things are gonna happen and becomes your life plan.

So I always tell people, like, "You have to run your entire life off of your calendar, but not as a negative thing, as a liberating thing."

And what I mean by that is, like, if you don't want to work on Wednesdays, then just go onto your calendar and put, "Do not schedule me for anything for every Wednesday," and have a repeat every week ad infinitum.

And if a staff member sets you something on a Wednesday, you need to have a conversation with them about not to do that, to check the calendar, check the availability, et cetera.

The flip side to that is if you have to get something done, book it on the calendar. You know, a lot of people will set Friday mornings, nine to 12: "Don't book me for anything that's deep work time." That's whatever.

And so by, you know, that block scheduling, by making sure those times— by limiting them, by setting those rules, by controlling that calendar, you'll control the creep.

You know, you can, you can't control when emails come in, you can control what tasks get assigned to whom in a case management system. And you can control what you put on your calendar.

So a lot of times that's putting on your calendar that you're not going to do anything at this time, just as much as it's putting on your calendar that you are going to do certain things and what you're going to do at that time.

And then you have to really honor that, like, you have to cherish that time as if it's the most important thing because that will get other people to do it.

And along those lines, like, you should probably also offer that same thing to other people. So like none of my staff miss their kid's concert for school or a doctor's appointment, whatever, because I tell them, "Just put it on the calendar."

And when you're booking stuff, you need to check the calendar to make sure that, you know, we've got three, basically, three staff members that'll do phone answering and the legal work and client interaction.

So two of them need to be available in time. So if it's available, you want to take vacation that week, everybody's here, book it, you know.

You need to go, come in early, stay late, leave early, whatever it is, just book it and check the calendar for everybody else and give everybody that same understanding because, you know, happy employees are going to do better from this.

And then you're treating people, you know, relatively equally when it comes to those things. So there's a fairness and a team aspect and the camaraderie, but that's how you stop the creep, you know.

And that the belief, like, it is on my calendar until coronavirus every Tuesday and every Wednesday is you cannot set me for anything unless you check with me first. And I want to know why it has to be set that day as well as what it is.

And there's plenty of times that we do it. You know, I shouldn't say plenty. Maybe once every— I would say once every other week. I'll get booked for an hour thing on one of those days, trying to get on somebody else's podcast, they only go on those days trying to schedule a court hearing. The judge will only hear that on those days.

We've had clients who have flown in or about to fly out and have to get in immediately, something along those lines. But for the most part, like my staff knows, it's an extra hurdle to jump. And we're okay to jump it for the right reason, for the right situation, for the right experience.

And that's how you stop the creep: by being really specific and caring and honoring that time.


So I don't know if, Cassandra, you're willing to come on video and off mute for a second, but you had a really good question. And it would be awesome if you would be willing to, sort of, raise it to Jordan about delegation. If you turn your video on, then I'll know to unmute you or you can unmute yourself.

If not, I'm happy to sort of raise it, which is, you know, around calendar blocking.

So, Jordan, I think a lot of us, and myself included, like, it's easy to block off your calendar and really easy to also discount that time as only, "I know that it's my time," and "Oh, I guess I could have this podcast or this recording or this meeting that someone is telling me they need me for."

It's very tempting and sort of easy to take yourself and your needs less seriously than everyone else's needs.

So how do you prevent delinquency when blocking off your calendar time?



So we are super open with our staff, with our team. Like, they know how much money the firm makes. They know what money comes in. They know where it goes out. They know what our goals are. They know, I mean, all that stuff.

I know that a bunch of firms don't run that way and I don't have anything negative on firms that do, just, that's what we have.

And so a lot of that conversations when I talked about before, it's like, "Look. I'm not working Tuesdays and Wednesdays, but at the same time, when you need to go to the doctor's appointment, like, just schedule it. You don't need to ask us for the time off as long as there's nothing else on the calendar for that time for other staff book it, you know, if you need to go take care of your kids."

Your kid's sick from school. You need to go pick them up. Great. Go ahead and do it. Like, we have your support because at the end of the day, like, I talked to you about before this, and it sounds morbid, but like we're all gonna die one day. And I don't think anyone's going to sit there thinking, "I wish I had worked a hundred hours last week. I wish I had stayed in the office longer."

Everyone's going to think, "I wish I'd spent more time with my kids. I wish I hadn't sacrificed this for work. I wish I hadn't done that."

So I kind of let myself off the hook by honoring everybody else's time, as well. And so, you know, but at the end of the day, it's an emotional decision you have to make.

But if you're sacrificing your own time, then nobody else is going to honor it because you don't honor it to begin with.


That's a very good point. Very, very good point. And also, there is a point in you taking that time and either you need it for deep work, it is an investment in the firm in a different way, or you need it for rest and relaxation and taking care of your family, which allows you to come back to work the next day that you do.

I think another thing, just functionally to mention, is that if you're using a scheduling tool and you don't have it plugged into both your work and your personal calendar, to do so, like, you don't need to have everything on your work calendar, that's personal and private.

An example of calendaring your week and protecting your time

You can connect multiple calendars to check in just scheduling tools to make sure that like you don't get booked when it's some private event or doctor's appointment, things like that.

Your entire team doesn't need to know about it. They just need to know it's doctor's appointments.

But it's important to know that if you're using one of those tools that you do check, you know, all of your calendars, so it's not just work appointments. And then someone accidentally, you know, outside of your organization, books time with you when you have a kid's soccer match, you know.

So it's important to think about it holistically, but I think affording that same benefit to your team will help them be respectful. And then also, yeah, you don't want to breed resentment against yourself, even that you've blocked off time and then scope creep happens and you end up, sort of, betraying what your calendar said you were going to do and jumping into all these meetings.

I think another thing that I have allowed myself to do is to realize that there's going to be a lot of noise in Slack and in these chat apps and even on Facebook Groups and on LinkedIn. There are going to be conversations that I'm not a part of, or I'm not a part of in that moment. And am I okay with that?

Am I missing out on significant work or revenue or growth opportunities that I need to evaluate how I can be a part of that? And I can't be, you know, every place every time.

How do you even block out time for, you know, while I'm cooking dinner, I'm going to look at my Facebook groups and I don't have to be, like, a hundred percent attentive to that when something's cooking, I can do that at the same time, or I enjoy it and it doesn't feel like work, but if there are times that are dedicated, maybe run a Facebook group and that's real work, can that be delegated or can you block off time for that or have the proper alerts and notifications? And that's such a huge piece of that.

And Jordan, I would love to know, you know, as we, sort of, start to wind down on our time here today, how do you also use technology to alert you alongside your rules, like, how does that reinforce your rules? How do you not get notified on Thursday and Friday where your email is buzzing?

To me, if I don't turn my notifications off, I will have the biggest complex around, like, I'm missing work and I am letting people down who need me.

And I actually just have to have it be pretty binary: all or nothing. Yeah.


Well, so from that perspective, that's a great point. I shut badges off on so many of my apps on my iPhone so that I don't have that, one of them being email and the other one being Facebook, but the short answer is, like, look, we're delegating things downward, right?

Like, we should be focusing on the $500 an hour tasks and delegating down the $100 an hour tasks and then delegating down the $10 an hour tasks, whatever. At some point, that delegation becomes automation. So you can delegate something to a computer.

We use Lawmatics a ton for intake, and then my marketing company, we do build outs for Lawmatics for other firms, because if somebody contacts our firm, I can have 30 touch points with them that are automated texts, automated emails that aren't my office calling.

You know, another one is phone calls, I think, great from the inbound and also the outbound, because that's something that pulls somebody away from it. I mean, that phone call is more like email, right? That's a call you can't control.

And then when you schedule follow-ups, you don't necessarily control the other person answering.

And so you have to look at the technological ability you have there to take care of those things. Like, everybody should have calendar booking, like, you should have Acuity or ScheduleOnce or something along those lines. That'd be great. Then, they are— they're free. And then calendar is one more directional.

I sent you an email. It has my calendar. We don't have to have eight emails back and forth to find a time that fits. You know, if I can have that drip campaign automated, then nobody has to worry about it. The client calls, we enter the information and everything runs. Nobody has to keep that in their mind.

We can just process the information, scheduling hearings. That's a big one. That's easy to delegate for somebody else because a lot of times, your judicial assistant is not going to use your calendar booking, but if you delegate that to your lowest level staff member, they can be ready for the phone.

They can call that person, you know, three or four times a day to try to get that scheduling done.

Documents: you can automate a lot of those documents being generated. It may not be fully correct, but it might be 80% correct. And then you have to add the other stuff as opposed to constantly looking for the template.

I talked to a lot. We were with a lot of estate planning firms that have their clients fill out forms in really good detail about assets. And then, that goes right into the will, goes right into the trust. It goes right into there. So you're taking time off of your staff by having the client enter that information and then automating that entry.

Having other attorneys cover short hearings, moving things virtually has saved so much time for so many firms because you're not doing that 45 minute drive for that ten second hearing. And then the 45 minute drive back. But even when that's no longer an option, it may be worth it for you to hire a coverage company for a lot of those.

And maybe it's a hundred bucks to cover, but if you can build two hours of work at $300 bucks an hour, you still made $500 bucks. So, you know, I hate to go back to revenue, but it's sort of the easiest way to do it. You have to look at what are the things that will save you money by giving you time or allow you to bill more, or allow you to make more, or allow you to save your own time.

And then figuring out from there, you know, what's going to be the best bang for your buck. It's going to be slightly different for every firm. There's going to be certain, you know, if you like answering the phone, then pawn that off last. If you like writing motions, then pawn that off last.

But for the most part, I mean, you're going to know what takes up the most time, because if you don't, you can spend a week and follow what you're doing, write down what you did or you can look at your time entries for booking stuff through your case management system, or look at what cases you were in and what you were doing on them, or look at your calendar and see what was on there.

And then just start figuring out what's the easiest thing for you to pass off onto somebody else or pass off in to automation. And I always tell my staff, I'm like, "Look, you're not going to automate yourself out of a job. You're going to automate us not having to hire somebody else so that you can do less work or that you can do more targeted work consistently. It's easier to give you a rate."

Like, it's a lot easier to bonus the 10 people that we have than it is to bonus 50 people. Like, I know some PI firms have, you know, some of the larger firms over here might have a hundred people or even more between call banks and everything else.

Like, that's my whole thing for them is like, "Look, tell me what you're doing that you hate doing and then let's figure out how we can do it better, how we can do it faster, how we can automate it or how we can pass it off on to somebody else."

Like my paralegal, who can bill $100, $150 bucks an hour, shouldn't be doing e-filing when I can get a law student summer intern, or even a UCF undergrad kid for $10 bucks an hour to do all that.

You know, it just, it, again, it sucks to look at it that way, but it's the easiest way to figure out who should be doing what based upon cost and based upon opportunity costs.


Opportunity cost is such a strong resonator with me. I was an econ major and that's something that, you know, you do have a cost for your time, even if it's not immediately direct revenue generating work.

You know, if you're doing something that could be handed off, you don't necessarily have to be practicing law or doing casework, you actually could be networking or doing something that builds your brand in the community or refining processes or systems that do build brand value that only you can do, right?

Strategic marketing and planning, only you are going to do those things. And that's something that cannot easily be delegated.

Keep in mind, you know, you can't get a loan for more time in the day. That is the most precious and limited resource.

Jordan, thank you so much for joining us. I put some notes in the chat.

You know, your code is ease100 for a hundred dollars off. If someone is not yet using for receptionists and chat, it is a very easy thing to delegate to us. What are you going to delegate?

What are you going to delegate? What are you going to train? Can you go out and look for an interview, these people that you can invite to join your team?

So I think, you know, Jordan, your advice has landed really soundly on everyone here, a lot of positive feedback, and we've recorded the session.

We'll post it to YouTube. I will send it out later today and anyone who has questions, I put those in the chat, too.

Both my email and Jordan's, and feel free to get in touch with us. I know just like many questions, right? For management. There are a lot of things that seem private and personal that feel private and personal around what questions we ask with respect to delegation, with respect to a management that not everyone is comfortable sharing in a chat or on video.

So please feel free to reach out to us. There's a reason why we provide these webinars. We really wanted to do a service to the community and we'd love to hear from you.

So Jordan, thank you for joining me today.


Thank you so much for having me. This is wonderful.


Alright. Wonderful. Well, take care, everyone.

Have a great rest of your week.

Questions? Contact Us.

Have any questions about's virtual receptionists services or anything else mentioned in this webinar? Call us at (650) 727-6484 or email us at

If you’d like to learn more about how’s virtual receptionists can help your business, sign up for a free consultation with our team or get started risk-free with our 14-day money-back guarantee!

To watch more webinars like this one, check out our YouTube channel or access articles, guest blog posts, and other resources on the blog.

Business Education

Elizabeth Lockwood is the content marketing associate at She focuses specifically on writing and editing engaging articles, blog posts, and other forms of publication.

Take the faster path to growth.
Get today.

Affordable plans for every budget.

Sign up for our newsletter

By signing up, you agree to receive news & updates from
Thank you!
Your submission has been received.
Yikes! Something went wrong while submitting the form.

Take the faster path to growth.
Get today.

Affordable plans for every budget.