Outsourcing your back office operations with Dida Clifton, founder and CEO of The Office Squad. She shares how outsourcing key operational tasks can free up time for small business owners to focus on growth.

In this episode of The How of Business, Henry Lopez welcomes Dida Clifton, the founder and CEO of The Office Squad. They discuss how small businesses can improve efficiency by outsourcing back-office operations, Dida’s military-inspired approach to structure and processes, and the impact of delegating bookkeeping and administrative tasks.

Dida Clifton is a business owner, entrepreneur, and efficiency expert with over 23 years of experience in supporting small business owners.

As the founder of The Office Squad, she brings military discipline and operational structure to help businesses streamline their back-office operations.

Dida is passionate about helping entrepreneurs regain control of their businesses by providing outsourced bookkeeping, administrative support, and operational solutions.

Outsourcing Your Back Office:

• Dida’s journey from the Air Force to entrepreneurship
• Why structured operations are critical for small business success
• The biggest back-office challenges small businesses face
• The role of bookkeeping and why it’s more than just accounting
• How outsourcing back-office tasks can free up time for business owners
• How The Office Squad ensures financial security and prevents fraud
• Why hybrid work models can be more effective than fully remote teams
• The long-term benefits of outsourcing operations to prepare for growth or sale

Top 3 Takeaways:

1. Small business owners should focus on growth while delegating administrative and bookkeeping tasks to experts.
2. Operational structure and bookkeeping are key to business success, not just tax compliance.
3. Outsourcing back-office functions can reduce risk, improve efficiency, and make a business more attractive for future sale.

Episode Host: Henry Lopez is a serial entrepreneur, small business coach, and the host of this episode of The How of Business podcast show – dedicated to helping you start, run and grow your small business.

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Transcript:

The following is a full transcript of this episode. This transcript was produced by an automated system and may contain some typos.

Henry Lopez (00:15):

Welcome to this episode of the How of Business. This is Henry Lopez and my guest today is Deida Clifton Deida, welcome to the show.

Dida Clifton (00:22):

Thank you for having me.

Henry Lopez (00:23):

I’m looking forward to this conversation. Deida Clifton is the founder and CEO of the Office squad. The Office squad is a company dedicated to transforming the way that small businesses manage what we generally speak to or generally refer to, rather as the back office operations. And we’ll discuss what that means. So we’re also going to get into her entrepreneurial journey, very interesting journey and what this is all about, potentially outsourcing some of if not all of your back office responsibilities. You can find all of the how a business resources including the show notes page for this episode and learn more about my one-on-one and group coaching [email protected]. I invite you to consider supporting this show on Patreon and also I encourage you to subscribe wherever you might be listening so you don’t miss any new episodes. Let me tell you a little bit more about DITA and then we’ll get into our conversation.

Henry Lopez (01:17):

Dita Clifton is a business owner and a champion for small business growth with over 23 years of experience supporting business owners across America. As I said, she’s the founder of the Office squad, a franchised operations support model and DITA combines her knowledge of efficiency or military inspired operations background with a deep understanding of small business needs to deliver all in one back office. Solutions DA aims to change the way small businesses grow by helping owners operate more effectively, enabling them to focus on vision and growth. From a unique 10 point business assessment to comprehensive administrative and bookkeeping services, the office squad franchise network embodies de a’s mission to transform business ownership from struggle to freedom one squad at a time as she puts it. So with that Deida Clifton, welcome to the show.

Dida Clifton (02:10):

Thank you. That makes me sound like somebody

Henry Lopez (02:14):

Like you’ve accomplished something.

Dida Clifton (02:17):

Yeah,

Henry Lopez (02:18):

If nothing else, it’s surviving all those years of doing business and helping others do business

Dida Clifton (02:23):

Just to be here. It’s an honor. Thanks,

Henry Lopez (02:25):

I appreciate that. Well I always like to start at the beginning, especially with your interesting background. So tell me briefly about your early years. Did you go into the military before school, after school? Tell me about that if you

Dida Clifton (02:38):

Will. Right out of high school, right

Henry Lopez (02:39):

Out of high school,

Dida Clifton (02:40):

We didn’t do college, we went to the Air Force and I didn’t have a tech school so I went straight from bootcamp to a fighter squadron in Alamogordo, New Mexico. So I walked into a building full of fighter pilots.

Henry Lopez (02:56):

Wow. And what did you, 19

Dida Clifton (02:57):

Years old

Henry Lopez (02:58):

When you were the Air Force, what did you do? At least initially

Dida Clifton (03:01):

I was an operations tech, so in a fighter squadron there were this F 15 pilots flying active duty F 15. So there’s a great big desk in the middle of it and I worked behind that desk answering phones, talking to ’em on the radio, keeping schedule of what airplane they were in and where they were. So just kind of held down everything, made the coffee, took out the trash, all that stuff.

Henry Lopez (03:26):

And so obviously right off the bat you get exposed to operations, to managing things, to keeping things in order.

Dida Clifton (03:34):

Absolutely.

Henry Lopez (03:35):

In that environment I suspect not having been in the military myself, fairly structured,

Dida Clifton (03:41):

Very structured, which is where all this came from.

Henry Lopez (03:44):

A lot of SOPs and ways that things are done and so you learn that right out of the gate

Dida Clifton (03:50):

And there’s a huge sense of urgency that I brought with me to the office squad.

Henry Lopez (03:56):

Tell me about that. What do you mean by that?

Dida Clifton (03:58):

It’s training for war and I was in it in the late eighties and we weren’t at war, but in the military you’re constantly training for it so everything was in a hurry and you had to get ’em out the door and make sure they had everything they needed and it wasn’t weighed on the phone for things and like we do in the civilian world, things just don’t happen as fast. And when I got out I just wasn’t used to that.

Henry Lopez (04:28):

Also there I got to believe some of it involved actually somebody’s possibly their lives at risk. Yes. So the stakes were high.

Dida Clifton (04:38):

Yeah. Again, we weren’t at war, but every time one of those guys steps to a multimillion dollar aircraft and puts his life in there, you got to make sure that everything is going okay.

Henry Lopez (04:53):

Alright, so you served, I think it was six years, and then what did you do after your service in the Air Force?

Dida Clifton (04:58):

I got out of the service and became a military spouse and volunteered a whole lot

Henry Lopez (05:03):

And traveled different posts or

Dida Clifton (05:07):

Yes, he moved about every two and a half to three years. We got to Nellis Air Force Base in Las Vegas in 2001.

Henry Lopez (05:18):

So during all that time you didn’t have a job outside of the home?

Dida Clifton (05:22):

Not really. It’s hard to keep a job when you move every couple years. So I did a lot of, started my own little gift basket business and I did a lot of volunteer work. I opened some thrift shops and he was stationed in the former East Germany for a while and I taught them how to open a thrift shop and I just did a lot of really cool things and raised a couple of kids.

Henry Lopez (05:46):

Yeah, there’s that. So what leads you to the office squad? Was that shortly after you then became more permanent in Las Vegas? Was there something else in between?

Dida Clifton (05:59):

Well, once you get to know me, you know that I don’t sit idle for very long, always trying to do something. So shortly after he got to work and the kids got in school, I started a little bookkeeping business from home when the virtual assistant thing just started out.

Henry Lopez (06:16):

Interesting. And why bookkeeping? Did you have an accounting background as well?

Dida Clifton (06:20):

No, by the way, anybody can be a bookkeeper, don’t have to have school or lessons or license or accountability or anything.

Henry Lopez (06:28):

I know it’s wild, isn’t it?

Dida Clifton (06:29):

It is. So I learned QuickBooks during a lot of my volunteer work. I volunteered to be treasurer and I started thrift shops and so I knew how to use QuickBooks and I can start a business. So I did built my own website and I started faxing, remember faxing? Faxing a little info sheet to people were advertising for bookkeepers.

Henry Lopez (06:56):

Oh, okay. So that’s how you landed your initial clients?

Dida Clifton (06:58):

Landed my first clients and then I would drive to their place and back their QuickBooks up on a little stick and take it home. So did that for a while and I quickly realized that business owners needed a whole lot more help than just bookkeeping and they were a lot like fighter pilots. They needed a whole lot of support and they really didn’t care about anything but flying. They all wanted to just do their business and please take care of all this other stuff for me.

Henry Lopez (07:28):

Right. It’s noise and it’s painful and it just gets piled up. Right,

Dida Clifton (07:32):

Right. So that’s where the office squad came from. I just kind of started adding things to it, moved out of the house and it just kind of grew and grew.

Henry Lopez (07:39):

How many years has it been?

Dida Clifton (07:41):

Henry Lopez (07:42):

Wow. 23 years. Excellent. When you think back to then have, I mean obviously you had dabbled a little bit as you said while you were traveling, but did you have aspirations or did you think you’d have your own business one day?

Dida Clifton (07:54):

No, it was kind of an accident. I saw a need for it. I saw people would come to me and their bookkeeper had moved or wasn’t answering their phone calls or didn’t have time for them anymore or did their books wrong and wasn’t going to fix ’em. They were just, excuse me, getting screwed and I didn’t think that was fair.

Henry Lopez (08:18):

It’s happening even more so now. It’s so hard to find reliable bookkeeper or reliable CPA for that matter. It’s not easy.

Dida Clifton (08:26):

I realized that anybody could be one and I just wanted to fix that. I didn’t like seeing that small business owners didn’t have what they needed and I thought that I could fix it. So

Henry Lopez (08:37):

Of course all that discipline that you had, the application of rigor following a process because in accounting and bookkeeping we do need to balance to the penny not close enough. All of that has to have been those skills. Were there that characteristic that you had all of applied? I have to think

Dida Clifton (08:56):

It does. And organization and having your files set up and knowing where to find things and I started answering phones for people. I moved out of the house and started adding things and receiving the mail and it just started adding stuff.

Henry Lopez (09:14):

Just grew from there

Dida Clifton (09:15):

Bigger.

Henry Lopez (09:17):

One of the things that I’m curious about as I was doing the research is your daughter Taylor, am I pronouncing it correctly? Taylor?

Dida Clifton (09:23):

Yes. Yes.

Henry Lopez (09:24):

She works in the business with you and that’s always a tricky thing having especially our kids in the business. What are a couple of thoughts or tips on how you make that work?

Dida Clifton (09:33):

Well, I don’t know how much time we have, but I have two daughters

Henry Lopez (09:37):

And they both work in the business or just one of

Dida Clifton (09:39):

Them? No, Taylor’s the youngest. The oldest was my first receptionist

Dida Clifton (09:46):

And I fired her three times. So my advice is never hire family. But then Taylor came along and she was always in sales and she’s very good at sales and I kept asking her to come on and be my salesperson and she wouldn’t do it. And then Covid happened and she, she’s in her thirties and the retail industry went belly up and she said, is that all for still good mom? And I said, absolutely, because she said, okay, well I’ll try it. And she did an outstanding job and we knew going into it, she was older, we went into it as grownups and I think that made the difference The first time that my older daughter did it, she was in high school and that’s a whole different bond,

Henry Lopez (10:32):

A whole D thing. You were a parent then here now with her, this daughter, you have an adult relationship now with her.

Dida Clifton (10:40):

Right. We knew what we were getting into and she raised our revenue a quarter, a million dollars the first year she was

Henry Lopez (10:47):

In it. Wow.

Dida Clifton (10:48):

And she’s the CMO and she does great. So I think you have to be an adult about it. And my office staff, I asked all of them and you have to not play favorites.

Henry Lopez (11:04):

That’s a tough one. Yeah,

Dida Clifton (11:05):

Yeah, it is. The staff has to know that my daughter’s going to come in and this is what she’s going to do and if you see any issues, please let us know. They’re not afraid to hear it.

Henry Lopez (11:15):

It is got to help that. I dunno, maybe some of them were there when you fired your other one so they know you, you’re serious, or at least they’ve heard of that, that you’re not beyond firing them if you have to.

Dida Clifton (11:25):

Well, none of those people are there either because that’s a big thing you have to learn too. You can’t be friends with the people you work with.

Henry Lopez (11:31):

It’s such a big learning lesson. The way I used to put it is you want to be friendly, but the whole thing where I say, well this is a family. No, it’s not a family. I mean it’s a family of sorts, but you are the boss and there is a line there that we have to manage is my experience. What do you think?

Dida Clifton (11:49):

Yeah, I have a couple of millennials that run my company now and it works great in Texas and they’re in Vegas now, but it used to be they would come in my office and gang up on me and I would listen for a little while and we would discuss it and then I would go, okay, here’s what I think get out of my office. And then we could agree to disagree and that’s fine.

Henry Lopez (12:13):

That’s right. But at the end of the day, there’s one boss and you have to make decisions

Dida Clifton (12:18):

And if they can live with that then they stay and if they can’t, then there’s the door.

Henry Lopez (12:24):

Understood. Alright, let’s start to get to it a little bit more. We’ve talked about it already and I mentioned it in the bio, but tell me a little bit more about when you look at your clients, what are some of those common operational, administrative back office challenges that they come to you with?

Dida Clifton (12:40):

Well, bookkeeping is the main thing that we do and my philosophy is bookkeeping is not accounting. And I think there’s a misconception with that. People think that bookkeeping is something that you do at the end of the month or maybe at the end of the year. You just take all of your stuff to the accountant and somebody data entries, it magically you have your tax return. But bookkeeping is actually operations. It happens every day. It’s a check, it’s an estimate, it’s an invoice, it’s a phone call with a customer. It’s a phone call with a vendor. It’s what happens every day. They call it full charge bookkeeping for a reason.

Dida Clifton (13:19):

Accounting is looking at numbers and thinking about the future and auditing and that stuff. The office squad does bookkeeping. We make sure that the receipts are in, we make sure all the documents are organized. We put your p and l and your balance sheet together. We look at it with you, make sure that the numbers make sense for you and bug you until you get us what we want and need to get you what you need. So we do a lot of nagging. My oldest client’s been with me for close to gosh 15 years and he says I’m an expensive nag. We tell them that it’s going to take about three months and they’re going to hate us for the first three months and then it kind of clicks and they get it and they stay and they stay a really long time

Henry Lopez (14:13):

In those three months. What’s from an operational perspective, what’s one of the key habits that you’re helping them develop?

Dida Clifton (14:18):

Well, they have to pause and listen. The things that your bookkeeper, the people that are trying to do a job for, you need, you have to listen to them. You have to get those things for them or give them the power to get those things.

Henry Lopez (14:31):

And do you think that they haven’t done that because they’ve seen this as again, a back, I mean even the name of it implies that something that’s not important, I’ll get to that eventually that can wait.

Dida Clifton (14:42):

Yeah. Bookkeeping is not important until it starts yelling at you until it’s tax time or as long as I got money

Henry Lopez (14:49):

Or until you’re navigating your business blindly because you don’t have that data

Dida Clifton (14:55):

To

Henry Lopez (14:55):

Tell you what’s going on.

Dida Clifton (14:57):

As long as there’s money in the bank, I’m fine. And now you’ve got it where you can get up in the morning and you can see in your phone that you have money in the bank and you’re fine, but what’s going to clear that day? What do you need to pay next week? What you need is a dashboard and QuickBooks has it. If you could get up in the morning and pull out your iPad and look at a dashboard that says, okay, this is what you have in the bank, this is what’s going to go out next week, this is what’s going to come in. Then you have a clear picture and your bookkeeper can do that for you. If she has, he or she has the right information and it’ll do it automatically. I have no problem with ai. I love hooking things up and making it work, but you’ve got to take the time to get all that stuff set up and someone needs to monitor it.

Where are you seeing is the impact of companies, businesses that have remote or virtual teams, how does that potentially exacerbate all of the back office operations?

Dida Clifton (17:38):

I am not a big fan of remote teams. My team works in the building together in Las Vegas.

Henry Lopez (17:46):

What are the reasons you don’t like it as it relates to the impact on back office operations?

Dida Clifton (17:51):

I don’t mind hybrid, so the girls can work, girls or guys can work from home when they need to. If they don’t feel well or the kids are home from school or they have the option to do so. I can work remotely from Texas because that’s where I am, so we have the power to do that, but they only get to work remote after they’ve been with the squad for a year. You work together, you fight together, you go down together and tax season and the things that happen when it gets really busy around January, February and March, it’s really hard in our industry and I’m sure industries all over have the time where there’s a hard time where everybody has to pull together. Reception helps the bookkeepers and admin print statements, and we all work together to make things happen. And we have a sense of urgency.

Dida Clifton (18:45):

If somebody calls and needs something and Susie’s out on vacation and nothing can happen until Susie gets back, that’s not acceptable. Somebody else needs to know how to do it. So at the office squad, we cross train, there’s never one person that knows how to do it. We will get it done. So anyway, there’s a bar in the middle of an office squad coffee bar in the daytime and sometimes there’s cocktails at night and we do networking. So there’s a whole different comradery around this world that we work in. And yes, you can work remotely from home, but the comradery of how we work together is very important to me.

Henry Lopez (19:22):

Okay. Let me ask you this question. Why in your experience with your clients, is it better for them to outsource these tasks of bookkeeping and other operational tasks to you rather than them hiring somebody, hiring a bookkeeper in house and doing these things in house? Why is it for the clients that you serve, why is it better for them to outsource it to you rather than them staff it themselves?

Dida Clifton (19:46):

Are they going to hire one person and teach them everything?

Henry Lopez (19:48):

No. Let’s say I have a team, I’m at the size where I could justify hiring a team of people to do bookkeeping and other back office functions.

Dida Clifton (19:58):

That’s fine if you’re big enough to do that. We have clients that we’ve grown big enough and they’ve left us and done just that and that’s fine. We’ve also

Henry Lopez (20:07):

Had, so this is the sweet spot for you, the smaller businesses where I don’t have that resource and I don’t want to invest in that resource.

Dida Clifton (20:15):

Correct.

Henry Lopez (20:15):

What’s the best practice that you would recommend to business owners to at least minimize the potential for embezzlement within your group to happen? Not your group, but their employees.

Dida Clifton (20:27):

We have three sets of eyes on things. Whoever’s putting the data in is not doing the reconciliations. So there’s two sets of eyes there. And then we have a lead bookkeeper that oversees the stuff at the end of the month and looks it over a third time and looks at all the reports.

Henry Lopez (20:44):

And then as an owner, what in your opinion, even if I outsource to you, what should I not let go of? In other words, what am I still responsible for as far as what the bookkeeping produces, the financial statements, if nothing else, what do you think a business owner should still be involved in to make sure they’ve got their finger on the pulse of where the money’s going?

Dida Clifton (21:04):

Always sign your check and you don’t always have to physically sign them. We have clients that we can print their signature. We have a signature stamp and we have ACHs, but what we do is we send them a list of what needs to be paid. And the gentleman that I told you we’ve been working with for 15 years, he’ll say, pay so-and-so. He’ll just call and say, pay so-and-so this much money. And then the bookkeeper will send him an email that says, you told us to pay so-and-so this much money, please prove in writing. He emails back, but do this for 15 years. I told you to do it on the phone. Why do I have to write it?

Henry Lopez (21:45):

There’s so many stories of that. The people committing fraud and others committing fraud pretending to be somebody, right?

Dida Clifton (21:53):

So every time there has to be a written approval and he still, every time

Henry Lopez (22:00):

He doesn’t like it,

Dida Clifton (22:03):

That’s just him, but he loves us. But everything that leaves must be looked at and approved in writing.

Henry Lopez (22:11):

You think we should look at our balance sheet on a monthly basis? What are we looking for there? What should a business owner be looking for? At a high level,

Dida Clifton (22:18):

There should be no negatives, no negative numbers anywhere. And if there is a negative number, like a negative equity someplace, why it’s there. Whereas your ar, is it an ungodly number? Why is it a big

Henry Lopez (22:30):

Number? I’m a big believer in getting as granular as makes sense, and I know it can explode some CPA’s minds because it adds complexity, but as granular as I need it as a business owner for that data to make sense to me. But what are your thoughts

Dida Clifton (22:48):

As a business owner? I understand it, but less is better.

Henry Lopez (22:52):

Right? Summarize for me who’s an ideal client for you? Tell me that again.

Dida Clifton (22:56):

Our ideal clients are companies that are under 5 million, under 50 employees. We do scheduling and dispatch. We love the small mom and pop PEs, control hvac, the companies where the husband and wife started it and the wife was the bookkeeper and now she doesn’t want to do it anymore kind of thing. They’ve gotten,

Henry Lopez (23:17):

She certainly doesn’t want to be blamed anymore for things.

Dida Clifton (23:20):

Let her go do something else. Exactly. We love those

Henry Lopez (23:24):

Because going back to that point, those are companies where they’re better off investing in hiring another technician, let’s say, than hiring a back office staff.

Dida Clifton (23:32):

Yeah. What’s unique about us is you can have someone to answer the phone, a bookkeeper, a manager, to manage all of those people and someone to help with all the paper in the middle for less than the price of one employee normally. So we also have, if you’re in, as this franchise thing builds out, we hope to have an office squad in more communities. So you have one in your neighborhood and there’s coworking and there’s executive suites and maybe a little networking and meeting other business owners.

Henry Lopez (24:03):

Yeah, that’s a great idea to combine those two things. I think the other thing I always tell people about these types of things, which are not your core competencies, so that HVAC company bookkeeping is, that’s not their core. It’s serving HVACs and serving their customers. But the other thing that you get by going with someone like you is you have now you can bring to it diverse expertise and best practices because you’re continuously learning from how others are doing it, how you’re helping others, as opposed to somebody I might hire, they become siloed within my organization. Does that make sense?

Dida Clifton (24:41):

Yeah. You have the bookkeeper that’s been your bookkeeper for 20 years and you don’t want to change it

Henry Lopez (24:47):

And they become stagnant. Who knows? Whereas in your team, because of the nature of the business, you’re staying fresh, you have people on board, you have more resources, you have access to resources that I’m never going to have as a small business owner if I build my own team.

Dida Clifton (25:03):

We have everything in the cloud and you don’t have to buy computers and you don’t have to provide all that stuff. You don’t have to worry about HR and salaries and all that fun. We have to do that.

Henry Lopez (25:12):

Alright, let’s wrap it up here. Let’s, one thing you would say to the small business owner listening, that HVAC business owner, the electrical contractor, whatever the case might be as to why they should consider outsourcing these operations. The back office stuff, the bookkeeping and related tasks,

Dida Clifton (25:31):

Vacation. I have an HVAC company that came to us for phone answering and she never got to go on a vacation until she hired us and now she’s able to go to her home country in Cuba I think. And she came back and thanked us that she got to take a vacation without having to worry about the phones.

Henry Lopez (25:53):

Yeah, so freeing up that time and allowing you to concentrate on, again, where the core strengths are building the business as opposed to being bogged down with the transactions of the operation.

Dida Clifton (26:05):

If the operation runs without you, then it has value and someday you might be able to sell it.

Henry Lopez (26:12):

Exactly. Well said. Alright, where do you want us to go online to learn more about the Office squad?

Dida Clifton (26:16):

We have a great [email protected], so tango hotel echo office squad.com, and you can email us at help HEL [email protected].

Henry Lopez (26:30):

And I didn’t touch on it, but you offer a discovery call for somebody who might be interested and wants to discuss potentially the services that you offer

Dida Clifton (26:39):

Under services on that website. It’s called COO Service and it’s a free discovery call. We get on the phone for an hour or 45 minutes and talk about what’s going on in your business, what you’re happy with, what you’re not happy with, and I give you a little insight and maybe some help on what you could maybe do better.

Henry Lopez (26:59):

Dita, thanks so much for taking the time to be with me today and sharing this information. I appreciate you being here today.

Dida Clifton (27:05):

It was fun. Thanks, Henry.

Henry Lopez (27:06):

This is Henry Lopez and thanks for joining us on this episode of The How of Business. My guest today again is Dita Clifton. I release new episodes every Monday morning and you can find the show anywhere you listen to podcasts, including at my YouTube channel, the How of Business YouTube Channel, and at my website, the how of business.com. Thanks again for listening.