Ep. 117 – Less Doing Chief Operating Officer, Courtney Waid

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Thanks to the ever-evolving nature of technology, the tasks involved in running a business become much more manageable and easier each day. By automating business strategies, entrepreneurs can improve their systems in the most significant way and focus on other important matters, both inside and outside the workplace. Cameron Herold sits down with Courtney Waid, COO of Less Doing, to discuss how their company helps businesses build effective automated systems that yield actual results without requiring many resources. She also shares how she applies her military training into the entrepreneurial setting, her relationship with CEO Ari Meisel, and working full-time alongside being a mother of four.

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Courtney Waid is the COO of Less Doing, a company that coaches successful entrepreneurs to make themselves more replaceable in their business so they can focus on the work they love. He holds degrees from United States Military Academy at West Point and George Washington University. As a former military intelligence officer and an Iraq War veteran, she lives outside Fort Worth, Texas with her husband, four children and a menagerie of farm animals. She also works with a good friend of mine, Ari Meisel who is the CEO of Less Doing. Courtney, welcome to the show.

Thank you. I’m excited to be here.

Did you go to West Point?

I did.

“Holy shit.” Is that the reaction you get from everybody when they hear that’s where you went to school?

Yeah. Especially as a woman, sometimes people have this idea of what you would be like. We definitely have some surprises, for sure.

What was it like?

I loved it. I loved clear cut expectations. I loved left and right limits. I loved the idea that every day we were doing something that seemed important. The war on terror kicked off in 2001, so I was early in my sophomore year when all that started. It suddenly went from the war being this thing that happened in history to being, “This is what we’re going to do.” Everything at West Point seemed to shift. Every minute we were spending was, “How does this prepare you to lead troops into combat?” It was exciting. It was being on the cutting edge of something historical.

How long were you in the military then?

I stayed in six years. I got out in 2010 quite begrudgingly. I love the military as well. My husband’s also a grad and we were dual army officers at the time. The OPTEMPO was year-on, year-off deployments. We had just had our second kid and our oldest two kids were fourteen months apart. It was a disaster. I’m not doing a good job as a mom, as a wife, and as an army officer, so one of the things has to go. I got out and did the stay home mom thing. My husband stayed in and has had quite a good career. I did the army-wife lifestyle for a while until meeting Ari and getting into working with him.

Has he stayed in the military then?

Yeah. He stayed on active duty up until a couple of years ago. He’s in the National Guard now and he’s the lieutenant colonel. He’s about to take a battalion command, which is a big deal. Sometimes it’s surprising because I remember being a lieutenant and lieutenant colonel seemed old and wise. That’s like, “I’m not old enough to be married to one of them.”

I was speaking with somebody one time and they’re saying that when they graduated from college, they thought they were all-wise and all-knowing. They look back now and go, “I knew nothing. I was such a kid.” How did you end up meeting Ari then?

We have a Facebook group for West Point, women graduates, and somebody had posted that her business had done some work with Leverage, which Ari was a part of at the time. It’s a great experience. She felt in Leverage is the best company and she had heard that they were hiring and thought that it was a good opportunity to share in that group. A lot of the West Point married women grads end up in the same boat that I end up in with the dual military lifestyle. It doesn’t seem like it’s going to work out. I struggled to find employment. We want to get out to focus on our kids. That’s going to be our number one priority.

We don’t want to work big 9:00 to 5:00. We’re highly educated and motivated. It’s hard to find a job that’s challenging and uses your skills, but also doesn’t demand an army level of commitment. She posted that and thought, “Somebody might be interested in this. It’s flexible. You work from anywhere.” I begrudgingly said, “Fine. I’ll be a virtual assistant. Me and my Master’s degree will go and be virtual assistants,” which I didn’t have a sense of what that meant at the time. I ended up enjoying my work with Leverage quite a bit.

It wasn’t scheduling doctor’s appointments and get the TaskRabbit to come to pick up my dry cleaning, which is my day-to-day life anyway. I sign my kids up for camp. It was a lot of high-level business tasks and the things that I enjoyed. It was neat to get close to Ari. What we do with Less Doing and what I’ve seen since then is I never thought it was possible that you could work a meaningful, challenging, rewarding job and have that flexibility to focus on your family and interests and have that time. I do credit Ari with opening my eyes to the fact that it could be a reality. You can have a job that’s fulfilling and have a life that works and those things don’t have to compete with each other all the time.

I’ve known Ari for several years, so I understand what Less Doing does. Can you, for our readers, tell them what Less Doing is and give us an idea of what your company does?

We run a coaching program. We have an online course and a workshop as well, but our primary focus is coaching. We coach successful entrepreneurs that have businesses that are tried and tested. They know it works, but what’s happened is the snowball effect of success, where they started these businesses because they have this world-changing idea. As they begin to turn that into a business, the minutiae of it start taking up all their time.

The day-to-day running of the business detracts them from focusing on what they do best and the things that got them into business in the first place. We coach them to create systems in their business. Primarily around their communication, project management and process that either automate a lot of that day-to-day stuff or create systems where their teams or other outsource providers can handle that. They can get back to doing what they do best, focusing on the work they love and less on the work that they don’t.

You are about optimizing and automating their processes and helping them remove themselves from the day-to-day more than just general business coaching. It seems like you are focused in on the optimization and automation of process, right?

Yeah. Very much around systematizing.

Who would your typical customers be? How would you describe what your customers might look like?

Unlike a lot of programs, we are not industry-specific. We don’t focus on the best marketing techniques or lead generation and that sort of thing. Our ideal customer is a successful entrepreneur that has the business that they know works. Somebody you’ve met that has the vision. Not serial entrepreneurs that just want to jump around to new things, but somebody that has a company that they know is going to change the world and they believe in strongly.

Is there an employee size that works best for you? Is it a 20, 50, or 500 employee company? Is there a zone that works well?

Automating Business Strategies: Different people are not supposed to do each other’s jobs, but they have to learn how to get along and understand one another to leverage effectively.

There is not small enough that they can change. Most of our successful people that get the most impact at our business are probably teams between 10 and 20. Big enough that they have a team and the resources. CEO has people that can do the work for them, but not so big that changing the way they do business is too hard.

They probably don’t yet have a mature leadership team, do they? Or would they be starting to build one out?

They are starting to get there. A lot of these companies are still trying to figure out those roles and who’s responsible for what.

Has there been much of a shift in the organization when you joined years ago to Get Leverage and now Less Doing? How are you focusing on your clients now? What’s the pivot been?

Less Doing is totally separate from Leverage. It’s interesting. You know Ari, so this will not be a surprise to you. For people that don’t know Ari, when we started Less Doing, we had a much larger team and we did a lot of things. We had a high-level mastermind, a smaller group coaching program, and an online course that we came up with. We had a smaller monthly membership program and we did consulting work. We ran the gamut of all the ways we could help entrepreneurs and we have narrowed that down now, which has been fun. Consulting was a unique one because it brought in a lot of money. High ticket consulting and able to help businesses.

One day, we had an honest team meeting where Ari and the people on our team that were responsible for consultants were like, “We don’t like this work. This isn’t enjoyable.” I, of course, wanted to wring my hands and agonize over it and look at the numbers. “If we cut it, then the revenue.” Ari in his fashion is like, “It’s no fun. We’re not doing it anymore. I’m going to call all the clients and tell them we’re not doing it anymore.” That’s how it’s gone. We’ve narrowed down the focus primarily on coaching, and then narrowing that focus on communication, project management, and process as the three primary areas where we see almost every single business struggle when it comes to systematization.

You mentioned letting the entrepreneur get back to what they love and you mentioned a lot about work-life balance. Ari, the CEO, got quite sick a number of years ago. Was it with Lyme disease?

No, Crohn’s disease.

That was a big shift for him in his life where he decided to not work these insane hours and tried to optimize life so he could have a business running itself and he didn’t have to be there doing it. Is that still a core driving force for him? Is that part of the core driving force for the organization not to help people that are sick, but almost to help them as if they were?

Yeah, it is which is the thing that I love about working there. We operate under the assumption that there are things in your life that are more important than work that matter more than your business. The clients that we attract are like that as well. I was on a call with a guy and my kids were being noisy in the background. There are four of them and I was like, “Sorry that they’re making noise.” He instantaneously said, “Don’t apologize.” It was a great moment for me to recognize that I’m in a company where that’s not a deal-breaker. There is a level of professionalism that goes without saying, but it’s not a deal-breaker, that there are kids in the background.

Ari runs coaching calls from his car and we’ve heard clients at first be like, “That makes me uncomfortable,” but as it goes on, they’re like, “No. I love that. I love that I feel I have the freedom to jump on this call from wherever I am and I can bring my authentic self to this coaching program and not worry about the way I look, the way I present myself or, ‘You can’t know I have kids in the background.’” That’s very much about for us.

How are you juggling the role of a COO and being the head of a family with four kids? How do you manage your time?

Some days are better than others. I get up early and I work. I work a little bit after the kids go to bed. When there was school, that was helpful, because I did a couple of days a week while my kids were in school but one of the great things about Less Doing in the way that we’ve set up and what we coached other businesses to set up as well is we do so many things asynchronously. There’s never been in our business this expectation that you would be available sitting at your desk from 9:00 to 5:00. We do nothing over the phone. In fact, if Ari ever calls me on the phone, I pick it up immediately and go, “What’s wrong?” He’s like, “Nothing. I was driving.”

What do you use for your communication internally?

We do a lot over Voxer. That’s probably our primary tool. It’s like a walkie-talkie, asynchronous communication app. We also have Slack. We do a little bit over Slack and we use Trello for project management so any project-related discussions will go over Trello. We have a synchronous meeting week that we do over Zoom.

They are pretty standard. Have you heard of an app called Marco Polo?

Yes. A friend turned me on to it.

It’s like Voxer but video.

I don’t love the video. I went through and I accepted friend requests on it. I was like, “I don’t want this person to see my real true crazy face.”

No. I wouldn’t want to be doing it with the whole world. There’s something there about doing it with your team that works out quite well. That’s pretty interesting to be able to use it. It’s an interesting tool. Talk about the lessons that you pulled out of West Point that you still work with, the lessons that you’ve learned in the military that you still use in the business world.

It’s been interesting because I feel having gone to West Point and worked with army officers there were a lot of skills that I never considered that unique until working with the rest of the world because all my classmates and all the people I was close with all had the same skillset. The first summer at West Point you start and they teach you. You have four responses so an upperclassman asks you a question, there are only four responses you can give, and it’s, “Yes, sir.” “No, sir.” “Sir, I do not understand.” “No excuse, sir.” That’s it. Those are the only things you can say which is a valuable lesson. I find in business, especially, there’ll be a project, “Here’s the result that we’re after.” You’re like, “Yes, sir.”

I was laughing about kids. Can we take that down to our kid-level?

We tried. It didn’t work so well. It’s like, “What can I say?”

Do you bring that into the business world?

Automating Business Strategies: Communication, project management, and process are the three primary areas where businesses struggle when it comes to systematization.

Yes. It’s like, “This is the deadline and we meet the deadline no matter what.” “This is the project. It gets done no matter what.” This isn’t to say that there are not things that come up but I’ve run into a lot. We hire contractors to do things, and they disappear off the face of the earth or, “This is going to be late.” Not to sound draconian like there are no excuses on why things go off the rails but I find that West Point and the army taught me that those become the exception way more than they become the rule. It’s not like, “I’m tired and I want to go to sleep. I don’t want to finish the project.” “No excuses. It’s time to finish the project.” The ability to look at a problem, assess it, come up with a solution and move in that direction is certainly a valuable skill set that has helped me in business.

How do you balance that out with this more or less a fair work-life balance approach that Ari brings to the table? How do you balance that or rationalize with it? That may be an assumption of mine, too. It’s an assumption that maybe he’s not that way in business. Maybe that’s the way he seems when I talk to him face to face.

I’ve had to learn to deal with people in their feelings a little bit more often and some of that a little bit more relaxed. I’ve had to loosen the reins a bit and I don’t want to say drop my standards but recognize that things can slow down some, but Ari is not that much like that in business. When it comes to the business, it’s funny because I’ll send him a seven-minute Voxer about a decision that I’m agonizing over and he’ll respond in three seconds. He’ll be like, “Do the second one.” I’ll be like, “You didn’t consider.” He’ll be like, “This is what you wanted. You wanted me to choose between these three things,” and he will. I’ve had to learn that he doesn’t need to give me his whole thought process behind it. I asked him for an answer and he’s like, “Here you go. It’s the second one. Drive on.”

Have you done any personality profiles with your leadership team?

We have. Kolbe is the big one for us. I rolled my eyes at it at first, but I have found it immensely illuminating.

What’s Ari’s Kolbe profile and what’s yours?

I can never remember the exact numbers but he has Quick Start and Fact Finder. He is as high Quick Start as one can get, as low Fact Finder as one can get and I am the complete opposite.

He’s probably a 4-3-9-3 or 4-3-10-3 or something and you’re an eight something?

Yeah. I’m a nine on that Fact Finder part and I am a one on that Quick Start part.

Have you guys ever done a call with Kolbe to learn how to work well with each other and talk about each of your profiles and how to work best together?

No, we should though.

I always call it a Kolbe A match. They have another term for it but if you send them an email, they’ll know exactly what it is. They do a 30 minute or one hour call for not much money and they’ll walk you through how to understand Ari’s Quick Start profile and he’ll understand how to leverage the Fact Finder profile. We have every member of our COO Alliance do the Kolbe profile and it’s amazing how every second command that we have in the COO Alliance is either a high Fact Finder or high Follow Thu which is all about systems and processes so they’re similar to you. Virtually every one of the CEOs has a high Quick Start.

I believe it.

They’re different.

It’s been an interesting learning experience for me and I put words in his mouth, I’d say for him to for us to learn to meet in the middle with those things. We work with a client. I’ll have to put a plug for her name, Sally Hogshead. I don’t know if you know Sally. She runs a company called How to Fascinate. She has a similar test and it’s this big matrix she gives you. It’s all color-coded. She did an event for us where all the attendees took this test and she mapped everybody on the chart. Every single person in the room was up in this upper quadrant of visionary, innovator or in that area. There was one person all the way on the other side on the bottom. I’m looking at mine and I’m like, “It’s me. I knew it. I knew there’s something wrong with me. I don’t fit in here. Everyone is so much smarter than me. They’re so full of ideas.”

Sally was going over it and she’s like, “Which one of you has this person on their team?” Ari’s like, “That’s me.” She’s like, “You’re lucky.” I’m like, “What?” She’s like, “You get all these people that are only ideas people in a room and it’s great. They come up with ideas all day long but if you don’t turn ideas into action, they’re just ideas.” That was game-changing for me in my role to recognize that I am different from Ari and different from our clients. There’s a lot of value in that.

You’re supposed to be different. The artist is different from the musician who is different from the engineer who is different from the mathematician who is different from the doctor like we’re supposed to be. We’re not supposed to do each other’s jobs but we have to learn how to get along, understand each other and leverage each other. That is what’s powerful about doing these personality profiles. You get to learn about each other. How have you learned to adapt your style?

Less about adapting yourself, how have you learned about working with someone Ari, who’s an entrepreneurial quick start, shoots from the hip, makes it up as he goes, fire, ready, aim? How have you learned that an idea in a minute and everything can be done quickly? How have you learned to work with someone like that? How has he learned to work with somebody who likes to ask a whole bunch of questions before they start something which can tend to drive the entrepreneur crazy, but needs to be done so they don’t come back to us seven times?

We created a worksheet that will teach our coaching program. We created a whole lesson in our coaching program about this where it’s a framework for having that conversation of, “Here’s my idea.” We talk about, “This is your idea. Here’s your intended outcome,” and we discuss. That’s his part and my part becomes, “When are we going to implement this idea?” “Not now, because we’re doing all these things.” “This quarter because lead gen is our focus on that quarter,” and turning the discussion into who should be responsible for that.

The key is to discuss the project, understand the project and then decide if your red, green, or yellow light. Green light is, “Yes. We’ll do it. We’ll put it in the plan. It might bump something but we’ll talk about that.” Yellow is, “We’re going to do it but not yet.” Red is, “We’re not doing it. Thanks for listening. I’m glad we talked through it.” Does that system work internally well?

It does, absolutely. I will give Ari a lot of credit. He has come a long way. He said this and I’m not sure if he’s the originator of this, “Entrepreneurs have two timeframes, now or not ever,” which is the complete opposite for people like me. I’m not like, “Here’s your idea. Let’s jump into it.” We’ve both come a long way to meet in the middle of, “This is an idea. This is a great idea. This is going to serve the business. I’m not going to drop everything I’m working on and change the direction of the team to do it like that.”

Can you give us some examples of some of the technology and automation that you’ve put in place in your business that allowed you to optimize and automate processes versus work harder and more?

Is in terms of the tools that we use or some of the automated systems?

Some of the automated systems. When this comes in, it triggers these two things and it does that. Give us a couple of examples so people understand. There are a lot of people out there that don’t even know what it is necessarily you’re talking about or that you guys do.

Automating Business Strategies: The ability to look at a problem, assess it, come up with a solution, and then move in that direction is certainly a valuable skill set.

We have a lot around content creation. Ari will do a Facebook Live. He’ll do a video of some kind. That’s his favorite. We use a tool called Repurpose.io that will take that Facebook Live and it will put it into our Facebook group. It’ll put it on YouTube. It’ll share it on our Facebook page. It also saves that file to a Dropbox folder which triggers a message to our virtual assistant who sends it to a content writing company that we use and they create an email out of it. When they are finished with it, an automated email always comes into our email that says, “This article is done.” We have an automation with Zapier that triggers off of that particular email that sends another email to our virtual assistant to tell her to go into ContentFly, pull out the article and cue it up in our email marketing client. It’s a Monday newsletter and then sets that to send.

Normally, that would be a whole bunch of people doing work, passing it to the next person, waiting for that person to get it started, the person forgetting about it, needing to follow up, that person having a delay. You’ve removed all of those steps in the process and automated those.

Absolutely. It takes Ari’s best ideas and it turns it into a bunch of different content, sends it everywhere with minimal button pushing and hands that need to be on it.

Do you still work with this mantra of stop, optimize, automate, and outsource?

It’s optimize, automate, and outsource.

I put the word stop in front, I’m like, “Do we even need to do it? Before we optimize it, can we stop doing it at all?” How have you grown as a leader over the years? You’ve been with the organization for years. How have you had to grow?

The biggest thing for me is learning to work with different types of people. With the military, there’s a lot of similarities between the people that you work with. Even as a brand new Second Lieutenant, you’ve gone through four years of training that prepares you to commission and to be in that role. The same thing is with your brand new Privates. When a brand new Private shows up in your unit, he’s not brand new or she’s not brand new. She’s gone through basic training. She’s gone through some advanced individual training. People that have a drastically different set of beliefs or mindset. They wash out. They don’t try in the first place. Business isn’t quite like that.

I hadn’t even thought of that. At every level in the military, everybody is pretty much similar, culturally, similar core values and they’ve all gone through similar amounts of training. You’ve got a base level of expectation that you can count on. In business, we don’t have that at all. We don’t know what the real experience is.

That has been a tricky one for me. I’m sure one of the members of my team who reads this laugh because she always gives me a hard time for being bad at feelings. I don’t want to talk about feelings. It’s business. This is work. Why are we talking about our feelings? It matters. That impacts the way people show up. It impacts their work, the way that they feel about things.

That has to be different from the military. You don’t praise people the success. Maybe this is a huge bias. As a civilian watching Taps, I got the feeling that you’re not allowed to show your feelings in the military and there’s not a lot of praise. You don’t praise people’s success. It’s very command and control. Is that true or is there praise? Is there the attaboy and the high fives and the cheering people on? Does that not exist or have a place?

My experience was there wasn’t a lot of that. I’m sure a lot of businesses do this. We’ve yet to get into a good routine of it but there was a regular schedule of performance evaluations. There’s a form and this is what we talk about. There was regular feedback.

When you’re raising your kids, we don’t wait until the end of the quarter to tell our kids how they’re doing. We cheer them on all the time. We tell them what they’re screwing up all the time. Is that different from the military to business?

I did not see a lot of that. My husband and I were talking about the military having a fantastically, hilarious array of insults that you could hurl upon people and some of which are not G-rated. Were both struck. If you said that to somebody at work, they would be aghast. There’s a veteran’s rock climbing group around here and my husband and I went to one of their meetups. I’ve never met these guys before in my life. There we are and one of the guys is climbing and I said something insulting to him, which was funny. All of us got the joke. We were like, “That’s acceptable here.” If you went to a group of strangers anywhere else and said, “Nice job, window licker.” They would be like, “What did you say to me?” I am terrible at compliments. People in our team, sometimes they need that. They need to know they’re doing a good job. I’ve almost had to automate that somewhere. I send myself a reminder, like, “Tell someone on the team they’re doing a good job.”

I I used to climb years ago. This was in 1991. I had got back out to this area where we climbed and we were setting up all of our routes and this guy walked by and he’s like, “I know you.” I’m like, “I’ve never met you before.” He goes, “Last week, on Sunday, you peeled off the rock and screamed like a twelve-year-old girl.” I’m like, “That was me. I don’t need that. Thanks for recognizing me.” Have you had your kids out climbing yet?

We got to do it with my six-year-old. We had got him into doing it. This veteran’s group happened to meet at the same time as his class. He loves it. It’s been good for him.

My sixteen-year-old is starting to do bouldering and he’s indoors. I want to get him outdoors. I want to show him bouldering. I’m like, “Get outside and do this stuff.” That’s amazing.

It’s scary. Since getting out of the military, I do not like heights. When I was in the military, I jumped out of planes. I rappelled out of helicopters because that’s what we were doing and you’re going to go. You’re going to jump because you have to jump. As older adults, it’s like, “We’re high up on this wall, aren’t we?”

It’s a bizarre feeling, for sure. If you were going to go back to your 22-year-old self, you’re graduating at West Point, what words of advice would you give yourself that now you know to be true but you wish you’d known back then?

I wish that I had known more about family life. I got married at 22. We had our first kid by 25. West Point, as it should, all you ever talked about was the army. The army is going to be a career. You’re going to be a future leader. America’s Army forever and ever. Even the few female officers that we had, I feel like nobody ever pulled us aside and be honest about kids and the amount of time that they’ll take and a husband and the amount of time he’ll take because he could never find his shoes he’s capable of. Where are his shoes? They’re in the shoe closet. It’s where they are.

They’re exactly where they were. My mom’s line was, “Your shoes are exactly where you left them when I put them back for you.”

“I don’t know. I didn’t wear them.” I would have thought through the future a little bit more knowing that those things would have taken time. The decision to get out of the army was a tough one for me. I was surprised when it wasn’t working out well for us. We have two small kids. We did back-to-back company commands. I got out of the army because I thought those were the only choices. Your choice is work or your choice is family and that’s it. Working with Ari, I had to relearn that isn’t true. I wish I knew that years ago that those things could balance. There were options. Family is going to take a lot of time but you can find or create opportunities that work with that. It’s not all or nothing. It’s not black and white.

It’s cool that you’re in an organization and with a leader who gets that as well. Courtney Waid, the COO for Less Doing, thanks very much for joining us on the Second In Command Podcast.

Thank you for having me.

I appreciate it.

Important Links:

• Less Doing
• Voxer
• Slack
• Trello
• Marco Polo
• Kolbe
• How to Fascinate
• Repurpose.io
• Zapier
• ContentFly

About Courtney Waid

Less Doing is a company that coaches successful entrepreneurs to make themselves more Replaceable in their business so they can focus on the work they love. Less Doing helps these entrepreneurs who have the opportunity in excess of what their infrastructure can support, find focus, flexibility, and freedom in their business. The methodology enables founders to become replaceable so they can scale their business. Their nine guiding principles are a comprehensive attack on overwhelm that offers guidance in three fundamental areas: Effective Communication, Project Management, and Process Perfection. 

Courtney holds degrees from the United States Military Academy at West Point and the George Washington University. A former military intelligence officer and Iraq war veteran, she currently lives outside Ft Worth, Texas, with her husband, 4 children, and a menagerie of farm animals.