Speaking Sessions

Mastering Delegation and Team Empowerment with Chris Kille

February 07, 2024 Philip Sessions Episode 177
Speaking Sessions
Mastering Delegation and Team Empowerment with Chris Kille
Show Notes Transcript Chapter Markers

Unlock the secret to scaling your business without burning out with Chris Kille, the entrepreneurial force behind Payment Pilot and EO Staff. Chris shares his blueprint for effective delegation, emphasizing the strategic leverage of global talent. Explore the impact of global executive assistants on Chris's credit card processing business, driving growth and efficiency. Gain insights on embracing opportunities, escaping micromanagement, and leveraging time studies for effective delegation. Learn to systemize processes with playbooks, make tough leadership decisions, and foster empowered teams.  Tune in for a wealth of time management strategies, team empowerment insights, and the essence of visionary leadership. Don't miss out on this enriching episode—join us for a transformative conversation!

NOTABLE QUOTES
"With the help of a remote team, we're able to...scale [and] grow." – Chris
"Get your things off the plate that you're not good at. Hiring somebody that...I can give a basic general direction, and it gets handled for me. So I can focus on the stuff that I like to do and  I'm good at." – Chris
"You're hiring [the right people] because they're better at something than you are.” – Chris
"If you have [a] playbook, you can systematize things." – Chris
"Hiring for results and trusting that they can get the thing done, and then reverse engineering it works really well." – Chris
“We will snap fire if somebody violates core values. 100 percent. Immediately. No hesitation. No questions asked. You don't want that cancer in your organization.”  – Chris
“I think a lot of business owners, a lot of leaders don't think about the cancer that can be created in your culture because you allow somebody to stay in. That doesn't fit those core values, is detrimental.” – Philip
“It's really the most respectful thing to do. Be very clear and direct and give multiple chances.”  – Philip
“Adding the checklist, that's where the accountability is, because it's crystal clear.” – Chris
“It's the 10-80-10 rule. You start the 10%, they do 80% of the work and then you come back and check it to make sure it's the way you want it.” – Chris 
“Learning to trust and develop things [with your virtual assistant] is a great foundation and a great building block.”  – Chris
“When you start to eliminate those distractions and [can] trust people around you to make sure that it's getting completed to your standard, then that allows you to focus and stay within your zone of genius.”  – Chris
“Entrepreneurs get into business for freedom.”  – Chris
“If you're unwilling or you don't know how to give up those things that need to be given up so you can focus again on moving the needle, two years from now, [you’re] still in the same position that you were.”  – Chris
“The best time to bring somebody on is when you're very, very busy because they can shadow you. They can see what's going on, how you do things and you're setting up the playbooks together.”  – Chris
“Every employee should bring ROI. It may not be dollar to dollar. It might be a time ROI or a customer retention ROI.”  – Chris
“People don't pay for information, they pay for implementation.”  – Chris 

RESOURCES
Chris
Website: https://www.chriskille.com/
Instagram: https://www.instagram.com/notchriskille/
LinkedIn: https://www.linkedin.com/in/chriskille/
Facebook: https://www.facebook.com/chris.kille.9?_rdc=1&_rdr

Philip
Digital Course: https://www.speakingsessions.com/digital-course
Instagram: https://www.instagram.com/iamphilipsessions/?hl=en
TikTok: https://www.tiktok.com/@philipsessions
Linkedin: https://www.linkedin.com/in/philip-sessions-b2986563/
Facebook: https://www.facebook.com/therealphilipsessions

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Philip Sessions:

What's going on, guys? Welcome back to another episode of the Speaking Sessions podcast. I have Chris Killie here. He is an entrepreneur and investor based in Frisco, texas, for now. He'll be moving here pretty soon and by the time this airs maybe he'll already be moved, but he's currently the CEO of a payment pilot where he provides credit card processing services to companies in the home services industry. He's also founded an EO staff, which is formerly Elevate Outsourcing a couple of years ago, and he specializes in providing high caliber senior level executive assistance and fractional video editing services to entrepreneurs and organizations.

Philip Sessions:

Over the last 20 years, he has been a part of several businesses in various industries like tech, finance, collections, transportation and animal care.

Philip Sessions:

Entrepreneurship is practically in his blood. Both of his parents run their own businesses and he's learned heaps from their wins and losses, which is really important. After trying his hand at different jobs, he took the plunge into his own ventures and it's been one of the best decisions he's ever made, and he's not looking back at all, and today we're really going to dive into delegation and both Chris and I around you know, obviously he's got the executive assistant business, but we know some other people that do executive systems, va's, virtual professionals, whatever you want to call them, people that you're getting to help you that more than likely are not in this country, but they may be in this country as well, but that delegation is such a difficult thing for people to understand, so we're going to dive heavily into delegation today. But, chris, I've talked enough about you from an intro perspective. Welcome to the show and give us a little bit more on you from our personal perspective.

Chris Kille:

Thanks, I appreciate you having me. Yeah, I mean, like I said, my name is Chris, or, like you said, my name is Chris and I'm out of Frisco right now. I've spent the last 20 years, you know, all over the country. I was in Tampa for about a decade, and then Charlotte as well, and moved to Frisco and looks like I'm probably going to be moving up to Boston, and I've had my hands in a lot of different ventures over the years. You know. My most recent one, as you had mentioned, is executive assistants for busy professionals founders, ceos, management teams, things like that where we specialize in placing high quality talent inside of businesses to free up time, you know, give space and allow people to do what they do best, which is their zone of genius, instead of getting bogged down into the details that we all have to face when we're running businesses or managing people.

Philip Sessions:

For short, and so what got you into this executive assistant field in the first place? Because this just seems crazy, especially a lot of people made from like Mexico or the Philippines or the Middle East. They're getting these assistants from these foreign countries, especially when you're talking about Middle East and Philippines, like over in Asia, it's very far away. So how in the world did you get into this in the first place?

Chris Kille:

Yeah, that's a really fun question. I actually scaled my payment processing company using them. I was at a conference eight years ago, nine years ago, in Charleston, south Carolina, and there was a gentleman that was up on stage and he was talking about delegating and he was talking about, you know, getting your team in place, and one of the things he mentioned was that for people that may not have the revenue, they may not have the profit, they may not have the money to hire somebody that's a high caliber person here in the States, there are lots of different options out there, like companies or countries like Mexico, like Costa Rica. You know we personally do everything in the Philippines, but, yeah, you can get really qualified people at a fraction of the cost.

Chris Kille:

And what I was able to do was take my credit card processing company right from mid, like I would say, low, to mid six figures and I was a one man shop right up to, you know, mid seven figures. You know we may probably in two, maybe three years, we'll hit eight figures, which is going to be great. But I did this and you know, now we have a full team, we're able to provide the level of service and support. We've got a great sales team it's. You know, we're humming right and firing on all cylinders now, and so that's with the help of a remote team, and because of that we're able to get out of our own way. Scale grow, and so not only do we have a great team of domestic people here, but also a great support team overseas.

Philip Sessions:

Yeah, man, that's, that's great to hear. And I know, actually scheduling this call, which was kind of cool, is you know we had talked back and forth about okay cool, yeah, we'd love to be on the podcast, and then your admin came in and really helped schedule things out, because that can be very tedious. Okay, let's go back and forth there. Oh, I need to pick a right time and I've talked with some other entrepreneurs that have those executive assistants and it's just like look, I don't know where I'm at half the time, so they take care of it. They look at my calendar or calendars and get something on there, and so I know when it's on my calendar I need to be there and I'll be there and everything. And so that was a very smooth process there.

Philip Sessions:

I know from the outside it probably sounds like oh, it's crazy. Like okay, you went talking with the actual guy and then you talked to the assistant. Now, like no, they were like hey, this is the assistant to Chris, let's get a time scheduled. And we went through and the English was perfect. Like if they wouldn't have told me it was them, I probably would have thought it was you, and so it's definitely something that's beneficial there and you mentioned the monetary side of things, how it helped you build a scale one. You didn't have to put out as much money because, yeah, hiring Americans can be very costly compared to other countries and everything but then being able to scale your business and make more money was a really cool thing as well.

Philip Sessions:

So how did it look hiring that first admin for you? Because a lot of business owners that I've talked to in the circles were in. They seem to really struggle with that. Very first admin is, oh, I'm just going to get them to start doing stuff and everything's up here in their head and they're like, yeah, that makes sense, like do this, this, this, this. But then the admins is like what do I need to do? And then it almost feels more of a chore and you might as well do it yourself. So tell me about that first experience you had hiring an admin, and then let's go into like how we can make that first experience good for other people instead of like it's a second job on top of the 500 other jobs as a solo entrepreneur that you have.

Chris Kille:

Yeah, that's the biggest mistake that we see too is you know people. They don't know what they want. They know they think they need one. They're like, hey, this is sexy. I just heard this term, virtual assistant, let's get one.

Chris Kille:

So not only is it incredibly difficult to find a qualified one to do the pre screens, especially if you don't know what you're doing. For me, it took me over a year to find my first one because I was stubborn. I didn't hire an agency, which I should have done. In the long run, it worked out, because now I know how to do it and I was actually able to start another business because of it, which I probably had. I have hired an agency I wouldn't have been able to do, but you know again, that's very challenging to find somebody that's qualified. Even then, whenever you hired them and bring them on, you got to know where to start, and that's where I see a lot of people. You know they make mistakes about it and they don't know what they want going in, and so what we've been able to do is dial in some exercises that we do, whether you're going to be a client and whether we're just having a conversation.

Chris Kille:

There are some things that you know, for instance, like a time study, is a great one, where you actually, you know, take a piece of paper or your notebook or whatever. I don't know how. You know everybody's different from me. I carry the paper with me everywhere I go. If I can touch my to-do list every day, then that's something. That that is you know something about me. Having it in my hand really helps. But, you know, a time study is a great opportunity to do that, where every hour, you know, you set an alarm and you write down what it is that you did, and then you know you're able to rate it on a scale of one to three hey, do I like doing this, do I hate doing this, or or is this something that's indifferent to me? And then, from there, after you do it for about a week you know we actually recommend two weeks, but one week's a good, you know, sample size that you can get, you can look down through and you could say, okay, here are the things that I spend a lot of time doing that I didn't even realize I don't like doing, or maybe I'm not good at them, and so that's a great place to start.

Chris Kille:

But what I found is, with most entrepreneurs. We're bad at organization, we're bad at it, we love to over commit to things, right, we love saying, yes, yes, I can do that, yes, I can do that. And then you're like, oh my shit, where'd my day go. And so, getting somebody in that datekeeper type position that can keep you focused on the real tasks, that hand, keep you away from the shiny objects, and, like you were saying, you know, it's so much easier. I just say, hey, faye, this person wants to meet with me. I connect him via email or you know, sometimes you'll even go in my inbox and just you know and handle everything again. You know, hey, this is Faye, chris's assistant. He's kind of busy right now, but I'm going to go ahead and coordinate, make sure that you know, make sure that you have what you need and make sure that he's there when you need him. So it's a great way to start. And then, obviously, you can grow from there. But you know, you kind of got to crawl before you can walk.

Philip Sessions:

Yeah, and I like that time study too. Too many of us don't do that and that's something we should continually do in the first place, and if you hear that out, I like that you say the three things you like, you don't like, and then you're indifferent about. And so of those three, obviously the like will probably keep. But what should we delegate? The things we don't like or the things that we're indifferent about first, what do you think your, what's your perspective on that?

Chris Kille:

Well, so first do you want to get off your plate the things that you really don't like doing right, because you tend to procrastinate those and then also get things off. Get your things off the plate that you're not good at right. So for me I should not be doing graphic design because I'm you know I can. I could spend six months practicing and still be well below average, as opposed to hiring somebody that can come in. I don't have to think about it anymore. I give a basic general direction, right, and it gets handled for me. I don't have to think about it. So now I can focus on the stuff that I like to do and then I'm good at.

Philip Sessions:

Okay, and so then now we take this. So we've done time study, we decided, okay, I don't like these things, I'm going to hand them off to somebody or I'm just terrible at them. I'm going to hand them off to somebody, but I'm terrible at it, especially as let's talk, like you know, video editing. That's that's one that's very popular that I've seen. I use a VA myself for that, but other people as well for video editing.

Philip Sessions:

Why can't tell you a process necessarily like hey, do the video edits this way? So how do you go about communicating the way that you want something to be done and we can use video editing as the example, if we want but doing something, delegating something we don't know exactly how to do to somebody that maybe we don't know that well, how do we go about that communication process to then delegate that effectively to them and not make that something? We're constantly having to check over them on every single piece or having to update them all the time, because they're constantly asking questions because we didn't give them enough information to actually do their job.

Chris Kille:

Yeah, when it comes to delegating, this is something that I have learned recently very recently actually. As founders, we tend to micromanage things because we want them, perfect, right, we want it, and then, and a lot of times, we're bad at actually enunciating and communicating exactly what it is that we're looking for. So what I have found is when you do results based so, instead of saying, hey, mr Video Editor, I don't know how to do this job, but I want you to do one, two, three step four, step five rather than saying, hey, here's an example of something that I like, here's the point that I'm trying to get across and then leaving it at that, because, remember, if you're hiring the right people, they're going to be mid to senior level, and you're hiring them because they're better at something than you are. So then what you do is you monitor their output and you can tweak from there hey, this is almost there, I'm trying to get the point across a little better and then you can really dial it in that way. And then, from there, once you're comfortable, or once you have the end results that you're looking for consistently, you can have them build out a playbook, and a playbook is now okay. Now tell me, step by step, what you did. The reason for that is because now you can systematize things if you need to hire another one, or if they quit or if you fire them, whatever. Now you have that playbook that the next person that comes in you can say hey, here's how we do things, system process oriented, so you are now able to onboard somebody that much faster. You can still give the direction that you want, but now you have a little bit of a competency of how those things are done. So that's typically how we do it is.

Chris Kille:

We were results oriented. I don't want to sit there and hold your hand. Recently, we had to let somebody that was in a higher level position go because we were doing an email campaign and we said, hey, you know, we need this, this is the end result that we're trying to do. And he kept reaching out asking us how to write emails. We're like, hey, you're not in the right seat and this is not, we're not looking for this. Like, this is what we need. If I wanted to, if I wanted to write the emails, I would have done it myself. And so you know, what we found is hiring for results and trusting that they can get the thing done and then reverse engineering, for it works, really works, really well.

Philip Sessions:

And that similar thing happened to me for a social media manager that hired. She said she knew the strategy, all this stuff. I'm like, oh great, and there was definitely some things on my end that I could have done better, for sure. So it's definitely not a hundred percent her. But as we got talking, he's like every step of the way is I'm like, hey, here's the content, here's what we want to do. I need you to create captions for this. Let's let's get a schedule together, let's lay this out like an all review it and stuff.

Philip Sessions:

But I'm looking for you to help me with the strategy behind that. What does that look like? Because this is your core focus. And she would ask me well, when do you want me to schedule this? When do you want me to do that? I'm like we've discussed this, We've talked about the calendar, even because I was like I understand that we went through and made a calendar. And then it was like OK, here's the content, I have Start putting captions. And she made captions OK, well, when do you want to put on the calendar? I like that that's supposed to be your job. Like if I just wanted somebody to post for me, I would have hired somebody just to post for me.

Chris Kille:

Make a lot less money.

Philip Sessions:

Yeah, yeah, exactly so it's just, it's interesting how that does happen. But again, that comes out of communication and help him understand that expectation. So it goes both ways. So we need to explain exactly what we need, but then they also need to say what their actual skill set is and everything, and so.

Philip Sessions:

I like that. You brought that up and that's and it is a tough thing which, speaking of which, getting rid of somebody, whether a VA or a person, somebody that's like I mean they're all people, but somebody that's in person, I feel like that's a little bit harder because they're they're right there in the office with you. How did you go about letting that person go? I mean, I'm kind of curious, and I'm sure you probably, you've probably done this multiple times. You probably help clients do that. So how do you kind of work through that to let people go? I think it's an important skill to know about.

Chris Kille:

It's all about expectations, so we try to not snap fire. We will snap fire if somebody violates core values 100 percent, immediately, no hesitation, no questions asked. You don't want that cancer in your organization. However, in a situation like that, where somebody continues to make mistakes, it is about making sure that expectations are being communicated and that standards are being upheld. And so you know you can have that conversation repeatedly with somebody. And then once the way that I look at it is once I view somebody on my team as a liability ie, I can't trust them anymore.

Chris Kille:

Right, I give one more chance and I'm very forthcoming. You know we're we're coming to a point in our relationship that that this is now creating more work for me than it was before I hired you. Here are my expectations. Right, I'm going to give you another chance. You know, please correct this, or we're going to have to make a change. And you know I've had situations where they're like, oh, ok, cool, sorry, I didn't realize that you wanted it that way, my bad. Or you know, what I like to do as a leader is always take responsibility. Hey, I may not have explained this the right way to you, so let's do it again. Right, and you know, and, at the end of the day, if they still continue to make the same mistakes. It's as simple as you know. Look, I just don't think this is a fit, I don't think our expectations, I don't think what we agreed to do is, you know, together is there, and so you know it's time for you to go be successful somewhere else.

Philip Sessions:

Hmm, I like those two points. So those are so important, and especially the first one. I think a lot of business owners, a lot of leaders don't think about the cancer that can be created in your culture because you allow somebody to stay in. That doesn't fit those core values, is detrimental. It doesn't matter if they are a subpar performer or an over performer, and those are the ones that tend to be able to skate by oh, we'll let it, we'll let it go by, it's going to be okay, we'll, we'll work through it, because they're just so great. I promise the output of your team will be probably tenfold I mean, it's definitely going to be double or triple the output when you get rid of that cancerous person. Because they see that well, they're not doing what they're supposed to do or they don't treat people right. I don't want to be around here. I don't want to be around here. I don't want to be around here. What does it matter what I do? Because it clearly this person can be whoever they want to be and go against the company's values, and they're still here. So they're going to start doing the same thing. And, yeah, it creates that cancer, like you said, and that's such an important thing, but the other side, that clear and very direct communication, especially those in the southern states. It's a difficult thing to do, but it's really the most respectful thing to do is be very clear and direct and give multiple chances to I like that.

Philip Sessions:

You mentioned that as well. Like, hey, we talked about it, I took ownership, said hey. I may have not explained this very clearly, so let me make sure I explain it again. Here are our expectations, and you set that up up front. A lot of leaders don't do that as well, because we're used to, especially as a small business owner. We're used to Well, we just take care of it. It's in our mind, we figure it out and we're just working through it. A lot of people need to be told very explicitly what to do. Yeah, because they're not exactly sure what to do, and then it's not their business. So, one, they don't care about it enough. But then, two, they also aren't thinking about the big picture. They don't see the big picture. They're just doing this one little thing. So you need to help them understand what that one little thing is and how it fits in with that big picture.

Chris Kille:

Yeah, and playbooks are what solve that. So Just to give you like an example, so let's say it is a, let's say it's a responding to an email. That's something that a lot of people, a lot of business owners, have a really hard time giving up. And whenever I come in and I say, hey, we can have somebody that can manage your inbox because it's managing it right, clean it up, get rid of the junk right, organized things so that way, like so. For instance, I check my email twice a day, all right, and I usually have no more than five or six emails that require my attention for me to actually do something on my, you know assistant, faye will go in. She's in there, you know, like basically the entire day when we receive email. She's and you've seen this before when you send me an email, 99% of the time You're going to get a reply within a couple of minutes. Hey guys, this is Faye, chris's assistant. He's a little bit busy right now. If it's something that she can handle, meaning if it's just a basic scheduling or something that really doesn't require my attention, she'll take care of it right. If it's something that she's unsure of or it definitely needs to be handled or responded to by me. Then it gets categorized into something else.

Chris Kille:

But the way that we got to that was we created what's called a playbook, so, where I showed her the way that I like to run my inbox. I've recorded it. I did a screen grab so we you can use loom, or I personally use screencast a matik, which is now Screencast, I believe, or screen panel, I think it's what it's called and so I show her how to do it and I'm speaking the entire time. And then what I do is and you can, actually the best part is, you can have your executive assistant do it from there Then what they do is they actually write out the step by step, right, and then write out the cadence how frequently does this need to be done? And then at the bottom we have a checklist.

Chris Kille:

So Once like so, now it's like if it's not done properly, you just go back to the playbook and you're like hey, the videos here, this is exactly how to do it. Here's the step by step. And then here's the checklist when is the? Where did that breakdown happen? And how we, how do we make sure it doesn't happen again? And so adding the checklist in is something that a lot of people miss or forget to do, and that's the goal. That's where the accountability is, because it's hey, it's crystal clear. You see it, you read it, you can hear it, and then there's something to check it by and you know. So it's. You know why? Why wasn't this completed?

Philip Sessions:

Hmm, I like that and to me, just my engineering Mind, I think like maybe I created a checklist first and then I can go back and fill in the details on all those things. It says playbook, and I think that's just your version of basically a SOP or standard operating procedure, by, like the playbook Concept. So how do you come about that? Because if you've never written any SOPs before playbook, that's definitely something difficult to start doing and I like that. You, yeah, I forgot what it was, but as a screencast or whatever loomer screen as well.

Philip Sessions:

Yeah, but how do you go about Creating that playbook in the first place? Because that seems like a daunting task and we think about what email? What's just an email? But that's like, oh wait, well, there's this. And you got to say, hey, do we use Gmail? Do we do we use outlook? What do we use like? What's that app or the website that we need to go to? And then the categorization, like you were saying. So how do you go about really mapping out what that playbook looks like and then filling in the details?

Chris Kille:

Yeah, you just follow that framework that I gave you and then you just go about your day, especially in the beginning. You just go about your day and you record stuff as you're doing it and that's, and then you you give it to your, your assistant, you can get, and, again, the framework, and then they go through and they create it for you and then you check it. So it's the 1080 10 rule right, you start the 10%, they do 80% of the work and then you come back and check it to make sure it's the way you want it. And that's where the feedback and the magic actually happens. Then you can file it and then, in theory, you shouldn't have to do it again. So in, for instance, we can stay on the email thing.

Chris Kille:

There may be a template that needs to be created for that. You know again, mine is. You know, hey, this is. This is Faye, chris's assistant. He's jammed up today, but I wanted to make sure you got a response to this immediately. You know again, if it's something that she can handle, I went back and I checked with Chris real quick and boom, here's a quick answer for you, and then it moves on, or if it's something that's more, you know, hey, I this, this is, this is more of a a matter that's gonna definitely involve him. So we flagged this email. So tonight or this evening or tomorrow morning, whenever, or you can even say his first earliest convenience he's gonna take a look at this and we'll have a prompt response for you. But the main thing is the person understands that that email has been acknowledged and the expectation as to be has been set as to when they should receive a reply.

Philip Sessions:

Hmm, yeah, I like that, as that's a great framework there, for sure. And the 10-80-10 rule. I don't think I've heard that rule before, so is that something you came up with or read somewhere? I'm curious on that.

Chris Kille:

Yeah, it's pretty common actually. I've seen it 20, 60, 20, 10, 80, 10, you know it's, it's. You know you can even kind of go into the 80% is better than better than you know 80% done it's better than 100% and not done. So you know, no, normally most of the time people aren't gonna be able to do things as good as you, but you know you get them started, you know. You know I set the expectation get the, get the ball rolling, let you do the majority of the work, that I come back and I mean that's what an assistance there for and if you have a good one.

Chris Kille:

As that relationship matures and grows, it's less and less the more, the more you can count on them to know that they know the way that you do things, they understand the way your brain works and they've been around long enough that they know your systems. They know how you because she's in my email, she sees the way I respond to everything. It's it's almost like you know she's constantly learning as to my interactions and and how I you know and the decisions that I would make and in the beginning to you can even go back and you can run scenarios. All right, you know, faye, we have this in my inbox right now. How do you think I should reply to this? And then you use that as coaching to where it's okay.

Chris Kille:

Well, you know what? That's pretty close, but here's what I would do, or that's spot-on, that's perfect, that's great. You know, and learning to trust and develop things like that is where I see a lot of people. That's a great foundation and a great building block. That, well, because most people are slaves to their email a lot of times, I'm sure I don't know, I'm sure not, but your, your emails Might be up in a tab right now and every time, every like every minute, a couple minutes or so you click back Just to check on it.

Chris Kille:

Right, that's like the Pavlov you know Pavlov's dog with the bell. It's like oh, somebody said an email, I got a reply to it. 99% of the time it's not an urgent, you know thing. If it's urgent, they're gonna pick up the phone and call you and, and even then I have a I have a hack for that, you know with. Do not disturb that, we can talk about later. But but you know it's, it's just making sure that your day stays optimized so you can stay focused and locked in on what it is that you should be doing, that you're excellent at doing, that's gonna Generate revenue or maintain revenue or keep you know, keep the focus on what it is, instead of the shiny object syndrome that a lot of us get. When you really start to eliminate those Distractions and are able to trust people around you to make sure that it's getting completed to your standard, then that really allows you to focus and stay within your zone of genius.

Philip Sessions:

Yes, and that's why we need to delegate in everything. And you mentioned about the getting them to do like 80% of the work and check on over and stuff, and it couldn't help but think about what we kind of talked a little bit about earlier. As entrepreneurs, we hate to give up control because we want everything to be Perfect. So at what point do you feel, maybe percentage wise, if you kind of have something, do you feel like is quote-unquote good enough To be able to delegate that work to somebody and maybe you're not quite checking over anymore? Of course we want to spot check here in there. We don't ever want to completely get rid of that unless we have somebody else in place, like another manager, to manage people, stuff like that.

Philip Sessions:

But how do we go about, like when we go to delegate? Where's that point where it's like, okay, it's good enough, because it's never gonna be us, and Quite frankly, there's there's things that we really aren't good enough at, like going back to video editing, like you and I both are Not good video editors, so somebody is gonna be leaps and bounds better than us, yeah, but when it's something that we can do pretty well let's let's say, sales, for instance that's something that's probably given up last as a business owner. But once you start giving up that control of being the only salesperson in your organization, how do you go about making sure that it's good enough that they're taking over and you don't need to just hold onto it for dear life?

Chris Kille:

so we use sales as an example because that's usually you can say that you can go back and you can review the tapes. You know if you, if you hand off sales, and Sometimes you're gonna find you know if you can close out a 60% and you can find somebody that can do it at 45, hey, that's, that's still pretty dang good, but it's not 60. So it's, it's a forest through the trees you know are am I able to? Let's just use it as out of every 10 leads, I can usually close six, but the person that I hired can only do four. Well, how much time am I freeing up by not doing those six calls, not doing the follow-ups, not doing? And one of the ways that you can bring somebody on is an assistant, where they're shadowing you every step of the way and again going back to playbooks. Now they understand your workflow the way that they do and you may actually find somebody that outshines you. But again, good enough in order to free up your time to go find that next major referral partner. Or maybe the sales is something you never get rid of. Maybe you're in a really high ticket, super specialized industry that really only you can sell it, or maybe you're at a point where this is something you really like doing and you've gotten everything else off of your plate. I mean, it's just again. It's all going to be based on feel.

Chris Kille:

I personally believe that everything in your business should be delegated. At some point you should be able to. And there's like, if you look at Richard Branson, for example, right, he's an extreme example of this, but he's got over 100 companies that he owns not companies that he's invested in, companies that he owns and actively operates right, and they say his average day is less than an hour and a half of meetings and he's not picking up the phone and calling. Right, he's doing what he wants to do hanging out at his island or flying one of his planes or spaceship or whatever, because he's got the right people in place that he hired, that he knows, likes and trusts to be able to operate at a level that may not be Richard Branson level, but it's close enough to where the business is moving and he has freed up the time to do what he wants to do. Because, at the end of the day, entrepreneurs get into and I say entrepreneurs, right, entrepreneurs get into business for freedom, right, you're like I'm going to own my own business and I'm going to go sit on the beach somewhere.

Chris Kille:

How often does that actually happen? I would venture less than 1% of the time. I would actually go even farther, to say more than 50% of the time. You now just have a job that you just happen to be writing a paycheck to yourself, and maybe you're working 100 hours a week now instead of 40, but you still have the freedom and that's because you're unwilling or you don't know how to give up those things that need to be given up so you can focus again on moving the needle and instead of just being stuck. We always use the analogy working in your job instead of on it, and that's where you see the people that are truly experts at delegating and bringing qualified people onto the team, as opposed to those that refuse to give up the reins. And two years from now, they're still in the same position that they were, and it's just because they won't let go.

Philip Sessions:

Yeah, now let's talk to this person that maybe they've already hired a couple of people, maybe they've never hired anybody at all and they're on this fence because, whether it be a VA or a B person that's in the States, that is obviously more expensive there. They're just afraid to make that investment because they're not sure what that return can be for them. What are some of the objections that you can give, or rebuttals that you can give, to this? This major objection to help them get over that edge? Because that's the scary place to be, because I'm going to put this money out, especially if you think of an admin. Well, they're not a salesperson, so they're not bringing money in the door, they're technically costing me money. How would you rebuttal this objection that may come up from people right now in their minds?

Chris Kille:

You get that all the time. I get the. You know what? I'm so busy right now, I can't bring this person on, and I always argue you can't afford to, not If you're so busy right now or I don't have the work for it right now. I promise you, if you have it, if you look at it that way and we talk in 12 months from now, I promise you you will be in that same exact spot that you are right now.

Chris Kille:

Actually, the best time to bring somebody on is when you're very, very busy. It's because they can actually shadow you. They can see what's going on, how you do things. You're setting up the playbooks together. You may sit on. So one of my sales reps at PaymentPilot as she brings on, she has multiple assistants and as she brings them on, they sit on Zoom with her all day long. She just works, she does her thing and they watch. But now it's at the point where they're not the one shadowing her. They shadow one of her assistants and so they just sit there and they observe for like a week, a week and a half, and they ask a lot of questions and they go through and they're creating the playbooks, and the playbooks are already in place for a lot of them, but it's easier to bring this person on.

Chris Kille:

And then when you look at any employee, whether they're domestic, overseas, part-time, full-time contract whatever if you are looking at them as a bottom line expense, you are completely backwards on it. Every employee should bring ROI. It may not be a dollar to dollar, but it might be a time ROI. It might be a customer retention ROI. It might be something that may not directly translate into actual dollars in your pocket, but it allows. You know it is necessary in the business and you know we see that I just don't have the money for it right now. Okay, so, especially for a remote person, you're talking less than a couple thousand dollars a month usually, or give or take right in that area. You know a hundred thousand dollar a person here in the States for 25,000 or less over in the Philippines, and you're going to sit here and tell me that you can't afford it right now because you're overworking yourself.

Chris Kille:

Whereas what if I could get you? You know what, if you could actually go out and set a couple more appointments for yourself each week, close a couple more deals? What does that look like? So that's the main. That's the main objection that we get People reach out because they want, they're ready for it, and then they start thinking, oh, this is going to be too much work, this is going to be, this is going to be so hard. And in reality, if you go into anything with a plan, it's a lot easier to execute as opposed to going in and you don't know what's going on. And so that's where hiring a competent firm if you not. Hey, if you want to do it yourself, more than welcome to. I promise you it's very hard, it's going to take a lot of time, right? So that objection might be valid at that point.

Philip Sessions:

Yeah, the time that you don't have.

Chris Kille:

Yeah, exactly, I'm just. You know it's another job. Do you know how to be a recruiter? No, good luck, right. So you know that's when hiring a competent and experienced firm to come and do all that legwork with you, help you onboard, help you train and develop, but then, most importantly, being able to hire to a core set of competencies, right, where you're not just going to get some guy we see this all the time too where people think that they're going to get a superhero for like three bucks an hour.

Chris Kille:

It's not going to happen. Can you get a virtual assistant for three bucks an hour? Absolutely. Are you going to end up spending? You know, yeah, it's like you get what. You absolutely get what you pay for. Maybe, if you're looking for somebody just day to entry can just grind stuff out, cool, no problem. Step one, step two, step three, step four here's your job, here's your login, go do it. But when you're looking for somebody that's actually really going to help you be able to collaborate and clear up your mind and be able to focus on the things that you can delegate real life stuff to, you need somebody that's qualified and odds are you're probably not going to be able to find it them, so yourself, it's going to be very, very difficult.

Philip Sessions:

Yeah, you're exactly right, and that's why there's recruiters at every company. That's why there's companies that are literally just recruiting companies, because that is a job in itself. And as a small business owner, we don't think like that and I truly believe the more we can think more like a corporation as a small business owner, the better off we're going to be, because we're going to see those processes they put in place. And there's a reason why all those are in place, there's a reason why they have so many people doing so many different individual things, and the more that we can start delegating and let somebody focus on one thing individually, the better that piece is going to be. And so the last question here on delegation what would you suggest be the first thing that somebody tries to delegate? Now, this may be a little bit different for everybody, but just kind of, in your experience, whatever you've seen, that has been the most beneficial, the most return on investment for delegating X job out.

Chris Kille:

Quick and dirty calendar and time yeah.

Philip Sessions:

Calendar and time.

Chris Kille:

Calendar. That's where your time is. You have to guard your time. I'm sorry. Calendar and email that's what I that's the, that's where usually your biggest time sucks are going back and forth. It's the.

Chris Kille:

It's the one that people are most afraid of. But when you realize that you're, you've got them on a leash when it comes to email, they're you're not giving up your email. You're not like saying, hey, I'm never going to answer people. Oh, you're going to. They're going to answer the wrong way, cool, put them in a position where they're not answering anything. You know, if you still want to respond to every single email, that's cool. Fine, no problem.

Chris Kille:

But at least have somebody organize it for you to where you can come in and you can sit down and instead of it being an hour several times a day or you know it's, instead of it being this process, you can sit down. Chris, here are the things that require your attention. I unsubscribe you or I categorize 400 junk emails for you today. Right, they're right there if you want to look at them. But you don't have to look at them if you don't want to, I don't think they're relevant. But if you want to, they're in this folder. Go ahead and have a look.

Chris Kille:

Here are the things that actually require your attention right now. And then you're able to come in and that's it. Now, instead of having it be an hour process, you may be in and out, like I said, for me it's like five, 10 minutes twice a day. Boom, boom, boom, boom, boom. And then guess what I'm done? And then protecting your calendar, having them screen people that hop on, having them actually go back and forth with well, no, that time doesn't work for me. Does it work for that? Those are the two easiest things that you can do right away. And then, as your time study. Again, that's when you start thinking what are the ones that I hate the most coming out of the time study? Well, what are the things that I absolutely need the most? And that is when you start just kind of working your way up from most important to least important.

Philip Sessions:

I like that and I agree, I think, the email and calendar. I spent a lot of time on that. I know a lot of other people spend a lot of time on that. And then the worst part is you feel like you've done something very productive and it's a needed thing in business Right, but is it needed that you do that? And, like you said, that's the biggest return on your time, getting so much time back to be able to actually do things that are truly going to help move the needle forward in the business, such as sales.

Chris Kille:

I come to a report every day. It's called an Action Items Report, so it has a list of important stuff that I have to do that day. It has a list of all of my meetings. It has a dashboard for both of my companies that have balances, bank balances, bills that are going out that day, money that is owed to us. It'll have our scorecards, like an abbreviated version of the daily activity reports and scorecards from all of my departments, right, and then I can click down into the different persons Anything that needs to be escalated to me that I need to chime in on.

Chris Kille:

So I can look at this one dashboard. I come in, I'm like go through it. I'm like done, cool, awesome. So now and then here's the best part I'm not replying to that email. So I pull my screencast up Okay, I record the screen and I got my microphone and I go through and I just answer the questions, everything that needs to be answered, like, okay, number three, here's the answer to that doom. And then, once I'm done, I click save, I send the link to Faye and she does it all.

Chris Kille:

So now I have, I know exactly what's going on in my day. That day I know everything that needs to be brought to my attention. All of my finances, all of all the the important metrics that I need to see to operate my business from a high level are waiting for me every single morning when I wake up, that inbox is at zero, right, I don't have any stress when I would come in. Here's the information that I need to run my business. And now, hey, here are the priorities that we set, whether it's quarterly, you know. Weekly, monthly, quarterly, annual goals, you know. And then you can have the progress bars, you know, if you want to do them that way.

Chris Kille:

Now I know what I'm focused on. I'm not worried about any of that other stuff that used to eat up a couple hours of my day. Every day I leave I feel like I got something accomplished, even if I didn't do anything that day. There's days that I don't do anything. I just checked my email, I answered the questions, and then I go, go play golf, or you know, or I go. Whatever it is I want to do, you know it, but everything is. My businesses are moving forward every single day because I have the information in front of me on a daily basis that I'm able to make educated decisions on quickly and then move on about my day.

Philip Sessions:

Yeah, and the delegation that you did. So the people that can do the work are actually doing that work too, which is place all of us entrepreneurs want to be, so make sure that you are delegating the tasks that you can as you can. This is not an overnight process. This can take years to do, and We'll take years not just can, it will take years to do there.

Chris Kille:

Well, I would. I would disagree with you there. If you have the right setup and if you, if you're working with the right company, they're gonna give you the tools to compress that time. So what took me a year to figure out? Right, I might be able to show you, to get it done in a week, and then all of a sudden, now you're it's again. It's just like hiring a coach. You hire somebody who's been there before. They're gonna show you the path and instead of you having to figure out where the booby traps are and things like that yourself, now you have that path to action. You have the tools you have.

Chris Kille:

So when somebody comes on with me, not only are we doing all that upfront, you know screening and things like that but we've got worksheets, we've got examples, we've got videos. We have all these things that are ongoing training. So not only Do we provide free trainings for people in our Facebook group right, we do it twice a week the free trainings that are about around soft skills, and then also you know applications and and ways that you can you or your virtual assistant, you know, if you're having through somebody else, can come in and learn absolutely free. We have an ongoing training group inside of our private group, that is for active clients, again, two times a week. It's very similar to what we do in the free group, but it's that we do a lot of deep dive. There's a lot more worksheets, there's a lot more resources there to help you implement. And then the other thing that we started doing is we we figured out that using a Facebook group to recruit is good. So now when those entry level people come in that may not have the skills that they need to go get a good job, we're doing once a week training for them, absolutely free. We're gonna.

Chris Kille:

So what we found is we're able to now recruit from that as well. So everybody's winning because we are you know, I don't mind showing people exactly what we're doing. It's not proprietary information, it's not like we have a patent on it or any type of you know workflow that we Invented ourselves. What we did was we took information that's readily out there. We have organized it and made it easily actionable, and we do and we give it away for free. Do we get business away from? You know, absolutely. We get a lot of business from it, because people they don't pay for him and they don't pay for information. They pay for implementation.

Chris Kille:

We'll give you all you want, but how many times like. I give you an example with Alex Hormozzi. How many people, if they, if he was like, if he made a post that was like I am going to take on five clients right now to help with sales, right Is he would break the internet if he did that, right I mean?

Chris Kille:

honestly every single person of us would be like me, me, me, me, me. But what if he only covered what he did in his books? Nothing outside of that doesn't matter. His books are there, they're free, or they're 20 bucks or whatever. He's giving you the information, but you're paying to have somebody hold you accountable and implement, and that's exactly what we do.

Philip Sessions:

Yep, exactly exactly. That's such a great point in. Chris. I appreciate you coming on sharing with us about how to delegate, how to communicate through that, what that looks like. There's so much to it and in your right it can be easy, especially we have somebody like you essentially coaching you through that on how to actually delegate properly, and so if they want to follow you, get in touch with you, really learn about the group and how to delegate better. Where's the best place for them to reach out?

Chris Kille:

Sure, yeah, I would say the easiest place where you're gonna be able to find all my resources. You're gonna be able to find acts links us, links to my group, links to sales reps for the EO staff, links for payment pilot you know it's gonna be Chris killiecom. And then there's a you know there's. You can navigate the site from there. There's a lot of, there's a lot of free resources on there.

Philip Sessions:

Awesome. Well, chris, thank you so much for coming on and sharing this immense value on the art of delegation.

Chris Kille:

Cool. Thank you so much for having me you.

Chris's background and personal info
Mastering executive assistance
Streamlining your first VA hiring process
Delegation and communication expertise
Clear communication, expectations, and letting go
Crafting playbooks, checklists, and categorization for growth
Understanding the 10-80-10 Rule
Navigating delegation and boundaries in business sales
Wise investments in hiring a VA
Efficient time management and delegation strategies
The art of delegation and accountability
How to connect with Chris