Delegation in Business Management: Buy Back Your Time Through Delegation with Chris Kille

Episode 15: Buy Back Your Time Through Delegation with Chris Kille


 What’s up everybody, we are back with another awesome episode, this time featuring my friend and entrepreneur, Chris Kille, owner of EO Staff.

We kick things off with Chris recounting a dangerous tale from his door-to-door days in the credit card processing industry, where a run-of-the-mill sales call spirals into a scene involving a wine bottle and a shattered storefront. His story isn't just a wild ride—it's a gateway to discussing how to weather the storm of rejection and keep your spirits high through humor and perseverance. 

Transitioning from anecdote to actionable advice, we unpack the transformative art of delegation and its critical role in scaling your business. The conversation takes a turn towards the personal, exploring how managing everything solo can take a mental toll and how enlisting help can open up a world of opportunity for growth.

You'll get the lowdown on identifying which tasks to hand off and the secrets to ensuring a smooth transition. We dive into the nitty-gritty of efficient email management and share insights on the power of basics and teamwork over tech reliance.

By the end of this episode, you'll be ready to assign monetary values to your daily tasks and begin the journey towards reclaiming your time for the things that truly matter.

Key Moments:

-Re-live Chris’s crazy sales story.

-Always be ready for what they might throw at you!

-Chris’s secret sales weapon - indifference.

-The key to opening up space, staying sane, and creating growth opportunity is delegation.

-Actionable steps you can take to begin the delegation process.


Drewbie Wilson (00:03:28):

Hey, what's up everybody? Welcome back to Call the Damn Leads, the sales show by sales professionals for sales professionals. I'm your host, Drewbie Wilson. With more than two decades in sales, I've been through it, seen it, and heard a lot about it. Now I'm bringing it to you, my favorite community in the world, the sales profession.

Let's be honest, this is the coolest job on the planet. It gives us a chance to live any life we want, as long as we're willing to do the work and call the damn leads. Today's guest is someone I'm super excited to have on. I've watched him call the damn leads, build his business, and scale up to help others learn how to grow and buy back their time. He's my friend, the owner of EO Staff, Mr. Chris Kille. What's up?

Chris Kille (00:58:15):
What's up, dude? How you doing?

Drewbie Wilson (00:59:82):
I'm crushing the day, man. You know what it is. What's up with you?

Chris Kille (01:02:47):
I do. I got that text from you this morning. I'm also crushing the day.

Drewbie Wilson (01:06:89):
I know you are. I like to jump right in. You've been in sales a long time and done a lot of crazy stuff. I want to hear a crazy sales story.

Chris Kille (01:16:97):
Oh, right out of the bat, huh? Okay.

Drewbie Wilson (01:18:83):
Yeah, bring me something dirty and nasty. Let's get them interested so they'll hang out until we talk about the stuff that's really gonna help them later on.

Chris Kille (01:23:56):
We got to hook them in. So I've been in sales for almost 20 years now, and I used to go door-to-door for about a decade selling credit card processing. It's a super competitive and not always ethical industry. Your phone rings 10 times a day, people are always popping in your business if you got a brick and mortar. Sometimes people have bad days, myself included. I remember I was in Tampa, Florida, my third year doing this. I was knocking doors and it was a shitty day. Nothing was going my way. I was getting yelled at all day. So to turn the day around, I would try to have fun at other people's expense. I would act dumb or do stupid stuff just to make myself laugh.

I walked into this specialty wine shop. The guy behind the counter had a ponytail, was drinking a glass of wine at three o'clock, and had a cigarette in a retail location. He hit me with the "not interested" right away. I played dumb with him, and he got more irritated.

Finally, he picked up a bottle of wine and threw it at me. I dodged it, and it went right through the window. He told me to get out or he'd call the police. Instead of leaving through the door, I walked out through the window and ran to my car. That was one of the wildest experiences I've had.

Delegation in Business Management: Building Confidence in Sales

Drewbie Wilson (05:38:51):
I mean, A, I know your personality and I could see how a younger, rowdier Chris Kille would definitely stir the pot. That's kind of what sales is, right? Sometimes you gotta have the confidence to take a couple of no's, push through initial objections, and have a real conversation.

Chris Kille (06:02:06):
Sometimes you can flip them when you do that.

Drewbie Wilson (06:06:10):
Sometimes you can't. But if you walk in and immediately walk out when they say no, they have no reason to work with you. If you can make them understand why they might be saying no to a huge savings, then you've got a chance. It's like a script. Do you ever notice you start selling by accident?

↪ Discover foundational insights! Explore our latest podcast episode with Mike Bauer on building confidence and competence. Visit the blog now to listen to the podcast


Delegation in Business Management: Leveraging Indifference as a Sales Strategy

Chris Kille (06:39:72):
Yeah, sorry about that. And give me your credit card. I'll set this thing up for you.

Drewbie Wilson (06:57:64):
Or if it was like some employee, some dickhead manager who then had to call the owner and be like, "Jonathan, I threw a bottle through the window."

Chris Kille (07:10:19):
I never even thought of that. Dude, you're never gonna guess what happened today. Oh my God, this guy, he came in, he was a dick, I lost my temper. Anyway, I'm sorry.

↪ Explore strategic sales tactics with Randy Goldbaum! Visit our blog to listen to Episode 14 and elevate your sales game."

Delegation in Business Management: Navigating Emotions in Sales

Drewbie Wilson (07:18:70):
If you've ever done that, send us a message, share this on social media @callthedamnleads @notchriskille and let us know. Sales is about dealing with people's emotions. People buy for two reasons: to get out of pain or to get into pleasure. In the door-to-door situation, especially, it can be a race to the bottom. Do you have a sales superpower or secret weapon that you use?

Chris Kille (08:47:27):
For me, I use indifference a lot. When people get commission breath, it's obvious. I've always taken the mentality of wanting your business but not needing it. If you say no or cancel, I'm not going to be standing out in the street with a cup in my hand. Taking that route instead of the overconfident, cocky route typically works better because it disarms people.

Drewbie Wilson (09:43:69):
A lot of people have a good bullshit meter. We know when someone's trying to sell us something. In 2024, most of my sales come from people who have already looked me up online. They know who I am, what I offer, and my pricing before they hit submit. With few exceptions, it's hard to go door-to-door and manufacture that need.

Discover powerful insights on controlling your reactions in our latest podcast episode. ↪↪ Visit our blog and tune in now! 🎧


Effective Delegation in Business Management: Boosting Your Online Presence

Chris Kille (10:57:90):
Exactly. There's this instant gratification world where you can press a button and have anything sent to your home. You've built an online presence so people know you and your authority. I'm wearing a sweatshirt that says "delegate" because as a solopreneur or sales professional, you can only do so much. Tell me about your transition from doing it all yourself to delegating.

Chris Kille (12:11:08):
Delegation is hard because you think you're the only one who can do something 100%. You hit your ceiling and breaking point. Before I started hiring people, I cried at the office from being overwhelmed. Hiring assistants, especially from other countries, helped. Recognizing what you need to get off your plate creates space to breathe, move, live, and grow. You can't do that by yourself. What got you here won't get you there. Recognizing and transferring tasks is the secret sauce.

↪ Discover 5 effective ways to integrate social media into your sales process. Visit our blog now and tune into the podcast!


Effective Delegation in Business Management: Mastering Time and Task Allocation

Drewbie Wilson (13:57:94):
Understanding your time's worth and where you're spending it is key. What were some of the first tasks you delegated?

Chris Kille (14:48:87):
Start with a time study. Every hour for a week, write down what you did. You'll find you waste a lot of time. Create a table and decide which tasks you like or don't like. Delegate the ones you don't like. Put a dollar amount on them, from $5 tasks like checking email to $5,000 tasks like spending time with family. The first things I tackled were my calendar and email. My assistant organizes my inbox and handles most of the emails. I only check it twice a day. This saves so much time. I also let her handle my calendar. Everything goes through her. I also get a daily action items email with a snapshot of my bank balances, updates on projects, my schedule, and escalated items. I use screencast software to record my screen and answer her questions quickly. This system makes everything efficient.

Discover effective time management hacks for entrepreneurs! Visit our blog to listen to the podcast. ↪ Explore Now!


Delegation in Business Management: A System for Efficiency

Drewbie Wilson (22:32:33):
Some people listening might think that system won't work for them, but it can. It starts with one thing and one person at a time. Chris, how many people have you helped place assistants?

Chris Kille (23:38:51):
Not thousands, but we've helped a lot. I give everything away for free. I have a Facebook group, Buyback Resources, where I show people how to do it. We cover the seven core competencies every assistant should have.

Drewbie Wilson (24:18:57):
What's the name of the group?

Chris Kille (24:20:14):

Drewbie Wilson (24:24:08):
I'll make sure that's in the show notes. No one teaches this stuff in school or at companies. Hiring an assistant to take small tasks off your plate can change your life. It frees up time for more important things. Chris, how can people find you and get those resources?

Chris Kille (27:06:73):
You can find me on Facebook, Christopher Kille, or Instagram @notchriskille. Also, join the Facebook group, Buyback Resources. We give away a lot of valuable information.

Drewbie Wilson (27:55:47):
Thanks, Chris. If you got value from this episode, share it on social media and tag us @callthedamnleads @notchriskille. If you have a crazy sales story, go to and send us your information. Check out the store for some cool swag. Thanks for being here, Chris. We'll see you on the next one. Later.

Explore the transformative power of personal connections in lead generation! Visit our blog now to listen to the podcast and uncover 'The Importance of Calling Your Leads'. Click here to start discovering more!


Connect with Chris:

 I’m Chris Kille, an entrepreneur and investor based in Boston, Massachusetts. I’m the Founder of Payment Pilot, where we specialize in processing payments for home service businesses, and EO Staff (formerly Elevate Outsourcing), where we provide senior-level Executive Assistants to US businesses.

Over the past 20 years, I’ve dipped my toes into various industries like tech, finance, collections, transportation, and animal care.

Entrepreneurship is practically in my genes. Both my folks run their own businesses, and I’ve learned heaps from their wins and losses. After trying my hand at different jobs, I took the plunge into my own ventures, and it’s been one of the best decisions I’ve made. No looking back!

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Your Host, Drewbie Wilson:

 With over $15 million in online sales, Drewbie's vast experience spans multiple industries. His journey from a 300-pound weight loss to becoming a sales powerhouse has shaped his perspective on life and success.

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