OAS Tom | Automating Your Business


In order to grow and scale your business, you have to have systems and processes in place for your business to keep running even when you step away from it. Tom Sylvester, the Cofounder of a training and coaching company called Lifestyle Builders, joins Nathan Hirsch to talk about the two ways you can take things off your plate – automation and hiring – as well as how to determine which things are important and which ones are not when you’re “de-cluttering your house.” Tom goes through some communication tools you can use to manage your teams and identifies the three different levels of people you can hire – the followers, the doers, and the experts – and which ones you should hire at different points in your business. Join us to find out more about what you can do to scale your business today.

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Tom Sylvester on Automation, Hiring, And Decluttering Your Business

My guest on this episode is Tom Sylvester. Tom, how are you doing? 

I’m doing great. How about you? 

I’m doing great. I’m excited to talk to you. I know you’re a systems and process guy, which is what I’m all about. For those of you that don’t know, Tom is the Cofounder of Lifestyle Builder, a coaching and training company that helps entrepreneurs build their businesses to create more impact with their customers and get freedom in their lives. Over the past years, he has helped with thousands of business leaders and helped their teams create more success through Fortune 500 companies all the way to startups. Tom, we’re going to talk all about systems, all about processes, but first, let’s take a gigantic step back. What were you like growing up? Did you know you wanted to be an entrepreneur? Were you a rebel? Were you a straightA student? How did you get into being an entrepreneur? 

I always knew I was different. I always did well in school but I didn’t enjoy school. I didn’t enjoy the way of learning. In school, they would call it cheating, but I was always looking for like the most creative way or the easiest way to get something done. I always had like side hustles, but the turning point came when I got to college and I took my first computer programming class. The professor gave us an assignment and everyone walked in with sheets of paperI had one sheet of paper with a couple of lines on there. I was a self-taught programmer and I was like, I’m going to get kicked out of here. They’re going to see I’m a fraud.” 

When the professor saw my paper, he pulled me up in the front of the room, had me share it and I’mlike, “This is terrible. He’s like, Tom, you are lazy. I’m like, “He’s got me.” He’s like, “That’s good because the lazy people don’t want to go the traditional path. They’re looking at what’s the least amount I could do to get the resultThat’s what this is all about. I know you’re going to do well.” When I look at it from an entrepreneur perspective, what I’m always looking for is whatever problems I see are coming up, I’m like, “How can we do that better and how can we do that more efficiently? 

[bctt tweet=”With systems and processes, the ultimate goal is to strip away everything that’s not value added.” username=””]

Tom, what was your first real entrepreneurial endeavor? 

I always had side hustles. In college, for example, I was buying used books at thrift stores and then selling them on Amazon. This was back before we had smartphones. I always had these things, but when I got out of college, I looked ahead and I said, I don’t want to be sitting in a cubicle for the next 45 years. I tried a bunch of businesses, but my first real one was real estate investing. I got into that, took a little bit to figure out, then from there we ended up building several other businesses beyond that.  

You’re starting these different businesses. You had to have systems and processes in order to do that to be able to step away and start business number two, business number three. How did you go about creating those initial systems to be able to take a step backI feel like that’s where a lot of entrepreneurs struggle. 

An interesting fact was started three of our businesses while I still had a fulltime job. What was unique and good about that was it forced me to ask the question, what does this business need to look like to be able to run while I’m working? A lot of people, when they dive fulltime in entrepreneurship, they automatically jump into every role and do all the work. That’s tough to then create systems because they put themselves in every role. What I had to do with each business was essentially the question I always ask iswhat needs to be true for this to work? I knew that I was going to be working a certainamount of time. I had to design the business and understand what roles need to be in place, what things needed to get done, then I could intentionally design the business and put those pieces in place so that it could run mostly without me. 

You’re almost saying that you architect the business upfront to run without you instead of being involved and then trying to bring yourself out. 

Stephen Covey’sBegin with the End in Mind, it’s one of the best quotes and it’s something that we always do. For example, when we work with a lot of entrepreneurs, we’ll first help them figure out what they want their life to look like. Part of that is saying, “Based on your life looking this way, what business model will help you get there? What does that business need to look like? What we can then do is to your point, the architect of business and then we say, “We’re at starting point A. This is where we want to be, so then we build a roadmap there. What happens with a lot of entrepreneurs is you might initially play all the roles, but by thinking about what it needs to look like, you can consistently then say,“What do I have to get off of my plate in order to get closer and closer to that?” By being intentional about that, you’re not diving in then trying to figure it out. You’ve got a plan laid out and you’re then adjusting along the way. 

OAS Tom | Automating Your Business
Automating Your Business: Be intentional about what you want your business to look like. Don’t just dive in, but have a plan laid out and then adjust along the way.


Taking stuff off your plate there, there are two ways to do that. You’ve got the automation and the hiring. Talk to us a little bit about your mindset going into each. 

Before automating the hiring, the first thing we always look at is, what can you eliminate? Every process, every system can follow this simple format, which is there’s a trigger, something that starts it and kicks off this process. There’s then an end, which says, “This process is complete and we can do something else.” There are three to five major steps that happen in between. If you’re thinking about it, you want to say, “For any process I have, what is the trigger? What are the three to five major steps and what’s the end result?” Once you get that documented, you can then break those major steps into sub-steps, then before you automate or delegate anything, what you want to go through is each of those steps and say, “If I remove this step, will that prevent me from getting the end result? If the answer’s no, you want to remove that. Have you heard of Marie Kondo with her Spark Joy and all of that? 

No, I haven’t. Can you tell the readers more about it? 

She‘s got a Netflix documentary and a couple of books. She’s all about decluttering your house. What she looks at is, is this contributing to you? If it’s not, you can remove it and it’s going to free up and make your life happierIt’s the same thing with systems and businesses. If you have too much stuff in your process, the things that aren’t adding value are going to clutter all the stuff that does add value.Your ultimate goal is strip away everything that’s not valueadded, which is a waste and then with what’s left, now you can say, “Which one of these tasks is good for a computer to do? These are things that are repetitive. They don’t require a lot of thought and you want the same thing happening every time.When you automate those tasks, what’s left over is stuff that usually computers aren’t good at and humans enjoy because it forces us to think and be creative, not just sit and hit the same button over and over again.

That scares a lot of people because whenever you have so much stuff going on your business, you just start eliminating things. You start to think, “How does that affect the big picture? How do you figure out what is important and what’s not? 

big part of this is you do it incrementally. Whenever someone’s trying to implement a system or put a process in place, they’ll often get overwhelmed and they feel like they’ve got to do everything at once.They’re so busy now that they don’t have time to do it. One of the first things we always recommend to people is that every single week, you should be having a weekly meeting. What you do in this weekly meeting is the first part is you reflect, What wins did I have this last week? Let’s acknowledge what’s going well. Let’s also identify what challenges exist because those challenges we want to be solved going forward. By doing that, you can then take the top challenge, the biggest headache that you had, and in the upcoming week, you just put a process in place or you adjust a process to either reduce or get rid of that issue. By doing this, a couple of things happen. One, you’re able to consistently make improvements that get rid of the biggest headache you had the previous week. Second, it’s not you have to do it all at once and not being overwhelmed or scared of having to put processes in place. 

[bctt tweet=”A lot of people first focus on skills when hiring, but the first thing you want to focus on is are you a good fit and can you work together?” username=””]

You’re talking about automation. That’s another area that scares people, people that either doesn’t know how to code, work with developers or had issues. Are you talking about using stuff like JP or you’re talking about building your own software or is that a combination of both? How does someone who’s not familiar with that space gets started automating parts of their business? 

My background’s in Computer Science, so I definitely am a programmer. I understand all of that. What’s beautiful about this day and age is that you don’t have to know how to code to make just about anything. Even when we’re working with startup companies that are creating apps and stuff like that, the first version of their apps often has no custom coding. They’re using different services that are out there and we’re piecing them together. You mentioned something like ZapierWhen I talked about the process earlier with a trigger and a set of steps and end result, Zapier set up the same way. 

When you map out what your process looks like, you can use something like Zapier to say, “When this thing happens, do this thing, then do this thing, then we’re done. For most people, you should never have to custom code or do anything like that. As you grow your business and if you have very specific things, it might get to a point where you want to hire somebody for that, but there are so many out of the box solutions and so many great pieces of software out there that it doesn’t take a lot. If it does, usually what you’re trying to do is to have somebody integrate two pieces of software rather than creating something from scratch. 

Let’s talk about hiring. What about the process before hiring? What do you need in place before you hire someone for your business? 

There are a couple of things. The first thing is you want an understanding of what the end result is that you’re trying to hire for. I’ll give an example. People come to me and say, “Tom, I want a coach.” I’m like,“No, you don’t want a coach. What is it you think a coach is going to get you?” They tell the real problem and that’s what you’re trying to solve. You don’t want to go out and say, “I want to program” or I want a VA.” Whatever that role is, you want to go out and say, “This is the end result that I’m trying to get.” You work backward. You’re going to notice this theme that we always start with the end and we work backwards. When you understand the end result you want to get, you’re then able to work backwards and say, What is required for this? What are some of the characteristics that a person needs to have?” and then working all the way back to say, “For our company, what characteristics does this person have to have to be able to fit into our culture and to be able to work together?”  

A lot of people first focus on skills when hiringThe first thing you want to be able to focus on is, are we a good fit? Can we work together? You can have the best person in the world and if you can’t work withthem or if they can’t work with your team, everything else is going to struggle. Whenever I’m interviewing someone, there are always two questions that I ask and the majority of the time, this will help me figure out if I’m going to hire them or not. The first question is, tell me your story. This does a couple of things. I can see where they start, what they think is important, how well they communicate, are they longwinded, are they giving me little tidbits or are they well with that? You’re going to get a lot in between the lines from that question. The second question I always ask is, why are we here now?Amazingly enough, people are usually very honest with that. From those two questions, I’ll know if this issomebody that’s going to be a good fit for the role and for our companyIs this somebody that maybe their intentions aren’t aligned or they’re not great communicators? We’re going to struggle to be able to incorporate them in, especially if this is somebody that’s in like a remote position.

OAS Tom | Automating Your Business
Automating Your Business: Different people, based on personality types and skill sets, are going to need different types and levels of support.


I love that second question, “Why are you here?” because I can see people saying, “Because I need money, I need to pay a bill,” or something outside of what you want to hear there. Talk a little bit about after the hire. You’ve identified what kind of person you want to look for, you’ve interviewed, you’ve found a good fit. I know you mentioned having those weekly meetings. What else do you do to set expectations and to make sure that people are meeting those expectations ongoing? 

I love the fact that you said that word, expectations. This is the most important thing that so few people do. When you’re setting expectations, it looks like this. Nathan, here are my expectations for the role. Here‘s the desired outcome. Here’s how I need you to show up and function or whatever that is. Here’s the piece that most people miss. You then went on to turn it around and say, “What are yourexpectations of me? Now that I laid out what the desired results are, what do you need from me in order to be successful in this role?” This does a couple of things. One, right away, you now know how you need to support that person because what you’re going to find is that different people based on the personality types, based on their skillsets are going to need different types and different levels of support, so instantly hear from them what they need in order to succeed. 

The second thing is you see if your expectations are aligned or not because far too often what happens is that we will say, “We’re in agreement, right?” You say, “Yeah.” I say, “Yeah,” then time goes by and you’re not hitting my expectations, but you don’t realize that you think you are. I don’t know how to bring it up because I didn’t set them right at the beginning. It’s very challenging. When you set expectations that way, right away if there’s a disconnect, you address it and it’s not awkward because nothing has happened yet. What you do is you set that consistency cadence of following up. Here’s the expectation, here’s what we’re looking for to happen by when and here’s how we’re going to follow up. 

If expectations are off either way, here’s how we’re going to address them. What you’re doing is you’re giving each other permission to talk about, “We’re missing expectations and let’s get back on track.” When that happens, it’s like, “Nathan, when we talked last week, you said that this thing was going to happen. What I’m seeing is that it’s not happening. What you want to do is you want to raise it up, but you don’t want to assume why that person is doing it. What you want to ask is there like what’s going on? What support do you need in order to hit that expectation that we agreed on? By doing that, a couple of things happen. It’s very easy for you to bring it up. When you do bring it up, you’re bringing it up from the point of, “We both want to win. How can I help you win?” rather than, Nathan, you didn’tdo your job. You’re fired.” 

I always say that there are three different levels of people you can hire. You can hire the followers, think more of that virtual assistant for your processes. You can hire the doers, let’s say the specialists that graphic designers, the writers. You can hire the experts, the highlevel freelancers, the agencies,the people that bring their own strategy to the table. Are you mostly teaching people how to hire followers? Is it all three levels and how does your process change depending on what type of person you’re trying to hire? 

It’s all three levels and what I find is that at different points in business, you’re going to hire different levels. It always comes back to your strategy and what you’re trying to achieve. In some cases, especially early on, you might be hiring someone for a specific project. The scope of that is then that project and the fitting into your company. Some of that may not be as critical, but if you’re now looking to grow your team and you’re looking to hire somebody in on multiple projects or more permanently, now it’s a lot more critical to make sure that they’re going to be a good fit for your team. It comes back to once again, what are you trying to achieve? What makes the most sense? A lot of people will often try to go very cheap on things. What they don’t realize is that sure you can.

[bctt tweet=”When hiring people, talk about what the desired outcome is, not what the tasks are that somebody is going to do.” username=””] 

On paper, spending less money sounds good but if you’re going to have delays in communication or the results, if that’s going to pull you away from your highervalue activities, even though the $3 or $5 or whatever it sounds good, it’s going to cost you a lot more because your time is more valuable in most cases than any money you’re going to pay. What you want to figure out is what is the right level for you to be able to pay that’s going to allow you to hire the right level of talent? What I find is a lot of people go too cheap and end up spending more of their time and get frustrated with delegating and hiring somebody. 

You mentioned that a lot of times people feel like when they’re hiring people, it’s adding more work to their plate instead of what it should be doing and freeing up their time. Besides making sure you’re paying the right amount, what else can you do to ensure that does free up your time longterm? 

One of the biggest things is you want to talk about what the outcome is and not what the tasks are that somebody is going to do because in most cases you’re hiring somebody that should be bringing some skills to the table. By talking about here’s the desired result, you can then work with that person to say,“Here’s the framework. Here’s how we’re going to think and how we’re going to work together. What a lot of people do that end up getting burnt out with hiring team members or fear it is that they tell their team member what to do. For example, “Edit this blog and do this thing and do this thing. The team member goes and does that. They run into an issue and now they haven’t been taught how to think or what decisions they can make versus what they got to come back with.

They’re coming back and asking me a question, pulling me away from something else. It gets frustrating because it’s like, “This is taking me way more time and I’m better off doing it myself. What you want to be doing is set the outcome, but then talk through the decision making framework and what decisions that person can make on their own and which ones they should come back and check with you on. If this makes people nervous because they feel like they’re getting rid of control, all you’re going to do is put checkpoints in along the way before something moves from one step to another. 

For example, let’s say somebody is editing a blog and they’re nervous that somebody else is going to edit it wrong or do whatever else. You have that person do the task and then there’s a checkpoint before it moves onto the next step where you can go in, confirm it’s up to your standards and then you allow it to move on. Whatever it is that’s holding people back or causing them to not want to give up control, you’ve got to look at what is the thing that I need to see in order to allow to happen and then set that into the process. 

It’s figuring out what decisions people can make and which ones they should escalate to you is a huge part of saving your time. What else that we didn’t talk about so far or mistakes that you commonly see from your clients when it comes to hiring, scaling and automating your business? 

OAS Tom | Automating Your Business
Automating Your Business: One of the biggest challenges entrepreneurs have is managing their business today while also planning for the future.


One of the biggest things, and it’s a challenge, is managing your business now while also planning for the future because a lot of entrepreneurs, we’re flying by the seat of our pants. We don’t have a lot of planning in place. I came from the corporate consulting world. I was spending a lot of time doing strategy with leaders. We were planning out what do we got to do now? What does six months, nine months, a year, three years, five years look like? For most entrepreneurs, they would benefit is making sure that you have a longerterm vision. You’ve got a shortterm focus of for example 90 days and you’re constantly checking in and readjusting. 

When you do that, you’re making sure that you’re handling what you need to do now. Because you know six months out you might need a certain position or you might have a certain project coming up, you can now start doing some of the work so that by the time that comes, it’s not a surprise while also managing your daytoday. It is a little bit of a balancing act, especially as you’re growing. The more time you can spend planning and strategize, the more prepared you’re going to be, not only to understand what’s coming up but when things change to be able to adjust along the wayMost people aren’t being proactive when it comes to planning the stuff and then having the right system in place to be able to quickly shift when other things come up. 

can see a lot of entrepreneurs struggling with that big picture. You have multiple businesses now. You use a lot of freelancers. Can you walk people through what your normal week looks like in terms of managing, meeting, setting expectations, give people a sense for how it can be done at a high level? 

We implement this cadence that works well. It comes down to there’s a daily meeting that’s fifteenminutes or less. Each member of our team is spending a little bit of time getting clear on what did I accomplish yesterday, what am I planning to accomplish today? What’s the intention? What’s in my way, or what support do I need? With each person doing that, we then have a quick call, depending on the business. It could either be a quick call, it’s fifteen minutes or less where each person’s sharing that or it could be done something like Slack where everyone’s able to share that because time zones might be different. What this allows everyone to do is you’re spending a couple of minutes to get clear on what you’re going to do that day, as well as you understand what everyone else is working on. 

If two people are working on the same thing, you instantly know that. If somebody needs something, you instantly know that and you can then coordinate on how to do it. That avoids a lot of emails, a lot of time delays because someone’s waiting on a decision from someone else or someone has a problem, they don’t know how to solve it. That’s the daily meeting. The weekly meeting is the key beyond that, because every week we’re going to have the team check-in. The intention was to get this stuff done this week. What went well? What didn’t go well? Let’s look at our scorecard. Let’s look at the key areas of the business, a couple of key numbers that are going to tell us how things are going. Based on that, set the intention for the next week and understand what each person needs to do so that we’re all coordinated. 

The combination of those two meetings allow us to know what we’re doing week by week and then daily to check in on the execution of that. Beyond that, we’ll then have more strategic meetings, a monthly meeting to check in on budgets and all of that, a quarterly meeting to check in on goals. It’s that cadence of strategic planning so you know where you’re going, but then that daily and weekly execution, so you make sure everyone is doing what they need to move towards that. Your job as then the leader and the founder becomes supporting the team and saying, I want to get out of your way. What support do you need to do to be able to get everything done? 

[bctt tweet=”The more time you can spend planning and strategizing, the more prepared you’re going to be for what’s coming up and adjust along the way.” username=””]

What tools are you using? Can you give people a list of some common stuff? I know we mentioned Zapier and Slack. What other ones do you use? 

Google Suite is one of our huge tools, so that’s able to cloud storage. We can collaborate on documents.Zoom is a good tool. We use that for a lot of our coaching calls and team calls. Slack is another great one. Slack will often replace email for internal team communication. I think those are the major ones.Zapier is good one for automation. It’s going to help connect different pieces and different tools together. Those are probably the core ones. What I find is about every business we work with ends up putting those tools in place. Another tool is everyone needs some project management tool. Depending on how your business is running, Trello is good for more like a strummer Kanban system where you’re prioritizing work, taking one thing and doing it. Asana is good for more of traditional project management where you’re planning out projects and assigning them to people. Those are probably the core tools that I see most businesses using to help manage the team and improve communication. 

What else did I miss? What other common things do you help businesses with or do you see mistakes that business owners are making? 

One of the biggest mistakes business owners make is that they focus too much on the business and not enough on themselves. This could come in not taking care of themselves. Your health, mental and physical is a big part of being able to show up for not only your business, but your family and other people that are important in your life. It not only supports your customers but supports you because a lot of times, what we see happen with entrepreneurs is that they essentially prioritize the business ahead of their life. That can lead to some really bad consequences. We’re talking divorce, we’re talking people regretting missing out on key moments of their life. One of the biggest things that we do with entrepreneurs, one of the first things we do is have them track their time for a week and see just where all their time’s going. 

We have them align that back to what their personal goals and what their business goals are. What we’re looking for is that is there congruency here? Are you able to live the lifestyle that you want and are you able to achieve your business goals? If there’s a disconnect there, now we can start to say,“What things should be on your plate you’ll be doing and what shouldn’t it be on your plate? All those things that shouldn’t be on your plate, then go into, what can we cut? What can we automate and what can we delegate? That then helps us work towards figuring out what tools do we need, what people do we need? Ultimately allowing that entrepreneur to not only have success in the business, but allow that success to drive that lifestyle that they’re looking for rather than all the negative things that could come up if they’re neglecting their life, just focused on the business. 

OAS Tom | Automating Your Business
Automating Your Business: Your health is a big part of being able to show up for your business, your family, and all the other people that are important in your life.


Where can people find out more about you and what are you most excited about for the rest of the year? 

Our main website is www.TomAndAriana.com. You can hear everything we have going onpodcast, our book, programs, everything else. What we’re excited about is our first book, which is being released in2019. It’s called Lifestyle Builders: Build Your Business, Quit Your Job, And Live Your Ideal Lifestyle.Essentially, this is the process that we take entrepreneurs through. It’s figuring out what you want out of your life, getting your personal finances in order, validating your business idea, then putting the right systems and processes in place to help us scale. We show people how to then transition from being afreelancer to an entrepreneur. Then ultimately use all of that to live your ideal lifestyle now rather than having to wait 45 years until retirement and that hope you can do it. 

Thanks so much for joining us. Check out Tom’s book.  

Thank you.

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About Tom Sylvester

OAS Tom | Automating Your BusinessTom Sylvester is a co-founder of Lifestyle Builder, a coaching and training company that helps entrepreneurs build their businesses to create more impact with their customers and more freedom in their lives. Over the past 15 years, Tom has helped with thousands of business leaders and their teams create more success, from Fortune 500 companies to startups.