Skip to Content
Back to Blog

How to Find, Hire, and Retain Salespeople & Estimators




I’m overwhelmed as a business owner…because I have SO MANY estimates that need my attention, how can I hire a good salesperson or estimator?

Have you ever found those words echoing around inside your head?

You’re not alone! In this episode of the Green Industry Perspectives Podcast, Sean Adams goes rogue and shares what he’s experienced regarding employee dedication and turnover and how he approaches hiring an estimator/salesperson. He illuminates his 5 step process for cultivating company culture and ideal employees.



You can tune in above on Apple PodcastsSpotifyStitcherGoogle Play, or anywhere you get your podcasts.

Become a pro member of the podcast to receive notifications for each new episode and bonus content each week.

On this episode, you’ll learn:

  • Sean’s 5 part process for hiring salespeople and estimators.
  • Step 1 – Identify 
  • Step 2- Find
  • Step 3- Hire
  • Step 4- Train
  • Step 5- Retain

What to listen for:

[4:00] How to identify what you need in a salesperson. 
[12:31] Where to find your future salespeople. 
[20:18] Hiring the right candidate and great interview questions. 
[22:47] Develop a strategic plan towards training new employees. 
[42:23] Strategies to ensure you retain good employees

Links to love

Full Transcript:

Sean Adams:

You are listening to The Green Industry Perspectives podcast, presented by SingleOps, a podcast created for green industry professionals looking for best practices, tactics and tips on running their tree care or landscape business. 


Hello, everybody and welcome to another episode of The Green Industry Perspectives podcast. This is Sean Adams, your host and we’re going to do things a little bit differently here today. I’m actually going to do a solo cast and riff on a topic that comes up very often in my conversations with green industry business owners. It was certainly a pain point for myself in my business and hopefully, I can expand upon a couple of points here to help you guys. So, it’ll just be me here. Unfortunately, you have to listen to my voice if you want to stick around on this episode. Totally understand if you’re not interested in that and you want to skip over this episode and move onto an interviewee. That’s perfectly fine as well. But I’m going through a process that I used in my business and some things that I’ve picked along the way in working one-on-one with a lot of green industry businesses over the years.


So, the topic today is going to be around salespeople, estimators, sort of that managerial level of our business, the second-hand man if you will. And so, with this particular year, we’re talking in 2020 here, the past couple of years have been every bit as good, the overwhelming theme that I have been seeing in the green industry is that people are busier than ever. Now maybe commercial work is down but the residential work is back up. But the industry as a whole, people are thriving and there aren’t enough hours in the day to get done all the work they want to do. So, one of the things that people ask me constantly is Sean, I’m overwhelmed as a business owner. I’m trying to manage the field staff, manage my different crews, I’ve got some people in the office. But one of the biggest pain points for me and where I spend the vast majority of my time is around estimating and selling new work. Maybe that’s new commercial recurring contracts on the landscape side. Maybe it’s design, build, installations on the landscape and hardscape side. Maybe it’s tree work, one-off plant healthcare services. You name it. There’s going to be endless amounts of different sales and estimating and consultations that we need to do and by default, those typically fall on the business owner.


And so, with so many other things vying for your attention all day long, this is something that gets neglected or is one of those things that’s very overwhelming for the business owner. And so, the first thing they think of is hey, I’ve got to get somebody in here to help me with estimating, another salesperson, an estimator, however you call it in your business. It’s all about the person who’s going to provide quotes and meet with customers and close new business. And so, I’m going to take you through a framework that I used in my business and as I mentioned, has been basically different pieces and resources I’ve pulled after working with other companies as well. So, this process is going to have kind of five components here. While we’re in a long form content here as a podcast, I certainly can’t talk to every one of these components on what it takes to identify an employee all the way through to hiring them, onboarding them and all that sort of stuff. But I should be able to give you a couple of bullets, maybe even just thinking creatively about some different ideas on how this can help you in your business. 


So, the process goes in these five components. We first have the identify step and we’re going to go through these each in a bit of detail. Then we have the find step as in where I’m going to find this employee. We have the hiring step which is going to go into the questions about interviewing and compensation and that side. We have the training step. And then lastly, we have the retention or retainment step. So, once we get them trained and they’re ramped up in our company, we also need to retain them as an employee who’s going to stick around hopefully or if they do move on, they’re going to move on amicably with us or from us. And so, we’re going to talk about some ideas in each one of these steps. So, first off with the identification step where I identify in the first kind of pivotal piece here. This is a bit of a mindset around how you look at hiring. Now I’m going to throw my own opinion in here and being that the labor shortage is arguably the biggest issue facing our industry, there are a couple of things in here that we’re going to have to unpack. So, the number one question is yes, Sean, I want to go and find someone to be my second-hand man, to help me run estimates or I want to hire four of them over the next couple of years. How do I develop a process around that? I can’t find any good help. None of these kids want to work. Millennials are the worst and the problems and the blame game just keeps spiraling out of control. 


So, my sort of argument back against this is that traditionally, not to go off on a major tangent, but over the past 30 years or so as a society, we have been forcing or the narrative has been that blue collar jobs are not ideal, right? So, in the 80s, the 90s, parents did not want their children to work in the trades, did not want them to be landscapers, tree care companies, construction workers, right? It was kind of looked down upon. They wanted them to go to a four-year college, go and work for a corporation, get a nice steady job with a 401k, so on and so forth. And so, for 30 years, the industry or the society has been conditioned that this is not an ideal industry and as an industry, we’ve done a terrible job of marketing why it makes sense to come work here. So, we’re looking at the end result of 30 years of kind of detriment against our industry. So, it’s no wonder why we don’t have enough of an inventory or large enough labor pool to fill the jobs that are out there. There just simply aren’t enough butts to go in the equivalent seats, right? Every landscape or every tree care company is hiring. There certainly are not enough people to find that. 


So, inherently you have to get through your head that you’re working uphill. There’s a shortage in the industry and when there’s a shortage that means you have to get creative. And so, when I look at identifying employees, I look at them in two buckets. So, we have what I call draft picks and we have trades. Now I’m using a sports analogy here because I think it resonates well. So, a trade is going to be someone working for another company, right? So, that means that they’re already working for another landscaper down the street or they have experience in this industry. And the other side of this is going to be the draft picks. This is the guy coming out of high school, coming out of college, relatively little experience professionally or in the industry specifically but we want to try to take them on young and kind of green and train them. So, those are the two kind of avenues we can go when we’re hiring. Most people gravitate towards trades because they think in their head that there’s going to be sort of the path of least resistance, right? They already have the skill sets I require. I just find them and bring them and to work for me and sunshine and rainbows. I’ll never have a problem again, right? There’s a bunch of issues in that and one of them is again back to the shortage. There simply aren’t enough of those people out there to sustainably bring on all the people that you want to in the future even if you’re looking for one person. At some point, you’re going to be wanting to grow and outsource the work that you’re doing. And so, you need to make sure there’s an inventory or a process in which you can identify these people. 


So, my opinion is to focus more heavily on draft picks and what I mean by that is basically taking people with relatively no professional especially green industry experience, training them on our systems, training them ourselves in our own little ecosystem. One of the main reasons for that is because trades in theory sound great because they’ve already got that experience and we’re just going to plug them into our already existing machine and it’s just going to thrive. The faulty logic in that is they’re also going to bring in all their founded experience and their expectations and their habits some of which may be very poor habits. And so, what that means is you have your way of running your business and they’re going to have their way and they’re leaving the company they’re at now for some reason, right? Maybe they don’t like the management staff, maybe they got stepped on or maybe they just are not a great employee and they’re just looking to move on to somebody else that they feel like they can step on. And so, when you hire someone like that, what’s ultimately going to happen is you inherit all of their bad habits and it gets extremely painful to try to navigate through this. 


I went through this exact same experience in my business. I tried to hire a salesperson, estimator, kind of project management, sort of hybrid role and I wanted ten years of experience and multiple years selling in the landscape industry. They had to be local to my industry or my area and they had to meet my budgeted price range as well. And that was like a needle and a haystack, right? So, I put up the job postings and I went through the whole process on Craigslist and Zip Recruiter and Indeed and all these things and I got 20-30 interviews and I found one guy who was well-spoken and had industry experience and I basically fell into the trap of what I call abdication versus delegation. If you’re familiar with Michael Gerber and the E-Myth, he talks about this extensively and it’s this idea of abdication is basically what I call like task dumping. So, it’s just relinquishing all responsibility for the position and just dumping it on somebody else’s plate. So, not really giving them the preference or the reference points or parameters and just saying hey, you’re doing this role now. It’s your responsibility. Good luck to you. 


Versus delegation which is much more of a leadership and a sort of nurturing and teaching and training on your systems. Most of us see it as easier to find that quality employee, bring them in and just abdicate, just dump this stuff on their plate. Okay, John. Run out there. Start giving estimates. With no real frame of reference and it’s no wonder why it blows up in our face, right? That’s exactly what happened to me and I found out that this guy had an unbelievable amount of poor habits that I could have sussed out during the interview process and basically saved myself an endless amount of time because I thought I was saving money and saving effort by hiring someone with experience where I actually kind of massively shot myself in the foot and wasted endless amount of time doing this. And so, you have to unteach all these bad habits and firing them is super uncomfortable and it’s just a whole disaster. 


So, the flip side of this is looking at the draft pick side and it basically comes down to this: hiring for that character and training for skills, right? It’s an old adage—I’m sure you guys have seen it—and it’s about developing a system versus over leveraging yourself on one individual employee, right? Because that employee could leave, they could get sick, they could not work anymore, they could just be great interviewers and terrible employees, right? If you put all your eggs in their basket, you’re incredibly over leveraged. Where if you work on building a system in which you can take a draft pick, a young person, a person with limited experience and bring them through a tried and true process, you actually are building like your own little university, your own system of training. That is what scale, that’s what business systems are all about because now if that employee were to leave, yes, it’s going to be painful, yes, it’s going to suck but you have the ability to bring someone else in behind them and run and leverage process over people. And so, it’s not about devaluing people but it’s about having sort of this risk mitigation on your side so you have a process behind that. We’ll talk a little bit more about that. 


And so, when you’re trying to find in that first step, it’s all about what direction are you going to go? Are you going to focus on those trades where you’re going to try to find someone with experience and much more of a needle in a haystack type of game? Or are you going to focus on the draft pick which is going to be someone that you can find the correct character in and then you can train all of basically the more hard skills, right? So, soft skills are going to be people that are charismatic, that are pretty outgoing, that listen, that kind of have ambition. Those are the people you want to search for because those are the kind of rare skill sets, the soft skills. And then all the industry experience and the certified arborist and how to properly estimate a landscape job, those things are teachable. They’re very teachable. It’s tough to teach someone how to not be their current personality. It’s a difficult thing to try to undo, right? So, if you look for that character, the rest you can work with. 


So, let’s talk about some places in which you can look for this character. There are several of these. I’m just going to rattle off a couple of ideas. I would always look at the restaurant space, right? I’m talking to you now in the summer of 2020, well amidst the coronavirus which means that all retail, all restaurants, they’re all really, really hurting or maybe just went out of business. So, someone in the food industry in particular, they breed a certain type of personality and a skill set. They’re used to kind of high exposure to volumes of people and they have to deal with specific orders and it’s high pressure and there’s a lot that goes into it. And so, the people that are your waiters, your bartenders, even bus boys and those sort of things or people that they’re used to working this kind of crazy schedule, working for tips and working with the general public, they’re typically very flexible and good with people. They can kind of navigate around that. So, those are great places to look in general. Specifically, during everything that’s going on with COVID, there’s going to be thousands and hundreds of thousands of waitresses and waiters out there that are out of work and they’re going to need something to do and they’re used to this sort of environment where they’re dealing with people and they’re moving on and they’re selling their services and trying to get a good tip. It’s the same general idea as what they’re going to do as a salesperson or as an estimator. And so, those are great places to start. 


Another good place would be I always look for like gyms or people that are overly indexed on their health and wellness or working out. One of the main reasons for that is going to be just because they like to be outdoors and they typically have good discipline. So, someone who keeps themselves in shape, inherently at least prescribes to their own sort of regimen, own good habits. Those are people that are going to be ones that normally have pretty good character because they’re showing that physically they have the mental toughness to stick around and go to the gym or do home workouts or whatever that might be and those skills are really helpful in sales environments or any kind of environment even if you’re talking about field staff. And so, if you’re on your social platforms or you talk to friends and family and you’ve got people out there that you know, go in those sort of networks to find people that are maybe younger. You got somebody who’s in there and they’re 18, 19, 20 years old and they really keep themselves in shape. They’re not sure what to do. They’re in between jobs. But they really take their health seriously. I mean what’s better than being out there in the field, meeting with people and they’re going to be outside. They get plenty of steps in. So, it’s a healthy job and it’s somebody that is going to have the character that we’re looking for. 


Another place for characters is going to be volunteers, right? So, maybe a little harder to find right now with everything going on but I always like to focus on there’s always eco-conscious groups, there’s maybe like local parks near you or sort of wildlife conservations or places where people gather to try to take care and preserve what’s going on out there for parks and outdoor spaces. People that are part of those groups, specifically younger people, are very eco-conscious, right? So, they care about the environment, they like being outside. Well, those are like two or three of the first couple of things they’re going to be dealing with if they come and work for a company like yours, right? they’re going to be outside. They’re going to be working with trees. They’re going to be working with landscape material and irrigation and drainage, all these components that go into a healthy thriving ecosystem and they can really feel like they would be a part of helping Mrs. Jones better her property which helps better the world in some sense. So, people that volunteer, you can go to these organizations and do meet ups or just put your foot in that arena any way you may want, those are going to be like kind of raising their hand that they care about the environment and that’s a great type of person. They may have no real landscape or tree care experience but they’re sure showing that they care about the outdoors and maybe they just never knew there was really a career in arboriculture or horticulture or irrigation or whatever it might be, right? So, you can frame up conversation because you already know they’re interested in at least one of these volunteer efforts. 


So, the last two are kind of intertwined here on the fine side and this is going to be students and kind of interns. So, when you look at a student, right? Somebody that’s in a community college or especially again going back to COVID right now, you’re going to have an unbelievable amount of people that are having a hard time swallowing paying $40, $50, $60,000 per year to jump on Zoom and watch their professor from afar, right? Or a lot of parents who are not comfortable investing that right now. And I’m willing to bet that there’s going to be a huge drop-off of people going to those four-year universities in this upcoming year. That presents an unbelievable opportunity for an untapped labor pool, right? You have people that maybe go to a community college, go to a local university because it doesn’t make sense for them to spend money on that experience because they’re not going to be getting that experience. A great way to maybe put Facebook ads on that kind of demographic or Indeed ads or reach out to people on social media who are students and want to go to school a couple hours a day and they want to have a job and make some money while they can, right? We’re one of the few industries that is completely thriving and we’re able to be sustainable during this crisis, right? And so, we don’t have the fear of any kind of downturn right now at least. So, it’s a great career path for someone like that or a part-time job. 


Same thing with internships. A lot of universities and programs want their students to have some sort of real world professional experience during their studentship. And so, if you can step in and maybe identify local college, local trade association, anything like that where you can have a conversation with promising young students that are clearly there for a reason and want real world experience, you can bridge that gap and say hey, come work for me. I’m going to train you on how to talk to people, I’m going to train you on some really hard skills here like tree identification and landscape analysis and these sort of things and you’re going to have the character there, someone who cares about their school and cares about their professionalism and developing themselves. And you’re going to have a great person you could potentially hire. Maybe so you just hire them for the summer or you hire them for a couple of weeks or a couple of months, right? Don’t think in crazy long increments. Think in short term in the beginning and find that character in an intern or a student and then you can maybe convince them to stay on longer if you do your job with the other stages we’re going to cover here. 


So, on the fine side, of course, we can jump through and we just named off a couple of those things. So, once we identify draft picks or trades, which ones we’re going to go with, we’ve talked through kind of finding them, one more thing I would add there is moving yourself away from the job boards, right? Every single landscape and tree care company out there that’s hiring for an estimator, that’s hiring for any kind of managerial staff, they’re all writing the exact same post carbon copied on ZipRecruiter and Indeed and all these sites. So, what does that mean? If I’m looking for that job, how do I differentiate between you and the company down the street, right? It’s the exact same methodology we would use from a marketing and sales perspective. We want to differentiate ourselves as a business so that our potential clients are interested in working with us. The exact same logic happens with employee pools. Treat it like a sales process. How can I identify or position myself as a very great place to work and a better place to work than the guy down the street who’s also looking for the same thing, right? So, think about it from that marketing perspective of how you can draw that attention and ways to do that are exactly what I talked about, focusing on people that like the outdoors, that like volunteering, that like to kind of save the ecosystems or like working with people or need a part-time job, right? Find the pain point that they probably have, align that with what you can help them and offset. 


So, the third step here, we went through identification, the finding portion. The third step here is the hiring process and this is definitely challenging, very awkward for a lot of people and they normally don’t spend a ton of time going through this because as humans, we act very emotionally, right? So, we interview 30 people. One guy we have a good conversation with. He’s kind of like us. We usually attract to people that we’re like or similar to and we go yeah, I could see myself working with this guy or him working for me. I’m going to hire him. And we just make this guttural just initial decision based on no real facts or merits, just that we had a good feeling, this gut feeling. That’s complete bullshit, right? You definitely want to have a good intuitive feeling about someone but back it up with the facts, with the data. Make sure that you have your set parameters in place. If you’re looking for character, don’t get distracted by everything else, right? People can put on a show like anything else. You don’t want to be the kind of used car guy and get kind of thrown into the mix by this guy who put on a great presentation but ended up being a terrible employee on the long end. So, when we go to hire and it all goes down the interview and how we’re going to really kind of weed them out. 


So, I break down interview questions or interview disqualification into kind of three groupings. We’ve got sort of behavioral type of questions and information we’re looking for, we have situational questions and then we have emotional questions or emotional intelligence type questions. These all have their own focus. I’ve got a couple links. You’re going to be able to find in the show notes where I have a list of 10 or 12 different questions for each one of these sections. But I’m going to rattle off a couple of these here. So, from the behavioral standpoint, you really want to get an idea about how they think about their life, right? So, these can be questions about kind of where they see their career going, where were they happiest when they were working last or when they were in sports or in school, what are they looking for in an employer, what is the idea of a dream job to them, what are their passions outside of work and what they like to do for fun. You can ask questions like if money was not a concern, what would you be doing? What’s ideal for you? What would you spend your time doing, right? This gives you a ton of insight into the behavior and where they kind of think about themselves in their business and the work professionally that they’re going to do. Very helpful to unpack these sort of type of person or that character. 


So, coupled with that is going to be the situational questions. These are going to be much more sort of tactical. You don’t have to put them in the here sell me this pen and any of that kind of like tacky type stuff. It’s more about let’s talk about business professional situations and figure out what in their experiences help them through these or maybe has not. Maybe they have no experience in this and that’s okay but identify that now versus down the road when you already hired them. So, instead of asking what is your sales experience, ask them what has happened in your career thus far to prepare you for sales, to prepare you for estimating, to prepare you for this level of a job? Why do you think that you’re a good fit here? So, you want to talk about challenges and issues they may have faced in a previous workplace. You want to kind of tee up a situation and get their take on it. So, like when’s the last time you were on a maybe it’s a team at school or you were in a group at college or you’re working for another company and there was a situation that you outright just disagreed with your superior or maybe just someone else that you were working with? How did you go about that? How did you kind of demonstrate your ideas without it becoming a screaming match? And you want to kind of really listen to what they’re saying. They’re going to describe how they think about these problems and it usually throws people for a little bit of a loop because they’re very critical questions. You ask them about their accomplishments, right? So, what in your experience thus far are you most proud of or what are you least proud of? What are the mistakes that you’ve made? 


So, these are very situational so you can get an idea of how their brain works and how their actions work in addition to those behavioral questions. You can see it sort of in action. And again, check out the show notes for a link to an article that I wrote that kind of lists out a lot more of these questions in detail. But those situational questions are really useful for you to think in your mind about what this particular potential employee may do on a job site or interacting with a customer, right? So, there’s going to be situations where the customer’s going to think one thing and the salesperson said another thing and they’ve got to sort of argue their perspective or they have to come to an agreement or compromise on something, right? Those situational questions help you kind of unpack how they might react in that or what their character says about how they may react. 


The last section here is the emotional intelligence question. So, again, this is all going to be around behavioral, sort of what their actions look like; situational, sort of what looks like in real time; and then the emotional side is kind of more high level, kind of how they react to things and again, just where they look at themselves from like a self-inflection standpoint. So, the number one question that I’ve heard—and this has been backed up by many, many studies. I did it in my own business and it was very successful. Several of my contacts have really enjoyed the successes of this question as well. The question is do you consider yourself a lucky person and it might sound like kind of an odd question to ask but it’s unbelievably revealing about the character of an individual. What it says is people typically fall into two camps. You’ve got the first set of people who go yeah, I consider myself a pretty lucky person. I was born into a healthy lifestyle and my parents treat me well. And yeah, so, I’m always looking for new opportunities. And that’s a great way to kind of look at how they think, right? And then you’re going to have a lot of people when you talk about like that really sort of negative mindset that goes into these conversations and they’re going to talk all about how they missed an opportunity and this guy got lucky over them and they didn’t get to get in a good school and it was somebody else’s fault. And if you just let them talk and as they explain different situations, say tell me more about that and let them just rattle off their idea about being lucky. It reveals so much about someone’s character. 


I have a couple of family members who are this way and it’s like they’re always looking for that miracle, one needle in a haystack situation. They’re going to hit the lottery or they’re going to meet this guy and he’s going to give them this windfall of money, right? And they’re just sort of waiting for life to fall in place for them instead of actually doing something about it. The people that think that way are going to reveal themselves with a question like this around luck. It’s a misconception out there on how people think about it and it shows kind of where they position hard work and their control, the controllable elements of their life versus what they think is out of their control. People that are blame gamers and negative minded, they’re constantly going to be talking about how everything is out of their control and they just sort of float around and whatever happens. Typically not a great person to try to hire because they’re just going to sort of float through life and assume that if this doesn’t work out or they’re not going to put the hard work in that this isn’t going to be a fit and it’s going to be your fault. They’re always blaming outward. So, great question to ask. 


All right. So, that kind of rounds out the sort of hire portion here. Once you find that ideal employee, you go through these situational, behavioral and emotional questions and you find the core employee that you want to hire, that character that you want to hire. And again, they may have relatively no experience in the field. We want to bring them on board. So, what do we do? How do we think about this? Well, the first thing we want to do from a training perspective as we move into this second to last stage here is what does it look like to onboard them? And going back to our initial conversation about identification, right? We don’t want to abdicate where we’re just dumping okay, you’re now an estimator. Here’s your stack of estimates. Good luck to you. And then it blows up in our face and they undervalue work and they don’t show up on time and all these things spiral out of control. We want to look much more at delegation and the only way to delegate is to have a system or a strategy that outlines what the expectations are, right? 


So, when you’re going through this, the number one thing I think you can do is to have documentation systems in place. I love using technology for this, right? So, if I’m going out to estimate a property and I’ve never looked at a tree job before, in my head, it’s going to be extremely overwhelming as a net new green employee and I’m going to look at the owner or the other salesperson that I am shadowing and I’m going to be incredibly overwhelmed with questions. Well, how do I know how big the tree is? What piece of equipment? Where do I park and what is the customer’s budget and what crew do I need and when can we get here and what type of tree is that? What’s pruning look like, right? These things are rattled off in our heads that we think about instantaneously and without much thought because we’ve been doing it for years and years. It comes second nature to us. 


You cannot expect any employee even an experienced employee to think that way. It’s unfair to think that your life experience equals their life experience, right? You’ve had certain things happen to you and you’ve been in this game long enough that those things are second nature. And so, you need to find a way to sort of crystallize that message to someone else so they can learn it and one of the best ways to do that with technology is to think in terms of if-this-then-that. It’s kind of a technical term but it’s more about thinking of if I show up to a property and the tree needs to be pruned, then I’m going to take these steps, right? If pruning, then this. And you just want to go through that exercise as an owner and think about as many scenarios as you can. And so, if I show up to a landscape property and I see that there’s water in the front lawn and it’s like pooling, then I want to talk to the customer about a drainage system and ask them about their gutters or I want to go to this next step, right? So, in our head, we go through this sort of decision tree all the time as estimators but we never write it down. We can never follow the logic and it’s really hard for someone who doesn’t have that experience to think and follow you. So, if you can write it down and sort of go through in a form or with software is a great way to do this with things like SingleOps and the programs out there, you’re going to be able to templatize how you think about an estimate.


And there’s going to be components, right? I’ve got parking. I’ve got access to the tree or access to the backyard. Do I have to use the gates? Do I have to take the gate off? Do I have no access at all and I’ve got to use a crane, right? These are the factors that help us arrive at our pricing and if you start to boil them down to the least common denominator, they’re going to be simple questions that you ask yourself in your head when you’re walking the property and you answer and use those answers as part of the criteria that you price by. So, just start documenting those things. Okay, here’s where I park. Here’s where the guys are going to access. Whatever the scope of work is. How many guys do I need to get a job like this done? Okay. What type of equipment do I need for that? Is this a job that needs a permit? Do I need the neighbor’s approval, right? So, you have all these questions. If you start to write them down, start thinking about them. Software can allow you to have check boxes and drop downs and fill in forms and tags so that the person can simply work through a form and make sure they’re not missing anything. This is a great entry way for them to start thinking about how to price instead of you just sticking your hand up in the air in whatever way the wind blows, that’s the price you yell out which is how a lot of people operate. You can’t expect somebody else to learn that way. So, you have to delegate by explaining this information in a very consumable way and the best way to do that is through forms and through technology or you can use a sheet of paper if you had to. But make it simple, right? 


Ideally, we’re hiring younger people that are probably more technologically advanced. Software is going to be second nature to them. If you can drop an app in their hands in the field that shows them what your brain is going through when you’re walking a property, it is so much simpler to systemize how you price your work, right? And when you’re doing larger landscape installation, hardscape work, this gets more and more challenging because you’re not typically giving a price in a three minute walk around. But you still have the same way in which you can templatize how you walk on a property. Large patio, pool installation, what have you. You’re going to take pictures, you’re going to take measurements, you’re going to ask questions, you’re going to look at the pitch and the grade and the drainage and the type of block and compaction and all these things, right? Again, just a series of if-this-then-that questions and if you can help the person, this new hire think that way, you’re going to be arming them with the skills on how to break down most jobs, right? And you can’t expect them to know every job. There’s going to be many complicated projects that come up that you’re going to need to help them with and that’s perfectly okay. We want to focus on much more of the rules versus the exceptions, right? There’s going to be those one-off jobs that are very challenging that we need as many team members as possible in place for. So, once we get sort of the logic on the questions we ask ourselves when we’re walking the property and we put that into a tool or something consumable that they can use and work through very simply, then we start to give them a really clear expectation of the methodology. 


And then the second piece of that is okay, well, we also have to input some things in here and those inputs typically come in the form of time and materials, right? So, great, Sean, I see that there’s a box on here that says man hours but how do I know or how does that employee know how many man hours it’s going to take on a job? So, this is where it gets a little more complicated because it can be kind of subjective based on their opinion or what they think it’s going to take, right? All estimations or all consultations are is us making sort of an educated guess on how much this is going to cost us within our profit margins and make sure the customer is comfortable with that, right? So, that hopefully we guess correctly and we put this together correctly so that we make money at the end of the job. And so, once they know the form and the methodology of questions to ask themselves, then we have to kind of train them on what to expect as far as those inputs like man-hours and quantities. 


Quantities are typically fairly straightforward because they’re normally backed by measuring. So, I’ve worked with a number of companies that have kind of systemized this from the tree care perspective too where they could actually shoot and measure how tall tree is, they can measure sort of the DBH or the diameter-breast height, right? So, at a certain level, they can measure around the tree, figure out how large it is and then they can sort of work backwards to figure out what they should be charging because they can actually calculate on a removal like how much cubic yardage of debris would be removed. I’ve got 100-foot tree at this size diameter. I know that that’s going to be roughly 15 yards of material removed or whatever that looks like. So, quantities are usually pretty calculable or measurable, right? We can measure how many yards of mulch by length times width. We can measure how much stone we need and how many yards of sod or whatever that might be. Trees and pruning can be a little more subjective, a little more challenging and that’s where it comes in where it’s labor induced. We have to think about how long it’s going to take someone. That’s probably the most difficult part to get. So, measurements we can sort of outsource to them through this ability to input into like a technology or a calculator or just record what those measurements are. 


The second piece is really those hours. So, unfortunately one of the only ways to get an idea is to have some sort of tactical experience with how long work takes. Definitely a difficult thing to teach someone. There is a feel to it. So, what I usually suggest and what I did in my business is I would have in addition to that employee shadow me or shadow the other estimators, I’d have them spend an extensive amount of time shadowing our core foremen or our teams and not even just standing there, like literally making them work as a brush dragger or work on the lawn crew or work on the landscape labor side for a couple of days and it’s going to be really tough, grueling work but they’re going to get a realistic expectation if they go through that for a couple of weeks on what it takes to get work done and that can really help them. And if you work with the foreman and have the foreman sort of download his ideas on how he thinks about the flow of a project, that new hire who may be net new to the industry is going to get a great exposure to how long things take and what kind of work is required to get different types of projects done. 


And you can use this on a sliding scale, right? So, if you’re doing a small patio at 200 square feet, you can show them by them working and being a part of that project what that looks like at 100-200 square feet on small levels and that it takes 36 man hours and these are the different components to get that work done. And then you can scale that onto larger projects, right? So, you can see that it takes eight hours to do the excavation on a 200 square foot patio. Well, now you can figure out that it’s going to take that multiple at a thousand square foot patio. Same idea for something like trees, right? It’s not a perfect science but the idea here is you want to give them the in-the-field experience to understand the amount of laborers and how brush gets dropped from a climber and how long it takes them to get it into the chipper or whatever that might be, right? So, you can kind of work backwards and give them that field experience to see okay, I physically have to drag the brush. 


And it gives them this sort of insight into the orchestra that is the work that we do, tree care work, landscape installations, even lawn maintenance and other maintenance oriented services, right? There is a beautiful sort of synergy in this orchestra that happens. Typically, the only way to get that sort of insight is to see it in action and be a part of it because you’re going to get run over if you don’t pay attention, right? So, you have to kind of understand the flow. And so, I would always make our new green hires spend at least a couple of weeks with the crews, understand that they’re the low person on the totem pole and they’re learning how to price things out and that’s a great way to get them that exposure if they’re brand new and let them get the feel for how things move on a job and you’re going to get the insight from the foreman or the climber or the ops manager, whatever you call them in your business, they’re going to have all sorts of ideas, right? You don’t always want to take all the experience directly from the owner or directly from another salesperson but they can get both sides, right? 


So, they get the exposure from management telling them how they want a price and how they do it and then you get the real in-the-field experience and feedback from a foreman who says listen, Sean, I know what John the owner says. But here, when we’re looking at a job, I’m going to give you what our concerns are as a crew. Here are the things that we think about. Here’s the challenge, the hardest part of my job. And what you’re going to hear from them is how you can help make their life better once that employee gets to be a full-blown salesperson, a full-blown estimator. And so, they’re not just guessing at whatever management said, right? They also have sort of a tie in a relationship now with the field and how hard the work is and they’re going to be much more sort of empathetic to that type of work by experiencing it and they’re also going to have an understanding of that flow and where they need to be and okay, well, I know we’re just looking for placement of the crane on this property but I want to look a little deeper than that. Okay, well, where specifically I’m thinking back at those three last crane jobs I did and here’s what the foreman told me was a challenge. So, I want to make sure I account for an extra hour on this job to put down that because we have to run equipment back and forth and there’s this issue over here, right? And so, it’s this aggregation of the management and these forms and the decision tree of how we go through and estimate a project and then giving them that sort of unbridled feedback from the field, from real staff, boots on the ground is doing the work without the owner present is going to be a great loop of information, right? So, it helps complete this circle of knowledge that they need, right? So, we’ve got the strategy on that side; the technology, templatizing pricing and the if-this-then-that scenarios and what to look for in jobs; and then we have the tactical training of them understanding the flow of work. 


The last step I would say is just when you’re thinking about the strategy of all this, you want to be hyper focused on the skills and the merit and not focus on the time of this. So, training is very expensive. It costs a lot of money to train somebody, basically paying them without doing any work. And so, what we have a huge challenge with as an owner is we want to try to get that person trained as quickly as possible. And so, we end up skipping steps just to save some money and it’s a terrible, terrible idea. You really don’t want to fall into that spinning wheel. What you really want to focus on is the skills and the merit. And so, what you want to have is make sure that when you get them through a training process that they don’t move onto the next level until they have gained a skill or they have some sort of competency or merits in what they have achieved, not just okay, you’ve been training for seven days, time to move on to the next section. 


Because people learn at different levels, right? You throw them in for a week on the crew and maybe they’ve got a great experience and they had an awesome understanding and you have like a little quiz or a little form that they fill out to give them the feedback that they have but also ask them questions on specific kind of testing on what the field was like. Maybe they blow through that with flying colors because they really resonated with the guys in the field. So, that would be a skill or a merit or something that they understood and now have in their sort of rolodex of experiences. That makes sense to move them onto the more sales oriented stuff or the technology and the templates of actually pricing work, right? Where somebody else, it might take them three weeks in the field because they just really can’t conceptualize these ideas and really struggle with the field side of it. And so, it might take them three, four weeks to go through that. You’ve got to let people learn at their own pace and make sure it’s based on those skills or those milestones that are merit-based and not time-based. That’ll throw you in a lot of trouble if you just wait on okay, it’s been two weeks, I know you don’t have all the skills but just throw you out there and see what happens. That’s going to really blow up in your face. So, definitely focus on the skill building versus the time that’s elapsed in training. 


And as we wrap up here, we’re going to talk about the retaining, right? Retainment of our employees. So, now that we’ve went through training, we’ve onboarded them, they’ve spent time in the field, they’ve spent time shadowing us or one of our other estimators, they’ve learned about the if-this-then-that on a job site, they’ve learned what to look for, they learned the technology on how to analyze a property and where to put things in the forms and drop-downs and they’re very comfortable and they start going out. They’re ready to start pricing work on their own. They jump out there. The main thing to do once you get somebody sort of live and fully active or quota carrying in your business, you need to have strategies in place to monitor that as well. So, the number one thing I look for is the KPIs or key performance metrics and these are going to be things you’re tracking on that employee. 


One of the other traps I find a lot of business owners fall into is they have incoming estimates, they have this huge demand for calls to get estimates created, get consultations completed. They get somebody half-assed trained in the system. They just throw them out there into the mix. And then they start pricing work and you find out that there’s never really sort of a post-game analysis on the estimates they put together because you’re using paper or you both are so busy, you never have a chance to sit down and go over their pipeline or the type of work that they’re pricing. And then you find out that they’re pricing work too low or they miss something or you simply have no idea what’s happening with their day-to-day because you have no way to track it. And so, this is where technology becomes unbelievably powerful as a force multiplier in your organization. You have now delegated a particular experience, particular tasks off your plate, particular responsibilities and it’s sort of a black box because the second that you delegate it and you’re not doing it, when you’re using paper or you’re just letting them sort of run the show, you are now sort of at arm’s length from those experiences or those responsibilities. And so, if you’re using these outdated methods, there’s no way of knowing how successful they’re being or if you’ve made a huge mistake or not because you could have done all the training, all the best onboarding possible but if you have no way to track what’s happening with what they’re producing, you’re kind of flying blind. 


So, technology is incredibly powerful because they can have a log into the system, right? So, they’re going to be going through their estimates and you’ve already templatized these estimates. So, they know the if-this-then-that’s. They know the things to look for. They know the questions to ask. They know the experience to think back on to figure out the man hours and the measurements. And now you’re giving them you the ability to see what they’re producing, right? So, you sort of teed up a great proposal or a template for them to work within and now you get to see how they are actually pricing that work. So, are they following the rules? Are they following what you set up for them? And so, a good software program is going to allow you to look at each estimator and see what did you sell today, tell me about the proposals you looked at and you can look in the system and see okay, you did these five estimates. Let me unpack these. And without even involving that employee in the field or on the go, you could just open up each proposal that they create and look through the details. Okay. How many man hours did you put on this? Let me check the pictures. Okay, well, that looks like they’re a little, they’re not considering this or that and maybe this pricing doesn’t look right and it looks like they mixed up some of the verbiage or the language wasn’t correct, right? 


So, you get to sort of see this feedback loop of what’s going on out there, what they’re saying to your customers and make sure that their pricing work effectively and efficiently because they may be pricing too high or pricing too low, right? And those things, their ideas and their methods, we want to catch before they spiral out of control. And so, with software, we can look at that as quickly as possible and you can also like what we did in my business, after they got through onboarding and they became sort of self-sufficient, I still required them to create the proposal themselves but then I had to approve it before it got sent out at least for that first few weeks once they passed sort of the credentials or the merits or skill that they were able to price things on their own. So, let’s say the first 25 proposals they put together, I’d have them create it in the field and email it to me first or I’d have them just let me know when they finished that up and then that evening, we would sit down and go through 5, 10, 20 of those proposals. Figure out where they missed the mark, where they need to improve, help me better understand the job and then send it to the customer, right? So, it’s just this extra layer of sort of accountability and expectation setting from your perspective. 


And once you get through those say 20, 30, whatever the number is, it doesn’t matter, where you feel they’re comfortable and they feel they’re comfortable and they’re on their own, well, now you can just sort of manage from a distance, right? So, you see how we just put these building blocks in place. We didn’t just dump things on their plate and then wonder why they didn’t work out the way we wanted. We set these crystal clear expectations. They got all this experience in working for our company. They then were able to have us walk through their specific deals with them to make sure they’re on the right objective. And then we were able to let them out on their own and track that ongoing. So, if something got missed or we wanted to unpack maybe their follow-up process, the software, the tools, the technology, our system that we build, we’re leveraging the process and not the person, right? Because if we’re all on that person, we’re just assuming that they’re calling and following up on their leads. We’re just assuming that they’re actually pricing work correctly and they’re not doing anything nefarious, right? 


But with software, with tools, with the system, we’re leveraging that process. So, we can track it, we can adjust it, we can see things before they’re going to get blown out of proportion and the person that we hire has this great level of accountability so that if they were to miss the mark or they’re just being inappropriate, not being professional, we’re going to be able to see those sort of things and have real grounds for having unemotional conversations with them, right? So many of us fire someone because they missed something or whatever it was. Sometimes it’s not their fault where sometimes it is their fault and we just didn’t know about it until six months in line and we just lost so much money because of it. So, it’s this idea of tracking, painting this picture of like what success looks like. And so, that retainment on your end really helps you know that you’ve got the right people in place and if they’re not, you’re also going to be able to track where they’re missing the mark, where they’re not following directions, where they did not live up to the expectations that you set in a very clear manner. And then it’s easier to let that person go because they did not follow the rules that were set in place. So, that’s kind of the management side. 


What retention really has to do with though is how you convey why it makes sense to stay with your organization in the long term, right? So, one of these pieces from sort of the culture building standpoint, I always refer back to this quote that I heard from Reid Hoffman who was the founder of LinkedIn and he talks about this idea of going for instead of careers and these 30-year long engagements that people go and work for IBM for 30-40 years, he says focus on what he calls tours of duty, right? Two years, three years, four years maybe. These smaller increments of time when you talk about Millennials, when you talk about anybody, I think the average right now in the corporate world is like 18 months or less than 24 months when people switch jobs. Every year and a half, two years, they are changing organizations, right? That means you have to just prepare for it. You can’t just say oh, people just leave. That’s just part of how business is done now. That’s how people interact with their employers. So, yes, you want to try to keep them around for longer but you also have to face facts that they are going to leave. Even if you did everything perfectly correct that you had control over, they could likely want to move on to something else. 


And so, it’s about painting that picture of what advancement looks like in your organization or tying back to the first part of this conversation around finding and identifying the right types of people, when you’re doing that, you’re asking them a series of productive, thought-provoking conversations or thought-provoking questions that sort of reveal their core intentions, where they’re looking to go. Maybe they’re going to tell you in that interview that they really want to be a teacher but they’re not ready to do that yet. So, they want to kind of get real world professional experience in the next couple of years and then move on, go back to school and become a teacher in their late 20s, right? If you know that up front, you can help craft their career or craft your company as sort of a launching pad for next steps for them. And that might sound crazy to say oh, I don’t want to prepare them to go hand them off to somebody else. But it’s likely going to happen, right? So, you can cry in the corner and just say that oh my God, people just never stay or you can embrace it like you embrace the fact that there just aren’t enough people out there to just trade for another employee and you have to create your own. 


It’s an acceptation of the realities and you can say what can I do to make their experience here as wonderful as possible, train them, invest in them, hold them accountable, allow them to hold us accountable so that maybe they don’t want to leave, you treat them so well they don’t want to leave. But if they do leave, they’re going to hold you in high regard. They’re going to leave amicably and you’re going to be this launching pad for further careers, right? How great would it be to interview an 18-year-old kid and give them the information of a 30 year old that just left your company on perfectly good terms and have a conversation with that person and say hey, tell me about your experience in working for your landscape company, your tree care company. And they can say Sean and his team did an awesome job. Man, they just helped train and nurture me throughout my whole process. I knew from the beginning that I didn’t want to have a career in this industry but I wanted to move on to bigger and better things and they helped me get there. They helped me achieve and grow and sort of aggregate these life skills to move onto the next stage, right? 


That’s a great place to be in as an employer and if you do your job correctly, hopefully they don’t want to leave but if they do, you’re going to be this person who has built a system that can keep bringing in that high quality of character that you can keep turning out, right? And so, you’re doing that through painting the picture of what this process is going to look like, right? Because you’ve thought of all the structure and the expectations and how they’re going to succeed. You’re going to track them, they’re going to be able to track themselves and more importantly, you can paint the picture of what advancement looks like. So, maybe after they get through the sales estimator role, maybe they really want to manage people and they want to become your ops manager or your whatever that looks like in your company. You can show them what they would have to do in the next step to get to that next role, right? So, if they want to be a manager, maybe they have to learn new skills and they have to shadow different people and they have to get the tactical experience, right? Circling back to where we started with training getting the field experience. You can keep showing them how people level up by demonstrating or illustrating what these beautiful things look like in your organization, that you thought about what career advancement looks like. If you take that seriously and you show them that they’re not going to be dragging brush or weed whacking or digging holes for the next 30 years, you’re going to get this buy-in from people where they see that they can move up, right? 


I’ve talked to several very large organizations that hire hundreds of hundreds of people and they always will interview or poll their employees at the entry level positions and they all say the same thing. They do not see themselves being a weed whacker, being a laborer, being a groundsman, weed whacker or whatever that might be forever. They don’t see that as a career. And so, that means that if you keep them there and that’s all you see them as, they’re going to leave at some point. So, why not just accept the fact that they’re going to be an entry level, paint the picture of career attainment or advancement, here’s where you can go you get these skills and you follow our system. So, now instead of having to lose them altogether, you just move them up and then they can help train the next new guy that came in green entry level, right? And you see this whole large complex system that you’re building, process that you’re building that helps you cultivate your ideal employee rather than complain that there’s not enough of them out there. 


So, I hope that helps, guys. I tried to round that up to basically how we think about this from the identification of what we want and those draft picks versus those trades and then circling down to how that goes into hiring the next person below them and it’s this continuous circle. And we really have to focus on building that process and those tools and techniques for tracking and for training and for accountability so that we can have more of those employees come in without experience and be able to move them through our organization. So, I think that that’s a lot of resources in there. Please check out the show notes and check on some of those links to articles and some other ideas. I’d love to hear from you guys. I know we couldn’t go into tremendous detail on every one of these things but I’d love to hear from you guys what you thought about this, where you want to expand, what ideas you’ve had that have worked really well. 


Please reach out. You can email me directly. It’s Sean, S-E-A-N Adams at You can reach out to us or comment on any of our social media platforms. We’re very active on LinkedIn and on Facebook if you want to reach out and we’d love to hear your feedback on any of these ideas, any things that are working for you guys so we can help share them with the audience and move forward from there. Guys, I really appreciate you taking some time to meet with us today and talk through these ideas or listen to me rattle on about these ideas. So, really appreciate all the help. If we could have one ask apart from your feedback from the show, if you could on particularly Apple podcasts but any of the places, the platforms you listen to, if you could drop us a five star review with a comment. If you’re getting value out of this, we’d love to hear from you. It really helps us spread our message and get this podcast and this content out to more people like you. Thanks again, guys. We’ll catch you on the next one.



Thanks for listening to this episode of Green Industry Perspectives presented by SingleOps. If you got some value out of this episode, drop us a five star review on your favorite streaming platform and don’t forget to become a pro member of the podcast at As a pro member, you’ll get notified of each new episode, access to exclusive bonus content and be entered in to win some great prizes. Thanks for listening and don’t forget to tune in next week. 


Back to top