May 21, 2017

JF992: How to Develop and Scale Your Team #SkillsetSunday


Are you a one-man show? You may collect all the checks, but you’re not going too far. Today you will learn about how to build and develop a team, but more importantly, why you should have a team.

Best Ever Tweet:

Shawn Casemore Real Estate Background:

– CEO of Casemore and Co Inc.; A global consulting firm for CEO’s and businesses
– Author of “Operational Empowerment: Collaborate, Innovate, and Engage to Beat the Competition”
– In past two decades worked with organizations such as Pepsi Co, CN Rail, Tim Hortons and Spectra Energy
– Published over 1000 articles, booklets and resources on improving individual & organizational performance
– Based in Ontario, Canada
– Say hi to him at 

Click here for a summary of Shawn’s Best Ever advice:

Made Possible Because of Our Best Ever Sponsors:

Want an inbox full of online leads? Get a FREE strategy session with Dan Barrett who is the only certified Google partner that exclusively works with real estate investors like us.

Go to to schedule the appointment.


how to develop your real estate team

Joe Fairless: Best Ever listeners, welcome to the best real estate investing advice ever show. I’m Joe Fairless and this is the world’s longest-running daily real estate investing podcast. We only talk about the best advice ever, we don’t get into any fluff.

I hope you’re having a best ever weekend. Because it is Sunday, we’ve got a special segment for you – Skillset Sunday. By the end of our conversation today with our Best Ever guest, you will know how to develop your team better than how perhaps you’re currently developing your team, and creating your team better than how you’re currently creating your team.

With us today we’ve got someone who has 17 years of developing his own team, and he currently helps entrepreneurs develop their own team. How are you doing, Shawn Casemore?

Shawn Casemore: Hey, Joe. Thanks a lot for having me.

Joe Fairless: My pleasure, and nice to have you on the show. A little bit more about Shawn – he is the CEO of Casemore & Co., a global consulting firm for CEOs and businesses. He’s the author of “Operational Empowerment: Collaborate, Innovate and Engage to Beat the Competition.” He’s published over 1,000 articles on improving individual and organizational performance. Based in Ontario, Canada. With that being said, Shawn, do you wanna give the Best Ever listeners a little bit more about your background and your focus just to add some context to our conversation?

Shawn Casemore: I’ll try and stay as focused as possible on your audience, Joe. My experience was about 17 years in different corporate environments, different companies, different [unintelligible [00:03:40].21] different sectors, and I always had a team, since the age of 23. I’ve had unionized, non-union, two people working in remote locations, up to 95 people in one location… That experience of over 17 years lead me to wanting to launch my own business, and what I’ve specialized in and what I’ve kind of found that my specialty is is in helping entrepreneurs/business owners understand how they can get more out of their team. And when we say ‘team’, I realize some of your listeners may have not had employees, or maybe some that just have a team of folks that support them to run their own business from a marketing standpoint… So what we’ll talk about today and some of the tips I’ll share really addresses your own employees, if you have a team in that regard, or if you have multiple teams in your business, but also if your team is not so much full-time employees as it is contractors that support you, these tips, techniques and ideas will be applicable.

Joe Fairless: Yeah, I undersold what we’re gonna learn… It’s not just about team development as you said, it’s how to get more out of our team – even better. So it directly applies to the bottom line. How do we wanna structure this conversation, how do you wanna lead it off?

Shawn Casemore: I guess we could start with this – if you could give me some of the challenges you think your listeners face (one or two challenges), what I can do is probably tie that back to their team and how to overcome those challenges.

Joe Fairless: Okay, cool. One would be people who are looking for deals – so it could be a fix and flipper… Someone who buys a house, fixes it up and flips it to someone else. Their challenge might be either finding enough deals or finding the right contracting partners, so the people who are doing all the work. Those would be a couple challenges I could think that they have.

Shawn Casemore: Let’s start there. So in this case let’s look at the team. I’ll address both of these, but we’ll start with the contractors. The team – if you’re gonna be successful in fixing and/or flipping, obviously you need a team of different contractors, although you might have a general contractor. You need that team to support you, so they need to be able to drop everything and come running when you need them, although in their own business they might have to sustain other business and other customers, which means they’re not always there for you. The cost is always a factor – the more you pay them, the less profit you have. And the last thing would be when you look at your contractor as a team, you’re trying to get on the same page. This is your bread and butter; to them it might just be another job. So how do you get more to that relationship?

Step one – when you think about any contract at your business, and by contract I don’t specifically mean a general contract, but any way that you pay an hourly or by job basis, you have to realize those folks have their businesses and have their own priorities, and therefore you need to somehow make your business their priority. I’ll say that again, you have to make your business their priority. Now, the logical ways that we’ve seen this done, even if you watch some of the shows on TV, is that the investor goes out and they beat up on the contractor, they yell and scream and rant and rave and threaten to pull business… That looks good for TV and that’s why that’s on TV, but in reality that’s not the way it works.

So you have to figure “How can I make things in my business just as important as their business?” You can do that obviously through leverage – the amount of business you give them – but more importantly you wanna make them feel like they’re a part of something. For example, when you’re going out to take a look at a property, you bring your contractor – we’re talking like a general contractor – with you. Do you involve them in the decision-making? Do you actually give them the chance to take a look at situations and provide potential solutions, and when they do, do you thank them for it and you take some of their advice?

I see it in myself, I’ve been involved in real estate now for probably only about 5-6 years as kind of a side venture, something I enjoy, and really to build that team when I’m kind of a solo investor, it becomes trying to ensure that other people who support me, although they’re not an employee, they feel like this is also their business. That comes back to building a relationship, which includes things like trust, honesty… And you’ll find that a lot of contractors will be very receptive to that, because everybody else treats them like crap, so they’re happy to work with those who actually treat them like a human being, respect their ideas and viewpoints, and treat them as if they’re part of your business.

Joe Fairless: I love that. Involving them… One thing that I do with my team – I’m not a fix and flipper, but I have teams for my company, and I always make sure that I mention it’s not MY podcast, it’s OUR podcast. I have that mentality because it truly is ours; it’s the team, it’s not just me, and I think that has a psychological benefit as well. What do you think?

Shawn Casemore: Absolutely, it does. It really comes back to — I think in business sometimes we end up running over those who support us, and maybe inadvertently, because we’re so busy, we’re so fixated on the next deal, the next opportunity, cash flow… Those things absorb, I’m sure, much of the time of your listeners. But the problem is in doing that many of us, because we’re so focused on those things (they call it stress), we can come off as jerks, and then that inadvertently can be then thrust upon those who support us. And notice, we’re talking about a contractor here, but if you had employees on your team, the same thing can happen; you’re focused on cash flow, you’re focused on sales, you’re focused on the next deal, but that stress then when you turn to answer some questions of your employee or your contractor comes out that you’re a little bit of a jerk… And then what do they think of you? They think you’re a jerk, so are they gonna stand behind you, are they gonna be there when you really need them? The answer is no, and you’re probably gonna wonder “Hey, why is that? I’ve given them a solid job and I’m paying them for years, I’ve been trying to include them as a team…” So it becomes very difficult for the entrepreneur or the investor in this case to have a couple different mindsets going on. Number one – the business mindset, which is “the next deal, cash flow, profitability”, but also the separate mindset that is “Hey, in order to be successful, I can’t do this alone. I need people, be it employees or contractors or otherwise”, and people are receptive to other people. People are receptive of being treated fairly, being treated honestly. In fact, I can actually warm people up a little bit if I start to maybe go that extra mile or if I drop off a coffee. When I’m [unintelligible [00:10:09].04] I always try to grab some coffee for the guys.

Here’s a funny situation… I had a contractor and his team working last summer on this property that I had, and it was a really hot summer day, which believe it or not, despite the snow [unintelligible [00:10:20].25] I’m coming in, I’m rushing in, I’ve got a few minutes to stop by and see how it’s going and move on to the next thing, and I think “You know what? If it were me, here it is Friday at [3:30]; I’m hoping they’re gonna stay and finish the job”, so I stop and grab some beer. I brought it back and I said, “Hey guys, I hope this is okay.” I can tell you the contractor that lead that job became my friend immediately. Instead of bringing stuff to my house after house, dropping off stuff… “Here, I forgot to give you this. Here’s a deal on that…” Suddenly, he’s my best friend, and all I did was take a moment to step out of my agenda, my schedule, and start to think about them as people and realize “Well, what would I want if I were them? It’s a hot Friday afternoon, I’d want some beer”, right? It’s that mindset.

Entrepreneurs and investors need to focus on two mindsets: the business mindset and mode, but there’s also the people mindset and mode, which oft times is very similar to how you would deal with your customers. We’re suggesting you deal with contractors, employees with a similar tone and ideas that you would with your customers.

Joe Fairless: I imagine that the principles that you teach and work with your clients on through your consulting firm are similar principles that we as real estate investors can employ, so what framework do you use with your clients, when you’re working with them to get the most out of their team?

Shawn Casemore: Typically, what I would do is — every team is different, every organization is different. For example, I was just speaking with a client this morning; we are working with kind of a subset of a small group of people in the organization. We identified some very minor changes to something, and this morning we sent that out to the broader team before it went live and said, “Hey, give us your feedback. What do you think?” and interestingly enough, out of about 15-20 additional people this went to, two were just hands-down “This is crap, this is not gonna work.”

Joe Fairless: Fire them. Nah, I’m kidding… [laughter]

Shawn Casemore: Well yeah, but [unintelligible [00:12:17].14] they’re senior people, they’ve been around for a while. So the fun thing was leading up to this, everybody in the subgroups I was working  with said “Oh, there’s gonna be some barriers, there’s gonna be some problems”, and I said “What will they be?” “Oh, can’t tell you.” Well, it became very clear what they are – some senior people that realistically are just at a point in their career where they don’t wanna change.

Now, the one mindset is, as you suggested, Joe, fire them, get rid of them; they’re not gonna accept change, I don’t have time for this. But on the flipside you’ve gotta realize they’ve got – how many decades of experience here? This may be a matter of “I can invest a little more time with them to convince them”, but also on the flipside, “What am I maybe missing here?” So rather than let my desire say “Hey, screw them, let’s just move forward with this. This isn’t necessary”, I’ve gotta invest a little bit of extra time.

When you go back to “What’s the framework?”, step one is understanding that everybody on a team is an individual; they’ve got their own life experiences, which includes their personal experiences, their own work experience, their own ideas, and everybody wants to share those ideas and experiences. Some people will speak up and slap you upside the head with it, and the next person might not say “Boo!”, but everybody does have that information. So if you wanna create a stronger team and a better business, you need to really understand that everybody’s an individual, and deal with them on an individual basis to get the most out of them, to get these ideas that help them feel like they’re part of something. When you create an environment where that happens, powerful things begin to happen, people begin to feel happy at work, which we all know means they’re actually more productive, they start to share ideas more frequently, which as an entrepreneur we can’t think of everything.

So it really starts as simply as understanding that everybody is an individual, has their own ideas and viewpoints. Some of them might not be valid because they don’t have all the background that I do or others do, but a lot of people just wanna be heard. If you can listen to them and start to capitalize on some of those ideas, you’ll build a very, very strong team.

Joe Fairless: How do you treat everyone as an individual and hear their ideas, while still scaling a company?

Shawn Casemore: Here’s how we’ve handled it in the past – we put in layers of management. So your team starts to grow and you say “Well, I need a general manager to manage this team” or “I need a supervisor for this group.” And that’s okay, but the problem is when we hire those people, we usually pick the best person. You’ve heard that old saying, you get the top sales person and you make them manager of the sales department, now you’ve got two problems – number one, you’ve [unintelligible [00:14:39].03] your best sales person, and number two, that person may not be a good people person.

If you’re gonna put these layers in, you wanna pick leaders who are people-first, who are good with people… Because I can train any skill, I don’t care what it is. It might take me time, but I can train a skill, I can develop somebody’s skills. I can’t make everybody good with people. So when we’re adding these layers, that’s what you wanna consider, that’s step one.

But on the flipside, let’s say you’re not gonna have layers. You’re still small enough that you can scale for a while before you put leaders into place… You need to calendarize some time where you’re only dealing with your people, whether it be contractors or otherwise. This isn’t a stop by a property and just “Hey, how’s it going? What’s new?” If you’re gonna do it that way, schedule time to spend time with people. Make a point and realize it that as a business owner, as an entrepreneur, the people that are in this business are as important if not more so than me, because they’re making it happen. I may be putting the  deals together and shaking hands, but they deliver… So I really have to invest some time.

I tell leaders all the time: “Stick it in your calendar every Friday to spend the afternoon or the morning going around and just talking to people.” You might not hit everybody every Friday, but make a point of doing that, and what you’ll find is you’re able to better understand everybody as an individual, therefore when you’re positioning things, ideas, viewpoints, asking questions, you can position it from a perspective that they personally appreciate.

Joe Fairless: Let’s say we have a remote business… A lot of real estate investors have remote team members. Let’s say we follow your advice on scheduling time with our remote team members; we just jumped on the call, they say “Hi”, we say “Hey, how’s it going?”, we do the initial pleasantries… How do I approach that call? What questions do I ask?

Shawn Casemore: Well, step one, don’t have a call. If you look at the technology we’re using today, Joe, Zoom, Skype – there’s all these tools out here today that allow for face-to-face interaction. So preference number on  – and you can use mobile for it – I have a face-to-face interaction. Because think about any call you’re ever on; if somebody calls you, what are you typically doing?

Joe Fairless: I’m picking my nose right now while you’re talking.

Shawn Casemore: You write notes, you’re answering e-mails, you’re trying to type quietly so nobody hears… So if you get them face-to-face, you’ve got their attention, even if it’s for a short span, and you get a better feel for where their head’s at; are they really interested in this or not? It goes back to the old saying, body language is the most powerful communication tool we have, and yet in today’s highly technologically driven world we’re missing that piece. We’re wondering, “Why do I have to send 32 e-mails to get the point across?” Well, why didn’t you go see them? That would have saved you a lot of time.

So if you’ve got a remote team – and I have the same in my business today – I schedule time (if they have Skype, or Zoom, or something) where we get face-to-face. Maybe it’s only once a month, maybe it’s once a week, depending on how important that person is to the business and how frequently you can interact. And I can change that. If we start at once a month and that’s not enough, I pull it up to once every two weeks, and I set this [unintelligible [00:17:33].25] with the individual that “Look, I think it’s important that we stay connected. I prefer face-to-face, because it allows for both of us just to have a more meaningful conversation” and if they push back and say “I don’t want that, because I’d rather be at home in my PJ’s right now”, tell them “Just put a better shirt on and let’s go face-to-face. Give me the chance to give it a try first.” Face-to-face is key with those remote people to ensuring that you’re having a valuable dialogue.

Joe Fairless: Okay, alright. We’re seeing them electronically, via Skype or something, or we’re in person. Now what questions do we ask? How do we structure that conversation?

Shawn Casemore: It depends on their role. You start with pleasantries; that might sound so simple and stupid, right? You say “Hey, how’s it going? What’s new?” but the change that I would suggest a lot of entrepreneurs make when they ask that question is to actually pause and wait for an answer… Rather than just “Hey, how are things? Great! Anyways, here’s what I need from you…” – that’s typically how that conversation goes. So we’ve got in our mind going into this, “Hey, I’m spending 10-15 minutes, maybe 20, just trying to find out what’s going on in this person’s life”, so if they focus heavily on business, I’m gonna go there with them, but I’ll ask them how are things going personally. If they focus heavily on the personal side of things, I’m gonna go “Great! How are things going in your job? What’s going on right now?”

So it’s just that time to have a dialogue, and there doesn’t have to be a fixed agenda. The point is if you’re an effective leader and you’re dealing with people just like you would with a customer, you’re gonna change your approach. Think about this again from a customer standpoint – if you’ve got a customer that’s pounding his or her fist on the table, demanding answers, do you sit back and crack a smile and light up a cigar? Probably not, right? You’ll get them the answers quickly. Same if you have an employee that’s direct like that, I’m gonna respond directly. Or if I’ve got somebody who’s more thought-provoking and they wanna sit back and analyze things, I’m gonna mimic the same, because that’s how I break through that barrier of the fact that “Hey, I’m human just like you. Yeah, I’m your boss, but I appreciate you, I care about your ideas and viewpoints” and that starts to open up people to providing new ideas, being more creative and more supportive to my business.

Joe Fairless: So far what I’ve written down for takeaways for how to get the most out of our team is 1) make your business their priority by going the extra mile, making them feel like they are part of something, and/or involving them in the decision-making process. Another is don’t be a jerk – pretty simple. A third is to get feedback for what you might be missing. When you use that example of sending it out to 15 or so people, a couple of people who have been there for a while said “What’s going on? I don’t like this” – well, what might you be missing? And the fourth is everyone on the team is an individual and they want to share their experiences, and scheduling time with them in person as much as possible. I don’t think it’s “as much as possible”… I think as much as it’s required to get you your sweet spot probably, and then if you can’t do in-person, then do it via Skype or Zoom or something like that.

Anything else that we haven’t talked about that you wanna mention, that will help the Best Ever listeners get the most out of their team?

Shawn Casemore: I guess the last point I would bring up Joe is the idea that, again, if you realize that everybody’s an individual, you have to realize that recognizing people, thanking them has to also be individual. For example, let’s say you’ve got a few people on your team and you have a great year and you do the cliché send them all a jacket or give them all a ball cap. That’s fine, but if you’ve ever received the jacket from maybe a business you were working in at some point, some people love that jacket, some people would rather have the cash, some people didn’t like the color, some of them got their names spelled wrong… So when you look at recognition or just thanking people, that also has to be individual, so sometimes that’s a matter of with you, Joe, because we’ve got a great rapport and we get along well, think very similar, you may be a similar personality as me – I know I can pick up the phone and give you a call, and say “Hey, Joe, I really appreciate your hard work in that” and I send you a gift certificate for Dunkin’ Donuts, or something.

Somebody else, I’m gonna see them on the site, so I’ll go over and give them a pat on the back. Somebody else, I’ll drop some beer off to him. If you really think about that recognition and thanking people is also individual, because that’s the only way I can make sure it’s valuable to the person. If you do that, again, you’re gonna find people are more appreciative and more supportive of you and your business.

Joe Fairless: I know you’re gonna say it depends on the individual, but I still would like for you to tell a story of one of the best ways that you’ve seen or done personally the individual thank you approach.

Shawn Casemore: Personally, my experience has been — and everybody disagrees with me on this, or pushes back… But my personal experience has just been walking around, going to see people and just thanking them. Now, I’m not gonna say the same thing every time; I’m gonna change it up based on the situation. But hands down, most people just want a thank you.

Again, that thank you will vary depending on the individual. If it’s a shy person, I’m not gonna go over and pull them up in front of the team and make a big announcement, because that’s gonna piss them off. I’m gonna go talk to them at their place at work, their desk, or get on Skype with them and say, “Look, you put a lot of effort into that – notice I’m being specific about my thank you – and it was done on time, and that’s the best we’ve ever done… Just wanna tell you, I really appreciate that. I know you put some extra hours in to get this done.”

It’s that personalization that is absolutely key, but again, it’s just that face-to-face recognition. Most people, if you give them money, they just want more. That’s something I can use once in a while, but taking time out of my day when most people recognize as an entrepreneur you’re busy — so if you take time in your day to specifically go see somebody and say “I’ve got nothing else on my agenda, I just wanted to stop by and say thank you”, people are probably gonna be shocked at first, and after a while come to desire that kind of feedback, which again is a good thing, because you can build on that. You can start to take that to “I’m thanking you, and by the way, what other ideas do you have? How might we replicate this success again?” You just start with thanking them on a one-on-one basis.

Joe Fairless: Shawn, thank you for being on the show and talking about how to ultimately get the most out of our team, but it’s deeper than that… It’s also how to have a more enjoyable relationship with our employees, so that we all achieve larger things together. Because when we’re implementing the tactics that you mentioned – that I recapped already, other than that last piece of thanking the individual – then we will enjoy ourselves much more than if we are doing the opposite or not doing it at all, I promise you that. No one likes being a jerk, I don’t think, and asking ourselves better questions like “What else might I be missing?” and having conversations as much as is needed to reach that sweet spot of efficiency with our team members, in person or where we’re seeing them – that’s something I don’t do, and I will test it out and see the change in the results.

I have a daily call with my team at 8 A.M., Monday through Friday. They’re all local, but we don’t do Skype, we just get on the phone call, and I don’t see some of them very often in person. So I’m gonna implement that.

And then also making your business their priority – when we step outside of ourselves and we step in someone else’s shoes and we make it their priority, then ultimately our priorities are gonna be addressed and then some. I love your example of just paying $20-$25 for a case of beer to the contractors and all of a sudden guaranteed you’re making your money back that you invested in that case of beer and then some. Plus, you just feel better. I mean, come on, we’re on the journey together, why not enjoy each other’s company?

So thanks so much for being on the show… Where can the Best Ever listeners get in touch with you?

Shawn Casemore: Again, thanks Joe for having me. The best place to find me is on the web, You’ll find a lot of tips, resources, everything there about how to further develop your team. Also, you can google my name and you’ll find me on virtually every social media channel out there.

Joe Fairless: Excellent. Well, Shawn, thanks for being on the show. I hope you have a best ever weekend, and we’ll talk to you soon.

Shawn Casemore: Thanks, Joe.

Subscribe in iTunes and Stitcher so you don’t miss an episode!


    Get More CRE Investing Tips Right to Your Inbox

    Get exclusive commercial real estate investing tips from industry experts, tailored for you CRE news, the latest videos, and more - right to your inbox weekly.