423: Building a Positive Team Culture | Master Sales Series

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By fostering a positive team culture, we see better performance, higher employee retention rates, increased profitability, and improved employee morale.

Today on the Master Sales Series with our host, George Leith, we are talking about building a positive team culture. A great quote around this topic comes from Henry Ford:
“Coming together is a beginning, staying together is progress, and working together is success.”
Teamwork is a practice and a skill, a skill as leaders, collaborators, and colleagues we can embrace and improve on continuously.

We explore 16 ways to create a positive team culture.

  1. What are the Benefits
  2. Build a Culture of Success
  3. Set Goals
  4. Identify Values
  5. Respect
  6. Responsibility
  7. Commitment
  8. Continuous Development
  9. Kudos & Praise
  10. Support
  11. Working Together
  12. More than Just Work
  13. Lead by Example
  14. Clear Expectations
  15. Communicate, Over and Over Again
  16. Be Patient

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Welcome to the Conquer Local Podcast. My name is George Leith. It’s one of my favorite things to do, and that is the Master Sales Series episode, and this week, we’re gonna be talking about how to build a positive team culture. It’s something that, it’s exciting to look back and it’s actually humbling to look back. We’ve been building out the team structure that I’ve been responsible for, for growing and leading for the past nine years. I get asked a lot of questions around, “How did you build this culture?” and “What suggestions might you have as to how we could build a positive team culture?” So, we’re going to unpack the concept of building a positive team culture based upon the trial and error that I’ve been involved in over the last nine years and understand what to do and what maybe not to do and the things to avoid and the things to double down on. Keep in mind, I love this quote when it comes to culture, it comes to you from Henry Ford, one of the most famous entrepreneurs of all time, “Coming together is a beginning, staying together is progress, and working together is success.” We’re gonna learn all about building positive team culture in this week’s episode of the Conquer Local Podcast. 

Well, there really isn’t a day or a week that goes by that I don’t get some questions somewhere on, “You’ve got a pretty large sales organization and the company’s growing, how were you able to build this?” And then if someone were to actually come and see it live, then the questions are tenfold. And I’ve been thinking a lot about it, “How did we arrive here with this culture?” So, to give you a bit of context, I was the very first sales hire at Vendasta nine years ago. And one of the goals that CEO Brendan King had for me, was, “Okay, let’s figure out if we got something here, and how to make it repeatable, and then how do we grow it, and how do we build this organization?” So, I’ve been very fortunate to be involved with all of our leadership group as we’ve continued to build out a positive team culture, and a lot of credit has to go to our CEO and the guiding principles and leadership principles that he brought into the organization. So the sales department tries to align itself as much as possible with the other parts of the organization. And I think that that is one the key components, is don’t be too caught up in your idea because it’s never going to actually look the way you have it in your head when it’s all done, or when it’s rolling down the road and it’s starting to gain success, you have to have that. “It’s not quite exactly what I envisioned, but what’s the outcome that I’m trying to accomplish.” And one of the things that someone had said to me a number of years back is, “We’re all gonna work and we’re gonna make money hopefully and we’re gonna keep some of it, and maybe save some of it and have a retirement.” Wouldn’t it be great to go through that journey with people that you like and the people that you enjoy working with? And I think that that’s one of the benefits of a positive team culture. You don’t necessarily have to be best friends with everybody that you work with, but you have to be in an environment where there’s respect, where there’s a level of maybe even over-communication so that you ensure alignment, and that we really work together as a team. And you know teamwork makes the dream work, this all sorts of analogies and sayings and things that have come out of this, but it remains true that that team, if the culture is positive and it’s, even if the work is hard, and that’s one thing that I’ve noticed, there have been some days where the work is super hard and super challenging, and a positive culture will help carry you through those massive challenges where it might, the better word might be grind, or walking through the mud, like fresh mud. You know when you’re a kid and you thought it was pretty cool, and there was a rainstorm, you go walk through the mud, and then you got stuck and you had to get retrieved. That’s what I mean, when you have a really good culture, of course, it’s easy when things are great, but when you’re really slugging through the mud a good culture will help support that.

So, let’s talk about some of the benefits, and I’d love to bring some data. What are the benefits of a positive team culture? Well, studies have shown that 86% of employees and executives cite a lack of collaboration as one of the main reasons for workplace failure. So, if that’s the number of where failure comes from, and it’s quite a high number, then how do we build a positive team environment where we can build better performance higher team members, retention rates, increased profitability for the organization, and valuation of the company. There’s a lot of talk around mental health right now. So, how do we have positive mental health when we’re going through our day-to-day and we’re faced with challenges? And that employee morale is directly correlated to that. If we’ve got happy employees who enjoy their teammates, enjoy the environment, enjoy the tasks, enjoy the goals. So, those components are tied together, and we need to build that culture of success. And we’ve all seen the graphics. We could have the iceberg and it shows success at the top, and then underneath there’s all the things that lead to success, or maybe there’s that journey where you’ve got the success, and it’s like up into the right, not really like that. It’s the squiggly line where you might go backwards, you loop around five or six times, success is the journey. And it took me a long time in my career to really appreciate the struggle and the challenges that led to that success. Of course, you want to get to success or whatever that definition is, so you can have to have a celebration. So you look back and say, “Whoa, wow, we’re successful. I’m successful. Our mission was achieved.” But what I’ve found in my early years, I was so hell-bent on winning, I didn’t really appreciate the milestones along the road or even the moments where there were failures, and I learned. And when I started to slow that thing down, put it in slow motion, and take a good hard look at the last week, last month, last year, last decade, that was where I started to appreciate those moments. And now when I see one of those moments where, “Hey, we’re gonna look back this second and we’re gonna remember it.” I can actually have some gratitude for those moments even if it’s something super negative. Like complete and total failure, because there’s a lot of those. If anyone was really honest about their journey to success, there was a lot of failure along the road.

Keys to a Positive Team

So, what does success actually mean to your team members? Have you asked them that question? We all, as human beings are snowflakes, by the way, if you don’t recognize that, that’s the truth. We’re all a little different. And we have very common personality traits, and a lot of people have tried to map this, that the disc profile maps at the four basic personality traits. And guess what? It’s very rare that you have somebody that is a high one of those, it’s usually a combination of components. So, when we look at the individual, and the fact that we are different, and all of us are different, like snowflakes, then that means that our definition of success might be different. What I’ve found, and it took a long time to get here. If I could really connect with a team member and understand what was important to them, and then align that to the vision of the organization and to say, “We are aligned, our organization, our team and you, in trying to achieve what you’re trying to achieve.” We had a much better outcome. What does success look like to your organization? But then what does success look like to your individual contributors, and how do you align those two? And then what we need to do is constantly go back and measure that. What are the metrics? We’ve talked a lot on these broadcasts about leading and lagging measures, the four disciplines of execution, objectives, and key results from John Doerr Measure What Matters. This is about metrics, what’s the outcome? What does success look like? And then our actions in our day to day, leading us towards that destination. And being able to change that and move it and adapt. That really is the key in the business environment that we’re in today. One of our goals as leaders is to help everyone to see themselves in the future as better, smarter, stronger, more valued, and more confident. Think about that for a minute. If we went to work every day as leaders, and we took the people that are under our wing, that we’re supposed to be helping and leading, true servant leadership, what is Susan’s better? What is Susan smarter? What is Susan’s definition of being stronger? What is Susan’s definition of being more valued? And being more, and all of those lead to her being more confident! Now, the other thing that I think is really important and one of the core leadership principles that I’ve been raised in our organization around is leaders are right a lot. And what I mean by that is you have such a clarity of the vision of the organization or of your vision as a leader that you bring this unwavering confidence that you’re, you may not have all the answers, but you can damn sure come up with a solution for a problem. And that’s what people are looking for. That is going to lead you to this positive culture of success.


The other component that is absolutely critical is goals. Why are we doing what we’re doing today? Is it because that’s what we did yesterday? And there’s a lot of times we wake up, I have days like that. I wake up and go, “Okay, what am I doing today?” Oh, I guess I would do the same stuff I did yesterday, because that worked out okay. Like, am I really moving towards those goals? And that’s the hard work. The hard work is really understanding the goals and then focusing on them every day. Imagine if we could fire on all eight cylinders, that’s an engine by the way, that has eight cylinders. Some of them now don’t have eight anymore. They got like six, four or they’ve got a battery. But my point is, imagine if we were, but the truth is we don’t, we don’t fire on all eight cylinders. So, one of the things that we can do to make sure that we’ve got a better chance of getting to peak performance is do we really understand the company’s business goals? And then do our team members really understand? A stat that we found was amazingly only 7% of employees fully understand their company’s business goals. And you’re like, “Boy, what’s up with those employees.” But then I’m like, “Boy, what’s up with those companies and the leadership?” Our goal as leaders is to bring clarity to the vision and the goals of the organization. And what I’ve learned over the years is, it’s over-communication. When you are sick of telling the story, your audience is just starting to understand it. So, you should tell that story for another three or four months, because they’re just getting to the point when you’re sick of telling it so many times, to really grasping it, and then drill down into that individual’s goals and find a way to link the corporate goals to the individual goals, find out what matters to them, and show them how the company aligns to their own goals. And then you wanna set deadlines, and you wanna track progress. This is hard because people have been raised, and I don’t know where this came from, but I know that I have a lot of this too, that failure is a bad thing. And if I look back over it, it is in my greatest failures that I had the best learnings. And some of them were a straight-up kick in the ass, and others were a very slow, methodical pace where there were these, in little things that happen and they they were little failures, but when you add them all up, they were causing me not to have that level of success. So, we need to really drill down. We’ve used that word drill down a lot, but to get really granular into the individual goal setting, and then how that relates to the larger team goals is truly an art. 


Identifying values is really important in today’s culture. We have an entire workforce that has values, and they give us a lot of credit as a society, and as a species, we’re really getting good at instilling values into folks, that’s something that’s part of our DNA. So now we got to ask a question like, “What do our team members, what do they value?” And then how does that align with what the company values and do we even have company values? I bet you if we were to ask a random survey of companies, there’d be very few of them that have a very clearly outlined set of values so that the employees can map their internal values to that organization. And sometimes we learn something new. We learn something that has been missing. I remember years ago in sales, where I realized that a level of integrity was really important. It’s kind of funny to think about that, but back in the good old days of selling it was like, “I’m gonna say what I need to say to get the deal closed.” And I admit that I made that mistake. And now that doesn’t quite work out for you anymore. By the way, it didn’t really work out for you back then either. It was very short-lived. And then another value might be getting back to people on time. It’s such a small little thing. But if your customers believe that you are the one that gets back to them, it can be a competitive advantage. A lot of times, if we really embody those core values, it actually becomes competitive advantage for our organization.


I can’t talk enough about respect, I think it’s super undervalued when it comes to respect, and a lot of things map to this term of respect. So, let me give you an example, out on the sales floor, I’ve actually made this mistake, young sales person gets called a bad word by someone who’s having a bad day when they’re doing a cold call, and they just wanna hang up the phone and respond with the exact same negativity that the prospect gave them. But that isn’t having a level of respect, that isn’t having empathy. So, I know that’s a really far fetched thing where somebody said something really bad to you and hung up on you or something like that. But if we think about a level of respect across your organization. Our CEO Brendan has a great line, “I want to be hard on the issue and not on the individual”, and I think that that comes back to respect. There are certain things that are core values, there are certain things that go against our core values. So, rather than beat up on the individual, because maybe they’re having a bad day or maybe they haven’t been taught the right skill set, or maybe they haven’t been held to account, you actually go after the issue and not the individual. But we have to do it in a way that is respectful. And I think the other thing is, if we really have the right mindset of we’re trying to help that individual, even if it’s a really stinky thing that we have to do, because sometimes in leading groups it’s not all roses, if we come into every situation with a level of respect, I think we’ve got a better shot at empathy which is a really important component to understanding where the prospect is. So, as we think about this component of respect, I also wanna throw in another thing that we need to think about as leaders and that is responsibility. We need to be practicing the, see it, own it, solve it, and do it, and holding ourselves as responsible as we hold our teams for their actions. You really lead by example. And we want to make sure that we are owning the responsibility that has been given to us. Like we’ve been given the responsibility of leading these individuals. And I wanna tell you, there is an exciting moment coming for you if you really embody these components, because you’re going to look across your group, and you’re going to say, “Oh, I remember when Todd came into the organization.” And look at the way that that individual has grown. And if you’re really there and you’re trying to move them forward, and you’re giving them that support, it’s pretty cool to see them evolve over time.


We have to have this commitment. People can see an imposter coming a million miles away. So, you really have to be truly committed, and that means you got to put your time in. That means you need to be focused on the individual, and they can tell when you’re not. Like the best time to do multitasking is definitely not when you’re in a one-on-one with one of your team members. You wanna be focused on them, you wanna make sure your body language is that you care, that you’re listening, your demeanor is helpful, it’s respectful. And this will demonstrate that level of commitment that you need to have as a leader to build that positive team culture. I may not over the years have always got it right. And I may have failed in trying to find a solution, but I hope that the people that I’ve had the privilege of leading over the years will always say, “Yeah, he tried. Like he gave it a shot to really understand where I was coming from, and to help me in my growth.” I think that’s a win. It’s not, “Oh, you got it right 1000% of the time.” That’s never going to happen. But if you really, you’ve heard me before, talk about that give a crap meter. You have to have a high level of give a crap when it comes to the customers, and a definite high level of give a crap when it comes to your team members. Because they can see that imposter syndrome coming a mile away. Continuous development. How do we expect our team members to adopt continuous development, if we as leaders are not continuous developing our leadership style. And I think that’s another key component to developing a positive team culture, is that this thing’s never done. We’re gonna keep building it. We’re gonna keep improving it. We got a pretty good idea of what good looks like today, but that doesn’t mean that we’re done, that constant development, and the fact that we’re all in it together that helps you build that culture as well. You wanna lump on the praise and the kudos, and I can’t talk about this enough. I’ll tell you what I got used to when I was a younger performer out selling. I got really good at this, even though I’m not the most flexible person. I can actually reach around and pat myself on my own back. And I think I learned that when I was a business owner for the first time, it’s pretty lonely, and if you’ve done a good job, there probably isn’t somebody patting you on the back if you’re a solo-prenuer. Maybe you might be able to get your life partner to do it. Maybe you can teach your dog to do it, but you got to get good at it, of giving yourself some kudos. And then when you move to leadership, you gotta remember how great it felt to have the leader come to you and say, “You’ve done a great job.” And I am horrible at this. Ask anybody that’s on the teams. I’m trying to get better. Because it’s kind of like your kids or maybe your pets. They actually only want your time. Sometimes they want your wallet, but most of the time they just want your time. And that’s where you can show and give that praise. But that’s not enough. There’s something new that’s happened, and I’ve really noticed this in the last 10 years. We have a new generation of seller that wants the hard truth. Now, I don’t think that I wanted the hard truth when I was younger, that might’ve hurt my fragile ego. It might’ve hurt my feelings. But now I’m finding that true contributors, if you just pile on the praise, they think that you’re blowing smoke you know where. They’re actually saying, “Okay, I’m sure I’m not perfect. Where is the constructive feedback to help me grow?” And if you do not give that constructive feedback, you’re not going to get a positive culture. Because go back to my previous point of that continuous development. When you give somebody all sixes, or six and a half’s on a one out of 10 when you’re doing a performance evaluation, it’s the chicken way out. You didn’t really wanna have the hard conversation, like, “Oh, I’ve gotta sit down with Colleen and do her performance evaluation. She terrifies me. I’m just gonna give her sevens and we’ll just move on.” Now, that’s not doing anything for Colleen, because Colleen knows that she’s not a seven in everything. She’s got some threes in there, and she wants some help with the threes. So, part of our job is, if we’re going to do continuous development as part of our culture, and we’re going to do it ourselves, and we’re gonna push it into our teams as something they need to be involved in, I think we all realize that we’re not always sevens, eights or nines. There are the odd three in there that need improvement. And when we move to improve those components, let’s work together on it.

Working Together

Part of our job as leaders is to work together and you can do it in large group settings as well. I lead a lot of town halls, and a lot of all hands where you’ve got the entire organization, you’re not going to get that back and forth, but there are ways to do it, whether it’s a small group of four or five or one, or even up to 100s, where you can build this organization that works together, whether it’s small teams, individuals, or large groups. And then it has to be a little more than just work. This is an important component. And I think that one of the big downfalls of work from home, is when do you ever disconnect? Like we had a problem before COVID, and before work from home from disconnecting, thanks to the smartphone. And the fact that Wi-Fi is everywhere, technology is democratized. We are constantly connected, it’s gonna make our lives easier. Remember that ad? I don’t know if it did, we’re having a conversation before we came on microphone about, “Did Slack really help us, or did it just give us another place to go, where we gotta find stuff like email?” I don’t really, sorry, Slack. I don’t really think you solved any problems, you actually gave me a new problem. I got another bloody place to log in, to see collaboration and not just emails. So, what we really need to be working on here, is getting to this point of we’re a team, we’ve got work, we need to disconnect. And isn’t it nice to sometimes connect with your team members outside of work. And I don’t mean, meeting them on the weekends or something like that, but just having a talk about the human side of their lives. We had a couple of really good Slack channels. This is something I do like about Slack, but it just happened in the last couple of weeks. We got a thing called Petdasta, and we put pictures of our pets in there. Pretty cool. When we first put it in there, I was like, “I’ll never use this again.” But I’ve actually posted five or six pictures of my pets in there. And I probably wouldn’t have shared that with my team members, because I’m not inviting any of my team members over to my house. My pets are actually quite rude, but in a picture, they’re pretty cool. So my point is, is that we want to also have a little bit more than just work, doesn’t mean we need to be best friends, by the way, but it does mean that we need to understand the human side of each contributor on our teams.


And then that idea of leading by example, I wouldn’t ask someone to do something I wasn’t prepared to do myself, and I got to give to Bill. So Bill was my first employer, and he was a very patient individual, because he took on young people like me and taught me how to work. I thought I knew how to work, I mean I was farm boy. I hold weeds, I went out and clean corners, which is where you take a pitchfork and you move the grain, so that that combined just has to go around. It’s an old school thing, they don’t even do that anymore. Those were my first jobs, but I was working for my parents and they have to love you. Bill was my first employer that was paying me to do a job. And I remember him teaching me how to mop a floor. And I was mad at my mom, because I thought she had taught me how to mop a floor, but not the way Bill did it. And he actually did it himself and he showed me how to do it, and that’s how he taught me the skill of mopping the floor. And I learned such a valuable leadership skill at that, I was 13 years old, and I’ve always embraced that. I don’t want anybody to do anything I’m not prepared to do myself. Go fill that coffee thing for me, I need it at 10:00 AM on the sale, this happened recently, someone actually asked somebody to make sure that the coffee was filled at 10:00 AM, and I wanted to just go do that myself. Like I just don’t believe in that stuff. You wanna lead by example, you want to make sure the first boot on the field is your own. That is the leader that people wanna follow, is somebody that’s like don’t do as I do, do as I say, that’s 70s folks. And by the way, how do you even know how long it takes to do the job if you haven’t done it? They might say, “Well yeah, that job takes me two and a half hours. And then you do it, and it takes eight minutes.” And you’re like, “What are doing? There’s an efficiency thing there.” Or you watch the way that that job is being performed and you figure out a way to do it faster, or do it better or to make iterations on it. So leading by example, really important component.


We got to set clear expectations. Now, what does that mean? Can I see the expectation? Like clear means a lot of different things, but I guess my point is you always wanna be setting expectations because they change. So, we have an expectation for this project. Then we get into the project, and we recognize can take us longer than we thought, might cost more money than we thought, might need more resources than we thought. So, we come back to it and we say, “Hey, I wanna reset the expectations around this. We’ve done some analysis, and this is gonna take longer.” And this is part of that transparency that is so important in building that culture, where you want that positive team culture. I’ll tell you where negativity is going to creep in, if they’re wondering what’s going on, if they don’t have a clear message, if they don’t have clear expectations of the goal that they’re going after. So, a lot of our jobs as leaders is interpreting, we’re taking complex ideas, we’re making it simple, we’re giving it to our teams in bite-sized components so that we can accomplish the larger goal. That’s our job, take the big thing, put it down into bite-sized pieces and then help the team get there, support them and coach them. Communicate over and over and over and over, I can’t articulate that enough. You need it continuously communicate. And then finally, and I am at finally, doesn’t mean that I’m done, just means I’m powerfully close, you need to be patient. And this is a tough one, because I’m a doer. Thanks Bill. My first employer taught me to be a doer and then you one day may wake up and there are a 100 or 200 or 300 or 10,000 people that are counting on your concepts and your leadership. And in order to build that positive team culture we have to recognize that it doesn’t happen overnight and it doesn’t happen in a month, and it probably doesn’t even happen in a year. So, be patient, trust the process, constantly be evolving. 


We’ve had a lot of requests for this concept around how did you build this amazing team culture? And by the way, it’s not one individual, it’s an entire organization moving forward on a set of goals, with a set of values, and we’re gonna cover off the final components of this in a way that you guys can take it out and use it in a couple of moments. When we return with the conclusion of building a positive team culture on this edition of the Master Sales Series from the Conquer Local Podcast.


So let’s go back to the list of building a positive team culture. So number one, what does success mean? If we’re gonna build a culture of success, we need to define what success looks like, an overarching success for the organization or maybe the initiative, and then getting it down to the individual. We need to set those goals. We need to help unpack the goals so that people understand the leading and the lagging measures and what success looks like. We wanna relate it back to the values we have as an organization or as a team or as individuals. How do we get it to make an emotional connection? I think value is a lot about that. Like why do I care about this emotionally? How does it connect with my values? We want to go to work every day with a level of respect, a level respect for our coworkers, the folks that help us to build our solutions, whether that be vendors or providers, and then a level of respect for our customers. Take responsibility for every team member, every coach, every individual, take responsibility from that leadership standpoint. Make sure that everybody is committed, make sure that they believe, make sure that they’ve bought in. Keep working to gain that commitment. Continuous development across the entire organization, in ourselves as individuals, in ourselves as leaders, in our organization, and then with the people that we are entrusted with leading help with their continuous development. And then when they have wins, let’s give them some praise and some credit for the things that they won. Remember what it was like to have somebody come to you in your days on a team and say, “Boy, that was a great job, Brent, you did an amazing job today. Thanks for that, I appreciate the extra.” It gets important. It’s an important piece. Support, that’s what that praise and kudos means. It shows that you are supportive of your team, and it helps you to build a culture where you work together. And you get a shot at maybe making it a little bit more than just work. If we’re really gonna understand the values of the individual contributors on our team, we need to embrace that there’s more to life than nine to five or eight to four, or whatever your work might look like. What’s going on in your family. Like not a deep dive into the psychology of the individual, but understanding what’s important to them is really important to helping to connect. You wanna lead by example, and then set those clear expectations. I find leading by example is a great way to set clear expectations. This is the thing I’m asking you to do, here are the components. Let me take you through one of them to show you the way that I like to do it, and then you take it and adapt it for yourself. And then we’ll come back to it next week and see how it’s working out. That’s part of setting that clear expectations. And then the over-communication, I can’t stress this enough, all of those things that we were just talking about to build that positive culture are nothing if you don’t over-communicate them. What I’ve found is the moment that you’re sick of talking about it, is when it’s just starting to sink in. And then you’ve gotta be patient, and I’m not. So, this is hard, but I’ve learned that being patient, like a lot of days, you feel like you’re losing, and then you look back over the course of a period of time, and you’re like, “Wow, we won. Look at that.”, but you have to have that patience. You have to trust. You have to dig deep but really be committed to moving forward. So, I hope that this has been helpful. We’ve had a lot of people asking about the positive team culture that, I’m fortunate enough to be a part of inside our organization, and when I look back at it and unpack the things that’s been really a lot of people’s work to get us to this point, and a lot of learning, and a lot of consumption of other best practices out there. You’ve got the Patrick Lencioni’s, you’ve got the Grant Cardone’s, you’ve got the Gary Vaynerchuk’s, but I mean Gary today and not Gary back four or five years ago, because he’s a lot more empathetic today in his message. And I love seeing folks like that that have grown, but also I wanna give kudos to the Colleen’s and to the Brent’s and to the Todd’s and the Suzie’s that we’ve talked about today, because those people, while they’re not the actual individuals, their names have changed to protect their identities. They are individuals that I’ve come across throughout my career, that have benefited from the building and execution of a positive team culture.


Thanks for joining us for this episode of the Master Sales Training Series, as part of the Conquer Local Podcast. My name is George Leith. I’ll see when I see you.

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