Is Your MSP's Culture Killing Your Success?

[00:00:01] Welcome to the Powered Services Podcast, your go-to source for all things MSP. Each episode, we're diving deep into the world of MSPs, exploring cutting-edge solutions, strategies, and insights that empower you to supercharge your services. Join us as we connect with industry experts, thought leaders, and tech visionaries who are reshaping the managed services landscape.

[00:00:31] Plug in, power up, and prepare to elevate your MSP game to the next level. Now, here's your host, Dan Tomaszewski. Greetings, everybody, and welcome to another episode of the Powered Services Podcast. I'm excited to have you guys along.

[00:00:52] Today, we're going to dive into a topic that you don't hear all the time on podcast, on stage when you're at different events, and that's the culture of your business and the employees inside of your MSP. And what type of culture are you building? Is it a good one? What impact does it have on your business? And there is no better person to bring on and discuss that is Doug Diamond. Doug, how are you?

[00:01:22] Good, good. Excited to be here. Yeah, I'm super excited you're here. Doug comes to us. His business is business improvement. He's a senior business coach. He's the owner of that company. But I have personally watched you, Doug, work with a lot of MSPs. And also, you work with me. And you're taking the things that you're teaching MSPs. And I'm using it, too, with our team here on this side that's supporting MSPs. So it's a cool world that we're in.

[00:01:51] And I thought this was a great episode to do. And let's kick it off with telling our – giving us a little bit of background of how you became a business coach. Sure. Happy to go there. Let's just sort of set the stage that I was at one point an entrepreneur in my own right and at one point owned a software company, which grew. We did some really cool things. We had a really cool culture. I parted ways with that company in the year 2000.

[00:02:20] And at that point, I had some decisions about what I wanted to do with the rest of my life. And I actually fell into coaching somewhat accidentally. But people were kind of asking me to go to breakfast and lunch and dinner after I had sold my company. And at one point, somebody said, hey, can I pay you for this? And I said, what a great idea. Yes, you can pay me for this. And my coaching practice was born. And I've been coaching at this point now for almost 25 years. Wow. That's awesome.

[00:02:50] So, look, there's lots of business coaches out there, right? I see stuff on LinkedIn all the time. People are leveraging coaches and different things in different capacities. What makes you different in that capacity? So, I've been a traditional business coach, high ticket value, fly places two, three days with teams.

[00:03:13] But over the time that I've sort of the last 10, 15 years, I've actually invented or created a bit of a different model where I actually specialize in working with smaller teams like MSPs. And I've created an affordable model which leverages their time, my time differently than a typical coaching relationship. So, I'm able to provide high-quality coaching services at a much more affordable price than your traditional business coach.

[00:03:43] Oh, that's... Well, take that, right? Like, you know, you're trying. A lot of businesses don't invest into it because it is expensive, right? And I think sometimes that expense outweighs the reward, right, to the business. And people don't get to realize that. So, that's a cool motto, slogan and marketing tip right there, right? I like that. Good. All right. So, let's talk about culture and engagement, though. Because, you know, I had an MSP.

[00:04:10] And, you know, I was talking to you before this and even throughout my coaching with you. We never did some of these things at my MSP. But I see the importance of it now and, like, what it does and what it could have done for me. And I also see what it's doing for a lot of the members today. But first question I have for you is, look, we hear a lot about culture, engagement, frequently as is important in a small business. But it's really hard to define.

[00:04:37] You know, so what specifically do they mean to you? Yeah. So, that's... It's a really interesting question. We hear the term culture. I'll define culture as almost at the high level how we treat each other. That's the simplest definition. But it kind of... You boil into it a little bit and you get the kind of the values and the attitudes and the beliefs and the practices that are part of how we interact as a team that influence how things get done in the organization.

[00:05:06] And all those things are part of our culture. So, it's like our collective identity. Or some people will call it like the invisible glue that kind of holds us together. So, those are the things that I think are useful in defining culture. People often see culture in like the core values of the business or the mission statement or the purpose statement of the business. They'll see culture in reward and recognition systems and celebrations.

[00:05:33] You'll see culture in terms of how the company approaches employee performance and reviews and whatnot. So, all of those things contribute to it. But it's elusive to define because it's not any one of those things. It's the collective sort of work of all of that. Engagement to go beyond that. So, engagement is beyond that.

[00:05:56] Engagement is the ability for each individual member of the team to put in that what I'll call discretionary effort that they either are pushing out there or withholding from the company. They're either working hard when no one's watching or they're not. And that engagement is another indication of the people systems being healthy at the company. Well, that's awesome.

[00:06:25] I mean, so, let's take it a step further then. You know, everyone that's listening to this podcast is an MSP. So, why do you believe that the culture and engagement are really particularly important for this MSP industry? Yeah. I've worked with, at this point, hundreds of MSPs over the last 20 years. And most of them would say that they're in the technology business.

[00:06:51] And what I've come to conclude is that while they are in the technology business, they're really in the people business. Nothing happens at an MSP without people interacting with each other and with the clients and with the vendors. Like, it's a people business.

[00:07:08] And if we've got a team that's working together, that's collaborative, that is willing to, like, set different processes in play and everybody follows the process because they want to be part of the team, we end up with a really good result. Because we end up doing things systematically and well and in a way that we get consistent results.

[00:07:31] Compared and contrast to teams where people are on their own islands, everyone's thinking like an individual, there's no collaboration between departments. That is not a good way to run an MSP. And leadership and management has got to be good at getting people together and getting them organized and collaborated and working well together in order to get the outcome that we want for our clients and for ourselves. So, can we get into a few things?

[00:08:00] I'd like to dive into a couple of these areas. So, what are some signs that at my MSP that I have a healthy culture? I think the most important is a feeling of winning that you get when, like, you've got things working really well. You're winning the deals that you want to win and you're onboarding really well. The companies that you're onboarding are coming in and being successful.

[00:08:29] So, there's this overall spirit of winning. But there's also this energy. There's an enthusiasm. There's a level of collaboration. There's an element of fun. Like, when we go out together, we have a good time. But it's not just when we work together. We have fun when we're at the office just doing our work. There's an element of fun to it. I think all of those things, it's respect that we show to each other. It's like all of those things woven together, I think, make for a really good definition of good culture.

[00:08:59] So, let's go to the opposite now because you always got to play devil's advocate, right? And we got to say, what are some signs that the culture at my MSP might need to improve? And maybe it's just not smacked me in the face yet. Yep. So, look. Every – I've seen a bunch. Companies where they're just not on the same page. They're good-meaning people, but there's silos going on.

[00:09:28] Like, each department isn't cooperating with the other. There's lone wolf situations going on where people are out at client locations doing what they think is right without communicating and collaborating with the rest of the team. There's sometimes unhealthy conflict that's going on. People are getting angry at each other. They're doing inappropriate conflict. So, name-calling and all sorts of things. I've seen some crazy things.

[00:09:56] Disengaged team members, people that are not trying very hard, people that are doing the bare minimum. There's low energy. And there's often just no team spirit going on. I would say all of those are hallmarks of low culture environments. So, how can MSPs balance the demands of a high-pressure work environment with the need to, you know, maintain a supportive and engaging culture, right? Because it's a demanding industry.

[00:10:25] And, you know, we'd love to hear some tips that we can put into place to help us go through that. Yeah, yeah, for sure. The thing I think that you need to do is to just make culture and engagement a priority. It's something that we talk about. It's something that comes up in team meetings. It's not something that we have to focus on for weeks and weeks and weeks. We don't have time to do that.

[00:10:51] But if we spend a little bit of time at our weekly meeting, if we spend a little time at our either monthly or quarterly company meetings, if we spend time talking about how we treat each other, if we don't have core values, we invest some time in developing core values. And then we don't just develop the core values, but we actually take the time to roll them out and make them come alive in the organization. So, it's attention to detail. It's not absolute focus on it all the time.

[00:11:19] But consistency, quarter by quarter, year by year, you'll keep making improvements in your culture. And it will be enough that you'll feel like the high demands of all the other things that you're doing are being balanced by a reasonably high quality culture. And you do something that I think is really cool. You have a culture survey that you do. How many times a year do you do it?

[00:11:48] So, the culture survey is done twice per year. Q1, we do what we call the full survey. And I can talk a little bit about that because that's active now. That takes people a little bit more than 15 minutes on average to complete. And let me just go to the – so, in Q3, we do something we call the snapshot survey. That takes people usually less than 10 minutes to complete. You're trying to track the progress.

[00:12:16] You're trying to see where you've come from the beginning of the year. Yeah. Yeah. And my belief about the survey is this. It's not something that teams have to do twice a year. It's like it's – I think if teams do one or the other at least once a year, just get a check-in on their culture and just do it consistently over time. And like I said earlier, it's just consistency and attention on the topic of culture. Keep making small tweaks every quarter.

[00:12:46] Your culture will gradually improve over time. So, I mean, I'd like to ask. I mean, you mentioned the surveys and what they are. But why did you create this culture and engagement survey for the MSP industry? So, partly it was because I was looking for feedback from my clients on how their culture and engagement was doing.

[00:13:11] And I couldn't find an affordable tool that I could recommend to my clients. And so, I just decided I was going to invent one. And so, I actually started 10 years ago. Like this survey has been going for 10 years. And, you know, in the early days, perhaps the survey wasn't smooth. I learned a lot quarter by, you know, doing it twice a year, I learned. I got great feedback from users over time.

[00:13:37] But I did it really because I wasn't able to find any available tool that I could make available to them. And so, by inventing and creating my own, I was able to offer it for free, which is what I've been doing for 10 years. And there's a whole thing about my free survey. So, like people make fun of me. But the God's honest truth is that I offer it for free because I want as many teams as possible to take the survey.

[00:14:06] Because I want to give my clients the broadest possible comparisons. And one of the things that the survey does is it not only will share with you what your team is thinking in terms of culture and engagement, but it will compare your answers against similar sized MSPs. So, it's giving you feedback about your team and how your team's answers compare to others. And I want that comparison to be as valid as possible.

[00:14:31] So, the more teams that I have included in the survey results, the better the comparison data becomes. So, tell us a little bit about the survey. What types of questions are going to be on there? Like what can I expect for people to be answering? And like let's say like how long does it take and what reports do you share back then? Yep, yep. So, first of all, I want to say very loud and clear, the survey itself is anonymous. And it's anonymous for several good reasons.

[00:15:01] One, I don't want anyone answering the survey being fearful that their job is going to become in jeopardy because they're sharing their answers freely. So, I want them to be completely feel safe to give us the unvarnished truth. The way that I do the survey is I take everybody's from one team's responses.

[00:15:25] I aggregate the responses together so that you can't discern how anybody individually answered any of the questions. The questions themselves are mostly a series of statements that they can agree or disagree with. So, there's a scale. It goes from a strongly agree down to a strongly disagree. So, you've got moderately disagree, slightly disagree, slightly agree, moderately agree, strongly agree.

[00:15:54] And I assign numerical values to those. So, if everybody on the team said strongly agree, that would be 100 points. And if everybody on the team said strongly disagree, that would be zero points. So, the survey is mostly on a zero to 100 scale for each of the statements on the survey. You know, the survey takes typically, you know, as I said, a little bit more than 15 minutes.

[00:16:19] There's a few questions on both the Q1 and Q3 surveys where they're allowed to type in comments. So, I always ask some just opinion questions. But most of the survey is just agreeing and disagreeing the statements that are set on the survey. So, the reporting is mostly showing how did you do on the statements.

[00:16:40] And there's another report that will also show the comments that people made aggregated by statement and for the extra questions that I put in there. So, it's a little bit of both. And I heard you say that it's active now. So, I want to go and kind of do like a two-part question on this one. So, when does the survey run? Like, how long is this open for?

[00:17:07] And if I go and have my staff, like if we're going to, I'm going to walk through with people as they can take this here at the end. We'll make sure people understand that. But let's say we go in and we participate in this. When does it start? When does it end? And when would I get my results for me to look at? Yep. The survey itself is right now in what we call the sign-up stage. So, it's not open yet.

[00:17:30] But the people who want to do the survey are able to sign up from now until the 10th of February. So, there's a link that you can click. You just have to fill in some information about your company. You know, who's the primary contact? How many people would we expect to take the survey? So, it's just some basic information about the team. And then we basically have all the information we need. The survey itself is going to open on the 10th of February.

[00:17:59] So, we're going to send out links to the various teams that have chosen to sign up. And it's very important. They actually send the link to the survey to their team members. We don't collect email addresses. We don't actually reach out directly to any team member specifically. We work with the survey administrator, whoever that person is on each team. We send the links to them. They email their team.

[00:18:26] And then periodically while the survey is open, which is three weeks. So, from the 10th until about the 28th of February, the survey will be open. During that time, we'll send regular emails saying this is how many people on your team have already completed the survey. Here's how many, based on the number of people you said we would get. This is how many still need to do it. So, we're communicating the logistics sort of during the course of the time that the survey is open.

[00:18:52] The reporting itself is tabulated after the survey closes on the 28th. And the reports will be sent out by March 10th. So, the reporting will be out sort of early, early, early part of March. No, that's great. So, now I'm an MSP. I go through. I do this culture survey. I've never done one before, right? Like, you know, I don't even know. I just listened to this. I heard you. And I'm like, yeah, it sounds. I'd love to just see where my business is at.

[00:19:21] So, how do MSPs typically use the results of your survey? And, like, you know, what's the common framework then or the common things of how do they improve? Like, how do I improve once I get the results? Yep. So, I'd say the best scenario is a team who takes it for the first time. They're going to get reporting. And it's going to say what it says. I often sort of encourage people to take a deep breath the first time they read the reports.

[00:19:49] Because sometimes the feedback that we get from our team isn't necessarily what we want to hear, right? But the first time you do it, it's like you are where you are. And I want you to just kind of lean in to say, okay, some things are good. There's always good stuff on the survey. And there's some things need improvement. And so, now we know a little bit more factually what we need to work on. I always recommend sort of the leadership team looking over the survey results first and making some decisions.

[00:20:18] Like, what do we want to invest time to improve? And the leadership team, therefore, needs to take some time and put in some energy to help things get better from a culture standpoint. But I often like to say that culture isn't just a top-down thing. Like, the leadership team can't dictate what the culture is. The culture really is a collaboration between all layers of the company.

[00:20:44] So, it's also a good idea to put together a cross-departmental, cross-level team that will be what I'll call the culture team. This team, hopefully, is invested in helping to make improvements in the company quarter by quarter. And the best companies with the culture survey, the ones that do the best, are the ones that regularly do the survey at least once a year. So, every year they're getting a check-in on the survey.

[00:21:11] They're getting additional feedback from their team. They see what's improved since the last survey. They see maybe a couple things have gone down. And this culture team and the leadership team are both investing time and energy, making sure that they're taking action where action needs to be taken. I've seen teams go from not very good results to really good results over a couple of survey cycles. And they just keep getting better.

[00:21:38] If you take it seriously and you keep doing it over time, it works really well. So, I'm going to ask one more question. Okay. Because I want to be respectful of your time. But, like, what are some common challenges MSPs face when they try to improve their company culture, right? Because it's not like – I mean, I heard you say, like, it is what it is. Your results are where they're at. And now we've got to work to go forward.

[00:22:02] But even trying to just go and improve the culture of that you thought it was here, but it's really here, there's got to be hurdles. There's got to be challenges. Like, what do you typically see MSPs face when they try to improve that? Yep. So, let me give you a little bit of a three-part answer.

[00:22:20] For a smaller MSP, let's say less than 10 people, where you can get everybody into one room, it's easy in that scenario to just go over the results of the culture survey together and just have a conversation about it, right? So, we're not so big when we're a 10- or fewer-person MSP. We're not so big that we just can't get together and let's just talk this out. Let's talk about the things where we're good. Let's talk about the things where we're not so good.

[00:22:46] And let's challenge each other to figure out what specific things we're going to do to get better. As you start getting into larger-sized MSPs, 20 people, 30 people, 40 people, it gets a little harder to communicate the results of the survey in one sitting. And sometimes then the culture team needs to do a little bit of work and actually working with different departments, sharing the results in smaller group settings.

[00:23:13] I personally believe that in a room full of 30, 40 people, it's hard to have a conversation about the topic of culture because there's just so many people in the room. And I think it's better to have conversations when you've broken the groups down into 10 or fewer people and can talk there. But then you've got to coordinate between departments.

[00:23:36] So that's some of the hurdles is taking the results, making people aware of the results, getting their feedback on what they think is important in terms of actions that we're going to take, and then following up on those actions. Like if you're doing any kind of normal quarterly planning, it's not unlike sort of a quarterly priority. Every quarter there might need to be something around the topic of culture.

[00:24:00] And following up and staying focused, it's all part of the discipline of making improvements to the company. So, Doug, last, I mean, I heard you talk about this with all of our listeners, is this is free. This is absolutely free. We're not on this podcast selling anything. What we're trying to say is, is like, take a look at your company's culture. Look at what's going on and start to go. Now, if you get the results back and you're like, wow, like, you know, what's going on?

[00:24:30] I mean, Doug obviously is a business coach and can work with you and put those plans in place. He can also look at, you know, just the business with you and help you strategize and go through that. So two really important things that you need to be looking at is the culture one. But also, I would argue like the business planning, the process behind it, the priorities you have set. And for a lot of us in MSPs, we say we don't have time. I hear that all the time when I get on the phone with people as, man, I wish I had time to do that.

[00:24:58] I don't I don't think it matters what industry you're in. I think everyone's saying the same thing there, which is why it's super important that the time that you are working, you're putting it to the right priorities. And I think that's where having a coach to help you kind of see through a little bit different lens, challenge you in the right ways, but also help you implement some of the right strategies. Not only can you hit your priorities, but you can also change your culture along the way. So I highly recommend people do this.

[00:25:26] We're going to put the link to the to sign up in the podcast notes. So if you're listening to this on Apple, Spotify, go to the show notes, the link to register for the survey will be there. If you're on LinkedIn, it'll be on the LinkedIn post. So just click on it and you can engage and log in through that way as well. But Doug, like, you know, how do I get to this link? I mean, if I'm listening and can you want to tell it?

[00:25:54] Can I go to your website or where do I go? You can actually, I can just say out loud. So my website, bizimprovement.com, B-I-Z and the word improvement.com forward slash culture. If you go there, you will see not only a link to sign up for the survey, but you'll see information about the survey. So it'll show you some sample reports. It'll give you some more background details about what you'll be getting.

[00:26:19] And of course, my email address, ddiamond at bizimprovement.com. I'm happy to have anybody just send me an email if they have questions or concerns. I'm happy to respond to anyone and hopefully get them comfortable in giving this a try. Doug, I really appreciate you coming back, coming on. I want to bring you back is what I was saying. I want to bring you back on and talk through some of those things, right? And like hear what some of the common themes that you were hearing and seeing

[00:26:48] and how we can help people along and really in 2025, help people with their business and helping people improve the culture, which ultimately will help them with their business and really seeing, you know, the growth that they're looking for. So I just want to say thank you for taking the time and coming on with us today. My sincere pleasure, Dan. Always good to work with you. Nice working with you. And thanks, everybody, for listening to another episode of the Powered Services Podcast.

[00:27:16] Until next time, everyone, make it a great day. And that's a wrap for today's episode of the Powered Services Podcast with Dan Tomaszewski. We hope you're leaving with your mind buzzing with new ideas and strategies to revolutionize your MSP offerings. Don't forget to subscribe for more insights. And join us next time as we continue to decode the complexities of managed services.

[00:27:45] Until then, keep powering through. And remember, the future of MSP is bright and fully charged. Thank you for listening and stay connected.