Do you know Jesse Smith? Jesse is our chief operations officer. Throughout his 16-year career at Smart Dolphins he has witnessed a dramatic evolution in how we use and embrace technology in the workplace.

In this episode, Jesse unpacks the influence of Microsoft in that evolution and the significance of tools like Microsoft Teams in coalescing the Microsoft experience. He encourages business leaders with legacy technology to seriously get a handle on what IT improvements need to be made. This is important not simply because of hidden IT risk but because we live in a world where people are demanding the tools to work from anywhere, at any time and on any device.

From this podcast, we hope you will get a stronger sense of the role technology plays in building a vibrant and productive workplace culture.

Jesse Smith Smart Dolphins

People think that because they have cloud solutions they’re good but companies open themselves up to all sorts of other challengesWe’ve always been big on helping companies see the things that they don’t see and uncovering the hidden risk in their organization. There’s just more of that than there’s ever been. I think if anything, it’s just getting more complex. There’s such an ocean of choice, and a lot of what gets missed these days is just thinking about those hidden factors.

Jesse Smith

COO, Smart Dolphins IT

Island Thrive Podcast
Island Thrive
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Paul: And welcome to Island Thrive. My name is Paul Holmes and co-host today, Dave Monahan, President of Smart Dolphins. How are you today, Dave? 

 

Dave: I’m excellent. Thank you Paul. How are you? 

 

Paul: I’m doing good. 

 

Paul: And excited to have Jesse Smith, the COO of Smart Dolphins. Jesse has been with Smart Dolphins now for 16 years, in various roles, but generally speaking, one of the guys running the machine behind the scenes and…Yeah, Jesse why don’t you introduce yourself to the audience, tell them a little bit about what you’ve been doing and a little bit about how your role has changed. 

 

Jesse: Alright, hey guys. Happy to be on the Island Thrive podcast, I was helping you to ask me how I was doing so I could tell you that I was thriving. 

 

Dave: Yes. 

 

Jesse: I didn’t get that opportunity, so 

 

Paul: How are you doing? 

 

Jesse: I’m thriving Paul. 

 

Jesse: How my role has changed? Well, it’s been like you said a long time here I’ve here for… When I started at Some Dolphins, we were a much smaller company. I think there was five or six of us, and we fixed problems for the most part, and over time, we transitioned to much different company. We are called a managed service provider. So companies outsource their IT responsibility to us, and I work in that team and I lead the managed services part of Smart Dolphins. 

 

Paul: Awesome, and obviously, you’ve seen a lot of changes over that transition from that to what we sort of call the break fix model of it, to the managed service model. Lots of companies have embraced that, lots of companies still have not. Where do you see that service delivery model going in the future as we’re embracing more cloud and the state of the world changing with technology and the way security is right now? 

 

Jesse: Well, I think in a lot of ways, what we do is becoming even more important than it has in the past, because everything looks easier today than it used to look. It used to be that you hired a nerd in the closet to take care of things and most IT work happened behind the scenes. We would come in on the weekend, replace your server, move your files, change everything around and only sign that anything had happened at all was when we made a mistake. We still think it was the most thankless jobs you could do because it was almost completely invisible to companies, if it was done well. And what we’re seeing today is a much different approach to the way technology is managed, that you see that in the solutions that Microsoft puts out as an example with Teams and other platforms where they’re very much set up so that the users and the leaders within organizations take a much more active role in how those things runSo it’s not uncommon for a manager of a team to create their own team in Microsoft Teams and add their own people and move their own files. 

 

Paul: Right.  

 

Jesse: So our role, I think, is shifting towards making sure that we are providing coaching and help as opposed to just doing the work for people and getting leadership of organizations to be an active part of the IT, where they weren’t before. And on a similar role with users, or I should say people, they need to take a more active role as well, in order to work securely, you’re often going to be required to manage some certain aspects of security of how you work or undergo training or put a multi-factor token on your phone or those types of things, that some people just really weren’t ready to do before they would just write their password on a post-it note, shove it under the keyboard, and that was the most that they had to do so. 

 

So our role is shifting in that way, and in other ways too, there’s a lot of invisible risk and things to consider too when you’re working in the more modern way. People think that they’ve got cloud solutions, so they’re good and it’s really easy, but companies open themselves up to all sorts of other challengesWe’ve always been big on helping companies see the things that they don’t see or uncovering the hidden risk in their organization. I feel like there’s just more of that than there’s ever been before it.  

 

Paul: But it’s weird though, right? Because the amount of technology that people need today compared to 15 years ago, we have our smart phones and we have our computers, and we’re constantly staring at a screen all day long, and almost every job in almost every industry, right? And our dependency on that technology is so much more important now, even than it was a decade or even five years ago, and so… Is it strange that in some ways people think because things are moving to the cloud and stuff that somehow IT is not as critical as it was a decade or five years ago. Do you get that sense? You get some people who I really get it, who really understand it, but you see a lot of people where they just think, Oh well, I’ll just fire up a bunch of cloud services and that’s it, we’re good to go. 

 

Jesse: I think people think it’s more critical than ever, probably wouldn’t use that word, but I also think the ease of doing things yourself creates a bit of an invisible safety blanket that we don’t really need to worry about IT in the same way we did before…we can buy these things and set them up ourselves.” 

 

I think if anything, it’s just getting more complex. There’s such an ocean of choice, and I think a lot of what gets missed these days is just thinking about those hidden factors. Maybe I’ll highlight an easy example. If you consider a five-person company who starts up a year ago, they’ve grown to five people, and over time, they’ve added QuickBooks Online and Slack, Microsoft 365, a couple other cloud applications along the way, maybe Dropbox. Those five people are going to have at least 25 usernames and passwords scattered around amongst the Internet with data just all over the place, and that’s just the applications that you know about, because most of us will happily install other cloud applications as we go, when we need them and sign up new accounts. So that’s one really simple example of just how quickly and how exponentially these things they think some grow, right, few extrapolate that to even a 20 user office, we are talking hundreds. And you can ask people to use secure credentials when they do these things, you could even give them a password manager like LastPass and teach them to have secure passwords, but there’s nothing that actually allows you to enforce it or manage it in any wayAnd then apply to data and where your data gets stored, if you’ve got Company files and Dave’s got Dropbox, and Paul’s using his One Drive account, and I’m using something else, and we’ve got company information, that company information can very, very quickly start to just leak all over the place, and it’s not protected by anything other than those potentially on managed accounts. So yeah, I think the complexity is he just… Just one little piece of it, and I think it just grows and grows and you can… You can just imagine he… They’re solutions to all these things too, but they’re not well understoodI think they’re also relatively new to the world, Office 365, as you mentioned, came out and it’s great, fantastic platform, we’ve all dived into it very quickly, but then… What do you actually do if you wanna protect against all the things I just talked about, there are, again, there are ways to do it, but they’re invisible and the solutions are invisible, but the problems are usually invisible and then the solutions are well understood, so you do have this humongous problem that a lot of companies are just growing and adding stuff and losing the complexity battle. 

 

Dave: We’re kind of describing the issue, the problem, and yeah, every business so different, we’ve talked to many and it’s hard to prescribe, the paint by numbers or the five steps to great IT. But I guess, is there some fundamental building blocks that we could prescribe? Generally, maybe people are at different points in the lifecycle of all this stuff, is there a starting point for maybe somebody that’s at the bottom end of that? 

 

Jesse: Yes, there is and unfortunately everybody’s in a different place, so that’s good and bad, and it’s good, in that you can jump in and you don’t have to get necessarily bogged down in all the complexity before you get going because the systems need to move. But it is good to be aware of maybe the things that you haven’t cleaned up as you’ve gone. I think is where technology planning has such a place because there’s likely dozens of things that you should ideally do in a perfect world, and some of those things should be done first. And some of those things are going to be much more critical than others. So you’ve got this gigantic elephant that you need to feed over the next three to five years, and your plan is going to help you tackle what’s going to happen in the first quarter. 

 

I would say to maybe just simplify what I’m talking about down to the Office 365, Microsoft 365 piece. And note that those are two different products. Office 365 is what most businesses have today, it gives you exchange, email online, Microsoft Teams, OneDrive and a bunch of other stuff, and what most companies do is they start by dipping their toe into that world when they move their on-premise email exchange server into Microsoft, or their current webmail solution into Microsoft, so they start with that in place, and then once they’re there, they’ve got all these other things available to them, and then that’s when the potential sprawl can happen. I do think that’s a good first step, and I don’t think companies need to get too bent out of shape with all the different pieces of complexity related to that. 

 

The thing that’s interesting about Microsoft 365 is when you create a new Microsoft 365 account with Microsoft, you get not just your email platform, but there’s a whole directory that gets created in the cloud called Microsoft Azure active directory, where all of your usernames and passwords and information is stored. And that service is used to authenticate all the other Microsoft services. So if you make that account super duper secure, not just with a great password, but you attach multi-factor to it, then you’ve got a really secure account in the Cloud that can be used to secure all those Microsoft services. So multi-factor is a really good first step, just sort of focusing on that identity, making sure that your identities in the cloud are secure really well with the right technology in place, and then beyond that, you can actually start to tie in other applications to your Microsoft account. So Dropbox or Slack or other Cloud applications, you can take those logins and use a feature called single sign on to hook them to your Microsoft Azure account, and now you’re starting to consolidate all those usernames and passwords into a single very secure login that you have. You’re sort of addressing that problem I spoke to you earlier. So as far as where to start I think identity and moving to Exchange Online and then focusing on securing your identities is a really good place to start. 

 

Dave: Some might not know what multi-factor is. Can you maybe jusquickly describe it? 

 

Jesse: Yes, I was actually thinking that as I said it. So multi-factor means you have more than one method required to authenticate yourself. So multifactor could be your password, a token that you have in your hand that gives you some kind of number that you have to press, or it could be your fingerprint. So basically requiring those two things in order to authenticate right. So what that does is if somebody manages to get access to your account somehow unless they have two of those things, which is usually almost impossible if they’re not physically you…Then they’re not going to be able to log in. 

 

Paul: This is going to change over time, but the typical secondary to a password is you get a notification on your phone, or you have an app on your phone and you have to put in a six-digit number or seven-digit numbers sometimes. Most people are familiar with that from logging into one website or another. But the ability to have a physical key that’s digitally plugged into the computer, or the ability to scan your retina or fingerprint or whatever… All of those other things are possibilities of authenticating who you are. And I think in the security universe, if you’re not the CEO of some big Fortune 500 company something, the likelihood that people are going try to hack your phone to get into your Microsoft email is pretty low, but not outside the realm of possibility of course.  

 

Jesse: It’s funny, there’s been a few times I’ve actually had random multi-factor prompts pop up on my phone unexpectedly and I wondered, okay, did somebody get my password because they are trying to login.” And then I’ve ended up realizing where it came from because my Outlook was acting up or something like that. Yes, it’s also a good way of knowing when somebody’s stolen your credentials is if your multifactor goes off. 

 

Paul: Suddenly it’s like I better go change my password.” But this doesn’t prevent the social engineering part, right. So if somebody phones you up and pretends to be your IT company or pretends to be Microsoft, and they say, Oh hi, I’m calling to help you fix your account, and can you tell me your password so I can login and then… Oh, it’s indicating that I need a six digit number. Can you check your phone and give me the six digit number.” It doesn’t stop that social engineering part, which of course (and for anybody who’s listening, by the way, Microsoft doesn’t just phone you randomly and ask for you for your password, that’s not a thing that happens, and neither should your IT company. We certainly don’t). But it’s really shifted the onus of security. And it’s funny because you talked earlier about…in the early 2000s, we talked about the firefighters and the superheroes of IT, and I remember I used to sit in business meetings and I’d hear about the IT guy that was there and how he rescued somebody’s server from total collapse, they almost lost all their data and blah, blah, blah, and everyone clapped and oh, what a great hero he is.” And then most of the rest of us, including me sitting in the room going like, why did they not just stop that from happening in the first place?  

 

Jesse: Right, right.  

 

Paul: Managed services really came in to address that problem like, “hey, let’s not get to the point of almost total collapse with losing data and that sort of thing.” But it made IT less exciting. People don’t realize all the stuff that goes on behind the scenes, just prevent that sort of stuff. But we’ve gone from that, that sort of superhero persona to now putting a lot of onus back on the end users not to be social engineered, not to click on the links that come in through their email, and not to pick up a USB drive and plug it into the computer and infect their network with a virus and all those things. What are your thoughts around that because that’s really I think the weakest link in all of this is it not? 

 

Jesse: It is. There is an old saying that the users are the weakest link but I think there’s a lot that can be done today to make that a lot simpler for people. I think, like I said, focusing on some really high value security best practices like multi-factor can do a ton. I think most people are not gullible enough to give their Microsoft password account over the phone, although it does happen. What we tend to see a little more of is just plain old phishing attacks where somebody goes on your LinkedIn profile, sees who your boss is and then uses the bosses name to send you an email and asks you to buy gift cards or something. Those types of things are pretty common. You can also put things in place to make life easier for people with some of the security practices that you need. 

 

I think Ty spoke to being able to restrict access from outside parties based on what country they’re coming from, which can help with things like phishing. But you can also use some of those same features to lighten the security requirements on users who are in the right office or in the right country. So Dave doesn’t need his multi-factor code when he’s in the office, the service sort of detects that he’s in the safe location, it’s 99.9% Dave. And so his password is just going to be fine. Training is still absolutely a critical piece of what’s needed. People need, I think, to be at least security cautious. People don’t need to necessarily go through hours and hours of security training, but there’s a lot of people, I think that would still fall for some of those more basic attacks, so  

 

Dave: You talked earlier about many companies getting into the Office 365 or email online, and you mentioned many falling into the sprawl and I’m wondering, if you could describe in a little more detail what a sprawl might look like for some of the companies. Just a side note too I think the security conversation is great, but it’s almost like we need a little podcast on just that, so I’m trying to move us on from that. So sprawl what does that look like? 

 

Jesse: The sprawl well, a lot of it, I think from a general place of cloud accounts, what I spoke to you earlier, that’s one way I would see sprawl happening, and then I think within your Microsoft tenant, sprawl could also happen through something like Teams. Outofthebox, Teams is great. Teams is my favorite product that’s been put out by Microsoft ever and set up in the right way, it’s super, just super powerful tool that you can grow with and scale with, you can move, not just your email conversations out of Outlook into teams but you can also take a company data and you can move it into Teams. But that some thought, I think should be put to how that’s structured. So if you were going to start using Teams tomorrow, for example, because you really wanted to get video conference going, I would be suggesting that people lock down the ability to create teams to just a few parties and keep it really simple. Because what happens when you create a team is it’s basically a group of people, and there’s going to be a SharePoint site, which is a Microsoft site for storing files attached to the team in the background, that team is going get its own files tab, and you might have a whole department and who starts moving their information into the Team’s team. So being thoughtful about that and making sure you have a strategy in place for data specifically I think is important before you get too far along with it. The other thing to consider, going back to security because I think it does tie to the sprawl is outofthebox, if you’ve got a Microsoft 365 account, you can log into that from any computer, you can install the Office apps on any computer. So you could put it on your personal computer, you could 

 

Paul: Your phone. 

 

Jesse: Your phone. 

 

Paul: Your tablet. 

 

Jesse: Yeah, so if you start moving company information in there without a strategy in place for managing all that, it’s very easy for you to end up with files of scattered all over the place and sitting on computers that you have no control over. Again, I mentioned identity earlier as an important part of the piece, but the other piece I think that as probably gets neglected more often than not, is actually managing the devices that things are accessed on. Syou should be thinking about where the data is going to land and you can put some restrictions in place to ensure that people can’t. As an example, you can put a restriction in place that says “if you’re going access your Microsoft Apps on a unmanaged computer, you could only use the web browser and you’re not able to download. You can configure those types of settings with the Microsoft licensing (if you have the right licensing). So that people can still do the work that they need to do, but there’s some restrictions in place, and then when they’re on their actual work computer, they can do the full-blown access to things. 

 

Paul: It’s so funny because we’re all IT guys here, so we love to talk about this stuff and we love to talk about the nitty gritty of the security aspects. And it’s important stuff. And it’s important that gets done well. I just kind of chuckled though, when you mentioned that Teams was the product, the Microsoft product you’re most excited about because I feel the same way. I actually get very excited about it, and then I laugh because I thought… And I’m going to ask you this question Jesse unscripted here. Before Microsoft Teams what was your favorite Microsoft product that you got excited about? 

 

Jesse: Oh man. 

 

Paul: Like honestly? 

 

Dave: Something much more nerdy.  

 

Jesse: From a user perspective, nothing. I mean, I was a slave to my email and… 

 

Paul: Exactly. It’s boring, right? Most of the stuff that’s been done it’s all the essential business stuff, it’s good, it’s good stuff, it’s important stuff, but it’s not super exciting. Whereas Teams just opened up this universe, wow we can do all this incredible stuff. And I think it’s worth talking about. I think for me, by the way, Visio is probably the last product from Microsoft that I got very excited about.  

 

Jesse: I’ve been an Excel nerd on and off. I will say that. 

 

Paul: How about you Dave? What was the most exciting Microsoft product launch for you? 

 

Dave: Oh Access comes to mind 15 years ago, 20 years ago. 

 

Paul: Oh know that was 25 years ago. 

 

Jesse: I think I mentioned from a user perspective, but I think from an IT perspective, Exchange Online is a huge gamechanger.  

 

Paul: That’s true.  

 

Jesse: I spent the first several years of my Smart Dolphins career installing small business server for tons of times of clients around Victoria and those all had Exchange on-premise on them, which is a fantastic product, but I think all of my overnight repair. Anytime I’ve had to go through the disaster recovery hell or stay up all night doing IT was a recovery of an exchange server. They are just one of those things that works 99% of the time, but then when it breaks down, it can be an absolute nightmare. So I think migrating that specific piece of technology into Microsoft’s hands where it runs really, really well has been something that I’ve been excited about from them. 

 

Paul: And if you want to get into Teams (if you only get the full value) you really need to migrate. Office 365 has been out for almost a decade now, people need to be moving in that direction, that’s where all the security developments happening, that’s where all the product developments happening. If you want your Team’s calendar to integrate with your Outlook calendar, you really need to be moving it. I think we’ve covered that and we talked about security, why don’t we talk aboutAnd this is hard for me, because we’ve had this experience at Smart Dolphins where we switched to Microsoft Teams and we turned it on and we started using it in the productivity just moving the email. I think for me, probably the biggest thing is moving all that internal email we used to have into a different location to make your inbox so much more manageable has been just an absolute gamechanger, like an email for me, I think for most people, frankly, has just been like this daily nightmare that we all went through for a decade, and we haven’t had that? I personally haven’t experienced a lot of that in the last a year and a half or two years that we’ve had Teams now…Right. But that’s just one thing. And so when people ask me, they’re like, Well, what does Teams do and how is it going to help us? “There’s so many cool things.” If you were to summarize it, Jesse, or maybe highlight some of the points of what Teams has done and where you think it really makes a huge impact for small business? 

 

Jesse: Yes, that’s big question in terms of how you framed it. One of the issues Microsoft’s always had is they’ve had all these great products, but most people weren’t using a lot of them. SharePoint, I think is a very big change for the average person. SharePoint for those of you who don’t know you have to login to a browser to access your files which are stored in SharePoint. It’s a pretty big shift from the old S shared drive that we’re all accustomed too. Teams puts a client over top of all the services that you’re using it. Sstoring your files in Teams, they’re still in SharePoint, but they’re in the same client that you’re using all day long to converse with your teammates. So it’s very much like a hub for everything to do with your Microsoft. So I go into Teams to converse with colleagues internally instead of email, I go into Teams to access the files that I need to work, all of our team meetings are done through Microsoft Teams, so every morning we have an 8:10 company-wide huddle that is posted in a Team’s channel, and I just click the join button and jump in as does everybody else, and the same technology is used for all the other internal meetings that we have. Teams can even be your phone system. So last year, Microsoft releasea business voice license for, I believe is $25 a user that gives you a full-blown phone system in your Microsoft Teams client, so you can use the same features, the same method of dialing an outside party through an old fashioned phone system as you would chatting somebody through a video call in teams, so it can really bring a lot of different things in together. 

 

Paul: The last one’s a weird one for anybody who’s new to Teams or they’re just learning they may ask “why would I do that? But then when you start using the team’s environment, you start to realize, Wow, this would be really simple if my phone was just part of the communications hub, that’s now become so central to what I do on a daily basis, So…  

 

Jesse: Yeah, when you’re in Teams all day, it definitely doesn’t seem weird.  

 

Paul: No, not at all. 

 

Jesse: You can buy physical phones too, if you prefer. It’s basically a phone that has a little Teams app running right on the phone, so people who want the old school approach can still get that. 

 

Paul: Yeah, I think probably the selling feature now, especially within the Covid world (we’ve gone as far without mentioning that which is great) but for a lot of people, it was like, “how do we get our team talking together and suddenly they’re diving in, they’re jumping into Teams, and now that we got chat, we got video calling, which is great, we can get everybody with webcams and feel like we’re working together and stuff.” That’s been really good I think for a lot of people. But they also maybe miss some of the hidden gems in Teams like the file collaboration. And for me, we did these video meetings before we used Teams, we use Gotomeeting, we used Google Hangouts, back in the day, right? We did all these things and it was fine, and Skype, of course, has been around forever and owned by Microsoft, they took probably a chunk of that functionality and just put it into Teams. But I think for a lot of people, they miss the file collaboration part, and they say Oh, great. So me and my colleagues can collaborate on files. Well, how is that beneficial? Well, we’ve all done this where we’ve emailed a file to somebody (a Word document) draft up a Word document emailed it to six people, you get six responses back, three of them are editing the file, two of them are putting their notes in, somebody else is using some fancy red line function that hardly anybody even knows exists, and then you’re waiting for that one person to get back to you and of course their cc’d everybody’s else copies and you get this email avalanche. And you’re sending these big Word documents around to each other, instead of doing all of that, you can just have one file in one location that people can work on even at the same time. 

 

Jesse: Yeah, absolutely. And if you just sort of visualize what’s happening there, you’ve created six copies of an email with six different attachments in it, and then those are individually landing in everybody’s different inboxes, and then most people are going to hit reply to all and you’re literally spraying copies of information back and forth. You can also have people who will start dropping cc’s from the email, which is actually good in a lot of cases, but you do there, you break the continuity of the conversation, so it starts with six people and then it continues with three, and the other three that were dropped have no idea that the conversations even still happening. So by the end of a six-person email chain with 10 reply alls or more, you literally can get dozens and dozens of emails back and forthYeah, that’s a great point. In Teams it’s one conversation, and then people reply to that conversation, it’s all contained in one nice thread, that thread could have a document that’s being talked about and collaborated on. All 10 people or all six people could jump into that file at the exact same time and read it and modify it and everything, and you’re not ending up all those duplicates, so… yeah, that’s definitely huge. 

 

Paul: So many gamechangers, but you agree right? It’s hard to describe right to people who doesn’t know what Teams is. 

 

Jesse: Teams is a good example of what we talked about earlier, the shift to and in how technology is used and leadership taking a more hands-on approach. You can’t just set up a Team, invite everybody and tell people to start using it. You’ve got to have leadership buy-in, you’ve goto have people who, for lack of a better word, nag a little bit to help get people using the new systemIt is a big change, I would say, from the way people are used to working, it’s not a hard change and it could happen really quickly. But if you and I are chatting in a conversation and Dave keeps sending emails, someone has to say, hey, Dave, do you mind that email you just sent me, do you mind bringing that into Teams, so we can talk about it there?”  And that nudging has to happen overtime until everybody develops a habitSo it’s a bit of a culture change, but once you’re there then the emails are feel weird. When I get an email today, it feels really out of place (from a colleague). 

 

People might be thinking too about outside parties, what do you do there? And you do still need to receive emails from the outside world, so there is still a place for Outlook, but even with that, what we will do, if we want to talk about an email that we receive from an outside party, emails can be brought into Teams as well. So every channel in Teams has an email address, I can just grab that email address and go into my Outlook and just forward an email and it will show up in the Team’s channel, and then we can talk about the email as we do everything else and then I can go back to a look and reply to the outside party to client or whoever we’ve been discussing internally. So that’s another I think important piece that might get missed if people are thinking about how does this transition actually work. 

 

Dave: So with Covid, we’ve seen a lot of change really quickly and people looking at where the world’s going, and so we’re all trying to pull out our crystal ball and here at Smart Dolphins, we’re shifting Jesse’s role to CTO and trying to get ahead of this stuff. I guess I’m just wondering if we could shift the conversation to where this is all going, again, no real crystal ball here, but in the next year or two, three, five. Where does all this go? What are the key things to think about? 

 

Jesse: I do think companies need to recognize where they’re at today versus where they could be. Ty mentioned, again, I don’t want to repeat too much of what he said, but he talked about this, sort of thought experiment of starting over. If you started over today, you would probably fight really hard not to buy a server, you probably fight really hard to avoid any application that required a big on-premise database and a big upfront capital expense. More likely than not you’d be thinking about keeping it lean. Modern IT, in my opinion, is very lean, it’s very flexible. People want to work on any device, personal or not, personal or companyowned, they want to work anywhere in the world and they want to be able to work at any time. So companies, I think companies get stuck with where they’re at, they think, “okay, well, that’s all great, but we’re really dependent upon our application that we’ve got today and we need a server and our users won’t be able to change and deal with it.” Well, that makes sense. I totally understand that perspective. But where are you going to be in three years or five years or ten years? Right, at some point, depending on your business and I think this would apply to most businesses, you’re going to need to get out of that. And so I think having a good clear roadmap to getting lean. think about companies with all that, the older companies, I think it’s like fat, but there’s a lot of fat that you need to figure out how to lose over time, and so sometimes that’s really simple, and sometimes it’s not. We’ve got some fat and I’m actually on a call this afternoon with one of our vendors on moving our biggest on-premise applications into their Cloud version, because that’s one way that we can just get rid of some of the technology that we’re dealing with. So yeah, I think trying to look beyond the next quarter or even the next year and make sure that you’re pushing on those…the legacy that keeps a company from being able to evolve and be you managed in a more modern way and have all those features that I think everybody just takes for for granted these days. Like Covid really highlighted all of those things instantaneously, some of our clients went home and started working and we were good example of this, we were set up and in a really good flexible way, and that technology hurdle for us was almost non-existent. Our biggest challenge we Covid was just the rush of all of our clients, and also just adopting to being at home all the time, which is a challenge in and of itself. But there were other companies who had a lot more trouble they had there just trying to deal with how to get access to the legacy stuff that’s still sitting in their office, and they’re used to just sitting, plugged in directly to their server and that’s not going to cut it down the road. 

 

Dave: What about the business owner who says, Covid is just this one-off thing, I’m going to be back to my office next year, the server has been working fine for a while. Sure, I’ll just replace it. That’s what we have always done.” The getting lean or the fat, I think you explained it well but is there more you can poke out there, just to really convince the lager that wants to keep the server on-site. 

 

Jesse: Sure, well, I wouldn’t say that person is necessarily wrong, right, either. I think everybody’s in a different place, everybody’s dependency on technology and being flexible and things like that is going to be different. So I think there’s a lot of companies that are going to be fine buying another server in a year and continuing on, but I still think that the way that information isLet me back up a second. More likely than not, that company is going be using not just a file server in their office, they’re going to be using other things in addition to that, even if they still want to keep a lot of their data on site. They’re probably going to be hosting their email with a third party like Microsoft, they’re likely using other Cloud services, so there’s still a lot of things that those companies should be thinking about beyond just where their files are stored. They should also consider too the expectations their employees might have right in a company.  

 

Dave: Great point. 

 

Jesse: People more and more wanting to work for more flexible companies and see a progressive approach to technology. So I would say that’s something else to consider is that if you’re just going to just stay the same for the next several years, you could just end up in a place where could you built up so much debt that you’re so far behind that you’re going to struggle a lot to get out of it. So I wouldn’t say it needs to be an aggressive plan, I would just say having a plan and pushing that forward where you can is going to be a good idea for almost anybody. 

 

Paul: And part of the visioning exercise people should probably do is expect a decade from now their company is going to be running in the cloud, right, and what steps do they need to take along that pathway, right and I think that’s part of the business planning process. I think where a lot of people get stuck is they have that one legacy application that they have been using for a long time, and maybe it’s even the industry standard and they really need to use it, and it’s probably not going to have a cloud version any time soon, or there’s a new cloud version but it has bad reviews or whatever sort of thing like that, so they plan on keeping it around for a while onpremise and so. But then they stop and they say, “okay, well, we can keep a server anyway, so we’ll keep our email on-site, we will keep these other things on site.” And really not move the other components that they could be. And I think Jesse you would be able to speak to this a lot more wisely than I could, but the existence of Microsoft Azure services can really bridge some gaps on that. So if you’ve gotten yourself to the 90% point and you just have that one or two application that needs to be running on it on a file server (in order to keep operating) you can essentially fire up a file server in the cloud that’s running whatever operating system you need to keep that one application running, right. And so for a lot of people, just knowing that that even exists, and that could be the final phase to move off-premise, and it allows the people that need to access that application can access it from wherever they are as well. Right. So I’m not sure if you have thoughts around that, and I know we’ve seen a bit of that with some of our clients. 

 

Jesse: Sure, yeah, that’s probably the most common thing that ties someone to a server is the applications, the line business applications that your using, another one would be just a type of files, so it can be a lot harder to run for example CAD files. 

 

Paul: Large files. 

 

Jesse: Although doable. First focus on the line of business software. There are a couple ways you’d solve an issue like that if you’re trying to get more cloud-focused. One would be to do, as we’re doing with the vendor today, is talking to your vendors and seeing if they’ve got a SAAS model, which most companies are doing these days. 

 

Paul: If they plan on being in business in ten years 

 

Jesse: Yeah exactly. But alternatively, you can run server virtual machines in Microsoft Azure, which you mentioned as well. So it’s essentially taking your on-premise server that you’ve been running and spinning up a virtual version of that in the cloud and putting your application there, and then if you’re going to do something like that you have to also think about how people are going to connect to the application so that it’s going depend on the app, but if you think about the most basic version where you’ve got a client server connection of say QuickBooks on a user’s desktop connecting to QuickBooks, it’s hosted on the server, that’s not going to work very well, if you just sit down at your desk and connect to your cloud hosted QuickBooks running on a virtual server, right. It’s going to be fairly slow. So in that type of situation, you’d also want to be visualizing the person’s desktop that they work on. So I’m going to sit down on my desk, I’m going to double-click a remote icon, it’s going to take me into the Microsoft Azure Cloud where I’m going to have a full-blown Windows 10 desktop that I work from, and that’s going be my full-time computer that I use. 

 

What’s great about something like that is not only are you getting your servers off-site and getting your information hosted, but it speaks a lot to that flexibility thing that we talked about earlier, I can work anywhere, I can connect to that very secure environment from my crappy home computer, I can even adopt a less stringent policy at work around how often we replace our computers or what quality of machines that we buy because all the works being done in this remote environment 

 

Paul: And I heard Mac users can even log in on their Macs. 

 

Jesse, Yes, you can even take an iPad and connect to the Windows virtual desktop and get a full-blown Windows experience with a Bluetooth keyboard and it will work quite well. If somebody said, “hey, our server is getting old and we want to move to the cloud, we don’t want another server, then what we would do is migrate as much as we could into their Microsoft 365 tenant, get all the files that they share and all their My documents and all the things moved into OneDrive and Teams and then we would look at any applications that they had left behind and we would decide if we should… If we can move to a Cloud-hosted version of those things and just access them through a browser or talk to them about using that Windows Virtual Desktop approach. And then you can almost any business could get away from in an on-premise server like that especially small businesses that only have an application or two. 

 

Paul: Well, you’ve just opened up a whole other can of worms, which we’re not going to have time to get into today.  

 

Jesse: I am the King of can of worms at Smart Dolphins. 

 

Paul: Hopefully, for those people that are still listening, you get the sense that there’s a whole lot involved with all of this, and I think that’s the key thing is just having somebody who can help you navigate, and I know that’s something that I do in my role, but it’s so great to have a resource like Jesse and Ty available to try to get these things moving in the right direction because there’s just so many moving parts. There’s so many options that open up when you’re in that Microsoft environment, and when you’re trying to figure out that plan from where are we today to where we want to be five years from now. There’s a lot of directions you can go in and lots of steps you can take along the way. The decisions people make today are going be critical in terms of where they land, or whether they land five years from now where they want to be, right, so… Yeah, great talk today. Wow, thanks Jesse. I really appreciate all of your wisdom and insight “smart guy.  

 

Dave: Smart guy behind Smart Dolphins. 

 

Paul: Yeah. He’s got his pulse Microsoft. I feel like, Dave, we could have gone down any of the six or seven pathway pathways an hour each with Jesse but for the sanity of our listeners, probably good thing we didn’t. 

 

Jesse: I think maybe I’ll just add to, I’ve talked a lot about the risks and all the things people should think about today, but I think it’s also important to… Business needs to move forward and move quickly, and so there’s a lot of companies that are jumping into Teams without all the security in place, and it’s not ideal, but it’s not the end of the world either, it’s just… I think it’s just mostly about understanding what you should have done ideally in a perfect world and go back and fix listings where you can, or make sure you’re fixing them up front if you’ve got the time and help to do it. But there’s definitely a balance here of finding the things to address and when you can’t wait two, three years to get everything perfect before you start using tools.  

 

Paul: Well, we thought the Team’s transition was going to be something that rolled out over the next couple of years as people slowly began to adopt and move, and then of course, Covid-19 and all of a sudden, boom, we need a chat conferencing solution, what do you guys got? Well, you actually already own Microsoft Teams, so you could use that. Yeah, so there’s definitely a wide field between ideal and where people are at today, lots of messes to clean up, but of course for businesses that were able to embrace that they managed to keep going, which is the critical partWell, I think we’re done, Dave. I think so. 

 

Dave: I think so. A lot of words there. 

 

Paul: Yeah, thanks so much for joining us, Jesse Smith, the CEO, COO you like I did that eh, CEO.  Soon to be CTO of Smart Dolphins. Yeah, really appreciate you joining us today and we got lots more exciting episodes coming up with lots more exciting guestsDave, thanks for being here with me. 

 

Dave: Thank you, Paul.  

 

Paul: Always enjoy your company. And we’ll wrap it up, so everybody have a great week and we’ll see you on our next episode of Island Thrive.