Building Trust in Your Organization with Tom Bridge

Guest: Tom Bridge, Partner at Technolutionary and Producer on the Mac Admins Podcast

Episode description

Our guest, Tom Bridge, has made it a point in his career to build trust and bi-directional relationships with his clients in order to achieve the best working relationship possible. As an IT administrator, you have an innate responsibility to support the end-users in your environment while also ensuring everything is secure, and a major part of both of these tasks is trust.

[EDITOR’S NOTE: Since this recording has taken place, Tom Bridge has joined JumpCloud as Principal Product Manager, Apple. You can read more about his decision to join JumpCloud here.]

To learn more, listen to this episode of our podcast, Where’s the Any Key? to hear his take on trust-building in the world of IT and its importance for your IT company’s bottom line.

The following is a transcription of an episode of our podcast, Where’s The Any Key? Feel free to reach out with any questions you may have in response to this recording. You can find our show on Apple Podcasts, Spotify, and wherever podcasts are available.

Ryan Bacon: Welcome to Where’s the Any Key? the podcast where we talk about anything IT related and even some topics that are IT adjacent. I’m your host Ryan Bacon, the IT Support Engineer at JumpCloud®.

Introducing Tom Bridge

Ryan: Joining me today is Tom Bridge, he’s a partner at Technolutionary in Washington DC and a producer on the Mac Admins Podcast. Welcome, Tom.

Tom Bridge: Hey, thanks Ryan. I’m really glad to be here today.

Ryan: I’m glad to have you. Why don’t you tell us a little bit more about yourself?

Tom Bridge: Sure. I’m a partner at Technolutionary, we started out 15 years ago as refugees from an IT department that was about to face some downsizing. We decided to downsize ourselves and started out a consulting firm. At the time, we were doing some moonlighting for other IT companies and then we started building a business out of the whole thing, and now we’ve got about 65 clients — I have about 700 workstations in management right now as of three o’clock on Monday.

The mission of the organization is to provide IT operations support for small to medium businesses. And we do a lot of Mac-focused IT, mostly because most of our clients are Mac-focused organizations — it’s the platform that I choose to support most often. And we feel like we’ve got a pretty good array of clients, some of them are like law firms and some of them are design firms, and we do a couple of concert venues here in DC when there’s not a pandemic on. Our general focus is delivering that outsourced IT experience with a lot of personality and a lot of focus on user empowerment, I think, is probably the best way to phrase it.

Creating Bi-Directional Relationships With Clients

Ryan: Yeah, I feel that’s a really good relationship to have with your end-users is… have that trust there, have them feel empowered. And I think that makes things easier on both sides of the service equation.

Tom Bridge: For sure, and one of our perspectives is that we’d like to be the IT firm that says, “yes,” because we know a lot of IT shops don’t, and they’ve either decided for security reasons… and security reasons with the little trademark symbol at the end, because they’re not going to actually explain what they mean, which is, “I am too lazy to support this” at least properly or at least too lazy to set it up right the first time. And so they want to avoid a lot of red tape or at least user communication issues that they don’t know they have yet. And so most of our focus is around saying “yes”. I mean, that’s really what our users want, they want us to enable them to do the thing that they want to do.

We come at it from an improv perspective, which is, you never just say yes or no, you say “yes, and,” or “no, but,” to really build on what it is that they’re actually asking for. And sometimes it’s just a matter of understanding what they actually want and getting them to see it from a perspective of, “Maybe what you asked for isn’t what you actually want.” And so we have a lot of conversations that are, “Well, tell me more about what you’re trying to do. Tell me what you’re trying to accomplish.” And then usually it gets to a place where they say, “Oh, what I really want is to do this other thing over here.” And you’re like, “Oh, well we can do that, and that won’t require opening up your entire Google Drive for the entire company,” which is something that we got asked to do recently and they store confidential information in there. So, we’re like, “No, no, no, we’re not going to do that, but we’re going to help you figure out a way to do that that’s actually going to make your mission work.”

Ryan: Exactly. And I think that that leads into really what we’re wanting to talk about on this episode. And that is trust between the IT provider and the customer.

Tom Bridge: Absolutely.

Ryan: When you establish that trust, it really enables you to make those suggestions and to really help your customer get to where they need to go.

Tom Bridge: Right. And from our perspective, if our clients don’t trust us, we’re failing them. And if our clients don’t trust us, then why did they hire us in the first place? Some places do it because it’s like, “Hey, we’ve got to have an IT department. These guys seem like they’re not dumb as a bag of hammers.” That’s never really how it goes, you’ve got to have somebody that’s trusted. And establishing that trust and building that trust, not just with the decision-makers but with everybody you encounter, has been really, really important.

We had an onboarding, almost coming up on two and a half years ago now, with a fairly large client, and we had been interfacing with executives and we didn’t know anybody there. And so essentially, we’d been mostly talking with people who are up in the upper echelons of management and we went in to meet everybody and we were like, “Hi, we’re Technolutionary and we’re here to help.” Nobody really knew how to handle that, and so essentially we had to have a lot of conversations about what it means to be someone’s outsourced IT department. And one of the things they came back to us with, they were like, “Well, do you have a code of ethics?” and I was like, “Well, yeah, it’s mostly, don’t do stupid things.” And they said, “Yes, but have you written that down?” and we said, “Well, no, but give us the weekend and we’ll start thinking about it.”

So I spent a lot of time on Google, I spent a lot of time looking up what other organizations do. I found out that the SANS Institute has a really good open source code of ethics that has been around for IT practitioners since 2004. They publish it on their website, and it basically breaks out to three main sections. I will strive to know myself and be honest about my capability, I will conduct my business in a manner that assures the IT profession is considered one of integrity and professionalism, and I respect privacy and confidentiality. Those three big areas are like everything that I believe in, in terms of IT structures. And so we started looking at this and we were like, “Oh, this is awesome. This is exactly what it takes,” and so we provide that now, we handle all of their IT onboarding now for new employees.

We provide a link to our code of ethics in all of our initial meetings with new staff members. And it comes along with like, “Hey, we’re going to be reaching out about security issues. We’re going to be reaching out about IT issues, you can come to us at any time.” And we want them to be clearly aware that we’re going to hold that information respectfully, and we are going to do so in confidence, and we’re going to treat each other like adults and have clear lines of communication. And so for them to see us as an outside vendor who are essentially not signing on to the company employee manual, right? Which has a lot of those same rules baked into it that says, “I’m not going to be a jerk to my fellow employees, I’m not going to belittle them or anything like that. I’m not going to embarrass them.”

We have this secondary document that essentially helps us establish that trust with our clients. And it’s a big part of how you operate any business that is so integral like this to the trust nature of their business, that you have some rules for the road. And so once we established those rules for the road and once we made sure everybody had a copy of those rules of the road that we were going to follow, it was like we were part of their family all of a sudden. And people were opening up to us in new and different ways and we got to find out about a lot of issues that were happening inside of the IT environment that used to be handled by the VP of engineering.

And so essentially, he got freed up to do his day job which is actually running the engineering department that powers their company. And we got freed up to do a lot of the stuff that really enhanced their value long-term. All because we were really clear about where we were starting from in terms of what our ethics were, what our clear lines of communication were going to be, and we set up very clear expectations for how our staff were going to behave with their staff. And once we’d lined up those key features, it was just like the lights turned on, and everybody understood how this was going to work. And it paved the way for a much better relationship at that point.

Ryan: Yeah. That makes perfect sense, and I will fully admit that I have always been hesitant to do IT in an external facing role. My entire career has been internal IT mainly because I really value the relationships that I’ve always built with my coworkers, and looking at working for an MSP, working with external customers, I never really saw a way to build that same kind of relationship. And from the sounds of it, I’m completely wrong.

Tom Bridge: Well, no, I feel like there are a lot of MSPs that come in and don’t necessarily take the same steps that we take. They build trust in their own way, but sometimes those have negative experiences. We had to have a conversation with one of our clients when we took over the IT operations from another consultancy about what had been going on, and we built up the trust and relationship. We found out that they had been being badly over-billed by the previous company, and we had to break it to them where we’re like, “Look, I’m really sorry to report this, but I think that they were taking advantage of the trust that you established.” That’s not a good feeling to have to tell anybody, “By the way you have been taken advantage of,” is not a great conversation to have with people. And I feel like there are a lot of get rich quick MSPs out there, and there’s a whole school of thought around some of those, at least on the Mac side of things, that is very much maximize your your monthly billings and all of those things instead of helping an organization accomplish their mission.

Ryan: Yeah, yeah. That makes a lot of sense. Before I got into IT, I did a little stint in sales in which, more power to the salespeople, that is something that is not for me, but I did learn one thing and that was that if your goal is to help your customer, your client, meet their needs and not try to place your needs or your desires above theirs, that the end result and the relationship and the trust that comes along with that, is so much stronger than just steamrolling in and being like, “Hey, we’re going to do this, this and this for you,” without regard to what they want and just throw everything plus the sink into them, whether they needed it or not. And I think that, especially nowadays… I mean, this could be some wishful thinking on my part, but I think that nowadays, companies and people tend to be a little bit more savvy to that — just because of the sheer amount of information that’s on hand. You could just Google like, “Do I need 48 POE switches just to run five wireless access points?” That sort of stuff. Not only is it the right thing to do, it’s, in the long-term, the smarter thing to do to be upfront, honest, and fair.

Tom Bridge: Yeah. Well, some of it is also that a lot of MSPs are under a lot of pressure from their partner organizations, and I know that we partner with Ruckus, who are now part of CommScope. We partner with various other hardware providers, and I’m not going to say that there’s not a huge amount of pressure to deliver high sales as part of that process. And we come into it honestly and we tell everybody we partner with, when we want distribution access it’s for simplicity. It’s not so that we can maximize sales, it’s not so that we can maximize revenue and they’re not going to see us be a pump and dump partner. You’re going to see recurring licensing relationships with us, and we’re going to work through that process and where it fits, we’re going to make the sale. But we’re not going to over-provision sales and we’re not going to over-provision these environments.

There have been a couple of times when we had a chat with a company and they said, “Well, that’s really not how we like to do things.” And we said, “Well, great, thanks for telling me, thanks for being honest. I really appreciate that and we’ll find someone else.” I’m not going to do that to just counter, I’m not going to take on that kind of relationship if your values don’t match my values.

And we’ve had to tell clients that have come to us as well, to prospective clients rather, who say, “Really what I want to do is I want to put a keylogger on everybody’s machine and I want to make sure that everyone’s being productive all the time, and I want you to block all social media,” and we come at it with the perspective of if that’s how you feel about your employees, I’m not sure this is a good fit for us. Because I feel like that that’s highly invasive into people’s private lives and highly invasive into their organization and if that’s their whole idea, that if they think that these are people that are coming in, they’re cookie cutter, we can stamp them out like license plates and nobody should ever have any fun at work and no one should definitely ever watch the news at work and no one should ever be anything other than a hundred percent engaged in their work tasks. That just feels counter to reality to me, sorry.

Proving That You’re Here to Help, Not to Belittle

Ryan: It really does and also if the end user, if those employees… they’ll realize that those IT people are acting like big brother and they are essentially the enemy, or at least they’re not our allies on that, then there is no trust there. They’re going to be hesitant to reach out to you if they have problems.

Tom Bridge: And that’s the whole deal, they’re not going to work with us. Those are not people who are going to be deeply honest and say, “Hey, I clicked on a funny link in an email.” You’re going to find that one out the hard way, after they’ve gutted your network. Cooperation between the average employee and the IT folks is absolutely critical especially in 2020. We did a phishing exercise last week with one of our clients and sent out 150 emails that were essentially saying, “Hey, we saw a suspicious login on your account, please log in to report this information.” So, I mean, it’s clearly a phish. We had more than 50 people report it within the first 10 minutes. Most of them were reporting it through the established mediums, but we had people DMing us on Slack, sending it to our personal emails to be like, “Hey, this looks really weird.” And I think the security thing, the only reason that they would do that is if they trust us.

Ryan: Exactly. And along these lines, this is going to be me bragging about my end users a little bit, but we changed password managers recently and we were under a time crunch to get everything migrated over. I put out an email, a company-wide email, with instructions on what to do and everything like that, which can very much look like a phishing email. And I had just seen the people chime into our security channel on Slack, DMing us, emailing directly saying, “Hey, is this legitimate?” just made me so proud — that security training and also the fact that they felt comfortable questioning an email from me. I’ve never been more proud of my end users than at that point.

Tom Bridge: When I was first getting started in IT, I was working helpdesk, and how many people have ever seen that Nick Burns skit on Saturday Night Live, where Jimmy Fallon is like, “Move,” and he does a bunch of things and he makes fun of the user and be like… show me someone who doesn’t have that IT experience in their back pocket, and can pull it out and be like, “This was where the IT guy was a jerk to me,” because it’s always dudes, I’m sorry, it’s always dudes who are like that. But, the experience of that broken trust isn’t something that most people have engendered in IT, but it’s something that they see often enough that it’s a problem. We used to call First Class, we used to support First Class as a large email system, for a company of 200 and First Class as an email system, actually was pretty cool.

There were a lot of cool things that were like Google Groups before there were Google Groups with their conferences feature. There was a lot of good stuff in there. I liked it a lot. But there was the rule in the department of, if you have to call support for First Class, and we did probably about once a quarter — something being weird or a backup not working right — if you got this one guy and his name was Don, if you got Don, you hung up and called back. Because it just got to the point where the IT department head was like, “Look, don’t talk to this guy, he’s a magnificent jerk.” And it was just known by all the helpdesk folks, if you get this one guy, hang up and call back, you’re going to get somebody else. And I think about that now and I would shudder to think that that was any of us in IT now. I mean, if that’s the relationship you have with your outsourced vendor, something is badly wrong.

Ryan: Yeah. I completely agree, and my biggest goal for any IT department that I’m part of, is that we fight against those IT stereotypes, we prove that we are there to help and go for that customer-centric approach. It makes me so happy to see that that’s becoming the norm, because I’ve known people who’ve been in IT three times as long as I have, who held that stereotypical mindset of, “The end-user is stupid and they don’t know what they’re talking about and it’s my job to clean up after them,” and I resent them for it. First off, how can you work in that kind of environment? How can you live in that kind of environment? I would be miserable, just being angry and resentful all the time.

Tom Bridge: I mean, I know some of where that comes from, and some of it does come from people on our teams that we see, who say things like, “Well, I’ve just never been good in technology,” or “I’m technically illiterate.” That’s my favorite of the bunch, because those are also people who, if you ask them the question, “Do you think it’s okay to admit that you’re illiterate about something if that was part of your job?” And so that incredulousness that comes along with this, gets to be endemic as time goes by, but the way that you fix those problems is by realizing that what they’ve learned, is that if they try to understand it, they’re going to get made fun of, or if they try things it’s going to break and then they’re going to get made fun of for trying things. And so you’ve got to build your trust in other ways with those folks and essentially, those are folks that you’re going to have to spend more time with.

Ryan: Yeah. It’s one of those things where they say 80% of your problems are going to come from 20% of your customers. And I worked in an environment where I came in as the one-person IT shop, and the person who was there before me was real condescending… you ask them to do something and they’re like, “Fine, move.” It took me a while to establish trust, and having to deal with the repercussions of that, I mean, I don’t know how many times they’d finally come to me and be like, “Hey, this printer hasn’t been working properly for four months.” And it’s like, “You’re telling me now. Okay, I’ll fix it.” It’s fixed within 10 minutes. And the more I kept doing that, the more that I let them know that they matter and that they have priority, helped to build that trust. So by the time that I left there, people weren’t afraid of reaching out and saying, “Hey, we have a problem with that.” I never made fun of them. If I were to go and make light of the situation, it was generally self-deprecating or joining them in ridiculing the stupid printer that it can’t do what it’s supposed to do.

Tom Bridge: It’s always the printers, right?

Ryan: It’s always the printers. Yeah. And it was good to see that things were working as they should, the relationship between IT and the front line – the rest of the company was right. And another part of that that made it very important is that I made myself visible. I didn’t just sit in my office or sit in my cubicle the entire time and just be like, “Come to me if you need something.” I would essentially make rounds. First off, it’s good to stretch your legs. But while I was doing that, I would check in and be like, “Hey, is everything going okay?” And part of that was necessary because at first people weren’t telling me when there were problems, but also it showed that I care. And if they think that you care, then that just cements that trust and their willingness to work with you.

Tom Bridge: Yeah. And having that conversation, we used to schedule just office days with a bunch of our clients where we wouldn’t charge them extra, but we’d just come work from their office that day. I’d come and take up space and a spare desk or something like that and make it a point to walk around and talk to folks and just make sure that everything was going as expected. It’s a lot harder now to do the same kind of thing. And so we’ve been doing a lot of emails just to be like, “Hey, just checking in, wanted to let you know about some other thing. Hey, we’re doing some new updates this week so look for those in your queue. And by the way,” trying to get that extra thing. “I just want to make sure the folks are okay.”

And because there are so many places where we find out three or four weeks later, that there was a problem with the backup, that they were getting a funny message and now suddenly they need something off of that backup that doesn’t work anymore. And then, it’s like nightmare-scenario, because it’s a broken trust that leads to more broken trust. Those are the kinds of things that are heartbreaking for me, at least, in terms of where we have to overcome those situations because it’s just like, “Damn, if I’d reached out to that person just to make sure that they were okay, we would have had a real slam dunk of an experience.” And that’s one of the things that we talk about a lot internally, I just ask folks, “Hey, is there anything I can do for you?” From an IT perspective and just treating it from that perspective of, “Is there anything I can do to help out?” Especially when you’re an exterior team member, right? There’s nothing that shows your value to your colleagues than offering to help them. And they’ll remember that because even if there’s nothing you can do in that moment, they remember, “Hey, Tom said, if there was anything I can do to help.” I wonder if this qualifies? And then just getting that out there and having that conversation.

One of the other things that some of our folks find confusing is that now when we do remote screen sharing sessions with them, we use a tool that provides a nine or a 10 digit ID and then a password for every session. And so we use that as an explicit consent with our folks to basically be like, every time we start a phone call with a, “Hey, can we do a screen sharing session?” and we jump into that screen share, we get affirmative consent for jumping in and seeing their screen and we specifically say, “Is it okay if I see your screen and control your computer?” Because that takes away one of the things that folks are untrustworthy about random people in their computer doing those kinds of things. But that explicit consent statement that happens as part of all of that is so important to folks getting to trust you, that you’re not able to just jump into their machine. Because that’s weird, it’s like sitting down at their desk when they’re not there or when they are there. And you got to make sure that you’ve got their permission to do that. 

If you have a relationship that’s respectful and trusting like that, the number of things that you can get out of the way early is just great, because one of the things that we make sure that our clients know very early on is like, “Hey, if you ever have a question about whether an email is phishing or whether a message is weird or anything like that,” we basically come out and flat say, “I would much rather tell you no, that’s phishing or no, that’s not phishing… or yes, that’s a weird dialogue.” I would rather do that a hundred times a day than miss something. Because the cleanup from missing something is tens of hours, thousands of dollars, and it’s just rough for everybody. When it’s a five-minute question or that we’re going to comp you time for, everybody’s afraid with outsourced IT departments that you’ve got to manage them very closely or their budget’s going to go way out of whack. Well, no. Yes, occasionally there are going to be some situations where you burst upwards, but it’s usually because you’ve got some pent-up need that’s not been addressed elsewhere.

Ryan: Right. And on the internal side, even if you’re not billing, they’re still… what I hear most from our team is like, “We know you’re busy, I don’t want to waste your time,” that sort of thing. But along the same lines, we make it known, you’re like, “I’m more than happy to take those few minutes to look at something and let you know,” than go and have to try to recover from a ransomware attack. That is never fun.

Tom Bridge: That’s no one’s idea of a good time.

Ryan: Yeah. I think that it’s different but similar, whether you’re internal or external, that some upfront investment in time and communication with your customers pays dividends. And again, it shows that you’re approachable, it shows that you’re available and that you’re trustworthy, and that makes it more likely that they will come to you when it’s vital that they do. And we put in, at JumpCloud, we have a zero fault policy. We’re all human, we all make mistakes. As long as you’re not trying to cover up a mistake, we will mitigate it, you don’t have to worry, you’ll be fine. Just let us know. And I think having policies, not just having policies like that, but communicating those policies is vital. And that runs counter to the type of customer that you were talking about before, who wants you to have your fingers in everything of their employees and make sure that they’re not doing anything that’s not productive and… I’ve just completely lost my train of thought there. Okay. I’ll just skip over that, I don’t think that was really going anywhere.

Having that trust, having that communication out there really is important to an efficiently running IT service whether it is internal or external. And those relationships that you build with your customers, I keep wanting to say end-users, because that’s how I’ve always said it but after thinking about this more, ever since you brought up this topic is that… that phrase, the end-user, is kind of a holdover from those dark days of IT, because you’re not really looking at them as a person.

Become One Team That Works Together

Tom Bridge: I like ‘colleagues’. ‘Colleagues’ is my jam because it’s incredibly familial, and it keeps things really clear – that we’re all pros here. We are all people that are trying to get stuff done. We are trying to get to the end of the day with our tasks accomplished on behalf of the mission of the organization. And that’s the other thing that we also have to tell people, is that your mission is our mission, we are part of your team. And if we’re not part of your team, then it’s not for lack of trying. But building that kind of trust internally is all about how you see people. If you keep saying, “Well, my users, blah.” And well, my colleagues, my friends, my coworkers, those are… we would often say my friends in X department, would be another way to handle it.

But using humanized language, using empathy as a tool in your favor, is the secret weapon of any service IT department or as any service department, not just service IT, but service to the organization. Empathy is your number one goal. You need to understand what your people’s challenges are, you need to understand the conditions that they’re operating under and use that to build your response. And that’s hard fought in a lot of cases. I have had a lot of interactions with IT departments that are much more concerned about their own reviews than they are about the needs of their users. They’re trying to avoid a negative review by being very, very cautious and I can understand that. But they’re also delaying a project that should take two weeks to accomplish, and pushing it out over a 90-day timeframe because they’re afraid.

There’s always some healthy amount of fear that should be in IT. A lawyer friend said, “Being an in-house counsel is like having thousands of little panic attacks on behalf of your coworkers every day.” And I feel like IT is very much the same way, good policy comes from thinking about what could go wrong and that’s important. Having those little panic attacks in the hallway as you’re thinking about what could fail with a firmware upgrade, I get, totally. I get it. But that should not paralyze you into non-response or non-action. And that’s a challenge.

Ryan: Yeah, it is. I mean, because at the end of the day, bottom line whether you’re internal or external, the job of IT is to increase the efficiency and effectiveness of business operations. If you’re, like you’re saying, if you’re driven by that fear, if you’re driven by mistrust, anything like that, that’s hampering that base goal and anything that you can do to streamline things, to improve communication to give you better insight into what the organization needs, the more effective you’re going to be at that goal. And I think that a very effective way of doing that is open and trusting communication with your colleagues and with management, top to bottom. Everybody within the organization because everybody brings important insights to… everybody holds a piece to the larger puzzle and talking to everybody will give you that bigger picture and help you achieve those goals so much more effectively.

Tom Bridge: Well, one of the systems that IT is responsible for inside any organization is for the proof of identity, right? Like we talk about directories and things like that and putting together applications so that they’re single sign-on so that we trust. We are the trust enablers for an organization. If our people don’t trust us, then there’s more than us they don’t trust. Like their own systems, like their own endpoints, like their phones and stuff like that. So, understanding that there are ripple effects to failing that trust check, that will cascade through systems that you are lovingly maintaining, even unintentionally creating that appearance of mistrust gets to have real consequences for an organization. So if you think that you’re spending a lot of time on structural identity, then you’ve got to spend your time on the identity of your own department and the trust of your own department in the hands of your people. And if you’re not spending your time thinking about those things, it’s going to be a real challenge to get over that hurdle of building better internal trust, let alone external trust.

Ryan: Yeah. And that actually brings up another good point, another thing tied to that trust and that’s something that I can’t think of a single IT person that doesn’t like, and that’s shadow IT. I mean, if they don’t trust you, they’re going to go off, your customers, your colleagues are going to go off and they’re going to find their own solutions for better or for worse.

Tom Bridge: That’s right. We found out recently that an organization had switched to Zoom internally amongst about half their staff. Did they set up Zoom right? They did not. No password security, very little structural security inside the application itself. Nothing bad came of it, but it could have. And those are the kinds of things that IT is there to protect. And essentially we found out that this had happened, we asked questions like, “Well, what was Zoom doing for you that Webex was not in this case?” And we had a long conversation about that and we were like, “Oh, okay, well, let’s make Webex do those things.” And they were like, “Wait, wait, that’s an option?” “Sure. I mean, we’re happy to make changes that fit the structural mission of the organization,” and made a bunch of changes and suddenly they realized, “Oh, if I talk to them, they fix things.”

Ryan: Yeah. If it turned out that Zoom was actually the better option then hey, you could have done a proper structured migration and things would have been so much easier for everyone.

Tom Bridge: In a lot of cases, those things like proper structured migration, people get the fear of the project manager in them. Like how many meetings is that going to be? And I have one project that’s on my docket right now where I know I have weekly meetings about it, but I’m not responsible for anything that’s happening in this project. I’m not the directly responsible individual, so it’s just meetings I have to attend and I hate those. And so I understand their fear of that kind of thing. But, by the same token, if what we’re doing as part of all of this is coming to them and saying, “Well, we see a bunch of Zoom use, could we switch over and save a bunch of money because Zoom is cheaper than Webex in this case?” “Well yeah, totally.” And then, and then everybody comes away with, “Wow, we saved $400 this year.” And they start thinking about, “Well, maybe I’ll get four of that and a bonus somewhere, and that’d be pretty cool.”

Ryan: Yeah. It’s amazing what can come of talking to your IT department or talking to your colleagues. Because I don’t know how many times where… it’s actually really common that somebody from department Y will come to me and be like, “Hey, we need a solution to this problem. I’ve looked at these other ones here,” and I’d be like, “Oh, department X is using this product already that will meet all those needs. We already have this business level or enterprise level account.” Consolidate tools, let them know. That gets departments talking to each other as well because then they’ll be sharing knowledge outside of that, which is another thing that I try to foster in our organizations, not just people coming to IT for help.

JumpCloud uses so many different applications, there is no way that a small IT team is going to be familiar with the ins and outs of everything there. So I make it a point to also reach out to the people who’ve been using these applications for years and being like, “Hey, can you give me some insight? How do you do this?” Show them that we also want to learn from them as well. That feeling that they get, they’re like, “Hey, I just helped IT.” That makes them feel really-

Tom Bridge: Yeah, no, totally.

Ryan: People love that, and along those lines I make it known, like when I was regularly doing our onboarding, our other team member, Noah, he handles all of our onboarding now, but when I was regularly doing our onboarding, I would tell them, “My goal, is so that JumpCloud has the best IT department that you’ve ever worked with. What that means, is that if you ever see us doing something that’s rubbing you the wrong way or if you’ve worked with an IT department that you thought was phenomenal in another way, let us know. Our success is going to be based off of how you feel we are doing.”

Tom Bridge: Yes, absolutely.

Ryan: I’ll be completely transparent with you whenever possible. When you hold the keys to the kingdom you have access to a ton of information, stuff gets shared with you. You can’t always share all of it, but if you’re transparent with the stuff you can share, they’re more likely to believe you when you’re like, “Hey, I can’t really talk about that.” So, as you mentioned before, being like, “yes and,” or “no, but.” If there’s another reason, be honest with them. I’ve told people, “We are doing option A instead of option B because…” it could be something as simple as, “More people in the organization are familiar with option A than option B, so it’d be more resource intensive and there’d be too much of a drop in productivity to move over.”

But then again, if option B is head and shoulders better, then we’ll be transparent with management being like, “Hey, there will be some growing pains into this, but we believe in the long run it’s going to be worth it.” I’ve found that it makes my job so much easier and having the trust of my coworkers and my colleagues from all around, like I’ve shown my finance team that I don’t ask for frivolous things, that I do my homework before asking stuff. So I’m already two or three steps ahead when I come and I ask them for something because they’ll be like, “Okay, if he’s asking for it, then we should at least think about it.”

Tom Bridge: Yeah. Well, and we get into the point where not everybody thinks that IT is a people-focused job. A lot of people think that IT is a systems-focused job and to some extent it is, but there was one of those great Twitter threads the other day that’s basically, “Explain your job, wrong answers only.” And I would say that my job is a human-computer interaction therapist. But that’s absolutely true, my job is a human-computer interaction therapist. Because essentially, in a lot of cases, we’re there to help manage people’s relationship with their own technology. And while I don’t have a couch that I travel with, I feel like I definitely had those sessions in executive offices where essentially I’m acting as their therapist as they deal with their computer.

But it’s all about building the trust that goes with those systems because systems don’t trust each other naturally, right? And that’s true for a lot of IT systems. So if you’ve ever set up single sign-on, you know exactly how much work goes into trusting other systems. And building those relationships of trust, those apply between your people and their computers and your people in their systems all day long. And so at the end of the day, what I really want folks to take away from all of this is that your job is as much a human-computer interaction therapist as it is systems engineer. And IT is a people-job. IT is always a people-job.

Ryan: And I will say that’s one of the big reasons why I chose IT instead of going into CS, because sales may not be for me. I do like interacting with people and then of course on the flip side when my introvert starts peaking it’s head, I can go and I could bury my head in work if I need. So I find it to be a beautiful balance between the two and along those lines, I had a conversation with my manager and my manager’s manager about, as organizations grow, they always are evaluating like where does this department fit in the grand scheme of things? And like where does the IT department fit? So like right now we’re under business support services.

We used to be under operations engineering which is where dev ops and security teams live. And they were asking me like, “Do you think you should go back over to engineering? Should it be under BSS, which is a subgroup of finance. And I’m like, “Well, the thing is each of those are like facets of what IT does.” I mean, really there should be business operations and that to me, that’s where I feel IT fits, because that covers… we’re like facilities, engineering, sales support, well, not just sales, everybody-support. We have our fingers in every single part of the business. So, in a way, it doesn’t matter where you are as long as you can do your job.

And if you want to put it on paper, like where this department should live, it should be in a place that has exposure to everyone. And I’ll say this, when we moved from operations engineering over to business support services, that nothing changed, which is how it should be. Because we already had these relationships with everybody else, we were already working across departments. We had the trust from higher up to be self-sufficient and autonomous. And so it didn’t matter where we were on the org chart, we’re still going to do our job to the best of our ability and help everybody that we could possibly help. And I think that, to me, that was a great sign that we were doing things correctly.

Tom Bridge: Absolutely.

Ryan: And I don’t think that would have been possible if we didn’t have that trust established not only with our colleagues, but with the management team.

Tom Bridge: Yeah. If you don’t have the trust in your management team, that’s again, a lot like another IT department not being trusted externally. You’ve got to really work hand in hand with all of these people. So, I mean, that’s a really key part of a lot of these — and organizations just having a clear understanding of a collective mission and having buy-in from everybody involved.

Closing Remarks

Ryan: Exactly. Couldn’t have said it better myself. So again, our guest has been Tom Bridge, thank you very much. I thoroughly enjoyed talking to you.

Tom Bridge: Thanks so much Ryan. I really appreciate it, and if folks want to read more about what I’ve written on IT stuff, I’m out at or please feel free to stop by the podcast at And you can find us in any directory where your fine podcasts are found.

Ryan: Alright. Excellent. Thank you very much Tom. I knew that I was going to enjoy this and it definitely happened.

Tom Bridge: Excellent, I’m so glad.

Ryan: Thank you for listening to Where’s the Any Key? If you like what you heard, please feel free to subscribe. Again, my name is Ryan Bacon and I work for JumpCloud Directory Platform, where the team here is building a cloud-based platform for system and identity management. You can learn more and even set up a free account today.

So until next time, keep looking for that any key. If you find it, please let us know. 

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