The Trusted Advisor Blueprint: Evolving VCIO, VCISO & AI Leadership in MSPs

[00:00:09] Hey everyone, welcome to the latest installment of MSP Business School. As always, I'm Brian Doyle here to kind of guide the way. And today we're going to have a little discussion, this is actually going to be just me talking this week, about, you know, a concept I've been seeing a lot talked about online. And, you know, there's a lot of different terms going out there, you know, we're all familiar with the VCIO term, obviously it's near and dear to my heart as the leader of VCIO Toolbox.

[00:00:36] But we hear a lot about VCSO, and now we're hearing about virtual chief AI officers. And there's a lot of these different things going on. And for MSPs, where it's already overwhelming to kind of see where you fit sometimes within the customer's leadership hierarchy, all these different roles and responsibilities can be challenging to integrate into your business.

[00:00:57] So today I really want to talk about the concept of just external leadership, how we as outside consultants, as third parties can embed ourselves into the leadership fabric of the customers that we serve. And this is really something that has been a big part of my life as I worked in the MSP. As many of you know, I wasn't really technically based, I certainly gained some technical chops over the years.

[00:01:25] But really, I've always come from the business and leadership side of things with our clients. And QBR is obviously being very close to my heart, as that was something that I was doing plenty of as I was running my organization.

[00:01:43] And one of the things that, you know, I came to realize during that process was, the more I engaged my customer, and the more I listened, the more they brought me back in to talk more and get suggestion. So we talk about that concept of trusted advisor and ending up in that seat.

[00:02:01] But really, what I've started breaking down a little bit more, and what I share with a lot of people that I get the opportunity to train at VCIO Toolbox, is that as external leaders, we really have an opportunity to build trust and earn respect along the way, which then puts us in that capboard seat of kind of, you know, leading IT in a way that's beneficial both to the customer,

[00:02:24] but also to us as the MSP. But it all starts with some basic tenets into how to be an external leader to your organization. And one of the things that I want to kind of bring up first is kind of the challenge of external leadership, the things I hear most often. Where do I fit within the organization? You know, there's this process to becoming an external leader, you don't just show up and earn that respect.

[00:02:51] And it takes time to see where you're going to fit within that organization, because not any two organizations are going to want to engage you the exact same way. Some may want to embed you and really have you sit within their board meetings. Some might reach to you just for guidance and look for your insights. Others may look at you and say, no, we just want you to be a tactical partner and push you at hands off. But you still have to use some leadership qualities when that occurs as well.

[00:03:17] So really what you got to say to yourself is, what do I want to accomplish here? And what are the things that I want to do for the organization? Then we'll get through the challenges of where I fit. Am I an employee, a vendor, a partner, right? And those are some important distinctions as well. It's understanding how much authority you really do have. We want to bring trust and leadership, but we don't want ultimate authority. And I'll get more into that as well.

[00:03:44] And when do I have to push and when do I need to step back with a customer? And that is really kind of an art form that comes with time, right? Because you want to push, push, push. But there are times where you need to take a step back and realize, hey, I've got to really listen here in this case. So I want to talk a little bit about that. But it all starts with understanding your lane. And if you clearly don't understand the lane that you're occupying, what your relationship

[00:04:14] is going to be with that customer uniquely to them, you're either going to overstep your boundaries and start trying to push decisions that go beyond what you should be providing to your customer. Or you're going to under deliver on your services. You're going to be too passive. You're not going to be aggressive with them. And you're going to fall behind. And eventually that could lead to dissatisfaction. So it's a very happy balance of how we engage with these customers.

[00:04:40] Now, I mentioned this a little bit earlier, but trust is something that's earned, not given. Too many younger VCIOs I work with think just by showing up at the QBR, coming armed with the information a platform can bring them in a cadence for running their meeting that they're immediately going to earn trust. And the truth is trust takes time. Trust is an evolution. Think of any relationship you've been a part of.

[00:05:07] If you've ever dated before, you know it takes time to build trust with that partner and get to the point where the relationship can progress as it naturally would over time. So when we look at trust building, I like to say that it breaks down to a nine-month process. Months one through three, it's really learning and connecting about with the customer. When I'm getting started with a customer, even if it's somebody we've been working with, but now I'm getting more engaged as a leader. It's all about understanding them first.

[00:05:37] You know, the old saying, use two ears and only one mouth. It really comes into the leadership perspective too. Go ask questions, but then listen to the responses. What we really want to do is learn about the business at a greater level. We want to go beyond understanding just what they do, but how they do it. Why are they doing it? What are some of the cultural components of what they're doing for their customers within their organization? How do they operate internally?

[00:06:06] What's important to them? What challenges are they facing and obstacles on the way to success that they might have to leap over? What are some of the goals that they want to bring to the party? Even if they're sitting outside IT, trust me, they're important to learn because it's going to give you a well-shaped, well-rounded understanding of what the customer does. And then as you start putting together an action plan, you're going to be able to tie back to those items that you've collected and really help them see the why and get much more in tune with that.

[00:06:36] So when you really look at your first few months of working with a customer, you really got to go in there and go, I'm going to listen. I'm going to try to understand. Sure, if asked, I'm going to make suggestion, but I'm not going to push too hard at this stage. I have to establish myself as a leader within their organization and make sure I understand what they're trying to accomplish. In months four through eight, this is where we really start building confidence with the customer. At this point, we may have started building some projects out with the client.

[00:07:06] So we've had some hopefully quick successes and quick wins. We've conducted a QBR or two. So they're getting used to our style, understanding how we're approaching things, seeing what those outcomes are, both from a business perspective and a tech perspective. And we're flagging issues early as a leader. We're listening to those customers when they feel something is kind of going sideways or if they're not getting enough out of a certain technology. And we're able to jump in and kind of push that along as well.

[00:07:35] And then finally, when you get to month nine, now you're leading with influence. You've built your resume with the customer, if you will. You've started really engaging with them at a deeper level. And hopefully at this point, you've demonstrated your value. And if you do this, now you can start extending the relationship, start really understanding or pushing on those projects when they need to be done. You've earned the right here to say, hey, these are really high priority projects and why?

[00:08:02] Especially some of those security projects that often get stalled because they're just not sure if it's really going to make a difference. Well, hopefully at this stage, we've built enough trust that they're understanding, hey, we're only here for your best benefit and that these things really are going to help you as you move forward. You know, and when we make this transition too, I always say if you're doing it from a VCIO perspective, this is a great time to start asking your customer about, hey, do we want to

[00:08:27] integrate other contracts, other services you do into our roadmap so we can look at the whole picture a little bit more holistically for you? I always believe that once I got to that stage where my customer would start giving me things like cumulative labor costs or ERP licenses, things that I'm not in control of to bring into the budget, I'm really finding myself in a sticky place where now I'm making a difference within their business.

[00:08:52] And they're starting to offload some of that work that would normally belong to other officers. Think of it this way. Many of your CFO partners that you're working with out at your customer sites, they're managing five, six, seven different departmental budgets, IT just being one. And if we can become the steward of the IT budget plan across their entire organization to the point where they're calling us up, you know, three, four months before the end of the fiscal

[00:09:19] year, asking us for that budget so they can integrate it in with their others. Now we're really in a place where we're making a difference within the organization. We have good trust. Obviously, we've established ourselves as an external leader to their organization. And now we're embedding ourselves for the long term because we are now the steward of that budget and forecast. And it's going to be very difficult at times to decouple us from that process.

[00:09:48] So we really, you know, need to kind of establish that over time. When you really think about what your job should be, if you're a VCIO or a VCSO or a virtual chief AI officer as well, you're not there to be the sole decision maker. You're there to advise, influence, and translate the information you're providing. We're advising them on the steps that they need to take. We're influencing them by building that trust.

[00:10:17] We're now helping use that to kind of show them, hey, these are the things you need to do and kind of push them in that manner. And then translate is really connecting the dots back to the business objectives. You've heard me say it a thousand times. There's posts everywhere. If you are not showing the customer the why, you're going to have a hard time getting projects moving within your QBR process and within your relationship. If you really think of what the VCIO is supposed to be, we're really there not to be the decision

[00:10:46] maker, but we're a force multiplier behind the decision makers. If we can get more of those people on board with us, they're going to help drive our initiatives forward as well. And that really brings us to another topic, which is you got to get deeper than your point of contact in your organization. And a lot of you have told me over the years, but yeah, but we get position there. The person's scared that if they, you know, sometimes that if we get past them, it's going to make them look bad.

[00:11:15] First off, get in sync with your direct contact across the way. Help them understand that your reasons for wanting to meet other people in the organization have little to do with taking over their role. First of all, we're not built that way, right? Our work, we need to be working with many organizations for our role to be effective. And we take that information. We learn from many organizations to be able to showcase to our customers. Hey, this is what we're seeing on the outside.

[00:11:42] So once we help them understand that the real reason we want to reach out to those other parties is to understand what their given needs are. You know, a lot of us have never gotten to a line of business leaders, i.e. department head, you know, within an organization. And when you get to those department heads, you get fed some of the greatest information that's going to help you understand where gaps live and what next steps can be taken. Especially in this age of AI now, where we're looking at how to really make people more efficient

[00:12:10] and automate their workloads. And down at the line of business, that's where they've got visibility into where the real day-to-day work is happening. You know, when you talk to a CEO or a CIO about this, oftentimes they just don't have enough context to be able to tell you. They're not doing that day-to-day work. They're sitting in a different realm where they're now looking at big picture impact things, but not tactical day-to-day mundane workings, which are the kinds of things that we're looking

[00:12:37] at to, you know, to build out an AI opportunity. So it's really good for us to get to those line of business leaders. With our financial teams, we want to understand where their gaps might be. Are there certain types of reporting they're missing? Or is there different functions that they would like to do? By having these conversations with these people, we're going to identify where gaps are. We might even be able to see where to extend their existing tools. I mean, there's a ton of stuff you can use in Microsoft today, right?

[00:13:07] And if we can extend some of that stuff out at no cost or very low cost to those organizations, that's going to be a quick win for us as well. So we really want to get to understand these other people within the organization so we can really build a core team that we can communicate to. And especially in times where projects are starting to stall. Hey, let's get them as advocates. Hey, here's a project I'm trying to get through. Here's how it's going to benefit you and your team.

[00:13:35] Here's how it's going to benefit the company at large. And if you can help illustrate that story to multiple members within your customer environment, truly being a leader, right? You're going to start seeing that things are going to move a little bit faster than they have previously as well. So you really want to kind of, you know, work with those different leadership teams and you have to get very specific on how you're going to approach that. When I think of the three core areas, right?

[00:14:02] Let's think CFO, CEO, and MSP operations or the operations teams within the organization. With the CFO, here's what we're not doing. We're not approving budgets. We have no fiduciary responsibility. And if you think you should have that, I'm going to caution you. Talk to your lawyers. You probably don't want that. You are there to advise. You're there to direct. But you're not there to execute and make that decision.

[00:14:26] So what we're really trying to do with the CFO is help them align priorities and understand financial tradeoffs if there are projects they have to push to the side for a little while. So when we get with the CEO and executive teams, what we want to help them understand is risk. And this is a great place for us to live because there probably is no greater risk short of running out of money than some of the cyber threats that are out there that companies are facing.

[00:14:53] And we need them to understand their risk profile, understand where the biggest impacts and likelihoods live. If we can quantify that number, it's going to help them make much more informed decisions. And you're never going to talk to a leader of any company that doesn't want to de-risk themselves. The question is, can they do it within the budgets they have? So we really want to work with them to make them understand at least where the risk is from a priority perspective so they can make informed, confident decisions about whether or not to

[00:15:22] execute on the solution behind that risk. And when we start talking about our operational teams, we're there to execute the operations or the delivery of the technologies. But we do need to make sure that they're aligning with the needs of the rank and file. And how many times over the years have you been part of a project that was delivered out or a new application that went to one of your client companies and they said, it actually does less than before or this doesn't meet the way we do our business.

[00:15:52] And this is where we can really listen, understand, and then influence when they are looking to make those different kinds of technology selections that might be outside the scope of what we deliver for them. So that's kind of the way that we can work with the three leadership types that are really out there. And what we bring to the table as leaders is things like market intelligence. I mentioned this a little bit earlier, but we work with a ton of different customers, oftentimes within their vertical.

[00:16:20] And one of the biggest values that we can bring to the table is that outside perspective. Hey, we understand both the industry trends, what the competitive landscape are, what the tool sets that are being used in your ecosystem. And we can bring that knowledge of how that's been executed elsewhere without telling secrets, but giving an understanding of how that was really implemented and bring that right into their own organization.

[00:16:45] So don't underscore the fact that you are so embedded across different organizations as that is an advantage for you bringing leadership wise. And it's one of your special skills that you should gain. The other thing is we can help them with cybersecurity awareness. Obviously, our organizations are on top of all this. Even if you are not as the VCIO on top of it yourself, before you go out to a QBR, just go talk to the team that supports them.

[00:17:10] And I'm sure they'll give you an understanding of where some of the cybersecurity gaps live for that customer. And you'll be able to kind of take that to the streets as well. AI and automation insight. Think about how fast we feel as technologists AI is moving. And we understand this stuff at a much higher level than our customers ever will, but yet we can be overwhelmed at times. So think about where they sit as well.

[00:17:34] And when we go in to work with these customers, you know, they're going to be looking sometimes for that big bang project that's going to solve a lot of things. And what we might need to convey to them in those scenarios is, hey, this isn't one big project that's going to be AI-based that's going to change the world. It's going to be a series of small steps with different people in your different organizations, helping them automate and become more efficient.

[00:17:58] And then building this information in a way that we ultimately centralize it, can look at it a little bit deeper, and then make business decisions. And as you start doing that, it becomes kind of the sum of the parts, right? The more of these things that we do along the way, the greater the impact is going to be long term. And that gives us really an opportunity to continue embedding ourselves into their process as things are getting turned up. Finally, you know, strategic structure, it goes without saying.

[00:18:25] And really, that's kind of been the underpinning of this entire conversation today. The more we can understand what they're trying to achieve, the more strategic we can be about positioning projects, understanding where they're going to impact risk, and then ultimately getting the yes that we're looking for on our side of the occasion. And that comes from doing all these little steps. To recap, learning about them in the first three months, understanding what they need to do, getting deeper within their organization,

[00:18:55] learning how they actually operate, and then ultimately guiding them in a way where they feel more empowered to make their decisions. And if we do this each step of the way, my God, the leadership component or where you stand within that business just becomes second nature. You are part of their business, and they are going to reach you at all times. So, you know, really follow that roadmap, and you should have tons of success with your organizations that you work with.

[00:19:23] You know, ultimately, when it really comes down to this in closing, it's the balance of external leadership we're looking for. We want to be influential without being authoritative, meaning we want to shape decisions and earn trust. But we're not looking for positional power. We're not part of your organization. The minute you get involved in their office politics, you've gone too far. So make sure if you feel that happening, that you're stepping back. Don't choose sides, right?

[00:19:50] You want to be embedded without being controlling. Yes, we want to become part of the fabric of their business, but we don't want to be dictating to them. They need to feel that they're owning the decision, that they're taking the wheel, and they're driving that car that we're providing to them. And then be accountable to the outcomes, but do not own the decisions.

[00:20:12] I've heard some MSPs, believe it or not, come to me and say, yeah, they just tell us what the budget is for the year and how we spend it is up to us. Again, talk to your lawyers about that, but you don't want to own the decision about go or no go. But you do want to be responsible for the outcomes that come out of those projects that get delivered. And if they're not meeting the need that we originally set forth on, understanding where that gap might be and how we can get there.

[00:20:40] Understanding where the interpretation myths might have been. Own that there might have been one. Own that you might have been the person that missed in delivering the information specifically. But then take ownership of what the after effect can be. The more you care deeply about the results of their organization and respecting the authority that they have, the better you are going to be as a leader with each one of those organizations.

[00:21:06] So hopefully this gives you a little bit of kind of a blueprint that you could take to the streets, whether you're a VCIO, VCSO, or the new virtual chief AI officer role. Well, you know, what I hope you're going to take away from this is I've got to take steps to become a leader. I've got to see where I fit in each organization because leadership is not going to look the same, you know, from client to client.

[00:21:30] And then the things if I'm feeling a little imposter syndrome is, hey, I work with a multitude of clients. This gives me the authority to better understand more than others what you need to do, Mr. Customer, and then be able to convey that strongly. If you agree or disagree with me, just let me know down in the comments. You know, obviously, you guys know we post this to YouTube or go anywhere where we have our that you could download your podcast. And we certainly want to hear from you.

[00:21:57] If you've had any success being an external leader and you want to talk about it, reach out to me as well. We're always looking for new people to tell new stories here on MSP Business School. So we'd love to have you. I want to thank you all for joining me again this week, and we'll see you again next Tuesday.