ProductiviTree: Cultivating Efficiency, Harvesting Joy

The Truth About Cross-Functional Work

• Santiago Tacoronte • Season 2 • Episode 55

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Today’s guest has been at the heart of transformation for over 35 years in IT, including nearly three decades at Microsoft, where he now leads Customer Success for AI, Cybersecurity, and Leadership across some of the world’s largest Retail and CPG enterprises. He’s a Microsoft GM, Industry CISO, LinkedIn Top Voice, keynote speaker, and former Vice Mayor who has led mission-critical programs like Navy Flank Speed and USAF CHES, all while championing one core belief: technology doesn’t transform organizations, leaders do. Get ready for a conversation on leadership, cross-functional impact, and clarity in chaos with Nick Palomba

Nick Palomba spent 29 years at Microsoft coordinating teams across functions, time zones, and government agencies. He shares why most cross-functional work fails, when silos are actually smart, and how to get results without the corporate collaboration circus.

Speaker Links

https://www.linkedin.com/newsletters/nick-palomba-s-newsletter-7164304949038833664/

Recorded Date and Location

Date: 05/02/2026

Guest location: Greater Tampa Bay Area


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Nick Palomba welcome to ProductiviTree Thank you so much for having me. I'm excited to talk today. Nick, you lead hundreds of experts across cybersecurity, AI, cloud infrastructure, and every type of work at Microsoft. But what was that made you realize that breaking down silos and cross-functional work was a non-negotiable for your success? Yeah, it's a great question because there's a lot of people involved in projects sometimes with from all different areas from the business, from vendors potentially, from, you know, internal separate teams. think the biggest thing that I realized is until we actually have a defined mission statement goal, however you want to, you know, classify it. And then when we ask the question. does this really, the work that you're talking about doing changing or the issue we're having, does it really move forward the ultimate goal? And if we don't have an answer of yes to that, then let's table it for now. I don't wanna take us off track because timelines are short, things are expensive to do, so I wanna get the most efficiency as quickly as possible. During COVID-19, you led mission critical deployments like the Navy, Flank Speed and USF uh Shess. So you're coordinating military branches, government agencies, Microsoft divisions. What's the first thing that breaks down in cross-functional teams? So yeah, that was a big team and there's a lot of people from Microsoft uh leading that project because it was just such a huge initiative and from the military side as well because of the time that we needed to do something in. I think that... What we found there, and I think the military is a little unique in this place, it's a very top-down leadership perspective, right? We have orders are orders, and that helps you kind of define the message. I think the challenge comes into place when uh people want something that's different than what we're building, because we had to build something, we have to build something for millions and millions of users, and one want or desire from a place could really take you track and I think that's the thing that we really learned is we have to limit the signal to noise ratio on the noise that's coming up and make sure the signals that we're working on are going to be directly for, in this case, for people to get online from a virtual environment. You spent 29 years at Microsoft in many... coming up on 30. Hi, 30 is coming. um You've been as a deputy CTO, you've led server security now and customer success. Do you think that cross-functional leadership requires you to sacrifice deep expertise? Yeah, especially these days in the change that we're seeing in environment, you know, the technical environment, AI, the changes that we're seeing. I don't feel like I could be an expert in everything. um And I think people will fail if they think they could be an expert in everything because I read a lot. But then when I go listen to Satya, I'm like, wow, I don't know anything about our products because he is so deep on so many products. And I think you have to come to that realization of, need Joe, I need Mary, I need somebody else on the team that's an expert in that area to supplement what I need to make this project successful. we have a saying inside of Microsoft is become a learn it all, not a know it all. And I think that's one of the things that we kind of think about. Your leadership philosophy is the three Fs, firm, fair, and fun. When you're coordinating across sales, engineering, security, and customer success teams, which F gets sacrificed the first when the pressure hits? fun for sure. Yeah, fun goes out the window. The stress comes in. um Firm has to stay in place because that is the goal. We know what the goal is, we know what the outcome that the customer needs or the situation needs. So we've gotta remain pretty steadfast on the firm part. Fair, I'd say equitable in uh who we're giving all the action items to. That's one of those lines. Some people have more than other people and some people are responsible for more. uh I try to keep things fun because we're working on these things 40, 50, 60 hours a week and if you don't have an opportunity just to laugh a little or enjoy the people you're working with it makes that grind so much harder but I would say fun unfortunately is the one that goes out first. You say that technology doesn't transform organizations, leaders do. When you have multiple leaders on a cross-functional initiative, who really owns the outcome? Well. You know, it's a great question because ultimately you say, you know, there's one person on the top and sometimes there's not, right? Sometimes there is a business owner that has the project and it's going to change or transform the business. And there's a business out looking around we're trying to get to. And then you have a technology leader who has different, you know, a different lens on the situation. So really what it comes down to and kind of what I try to do is make sure that executive level people that are on that team, you know, the one, two, three leaders who are over there, we meet regularly to stay on the same page and we talk it out and we kind of have that hard discussion between us and then when we hit the table and we walk out the door, we're all saying the same things. It's okay to disagree. It's okay to have constructive criticism. I I think it's great and I want to hear all perspectives, but at some point we have to hit the table and say, okay, here's the decision and this is what we're going to go do. Whether I agree with it 100 % As long as I'm, you know, 80 % there, that's fine. I'll withhold my comments. You've coordinated cybersecurity transformations with CIOs, CISOs, CTOs, boards. What is the most underrated communication practice you use that keeps cross-functional teams from start blaming each other? ah It's a hard one, but it kind of goes back to the fair conversation and the three F's. In the fair, what I like to call that is we need to hear all perspectives, right? failures happen and it's okay. If something breaks in the system occasionally and we have to go fix it. It's better to be the person who calls out something happened, explain what happened and how you're gonna remediate it, versus trying to, I don't know, talk around it, not take responsibility. As long as you're willing to take responsibility for that piece that broke, I think that credibility of you being honest and truthful helps the overall project. And hopefully we only have that failure one time, we learn from it and we never do it again. Nick, cross-functional, one on meetings. Cross-functional meetings can be a time black hole. How do you prevent this from happening? How do you maximize time from people when you have a meeting with 25 person, with different departments, some of them has to be there, some doesn't. What's your rule? Yeah, it is a great question. And I'm one of those people who hates to have a meeting beforehand to have the meeting. So, you you go into a prep meeting to have the meeting. just, meetings could suck the life out of you and project timelines and so forth. So. uh I mean, it's, you've got to have a crystal clear system in place. How are we going to talk about the project? What's the timeframe we're going to give each person or each situation? If you require more in this meeting, then we should have a something in the system that says, okay, today we're not going to talk as much about security because there's not much changing, but we need to talk a little bit more about AI. So you have to have a system that's flexible to give people the stage for long enough. uh But I also started to use a little feature in Teams, which is a clock that goes across the top of the meeting and you put in simply like five minutes. Well, here's your five minutes and you can see you're coming up on red. And it doesn't mean we're cutting you off or you're not important, but we have a lot of pieces that are important and you have to fit inside that timeframe. Naked I've started uses this, the feature, the time, the time feature in teams and it's a game changer. Somewhat magically people stick to the points and when the time is starting to become red, people hurry up, wrap up and the next topic is in. Well done on adding these two teams. Really well done. Well, uh my boss and my peers might say that we started using this feature because of me, uh possibly, because I might go over my timeframes. But it's a great, we've actually kind of made it fun. if you go over your time, you have to put a uh few dollars into the kitty. And then at the end, we give all that money to a charity. So if you go over, you know, you have to uh throw something into that pot, which has kind of helped us. stay on track a little bit better. Lack of ownership, it's a productivity killer. We know that. What do you do when you go into a meeting? There are five departments there. There is a topic on the table and everybody starts saying, this is not my team. This is not my department. We don't have bandwidth. This is not for me. You know, there's also times that you have to reevaluate to say, is this project important? Because if we have all of these blockers in the organization, somebody, somewhere this project started for some particular reason, whether it be from the business, from leadership, from the CIO, whatever it came from. But if we start to see that there's so many blockers to something, we have to evaluate like, is this project really business critical right now if we don't have buy-in from all these groups? Now, if it's something we need to get done, then we have to talk to each individual group separately. And that's kind of what I like to do is talk to team one about the project's super critical to our business. What can you give us? What can you not give us? And try to fit. all of those boundaries into the overall meeting, but then also challenge these teams, right? We get challenged all the time. Yes, this is business critical. I know you're super busy, but we have to get this done. What could we do or what could we deprioritize in our current workload that will take priority? So it's really just... getting to the time, figuring out how we can fit this in time. The other thing I'd say, which is a little newer to our work stream, and I don't think we're all really good at it yet, and I think we'll get better, but where can AI help? Where can an agent come in and do some of this work or oh remedial tasks that have to get done? Use the tools that you have oh to create space and opportunity. When you're running a cross-functional project, Naturally, different teams will have different metrics. Sales might be chasing their sales number, engineering, another thing, and security will have different performance metric. How do you align a common goal, incentive, you avoid that everyone is thinking about their own camp and don't care about the greater good of the initiative? It's a really great question and you know, as you add complexity of partner or, you know, company like Microsoft coming to your project, we have our, you know, specific things that we want to get out of the project. You have things that you want to get out and other organizations have, you know, their priorities and their metrics. I think it's important to talk about those. I think it's important to set the stage upfront and know what people's motivations are. If I know that sales has a motivation around X, that's going to help me define the project a little better. If I know IT has a particular uh you know, critical metric in this. If we could talk about all of those openly and be honest with each other, like, hey, I'm doing really poorly and this is where I'm going to be focusing my time, so if this project doesn't help me, I may not be able to be involved or be involved to the point that you need. Those are important things to know upfront and be honest, right? I mean, I think the more you're open and honest with each other, the better outcome you're going to get. Nick, you were vice mayor of Indian Rocks Beach. I hope I this right. Now, managing governance and community stakeholders seems to be quite a different thing than managing businesses. What lesson would you take from local government or government work into the corporate boardroom? Wow, it's super interesting, especially in local government because you could tell right away by who's attending the meeting. what the impact of what you're talking about is gonna be. let's just say hypothetically, something was gonna happen on street one, two, and three, we were doing some sort of construction, or we're gonna do some project, the people from one, two, three would enter that meeting and be very boisterous. Now you have the people who come to every meeting and they have the impact on the meeting and they're informed and they wanna be part of it and that's great. So I would say you could learn a lot by who comes to your meeting and who's prepared of what priority they have on that. It's also probably was a harder job than my corporate career because Everywhere you go, it was 5,000, 6,000 people. If my wife and I would go out to dinner, we would get approached. If I'm walking my dog down the street, somebody would come out of their house to talk to you. So you're constantly getting feedback. You're constantly hearing, mostly bad. You don't hear the good as often, but mostly the challenges that somebody has. In the corporate world, sometimes when the meeting's over, the meeting's over. But I'd say you could tell a lot by the meeting or the priority by who's showing up for it, who's showing up. prepared. Speaking of that, a lot of people say they want collaboration, but a lot of people what they want is credit. How do you identify who's actually there to really solve the problem versus who's there to get a pat on the back? Yeah, this is something we talk about a lot is if you're going to be on a team, it's the expectation that we set up front with people. You're not coming to the meeting just to come to the meeting. You have a purpose for being there. You have either an action or a responsibility. And if you're on a sub team from that, whoever's leading that sub team. part of leading that team is to give feedback on each one of the people who is in that team. So if you come and you're going to be a part of it, you know up front from our established leadership principles, you are going to have to do X, Y, or Z, or we're not going to have you in this team. mentioned AI a couple of times. It's AI making cross-functional collaboration easier. I would say Teams in that collaboration platform, like you, I've been in collaboration for, you know, I was around when we first started the BPOS Office 365 world, and I've been in collaboration a long time. I would say the Teams platform. gives us a great place to collaborate. Now, the AI that's sitting in there, the uh ability to use Copilot to summarize and pull agenda topics and do all of those types of things, uh that's where I think AI is gonna shine in cross-functional team output. you work in CyberSec and security teams have a reputation for being the department of NO. um When cross-functional collaboration means compromising security, where do you draw the line? Where do you say, well, that's great. That's great that the project needs this and that, but we're not going to cross that line. Yeah, so the philosophy of Microsoft is Secure first, secure by design. And so when we start these projects and initiatives, everybody in that room should have a security hat on or thinking about security or what data are we publishing or where are we getting data? that going to compromise something? I think it's important to have it upfront, but I think it's important for security also, security teams to not be the department of no, we have to look for a way to make this work instead of just saying it won't work. And I think it's a transition, it's a transition for a lot of us, right? We're just used to saying, no, this is the way it works and we're not gonna do something here. But tools and uh technology have changed. So we have a little more ability now to be a department who could say, no, but what if we do it this way? no, but how if we treat the data this way, would that still work for you? So I think it's incumbent upon us to insecurity to also be creative as we go forward. Because we're solving business challenges. We're solving things that are impactful to our company and our people. We can't just say no by default. Some productivity experts argue that cross-functional teams slow down decision-making. There are too many cooks in the kitchen, a lot of alignment. When it's actually smarter to keep a project siloed with one accountable owner. uh I think, I mean, I personally think there should always be a accountable owner, DRI, direct responsible individual. There should be somebody in that seat at all times. uh I think from a silo perspective, from planning and envisioning a project, it's okay to kind of think about it that way and kind of get everything on paper and whiteboard and kind of get your vision mapped out. But once you have that vision and you're gonna go from the envisioning phase into an implementation phase or a design phase, at that point you could no longer stay in that silo because it's gonna have impact to too many other organizations at that point. I think people don't think about are in finance and how those things could be impacted and I don't want to slow it down but I want to make sure I'm crossing t's and dotting i's all the way through that I'm not going to impact something. goal is to leave something better than I found it. With all your experience in cross-functional projects and Nick, have you faced a time where you said, well, this is not working, there are too many layers to this, we need to simplify and restart? When do you decide that it's time for a change? I think there's a couple places I would say when people are spending too much time trying to solve problems that... shouldn't take as much. So like, let me say this a different way. If we're in a churn phase for a long period of time and we're not progressing towards what the ultimate goal is, because everybody is churning on a problem or a solution or potential or this doesn't impact my area, this impacts my area, there's a point in time right there where you have to call timeout and say, okay, it's time to restart what we're doing here. Also, business climates could make changes, you know, if earnings come out and they weren't how they we expected and this project becomes not as important or if we're looking at technology and there's technology changes that could really redefine this. If we're trying to build something and all of a sudden, uh agent comes out that could do all this work, then we need to stop and reevaluate. I think when churn is something I try to avoid too much of, all of the signal to noise, if I'm hearing more noise than signal, but also keeping an eye on what's happening in the industry and the market so that I know that a technology potentially could help me solve this problem and we don't need to spend as much time on it. Nick, I'm gonna throw you a curve ball. All right, let's go. Let me sit up for this one. Leadership gaps are cited as a major reason cross-functional work fails. What type of leadership destroys cross-functional productivity? I think we talked about it earlier when people are looking to take credit for something versus actually trying to solve a problem. uh think ego and personality could kill a project faster than budget or technology. And another one. Just keep going, wow, curve ball. hybrid work. Hybrid work is at default in 2026 in most uh companies. Does physical proximity still matter for cross-functional collaboration? Or we have gone through this and what we're doing today, you and I through a call, it's okay. Yeah, I'm a fan of hybrid work. I've been doing it before pre-COVID. I've worked from home or from one of our smaller offices for a very long time. I don't think there is a... I don't think there's a time when people getting together. still won't be more productive. Like when we're in a room and we're all together, I think sometimes magic happens because you're not distracted by some of the things that are going on in your house. A FedEx package gets delivered, my dogs start barking or something of that nature, right? mean, kids, there's, there's a lot of distractions when you're home and it takes away from that ability. but when I'm working on something and when I'm heads down, I also find that there's distractions in the office where people stop by. and say hello that you haven't seen in a while or hey we're gonna order lunch from so-and-so or whatever the interruption is I find that for me personally I could dig into something and go harder when I'm in my comfort space here at home that I've created for myself. Let's do some rapid fire questions. And we're in 30 seconds or less. Number one, cross-functional meeting or solo deep work? Which one drives more productivity? Cross-functional work, I think, because deep siloed work, uh you're gonna get things done, but I think you're gonna change more when you're together. There's a better opportunity to have change for a positive habit. Number two, if you had to kill one collaboration tool, I'm not talking about the software, okay? A tool, tomorrow that wastes most time, what would it be? Ugh. I'm gonna say something that's probably gonna be unpopular at Microsoft, but I'll say email. I think email is something that kills more time than picking up the phone and setting up a call, doing video with each other so you can see tone and inflection and those types of things. I think email is very impersonal and you just don't get that tone or understand if a person's upset. positive. It just it's a harder medium in my opinion. And you're talking to somebody who's been doing email migrations at Microsoft for a long time. uh I'm just curious. want to throw another one. What about chats, teams? Do you find them better than emails? I do because I can answer things quickly. I could get through a lot more chats than I can in emails. uh And I think my personality comes through better on chat because you have emoticons and other things where you can add something so people kind of capture your tone a little bit better. uh So I'm a chat over email person any day of the week. Number three, what's the fastest way to spot a fake cross-functional leader versus someone who actually gets results? the preparation that they do or don't do for that meeting. If somebody continuously comes in unprepared, late, and doesn't know where we're currently at and what the major problems are, yeah, I get really frustrated by that. 4. Should individual performance reviews exist in cross-functional teams? Absolutely, yes. If a person is on a team, there should be feedback that's provided on their performance in that team, absolutely. Fill in the blank, the death of every cross-functional project I have seen is... Of every, that's a big word, any, uh the biggest challenges are time and budget. One of those two things uh causes challenges. So we aren't delivering on time or the project is going over budget. Those are the two things that really concern me about Teams. Nick, let's give some practical advice to our listeners. We have a large audience of people that work in knowledge work and knowledge jobs. If someone is listening to us today and they're struggling with cross-functional because they cannot find who's the owner, they're lost. They're like, my God, there's so many people. I don't know what this guy is doing. I don't know what this girl is doing. What is your advice to get there? head together to get the life together and come back and add value in that environment. Don't be afraid to ask. Ask that question of the people that are leading the project. uh I'm struggling a little bit to understand. I know I can bring value to this project, but I don't understand where I fit or how I fit into this project. It's okay to ask because... that will take away the stress it's causing you or the upset it's causing you and the person who or people that are in charge of the project should be able to redirect you because they brought you on that project or you were put on that project for a reason. A leader thought you had the skill set or you were going to develop this skill set so somebody believes in you. and now you just need to get a little bit of clarity. It's okay to ask. I mean, I do it all the time. I ask questions and be vulnerable. It's okay. um Nick, how can people get in touch with you? I know you have a newsletter which a ton of thought leadership I discovered it a month ago and I immediately subscribed. How is it called? How can people subscribe? Yeah, you can find it on my LinkedIn and it's called the leadership lens. uh I like to do photography as well. So it just kind of combined two things for me, but subscribe to it there. And again, if you've read the last few, what I try to do is keep it fun, keep it light, but put in, you know, some real world things that are happening at the time. I think my last one was Tom Brady, maybe the best quarterback of all time. We could argue, had a little Superbowl on the mind, but he talked about all of the things that he failed at and how he had to work to get to where he is. So I try to keep it fun and light and you could find me on LinkedIn. I do my best to answer people's questions and chat, but it gets a little overwhelming at times. And if I don't get to that day you sent it, usually weekends are my time to do as much answering as possible, but I try my best. Nick, who are you rooting for this Sunday on the big game? I'm more of a college football fan. um So I think I will probably be rooting for the Seahawks just because I lived in Seattle for a while and used to go to some games. Even though I'm from New England, I was more of a New York sports fan than a Boston sports fan. So I think it'll be the Seahawks. Well, let the best one win and take. game. Nobody gets hurt and everybody, you know, that's everybody leaves and uh the game isn't decided by the referees. How about that? Nick, thank you so much for this insightful conversation. I'm taking a couple of things away today. The number one is that the best recipe for cross-functional work is clarity, trying to be clear on what you're trying to achieve. And the second one is that... It's okay to ask. You just said it. Sometimes you tend to absorb a lot of things for yourself and you know, you get all these troubles in your head. my God. What, what did he mean? What does this other team wants? And as I said to many of my team members, the answer is just one team's message away. Nick Palomba, thank you so much for being with us today. Good luck on the big game and a lot of success with whatever you do. You as well, thank you so much for having me. honored and company to company, you're a great business partner and you guys work really hard and it's always enjoyable to work with you, your team, your company. So thank you for being a great customer as well and thanks for having me.