Timm Chiusano on AI and “Winning the Week”

MOLLY WOOD: Timm is authentic and relatable and has become a prominent “work influencer” with over a million followers on TikTok. His balanced, mindful approach to work and life has particularly resonated with Gen Z, who of course are engaged in an intense conversation about the future of work on social media. In fact, Chiusano recently left corporate life to be a full-time content creator. He’ll talk today about that journey, and why he wants to help everyone do their best work by being the best version of themselves. Chiusano also has some advice about how to be a great manager at a time of rapid technological and societal change, how younger generations are thinking about careers and productivity, and what it means to influence the work world through different social media platforms. Here’s our conversation. 

[Music]  

MOLLY WOOD: Timm, thanks so much for coming on WorkLab.  

TIMM CHIUSANO: Thank you so much for having me. What a fun conversation we’re about to have. I can already feel it.  

MOLLY WOOD: We gave this kind of nutshell overview of your career, but talk about this recent big pivot that you’ve made, this huge move, leaving corporate life and going on your own.   

TIMM CHIUSANO: The funny part about how it was teed up is, as you were saying, I’m like, that sounds like the most boring TikTok account [Laughter], because you think about TikTok and what people are there for, and it doesn’t make sense. But the jump has really been about fully understanding an audience and the value that can be provided to the audience. That’s more important than whoever I am and whatever I bring to the table. It’s an understanding of who is out there, what could they use, want, need, etc. And then also having an understanding and comfort in my own value. Like, what does my resume actually bring to a table and how valuable might that be? And mixing that all up into a ball and saying, let’s go get it. And now we’re here. And the exciting part is feeling comfortable to talk about things now in a way—not in regards to like, Oh, let me tell you about the people that I used to work for or work with. I will tell you those stories, and I will speak glowingly of just about all of it, but I’ll also say, here are the things that could be fixed, and here are the places where I think people, leaders, companies, departments can benefit from somebody not being in the muck and having a bit more comfort to say, I think that your weeks could be structured differently and here’s how I would do it if I was running your company. Food for thought, but I’m just trying to lend value and fulfill my own purpose too.   

MOLLY WOOD: I want to ask you about technology and incorporating technology and things like AI into the processes that you talk about every day. You have talked about how leaders should not treat AI or other new technologies as, like, a general contractor obsessed with a hammer. How can leaders use that kind of specificity, that observation, that listening to figure out the best place to apply these new tools?   

TIMM CHIUSANO: The reason why I tell people, Don’t become obsessed with it like it’s a screwdriver that you never saw before and all of a sudden you’re running around your house trying to fix everything with the screwdriver. Because it is AI, because it’s not a human being; your people are what got you to where you are. You yourself as the leader, as the head of a company, are empowering people to bring you the best ideas and to help move your business forward. And you probably have a lot of those yourself. If you get too distracted on, How does this thing help me get there, versus Where do I want to go, I think that that’s just a very specific and necessary element for consideration so that it’s less about taking that thing and then figuring out where to go apply it to because, quick, everybody’s in an arms race to use this thing. Yes, I understand that that is happening and that is real. But I think those that are going to have the best long-term outcomes with AI in mind are going to be those that continue to focus on, What are the biggest ideas based off of where your brain, your team’s brain, where your consumers, your customers, where they are going, where they don’t know where they want to go yet, and then utilizing AI to help you get there versus trying to force it to be the leader in the conversation.  

MOLLY WOOD: Yeah, like outcomes. You said that word, and it’s a big theme of yours, and it sounds like what you’re saying is in some ways, start at the end, figure out what you want to achieve, and then how the tools get you there.   

TIMM CHIUSANO: Totally. I think it’s, at the very least, that has to be part of what’s on the table to unlock the biggest and best in regards to what the future may hold. Otherwise, as empowering as AI can be, I truly believe you are limiting yourself by focusing on that as a driver versus something that will help you get to where you want to go based off of how you see your landscape changing, your consumer behavior changing, your people’s behavior changing, and then utilizing it truly as an enabler versus, like, this is what’s actually behind the steering wheel.  

MOLLY WOOD: Right. The way Microsoft thinks about it is: start with a business problem and then apply AI to it, and that’s how you get the most value out of AI. I would love to get your thoughts on the creativity part of the technology conversation before we move on. I mean, that’s obviously a huge question—if you can get things off your plate, you can be more creative. I wonder where you fall on that concept.   

TIMM CHIUSANO: This is coming from somebody that shoots everything on their phone. I have literally edited 2,000-ish short-form pieces of content with my head tilted to the side because I have to rotate it into 16x9, edit it that way...  

MOLLY WOOD: This feels very anti-productivity of you. I feel like we can do better for you here. [Laughs]  

TIMM CHIUSANO: The beauty is, I was so efficient with that process that it worked, right? And that’s all that really matters. It’s, What does good look like at the end of the day? What good looked like was me being able to get a piece of content out on a consistent basis that I had a feeling was going to be helpful or useful or fun and engaging in some capacity. And that meant going with this process. So from a technology perspective, how do I use it to cut down longform? That’s probably the most helpful place that I’ve actually used technology—utilizing it to say, Hey, what do you think the best 60-second clips from that last 20 minutes were? It certainly helps me when it’s like, okay, here’s five things to choose from.  

MOLLY WOOD: So I want to talk to you a little bit about who your audience is and what you think they want. Like you said, this isn’t the typical TikTok content. You’re making content that says, here’s how to approach work. You might not always love it, but if you’re open you’ll find unexpected things that you really appreciate. What do you think your audience wants and needs from you? 

TIMM CHIUSANO: It varies a little bit by platform, and I’ll start with TikTok because that’s where this all began. There, I think the audience really wants a reflection that everything is going to be okay. Simple. They want to know that there are relationships out there where you can truly be in love, be encouraged, have things reasonably balanced in their opinion based off of what they see, feel like a family life in a more progressive environment is not something that is otherworldly; meaning, you can have a kid and you can still live in a city, or you can have something that doesn’t look like what the cookie-cutter approach might be. It’s just a comfort level that that combined with a career that they may have a passion for, be driven by, and that all of these things can work concurrently. So I think the TikTok audience really just wants reassurance that everything’s going to be okay, and that growing up is not going to be the scariest or most soul-sucking thing that they’ve ever experienced. I think on Instagram, it’s a bit more value-driven relative to specific insights and things that can be takeaways, so to speak. It’s a slightly older audience. I think that there’s an expectation that there will be—it’s still the same kind of core need and desire, but I think that there’s an extra level of, okay, well, but then what...  

MOLLY WOOD: So like more actionable—less feeling, more action.   

TIMM CHIUSANO: Exactly. LinkedIn gets into a whole other ball of wax, and it’s so fascinating there. For a while I was getting—and I still get this ridiculous amount of DMs. I remember at first being like, Oh, wait a minute. I’m getting a ton of entry-level and mid-level people that are reaching out—where are some of my counterparts? Where are some of the other executives out there, et cetera. And then I realized what a gift it was to be getting that audience and the questions that they have. And I actually took the last 20, 30 DMs and put them into ChatGPT just this weekend and asked for themes. I’m like, what are they asking for? What’s my best approach to answer, because I can’t answer all of these one-on-one requests, like, Hey, I’m in this industry. This is my situation. What would you do? It’s a lot of work to go through and answer even just a hundred of those on a one-off basis. So, basically, the number one theme from my LinkedIn DMs was pivoting, transitioning, adapting from an overall career perspective, whether that’s because somebody was laid off or there was change at a company or they want to get in front of change, et cetera. That was eye-opening. So that clarity that the technology can bring you based off of—in a world of so much volume from a communication perspective, that was huge. I believe at the highest level and from the most passive perspective, the audience just wants a reassurance that growing up is not going to be the scariest and worst thing ever. And then I think at a deeper level, and the more specific you get into the platforms and what somebody can take away from it. In some cases they want, No, here’s going to be the playbook or here’s something actionable or I’m going to save this to come back to it, because when I’m a manager or when I have a kid, or when I’m ready to go ask for that next promotion, here is the playbook that I’m going to take because I know this person, I trust them. And therefore, I’m that much more comfortable taking their advice and applying it to these places. 

MOLLY WOOD: A lot of companies are thinking about and trying to figure out their approach to social. Who are they trying to reach? What are they trying to say? In your experience, what does a successful message look like, and what does it do? 

TIMM CHIUSANO: These are the larger questions that these companies have. And if you do look at it the right way, and especially when you start to engage with, borrow from, and should be staffing with people that have been born and raised in this space and can also have the broader mindset of, Well, what does good look like or being smart enough to ask—what does good look like after a company has engaged in this space and people engage with them in that space—why are you there in the first place? What is the value in it for the end user? And then using it holistically, because there should be this cycle of, What are you creating as a company or as a person based off of what you bring to the table value-wise, but then how do you get it out into the world in the most easy-to-digest ways based on the platforms that are available. And it’s so interesting where you’re like, I have this really big idea. But do I go make a podcast about it? Do I go write a book about it? Do I go make a YouTube about it? Do I try to chunk it out into 18 60-second episodes? That can be the fun in it as well, if you like those types of puzzles.  

MOLLY WOOD: I want to ask you about teams. The job that you just left, I believe you said you were managing 240, you had a 240-person team. How do you think about structuring teams with values and outcomes in mind? And also, how do you do that?   

TIMM CHIUSANO: It’s so much fun. I say that with so much sincerity. It is so much fun to figure that out. What does the end user really need, right? I’ve seen in a lot of cases the structure be built around things. It’s like, no, this is what we need to do for that, for this other thing that’s our own business purpose, where it’s like, cool, but that’s not what they want, so that’s never going to work. Or that’s going to hinder the rest of your business because you’re trying to force this team to do this thing this way because of their own interests, because of what their department lead says, et cetera. Clarity of outcome. Obviously clarity of role, but clarity of role in a way that truly pulls from what a reasonable skill set could or should be from a traditional perspective. How do you set people up so that they can look at as many days as humanly possible and say today was a good day? Because if you’re setting things up in a structural way where your team is actually saying that on a consistent basis they weren’t bored—because they’re not going to say that if they’re like, cool, I messed around on the internet all day—they’re not overly stressed, they feel like they are fulfilling their own purpose and delivering value back to a company, they feel safe and secure in their role, and they’re clear on what the outcome is. I think a lot of teams and structures—and maybe it’s the exact right structure. Maybe it’s the exact right overall ethos that’s applied to that department relative to the rest of the company, but they have no idea what the impact is that they’re having on the business. Or they only see it from their own lens of, Cool, we’re sales support and therefore we did 500 projects last week. Isn’t that great? What percentage of projects was that? Is that a good percentage of projects? How much revenue? Those types of things. So can they say that they had a good day on a consistent basis? And a huge part of that is clarity towards the larger business objectives. How do they tie in and see those things? And then honestly, and I’m not saying this in a flippant way but these are things I need to be more comfortable with, I’ve done back-of-the-napkin org chart building for substantial teams on subway rides after I’ve taken the time to think about, Oh, if we’re going to do 20,000 projects like this, and these other variables in mind, this is what we’re doing. So I think if you can take the time to really digest it, have that focus on, I have to have my people say that today was a good day as often as humanly possible, and then ties back to the larger objectives, then you can get to a place where you’re like, Cool, we’re now like a pit stop crew. Everybody has clarity of roles, responsibilities. They can repeat the process consistently, and they feel really good seeing the time get shorter, the process get better, the car get out of the pits quicker, et cetera. And there’s fulfillment in that as well.   

MOLLY WOOD: The other maxim of yours that I want to ask about is “winning the week,” which I think is really powerful as a personal concept, but again, as a leadership concept. What does it take to get managers to start thinking about that for the people who work for them?  

TIMM CHIUSANO: This could help solve for so much in corporate America very quickly. Every company has annual goals. Therefore, they have quarterly goals. What are their weekly goals? Not a lot of companies have weekly goals. Maybe there’s weekly metrics, but how much transparency are you creating between the work that is happening on a week-to-week basis and how that is rolling all the way up to the top of your company goals? There’s a very specific structure as to how each and every day should operate based off of connecting the dots between weekly and annual. I mean, in my head, it started out as, If I can just get my direct reports on the same page with what our weekly to-dos are, and if we keep that in focus with what our annual goals are, we’ve got a chance. Because there was a lot that we faced along the way where people are like, Your department doesn’t make sense, or I don’t like the way that it’s structured, or you slow things down right before we’re able to get revenue in the door. So our ability to say, Okay, cool, it’s Monday morning. How are we going to win this week? If we’re looking to get to X amount of core supported on an annual basis, what are we doing this week that’s going to help us get there? And that could include things like, Part of winning this week is, everybody take a look at what your local data says relative to the percentage of accounts that you’re engaged with, and getting crystal clarity on specific things that are actionable and reasonable on an actual week-to-week basis and then implementing them. This created clarity from, What do leaders really care about and what are we asking the team to do? How does it tie back to what your own annual performance goals were? And you’d be surprised—but leadership has to be the one driving this, or they have to at least set the standard that this is something that we want to see happen. Because otherwise, everybody’s calendar is just this legacy—oh, I have these team meetings that I just inherited two years ago. I have no idea why they picked Tuesday at 4 p.m., but that’s the way that it’s always been. You can have every single day fulfill a specific purpose that creates more clarity around what needs to happen. How are you going to get it done? What does good look like at the end of that day? But not in a way that you feel like a robot, but you feel like it’s just created more focus and breathing room in your brain versus, I’m just kind of holding on for dear life on a week-to-week basis—oh, goal check in. Oh, cool. We’re ahead. We’re short, whatever it is. You can actually almost create a weekly feedback loop. Some of this came to mind when I was studying SCRUM and the iterative process. And what I’m describing is not just for that, like, this works with waterfall, this works with agile, this works with SCRUM management. It’s about simplifying things. So I think winning the week helps simplify—creates clarity, creates more purpose and structure, and can make it more fun too. Because on top of all those things, if you can gamify some of these actions as well, you can get large groups of people in very, very, very corporate environments to be like, Cool, this is fun, and I actually love my job. And that clarity gives you more space to have fun with the details of it, versus just like trying to layer that on top of a hot mess and having people feel like it’s not truly genuine or it’s just forced in there because everything else is such a mess—cool, now we need pizza lunch Wednesdays, once in a blue moon, because somebody was freaking out about culture and was like, We’d better do this and give them free food or else it’s really going to get hairy.  

MOLLY WOOD: Timm, it is really corporate America’s loss that you have gone off to be a TikTok superstar because you sound like a great manager.   

TIMM CHIUSANO: [Laughs] It was my favorite thing to do. I genuinely loved it, and I would say it’s actually—hopefully it becomes corporate America’s gain because I can help teach other people how to do it this way. And that’s what I mean when I say my purpose of helping people do their best work by being the best version of themselves, because it’s possible. People obviously are craving this. And something that I’ve thought about a lot is, it’s so crazy that with all of the mental health awareness that we have these days, and like all of the focus that we have on trying to create more intention with what we’re doing, how we’re doing it. We still make it so difficult for each other on a consistent basis. Like, how we treat each other in email, how we treat each other in meetings. We make it far more difficult than it should be.   

MOLLY WOOD: Timm Chiusano, you can find him on TikTok right now. Timm, thanks so much for the time. I appreciate it.   

TIMM CHIUSANO: My pleasure. Thank you for having me.  

MOLLY WOOD: Thanks for listening to the latest episode of WorkLab, the podcast from Microsoft. Please subscribe if you haven’t already, and check back for the next episode, where we’ll continue to explore how AI is transforming every aspect of how we work. If you’ve got a question or a comment, please drop us an email at [email protected], and check out Microsoft’s Work Trend Indexes and the WorkLab digital publication, where you’ll find all our episodes along with thoughtful stories that explore how business leaders are thriving in today’s new world of work. You can find all of it at microsoft.com/worklab. As for this podcast, please, if you don’t mind, rate us, review us, and follow us wherever you listen. It helps us out a ton. The WorkLab podcast is a place for experts to share their insights and opinions. As students of the future of work, Microsoft values inputs from a diverse set of voices. That said, the opinions and findings of our guests are their own and they may not necessarily reflect Microsoft’s own research or positions. WorkLab is produced by Microsoft with Godfrey Dadich Partners and Reasonable Volume. I’m your host, Molly Wood. Sharon Kallander and Matthew Duncan produced this podcast. Jessica Voelker is the WorkLab editor.