Work Transformation Expert: We Must Reimagine Work! The Current Model is Broken | Cali Williams Yost

EntrepreneurshipWork TransformationAI
Written By Naomi Haile
 

Listen to the episode on Spotify and Apple Podcasts | Watch on YouTube

Listen to the episode on Spotify and Apple Podcasts | Watch on YouTube

"You have to create the infrastructure, the architecture that's going to work for your business, and that does take deliberate effort. But what happens when that happens? It's magic." — Cali Williams Yost

Cali Williams Yost is the Founder and CEO of Flex+Strategy Group (FSG), a futurist, and was called "one of the most sophisticated thinkers" on the transformation of work by The New York Times. In the 90s, Cali graduated from Columbia Business School and began working in banking, at a think tank, and after seeing a large gap in the market, she launched her own consulting practice in 1998.

For nearly three decades, FSG has helped organizations define the optimal operating architecture that drives high performance across places, technology, and time. Cali and her team engage all levels, from the C-Suite to the frontline, to build on what's working, reimagine what's possible, and then make that vision a reality guided by a proven, evidence-based framework.

She has worked with and is trusted by organizations like BDO USA, The Gates Foundation, Columbia University, Stanford University, ConEdison, Memorial Sloan Kettering, and the Singapore Government.

At a moment when many organizations feel they must make consequential decisions about AI and talent reactively, Cali is truly that leader that is looking at the data and helping leaders transform work deliberately. You can find her commentary regularly in the Wall Street Journal, Harvard Business Review, CNBC, NPR, and NBC Nightly News.

Cali is the author of two books on work transformation, “Work+Life; Finding the Fit That’s Right For You” and “Tweak It; Make What Matters to You Happen Every Day”, and is a sought-after keynote speaker for audiences worldwide.

Connect with Cali Williams Yost

Connect with Naomi Haile

This episode is for you if:

  • You're rolling out AI to your team and can't figure out why adoption feels like a fight

  • You're still relitigating return-to-office policy instead of the actual question underneath it

  • You manage a team that spans generations and aren't sure who to invest in as older workers retire

  • You've been told "work-life balance" your whole career and it's never once felt true

  • You're weighing a reset (in your business or your life) and want it to be deliberate instead of reactive

  • You lead change inside an organization and keep hitting resistance you can't quite name

Looking for a specific gem?

  • 00:00 Welcome and introduce Cali Williams Yost and Flex Strategy Group

  • 04:39 Growing up with a single mom whose work model didn't fit her life

  • 07:31 The bank CEO's "stone cold businessman" line, the moment Cali decided to quit

  • 15:03 Starting with the work, not the tool

  • 18:04 The return-to-office mistake companies are now repeating with AI

  • 21:37 The foundational conditions an organization needs before change will stick

  • 24:02 Nobody trains managers — and why that's become unsustainable

  • 25:22 The labor demographic shortage nobody's talking about

  • 27:37 Reactive layoffs today, a talent cliff in three to four years

  • 27:55 Why letting older workers retire wastes irreplaceable domain expertise

  • 30:59 Why global companies aren't worried about the labor shortage

  • 32:55 The "light bulb" moment that became the concept of work-life fit

  • 32:35 Why "balance" puts unfair pressure on young people

  • 37:22 The Oprah and Emma Grede moment that proves the point

  • 39:13 Resetting the business when her daughter got sick

  • 42:44 Redefining success instead of chasing an all-or-nothing standard

  • 44:59 Her advice to young people: there's no fixed 50-50 split

  • 46:33 Where to start with AI if you don't have a massive budget

  • 49:26 Her book got scraped by AI

  • 51:32 Making space for fun in the middle of all this change

Conversation Transcript

Naomi Haile: Welcome to another episode of the Power of Why podcast. My name is Naomi Haile, and today I am here with the one and only Cali Williams Yost. Cali, how are you doing today?

Cali Yost: I am absolutely thrilled to be here with you, the one and only Naomi.

Naomi Haile: We've been having a lot of fun this last year, and it's been such an honor to learn more about you, get into the nitty-gritty of your work, and how you really support leaders when it comes to the future of work and how they can create more sound, forward-looking organizations. So for everyone listening, Cali is the founder and CEO of Flex Strategy Group, a futurist who has been called one of the most sophisticated thinkers on the transformation of work by the New York Times.

Cali graduated from Columbia Business School in the '90s and began working in workplace flexibility and strategy consulting at a think tank. After seven years in banking, including as a manager, she recognized that the academic, top-down policy approach to work flexibility wouldn't succeed without business execution. Unable to find consulting firms doing that work in a way aligned with her ethos, she started her own practice in 1998, focused on operationalizing flexible work arrangements within businesses. For nearly three decades, Flex Strategy Group has helped organizations define the optimal operating architecture that drives performance across places, technology, and time.

At a moment when organizations are making consequential decisions about AI and talent, Cali is the leader looking at the data and helping people transform work with deliberate action. She's trusted by organizations like BDO USA, the Gates Foundation, Columbia University, Stanford University, ConEd, Memorial Sloan Kettering, and the Singapore government, and her commentary appears regularly in the Wall Street Journal, Harvard Business Review, CNBC, NPR, and NBC Nightly News. Cali is the author of two books on work transformation and a sought-after keynote speaker for audiences worldwide, which you'll get a taste of today.

Cali, thank you for being on the show. I'd love for you to start by sharing a little bit about your origin story, how you grew up.

Cali Yost: Gosh, well, it's funny, when you grow up in the '70s and '80s, the traditional work model was just what you did. What sparked my interest in thinking about work differently was my mom. I had a single mom, and she was brilliant, but she didn't have a lot of options if she wanted to be able to take care of my sister and me. She was a school psychologist, so she had the flexibility to be home by four o'clock and to have summers off. But I knew that wasn't really what she wanted to do, she would have much preferred to be a college professor or have her own psychology practice, and that wasn't going to be possible for her. That was my first thought: the work model doesn't work for people like my mom.

Growing up, watching her chart her path and trying to figure out what that might look like for myself, back in that era, we were starting to think about how more women could integrate into the workplace, and that was probably most of the impetus for what ultimately became my work. But what I realized pretty quickly was that it wasn't just women. In that banking role I mentioned, this was the late '80s, early '90s, I didn't have kids. I just wanted my business to run, and I was losing people to a lack of flexibility, because we worked in New York City, and it wasn't just women saying the commute doesn't work for them. So I began to see this much more broadly, even back then. It started when I was younger, but it evolved as I became a manager myself, working inside organizations.

Naomi Haile: You've told a story about one of your team members, a client came to you and said you were making a mistake by not allowing an incredible employee to work flexibly after having a child. Can you share that story?

Cali Yost: Yeah. It was the CEO of U.S. Trust, one of our team's clients. One of the members of my team quit after years with the bank, she'd had a later-in-life child, and at the time she said, "I just can't do the commute." Leadership told her, "Then you've got to leave." I introduced myself to her clients, including the CEO, and he looked at me and said, "You're making the biggest mistake. My relationship is with her. I'm sure you're great, but what we do is we give our people flexibility." It was funny, he could see my eyes go wide, because at that point I was already starting to think about this. I said, "But you think I'm a great guy?" And he leaned over his big, late-'80s desk and said, "Actually, I'm a stone cold businessman, because you know what? They stay with me forever."

And I thought, okay, I'm out. I'm leaving this job. I'm going to become a flexibility strategist, because this is the future. If this CEO is telling me this, he gets it, and he's right. That's what prompted me to take the leap into this new reality of work that was emerging.

Naomi Haile: That story really stuck with me. After doing this work for three decades, how many of those leaders are you seeing now, even in 2026? Is this common? What's the overall sentiment you're hearing from leaders?

Cali Yost: Before COVID, most of the audiences I stood in front of gave me the polite golf-clap, "that's fantastic, not doing any of that, but okay." Maybe 10 to 15% of leaders would come up afterward and say, "You're 100% right, we've got to do this differently." Those were the ones we worked with, whether it was because they saw talent they were losing, talent they could attract with more flexibility, or because they already knew they weren't using all their workspace. We weren't at 100% capacity utilization before COVID, the average was about 65%. So these leaders were already asking, "Why am I paying for all this space if it's only occupied 65% of the time? We could do this differently."

During COVID, I had a lot of hope that leaders would finally get it, that we weren't going back. There was a meaningful period where we all worked very differently. But it was crisis-driven execution of flexible work, not intentional. I thought, okay, at some point leaders will say, "A lot of this worked, how do we take the lessons from COVID and build a more effective, efficient way of working?" That didn't happen. There was this fantasy that we could go back to what we had, and we got round after round of mandates.

We're now in a situation where more than 25% of workdays are happening outside the office, but only 11% of teams have actually optimized the model they're operating within. That's an enormous amount of lost productivity and efficiency being left on the table. I'm hopeful that more leaders beyond that 11% will engage their teams in an intentional process, asking, based on what we need to get done, how, when, and where does that happen best? And that includes AI. It's all part of the same whole. I think younger leaders especially are going to say, we're not full-time in the office, but we do need to optimize our time together, what does that look like? Even more so with AI, we need the human element to be thoughtful. How do we build a really high-performing, flexible work model?

Naomi Haile: So much of that tone comes from the top, but you also connect with the people actually doing the work every day, and they're such a big part of making any transformation stick. For leaders who want to move from reactive decisions about AI and work transformation into a space of possibility, what can we create, how can we reimagine this, how does a company actually go about that? What are the frameworks you teach?

Cali Yost: That's a big question, but to try to encapsulate it, it all starts with the work. It's stepping back and asking: what is the work that we do? What is our purpose? What are we trying to deliver? What are our services? Then breaking that down and building a consistent process. Everyone gets very concerned about fairness and consistency, which is understandable, but even within the same organization, you have different types of jobs and teams operating in different ways. The consistency is in the process, and that process starts with the work.

You look at the work and ask: based on what we're doing, where does this happen best, so we're as effective and efficient as we can be? When does it happen best, when do we need to be in real time together, and when can we work asynchronously and still be effective? What tools and technology support that? And obviously, AI is an element of that, what part of the work is actually going to be done well with AI? I don't think we're fully there yet with agentic work. Maybe in the future. Right now there still needs to be a human in the loop in many cases, and there are boundaries around when work happens best, you can't have people working 24 hours a day with their agents. A lot of these parameters just need to be defined based on what you're trying to do, and that's the work that has to happen.

It's not about people saying, "We have to get it done, we have to", it's about sequencing. You have to take the time to sequence this and set the parameters, because once you do, you'll be so much more effective and faster. You have to go a little more intentional at the beginning so you can go fast in a way that doesn't burn everybody out and ensures you're producing quality output and achieving the objectives you set. Otherwise it's just whack-a-mole, which feels very overwhelming to a lot of people right now.

Naomi Haile: Putting structure around the uncertainty.

Cali Yost: Exactly, and things are moving quickly.

Naomi Haile: One thing I wanted to bring up, building on what you said about starting with the work, oftentimes what I see is people trying to start with the tool.

Cali Yost: Totally. Oh my gosh, we made the same mistake with RTO, return to office. We started with the where. That's why we're still arguing about the number of days. Let's put that aside and ask again: what about the work? What are we trying to do? Where does that work happen best? You'll start to see, okay, it makes sense for us to be in person this amount of time, on these days, to do this work well, and we don't have to be together in person to do this other work well. How do we make sure we're still communicating and collaborating? It's the exact same thing with AI. You're starting with the tool, not starting with the work and figuring out how the tool can serve that work.

And you end up in the same trap, so focused on the AI that you're measuring how many times people use the tool, which tells you what? That they're using the tool. Okay, but what is being produced by that? Because they didn't start with the work, they don't have anything to engage against. We keep avoiding it, Naomi, we really have to redefine the work model. Everybody wants to skip straight to execution, but you have to create the infrastructure, the architecture that's going to work for your business, and that takes deliberate effort. But, as you know, because we've worked together long enough, what happens when that happens? It's magic. That's why I still love all this so much, because of that spark. If you involve people in figuring out where work happens best, when it happens best, how it happens best, and put those parameters in place with the workforce, they will jump in. They will be creative. They will do it. But you have to create that space and give them the process to walk through together.

Naomi Haile: That's fantastic, and I know you have so many case studies of this going well. Early on, you mentioned the resistance certain leaders have when engaging with your work, "this is going to take so long." And it does take time. What do you say to people who are stuck on "we don't have time to get this right at the outset"?

Cali Yost: Two things. One, how would you like to just stop talking about RTO? Would you like to stop talking about it? Because we've talked about it for years now, and if you'd taken the time up front to sequence through something where the parameters were set with your people, you wouldn't still be talking about this. It would be over. It's taking longer precisely because we didn't do that up front, and it's going to be the same with AI. You can storm in and throw AI at everybody, sure, that'll get people to use the tools, but it'll also cause a lot of resistance, because people won't know what they're doing or why they're doing it. There won't be clear messaging about the purpose of it. Then there's the norming, you have to create space for some of the people who are further along, the ones who've already figured out how to do their job with it. You capture what they've done, and you work with the people who are further behind to help them get on board. You have to take the time to walk through that process, because once you do, people are able to understand how to engage with the technology. Otherwise you're just sitting there, not moving forward. Sometimes you have to take the time to go faster.

That feels contrary to how leaders think, it's like, "just do it." But that's not how human change psychology works. If you involve people, they'll engage, and you'll get more from them. You have to be willing to hold that space for change and give people permission to follow a process. And when the inevitable "I don't get it" comes up, you say, okay, we're going to keep doing this, and then you'll see the magic on the other side.

Naomi Haile: This is change management in its truest form, for organizations of all sizes, and I typically work with small organizations, under 15 people. What would you say are the necessary conditions when you're starting an engagement with a team or multiple departments? Beyond leaders holding that space for change, what needs to be in place for an organization to say, "Okay, we're ready to walk through this process, and we're well positioned to see success on the other end"?

Cali Yost: The foundational pieces: there needs to be a clear understanding of what you're trying to accomplish, and all the leadership needs to be aligned on what the problem is. Often there's a top-down dictate without leadership actually getting on the same page about what we're doing, why we're doing it, and the narrative for why we're going to be in person a certain amount of time. It can't just be "we need to collaborate", it has to be a specific rationale for why you're in person, a rationale for the norms around when you communicate with each other, and the tools you're going to use with AI. Leadership has to be aligned on why this technology matters, what it means for jobs, how people should think about cost-cutting, and what the purpose of the technology actually is, what's the time frame, what outcome is it supposed to achieve.

And then you have to make sure people have the right training to do this correctly. Sometimes we just throw things at people. If you're a manager with people working on-site and remotely who have to collaborate, you have to know how to manage that, we have to train managers, and we have to train people. When you're someone who has to be intentional about your in-person work versus what you're doing when you're not, or when you have to figure out how to apply AI to your job, you need to be trained in that. You can't just be given access to Claude or Copilot and told, "Have at it." That's too much to ask of people. So foundationally: leadership needs to be aligned and able to articulate what you're trying to do, where and when and how work is happening, and the rationale behind it, and then people need the right skills, capabilities, and tools to move into the change. A lot of times that just doesn't happen.

Naomi Haile: I love the emphasis on making sure managers have the training to lead their teams, especially new managers who haven't been taught how to do that. They're exceptional at what they do, and that's earned them the title, but leading people is a skill in and of itself.

Cali Yost: We don't train managers, Naomi. We never have. We've always just thrown them in the deep end, and maybe that worked back in the day, but it's too complicated now, there's too much complexity. And as we move forward, now there are AI agents on the team too, and you're supposed to be managing people and technology. That's a skill, and I'm not sure everybody has it. Honestly, I think the competency required to be a leader and manager today means maybe not everybody gets to be one, and there has to be a career path for people who are smart, contributing subject matter experts who don't have to become managers just to make more money or get development opportunities. Management and leadership today requires a level of competency you can't ignore anymore. It's a must-have.

Naomi Haile: One thing I really wanted to talk about on this episode, something you've been writing a lot about, on Substack and LinkedIn, is the labor demographic shortage. I've been sharing the data points you've shared with peers of mine, and as you've mentioned, almost nobody actually knows this is happening.

Cali Yost: It's crazy, because it's well documented and has been for years, and yet nobody, we're getting ready to hit a labor demographic cliff. We're already hitting it, but it's really starting to show up now, and it's going to be interesting.

Naomi Haile: And that year is approximately 2032, right?

Cali Yost: It's going to start to accelerate. The most recent labor force participation rate is lower than it was, and the largest share of that is aging workers leaving the workforce. Another big share is caregivers who've had to leave because of elder care responsibilities, and that includes men, not just women, and people who can't access childcare. We have older workers leaving and retiring, we have people leaving to care for children and older relatives because they don't have care support, and we don't have as many people coming into the pipeline behind them, they just don't exist. This is going to accelerate over the next five years.

Naomi Haile: So what does that mean for organizations making very short-term, reactive decisions right now, the layoffs, the "we're going to replace X percentage of workers with AI" thinking? What does that short-term thinking actually mean down the line?

Cali Yost: A couple of things. First, you have to hire young people. You can't assume you're not going to need to populate your pipeline with younger workers, even though AI may be taking over some of the historical tasks they used to do, you've got to develop them so that as older workers retire, there's someone coming up behind to take over the work. The danger is that whole industries aren't hiring young people into entry-level roles. What happens in three or four years, when everyone's retired and you're suddenly looking for people? They won't be there.

Naomi Haile: Did any part of your research touch on what's happening with fellowship programs and early-talent career development programs within organizations?

Cali Yost: I've seen talk. I haven't seen a lot of action. There's a lot of talent decisions being made by default right now. I don't think you should be letting all these older workers go and just retire, because they're the ones with the domain expertise you need to train the AI, and ultimately to train younger workers to have the foundational understanding of how the work is actually done, so they understand what's coming out of the AI. There should be real mentorship programs, some of these older workers, who may not want to work full-time in an office every day, could take on the role of mentoring a younger worker: "Here's how you do this job, here's what the AI is producing, let's figure out how you use your judgment to make sure it's correct."

We're not being creative with work models right now, and we're not finding ways to attract and retain the people who'll be in that middle role, the ones with both domain expertise and AI capability. They're going to be extremely valuable, because there will be fewer of them, and you'd better have the flexibility and the employee value proposition that makes you an attractive employer for that group.

Naomi Haile: Was there a third point?

Cali Yost: The first was: you need younger workers and mentoring. The second was: keep the older people in that mentor relationship, bringing domain expertise together with the younger worker. The third is: figure out your employee value proposition so you're attracting and retaining that middle group, which is going to be smaller and more valuable, and includes the people managing kids and elder care. There needs to be flexibility and intentionality built into that middle part if you want to compete for that talent.

It's interesting, I've been doing all these leader interviews, and one thing that's come up is that global companies aren't worried about the labor demographic shortage, because their attitude is, "We're global, we'll just find the talent somewhere else." There's a lot of talent in the world, but they already have the infrastructure in place to integrate someone who isn't physically present in the same office. If you don't have that infrastructure, how do you access that talent virtually, or bring it to you?

Naomi Haile: That's a conversation I've been bringing up in different spaces, off the back of your research and the data points you've pulled from multiple sources. The other part of the equation, and a huge topic in your books, is the individual, and this idea of work-life fit. Beyond organizational responsibility, where does our own individual responsibility come in, when it comes to our development and upward mobility? Can you talk about work-life fit as an alternative to balance, especially in this moment of increasing caregiving responsibility and labor shortage?

Cali Yost: Work-life fit came out of my work thirty years ago. I'd go into an organization and say flexibility would help people balance work and life, and every leader I talked to would just zone out, because to their mind, I was talking about working less. One day, out of nowhere, I said, "No, it's about people fitting their work and life together." And I'm telling you, a light bulb went off for this guy. He said, "Oh, I get it, my work-life fit," and he went on and on about the different ways people have work-life fit. That completely changed a conversation that usually goes nowhere.

I realized this concept just made sense to people, because we all have a different way our work and life fit together. There's no one right way to do it, and the way it fits together at any given time is going to change, it's not going to stay the same. The problem I found is that we'd go in, build flexible work models, and then individuals wouldn't know what to do with them. You have to grab it, the company can't hand it to you. You have to say, based on the flexibility I have in my job, how am I going to prioritize and plan what I do at work and in my life, and how does that fit into the model I work within? People had no idea how to do that. I figured somebody must have already built the toolkit for this. They hadn't. So I researched people I call the "work-life fit naturals", people who just seemed to do it and didn't understand why it was so hard for everyone else.

My first book was about the people who reset their work-life fit, when you have to really work differently, it's work plus life, finding the fit that's right for you, with a step-by-step process for creating a plan, presenting it to your employer, and making it work. My second book, Tweak It, is about the day-to-day, the small shifts in how and where you're working so you can fit your work and life together. Work-life fit is a skill everybody needs, and almost nobody's given it, so we struggle. And "balance" as a word makes it worse, it's a deficit model, it makes you feel like you're always missing something. I've never met a person who has balance. We all sit around talking about not having it, and that doesn't get you anywhere. But if you ask how your work and life can fit together, that's when you move into a place of possibility.

The goal of my books was to give people the structure to think that through for themselves. It goes back to the whole idea of magic, once people can think through how their work and life fit together, they start to see the possibilities and figure out what works for them, and you remove the judgment. That's the part I think young people particularly struggle with, this idea that "I need balance, I need balance." But you're starting a new job, and you want to get in there and make your mark and learn everything you can, so you might be working more than a "balanced" schedule would suggest. That's okay right now, as long as you're intentional about what else in your life is meaningful to you and still doing what you can there.

Balance puts a lot of pressure on young people who genuinely want to work a lot in a particular season, it makes them feel like they're failing, when really, as long as it's intentional, it's working for you, and you're healthy, that's fine. There'll be another time when it looks different, and that's okay too.

Naomi Haile: That was a piece I really loved, I think it might have come from one of your LinkedIn posts, or a conversation we had, about how your work-life dynamic has looked different throughout your career. It's not a fixed thing.

Cali Yost: No, and it actually came up in the conversation around Emma Grede's podcast tour, and Oprah went on and had the exact same problem. I was like, oh no, we all have to stop talking about balance, because it's making this conversation so difficult. Poor Oprah is saying no young person should think they're having balance, and everyone freaks out on her. What Oprah was trying to say is: as a young person, your work and life are going to fit together in a way that might mean you're working a lot, but that's because you want to. Then, as your life goes on, it may change, and that's all she was trying to say. But the word "balance" got everybody twisted up.

I think Emma Grede is trying to say the same thing, if we could all just talk about work-life fit instead. If somebody looked at Emma and said, "How do you fit your work and life together?" she could tell them, and then someone else could say, "This is how I fit mine together," and both could be true. But we don't, we keep talking about balance. And I have to put my plug in for why integration isn't the answer either, because research shows half of people don't want their work and life integrated, they want it separate. If we say the goal is integration, we lose that half of people entirely. If your fit is "I want it all together," that's fine. If your fit is "I want it separate," that's fine too. That's what my books lay out, how to figure out your fit within the context of the flexibility you have in your job.

Naomi Haile: It's so personal, even when you've shared about your own work-life fit around starting a family, you also shared that your daughter was ill at one of the peak points of your career. Do you want to share how you navigated that?

Cali Yost: Yeah. One of the key messages of the work-life fit journey is that you need to be able to reset when things stop working, you have the power to make small changes and get to a better reality than the one you're in. It's not all or nothing; we tend to get very extreme, thinking we're either all in or all out. That's not true.

This was a few years ago, before COVID. We were really busy, lots going on, and my daughter got really sick. We didn't know what it was at the time; it turned out to be POTS. There was probably a period of six months to a year where she needed a lot of support. We had a couple of projects wrapping up, and I said, we can't backfill in two more, we need to stick with what we have and reduce the pipeline for a period of time. We got to the other side. We didn't shut down, but we thoughtfully assessed the capacity we actually had, given what I needed to do, and adjusted. Once we were on the other side and she was better, I was able to reengage the way I had before. But it was a very deliberate, intentional reset that we made as a team, I've done the same thing with other people I've worked with. There's a lot of room to be thoughtful and intentional as realities change, and that's what I hope we do more of, instead of thinking it's either "you're in" or "you're out." It's about figuring out how to make it work as things change.

Naomi Haile: And that judgment piece you mentioned earlier, the pressure the word "balance" puts on people. I'm sure just being able to articulate how you saw that winding down and back up, and being more present where your priorities were, must have alleviated some of that pressure to feel like you needed to be doing something else.

Cali Yost: Yes, but my mind sees that as natural now. I wasn't, though. That's why I wrote those books, I really wasn't a natural at this. I was an all-or-nothing person. If I wasn't making it work perfectly, I felt like I wasn't making it work at all. What I learned is there's a lot of power in making deliberate decisions a little differently, you're not doing as much work, you're not making as much money, and there were clients I really wanted to work with that we had to turn down. That was a bummer. You have to redefine success for yourself, too. Part of that process is being as intentional and flexible with your definition of success as you are with how your work and life fit together, and we don't talk about that either. You're perfectly capable of saying, "For this period of time, I'm not going to worry about being promoted, I'm not going to take the coolest projects, I might not make as much money", or there might be periods where you're all in on work, like during COVID. I worked a lot during that time because there was just a lot going on, and luckily my kids were healthy, so I could focus more on those other aspects of success rather than caregiving. But then my dad got sick, and we reset again. It's about making sure you can see the possibilities and keep adjusting the dials.

Naomi Haile: I have a tattoo that says "You are on your own path" on my arm, that idea of focusing on your own personhood and your own path is exactly what those two books are about, for that same reason. Right now it's so easy to compare yourself to others and feel like you need to define your version of life quality on terms that aren't even true to you.

Cali Yost: That's a fantastic mental model, Naomi. I love that for young people especially, because when you ask what people prioritize at work, a lot of research shows work-life balance ranks number one, and that's great, but you have to get out of that construct, because it's limiting. It makes you think there's just one way to do this, and there isn't. There will be many different seasons in your life and your work-life fit. What young people are really trying to say is they want to fit their work and life together in a way that's whole and healthy, and that doesn't necessarily mean a 50-50 split between work and life. My goal now is to say, "Yes, you're right", we need to be thoughtful, but within a construct that allows for flexibility and room for what that looks like for you.

Naomi Haile: As we start to wrap up, you mentioned AI is part of the framework you use within your high-performance flexibility model. I'm sure now every leader, every company, has AI at the top of the agenda. For organizations that want to take a deliberate step toward integrating AI, especially ones without huge budgets to invest, where's a good place to start, while staying mindful of your workplace flexibility model?

Cali Yost: I think that's a good way to frame it. Organizations with a lot of resources are just hitting it hard. Here's what I think: if you introduce a set of tools you're comfortable with from a risk standpoint, and I cannot say this enough, the governance around AI and the cybersecurity piece of this is very, very, very important, make sure whatever structure you land on is one you're comfortable with in terms of how your data is being organized. You and I have talked about this from a security standpoint; it's very important.

Once you're comfortable with the tools and how people will use them from a security standpoint, it makes sense to give people some training, the basics of AI fluency, how to think about using it, and give them permission to experiment. What I think is emerging is that you'll have people who just dive in and figure it out, not the IT people, just people in their jobs, and they'll go figure it out on their own. Then you want to find out what they're doing, capture that, and let them share it with everyone else, so it feeds up to an innovation team that decides what gets scaled. That's great if you want to formalize it, but I do think we're at a point with AI where once the tools are introduced, and you have these people who just do it, you begin to capture what they're learning, continue to train, and continue to give people space to experiment. But again, be clear on how people are using the tools in your organization, give them initial training, let them go, capture the lead users, not the IT people, the people in the business who've figured it out, share that, and keep iterating on the process.

Naomi Haile: There are definitely super-users everywhere, it's such a spectrum.

Cali Yost: It is. Super-users, and then the people who have no interest, or are vehemently against AI, period.

Naomi Haile: And everything in between.

Cali Yost: It's so interesting, the people who are vehement... I was, honestly, about a year and a half ago, because my book got scraped and used without my permission. That sent me into orbit, I was furious. But then I decided: if somebody else is going to use my stuff, we're going to use our stuff too. How do we do that? That's what started us on the journey of figuring out how to capture all of our data and use everything we'd created over the years, thoughtfully, with AI. You kind of have to get over it. We had someone shepherd us through the process and show us how to use the tools, and that's what every organization has to go through. Now we're like, yay.

Naomi Haile: And you've got the tools, but there's still so much learning on the back end.

Cali Yost: So much learning, right? I mean, I'm learning from you. But once you have that framework, that foundational framework, you can keep going.

Naomi Haile: Right. This is fantastic, Cali. Thank you. You're the one person in this space who not only brings forward all the data points from research reports and government data, but also shares your point of view on what this means today and in the future, how organizations can set themselves up and really support their people. And the way you articulate it is so thoughtful, funny, and easy to understand, which is what I think a lot of people need right now, when they don't know what information to trust, who to trust, or where to go for reliable insight. Thank you for continuing to do this work, and for helping us do this work too, we really appreciate it.

Cali Yost: I wanted to take two seconds on the concept of fun. We have to make this fun, because it is fun. This is all very overwhelming to people, and I think we have to find the good news in a lot of this. I've seen it, if you create the space and give people permission, the heaviness lifts. That's part of what I want to do: help people start to see the good news, because there is good news.

Naomi Haile: Yeah, that's a great perspective. Even from our own conversations, and the conversations you've been having with people in your ecosystem, people are looking for that, they're looking for the good.

Cali Yost: They are. They want the hope, and they want the fun, and it can happen. It really can.

Naomi Haile: Not to be cheesy, but as you were saying that, the sun literally came out.

Cali Yost: Here we go. That's a sign.

Naomi Haile: I love it. Thank you, Cali. What's the best place for people to connect with you, I know we talked about LinkedIn and Substack.

Cali Yost: LinkedIn, Substack, we're there. Taking a little break this summer for a couple of weeks, but we're there.

Naomi Haile: You'll be back in the fall.

Cali Yost: We'll be back.

Naomi Haile: I'll share all the links for where people can read more about Cali's work, watch her interviews, and connect with her online. Thank you, Cali, for being on this episode of the Power of Why podcast. And thank you to everyone taking the time to listen, we look forward to the next episode.

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Naomi Haile
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