Will AI Make Work More Human?

MOLLY WOOD: Erica Keswin is a business strategist who has worked with the world’s most iconic brands over the last 25 years. She’s an outspoken advocate for a human-first workplace, especially as AI dominates the conversation. In fact, she’s published three bestselling books on the topic. Her latest book, The Retention Revolution, just came out in October. Retention as we know it is a bit outdated, according to Erica. The reasons people stay at a company have really changed. Connection to our work and each other is paramount. So is flexibility, personal development, and even an open door to exit through when the time comes. In today’s episode, I chat with Erica about the human workplace, what that is, how to cultivate one, and why it’s more important now than ever. Here’s my conversation with Erica.

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MOLLY WOOD: Erica, thanks so much for joining me. 

ERICA KESWIN: It’s great to be here. 

MOLLY WOOD: So Erica, you have been so prescient on this topic of a human workplace. Your first book, Bring Your Human to Work, was published in 2018, which was of course well before the pandemic, the generative AI boom, quiet quitting—all of these workplace trends we’ve seen over the past few years. Today, in 2023—almost 2024—these books are more relevant now than ever. So let’s start with a definition. What is a human workplace? 

ERICA KESWIN: So it’s funny that you go all the way back to 2018, which I love. When I wrote Bring Your Human to Work, people at the time thought I was talking about my dog, Cruiser. And while I would say my dog Cruiser’s a very human dog, I was actually talking about something different, which is about creating a workplace that’s not only good for people but good for business, and how those two things are not mutually exclusive. And if I were to boil it down to one phrase of what it means to create a human workplace, it’s a workplace that honors relationships. 

MOLLY WOOD: How does that resonate even more now, would you say, in this era of structured flexible work, Gen Z, and generative AI?

ERICA KESWIN: During the pandemic, many leaders were more human. Some of them it was in their nature, and some of them it was sort of by default. And when we looked at their survey data around employee engagement and job satisfaction, it actually went up during a very stressful time. And so when I think about what those leaders did then and what they need to continue doing, none of it is rocket science. You know, they check in with people, they ask them, how are you really, really doing, and they make sure that people know—especially, this is what Gen Z wants. They want to feel like their leader actually cares about them as a human. And so when I think about the world of generative AI, one of the things that I’m seeing is that generative AI, in addition to being great technology, actually is making, from where I sit, the human skills that much more important. 

MOLLY WOOD: You’ve given the example of making that personal connection at work. But how do you think those leaders can start to put this into practice in a really structured way? 

ERICA KESWIN: If I were thinking, what would be on my to-do list for 2024 as I think about retention, you know, what employees want, one of the biggest things they want is to develop and grow on the job—up, down, and sideways. And the chapter in my book where I talk about this, it’s called From Ladders to Lily Pads, because long gone are the days where there’s a hundred rungs in the ladder and people stay for 50 years and get a plaque and a pension. And so as leaders, one of the things that we need to think about doing is to be creative about how to help people develop when there aren’t as many rungs going up. We need to think about internal mobility. How do we move them across? How do we possibly even move them down? Sometimes the best new role for somebody might even be outside of your team or outside of your organization. Actually have conversations with employees and ask them, how do you want to grow on the job? And the reason why it’s so important is that if a culture doesn’t have that sense of psychological safety, where people can bring their human to work, they are not going to be open to answering that question. 

MOLLY WOOD: I’m curious about this idea of growing down. That’s not something we hear about that often. Can you tell us a little bit more about that and how leaders can shepherd that kind of growth? 

ERICA KESWIN: Not everyone, given a certain moment in time in their life, necessarily needs to feel like they’re going up the ladder. You know, there might be a time where someone’s taking care of elderly parents, taking care of kids, wanting to just do something a little bit different. So I profile people in the book that are over-the-moon excited to take a lateral job, even a step back. Or maybe they had an outward-facing role and have decided that they’d rather have an internal-facing role. What I would say in terms of leaders and empathy, whether it’s talking about a job change due to generative AI, or any change—we’re going from two days back in the office to four days. Given the last couple of years, people are on edge. There’s been so much change. So I have a recipe, what I call a recipe for a human leader in this moment, and it cuts across anything that we need to start to communicate. And my recipe—and it’s funny that I even have a recipe because I don’t cook—but my recipe is one part vulnerability for you to say, I also haven’t been down this road before. Even as a leader, generative AI could impact my role. Even I as the boss don’t have this all figured out. So a little bit of vulnerability. The second part of the recipe is empathy to say to people, look, I know this has been challenging for everybody. I know this is not easy. A little bit of empathy. And the third part of the recipe is really important—I mean, they’re all important, but it’s experimentation. That is, hey everybody, we’re making this change and all I can say is that this too may change. This change may change, that we are experimenting and this may not be forever. Because I do feel like regardless of the topic, people are walking around with their shoulders in their ears because they’re so stressed. And so if you approach it with these three pieces, especially the last one, experimentation, I do find that it takes the temperature down. 

MOLLY WOOD: One of the things you also talk about in The Retention Revolution is that developing tech intelligence is paramount, but that you can overdo it. And so as organizations and leaders are thinking about how to integrate and train their employees around generative AI, how do they find that balance?

ERICA KESWIN: Yeah, so I talk a lot about finding the sweet spot between tech and connect. That sweet spot is about leveraging it for all of its greatness and then putting that technology in its place. One thing that I did recently, as when my book came out, was to go out to Seattle and participate in an event with Jared Spataro’s organization, who does a lot of the work around the generative AI and Copilot.

MOLLY WOOD: Just to clarify, Jared Spataro’s organization is Microsoft. 

ERICA KESWIN: Yeah, and twice a year they have team week, where all 250 people from all over the world, wherever you live, come to Seattle to spend a week together. And it’s not anti-technology, anti-generative AI in any way, shape, or form, but it is taking time to build relationships and to really connect on a human level. Because what we see is that once you leave that week and you go back and you’re using all of your technologies to continue to connect with each other and to move your work and projects forward, your ability to do that is that much stronger, having built the relationships in person. 

MOLLY WOOD: The entire thread of your three books, up until The Retention Revolution, really is this idea of humanity, and it is a challenge to leaders. And I wonder how you see generative AI specifically contributing to helping these leaders become better, helping workplaces become more human. I know that feels counterintuitive, but it’s just the theme that keeps coming up over and over, that the humanity cannot be separated from generative AI. 

ERICA KESWIN: Again, it’s all new and moving at such a fast pace, but a few quick things that come to mind. One is that, as technology changes or even takes over pieces of a particular job, oftentimes it’s the human pieces that are still there that are taking on an increased importance. So these are the so-called softer skills, or as I like to say, power skills. I like to also say that the soft stuff’s the hard stuff, and sometimes the really important stuff. So I think it’s going to become increasingly important that we invest in helping people develop those human skills. The second thing I would say is that, I was at a conference recently and someone gave the example of, a radiologist is not going to lose her job because of generative AI. A radiologist who doesn’t know how to interact with generative AI will probably lose her job. And so again, if you are thinking about how you as a human interact with any technology, and in particular generative AI, you need more advanced human capabilities to do that well. And that will ultimately be the difference in terms of leadership, and then training the next generation to do the same thing. Fifty percent of managers say they get no training. They get promoted into these manager jobs because they were good at their individual contributor day job. And I think in 2024, we really need to lean into supporting and celebrating these middle managers. 

MOLLY WOOD: One of the threads that connects all your work is this importance of feeling a sense of purpose and feeling connected to a greater mission. And if you are offloading to computers the things that computers are good at, and you are exercising your analytical and critical thinking skills and developing within your workplace, it feels like that ought to be positive. 

ERICA KESWIN: So I was on an AI panel recently, and I told the story about how in my book I interviewed the CEO of Meetup. And he talks about how when a new person starts, he sends a personal letter or email, that it doesn’t matter what role you’re in, you know, welcome Molly to the firm, we’re so excited to have you. And then he’ll say, your job in fill in the blank X, Y, or Z is so connected to the purpose and mission of Meetup and here’s how. So he is literally connecting the dots between what you are going to do in your job and the purpose and the mission of the organization. When John F. Kennedy went to NASA for the first time and walked into the Houston Space Center and said to the janitor, what do you do? And the janitor said, I’m putting a man on the moon. And so people of all levels and all roles want to feel connected to the purpose and mission of what you do. So my hope is that as generative AI takes over, and all tech takes over certain aspects of a leader’s job, that leader can have more time to connect with his or her employees as humans. 

MOLLY WOOD: Let’s talk about retention more broadly. One of the things that you say in the book that I just think is particularly interesting is that leaders should maintain an open door for employees who choose to move on. Can you tell us more about that? 

ERICA KESWIN: The whole idea of The Retention Revolution is that the world has changed, and with the new generations, they’re not going to stay in one company for a long time. Going forward, the new generation, they look at their career more as a portfolio. I spent many years as an executive recruiter. And back in the day, if I saw a resume with somebody moving all over the place, it was a big old red flag. These days, not as much. People leave if they don’t feel like they’re growing. People leave if they just want to try something else. There’s not as much of a stigma. So if we know that people are likely going to come and be with us for, as Reid Hoffman calls, you know, the founder of LinkedIn, a tour of duty, then we don’t have to make it when they leave to have this feeling of, okay, Molly, you told me you were leaving, you’re dead to me. Don’t let the door hit you in the behind. Instead, let’s be strategic about how we say goodbye and let’s say goodbye gracefully, and let’s give people opportunities to connect, whether it’s through a podcast, whether it’s through learning and development opportunities, whether it’s through a newsletter, whether it’s letting all of our alumni know that there might be new jobs and maybe they want to come back. There have been a lot of boomerangs at many companies, and as we all know, when people leave they’re also a brand ambassador and they may still buy your products. So The Retention Revolution, if you’re intentional about how you onboard and intentional about how you offboard, the workplace just becomes much more of this virtuous cycle, and the world is heading that way whether we like it or not. And one quick example that I’ll give: there was a study done out of one of the broad legal associations, and they found that the brand-new, bright-eyed and bushy tailed lawyers coming into the firms, only 30 percent of them even have a desire to become a partner. 

MOLLY WOOD: One of the things that everyone is grappling with post-pandemic is remoteness, and not every company has the resources to fly people in for in-person gatherings as much as they would want to. Do you have tips for engaging people remotely, and maybe using technology to create that human engagement? 

ERICA KESWIN: First of all, I would say yes, not everybody can afford to bring people back as often as others. That being said, I would urge you to try to put some resources toward bringing people together. And it doesn’t have to be everybody, one location. It could be in a certain city, it could be regional, and where there’s a will, there’s a way. This next comment will highlight my, um, advanced Gen X age, but when I was younger, I watched The Love Boat. And on the show, The Love Boat, if listeners don’t know what that is, you could look it up, there was a woman named Julie McCoy and Julie McCoy was a cruise director. And I’m not telling you all to go hire cruise directors, but we cannot leave connection to chance. And I have a podcast that’s called Left to Our Own Devices because, left to our own devices—excusing the cheesy pun—we are not connecting. And so somebody needs to own connection. What I recommend doing is, create a roadmap—map out your organization, figure out where people are, figure out how, when, and where you might bring them together in person. And then when they’re not, think about how, when, and where to bring them together virtually, but in ways that are strategic. So for example, managers are on the front lines of this retention revolution. As a group, they are overworked, they’re having mental health issues, they’re sort of sitting there in the middle, which I believe they’re really in the center and we need to support them.There are organizations where there are communities of managers that come together virtually to support each other. And it costs nothing other than maybe an hour of your time. But unless somebody organizes it, it won’t happen. It’s not leaving that stuff to chance. And making sure that people own it. But it can’t just be sort of in addition to someone’s day job. It has to be valued. And it has to be celebrated and recognized. 

MOLLY WOOD: Every org needs a community manager. I love that. 

ERICA KESWIN: Yes. A hundred percent. Maybe that’s better than a cruise director, but yes, a hundred percent. 

MOLLY WOOD: Alright, one last question for you. What is the single most important way for business leaders to retain great talent?

ERICA KESWIN: Care about them. 

MOLLY WOOD: It’s so simple and yet so powerful. Erica Keswin, thank you so much. I encourage every leader everywhere to pick up The Retention Revolution and go all the way back to 2018 for Bring Your Human to Work. Thanks so much for the time. I appreciate it. 

ERICA KESWIN: Thank you so much.

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MOLLY WOOD: Thank you again to Erica Keswin, a workplace strategist and bestselling author who has worked with some of the world’s most iconic brands. That’s it for this episode of WorkLab, the podcast from Microsoft. Please subscribe and check back for the final episode of this season, where I’ll be speaking to Nir Eyal, a bestselling author, entrepreneur, and self-described behavioral designer, about how to build healthy habits and improve productivity with the help of generative AI. That episode comes out right in time for the new year. If you’ve got a question or a comment, drop us an email at worklab@microsoft. com. And check out Microsoft’s Work Trend Indexes and the WorkLab digital publication. There you’ll find all of 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 that at microsoft.com/worklab. As for this podcast, please rate us, review, 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.