The way we work is seemingly broken and does not serve us at all. To ensure that the future of work is way better than today, a couple of things we are so used to right now must be vastly transformed. Kate Byrne chats with Jena McGregor, Managing Editor of Charter, who sheds light on how most businesses are trying to fix the workplace using the wrong tools. She explains what it takes for workplaces to improve people retention, how leaders can lead with authenticity and adaptability, and how to prioritize human sustainability when it comes to work. Find out the roadmap to creating truly dynamic workplaces and help change the future of work for good.
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Defining And Redefining The Future Of Work With Jena McGregor
I love our topic, the future of work because let’s face it. We all know the existing system is broken. Guess what? The future one is going to be broken too if we keep trying to fix it with the wrong tools. The words of Einstein, “That would be insane.” That’s why we’re so fortunate to be joined by one of the leading voices in the space, Jena McGregor, who’s the Managing Editor of Charter. It’s one of the up-and-coming leading preeminent platforms and voices for the conversation in the future work, what it’s asking of us and what we’re still refusing to name.
Jena said it’s such a spot this intersection of journalism, leadership and systems thinking. She holds such a clear-eyed view into how work is being redesigned and where it’s quietly collapsing. That’s a good thing because that’s called Evolution. We’re going to take a look at child care, less of a perk and more of a keystone to the infrastructure of the economy overall, why flexibility without care is such a hollow promise, and why, frankly, the metrics we cling to tell us so very little about whether work is working.
If you like what you read, I know that Charter is having some upcoming online events on February 10th and February 24th(https://www.charterworks.com/events/ai-summit/2026/).Stay to the end until the KB takeaways. I thank you as always for continuing to read and support. Let me know what you think. Let’s see what you learned about the future of work and what you can both do about it and where you can find your voice and help change it.
Please join me in welcoming one of the voices in journalism that I have respected for a long time. She’s building out to become one of a thoughtful provocative voice in the future of work, and that would be Jena McGregor, Managing Editor of Charter. Welcome, Jena.
Thank you so much for having me, Kate. It’s great to see you and to be with everyone here.
How Jena Started Studying The Future Of Work
You, too. Jena has been covering this for quite a while, this subject of the future of work, how we redefine power, what advancement even looks like, all of these things. I feel fortunate to be able to have this conversation with Jena at such a critical time with sand shifting everywhere around the world, around the globe, nationally. Especially in this place that we call work. I want to ask first before we go into what you’re seeing in all of that and the trend spotting because they often say history repeats itself. How did you first even get into this whole realm like this beat?
It’s a great question. I sometimes ask myself the same thing.
It seemed like a good idea.
I would say both happenstance, luck and over time a real genuine interest in trying to write about and improve the way that we all spend so much of our days, so much of our time. I was fortunate to look into an internship early in my career that dropped me into business journalism. I knew I wanted to write, edit, and work in New York magazines when that was still a thing and dropped me into business journalism. I got my feet wet and learned a lot about all the basics that were great. I had a couple of career moves that got me writing about the workplace, leadership, corporate governance, and how companies are managed. One of those being with someone that quite well, John Byrne.
I worked at Fast Company where I wrote a lot about these issues. I worked at Businessweek and that’s where you and I first met, at Fast Company before I jumped past that. You and I worked together there. I went to Businessweek where I was the management editor and wrote about many of these issues there. I had a baby, took a little bit of time off, and then landed in what I thought would be a short-term gig and ended up staying many years with the Washington Post. Where I started as a blogger writing about leadership in the headlines and riffing on whatever was the topic of the day. It transformed into a beat where I got to focus on how business leaders in Washington were intersecting.
While I was there later in the period was the first Trump administration when there was so much reaction and response from Corporate America. Time has changed. That was also when the pandemic began and I spent a good bit of time writing about the early days of how companies were responding to the pandemic. I’m telling you my whole story here, Kate. From there, I went to Forbes. Where I lucked into the opportunity.
Journalism's challenge is to figure out how to dig deep and cover a story from every angle without neglecting other issues that matter. Share on XI worked with a former colleague, Diane Brady, who’s now at Fortune. She’s amazing. I had the opportunity there to focus on entrepreneurs and companies that are focused on the future of work to continue writing about all these issues about how we’re dealing with hybrid work and return to offices. That was almost synonymous with the future of work there for a while, the early days of generative AIs launched and stayed there for a few years.
While I was there, I had the opportunity to launch a summit like a live journalism summit focused on the future of work. Which got me interested in the opportunities for event-based journalism, the conversations and topics that we can discuss on stage. I had a short little pivot into a different role and then now a Charter getting to combine all of these things that I have loved and enjoyed writing about, as well as do live events too, which is a perfect fit for me in so many ways.
I love that phrase in event-based journalism. because often, people don’t understand that in fact it is a form of journalism.
I will credit Diane for this. She refers to them as live journalism events and I completely agree. It is an opportunity to have important, powerful and sometimes difficult conversations on stage. They are journalism. It’s just handled in a live event.
Exactly. One of the other things I hope everyone gathered from that and recognized is, you are the penultimate, you’re a wave surfer. You’re on the crest just as something’s and before it crashes down, and becomes a big thing. How exciting to be able to chronicle. The key wave moments of the past series. I won’t assign a timeframe but since you started.
Thank you for not reminding me how long I’ve been at it. Business works that way. There’s that thing that we’re all going to focus on for a while. That’s always the challenge. It’s to figure out how to dig deep and cover a story from every angle and make sure you are addressing it in all the ways it needs to be covered without the risk of neglecting or not covering other issues that matter and should get more attention.
Issues Not Getting Enough Mainstream Media Attention
Now, we’re going to dig into it. Let’s roll our sleeves up. You have an interesting vantage point because you get your marriage where theory meets like real life, lived and workplace reality. What patterns are you seeing now that aren’t getting enough attention in mainstream business media?
Two things come to mind. One of them is getting enough, but it’s starting to get enough but it needs more. Charter’s focus is to bridge research to practice. It is a future of work for a median events company. We have a newsletter with a subscriber base of 100,000. Our focus is on owners of the talent agenda. That’s how we describe our readership. It’s a lot of folks in HR, workplace roles, and C-suite leaders. There is a takeaway for anyone who’s managing people and who’s leading teams.
I don’t think there’s nearly enough focus being paid on the child care crisis. We saw both New York City and San Francisco come out with initiatives for free childcare. This is huge. This is so needed. There was a Brookings report that found we had negative net migration in 2025, which is going to severely impact lots of forms of labor, but child care labor in particular. More than 400,000 women left the work force in the first half of 2025.
Those numbers are stunning and not in a good way.
They’re very concerning. Combined with the extent to which there was a lean in report or a big study that they put out every year about the women in the workplace. Skipping ahead to something else you want to address, but we’re seeing the way DEI programs have been pulled back on or at least renamed in many organizations because of the pressure to do so in the broader landscape. Those numbers are startling. Sum of the numbers I was shocked by.
Only half of companies are prioritizing women’s career advancement. One in four companies now offer fewer remote and hybrid work options. One in six cut back on formal sponsorship and discontinued or scaled back career development programs with content tailored for women. You combine that child care crisis issue with the way in which companies are pulling back on some of these programs that they’ve been doing for years to help women get ahead to broader diversity issues. That is going to have a real impact.
The other thing that is getting some coverage but I think I have a personal interest in it. Maybe because I have teens at home. The impact that AI is going to have on entry level workers and the kinds of job opportunities that the entry level workforce has and how much these are being impacted by AI. For women, you’ve got mothers of young children. You have the child care crisis. We still are dealing with the aging parent issue for anyone in a sandwich generation.
Now, a lot of people at the peak of their careers are also going, “I’m the parent of a teen or a college student or a young adult who can’t get a job. The path to success that I always imagined that they’d be able to take and have invested in so many ways is not working anymore.” That little relief period that a lot of women feel in their careers is going away too. This is not just a women’s issue. This is an issue for everybody.
It’s an issue for pipelines and companies. It’s an issue for how much people are able to get the early career experience that they need. It’s an issue for how well companies will be able to build the pipeline of leadership talent that they need. That should continue to get more coverage and we should continue to look for smart and innovative solutions on that.
Metrics To Measure On Human Sustainability And The Future Of Work
That leads me to another question I’ve got for you. It has to do with measurement and measuring what we have been like output hours, optics from days gone by, versus what matters. What do you think we should be measuring instead of? What should we be looking for if we cared about human sustainability and the future of work?
I’ll tell you what I’m interested in. I feel like the answer you often hear to that is detention. As a company, are you retaining your people and holding on to them? That’s a sign and instead of like, how much work they’re doing or how many hours they’re putting in. If you’re retaining your people, you’re doing something. You’ve created a career path for them and they’re happy but how do we measure retention at a time like now when there’s no job or far fewer jobs for people to go to? Is it as effective as a yardstick?
There was a great story in the Washington Post by a former colleague of mine, Taylor Telford. It was about how much longer older workers are staying in the work force and the impact that’s having on the younger generation. I’m very curious how the issue of retention is going to be looked at now in the years to come as people just job hug, as the buzzword is. You just hang on to your job with clenched fists to make it to the current environment.
I’m very curious how that obvious statistic and measurement will be considered going forward. This is less something very easy to measure but I love this phrase that I heard. I’m probably going to butcher it, but over the years, I’ve had a number of interviews and conversations with Dean Carter, who used to be the CHRO of Patagonia. I worked with him when I took a little pivot out of journalism for a short period. He’s now the CEO of a small AI company, but he had this great phrase. He talked a lot about regenerative agriculture and what you put into the soil creates better plants. This is a big idea of Patagonia.
He talked about this phrase of, “I want to think of the workplace as, are you as the employee getting more out of it than we’re taking from you? Are you getting more out than we are extracting from you? If you feel like you’re learning more, succeeding more and advancing more than we’re pulling from you, then I’m doing a good job.” I loved that concept.
I love that concept too. I’m about to release a quick little TikTok about this notion. It’s based on something slightly different, but it’s being called a Reputational Predator. That’s another thing, so watch it. For this, what that is, the workplace becomes almost predatory. They suck you dry. It’s not reciprocal at all. It becomes a place of pure obligation and drain. What that leads to is certainly not innovation.
Creativity or growth or learning.
Characteristics Of Genuinely Adaptive Leaders
That leads me to ask something a little bit about leadership in this crazy time of flux. Although, I got to say I feel like for the rest of our lives, everything will be in flux. We have a timeless conversation. Everyone talks about leading through uncertainty. From what you’ve seen and what Charter is chronicled and all your past coverage. What seems to distinguish leaders who are genuinely adaptive from those who are just performing confidence?
This is like the question for leaders. You hit the nail on the head. This is exactly what people are grappling with, and it’s a tough one. I’m not going to pretend to have an easy answer. It’s funny because we wrote about this. I can pull a little bit from that, but I think people are looking around. There’s this sense of paralysis of, do I hire or do I not in the current environment? Many people are feeling fear, distraction, and uncertainty. There’s a word that somebody used at one of our events. “I’m tired of saying we live in unprecedented times or I’m tired of living in unprecedented times,” and so is your workforce. Everybody who works for you is feeling the same way.
It was interesting. One of my colleagues wrote a great piece, Brian Elliott. He is one of our executives in residence, who used to work at Slack and is one of the foremost experts on remote work and hybrid work, how to make it work and also the change management that goes into managing that. He’s made some great parallels about how change management for remote organizations that were good at change management when it came to remote work and hybrid work are going to be better at it when it comes to AI transformation too. You’ve already developed the muscles and the skills to try to transform your organization for something else and so leg up to those organizations.
He’s writing about how much more quiet executives are than they were. I mentioned this earlier in our conversation. You saw all these executives come out and speak much more prominently about the issues of the day during the first Trump administration and now amid all the pressures, the attacks and the ways that businesses interact with Washington. You’re seeing so much more quiet and reservation about speaking out on these issues.
What he focused on is that a lot of executives learn their lesson from those times and maybe don’t want to engage in every single issue that comes out. That’s understandable because you might have gotten a little burned. People still need to hear from you somehow. If you’re not talking to them or offering support, then you’re going to have a distracted workforce. You’re going to have people who do not feel safe.
A lot of his focus was not on, let’s jump in and talk about the latest issue of the day and get political in any way. Focus on what you know, connection, finding ways to ask people how they are or how they’re doing, doubling down on the company’s values that you know matter. Finding those anchors the things that count and make consistent check-ins.
The other thing is make work a little easier and clearer when there’s so much else going on out in the world. The more you can make clear priorities, set an agenda that makes people know exactly what they need to be doing. If you can cut down on the noise and the distraction internally, that will help with the noise and the distraction externally. I do think this is something that everyone’s grappling with. It’s a huge cost. Wellbeing, stress and a lack of being able to focus has a huge business impact and needs to be a focus.
I’m delivering a talk to the women’s group over at GE Vernova about this very thing about crisis, communications and how to not make it more of a thing. How to determine and discern, which is the thing and which isn’t. Even if it isn’t, to your point, you need to acknowledge that.
Check in on people. That’s a big part of it because there are real costs.
I also think it ties into gaslighting in a weird way. Where a person all of a sudden thinks, “I’m the only person who’s thinking this. I must be crazy.”
There’s an acknowledgment that happens.
Charter’s Mission To Catalyze A New Era Of Dynamic Organizations
What a fascinating and such an important time now for your being, your Jena voice, but also Charter’s voice. What kinds of responsibility do you see like Charter? Having not just reflect the workplace but a role to reshape or help it evolve.
It’s a great question because Charter does. It’s a mission-driven organization. Our mission is to transform every workplace and catalyze a new era of dynamic organizations. A little bit about it. I just joined, but it was founded during the peak of the pandemic by a former journalist from the Wall Street Journal and one of the co-founders of Quartz, Kevin Delaney. Jay Lauf ,who’s been at amazing places like Wired in the Atlantic and Erin Grau, who will also has history at the New York Times.
They saw an opportunity to develop a product that focuses on the modern workplace and on what is actionable and what practical things you can do. Taking legitimate concrete ideas grounded, evidence and research and share that with their readers in a way that is journalistic. That is also speaking to the most forward thinking, most progressive companies. The ones who are trying to push for a better future of work. Does that mean we’re going to cover every single company out there? We’re not. We can’t. We can’t use our resources.
Find ways to ask people how they are or how they are doing. Double down on your company’s values that you know matter. Share on XNor should you.
What we want to be is almost like an ideal partner for our readers and how they can learn from some of the smartest both researchers and practitioners in the space that they work in.
To me, too, I see Charter is helping orient people. It’s because it’s helped centering. To your point, you’re looking there but it’s just a smidge. It opens the aperture or shifts the aperture. You can see what’s out there. I’m super excited and grateful for everything that you all are beginning to look at. Utmost respect for each and every mindset that you mentioned.
Thank you.
Hopeful Aspects Of The Future Of Work
Yourself included in that. With all that in mind, what gives you hope about the future of work? I’ll say both for everybody but also just for women who are looking for impact and also integrity.
I see a lot of choices being made by people to chart their own path, honestly. I saw some interesting data out of LinkedIn of how much a founder is one of the top job titles. People are like, “I’m going to figure out how to do this on my own.” Does that give me hope for organizations? I do think that companies will have to reckon with. People are finding their own way to write their own rules.
I also think we see in a younger workforce people who are leading with their values and with the things that matter to them. That gives me a lot of hope if we can find the pipelines and the career paths for them in our world that they are looking to lead with the things that matter to them. That may be that work-life balance or their values around the world and around climate. They’re setting those as priorities. That’s something that everyone could listen to.
People are finding their own way to write their own rules. Share on XIt makes me think of a story way back when I was at Inc. We did a whole story called the Apple Tree. It was about all the amazing companies that have gone on to be founded by people that used to work at Apple. It also coincides with the comment that you made about job huggers and people holding on to jobs so hard. Perhaps companies ought to take that philosophy of, we are a teaching ground. We’re going to enjoy, do our best or best in and out and be mutually advantageous, helpful and education-oriented to these future leaders.
When it’s their time to go and see because we’re prepping them. They’re going to go off and create the next and continue an ecosystem that’s more sustainable. That’s a cool legacy that old school companies could play. Will they do it? Is that Pines guy? Yes, absolutely. That’s how I roll. It would be nice. Maybe that next generation will be the ones that see it that way. Jena, Thank you so much. To be continued and perhaps maybe we can do some live journalism events in the years to come. I would love to do that but best of everything to you in Charter. I’m so grateful for you and all that you’re doing and revealing.
I’m thrilled to have the conversation. I can’t wait to follow the rest of your show, too.
Thanks so much. Until next time.
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Discussion Wrap-up And KB Takeaways
A fabulous conversation was such a smart person who got her finger on the pulse of so many things. She and Charter are doing such great work. Here are three things that I walk away from. Aside from scary numbers regarding women in the workplace. I don’t want to get distracted by that. Here’s some things.
As Charter says, what are actionable steps that you can take? The five Cs. Culture. Double down on it and pay attention to it. Two, check in. It seems basic but people don’t do it. It can even just be a walk around a floor pulse or a floor tempo with whom you work. Three, clarity. Provide it in terms of what you’re thinking, what the company is doing and what the values are and how you are in fact embodying them and modeling them. Four, communication and lastly, centering.
There’s so much that when it appears there are so many shoes dropping and everything seems in a state of crisis. Something’s a crisis. Some things are other people’s crises. It’s not your crisis, but they all need to be acknowledged, so state. When you see an elephant in the room, when you feel an elephant in the room, mention that, “I hear that stomping but here’s why we’re okay and why we’re safe.” The last C is choice. You always have a choice. It’s by how you respond, and react, participate or not in a situation that’s going on.
The things that as a leader to pay attention to, what are you doing with regard to the child care crisis, is a huge thing. Also, her point, is retention what we should be measuring in the workplace? Especially when people can’t even get into the job that they then want to go on to retain. I can say this because I am of a certain generation. Lastly, this whole new nation of job hugging. I know people need work. I get that and I do. Are there ways that you can parse out parts of your work so others can have a job at least and get their foot in the door? Think about it. With that, I look forward to the next Women Advancing conversation. Until then.
Important Links
- Jena McGregor on LinkedIn
- Charter
- Fast Company
- Washington Post
- Forbes
- Taylor Telford on LinkedIn
- Patagonia
- Brian Elliott on LinkedIn
- GE Vernova
- Kevin Delaney on LinkedIn
- The 2026 AI Summit
About Jena McGregor
Jena McGregor is the Managing Editor of Charter, where she leads the editorial team of the future-of-work media and events company. A longtime journalist covering leadership issues and the workplace, McGregor served as a senior editor at Forbes, where she oversaw future-of-work, leadership strategy, and careers coverage, creating the Forbes Future of Work Summit and its accompanying newsletter franchise.
Prior to that, she was a longtime workplace writer at The Washington Post and an editor and writer at BusinessWeek and Fast Company. Most recently, she was editorial director and vice president of content strategy at Modern Executive Solutions and its network of executive communities, M1. She is the recipient of the National Association of Black Journalists’ Salute to Excellence Award, two National Headliner Awards and a National Press Club Award.