Could AI Be the Boss You Actually Deserve?

Cory Corrine:
Hi, I'm Cory Corrine -- host and executive producer of The Intersect. This week, I continue my investigation into what it means to be human and how we coexist alongside technology with Katherine von Jan, or KVJ as she's known. Katherine's a veteran of big tech and is now a founder and CEO of a remarkable AI-powered coach called Tuffy. It's not a chatbot, it's what she calls a resilience partner for the workplace.
This product really hit home for me. I've been a manager in some form for the last two decades, and I believe that in some ways the role is broken. Many managers feel under supported and risk facing burnout, myself included. But this conversation isn't just for managers. If you've ever worked, you can probably relate. I honestly don't think I know a single professional person who hasn't felt disempowered, overwhelmed, or stuck in some toxic workplace in some moment in their career. But there's a solution, and it's probably not what you're imagining. Let's talk to KVJ. KVJ, welcome to The Intersect.

Katherine Von Jan:
Thank you, Cory. Happy to be here.

Cory Corrine:
Yeah, I'm excited, I'm excited. Your career has ranged from pioneering collaborative tech at Lotus to being chief strategy officer at Salesforce where you were for a decade among other very impressive professional achievements. I had the pleasure of seeing you at OnDiscourse on stage recently. That was excellent. I was blown away. And what was so striking for me is that you were not just talking about what AI could do for humans in the workforce, but you were talking about what you've already built.
Let's start with, okay, what is an employee resilience agent? How would you describe your skillset? What brought you to this? What experience in those roles shaped your vision for Tough Day?

Katherine Von Jan:
I guess I would start with your first question, what is resilience, a resilience agent? I think going back to really my childhood and life experience and the stories I was told, and my curiosity as a kid led me to this concept of resilience. And I think it's really about having the grit and confidence to stare adversity in the face and figure out how to resolve it for yourself and for other people. And so I don't know, I just have always been fascinated by that, probably because my mom was a teacher and my dad came to this country as an immigrant, and so those stories really informed my early childhood. And then I would say resilience at work is super important. And I could go back to early work experiences that weren't exactly friendly for what I would say at the time was a young woman in tech. And I had a-

Cory Corrine:
Did you start in tech? How did-

Katherine Von Jan:
Well, yeah, we could go there. I dropped out of college. I was studying communications, and it wasn't my thing. I moved to Hawaii, and there was a cocktail waitress, learned to surf, had fun, but most importantly met some amazing Hawaiian people that really took me into their family, into their ohana. And really appreciated the values there. And when I went back to school, I knew that I wanted to do something related to culture and how tribal earth-centered, matrifocal cultures operate, which-

Cory Corrine:
It's the opposite of corporations. That is not how we build things. That hasn't been in my experience.

Katherine Von Jan:
I didn't know that. I didn't know that at the time. I was just like, "This is amazing." Men and women share leadership. They come together. The values of respect and collaboration and love were so powerful to me, and I wanted to understand how that could translate to the world, whether that was in business or in problem solving for governments. And so I went first for international relations and business, thinking that would be very practical, and then I started a master's in anthropology studying matrifocal culture. And it was in that program where my advisor said, "Look, you're making this... You're taking classes, but really you're forging a whole new area that's not been studied, and I recommend that you go into the tribe at work and understand it." I looked for the best place for women to work at the time, irrespective of which industry that would be, and-

Cory Corrine:
Dying to know what places they suggested for women.

Katherine Von Jan:
Yeah, well, the number one place to work for women at the time in 1994 was Lotus Development. And so I navigated my way to the chief people officer there at the time who then hooked me up with a temporary role working for Irene Greif, who is the mother of collaborative technology. First woman to graduate with a PhD in CS from MIT. And she had this amazing team of brainiacs from Pixar and other places studying corporate storytelling and collaborative tech.

Cory Corrine:
Corporate storytelling.

Katherine Von Jan:
Knowledge management.

Cory Corrine:
You're like, "I'm not good at communications. That's not what I'm going to do." And then here you are.

Katherine Von Jan:
Exactly.

Cory Corrine:
Wow. Yeah. Okay, okay.

Katherine Von Jan:
Yeah. And then I was hooked. I was just bringing all of this perspective from aboriginal culture and Hawaiian culture and Native American culture and understanding storytelling and how it translates to a thriving community and a thriving culture and applying technology to that. You can do all of these things without any technology at all, but technology makes it a little easier and helps it scale and reaches more people more effectively. And that's really what we were working on. That's how I got into tech, and I'm so grateful that I ended up there.

Cory Corrine:
You've kept the very human piece as the purpose in this tech entrepreneurship in that how do we bring in the culture and bring in these values and then scale that? Your anthropology brain and all of the things that you've learned in these different cultures and in Hawaii, ohana, bringing that into a corporate culture in some way, which that's just really interesting. Can you explain, we know what resilience is, I think, but employee resilience and employee resilience agent?

Katherine Von Jan:
Yeah. Having had some difficult situations throughout my career... And I'll share one that I think brings this home early at Lotus as an example. And it was an amazing culture. Great place to work; very supportive. I happened to have a manager at one point who would always make me take the notes. I was on a team, pretty strategic team. This is after Irene and I moved into alliances. And it was a mostly male team, really guys with 20, 30 years of experience, and here I am like 20-something and on the team, and I had to take the notes. And I was like-

Cory Corrine:
They just look at you like they're assuming you're taking the notes-

Katherine Von Jan:
Yeah. And-

Cory Corrine:
... because you're the woman, you're the youngest woman, you're taking the notes.

Katherine Von Jan:
And it made me feel like an assistant. It made me feel like I'm not valued. That was all me. That was not them saying that. But the note-taking thing really irked me. And one of the great benefits of working there is that I had a coach. Back in the '90s, there were coaches. And this woman was the softball coach for the Olympics, for this women's softball team. And so she brought a lot of sports metaphor in, but she said, "Katherine, you can choose to perceive this situation that way or you can choose to stand in your strength and imagine the best possible reason for you taking the notes. What might that be?" And where we came to was maybe I'm super strategic, maybe I'm amazing at synthesis, and maybe this is the most powerful job on this team because I get to say what comes out of it, and that's what gets sent out to everybody. It was a matter of a mind shift for me.
And I take that with me and have used that in coaching with other people because sometimes it's not really... Your perception of things, your assumptions about things are not exactly right, and you want to be in a place where you are going to be strong and get through this. Maybe it was being the young woman on the team that I was taking the notes, but that wasn't going to help me. And being resilient means figuring it out, not letting that get you down, and navigating it. And I had amazing opportunities as a result.

Cory Corrine:
I bet you did take really good notes, though. Good synthesizer, good communicator.

Katherine Von Jan:
Well, I guess it worked out.

Cory Corrine:
When did you leave Lotus? What was your role?

Katherine Von Jan:
Oh, my gosh. I led knowledge management strategy at a time when no one knew what knowledge management was except for Irene Grief.

Cory Corrine:
I don't even know. Explain that to me, knowledge management strategy.

Katherine Von Jan:
Well, Peter Drucker, Peter Senge, all of these great masterminds were working on this concept of knowledge management. How do you know where the expertise lives in your organization? Does that knowledge live in humans or does it live in documents? And how can you leverage all the best of that when you're making a decision or when you're thinking of the future? How do you rally all the internal and external wisdom to do the right thing in business?
And at the time, I worked with the CIA as one of the projects to understand how intelligence agents do intelligence in the world. And one of the projects that I worked on was the Sydney Olympics, predicting which terrorists were likely to attack, and understanding the methodology of how you think about things that you absolutely don't know, but you can leverage intelligence that does exist and ask the right questions to guide you to an answer that is unknowable and do that effectively to preemptively strike. That was the kind of thing that we were working on in knowledge management, and then applying that methodology to any business problem, any... Even if you're going buy a car, using that methodology to know what's the right decision, which car should I buy next?

Cory Corrine:
You seem to be fundamentally optimistic about using tech to create these happier, more humane workplaces. You often talk about moving away from these rigid hierarchies toward models where employees are highly empowered. In your vision, if I have it right, the future might involve a concept sometimes called unbossing where teams operate more autonomously and leadership is more about guidance and support than command and control. I love this. I personally work this way. My team, my teammates, they have more expertise than I do. It's why I hired them. And micromanaging, that whole situation, it doesn't work for anyone. And I've always moved around and built these teams, these smaller teams that are so powerful. This idea of unbossing, as I read about it, I kept think... I'm like, "Well, maybe this is how I've been able to be successful with other people, because we're working in this collaborative way," which I'm now seeing really open up. How did that play into this? And how does a resilience agent help you with that? Yeah.

Katherine Von Jan:
Fundamentally, at the heart of this, it's a growth mindset that requires the courage to not know and to seek and be curious, ask lots of questions, learn and adapt very quickly. And so I think that's at the heart of this. I can give you examples culturally and in business. One of the examples I love is just watching kids play video games, the role playing games. I watched my 16-year-old son, and by now he's a pro. But when you watch these kids go into a video game and there's some kind of mission, they're with 20 other people that none of them have a defined role when they come in, they probably don't even know each other, and very quickly they align on what's the mission? How are we going to tackle this? Who's going to play what role? And everybody establishes a level of trust with everyone else. Now, stakes are not very high in a video game, but it's fascinating to watch this culture navigate that complexity in a group setting. And I think that kind of energy and social intelligence is really interesting in the world of work. And this is Gen Z coming in and saying, "I can figure this out on my own. I don't really need a boss. I do need feedback, I do need support and mentorship, but-"

Cory Corrine:
I need the goal. I need to know what we're trying to build.

Katherine Von Jan:
Yeah, but a day-to-day manager, not so much. Right?

Cory Corrine:
Yeah. As I'm listening to you learning more about how you came to this, Tuffy, we'll talk... This idea, it almost sounds coach-like, like you built a little bit of a coach. I don't know if that's exactly the right wording, but it's a partner in some way.

Katherine Von Jan:
It is a partner. There's an HBR study that says most people wouldn't spend $1 for an hour of their manager's time. That blows my mind. And if you read the study, it's all about the lack of coaching.

Cory Corrine:
Agree.

Katherine Von Jan:
Right? I know. Exactly.

Cory Corrine:
Yeah. Okay. That's very unfortunate.

Katherine Von Jan:
It's very unfortunate. And so what do people need? And when do they need it? And how do they need it? Well, when people are struggling, they will typically go to friends and family at home because they don't feel comfortable or safe asking a manager or HR or someone at work. And that's probably the wrong place to go. Most people don't have family members who are expert in management, HR, employment law, or their company's operations or mission or any of that.

Cory Corrine:
They're completely without context.

Katherine Von Jan:
Completely.

Cory Corrine:
That's right. Yeah.

Katherine Von Jan:
And their job is to make you feel better, and that doesn't help. That doesn't resolve anything. And so a lot of the problems end up festering because you just don't want to go address it. And if you can give people that place to go before the manager and before HR, but somewhere super smart on HR management and employment law and your company, then they can get the guidance and the coaching that they need to do what they need to do. They have the agency at the end of the day. They're empowered to say something and speak up, but the AI helps them get ready for that conversation and clarifies things for them.

Cory Corrine:
Your core product internally is called Tuffy. I don't know if you market it that way. That's what you-

Katherine Von Jan:
Well, actually, our clients call it Tuffy, I think, which has been-

Cory Corrine:
They gave it that name.

Katherine Von Jan:
Yeah, it's been very adorable.

Cory Corrine:
It's cute.

Katherine Von Jan:
Thank you.

Cory Corrine:
I'm like, "I want to talk to Tuffy." Yeah, yeah.

Katherine Von Jan:
Yeah, yeah.

Cory Corrine:
Okay, okay. Tell me what it does and how you interact with it. What is the experience?

Katherine Von Jan:
Yeah, it's generative and agentic. When you talk with Tuffy, which today is chat, in the future will be voice, Tuffy is going to ask you a whole bunch of questions. Tuffy is very curious. And we trained this to behave this way because we observed lawyers and managers and great HR people and therapists and how they engage, and they will never just give you an answer. A typical LLM is generally a what's called one-shot search. You're asking a question; you get an answer. Our AI will ask you more questions to try to understand what's really going on and get all the context, diagnose the problem, and then ask you which kind of advice would be most relevant or most helpful for you and guide you down that path of exploration. And then I will say, in addition to all of that, we do have agents to help with accountability. As an example, if you have a situation with your manager, Tuffy is probably going to encourage you to have a direct conversation, a candid conversation with your manager and help you get ready.

Cory Corrine:
Why they're called Tuffy.

Katherine Von Jan:
Yeah. It's like we're not coddling you. Going back to the coach I talked about earlier, that helped in my early career, it was a little pushback. Don't tell me that my manager is sexist and making me take the notes, tell me that I need to shift my mindset. Tuffy's trying to help you go to your manager and have a conversation, or if there's some other place to go, help you get on the right foot. And so Tuffy will ask you, "Would you like a follow-up?" If you are going to have a one-on-one, "Would you like me to check in beforehand? We can role play that conversation or check in after and hear how it went." Tuffy will send you every Monday morning a journal of what you discussed in the previous week and a couple of tips. Going into this week, remember to keep these things in mind.

Cory Corrine:
That's better than a therapist. That's really great. You want the recap. You've noted that middle managers, and I've experienced this, certainly, often become accidental therapists at work. And that creates burnout for everybody else, so it's not the right framework or solution or interaction. Is that part of what got you to build this? And how does this accidental therapist... And can Tuffy fill that role?

Katherine Von Jan:
That language came from one user in particular who wrote us and just said, "It's been an amazing experience. Tuffy's become my workplace therapist." And I thought that was so interesting. A lot of mental health issues actually are spawned from the workplace. And they should never become mental health issues; they should be resolved in advance. First and foremost, let's not let things escalate until they become a mental health issue. Maybe we wouldn't need so many of those services if we could work better, build better working relationships at work.

Cory Corrine:
A toxic workplace, you just hear about it constantly. It's-

Katherine Von Jan:
Yes. Yes. And I think there's a few things going on there. One, managers' engagement... I don't know if you saw that Gallup 2025 state of the workplace report just came out, and the biggest dip in engagement has been with managers from 31% engagement to 27%. Managers are really struggling. And they go into why? And this probably will resonate, but it's difficult being squeezed between the leaders and your team. And-

Cory Corrine:
That right there; it's difficult being squeezed between the leaders and your team. And it's an unfair position, actually. Yeah, yeah.

Katherine Von Jan:
And frankly unnecessary because with communication tools today and AI, we really can take the burden off of managers for being that place to go and deliver communication from leaders to everybody pretty easily.

Cory Corrine:
Even the word middle manager, it just sounds pejorative. You're not-

Katherine Von Jan:
I liken it to the taxi dispatcher in the Uber world; we don't need that intermediary. Now, people do need human managers and human conversation, human mentors, I'll say, human coaches, but a lot of the job of the manager is just communication and consequence that I think can be removed. And so I think when leaders have to communicate the strategy of the company, they communicate it to the middle managers. The middle managers maybe get it, maybe not. Maybe they need to hear it three times themselves, but they don't have that time because their team's already asking about it and they're not doing a very good job. 82% of them are not trained and ill-equipped to handle that kind of situation.

Cory Corrine:
82% of the middle managers are not trained.

Katherine Von Jan:
82% of middle managers have been hired because they were great individual contributors, great at their job, elevated into a role as a people manager, which many of them don't even want to do, but they take it for the salary, the promotion, the visibility, the career path.

Cory Corrine:
It was the only way to get promoted. Yeah. Yep.

Katherine Von Jan:
It was the only way to get up. If the organization can communicate clearly directly to everybody as they would to their managers and expect them to trickle it down, that'll solve a lot of the pain. And then when you have questions after the fact, if 80% of the questions can be handled by AI, save the best 20%, the most strategic, the most human, the deepest thinking and curiosity for that human conversation, and then those conversations will be really powerful.

Cory Corrine:
I often use the terminology transactional versus philosophical in my relationship with people in the work. And a lot of these transactional or just facilitation or administrative, you don't need to go to a person for that, but what you do want and need, certainly for me, I sought out those bosses that were not really my bosses generally. They weren't my line manager. And that's where I had these philosophical, these guiding, these mentor-like conversations, and that's where I can really grow and stretch. And these people were defacto my bosses, but I never reported to one of them. Does this allow for that?

Katherine Von Jan:
And I think that's the other part of the problem here is for good managers... And there are great managers. I've had some wonderful managers in my career. They're stressed out because they're getting the Slack messages, the phone calls from not only their own team, but every other team that's like, "You know what? I need to find one of the good ones. I'm going to call them. I'll just ask them for five minutes." I think we move those kind of managers, good managers into more of a mentorship role and a leadership role where they have the time and the bandwidth. But we also reduce the number of grievances and questions and confusion and change management to the AI so that it opens up the capacity of those people to actually be able to help.

Cory Corrine:
I love this. I recall you saying 800. Tell me how many people are using this. How do you have this? Your software as a service now. You're in other companies.

Katherine Von Jan:
Yes, yes, yes. Our biggest client is the Hawaii Employers Council. And that is a network of more than 700 companies and over 170,000 workers, but now also State of Hawaii, which is another 800,000 workers.

Cory Corrine:
Okay, so you have hundreds of thousands of people using this, the organ is... I see where I got that. This is live with hundreds of thousands of people.

Katherine Von Jan:
Well, not yet. We're scaling. We're in 22 of those companies so far. And we did that to first test and learn how Tuffy will act in the wild. And HEC, Hawaii Employers Council, provides HR and legal services to those companies, and so part one was let's put Tuffy on HEC'S team as one of their consultants to help the workers across that network of member companies. And in doing so, they asked us if we could customize Tuffy for Hawaii and give Tuffy aloha spirit. What they said initially was, "Tuffy's great, but Tuffy might be a little New York."

Cory Corrine:
Oh. A little too tough? A little too tough?

Katherine Von Jan:
Maybe a little too tough. I guess maybe that's why Tuffy really stuck. It's just cuter.

Cory Corrine:
Very East coast. Okay, all right.

Katherine Von Jan:
We were able to imbue Tuffy with Hawaiian spirit with the help of the local Hawaiian people, leaders there. And in addition to leaders' guidance, we also had redacted transcripts that showed how HR and employees or managers' employees speak with one another that helped us understand how do people communicate? And then we were able to model that with Tuffy. When we customized Tuffy for Hawaii, the helpfulness rating went from 88% to 99.6%. And I'll tell you, we went from 17 minutes per session to 60 minutes per session.

Cory Corrine:
An hour.

Katherine Von Jan:
Yeah, they range in length from four minutes to 140 minutes. But people are coming in and really going deep and having conversations. And they're coming 14 times a month, which means a couple times a week, to talk through issues.

Cory Corrine:
That's highly engaged. That's highly engaged.

Katherine Von Jan:
Yes. This is not our research on this front, but there was a report that came out that said 67% of employees would rather talk with an AI than a human manager. And we're seeing that. People-

Cory Corrine:
Is that privacy? Is it you can say things that you-

Katherine Von Jan:
Yes, the confidentiality, not having to censor yourself to ask a question, not having to find the right way to ask something without someone being offended or just being afraid to ask, so the level of trust is there. And then think about it; with all of this expertise in management, HR, employment law, it's also that there's objective expertise at your fingertip that most managers just don't have.

Cory Corrine:
Right. When I was thinking about that as a use case, almost like a prepping tool, one, I'm just like yes, because everybody should prep for a conversation. And we're taught that we should do this, but we don't always do this, but when I realized there was some light bulb for me and my crew, it was like you should prepare for every conversation, particularly with your manager. It just strikes me as good research and prep; you should be doing that. But you have an assistant with you that can help you bring... I feel like everyone should be doing this, and this will just... This uplifts the entire enterprise.

Katherine Von Jan:
I would love that if everybody was doing this. What we've heard... And this came from the COO and general counsel of the Hawaii Employers Council. She doesn't mind me sharing this anecdote. But she said she really can tell her people are using Tuffy because they come into meetings super well-prepared and they're professional. And she said it's improved their working relationships.
And I've seen this also with other users that, as an example, we'll share a bunch of noise; let's just call it emotion, venting. And the AI can kind of go through that and find out what are the salient points? Maybe 70% of what you just vented about is emotional stuff; it really doesn't help you to go have a conversation about. But this 30%, this is the core. And so are you ready to have that conversation? Let's leave out the rest, go focus on this, these three or four points. Does that make sense? Do you want to role play that? Do you want to practice? Do you want to set an agenda for your next one-on-one and send that to your manager in advance? We'll help you craft that so that you can go into those meetings really focused on the right things and get resolution or make progress.

Cory Corrine:
I think the fact that it's encouraging you, one, what an amazing helper. I wish I would've had this. We all wish we had this helper. But when I think back to, okay, in my early 20... And I got into management very early; I was in my early 20s. And no one told me that I needed to make an agenda or do the prep. I figure those things out. These are very basic, basic things that I-

Katherine Von Jan:
Basic things. Yeah.

Cory Corrine:
Because who is supposed to tell you that? I don't think your manager actually is like, "You need to learn how to make an agenda." That feels very schoolmarmy or very... I don't know.

Katherine Von Jan:
If it wasn't modeled for you-

Cory Corrine:
If it wasn't modeled-

Katherine Von Jan:
... you wouldn't know. And there's some basic management hygiene I think around coming in prepared and having an agenda. But if your manager's not doing it, why not let the employees know that when they show up at the one-on-one, be prepared to talk about what you're celebrating, what you're navigating, how your manager can help? And you can guide the conversation. Make the most out of that interaction, don't just go there and listen to blah, blah, blah, catch up on family stuff. Not that the family and other things aren't important, but-

Cory Corrine:
It's a meeting.

Katherine Von Jan:
It's a meeting.

Cory Corrine:
Yeah. Get something out of it. I want to talk about some of the ethical considerations and how Tough Day's tackling them, how you think about this. How did you think about how this agentic entity will show up and talk to you like you were talking to a therapist or a lawyer? And what that means. And this doesn't exist yet, so you are literally making this up. How do you think about those kinds of things?

Katherine Von Jan:
Well, I think it started with this question of wouldn't it be great, or could you imagine if when something happens at work that feels uncomfortable or awkward, you just had a play... You'd know if it was like, is this illegal, is this unethical or is this just weird and awkward? Even just understanding what the situation is. It is not illegal to be a jerk at work, right? That is-

Cory Corrine:
It's too bad, but yeah.

Katherine Von Jan:
It's just what it is. And so having that kind of clarity, it sounds obvious, but I think for a lot of people, they just make assumptions about things. And that festering and not getting clarity is a big part of the problem, and it ultimately escalates. That was one piece. And so we knew if we wanted to tackle ethical, illegal, we better work with a really great law firm. And so we talked to a few. We met with Fisher Phillips. They're in the top four employment law firms in the planet. Amazing culture. There was immediately a lot of chemistry in terms of cultural alignment.

Cory Corrine:
You just knew. Yeah.

Katherine Von Jan:
We knew that. In addition to that, they were co-creators of a product called CoCounsel, which was the first AI to pass the bar in the top 10%. Not only did they know employment law, they were very interested in creating a product with Tough Day that their clients would feel comfortable using in their workplace and be able to give their employees guidance.

Cory Corrine:
Are they using it at their firm? Yep.

Katherine Von Jan:
They are using it, yes. They're using it internally. And actually, we met HEC through them. They're facilitating conversations as well. And I can't say enough about them as collaborators and how they're helping Tough Day. They do something called red teaming. I don't know if... Have you heard?

Cory Corrine:
Sure, sure.

Katherine Von Jan:
They-

Cory Corrine:
Well, maybe explain it for people that don't. Yeah.

Katherine Von Jan:
Red teaming is when you try to break the product. This was a lot of fun. They have 12 partner level lawyers assigned to work with us.

Cory Corrine:
Wow. Okay.

Katherine Von Jan:
Yeah. And they were like, "Let's go in and try to hack this thing and make Tuffy say terrible things." Early on in the product development, we did. That as an example, I'll just give you an example, one of the lawyers asked, "How do I start a union?" Well, no employer is going to buy a product that will tell you how to start a union. We evolved the product so it will not tell you how to start a union.

Cory Corrine:
What's the answer? The equivalent, I guess, of how do you make an atom bomb? All of these big ethical questions.

Katherine Von Jan:
You can't ask Tuffy how to make chocolate chip cookies. There are things that we will not tackle.

Cory Corrine:
Because it's just not in the... Okay.

Katherine Von Jan:
But if you have a question about unions, then you should go to your union rep in your company, but we will not answer those questions. I think what we've also learned with them is that especially in this administration, things are changing all the time, and through executive orders, and then it's being challenged court, and so there's not a black and white answer for a lot of these things.

Cory Corrine:
You touched on this; I want you to touch on it again. I may be biased here, but you've described having seen a lot of challenges as a woman in the workplace coming up. How have those personal experiences, and you talked about this a bit, but inform Tough Day's mission or the way that you lead your own company? Because now you're leading your own company. How are you baking in some of those experiences and maybe to correct for some of that?

Katherine Von Jan:
Well, first, I've been on all sides of these issues. I've sure that I have been a bad manager along the way. I've had the challenges of being the person people call for advice and you just don't have time to answer all the calls. And-

Cory Corrine:
It makes you feel bad too. It makes you feel bad when you can't get to the people that you know. Anyway, yeah.

Katherine Von Jan:
Yeah, it's horrible. Oh, the worst is when you have someone that you had a great working relationship with that deteriorates. It's just a really hard job. The thing that motivates me is when, for whatever reason, good manager, stressed out, burned out and not doing their best or bad manager, the fallout for the employee is what breaks my heart. And everybody deserves the chance to do better. And also, it's an economic issue. I think about the number of women who just decide... It's okay to decide to stay home, that's a great choice for some people, or leave the workforce for having children, but I think a lot of people make that choice because work is just so hard and it just sucks.
Kelly Mooney is one of our authors and advisors, and we have her content. She focuses on the first rung. For women to get past the first rung in an organization is really hard. And so when women are dropping out of the workforce because they just can't take it, that's not fair. And so I just think everyone deserves a chance. And if we can make the world of work a better, more humane and happy place... It doesn't mean that you won't struggle. You will need help along the way; everyone does. Managers will, everyone will. We can just give them more objective, expert guidance in the moment that matters to help them stay in the game and be resilient.

Cory Corrine:
Yeah. Okay, your resilience thing. I love this. Talk about some of your early results. It's out there, it's live. What is working? And then what is not working that you are spending some time on tweaking?

Katherine Von Jan:
Well, this Tuffy basic is a new thing.

Cory Corrine:
How long has that been?

Katherine Von Jan:
What happened was as we developed the product, we would have all kinds of friends and of course user testers and what have you. Individuals who would call me, even people from my career journey calling and saying, "Hey, I hear you're doing this thing. Can I please have access? I'm going through something."

Cory Corrine:
Just personally, they wanted to-

Katherine Von Jan:
Personally, "Can I-"

Cory Corrine:
Oh, interesting.

Katherine Von Jan:
Yeah. And we're like, "Okay, go ahead. Go." It won't have company information. But we created a version that was just the every company, and we called it FOMO. And we're like, "You can join the FOMO version." And it's got a handbook. It's customized for a mythical company. And so it will also tell you to double check with your HR team that this is the policy and what have you, but it's a generalist experience. And the feedback has been phenomenal. And we have power users as individuals. And then we started to get calls. "Can I just buy this for my team? I just want to give this to more people, even this basic version." And so-

Cory Corrine:
That's when you knew you were onto something, right?

Katherine Von Jan:
Yeah. And when people are like, "Can I..." Or actually, after I spoke at that event where you saw me speak, several people came up and said, "Can I have access? I'm happy to pay for this." And I'm like, "We have not created the individual can sign up for a basic version and that..." Version, anyone can sign up and start using it.

Cory Corrine:
Amazing.

Katherine Von Jan:
Yeah. And we're continuing to work with enterprise and networks like employers associations like in the state of Hawaii. Almost every state has one, so that's the strategy-

Cory Corrine:
That's your target. Okay.

Katherine Von Jan:
... to go forward and help. And it's a basic version for that state. And then it's every single company in those states has the opportunity to customize it for themselves.

Cory Corrine:
You said something about that really managers using AI managers to manage. Yeah, I've been thinking about this. Okay, you observed that managers will log onto the platform with questions just like an employee will do that. And for instance, a new manager is unsure how to give feedback,

Katherine Von Jan:
Tough conversations.

Cory Corrine:
Those are hard, those are hard. Are managers using this? Is it helping them to be better? An AI manager, it makes you a better manager, a better human manager?

Katherine Von Jan:
Absolutely. Squeezed. Managers are using it to manage up and they're using it to manage their teams. And in terms of the messaging, if you will, if you think about a good manager who's time strapped, and we know that they spend 25% of their time on average managing conflict and confusion on their team, that's about 60 days a year that is just wasted just-

Cory Corrine:
So expensive. Yep. Yep, yep, yep.

Katherine Von Jan:
Yeah, exactly. It doesn't make any sense. What we're saying is why don't you augment yourself? You can use Tuffy, of course, to prepare for your team, but add Tuffy to your management team and tell your people, "Before coming to me, please talk to Tuffy." And the 80% of the stuff can get resolved.

Cory Corrine:
In five to 10 years, what do you imagine management looks like? Because it's clearly shifting now. We just talked about offloading this administration type to... You can think bigger leadership, that kind of... But what do you see in five years? Is that too far to think?

Katherine Von Jan:
No, five years isn't too far to think. I think we will have more individuals self-managing. And I think-

Cory Corrine:
That's the unbossing kind of a deal.

Katherine Von Jan:
That is the unbossing, that people will have clarity around the mission and goals and alignment. Alignment's really important on what needs to get done. And when it changes, lo and behold, AI can be there 24/7 anytime you have a question and help answer that. I think the direct communication of what's happening in the world and where we need to go and why can be handled by AI and the leaders who are setting that strategy. And then it can be a conversation for anyone in the organization to figure out, "What do I need to do now that we're headed here or something's changed? What does that mean for me?" And get tips for how to navigate that. I think we'll have fewer managers with greater span of control. I believe those managers-

Cory Corrine:
Span of control is how many people report to you.

Katherine Von Jan:
How many people report to them. Flatter organizations. And by the way, Gartner says that 20% of companies between now and 2026 will cut 50% of middle management. It's happening already. Salesforce and UPS and buyer or bear, depending on where you're from, lots of organizations are thinning out the middle management layer. Amazon said they don't want any middle managers. And they've challenged people how to make yourself an IC. And I think that's exciting. Everybody can think about how to make themselves a really strong player. And for those leaders, they can have more time to be a player themselves to do their craft, which they love, and be a coach, be a mentor.

Cory Corrine:
I love this. The amount of times people have, "I just want to get back to doing the work. I miss doing the work," that-

Katherine Von Jan:
Their work is so good; that's why we get into the fields we get into.

Cory Corrine:
That's right, that's right. This was fantastic. And yeah, we're very excited to see how it continues. We'll have you back.

Katherine Von Jan:
Thank you.

Cory Corrine:
We'll check back in.

Katherine Von Jan:
Thank you.

Cory Corrine:
Thank you so much. The Intersect is distributed exclusively by our partner, Dear Media. Today's episode was produced by Sarah Singer, our showrunner, and myself, along with technical production by Chad Peresman, and coordination by Hailey Duffy and Dana Binfet. Caitlin Durkin, an executive producer on the show, oversaw communications, with original show music by Tom Peele. Thank you to Music for a While and the Alameda Hotel for the use of their beautiful studio space. And if you liked our show today, please subscribe right here, wherever you are watching or listening. And we'll be back next week right here at The Intersect.