Your Best IC Shouldn’t Have to Become a Manager to Keep Growing

Jennifer Dulski:

One of the things that’s happening in this transition that we’re in, in this market, is we’ll have fewer managers. And a lot of the people, especially in certain functions where people were promoted to management just because they were good at their function, we won’t need to do that as much anymore. Like, some of those people never wanted to be managers in the first place, but that was the only way to grow their career, and that’s no longer true. So some of those really talented ICs will be able to stay and grow and do even more as an IC, which means we’ll have a smaller, better-equipped, and more passionate group of managers.

Steve Smith:

Hey everyone, welcome back to another episode of Work Tech Weekly. I’m Steve Smith, Managing Director of Growth at Rep Cap.

Every round of cost cutting seems to land on the same people. Middle managers. The ones who survive inherit bigger teams and get roughly the same support they got a decade ago. Which is to say, not much. The idea that managers don’t add value is wrong. We just never gave them what they needed to prove it.

My guest today is Jennifer Dulski, founder and CEO of Rising Team. Rising Team gives managers an AI leadership trainer that builds a personalized growth plan around each person and their team. Jennifer has spent more than 25 years in tech, including leadership roles at Yahoo and Facebook. She also teaches at Stanford’s Graduate School of Business.

We talk about why the annual engagement survey is on borrowed time. And why training managers in a room together only ever worked for about a third of the room.

We also get into the super manager. That’s someone leading 10 or 20 direct reports, with AI taking the administrative work off their plate. And we talk about why L&D has to start proving results instead of counting course completions.

If you manage managers, or sell to the people who do, this one is worth your time.

Let’s get into it.

Jennifer, welcome to the podcast.

Jennifer Dulski:

Thanks for having me. Great to be here.

Steve Smith:

It’s great to have you here. You know, and we were talking in the green room. I talk to a lot of impressive people in the space, but your resume is like right there at the top. You’ve had such an impressive career, and there’s a lot of things that I think are very current in this moment to touch on.

One of the things I did want to ask you before we dive into the rest of our conversation is, a lot has changed in our market over the past few years. When you work with tech and talent and people, it’s already a fast-moving arena, but it seems like it’s really hit the accelerator over the past few years.

Is there a question that you get asked now by CHROs or heads of people that you didn’t typically expect to get asked even a couple of years ago?

Jennifer Dulski:

You’re really right about this question, and as you mentioned, I have spent a long time working in tech. I’m now, gosh, more than 25 years, and over that time I’ve seen a lot of things change. You know, we literally went from like the dawning of the internet to the development of streaming and messaging and mobile apps.

Each time, I think we thought, wow, this is the biggest change. And none of those compare even close to what we’re seeing with the advent of AI. It has just turned everything upside down. It’s completely changed the way everything works, and it’s also a much faster change in terms of user adoption than any of those previous ones, because essentially anyone with a smartphone has access, which is everybody.

And so all of work has changed dramatically in the past three to five years, and that includes leadership development and all people-related content. And you know, I think the main question I get asked by people is just sheerly, how do I navigate this much change? It is a lot for people to handle, and a lot of that lands on kind of middle and early career managers who have very little training.

So it used to be, how do I support people to just become a manager? And that was already hard to do. And now it’s, how do I support them to be a manager of people in an age and an era where everything’s changing so much more quickly and people are really overwhelmed by that?

Steve Smith:

Absolutely. You know, kind of bringing in some of your career at this point, I mean, you know, you teach at the graduate business school at Stanford. You’ve spent time in the nonprofit sphere, worked at Yahoo, Change.org, Facebook. You were the first female entrepreneur to sell a startup to Google.

You know, it seems like one of the through lines of everything that you’ve been doing is working with people at scale, you know, managers. Even before this AI moment, it was a challenge for a lot of organizations. When did you first realize that it was specifically managers, and not just culture or engagement, that was really where you needed to focus your efforts on?

Jennifer Dulski:

Yeah, so the interesting thing is I don’t come out of the people space like a lot of folks do who start companies like the one I’ve started, which is Rising Team. I was actually a division leader inside these big companies, so I had, you know, teams of hundreds or sometimes thousands of people. And as an executive, I got a lot of support.

To your point, it was, you know, I had executive coaches, I was trained by incredible people. And what was hard was taking that kind of high-touch support that I had and scaling it out to my teams. And I remember especially, yeah, maybe 10 years ago, I just had so many managers coming to me saying, help, I need help.

And I didn’t have the budget, and I didn’t have the bandwidth to do anything that could really serve their needs. I mean, what I remember I did at the time was I hired an outside consultant who was great, and they came in and they ran a big, you know, thing for all the managers. We got them together in an offsite, and it was great for a day or two, and then they kind of went back to their day jobs and they didn’t really take anything forward. And I had spent a lot of money, and it just didn’t feel like it was sufficient.

And that was the aha moment that caused me to start Rising Team, is to say, what if we could deliver high-touch, really personalized support at scale, and do it in a way where not only do managers get support on their own, but they get the kind of help that they can bring back to their teams? Because that’s the key thing. It’s like putting them in a room together really only solves half the problem. What you need is to give them the tools.

I describe it like being taught to fish and then having to go back to the lake with a binder. You know, it’s like, what you need is the fishing pole. And so that was the genesis of Rising Team.

Steve Smith:

Well, and you’ve described Rising Team as the culmination of everything you’ve ever built, which, given your career, is a pretty bold claim. What does it mean in practice? I mean, what’s actually possible now that maybe wasn’t possible before?

Jennifer Dulski:

Yeah, it is incredible what’s possible. I have to say, even, you know, we started Rising Team in 2020, so I actually ideated the concept right before I knew there would be a global pandemic. And the original use case and set of products at Rising Team was about synchronous, interactive team-building sessions, so things managers could do on their own without having to hire a facilitator.

And that turned out to be very timely in a pandemic, because every team was separated and they needed to do things that would make them feel connected. What I always wanted to do, like if you look back at the very first outline I wrote for Rising Team, there was a section called Personalized Custom AI Coach, because my first startup was actually an AI company way back in 2009, 2010. We built the models ourselves. I actually remember the whole team, like, staying late, training the model.

And then I led a pretty big AI team at Facebook. So I knew what was possible. It wasn’t in 2020 really possible to do what I was envisioning, but as the LLMs came out and became available, what I dreamed of not only became possible, but it actually now is possible to do even more than what I dreamed.

So what we offer now, which our tool is called Artie, which is short for RT, Rising Team, it is a leadership personal trainer. So it essentially is just like what a fitness trainer does, but for your leadership muscle. So it gets to know each person. It does an intake with them, finding out their challenges, their goals. It then builds a completely custom, personalized growth plan for each individual. So no longer do we have cohorts of managers sitting in a classroom all learning the same thing at the same time. Every single person has a completely custom growth plan.

And then it includes all the modes that you might want. Not just coaching. It has coaching, but it also can do voice-to-voice role play. You can practice talking with another person. It plays as someone on your team because it gets to know your team. You can stop it in the middle and say things like, be more defensive, or, you know, coach me on this.

It will help you develop, you know, deliverables, like performance reviews. It then helps you with the team-building piece. So it is so much more dramatic, the kind of support we can offer people that we never could with internal HR, you know, teams alone or with outside facilitators and coaches.

Steve Smith:

And, you know, I guess another part of your pitch is really that, you know, managers can run science-backed team development workshops without a facilitator. Now, that sounds pretty great, but what’s really hard about making that work?

Jennifer Dulski:

Yeah. Well, it’s funny, because we get a lot of questions about, and sometimes pushback: I don’t think they’re ready to do this. I don’t think they can do it. And a hundred percent, I disagree with that. It is shocking to me how much anybody can do this if you just give them the right tools.

So if you think about it, we are a just-hit-go kind of platform. You pull up, let’s say it’s Appreciations, I hit go, everyone joins the session, and as I click next, they all see the same page, and all the activities are there. The timers are there.

Like, even if you do it badly. Like in the early days, we used to live test every session before we released it. We actually still do with new kits. We test them before we release them to the market. And I watched, you know, highly technical teams do these sessions exactly opposite of how we hoped. You know, they would keep their cameras off, they would, like, read silently to themselves instead of out loud.

And then at the end, I would think, oh my God, they’re gonna hate this. When they were asked for feedback, they said it was so great. We never have conversations like this. I can’t wait to do it.

So it doesn’t take perfection, it just takes intentionality. That’s all people care about. At the end of the day, they wanna feel seen, they wanna feel understood, and if we just take a tiny bit of time out of our day to do that, they will appreciate it, whether we are perfect or not.

Steve Smith:

Let’s shift gears a bit and talk about the market. You know, obviously you’ve been through some cycles in Silicon Valley. You’ve seen some phases, and it just seems like, you know, we are entering kind of just a bonkers era where everything that we thought we knew has been blown up. And it seems like the level of, not even just vaporware, just outright snake oil, is off the chart.

So when you kinda look at the L&D market broadly, you know, it’s huge, and it’s absolutely full of stuff that doesn’t work. So when you’re looking at the graveyard of failed management development programs, what does that look like from where you sit?

Jennifer Dulski:

Yeah, I think there’s two pieces of this. One is the sort of snake oil side that you’re talking about, and there’s always been snake oil. Now it’s a little easier to promote it and get it out to people and so forth. So you do have to be wary and cautious of that.

In the sort of set of things that genuinely have worked in the past, I believe that some of those things are likely to see an end, because what we can do now is so much better. So one example, and I wouldn’t have thought of this until I saw it, but one example is the classic engagement survey.

Right, so I am sure you’ve taken these. You know, almost every company we talk to has an engagement survey. They run them once or twice a year. It takes them months to synthesize the data and get back the results. When they get it back, they’re not sure how relevant it is anymore, ’cause time has passed. They give them out to all the leaders and managers. Nobody knows how to act on them. This was me inside these big companies.

I believe the engagement survey is about to die, because what happens when you give people tools like Artie is that you get real-time data and insights about what people are working on and dealing with and challenged by in the moment. So when I look at the kind of trend data that comes out of people using our tools, we can see these are the kinds of hard conversations people are practicing. These are the themes, like, you know, 40% of your company is saying they’re struggling with the AI transition. 30% says they still are having trouble delivering performance feedback. You know, some number of people say they’re not getting clear direction from the top.

Those things are happening in real time instead of waiting a year for them. And anyone, you know, anyone who put in a challenge is getting support, because they put it into their coach in the first place. So that’s an example of something that, I think we will look back five years from now and say, do you remember when we did engagement surveys? Maybe more than five years, but something like that.

A few other things that I believe are changing a lot. The second is cohort-based manager development. So there will always be some of this, similar to how there will always be some human executive coaches, which, you know, we’re not trying to replace human executive coaches. I think there is a real place for them. You know, there are so many talented coaches out there, and for executives who can afford them, it makes sense.

Cohort-based manager training may still happen, but it’s honestly very expensive. It’s either very expensive to do it in person, or it’s virtual and not very effective, and so we just won’t need that anymore. We will still bring managers together, potentially, for connection building, but we won’t have to train them in groups.

I compare it to, like, if you imagined you wanted to train a group of 50 people to run a triathlon, which is sort of like the equivalent of best-in-class leadership. If you put them all in a room, you’re going to have some people who are awesome swimmers, and other people who love to bike, and others who are runners. And we’re basically just teaching them the same thing at the same time, which is relevant for maybe a third. And so that, I believe, is also going away.

And then the other thing that’s been happening is sort of the self-paced video learning, where people do it on their own. And that, I believe, has been used as a way to try to offer something at scale, which then most people don’t actually use. I think many of those products see something like sub-10% usage, and for the 10% active learners who really still wanna do that, I believe those services are great. But companies won’t have to offer that anymore because now, again, if you can give a trainer to each person, it’s much more effective.

Steve Smith:

What’s your take on the current state of sort of like the learning and development in the talent market? It seems like just in the past few years, a lot of things have been blown up, and maybe that’s not a bad thing, because there was so much about it that was really performative and not really delivering value to, you know, managers, line-level employees, especially when you consider, you know, what you’re able to accomplish with Rising Team. Do you agree with that assessment?

Jennifer Dulski:

When you say there’s a lot of things that have been blown up, what comes to mind for you in that?

Steve Smith:

You know, the performance review. I think that looking at that, I think that getting into even learning and development plans, that there’s no way to measure exactly what’s going on in terms of the benefit. All you’re doing is notching course completions. Just seems like, you know, even with engagement surveys, there’s a lot of, we’re going to sculpt the survey so that we get to the answers we want, so that we can show the board, so that we can all, you know, get our bonuses or not get fired, or a little of both.

Jennifer Dulski:

Yes, that’s all true. From the very beginning of founding Rising Team, I said one of the things we’re gonna be rigorous about doing is measuring impact. Because to me, especially having been a division leader inside these companies, never would I wanna buy a product where the only thing I could measure was whether people used it. Like, so what if they use it? I need to know if I’m driving the impact that I want to.

So it is true, for the majority of time, most L&D products have measured their value in usage, course completion, you know, number of people who, maybe satisfaction might be there too, like people completed the course and then gave it some kind of rating. And we said we need to be able to do more than that.

So we have, since the beginning, measured test versus control and longitudinal movement in manager effectiveness scores. We do measure versus engagement surveys. So I can look at an engagement survey, and I can show you your scores with and without Rising Team, and how, based on how many Rising Team sessions you do, we see massive, statistically significant lifts there.

We also measure employee retention, and we can see whether, you know, we do this over the long haul, and we can see not just whether people report higher intent to stay, but whether they actually stay at their companies. And we see 33% increase in retention for people who do use Rising Team at least once anytime within the last month. And it’s still, even after a year, even if you haven’t used it within a year, it’s still driving something like 10% increase in retention.

And we’re just starting to measure also productivity gains. So we can look at things like customer success or IT teams actually resolve more issues when they use our product versus when they don’t. So my belief is that any L&D tool of the future, whatever it looks like, will need to measure true business outcomes rather than just usage.

Steve Smith:

You know, here’s a question about kind of this moment in the market where, you know, we both work in the tech industry. Certainly over the past year, two or three, there’s been, you know, a lot of, you know, layoffs, a lot of cost cutting, and it seems like disproportionately the axe falls on middle management. And it seems like management at that level gets a bad rap in terms of not adding value.

And you’re building a product that’s designed to help managers be more effective and improve team performance. When you look at what’s going on in the market and you look at that dynamic, what’s your take on that? Is it just like, well, this is a phase, you know, it’s unfortunate, but if we can provide better tools, we can really show that managers do provide a vital role? Or do you come to a different conclusion when you’re kinda looking at what you’re doing and how it connects to these broader themes?

Jennifer Dulski:

Yeah. Well, first of all, it’s a tough market. I, you know, I wanna be straight about that. And, you know, yeah, companies are just cutting a lot of people and jobs all around, and it’s a hard time to look for a job. And so I want to acknowledge the reality of that part of it.

I do believe it is sort of temporary. You know, all organizations are determining the way that humans and AI will work together in the future. And many of the companies who let people go are hiring back, just into different kinds of roles. And so I do believe the job market on the whole will continue to grow. I know there’s some people out there who think all of us are gonna work a, you know, 20-hour week, and machines will do the rest. And maybe that’s true. I couldn’t say.

What I believe is happening, though, for managers specifically, is that, you know, the idea that managers provide no value is a fallacy, I think. So if you look at the data that says 50% of people have quit a job because they didn’t like their manager, and also, on the opposite side, people will follow their manager from company to company. They will go to the mat, you know, fall on their sword for a great manager.

It is quite clear, if you ask a crowd of people, who here has had a bad manager, who has had a great manager, that really good managers are worth a lot inside companies. Even just purely for the task of, we have a vision at the top, how do we get it out in a way that people understand and incorporate into their daily lives? You need some layer to do that.

What’s happening now is that as you remove some of the layers of middle management, people are often getting bigger teams, and for the first time ever, I believe it is possible for managers to effectively manage larger teams. We call them super managers. You know, I used to say, like, no more than seven direct reports if you could avoid it. And now I believe, you know, we work with a lot of companies where there are 10, 20, et cetera, direct reports. And before AI tools, that would’ve been impossible to do well. Now it actually is possible if you do it well.

You basically say that a lot of the manual work managers do goes away because of AI. And McKinsey says it’s something like 18% of time that managers spend on purely administrative work, like writing reports to their manager or, you know, very basic one-on-one kind of tasks. So if you assume that AI can take away a lot of that and start doing, you know, even some of the basic management work, or even, to the degree managers are player-coaches, that it can do some of their player-type work, then it leaves more room for managers to do the front end and the back end, which is provide vision, clarity, help people understand what great looks like, really clear expectations.

I actually call this the three Cs of being a great manager: clarify, coach, connect. So clarify is, what does good look like? Coach is, how do I understand each person on my team, what they’re great at, and how to leverage them to their maximum potential and help them grow? And connect is, how do I make this feel like a team? So the more that AI can take any manual, administrative, IC-type work off your plate, the more managers can spend on the three Cs.

Steve Smith:

You know, if the long-term vision is a world where every manager has the kind of development that used to only be reserved for top executives, what does that change, you know, from a people standpoint? You’ve made the connection to, you know, the ROI story of, okay, connect to business outcomes, and that’s interesting and compelling. But what does it mean for that, you know, first-time manager who is still trying to find their way, or even a mid-career professional who is trying to, you know, get to that next step in their career?

Jennifer Dulski:

Yeah. Well, if you think about it, the vision of Rising Team is actually not about managers. It’s about the workforce that works with the manager. So we believe in a world where everyone in the workforce feels deeply understood, supported, and empowered to reach their goals. And that’s what happens when you have truly great managers, is you get an empowered and supported workforce.

And then your business outcomes are so much better. People, I mean, all the things we were talking about before, but they stay at your company because they’re loyal to you and your mission, and your company is more successful. And also the world’s just better because people feel understood. Wouldn’t we all like to be understood?

And for the managers themselves, you know, what I’ve always said about Rising Team is I believe we can turn good managers into amazing ones by giving them the right support. And I believe we can turn mediocre managers into really good managers, and I believe we can help poor managers either decide that they wanna do it and become great managers, or decide that they’re not meant to be a manager, which is okay.

One of the things that’s happening in this transition that we’re in, in this market, is we’ll have fewer managers. And a lot of the people, especially in certain functions where people were promoted to management just because they were good at their function, we won’t need to do that as much anymore. Like, some of those people never wanted to be managers in the first place, but that was the only way to grow their career, and that’s no longer true. So some of those really talented ICs will be able to stay and grow and do even more as an IC, which means we’ll have a smaller and better equipped and more passionate group of managers.

Steve Smith:

Oh, and that actually gets to a question I was thinking about, and you partially answered, is just like, there’s sort of, I guess, it’s almost a stereotype of an outstanding individual contributor who is amazing and gets put into a management role, and they are just catastrophically terrible at it.

Is it that individual just didn’t want to do it in the first place and should have just remained an IC? Or is it that an amazing, talented person, and they just didn’t have the right support that maybe now is actually possible?

Jennifer Dulski:

Yes, both are true. So two things happen here. One is that first-time managers get very little support. So even people who might be naturally good at it, with no support, no training, et cetera, may not be their best because, you know, it’s like the first time you do anything. I know I was probably a better parent of my second child than my first one. So, although I watched the first one like a hawk more, so I don’t know.

So yes, all brand-new managers are under-supported. And now with tools like Artie, there’s no excuse for that anymore, because it is incredibly affordable to support them in a way that is even better than what we could do before, and much cheaper.

The second thing is also true, because everybody has natural talent. So we have this exercise in Rising Team where you take an assessment, and it helps you identify the things that really bring you joy and energy and come easily to you, versus the things that you may be good at but really drain you. And everybody gets, like, a spider chart of their natural talents.

And there is a talent on there called Cultivate, which is the talent of loving to help people grow and develop and bring teams together. Anyone who has that, from any function, can be a great manager. If that’s all the way in for you, then you’re never gonna love being a manager. You’re just not. And that’s okay. And so we really should try to put people in roles that align with their natural talents. They will be happier and more successful, and so will the company.

Steve Smith:

Jennifer Dulski, this has been a fantastic conversation. Thanks so much for joining us and sharing a lot of very interesting perspectives with our audience.

Jennifer Dulski:

Thanks so much for having me.

Steve Smith:

Manager development has been treated like an event for as long as I can remember. Get everyone offsite for a day or two, then send them back to their desks. By the following week, most of it is gone.

The people who pay for that are first-time managers. A lot of them were great individual contributors who took the job because it was the only way up. They got a title and a team. Nobody gave them much else.

That model is done. It just hasn’t been replaced everywhere yet.

The kind of support that used to be reserved for executives can now reach every manager, every day. And when AI handles the administrative work, managers get time back for the parts of the job that actually matter. Being clear about what good looks like. Knowing each person well enough to help them grow.

There’s a quieter shift here too. Fewer people will need to become managers just to build a career. The ones who do will be the ones who want it.

The case against middle management was built on managers who never got real support. Give them that support, and the case gets a lot harder to make.

If you enjoyed this episode, make sure to subscribe to Work Tech Weekly on Apple Podcasts, Spotify, or YouTube. And I’ll see you next time.