How to develop leaders in a distributed, AI-augmented world

Kameko Leung (00:00):

We need to start asking leaders to not just be task managers. What we really need managers to start to become our process experts who can go in and look at the way a team is functioning and look at the tools in which we’re using and also engage the team in this conversation as well about what should AI be doing? What could AI do that’s going to make things easier and take less time for you?

Hannah Beaver (00:32):

You’re listening to How to Make A Leader, a leadership development podcast from Big Think Plus where we take the best ideas from the biggest minds in learning and development and distill them into actionable insights. I’m your host, Hannah Beva. The world of work is distributed in many ways across geographies, time zones, and today we’re seeing that distribution across both human and AI teammates. Developing leaders who can thrive in that environment is what my guest today does best. Kameko Leung is a leadership development professional with over a decade of experience across tech, recruiting, and the nonprofit sectors. She has built manager development programs at Zillow and Michael Page and currently designs leadership programs at Pinterest. Today we’ll get into how leadership has to evolve when your team is distributed, AI augmented, and not the same reality that it used to be. Kameko, thank you so much for joining us and thank you in advance for all the wisdom that I know you’re about to drop on us today.

Kameko Leung (01:41):

I hope I can say something helpful for

Hannah Beaver (01:44):

Someone out there, but

Kameko Leung (01:45):

Thank you for having me. Of course,

Hannah Beaver (01:47):

Of course. So I’m going to drop you on the defend and start with a hard question, but a question that I think is going to inform the entire conversation today and that many I think listening can relate to. And so my question for you first is what do you think is the hardest part about developing leaders inside a distributed organization?

Kameko Leung (02:07):

I think the first thing I always like to start with is that we think about distributed leadership and leading remotely as being this new thing that started six years ago in the pandemic. And the reality is that it’s not. I’ve thought back to my managers and I don’t think I’ve ever had a manager who’s physically located in the same office as I was and that this is many, many years ago. And so I think first of all, just getting comfortable with the idea that this is not new, but what is new are the tools that we’re using, the environment that people are working in, the fact that it’s at scale and that people are working at home, they’re not just working in a different office, which is quite different. Those are the things that make it really challenging and especially certain teams, if certain teams were historically all grouped together like sales for example, it’s really difficult to recreate and your home office, that environment of being in a bullpen with everybody making calls together and going and ringing the bell when they make the sale.

(03:08):

So it’s that kind of stuff. How do you create an environment where people feel connected yet they’re sitting often by themselves at home, maybe in a coffee shop, it’s still with their headphones on, not really engaging with those around them. How do you still create that environment of connection though we’re all distributed in different locations?

Hannah Beaver (03:28):

And then is there anything that you think organizations consistently get wrong when they try to develop leaders across a distributed team?

Kameko Leung (03:34):

For most L&D teams that I’ve worked with, we’re still trying to run trainings the way that it worked in the past and we are in a very different world now. So what I mean by that is that we say, “Okay, here are the key concepts that I want these leaders or these managers to learn and here are the frameworks we need to cover and here’s the HR practices that we need to get done.” And in the end there’s maybe 10 minutes for breakout activity every 30 minutes or so. That’s not enough time for managers to actually create the connections that they need to really start building and collaborating cross-functionally. And that’s what’s really important when you’re working in a distributed workforce is people’s ability to quickly establish trust with each other, connect with each other, and then be able to work cross-functionally when they leave that room with some pretty good standards and ways of working.

(04:30):

The other piece of that too is that I’m saying we focus so much on these frameworks and these concepts we want people to learn. When we also know that most learning happens in the flow of work, in the day-to-day actions and challenges people are running into. So what I’d really like to see or hope to see more of in the future is that we start to, when we spend time as a group bringing managers together, we start to have them actually work on real problems that they’re facing. Yes, we can have a framework or a concept that we want to make sure that they put into practice, but do it within the context of what is actually going on for them right now as managers and help give them the time and space to actually work through it together.

Hannah Beaver (05:12):

I love that. And I’m excited to hear about how you approach that specifically. So let’s kind of talk about your approach as we think about distributed teams. I know you obviously have a wealth of experience in this area. So you’ve mentioned before that you think distributed teams need an operating system. What do you mean by that?

Kameko Leung (05:28):

I love this term operating system too, because when we’re thinking about just how do we work together, that’s really what it is. It’s how we’ve agreed to operate as a group of people. But where I think we get it a litle bit wrong or managers I’ve seen get it a little bit wrong is they think, “Oh, I’m the one that needs to come up with this operating system. I’m the one that needs to execute the operating system.” And there’s not a lot of buy-in usually when that happens. When a manager says, “Here’s how we’re all going to function.” What usually happens is that’s the way that the manager works really well and that’s not necessarily the way that everybody else works really well. So when I’ve seen this be the most successful, managers take time upfront to sit down with the team and say, “Okay, first of all, let’s look at where we’re all located.

(06:12):

Are we all able to actively engage in conversations and problem solving at the same time? What are our core working hours going to be or what are our agreements upon if we have to get input from the group, how much headway or lead time are we going to give people so that everyone can participate?” Doing things like that and having that conversation as a group upfront really involves everybody and then everyone holds each other accountable. But then the second area of opportunity that I see a lot of managers run into is they think they’ve set these working agreements or these operating systems and it’s like set it and forget it. It’s all functioning the way that I hoped it would, which never happens. At some point there’s going to be somebody who either pushes the boundaries of the agreed upon operating agreements or misunderstanding. I think it’s more often a misunderstanding than anything else and that’s where the manager needs to be ready to come and step in and hold the team accountable for what we’ve all agreed to.

(07:07):

To give you a quick example of this, I had a team that I was working with prior to the pandemic, but we were all located all across the country in the US, from California all the way New York. And we had agreed upon core working hours of 10:00 to 2:00 to make sure that everyone could participate in any challenges we were running into. But we had one team member who consistently in New York, when they wanted a certain outcome to go their way, they would start the conversation three hours ahead of everybody or three hours of us on the Pacific time zone. And then our manager was located in central time zone. So by the time anyone in PT was able to get on and contribute to the conversation, all decisions had already been made. My manager at the time was like, “Well, if you have a problem with the way this is happening, make sure that you bring it up to this individual.” And that’s fine, but as a manager, you also need to reset the expectations and standards with the group because otherwise you’re allowing this or permitting it and saying, “This is okay.

(08:08):

This behavior and the way of working is okay.”

Hannah Beaver (08:11):

What does a manager have to do differently to build camaraderie and trust across a team that has never met in person or has that once or twice a year team retreat in person?

Kameko Leung (08:21):

When you think about when you meet somebody for the first time in real life, it’s not like within five minutes you are sharing all your deepest, darkest secrets with them. It takes time to build trust with people and to build psychological safety amongst a group of people and it takes repeated action and proof of behavior in order for people to truly trust each other. It just helps you to be a little more patient, I think. And so if managers can start with being patient, but also teaching their teams to be patient and teaching their teams to say, “Okay, let’s check on the reality of our relationships with each other.” And what I mean by that is I personally feel like I can create friendships very quickly and build trusting relationships very quickly, but I have overestimated that before and there have been times where I’ve thought that there was more trust in the relationship than there actually was and then I’ve stepped in it.

(09:12):

I’ve given feedback in a way that was too direct that was taken as offensive to the person that I was working with and then the goal was not reached, of course, because I was not giving feedback in a way that was appropriate for that relationship. So taking the time as a manager to take a step back and say, “Okay, what is the status of our relationships? Are we rock solid? Are we still building? Is it very tenuous? And then how do we make those relationships stronger is a great starting point.” Taking the time upfront to also allow for people to share a little bit about who they are as human beings and not just employees is important. And I think a lot of people do this, but we’ve also kind of gotten into this mindset of, “Oh, this looks like a check-in question at the beginning of our team meeting.” And some people are more or less comfortable with that.

(10:01):

I think where you really start to see some camaraderie building is when you start to have fun challenges or you do things that are not necessarily about people sharing all of their personal experiences, but starting to create shared memories. For example, when I was working at Zillow, our learning and development team was quite large. We did a regular trivia session using Kahoot and the people who set up the trivia session, they had so much fun with it, but the trivia was stuff that we could all have banter about and we could all laugh about. And then later we would take those jokes into other meetings in the future or Slack messages with each other. So those are creating some shared memories and comradery versus a check-in question is getting to know people on a more personal level whether they like it or not. There’s a balance I think that can happen But not solely relying on the check-in question is pretty important.

Hannah Beaver (10:59):

And again, there may not be a silver bullet for this question, but I want to think more specifically around leadership. So how do you develop a leadership instinct in someone who isn’t physically around great leaders, they’re experiencing their managers and their leaders in those little check-in sessions, but they’re not getting to experience the full essence of leadership from them.

Kameko Leung (11:21):

That is really hard. And that is something that I’ve repeatedly heard feedback on from managers saying, “I feel like I’m missing being able to just kind of see behind the curtain.” We actually have a lot, I would say, a lot of ownership on being able to create those experiences of seeing behind the curtain, whether you are in learning and development or not. So if somebody is saying, “Hey, I want to explore people management, or I am trying to understand what that next level of leadership looks like. ” First of all, as a leader, you should have the competence to be able to say that that is what you’re trying to achieve in your career. So step one, you need to say that that’s what you need. But step two, if you are hearing that from your direct reports, actually inviting them to almost ride along with you in a virtual environment, maybe it might be, “Okay, here’s how I’m setting up my day.

(12:09):

Come take a look at how I’m actually structuring. These are all these things that are coming at me. Here’s how I’m prioritizing or thinking about this today.” Or, “Hey, come to this meeting. You get to join this meeting where we’re actually talking about, let’s say our strategy and of course appropriate meetings for that individual to be a part of and shadow along and then answering questions afterwards.” Those are opportunities where you can have somebody who’s maybe a direct report or a mentee of yours that can actively participate and learn alongside you. The other thing that though from a learning and development perspective, one of the best programs I think I ever got the opportunity to run was for an aspiring leaders program at Zillow. And the reason this was so effective was, yes, they came into a classroom setting to learn frameworks and learn concepts and everything, but they were required to have two mentees that they were working with throughout the program and that required them to actually put into practice the things that we were talking about and then we would discuss as a group what was going on with your mentees, how did this work when you tried X, Y, Z concept?

(13:12):

Having that real life hands-on experience allowed for them to say, “Do I actually even like doing this? D I like people enough to manage others?” And it was a very low stakes environment because if it turned out that wasn’t going to be something that they enjoyed or not being able to influence because they didn’t have the authority over that particular individual, that’s a whole different challenge that folks have to navigate as well. It was a really great opportunity for them to say like, “Is this actually something I want to do? ” And then learn from their peers and then also learn from their mentors about other ways that they could handle certain situations.

Hannah Beaver (13:50):

I want to dig deeper into what this means in practice. How do you design a leadership development program that prepares people for leading in a distributed and I’ll use the term for the first time today, AI augmented world?

Kameko Leung (14:07):

Oh my goodness. I think that right now that AI augmented world piece is going to be the next big challenge for sure. Again, I do think that from what I’m seeing right now, most learning professionals really want to get this right and there’s a lot of fear of doing something outside the norm or not creating a strong enough foundation of skills for leaders to build off of in order to start thinking about some of these more advanced skills that we need to learn. I recently did a post about this that I do think that there are some skills right now that we are not paying enough attention to being in an AI augmented world. For example, just because we have AI doesn’t mean that what the AI produces is great. We’ve all seen this. We’ve seen AI slop all over social media, but it shows up as workslop as well, especially when the expectation is, okay, everyone just needs to utilize AI.

(15:07):

And when people are still trying to figure out, well, how do I use AI in a way that’s actually going to help me, but I also need to meet the company expectation of just using it period. You get a lot of junk that comes out and a lot of wasted time on everybody’s part. So we’re in this kind of messy middle part right now where everyone’s learning the tools. Managers also are learning right alongside trying to hold people accountable of using them. It’s a funky place. So I think if we start to create some space for managers to learn a few things. One, let’s get back to the basics of critical thinking. What should AI be doing and what should humans be doing? How do we evaluate the AI product to say, is this actually the high quality that we’re looking for or is this a little quick and lazy?

(15:53):

Is this actually what we need to be moving forward with? Also, coming back and saying, okay, let’s look at job functions as a whole. Let’s look at my team as a whole. There are things that could be automated that would make work faster and that’s going to take away parts of people’s jobs and that’s going to be uncomfortable for them. But where does that now open up their time and capacity to do things that are uniquely human or that are going to be done better by a human with the assistive AI? That’s something that I would love to help managers dig into a little bit more as well. So there’s just going to be a different set of skills ultimately that I think we need to start thinking about in order to develop leaders for the future. Does that mean that we have to stop working on the basics like giving and receiving feedback?

(16:41):

No, because in execution, that’s still hard, but now we have really great tools that help you prepare for those conversations. So now it could be changing the way we approach that and saying, “Let’s use this tool to help prep.” Now you go and practice with each other.

Hannah Beaver (16:54):

And then I’m curious, do you have an example or a success story perhaps from your time at Pinterest where you’re seeing this in action and you’re seeing this kind of beginning to take place?

Kameko Leung (17:04):

I have an example from a few different places that I’ve used and that’s been working really well. I think feedback is a perfect example here of a skill that we’re starting to up level using AI and using the way that we’re training around it. So most folks, when they come into a manager training, it’s not the first time that they’ve ever had any kind of feedback training, but you’re starting to think about it from a different perspective as a people manager. I’ve had quite a few folks who I’ve gone through feedback training with recently where we’ve said, “Okay, you know this feedback model. Great, but let’s use AI to get feedback on your feedback and then put it into practice.” And so what I’ve done is I’ve actually been able to help them build out a prompt of doing a role play with their AI technology where they can practice their feedback and then they say, “Okay, let’s pause this role play.

(17:57):

AI, tell me what would make this feedback better?” Or, “Where are some opportunities that I have to be a little bit more clear or more actionable? Is there any language I’m using that could be misinterpreted or seen as bias in some way?” And then we go and actually practice this with a human being. And what I’ve been hearing from my program participants when we do it this way is they’re coming into their role play practice way more confident. So they’re not kind of like fumbling, stuttering over their words quite so much and they’re also coming in with a lot more clarity. And then when they come back and talk about, “Okay, how did that role play go with other human?” They say, “Yeah, that was a lot more clear, a lot more action oriented. I felt like I could do something with that feedback.” And that’s, I think, where we always have the biggest opportunity is people walk away from a feedback conversation feeling defensive rather than inspired to act.

Hannah Beaver (18:55):

And then what is the one must have that you would build into a leadership program or system today regardless of the industry or company size?

Kameko Leung (19:05):

So one thing I would build into any program today is something called a coaching circle. I’m sure a lot of people have heard of coaching circles before, but I think it’s more important now than ever because it’s not only a way to actively problem solve as a group, but it’s a way to build deeper connections for managers in this group. The way this works is that everyone comes, it brings a problem with them, some kind of challenge that they’re running into. It usually works best when you have a group that’s kind of in similar spheres. For example, putting engineering product and design together and then putting maybe sales and marketing together and then people teams together, just because there’s a little bit more context. And then letting them choose which problem do they want to solve. So it gives them a lot more agency as managers to choose the problems that are the most relevant and useful for them.

(20:01):

And then as a group, they brainstorm, they provide advice to the person who actually is running into that challenge in real life right now. And the feedback that we’ve heard when we’ve done this is that that person who got the advice, they’re like, “Man, I felt so supported.” And I was getting feedback from people who I didn’t think I would necessarily get great ideas from. I’ve never worked with them before. They don’t know my team, but they understood the challenge I was facing as a manager and that was really important. And then we see in the chats usually after these types of activities, people say, “Hey, I’m going to put up time on your calendar to continue this conversation.” And as a learning professional, that is such a win. When you see in the chat they’re saying, “Let’s keep this conversation going. ” You know that you are driving those connections and you can create some frameworks or guidelines around these coaching circles.

(20:54):

You can say, “Okay, everyone, today we’re going to have a coaching circle specifically about job design. What challenges are you running into around job design? Go.” And that’ll help narrow the focus a little bit so that we’re able to still apply some of the key concepts that maybe we need this group to get, but they are also able to work on things that are relevant to them.

Hannah Beaver (21:15):

So getting deeper into the AI layer, taking it to the next level, today we’re seeing more and more managers are overseeing teams that also include AI agents alongside people. So they’re not just people managers, they’re overseeing an AI agent as well. How does that change what good leadership looks like?

Kameko Leung (21:34):

We need to start asking leaders to not just be task managers, which hopefully they’re not just being task managers to begin with, but that’s a common trap a lot of, especially new managers and even managers at senior levels who might have a lot of scrutiny on their work may fall into where they are just delegating out tasks and saying, “You complete this and you complete that. ” That’s going to become more and more less valuable, I would say, as time goes on. What we really need managers to start to become our process experts who can go in and look at the way a team is functioning and look at the tools in which we’re using and also engage the team in this conversation as well about again, what should AI be doing? What could AI do that’s going to make things easier and take less time for you?

(22:24):

And what are those things that you really need to be focusing on? And if you have extra time, what does that actually free you up to do? Does that allow for you to think more strategically? Does that allow for you to spend a little bit more time thinking about the specific execution of work and where you’re going to need to lean in or go build better relationships or does that create more time for you to go out there and learn because we’re all learning at the speed of light right now, but that’s what I think managers now are going to really need to start to lean into in terms of skills when you’ve got AI agents as part of your team is thinking about the larger process and not just being so reactive to the things that are coming your way.

Hannah Beaver (23:04):

Do you have an example to share that?

Kameko Leung (23:06):

Well, I can say that my team right now, we are doing that looking at where does it make sense to be using an AI agent to enhance the quality or the speed or efficiency of our work? But I’m actually going to take it outside of a corporate setting here as my shameless plug for mine and my husband’s business. So we purchased a small business in the last year called the Seattle Barkery. So if you’re in Seattle, come get dog treats or dog cakes for your favorite for a friend. It’s a perfect example of why millennials are doing really well with taking over these businesses from folks who are ready to walk away from them. These businesses are not up to scratch per se with using the latest technology. An example we see right away, we get all of these customer service requests that are coming in all the time and we don’t have a dedicated customer service professional on our team.

(23:58):

It’s a small business, it’s a retail operation. And so this is a perfect case for using an AI agent and creating a customer service bot that can answer some of your basic questions, but do it in the tone of the owners.

Hannah Beaver (24:14):

And then as we think about working well with AI and integrating AI into the workflow, what does getting it right look like? What is the shift that you see in a leader who is genuinely working well with AI and not just using it?

Kameko Leung (24:28):

I think first understanding what AI does well and what AI does not do well is really helpful. There’s been some research recently that came out from Gartner and from McKinsey that talked about why there’s this big push, this top down push to use AI is because very senior leaders see the opportunity and the potential, but they’re less connected to the day-to-day execution and operations that are happening in the business. And so where AI tends to thrive right now is in a lot of that strategic thought partnership, that brainstorming, that challenging in a way that’s safe, whatever though the leader may potentially be having. Things are moving so fast, tools are improving so much. And I think about, I was looking at recently at what I put into ChatGPT maybe three years ago and I was like, write a limerick about dot, dot, dot. And that’s how we were using it three years ago and today I might use it to say, be a thought partner for me while I try to figure out an exercise that’s going to generate these goals and outcomes for this team.

(25:35):

It has the sophistication now, so who knows what it’s going to be a year from now or two years from now.

Hannah Beaver (25:40):

And then as we talk about AI and our roles materially changing, what does that mean for the future of L&D roles that you’ve seen?

Kameko Leung (25:49):

So I did a post about this recently. I had someone who reached out to me who was really frustrated in their job search and they were saying, “I just think L&D roles are disappearing. I think this is an industry is going away and we’re not going to see as many L&D opportunities in the future.” And I challenge that a bit because what I think we are actually seeing is roles that we would traditionally think of in L&D. They are evolving and their titles are changing and we may not necessarily know to look for them. I had someone, for example, in the comments section who got really riled up when I said instructional design positions, traditional instructional design positions were evolving to learning experience design positions. And there’s a really distinct difference here because when you work with larger L&D organizations, instructional design is often its own team and it’s a really important team.

(26:46):

They do a lot of really valuable work, but often the way it’s been designed is they’ll get a request that comes in that they then need to turn around and execute, whether it be designing a specific training, designing an e-learning, but it’s very specific usually. It’s not looking programmatically for beginning to end on how somebody learns. We traditionally think of them as more of a program manager. And now we’re starting to see that shift of truly a learning experience designer thinking, okay, if I’m going to help this person learn X, Y, Z skills, what are all the different ways in which I can connect them to this overall experience? For example, maybe we start with this e-learning, but we pull it in then to this live training where we discuss the e-learning and then they take it back and work with their manager and put it into practice and then we come back and touchpoint again in a different way.

(27:37):

If you don’t know what words to be looking for, it’s going to feel like these roles are disappearing. The only way you’re going to know the words to look for is to stay relevant and on top of the skills.

Hannah Beaver (27:47):

And then the last question that I have for you today is what is the best piece of leadership advice that you’ve ever received?

Kameko Leung (27:53):

I’ve received really great advice from leaders that I’ve worked with before saying you need to provide proof of behavior before assuming that they’re going to assume best intent from you, especially in a virtual environment. There’s so many little instances that your team and your peers are getting insight into, can they trust you to fulfill the work that you are being asked to do? Can they trust you when you think about how you solve problems or make decisions? Can they trust you to communicate with them in a timely manner and be considerate of their working styles and needs as well? All these little moments we have throughout the day are determining how strong the trust is between you and another person and how close you actually are in that relationship. And so you can’t assume that too early even if you come in with really great academic credentials or experienced credentials to support that like, yeah, you do know what you’re doing.

(28:50):

They don’t know that until they see it.

Hannah Beaver (28:52):

Thanks so much for listening. For more from Kameko, I’ve dropped her LinkedIn into the show notes. For more from How to Make a Leader, be sure you subscribe so you never miss an episode. We’ll be back next month and every month with another insight from an L&D leader.

Your managers are leading people they’ve never met in person, on teams that include both humans and AI agents. Most leadership programs weren’t built for that.

Kameko Leung has built leadership development programs at Zillow, Michael Page, and now Pinterest, and she knows what it takes to develop leaders for that reality. She breaks down what distributed leadership requires: the operating systems, trust-building practices, and program design that make it work.

Things to listen for:
(01:47) Developing leadership in a distributed environment
(03:28) Adapting leadership programs for remote teams
(08:11) Building trust and collaboration in virtual teams
(10:59) Developing leadership instincts in remote environments
(13:50) Integrating AI into leadership training and development
(16:54) Using AI to improve feedback and manager training
(18:55) Coaching circles and peer-led leadership development
(21:15) The evolving role of managers in an AI-augmented world
(24:14) What strong AI leadership actually looks like
(25:40) How AI is changing learning and development roles
(27:47) Leadership advice for building trust in virtual teams

About Kameko Leung:

Kameko Leung manages Leadership Development programming for Pinterest and is the Founder of Bloom Mindset Consulting. With over 10 years of experience in learning and development, Kameko has experience providing the right developmental opportunities for leaders at each transition stage of their career journey – from aspiring manager to executive. With a special focus on leading and managing remotely, Kameko has worked with teams across tech, education, recruitment, engineering, sales, and non-profit to support leaders to evolve their practices and strategies for today’s work environment. Kameko is a CPTD credential holder and actively involved in the talent development community.

Connect with Kameko on LinkedIn and check out her dog treat company: The Seattle Barkery.