HR management platform
Subscribe to our Newsletter!
Thank you! You are subscribed to our blogs!
Oops! Something went wrong. Please try again.
Leading through transition - Gary A. Bolles [Interview]

Leading through transition - Gary A. Bolles [Interview]

Shruti Pawar
December 1, 2022

About Gary A. Bolles

Leading through transition - Gary A. Bolles [Interview]

Gary is the Chair for the Future of Work at Singularity University. As co-founder of, he helps job-hunters & career changers, from youth to 50+, with online and in-person programs. Gary is also an internationally-recognized expert on the future of work and the future of learning.

His focus is on the strategies for helping individuals, organizations, communities, and countries to thrive in the transition to a digital work economy. “What Color Is Your Parachute?”, is his best-selling book of all time.

Aishwarya Jain

Leading through transition - Gary A. Bolles [Interview]

We have the pleasure of welcoming Gary A Bolles today to our interview series. I’m Aishwarya Jain from the peopleHum team. Before we begin, just a quick intro of peopleHum -  peopleHum is an end-to-end, one-view, integrated human capital management automation platform, the winner of the 2019 global Codie Award for HCM that is specifically built for crafted employee experiences and the future of work with automation and AI technologies.

We run the peopleHum blog and video channel which receives upwards of 200,000 visitors a year and publish around 2 interviews with well-known names globally, every month.


Welcome, Gary. We’re thrilled to have you


Well, thank you for the invitation. 


So Gary I would like to start by asking your opinion on all inclusive term, which is the future of work. According to you, what would be the ideal future workplace like?


So, I think when we think about work in general and then where we work, people have got a range of different models. But essentially, what we've done in many of our economies in the shift from an industrial era to post-industrial sort of information age. 

We have kept this structure of lots of people working all in the same building in the same offices and then often having to commute to all get there. And that type of environment may have worked fine when we didn't have these digital distraction devices that we all walk around with, which allows us to communicate with half the people on the planet at any particular time. But we've talked about these digital technologies essentially allowing us to unbundle work, pull work apart. Then, along comes a virus and suddenly half the world's people are sheltering in place, having to use these digital tools. So I call this the great reset.

“Then, along comes a virus and suddenly half the world's people are sheltering in place, having to use these digital tools. So I call this the great reset.”

I wrote a piece in the Where I sort of breakdown what I see happening in terms of the unbundling of work. So many of the things that are changing in terms of work in the workplace were already underway. It's just they've accelerated, so they're coming faster.

One of them is that the workplace now is basically where you can do your work and where you could do your best work. And so I think of the workplace's context. So where do you do your best work? How does that mesh with the best work of your team, or the teams that you work with, how flexible and mobile is the work that you do?

If you wait tables in a restaurant, you can't do remote work and so at least not easily. And so there's a range of different jobs and work roles that are easier to have that much more flexible work situation, and we're gonna see a lot more of that happening. I think as in one of the things that would remain from this shift.


Right. That's very interesting, very interesting questions. And, you were talking about unbundling as well. So you do believe that work is becoming unbundled, fuelled by the combination of automation and globalization and driven by the rapid pace of change.

How do you think organizations should keep with the accelerating pace of change in the workplace today? 


So it's no question that it's the pace and the spread of change that I point to. It's not just that things were moving at an exponentially faster rate, but it's also the spread. It's a big leap in many cases. From the things that we were doing, the industry had become disrupted very quickly, business models suddenly become out of date, customers shift their behavior in a blindingly fast period of time, and so that's the speed and the leaps that change takes. 

And so I talk a lot about pace, that every individual at the most basic level, each of us as humans. There are sort of four transferable skills that we unfortunately call soft skills. But they are necessary. Problem solvers who are adaptive, creative and with empathy.

“There are sort of four transferable skills that we unfortunately call soft skills. But they are necessary. Problem solvers who are adaptive, creative and with empathy.”

Problem Solvers because that's really what work is. It’s about solving problems. And that's why we pay people. That's why people pay us. Adaptive, because all we can see is this exponential rate of change. And so we're gonna need to continually adapt. I always say there's no change management anymore. It's all about managing change. 

Creative because that's what keeps us at robots and software. That's a unique human scale where we have our time duplicating for a long period of time and then with Empathy and that's because, as humans that is also a superpower of ours, is the ability to fall in love with the problem of a customer or the world problem, and they continually try to use our abilities as problem solvers, who are adaptive and creative to solve those problems for others.


Absolutely. And I think that in all of this, There's a lot of entanglement with technology. 

So how do you believe workplace technology, specifically, artificial intelligence, automation in the future is going to change how we view our work and relationships?


Yeah, so I think it's an excellent question so the opportunity with technology is that it increases efficiency and productivity. And that's normally why we keep throwing everything from robots on assembly lines to now what’s called robotic process automation, automating repetitive human tasks. 

So at it's most basic, technology is about helping us to be able to do more. And, however, when we use technology, we throw it at solving problems. It’s always performing a set of tasks that humans used to do and the technology assumingly does it cheaper, faster, better especially when it’s repetitive and then that frees up workers. 100% freed up workers are called unemployed, and so I would say robots and software don't take jobs away. People give them away. It's a human's decision.

“100% freed up workers are called unemployed, and so I would say robots and software don't take jobs away. People give them away. It's a human's decision.”

If all those tasks add up to a job that goes away. So, we need to shift our thinking from this sort of automating repetitive human tasks, which are still things that have to be done but shifting our focus on trying to leverage technology and especially artificial intelligence, machine learning to augment humans. Help us to identify our superpowers, to improve our superpowers, to collaborate with others more effectively to solve new problems.

Use the example of the company Stitch Fix, which uses AI software and a clothing designer to keep sending a box of clothes every month to their customers. And between the support the AI software gives and the knowledge of the worker, they get better and better and more accurate predictions of the kinds of clothes that you're gonna want to receive. And so that's the superpowers that the designer gets because the software is designed to enhance that. 


Absolutely so it's basically leveraging technology in the right way to be an enabler, to support us, but also not to forget that, we are creative as human beings and we are problem solvers. We also have a lot of empathy, which is especially required in this situation right now because of the pandemic.

Do you think that the new normal would change once this is all over? Do you think the effects of remote working will sustain in the long run? 


So first, just a couple of thoughts about this. So probably some people will talk about remote work or distributed work. I normally talk about distributed work because remote sounds like more remote like we're just distant from each other, which is currently true. But if you think of it as instead of changing context, it's distributed. In some cases, you're together, you're in the same place, in other cases you're working remote. Or you might be a nomad, you might be traveling around as I do. 

But the basic premise is that the context of the environment in which you work will continually change, and one of the concepts that will be increasingly common is that you might not necessarily all be the same place at the same time. 

Well, in the past we had this model from an industrial area that I called 'Management by surveillance'. I have to see people in particular. I go watch you. Are you doing your work? But now it's trusted like, you have to trust me. Like, they’re home and you've got to trust. But you've also got to trust them to have the balance in their lives, that they got families, they've got pets, they've got sick relatives, they have things that they have to take care of. And all of us have those things. 

So now we've got a factor more of that into our work. I'm hopeful that we will actually have a better mentality about being able to loosen up management, make it from these controlled environments to a more guide on the side type.

“I'm hopeful that we will actually have a better mentality about being able to loosen up management, make it from these controlled environments to a more guide on the side type.”

We're going to understand that people have lives and we're going to be much more adaptive to allow them to deal with the things they have to in their lives. And teams will sort of step up to help them do that. I hope that we will find talent where it belongs immediately. That is, we will stop trying to pull people into all working in the same building, all going through the same horrible commute, all having to see each other in person every single moment of the day. 

We're gonna find talent where it's cheaper. I mean, it’s very expensive now, and so it's perfectly understandable. My hope is that that's gonna change. What is challenging is to ensure that organizations, that people will follow the practices to make sure that all those things work well and I'm happy to talk about what these practices need to be. But we do have to change our mindset and develop a new skill set. 


Absolutely. It starts with the mindset like you said, more and more people are bringing their homes into work and it's really a situation. It's a very unique situation where all of us are trying to grapple with that. And so what will be required would be a change of mindset and not just, you know we hear stories about the boss wanting to have the employees switch on the cameras for that 9-5 period, just to see if they're working on their desk. And that's just ridiculous, right? 

So, management by surveillance, that just does not make sense. As you said, empathy and trust is something that we really need to practice. 

And your book, right? “What color is your parachute?” Can you tell us more about that? It has a very interesting title to it. What was the concept? 


So just to be clear, So this is my father's book, I actually, when I was young, my father was a minister. He got laid off from a cathedral here in San Francisco and eventually got a job helping other ministers on college campuses. And then they started getting laid off. And so my father said, 'Well, I'm going to write a little pamphlet to try to help them', and it turned into a book known as 'What color is your parachute?’ When he wrote it in the early 1970's, updated it 42 times.

He passed away three years ago, but he left behind an amazing legacy and I, my wife, and another co-founder, we started the company that leverages his knowledge and puts it into the software. So what I've been able to do is, leverage that knowledge and with Singularity University, I focus on like the big macro strategies, like literally sitting down with heads of labor, heads of education in countries around the world. 

Talking about basically their economies. With my own company, we jump in with different communities and helping organizations to go through this process. But then what's really critical at the ground level for each of us as human beings is that every single person on the planet has a unique set of skills and experiences and goals and needs, and that unique mix contributes to that kind of work that they could do. 

Imagine when you were born, if the nurse came to your parents and they said okay, beautiful, healthy child, here's the user manual. Here's what the child is gonna be good at. Here's the kind of people the child would love to work around. Here are the kinds of work, experiences, and environments that they're gonna really be optimized for. 

When you buy one of these digital distraction machines, don't you get a user manual? It tells you what it's good for, what it's not. So how do we build user manuals? Well, it's trial and error. We don’t call it trial and success. It's trial and error.  

“So how do we build user manuals? Well, it's trial and error. We don’t call it trial and success. It's trial and error.”

You tell your kid, you touch the stove, it's hot, you don't touch it. Well, I have touched the stove a couple of times, I was a dumb kid. But eventually, you learn. 

And so then you want to stay up late at night. You're five years old, you can't say, you don’t want to. And then you're able to just come up with some arguments, and then you stay up. Magically, you've learned how to convince people, to persuade them. And so that's us. That trial and error machine. You're probably gonna be good at persuading for the rest of your life, you're gonna become a salesperson or business development person or a politician, but basically we have to build a user manual for us.

Well, that's what my father's work is all designed for. Parachute is about first helping people to do the What, the self-inventory. Then the Where, what's the different places you could use those skills and interests and goals. And then, finally, the How, like the mechanics of finding or creating that work. Each of us every time it goes, through a pivot, we go through those three steps. We just don't know we do.  We do some kind of looking at ourselves, Maybe some kind of planning. And some kind of execution.

The reason my father kept updating the book is because the world changes. What works, changes. You know, we don't use Yellow Pages and mail resumes much anymore. Everything's become digitized. So continually adapting the strategies that work best has been really the role of Parachute.


Yes, that is so important, and that's very interesting. You know, the way you'll shift and you adapt in a fluid, and it's really about, understanding what value set you bring to the table. As you said, a lot of trial and errors, experimentation is what it really is about as we are all humans. 

And that kind of brings me to the question that when we were trying to bring our best selves to workplaces, right. Are there some kind of best practices that we must follow in the workplaces to have more purposeful, let's say a job or a career as such?


So let me just tell you sort of the four layers that we see people go through in their careers. Typically, this is pretty common and then you can decide for any of your viewers, where you stop, like where you want to stop. 

So when you first start working, what's the one thing you want to do is you want to get paid like I just want to make enough money. Then when you realize after a while and when I was dumb, you know, I just did a whole bunch of literally dozens of jobs and never was all that interested in college, including falling in the family business and being trained as a career counselor.

But first I want to just get paid and then what you realize is, if you're good at this, you get paid better. All right, so now you gotta get paid but then you want to also do things you're good at. Now some people stop there. It's just getting paid. Well, you're good at it. You feed your family, put a roof over their head, okay? And I call those the old rules of work. 

But my father found is if you also do the work that you love, if you're solving the problems that fascinate you, if you're using the skills you feel you're most optimized for, if you're working with the kinds of people that help you do your best work, if you're working in the workplace, that helps you do your best work, then you not only can get paid better, but you actually have tremendous fulfillment. Now some people stop there.

But it's also possible to then think about and what does the world need? So this is actually called Ikigai. And it's a practice in Japan, and this is called blue zones, where Dan, you know, the author, interviewed people in Okinawa, and they followed this practice, and...

“They actually believe that a life is not well lived unless you make money, you do it well, you do what you love and you do with the world needs.”

And so young people nowadays come at it in a totally different manner. The old rules of work- you work your way up the stack, and maybe by the time you retired, you gave money away to help the world, right? Maybe you volunteered a little bit. 

They flipped the stack. They first want to know How can I change the world? Okay if I'm changing the world and I'm gonna love doing that, if I love doing it, I'm gonna get better and better. And if I get better and better and I'm gonna get paid better and so that's my answer to you is people get to choose where they want to stop on the stack. 

But that's how you can leverage purpose, you can figure out if you feel like it has meaning for you? It is just making enough money to feed your family. That's totally fine. The problem is, in a world of exponential change, it probably isn't enough. 

If you're just focusing and working in the factory or working in the mines and the factories and the mines shut down, you've got to have this mentality of what are you good at? What do you really want to do? What skills do you love using and use that as your North star.


Wow, that is so absolutely interesting. The way you talk about those stages. I really do think that millennials and the newer generations are really thinking about a purpose in their life much more than psychological safety Or just having to earn some bread, right? It's just much more than that. 

When you think about the growing ranks of millennials and there is also the concept of the gig economy that's on the rise. How do you think this trend is relevant with respect to the future of work? 


So think of the gig or any work platforms. Just the language is often called two side work markets, right? So there's a demand as your customer and there's supply, that's us. Messy, expensive humans. And then there's the software that connects us, and that's everything for Uber to work markets like Top Coder and so on. 

And so I think of it, is basically unbundled work. In the past, you had one person, one job. Old rules of work, new rules of work.  Maybe they're still jobs. But then there's all these other work contexts, and so I call that a portfolio of work, right?

You might be having a day job, but then you're also driving for Uber at night and you're working on a start-up with your friends. It's a portfolio. It's a constantly shifting landscape of work. Now, unfortunately, we haven't trained people on how to do that. We don't even train people on how to do jobs. 

We were not doing a good job training in how to manage a portfolio of work. So I think of it as unbundled work like used to have all the pieces of a job, place and so you know, we pulled all those pieces apart.

“The good news with gig work is you get variety and flexibility. The bad news is you get unpredictable work that's precarious.”

So immediately we hit this great reset and no Uber or Lyft Driver has any other work, and Uber and Lyft are not responsible for that. 

Your employer might have been responsible for at least ensure you've got unemployment benefits. But at Uber or Lyft, that's not our problem. And so what I guarantee will happen is there's is gonna be continually more unbundled work. What we must do is rebalance this table because otherwise what happens is the worker kind of loses. The platform will always win, it gets its money. The demand, that's the hirer, will always get cheap labor and hopefully, good labor. But the worker is the one that's at the disadvantage.

The table’s tilted, so what we need to do with the gig work is sort of tilt the table back. You need to give micro benefits so that you can actually save for retirement so you can actually have health care. You need to have ways that you can actually bundle workers together, so if they can get paid better, they can get better shifts better.

And I also remember that unfortunately there's a whole bunch of work in the world that can't really be easily gigafide and still have workers have meaningful work. There's a lot of people in the world, especially if you've got kids and they get out of school a certain time. You can't have variable shifts. You can't just take any shift. You must have a predictable time. You could be home to meet the kids. 

So back to what we're talking about originally is, I hope we're gonna come out of this year with an understanding that each of us as humans. We have lives. We have families. We have things that we need to do. And we need to continually have this adaptive landscape of work. We need to support each other so that we can ensure that, sure you can have the time off that you need and you're not going to lose out. 

You're still gonna have sick pay, you're still gonna be able to have unemployment benefits, you're still gonna be able to save for retirement. All those things will still happen even in an unbundled world.


Absolutely. That is so important to understand how to be more inclusive with respect to all kinds of gig workers. To understand that there to have families and what's kind of the definition of fluid or digital economy as such. And these questions would be really relevant at this point in time and in the future. 

And at this point that there are just so many people that are going through layoffs and furloughing right and they would have to look at a career change, they would have to look at a new job. Do you have any kind of advice for such people? 


Yeah, absolutely. So first off, my heart goes out to anybody that has been deeply affected by this great reset. I think what we've found as humans is that there are so many things that connect us. I mean literally when half the world's population is being asked to stay homeless. 

In no time in human history have we ever had every single person going through such a similar set of experiences. Billions of people going through such similar experiences and my heart goes out to anybody that's been deeply affected by this, because for each of us as individuals, it's a massive challenge and as societies, it's huge.

So first off, I'd say you must focus on yourself. You must take care of yourself. It's a great time for introspection to do that self-inventory, about your own skills, to be able to think about the kinds of work that you could do, to be able to try to build out your network, to try to continually contact people and communicate. 

What's gonna happen is as each of our economies start turning the lights back on, it's gonna be, if you have played musical chairs before. The simple game is that the music's playing and we're all walking around and they're fewer chairs than there are people and the music stops and suddenly we're all jumping on the chairs. We're gonna be doing that in each of our economies. 

Now, some of the shares are gonna be really easy to hop into. Your old employer is gonna call you and say, I need you back. Hopefully, we'll pay you the same or better. They're not going to say, you can come back, but I'm gonna pay you half that. That wouldn't be good for a lot of people. But there's gonna be places where there are lots of chairs and no people, there's a need but they don't have the skill set of people to hire for.

There are other places where there's going to be lots of people but no chairs, especially in rural areas where the work will have changed. In the United States, what we did just to give an example, how the game musical chairs were played is we changed the rules for most of the chairs. 97% of the net new jobs that were created in the United States after the great recession, demanded a high school diploma. It's crazy.

So the result is you've got to be able to be flexible as a worker. You've got to know your own skills and try to find the places that you could leverage those skills to be able to do your best work. But hirers, employers also need to be as inclusive as possible. They need to work even harder to keep paying people even when it's a challenge for them because you're gonna find it much harder when the music stops. 

You're gonna find it much, much harder to actually find the people that you wanted to find, which was already challenged beforehand. And so it's really, really important to be thinking about how we're working better together as we recover from the great reset.


Absolutely. I loved the analogy of the musical chairs to understand what we're going through, you know, it makes so much sense, and it just helps us understand things in a lucid way, and that's also great advice for people who are really struggling at this point in time. 

And I would just like to wrap this interview up, asking you for any other important soundbites that you'd like to leave us with?


So you know, why waste a good crisis?

“Every pivot point in history is an opportunity.”

So we go through these phases as humans. And so there's a lot of grieving for where we may have lost and certainly for the challenges that so many people are going through and my heart goes out to everybody who is dealing with these challenges. And I hope that you're both safe and well and that you have the support around you to help you to be able to get through these challenging times. 

So the opportunity for individuals is to define your North star, I’m sure your listeners are in the southern hemisphere in Southern Cross. And once you find that footing, help others as well because they were gonna be communities that will be devastated from this for a long time. 

If your organizational leader you have the opportunity to think about how you change the way your company works. This needs to be a big shift. We need to completely think differently about how we're helping humans to match up for the problems that we need to solve. We need to be inclusive. We need to leverage skills that we wouldn't have thought we could leverage before. Hire people that we think are outside of the normal profile but who have tremendous ability to solve problems that we would never have even thought of. 

You've got to develop talented people, got train them.

“There's one mantra that I say repeatedly, it's 'no human left behind'. How can we ensure that we bring many people along to be able to thrive in the next economy’s reset because we are going to  build different kinds of economies.”


Well, that's a beautiful mantra to have there, make so much sense and as you said, It's just really time for introspection and to understand and re-skill, upscale at this point in time to really make us as much more richer when we come out of this because it would be a learning experience and that could be another reset like this in the future. 

So it would be good if you're prepared right now for it. So thank you for those wonderful words. And I had a great conversation with you, Gary. Thank you so much. It was really a pleasure talking to you. 


And so as well. Best of luck. Stay safe and be well.


You too, stay safe, take care and have a healthy time ahead of you.

See our award-winning HR Software in action
Book a demo
Schedule a demo
Is accurate payroll processing a challenge? Find out how peopleHum can assist you!
Book a demo
Book a demo
See our award-winning HR Software in action
Schedule a demo

See our award-winning HR Software in action

Schedule a demo
Blogs related to "
Leading through transition - Gary A. Bolles [Interview]

Schedule a Demo !

Get a personalized demo with our experts to get you started
This is some text inside of a div block.
This is some text inside of a div block.
This is some text inside of a div block.
This is some text
This is some text inside of a div block.
Thank you for scheduling a demo with us! Please check your email inbox for further details.
Explore payroll
Oops! Something went wrong while submitting the form.
Contact Us!
Get a personalized demo with our experts to get you started
This is some text inside of a div block.
This is some text inside of a div block.
This is some text inside of a div block.
This is some text inside of a div block.
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.