Get Reworked Podcast Episode 16 Guest Shelley Osborne

Get Reworked Podcast: Why Upskilling Is an Imperative for Every Business

June 15, 2021 Learning and Development
Mike Prokopeak
By Mike Prokopeak, Siobhan Fagan

Get Reworked Podcast Guest Shelley Osborne
There is no status quo anymore when it comes to skills. New technologies, new realities and new challenges are arriving at a rapid fire pace, leaving many previously skilled and experienced people on the outside looking in. That's why many organizations are embracing the need to reskill and upskill their workforce. But what exactly does that mean?

In this episode of Get Reworked, Shelley Osborne, corporate learning executive and author of "The Upskilling Imperative," explains and tells us why the ability to learn is the essential skill every organization and every individual needs to succeed. Interestingly, it's not about a specific skill. Rather, it's about creating an environment where learning can happen. 

Listen: Get Reworked Podcast Full Episode List

"When we do it well, and when we create these incredible learning cultures, and set people up to be growing and developing and upskilling, we make the best organizations, the most innovative, creative, interesting, amazing places to work," Shelley said.

Highlights of the conversation include:

  • How upskilling is different from reskilling.
  • Why a learning mindset is the key to the future of work.
  • The core tenets of a successful learning culture.
  • How to avoid letting the mistakes of the past define how companies deliver learning in the future.

Plus, co-hosts Siobhan Fagan and Mike Prokopeak share what teachers influenced them the most and come up with a new business idea. Listen in for more.

Have a suggestion, comment or topic for a future episode? Drop us a line at [email protected].

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Show Notes

Episode Transcript

Note: This transcript has been edited for space and clarity.

Mike Prokopeak: Hello and welcome to Get Reworked, your guide to the revolution of work. My name is Mike Prokopeak and I'm editor in chief at

Siobhan Fagan: And I'm Siobhan Fagan, managing editor for Reworked. At, we're dedicated to covering the people, the culture, the technology and the infrastructure that makes up our quickly evolving workplaces.

Mike: Get Reworked is our podcast, brought to you by Simpler Media Group, where you'll hear from industry pioneers leading the way into the future of work, reshaping not just how we work, but also why. We're excited to bring you conversations about best practices, workplace trends and key technologies that support the modern distributed workforce.

Hello, Siobhan.

Siobhan: Hi, Mike.

Mike: How are you today?

Siobhan: I'm doing all right. You know what I have been doing lately, though, Mike.

Mike: I'd like to know.

Siobhan: I've been cleaning house, and I recently came across my old yearbooks.

Mike: Ooh, so what did you find that was interesting in yours?

Siobhan: Well, a lot of really awkward like Too Cool For School people writing stuff in your yearbook, and how incredibly awkward we were as teenagers. But I also I saw a teacher who I hadn't thought of in a while, and I just reminded myself of what an amazing teacher he was and how he probably should have been teaching in college rather than high school because his talents were wasted on us.

Mike: What was it about him that kind of was different than your average teacher?

Siobhan: He was my history teacher. Mr. O'Connor, if you're out there, I'm sorry, that we would spray perfume on before going into your class knowing that you were allergic as a joke. That was really mean.

He was a high school teacher, he was a high school professor, we were gonna play games. But he was so passionate about history. And he just really shared that with us. And I caught the history bug from him. I remember him teaching us about the Crusades in a way that a I don't think I would have learned about them in the first place. But B in a way that taught me all the different sides that you can view history from. Did you have a similar experience with any teachers?

Mike: I had two, I guess, one in high school, one in college, and there are both what was my high school English teacher, and one of my English professors in college and big surprise, I was an English major. So you know, probably pretty natural that, that I would gravitate towards them. But the thing that stood out from my high school teacher, Mr. Woodell, and my professor in college, he was actually my advisor, Dr. Klein, Dr. Mary Ann Klein, was they both didn't put up with mediocre effort, which I was specializing in.

I mean, it was it was done in a very encouraging way. It's not it was just like, when you did good work, they recognized it and said, You know, this just stands above everything that you've done before and it shows the potential. And both of them noticed that, which when you're teaching a lot of kids, especially in high school, that's tough to do, and encouraged it and actually demanded it, because they knew that I was going to try to skate by with a modicum there. That's what really, I think, I appreciate it about them.

Siobhan: You're reminding me of so many different professors that I had, who had such a dramatic impact on how I thought and how I still think to this day.

Mike: A good teacher is truly transformative. I think that's really been the experience that we're both talking about, that there have been these people who have opened up our minds to different ways of thinking about things. And I think that's a great lead into our guest today who herself was a teacher, both in high school and in corporate environments. So I'm really eager to get talking to Shelley Osborne, who is the author of The Upskilling Imperative: 5 Ways to Make Learning Core to the Way We Work.

We're going to talk to her about that book, in particular about what upskilling means and how do we apply that in our organizations as we're in the midst of this time of dramatic change. I think Shelley not only being a fun person to talk to and a person with a depth of education experience going back to high school. She also has experience in corporate education. She was up until April of this year, the vice president of learning at Udemy, where she led the company's learning strategy and its upskilling efforts for all of their global employees. So she's got a pretty good set of experiences to talk through this topic. She's in the midst of what's next. And it's all in stealth mode, which I'm really curious to find out what's coming next for Shelley and she's promised us that later this summer, she's going to tell us but we don't know yet. So I'm interested in finding out. So are you ready, Siobhan?

Siobhan: I am so ready.

Mike: All right. Let's Get Reworked.

Welcome to the podcast, Shelley.

Shelley Osborne: Thank you so much for having me. I'm just so excited to be here.

Mike: All right, we've got a big topic for today. The topic is upskilling, and we've got you as a resident expert on this topic, because you wrote the book on the upskilling imperative. So start us off here, give us an idea what is, from your point of view, the upskilling imperative.

Shelley: You know, I was really motivated to write the book, because we've just been inundated by all this change, and this need to develop our skills. It's coming at us faster and faster. And I started to notice that there was this expectation from employees and just people in general, that they'd hit an endpoint to their learning, that there'd be a point where they were done, or they could sort of throw up their hands and say, Okay, that's it, I figured it all out. And that's just not true. It's never been true. And it's less true now, as we see just so many changes happening in the way we work, in technology, and just the shifting landscape of even this past year and a half of a pandemic.

So when we kind of pile all that together, I really wanted to put together a bit of a roadmap and a perspective on how we develop this perspective in employees and in organizations that we're always learning, and how do we create the conditions for that to happen? So the imperative is that we all need to upskill, organizations need to upskill, and how do we do that? How do we get our heads around that? How do we set up that culture?

Mike: Alright, so I think all of those things we want to dive into in this conversation. But I think it's also important if we get some of our vocabulary history upfront, you being a former teacher, I know that you appreciate that as well.

Shelley: I do.

Mike: So, you know, upskilling has become a lot more, a bigger part of the business lexicon over the last year and a half, two years if you've been in learning and development longer than that. But also this term reskilling gets thrown in there quite a bit. And I'm wondering if you see upskilling and reskilling as different things, and if so, how are they different?

Shelley: I do. I think I see reskilling as a kind of upskilling. Upskilling, to me is this broad bucket that we can kind of lay upon everything. And this idea that we're in this continuous growth and, and always developing. Typically, most people refer to reskilling as this perspective that somebody is going to have this idea, I'm going to go figure out something new, I'm going to learn a whole new set of skills, because whatever I was doing, or whatever I had studied or learned before, is no longer applicable, and I'm gonna go into something completely different. So to me, that's a kind of upskilling.

But upskilling can be broader and can be this development of the skills you already have an up leveling a collection of new things to add to your toolbox. And I think they're they're both valuable, they're both really, really good things for us to be doing.

Mike: So from your point of view is really skilling more about your particular job that you may be in that, you know, maybe your your job is being automated or something is happening in your industry, that sort of pushing it away or into a different career is, is that where reskilling fits a little bit more accurately?

Shelley: I think so I think it's more of that perspective of, okay, I need a whole new set of things to do X. Now, granted, it could be outside of a job, it could just be something you really care about. But traditionally, and typically, when we're using this phrase, it's usually in that frame of a new job, a new discipline for your work.

Siobhan: Is this a new way of looking at learning in businesses? I mean, traditionally, they're looking at sort of compliance training or technological training on a specific software. Does this require a new approach for businesses in your opinion?

Shelley: Oh, absolutely. I have a pretty strong belief that learning is the future of work. And there are organizations out there who've accepted this and who are really into creating incredible learning cultures and see their path forward as having people learn and develop new skills. But to your point, there's a ton of organizations who have kind of put learning in the corner, or they have thought about it in these really historical kind of yucky ways where it's just compliance or even the word training.

I'm a little allergic to that word, because it has some negative connotations where I'm going to train someone and I'm going to tell them what to do. Those mentalities are really something we have to ditch. And we have to get more around this idea of continuous growth and development, and really rooting people's careers in learning. That's where the engagement comes from. That's where the innovation comes from.

Mike: I appreciate the fact that you use the very technical term of yucky. I think that really does a nice job of describing kind of the state of where things are at.

Shelley: Thank you. I like to throw out the big words every now and then.

Mike: Just to kind of home in again on this upskilling idea and how it's different from what you talked about in the idea of traditional training. What are the specific skills, for lack of a better term? Maybe its capabilities, maybe that's a better term? What are the specific capabilities that are in need of upskilling? When we're talking about upskilling, in saying it's different from tactical skills or are different from traditional training. What are the things that need to be upskilled in order for us to continue to evolve as people?

Shelley: I have a bit of a non answer for you that you'll probably hate me for. But I think the most important thing that literally every single human on the planet needs is the ability to learn and the willingness to do it. And that's foundational, and absolutely table stakes to even have an upskiling mindset. And I'm okay, actually referring to it as skills, as capabilities, as competencies. All of those are relevant. And all of those are important.

What's really, really important for us all to understand is that these skills are changing pretty rapidly. The half life of skills right now is less than five years, we are seeing new technologies, new competencies thrown at us that we have to be able to grab and develop and be open to that. So without that perspective, first of being aware that you're a learner, and that your job is actually to learn, you're not going to get anywhere. So that's the first thing everybody really, really needs. And I get asked a lot with my background and my career, okay, Shelley, what are the skills I need right now? And what are the five things that I need to learn today? And I really resist answering that question, because I think there's a couple of problems.

Number one, there's a lot of options out there. Number two, it's pretty unique to you and your goals and what you're actually looking to accomplish with your career in your life. And then the third piece is just how really quick the expiration date is on all that. Now, you might think, okay, well, then, what's the point? Why do I learn anything? Well, you're building a collection of skills, and they develop upon each other. So I think that my non answer is really to learn, you need to have the skill to learn. That's the most important thing. And if you have that, you're unstoppable.

Siobhan: So I've got a confession. Now, I took your class in preparation for this podcast. So I guess I was doing a little upskilling on my own side.

Mike: She likes to make me look bad, Shelley.

Siobhan: I always go for the extra credit.

Shelley: You know, a gold star all the way. Mike, we'll talk later.

Mike: Stay after class. I've been there.

Siobhan: One of the things that you covered in depth in the course, was actually the creation of this learning culture. And there are specific skills, I'm actually kind of pushing back on your non answer to the last one, there are specific skills that you think are needed to create that culture. So I want to touch on one of them. And you can definitely go into the others, but I know that this one is particularly important to you. And that's the role of feedback in creating this culture. So can you talk a little bit about that?

Shelley: Oh, my gosh, absolutely. And thank you for bringing that up. I first want to say, I think the role of an L&D leader, a learning leader and HR leaders and CEOs is to create this culture where learning can happen. That's so important. And not necessarily where people start. They think like, okay, I'll create this company, I'll worry about this product, I'll think about who we're selling to in our market. And then later, way too late down the road, they start thinking about learning and development. And I think it has to be right up at the front.

So I think creating that learning culture is essential to have an organization that can thrive through all these changes and develop and grow and, and create amazing careers for folks. And feedback is my absolute favorite thing, you're 100% right. I'm a little obsessed with feedback. And I think this comes from my teaching days really feedback is the root the core, almost the definition of learning, in many ways, because without those inputs, and without that information on our opportunities, on where we've excelled on places we could explore next, we're lost.

And I think it's an essential thing for organizations to, to really double down on. How do you create the opportunities for people to give and receive feedback? How do you make it so that every single person in your organization is aware that feedback is something so essential to their career, and that is something they should crave and seek out? And then how do you also make sure that it's going all directions, so it shouldn't just be this classic perspective we have on it, where managers sort of dump feedback down. You want to create this messy grid of feet back going all sorts of directions. And that's where we actually start to uncover the gold, the opportunities and the nuggets.

Siobhan: I lied, I said that you could touch on the others if you wanted to. But I'm actually going to ask you right out: Can you share the other skills that businesses need? Are these other foundational elements of creating this culture?

Shelley: I think it's really important to think about this in a couple of different ways, feedback is one of the first things that I'm focused on developing in organizations. You also need that learning agility. So I talk a lot about that idea that you're a learner. I often tell people to stop describing themselves as their career, their job, like don't tell me you're an engineer, tell me you're a learner and that you're learning whatever programming language, right? So that learning agility is really, really, really critical.

I think it's also super important to put learning right into the flow of work. We talk a lot about that in the L&D space. And we haven't necessarily achieved it. Well, we still book people for a two-day workshop three weeks from now where they might learn something they could possibly have needed yesterday.

I'm also really, really passionate about how we market and how we talk about learning and development to our organizations. We have to think about how noisy it is for employees out there, right? Like, they are absolutely inundated, inundated, with all of these different messages, with communication, with all these demands on their time, and learning and development has to be able to cut through that noise. We have to engage with them and create learning experiences that are attractive and appealing to them. And I think that that one is actually really overlooked and something that not every L&D leader is really focused on. They're sort of creating these great learning experiences but they're not necessarily actually trying to get them out there.

And then I think we also need to be able to make that business case and talk about the ROI of learning really clearly. That's essential as well. And then as a last sort of wrapper on all this, and I think it threads through my entire book, this idea about change. We need to be open to change, know that we need to change and have a perspective for it. So these are the things that organizations need to be able to really build upon. And these are those core pieces to help create a learning culture.

Mike: So that actually brings up I think, the next phase of this conversation, Shelley, when we want to talk about how the last year has changed how employees learn. But I want to start with this question for you, which is, how does upskilling play a role in digital transformation? Because that's kind of where we're at. We're at this point where companies have been forced to adapt to changes and transformation pretty dramatically over this last year. And to the point, I think, where people are exhausted with it, and now they're kind of looking for a little bit of pullback or a little bit of more sanity to it.

Shelley: Yep.

Mike: How does upskilling play a role in this transformation of what's happening next?

Shelley: You know, it's kind of amazing to think what we've all been through, right? We've all talked about that. It's been just an astonishing experience, and year and a half. And I think we were already pretty overwhelmed with the digital transformation we were facing previous to a pandemic hitting us, right. And I think we knew we needed to face it, we knew we needed to get employees and organizations ready, but we weren't sort of just thrown in the deep end of the pool.

And that's what happened with this pandemic. Suddenly, we had employees around the world who had varying levels of skills with the technologies they were interacting with. They couldn't walk down the hall to the IT department to get support. We were suddenly having to work in entirely different ways, and the classic approaches we had to learning and development around both digital skills, and those more technical skills and soft skills was thrown out the window. We couldn't do any of that the way we used to. And I think what has been pretty incredible is the creativity and the willingness employees have shown to sort of open themselves to new experiences and self-discover new ways of working.

What I think is really, really important is that organizations can't sort of just leave this to happen. When I think about my old learning and development team, when we were first faced with the pandemic, we heard on a Friday that we were going to be going work from home fully. And on a Sunday, we threw together a really quick course, with a ton of amazing tips and tricks on how to work from home effectively. And we had that available to employees on the Monday that they started working from home officially.

That's the kind of mindset that L&D and companies need to have. It's this get away from this perfection, get away from this really sophisticated nine month building of a training program and just give people what they need. That's the sort of next phase we have to think about with digital transformation because we've been slowed down and held back by these perfection tendencies we we tend to hold in L&D, when people just need help and they need support, and they need it fast. And I'm extremely proud of my team and how we we pulled that together and supported the company through a really rough time.

And that was so well-received and appreciated by the employees. It didn't need to be fancy. It didn't need to be beautiful. It just needed to work.

Siobhan: Shelley, I think that sounds like your teaching background coming through. That you had to sort of put something together really fast, maybe with limited resources, and maybe L&D people need to go into like a high school teacher boot camp or something.

Shelley: Oh, my goodness, you are literally saying something I've thought a million times. I actually don't think it's just L&D people. I want to put everyone, anyone ever put them into a high school classroom, and then have the projector stop working or power goes out, or, you know, there's some sort of like explosion of like somebody's soda in the back of the room and you got to keep teaching. There is no better training for life than being a high school teacher, I don't think.

Mike: Yeah, and how to overcome a hostile audience. I mean, it's perfect training for that as well.

Shelley: You know, what I'd say that's true, I have to say a lot of the students I taught were pretty incredible. But you know, they they teach you how to how to have a thick skin too.

Mike: So as I'm thinking about this sort of transformation of the learning and development function that you're talking about, you're able to sort of happen in that you're saying other folks need to make happen as well. I'm wondering what needs to happen not so much from the learning and development function? Because I think the desire is there, even in those organizations that may be very engaged in traditional ways of teaching and training. I think the desire is there, perhaps maybe the belief on the part of their business partners might not be there that they're the people who can do this.

Shelley: Yeah.

Mike: How do you recommend that L&D address that gap between what they believe they're capable of versus the what others may believe they're capable of based on history.

Shelley: I think this is one of the most important competencies an L&D leader can have. And it's really this relationship building and stakeholder management. And I do think that I spend the majority of my time in a company actually working on that, because that's the thing that's going to make these initiatives successful. As long as I know, my leaders, my peers, the stakeholders involved, if I've built those really trusting relationships, and I'm delivering on their needs, that's critical. And it feels like a bit of a waste of time to keep having those one-on-ones or to keep building those relationships and having chats over time. But that's what makes it possible.

I also tend to find the person who believes in learning the least, and who's the most difficult, and the most critical, and I make it my life's mission, to have that person be my best friend, and just really to understand them and, and talk to them about my goals and, and really get their feedback and engage them in the process, because that really makes it their work to it makes it their initiative in their project as well and there's invested in it success. And I think that's been one of my best tools in my tool belt.

Siobhan: You mentioned earlier the importance of being able to make that business case for the learning, which I assume would come into, you know, these relationships at some point. I'm curious when you talk about that A), what kind of advice you would have, and B), how you can actually show the ROI of learning soft skills that aren't necessarily quantifiable?

Shelley: That's one of the tougher ones we always try to solve. The first thing I would say is its audience, audience, audience. You really need to understand who you're talking to when you're talking about ROI because there's a lot of different places you can take that conversation. Are you talking to a CFO? Well, you're probably best served to be talking dollars and cents there. Are you talking to an engineering leader? What do they care about? What are the problems they're facing, and help tell that story for them, and connect the dots on how learning is going to have impact there.

And one thing that I think is really, really important is to have that ability to talk not just about the hard metrics that you can prove, you know, you can talk about how you got to an engineering team on a new programming language and they're really seeing and shipping products faster. Okay, great, that's really hard metrics. But you also want to be able to speak really confidently to the correlation versus just the causation, and there is an element of this that you have to help them understand and help them accept.

We know that it's difficult to prove everything. There's a lot of different factors when we're studying the impact of any learning initiative. So if you can kind of speak to both of those sides, I think it helps your impact and your initiative come to life. But again, probably the most critical skill here is think about who it is, think about how they view the world, what they care about, and try and help tell that story. Its audience, audience, audience.

Mike: Has the last year been helpful in that regard? Because, you know, it became such a demand, as you mentioned, when you kind of within a weekend turned around a new course for people to understand how they can make the most of working at home. There's been a lot of demand for this sort of content, this sort of learning. We need it right now in order to adapt. Do you think that sort of shifted a little bit how people approach or how people think about learning and development organizations? Are we liable to kind of snap back a little bit to the traditional way people have thought about it, and, you know, focus on the ROI again?

Shelley: You know, I do think one of the upsides of this experience has been a shift in how we look at both HR teams and L&D teams. I don't think I've ever seen more L&D jobs posted on job boards than I'm seeing right now. And if I think back to other big dips in the economy, those are typically jobs you see wiped away and considered to be less necessary. Whereas this time, it felt very opposite. It felt like, oh, okay, no, we need these folks, these folks are going to help us through this transition, they're going to help us with our return to work plans, they're going to help us with really rethinking how we onboard all of these kinds of pieces. So I do believe that there's been a change. You know, the water's a little bit different now, and it's a little bit more understanding of the value and impact that this function can have.

And my hope and dream is that we can continue to harness that and show the kinds of impact that learning can have on a company. Because when we do it well, and when we create these incredible learning cultures, and set people up to be growing and developing and upskilling, we make the best organizations, the most innovative, creative, interesting, amazing places to work.

Mike: So thinking about titles, I think companies tend to get a little too cutesy or a little too creative sometimes sometimes with titles. But the question I have is, is learning the wrong terminology for what you're describing? Do we need a different name for what people who are doing upskilling, who are focused on the long term impact of learning are doing in organizations? And what would that be?

Shelley: Gosh, I've actually thought about this a lot. And I have to tell you the truth, I don't have a perfect answer for this. I go back and forth. I think for me, I really have an affection for the word learning because I think that it captures it all. It captures our growth in our careers. It's career development, it's picking up skills and competencies. It's understanding a work environment, it's transformation, it's everything. So I do actually really like that word, but I would be lying if I didn't say, there's been times over the years where I've tried to imagine a new way to define this paradigm. And I always fall back on the word learning. It just feels the most holistic to me.

Mike: Yeah, the one term I've seen in a couple job postings is growth, which I feel like it is a nice way to frame it. If you say the job is growth and learning. Yeah, it's just growth. I think that's a little too vague and people might think of that as like a sales function or marketing.

Shelley: Yeah.

Mike: Alright, so we talked about upskilling. We talked a little bit about how the pandemic has shifted how employees learn and how learning functions are operating. I want to talk a little bit more about this future and maybe a little bit more detail about what's coming and what do you see the future holding for companies as they're looking to transform and the learning and upskilling that needs to go along with that. But one thing I think to start off with is the fact that we have fatigue in organizations. And in fact, we may have learning fatigue as employees have been at home and have been forced to stare at screens or engaging in learning via digital avenues. What can be done to ward off a little bit of that learning fatigue?

Shelley: Gosh, I mean, I felt that too, and that's something that I think a lot of L&D teams are facing right now. This sort of, we don't want to overwhelm people, how do we think about what people actually need right now? And something that I use with the teams I lead is this framing of what's the PONT? What's the Point Of Need and Time? And I think that that's a really helpful starting point for L&D teams to think about, okay, like, it's great to have a beautiful 2020 strategy like I did that had all sorts of big plans and dreams that I basically erased, and we focused on supporting people through transitioning to work from home to emotional well being to change agility, all those kinds of things are really, really critical.

When I think about how we we sort of face the future, I think the PONT is something that I'd like people to think a little harder about, and to think about how we preserve and protect people's time. Again, we've been really married and stuck in these perspectives of, we need these huge long workshops, and we need super long courses. And we need these experiences that don't necessarily suit the environments we're all working in. And don't necessarily get us the skill we need at the moment we need it. It's that putting learning in the flow of work.

And I think if we can start to focus a little bit more on thinking about those discrete skills, how we serve people in the moment, that's helpful. How do we create the conditions and opportunities where they have access to the learning they need all the time, not just when I scheduled it a month from now, that's helpful. And how do we make sure that everything we give them is incredibly impactful, there's none of this extra, there's none of this just superfluous content or experiences that they don't really need. I think we have to be ruthless in our prioritization and thinking about how we serve learners.

Siobhan: I think that part of what's feeding into the exhaustion is just the constant competition for our time. We spoke about it a little bit earlier. And I think that what you talk about, you know, delivering the learning in the moment absolutely makes sense. But, how do you create those permissions for people to feel like, I feel guilty sometimes when I'm reading during work, you know, like, I'm like, that's not, I don't have time for that, even though I'm an editor, but how do you make this clear, that that is not only allowed but it's encouraged?

Shelley: Well, one of the other core tenets of building a culture of learning that I haven't talked about yet is signaling the value of learning to your company. And this is so so, so important. And there's a couple of ways you can do that.

I talked earlier about this idea that I wish people referred to themselves as a learner instead of their their job title. Well, that mindset, and that sort of perspective has to come from the organization, you have to be hearing from all levels of leadership, that it's okay to learn and that it's actually expected that you'll be learning on the job.

And there's lots of ways to do that, you know, you get your CEO to stand up and talk about the course they just took or the book they just read or this incredible article that informed something they were doing, that signals the value of learning to every single person. And when you have somebody who's in a position of power and authority like that, who makes it safe and makes it okay, that's critical.

I think also, you really do want to create all those kinds of conditions at all levels. So you want your managers to be talking about career development, but you want them to be asking what the learning is going to be as an output of career development. A lot of career development conversations are about what's your next job title? Or what, what's your next project? I reject that, I'd much rather people be talking about, so what are we going to learn next? Oh, that project will help you learn that. That's the way to connect these things.

So when we start to build that culture, and admittedly, it takes time, you have to build in these foundations of feedback and learning agility and an openness to change and, and then you've got to market these experiences really creatively, and then you have to signal the value and make it safe, that all has to happen.

But back to that marketing point, one thing I would add, is, it's really important to also cut through that noise with creativity, and to really make sure that you're making something seem engaging and exciting. And it's not always everyone's favorite thing to do, a lot of L&D folks don't consider themselves marketers. But I've had the most success really learning from the incredible marketing leaders that I've been able to work alongside and copying some of the same techniques they use to sell our product to sell the L&D that my team is putting out there.

Siobhan: So I love that example that you just shared of people sharing the book that they read, or you know, I learned this from an article that I read and I'm wondering, so much of what we've discussed has been sort of formalized learning paths, where it's individualized, it's for the employee, and I'm wondering if you see a space for peer-to-peer learning and for that kind of less formal ways of learning?

Shelley: Absolutely. I think it's actually, I know L&D people don't always agree with this or know that this is this is true, per se. But the social, peer-to-peer learning is happening in every pocket of the organization with or without us. And that's actually something I think L&D folks should take on as a big part of their job, to create the opportunities for that, to encourage that. And to be able to really make that thing happening in the pocket of the organization and bring it deeper, bring it to more people bring it out to more opportunities.

One thing that I've done in the past is had social manager learning experiences where folks have this opportunity just to be in this social setting and talk about the experiences they're having the challenges they're facing, and it's this idea that knowledge is wasted when it isn't shared. And knowledge isn't held by the L&D team at all. We are the facilitators of experiences. The knowledge is within every single employee, and it's our job to unleash that, to create opportunities for that to be revealed and shared, and to really make it a robust culture for that to happen. And that's some of the greatest learning you're going to have happen in your company.

Mike: So Shelley, there's something that's been kind of bothering me through the conversation so far, maybe bothering is a strong word, but I want to come back to that point about...

Siobhan: Is it yucky, Mike?

Mike: I get a little bit of a yucky feeling inside.

Shelley: Where is this going? I can't wait to find this one out.

Mike: You just talked about it a minute ago, and we talked about it earlier in the conversation, it has to do with feedback, that being kind of the central point of a culture of learning of a place that promotes this sort of upskilling that you're talking about. But I think the the Achilles heel of this is that you have to have managers and leaders capable of delivering constructive feedback, not feedback on a project basis or feedback on a thing you did, but more of that sort of more coaching feedback. And I don't think that that is a capability that is widespread in many managers are at least one that they naturally have. It's one they can certainly develop. So how do you kind of overcome that? What tips do you have for helping managers be more coaching driven, be more feedback driven?

Shelley: I think it's an essential skill to teach all managers and employees. I think actually one of the places we get stuck is we only teach it to the managers, and sometimes we do that. I actually think that as an organization, one of the most important things you can do is teach everybody how to give and receive feedback. That's really important. We also often stop at the give or like, Okay, this is how you tell somebody they need to get better. No, no, no, no. We also need to talk about what it means to receive feedback. How we can assess that how we can internalize that well.

And I really believe that we need to help people frame feedback as something that's, that's rooted in helping them develop. There's a really famous lecture by a professor by the name of Dr. Randy Pausch, he, he passed on, but he's incredible. And I highly recommend everybody go check out his YouTube lecture. It's his last lecture at Carnegie Mellon, it's a series they still do with professors as they're sort of ending their career. And really tragically, Randy was ill, and it was his last lecture far too early. But one of the things he talks about in his lecture is this idea that when people stop giving you feedback, it's because they've given up on you, it's because they don't care anymore. And I think that is this unlocking, we can give to people this key to understanding feedback both as the giver and the receiver.

So to give people that freedom to know when you're giving feedback it's because you care, and it should be because you care, and you want to see them develop. And when you're receiving feedback, you should perceive it as that, it's because they care, and they're still willing to give you that feedback, and they want to see you grow and develop. So I think that's one of the most important things that an L&D team can help facilitate in a company. And I really encourage people to spend a lot of effort and time getting everybody in their organization wrapped around this idea that feedback is an important part of their job. It's something that they should seek, they should expect and that we should know that it's our role to give it not just to people we manage, but we should be giving it to our peers. We should muster up the courage to give it to our managers. I think it's so powerful.

Mike: All right. This is not an easy question, but maybe it's a good way to kind of bring all this together, because we've been through this period of the last year plus of really intense change in our companies. And a lot of that has been focused on the short-term, how do I come in and make sure that people are ready to work remotely on Monday when they're first starting this? So we've had this sort of cycle of kind of dealing with the next thing, but we've also over this time had enough time here to be able to think a little bit more long-term.

So how do we balance as you look ahead, the investment in some of those immediate needs, they may be specific reskilling or specific skills that need to be done, versus the sort of more long term future that you're advocating? We think about learning around, how do you balance those needs? And I know, it's not an easy question. But how do you do that?

Shelley: I think it's a really tough question. If you'd asked me that question. Even like four years ago, I would have still thought it was tough, because I think even then, we thought we were facing a lot of change, and it was difficult to predict the future. I think there's two ways I like to think about this, I think it's really important to have a plan, and to think about what's possible for the future and be really open to changing that plan.

I'm really fortunate, I'm married to a software engineer who he's a Scrum master, and he does agile development, and he's taught me a lot about how engineering teams have these big, big roadmaps and milestones, but they also regularly check in with themselves, and ditch, delete and just change the plan as necessary based on the situation.

So I think there's this balance. We can't not plan for the future, we have to make that plan, we have to do our best to predict, to have sort of situational awareness and think about what we think might happen and what we hope to accomplish, and where we hope to take our companies and our teams. But then we have to have this regular sort of check in, this gut check, and this willingness to say, well, that plan is terrible. That's not gonna work anymore. What do we do now?

So I also encourage folks to really take a page out of these like Scrum agile teams. I think it's an incredible way to work. And there's a lot of lessons that we can apply to other domains.

Mike: All right, this has been great. What Siobhan and I like to do kind of to close things out is do a little segment we call underrated/overrated, where we'll give you a few topics and we want your assessment of whether this thing is underrated or overrated. Feel free to give a little bit of riff on why you may or may not.

Okay you want to play along with us.

Shelley: Absolutely.

Mike: All right. I'm gonna throw a hardball your way the first one, and ask you if Canada is underrated or overrated?

Shelley: Oh, my goodness, seriously underrated. It's an incredible country. I was born in Canada, it's the best place. I absolutely love everything about it but the weather, how about that?

Mike: I appreciate that. I noticed that in your acknowledgments for your book that you want to thank the whole darn country. And so I was just curious.

Shelley: Yes, the whole darn country. It's an amazing place if you haven't visited I highly recommend.

Siobhan: I've got a hard followup for you here.

Shelley: Yes

Siobhan: Driving a Zamboni?

Shelley: Underrated. I was a Zamboni driver when I was in university and it was the best job I have to tell you a lot of fun. You know, you got to kind of drive a really cool machine. It's been on my resume for years because it always sparks conversation and questions and everyone's very jealous.

Siobhan: I saw it on Twitter and I was like, oh my god dream job.

Mike: That would be at the top of my resume, Zamboni driver.

Shelley: Although I have to say it was also very cold I would like were triple layers to actually go to the ice.

Mike: Now under more serious topics for underrated, overrated, the topic of virtual reality for learning. We've seen a lot of investment over time in this and especially in this last year, I think there's been a lot of innovations that have happened. Do you feel like virtual reality as a learning tool is underrated or overrated?

Shelley: I think it's underrated and has not realized its full potential. I've done a couple of really cool VR workshops and experiences that I would say are some of the best things I've created in the L&D space and it can be so impactful.

Siobhan: This one's kind of a well I, it's kind of either or, self directed learning, or company-generated learning paths.

Shelley: Don't make me pick

Siobhan: Sophie's Choice comes to the podcast.

Shelley: No, I can't choose. I think I want everything for everyone, all the learning. I think there's a lot of beauty and having self discovery. But it's never not been the case where someone hasn't been like okay, but Shelley, just give me the path. Just tell me what to do. So I like to make it possible for both to exist and to give people agency to make their own path, but to also free them from the the need to create it, and give them direction where they'll take it.

Siobhan: So I keep thinking of different phrases from these podcasts that I want to make into T-shirts, and I think that you just gave me your T-Shirt, which is "All the Learning. I want all the learning."

Shelley: Yes, I want that T-shirt. Let's do it.

Mike: We'll do the merch, you get a cut.

Shelley: Perfect. That's a great deal.

Mike: All right, how about this concept of ambiguity, embracing ambiguity, because it's become you know, as we this last year, even before the last year was sort of the code of modern business is to embrace the complexity, the ambiguity. Do you feel like we've gone a little bit too far? Is it underrated? Is it overrated? Or is there What do you think?

Shelley: I still think this one's underrated because that's where the growth is. That's where the opportunity is. It's uncomfortable, and it's scary. But that's where the best stuff happens.

Siobhan: So here's your here's your last one. Totally self serving. Last one, podcast learning.

Shelley: Honestly, underrated. I love podcasts. I'm a huge podcast junkie, I listened to so many. I just think we learn from others. And a quote I said earlier, 'knowledge is wasted when it isn't shared,' I think podcasts really give us the opportunity to tap into so many different perspectives and in different areas of expertise and amazing humans. So I think it's a it's one of my favorite ways to learn.

Siobhan: Well, you can come back anytime, Shelley.

So, I know that our listeners will probably want to find more about you and your work online. So what's the best way that they can learn a little bit more about you?

Shelley: Yeah, LinkedIn, I'm pretty active on LinkedIn. And I love to connect with people and meet them there, so add me. You can pick up my book on Amazon, The Upskilling Imperative: 5 Ways to Make Learning Core to the Way We Work. And yeah, I just ove connecting with people who care about this space and others who want to talk learning, all the learning.

Siobhan: Fantastic. Thank you so much for joining us today. Shelley.

Shelley: Thank you so much for having me. This is such a fun conversation, it blew by.

Mike: All the learning. I love that. And I do especially love the idea of doing some Get Reworked podcasts merchandise. I think that's that's a strong takeaway from today's podcast. How about you, Siobhan?

Siobhan: Well, of course, the T-shirts have to happen now because we promised Shelley the T-shirt.

Mike: I promised her a cut by the way, which ..

Siobhan: Oh, right, might have to talk to our publisher...

Mike: Legally, if we do it, we're responsible now.

Siobhan: Yep, yep. Yeah. But I really loved how Shelley was talking about how knowledge is wasted when it isn't shared. And it was just such a refreshing point of view to hear in the learning and development area, because so often it's individualized. And we don't think of that social aspect and how much more we can learn from our peers. Did you have any other takeaways other than T-shirts, Mike?

Mike: Yeah, I think more so than any content related was just what a strong advocate and eloquent spokesperson for learning's role in companies that Shelley is. I mean, I just thought that she did a really nice job of laying out the case of why learning is transformative, why it's central, to how businesses need to operate going forward. And I think more of those voices are necessary as we go forward, because there is a lot of baggage that comes with corporate learning.

You know, it comes out of it, and I think you addressed it Siobhan, that the corporate training, the compliance driven training, and there's just still that sort of gravitational force that pulls organizations down, particularly learning organizations. And I just think Shelley did a really great job of bringing that conversation up and showing where this fits into where we're going in business and where we're going as a society.

Siobhan: Honestly, I hope that Shelley's next move is creating that boot camp, the high school teacher boot camp for L&D people. That's just me, I'm speculating.

Mike: I'd love to see CEOs and C-suite execs thrown into a high school classroom. I would watch that reality TV show.

Siobhan: Totally, totally.

Mike: All right, there's our next multimillion-dollar business idea Siobhan, just giving it away for free.

Siobhan: We're just giving it away ...

Mike: All right, tune in next time for more business ideas you can steal from us.

Siobhan: Great talking to you, Mike.

Mike: Talk to you next time Siobhan.

We encourage you to drop us a line at [email protected]. If you have a suggestion or a topic for a future conversation, we are all ears. Additionally, if you like what you hear, please post a review on Apple Podcasts or wherever you may be listening. And be sure to share Get Reworked with anyone that you think might benefit from these types of conversations. And then finally, be sure to follow us at Get Reworked on Twitter as well.

Thank you again for exploring the revolution of work with us and we'll see you next time.


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