The Vague Imperative of AI: Ex-LinkedIn VP of Talent on Pitfalls to Avoid

Dimitri Boylan

Welcome to another episode of the Talent Transformation podcast. Today we’re joined by Jen Shappley. Jen has 15+ years of experience building high-performing teams across the globe. She has most recently been the vice president at LinkedIn for talent acquisition, talent development and talent management. Jen. It’s great to see you.

Jennifer Shappley

Good to see you, Dimitri.

Dimitri Boylan

It’s been a long time.

Jennifer Shappley

Yes, it’s been a minute.

Dimitri Boylan

So the last time we were together, you were heading up talent acquisition at Express Scripts. And I think at the time, they were Fortune 20, maybe. And, yeah, super-fast growing at that moment.

Jennifer Shappley

Yeah. We were growing like wildfire back then.

Dimitri Boylan

And so then you went to LinkedIn, and that was, I guess, a decade. You were there for ten years, right?

Jennifer Shappley

Yeah, that was a real hard turn. I’m from Tennessee, so that’s the Tennessee connection. But I was living in Saint Louis. I had been there about eight years with Express Scripts. And I was really interested in getting into tech. There wasn’t a lot of hiring happening in the Midwest for tech at the time.

But I got the call from LinkedIn and thought ‘I’m going to go give it a shot and move out to Silicon Valley’. I didn’t really plan to move to California and wasn’t sure how long I would stay out here, but ten years gone, time flies. Yeah, here I am.

Dimitri Boylan

So, was it very different recruiting in Silicon Valley? Were the expectations very high? Was it incredibly difficult to hire technical people? Tell me that story a little bit.

Jennifer Shappley

You know, it’s interesting. I think there’s a perception that it would be totally different or a lot more difficult. I would say it’s different. And I think, what you know about Express Scripts, and I know from being there, is that Express Scripts was going through a hypergrowth period and so there was a lot of building the plane while you’re flying it. You’re figuring things out for the first time.

Jennifer Shappley

You’re not following a playbook. You’re writing the playbook as you’re going. And so actually, that experience was really helpful and really relevant to coming out to Silicon Valley and hiring out here. And I think at the time people would talk about like, ‘oh, if you haven’t been in tech or you haven’t done this, you’ll struggle or there was concern around that.’

Jennifer Shappley

I think a lot of what that really came down to was: are you able to build when there isn’t a playbook to follow? And so the time at Express Scripts had been incredibly helpful for that, because that was so much of what we were having to do there. The type of talent was really different. And so then you get out here and there’s this competition for incredible top-tier technical talent.

Jennifer Shappley

You’re certainly recruiting a different profile of individual when you’re talking about hiring at LinkedIn. But I found what was really so important, and what helped with the transition was that ‘can you exist and thrive in an environment where there’s not a manual that somebody is handing you on how to do.’

Dimitri Boylan

This, right? There’s no detailed direction given to you. And I think sometimes people can sort of freeze in that situation and say, ‘Maybe I don’t go either direction. I don’t know what to do.”

Jennifer Shappley

They’re looking for somebody to tell you what to do, and I think.

Jennifer Shappley

And so it is truly like – and I’ve thought about this – like the best idea wins. And people can get frustrated with, ‘well no, I had this idea or I want to do this’ and they don’t know where to take it. And it’s, I think what’s rewarded out here really is being bold and being able to go and make things happen. And then, you know, when people see, like, ‘oh, you made that happen and it worked really well’, then the accolades come. But it requires a certain level of confidence and boldness.

Dimitri Boylan

Yeah, right. Well, Express Scripts probably prepared you for that in some ways, because it was in hypergrowth. It was technical too. I mean, it was online prescriptions, so it was part of the dotcom sort of evolution of business. But I assume Express Scripts was large volumes of people. You went from thousands of people to hundreds of people. Right?

Jennifer Shappley

Yes. Express Scripts, the volumes… it was a different kind of game you’re playing. You’re having to think through at large volumes when you’re hiring this many people. How many are going to show up on their first day based on that? How many do you need to have going into background checks? How many do you need to be reaching out to?

And so there is a certain amount of precision and strategy that goes into the funnel management when you’re doing volume hiring at that scale, which is different than what the challenges necessarily were at LinkedIn because the volumes were different – although the volumes at LinkedIn were ultimately thousands of hires over the years. But it’s it’s a different profile of hire. It’s a different strategy.

Dimitri Boylan

So, certainly, you weren’t overhiring product designers in the anticipation that, you know, 15% of them would not show up, right? Did you feel like the competition in the valley was of a different nature? The competition for the talent?

Jennifer Shappley

Absolutely. There are a lot of great companies out here. So, if you’re a product manager or designer, engineer, you’ve got a lot of choice. And so you also see a different pattern. People move around a lot more out here than you would have seen in Saint Louis, where the tenure at the organization was longer as well.

And so it really becomes… it’s not just about recruiting talent. That’s certainly really important. And what are your strategies around how you were attracting talent… But it becomes retention too. It’s full-on talent wars because it’s not only about ‘how are you attracting folks?’, but then what are you doing to retain them in a really competitive environment?

Dimitri Boylan

And how much did you think about that retention at the point when you were hiring?

Jennifer Shappley

Quite a bit. And I think it’s important for any talent acquisition leader not to just think of one side of the equation. It shouldn’t just be about getting people and throwing them over the fence. And then kind of going back to recruiting.

While that certainly has got to be your focus, you’ve also got to think long term. If you’re working for a great brand, like LinkedIn, then you’ve got to be cognizant of the message that you’re delivering to candidates. It’s got to be authentic. It only works for so long if you’re kind of putting out a message that people don’t experience once they’re at the organization.

And that’s such a huge part of retention. You need to make sure that your message is authentic and that when people come, that’s how they experience the organization. And so I think it was really important to make sure that people stayed at LinkedIn and were happy at LinkedIn. Because otherwise, that message starts to get out there and the valley is a small place.

Dimitri Boylan

Yeah, yeah. And so you were responsible for talent acquisition, but also a couple of other things. So, did that happen organically, or did you come in with more of those responsibilities from the get-go?

Jennifer Shappley

No. That happened organically. So, over the last couple of years, I had expanded beyond just the TA responsibility into talent management, talent development. And it’s starting to happen at several organizations I’ve seen. I’ve seen other TA leaders expand the remit and take on broader talent.

I think there’s been this shift, especially as organizations go from maybe hypergrowth periods towards looking at the entire talent lifecycle. Having to look at it from the point at which you are hiring throughout the talent lifecycle has become a strategic shift a lot of organizations have made.

Dimitri Boylan

Yeah, well, I think also talent acquisition is just a great proving ground. You can get it right and you can not get it right. And it’s also a place where you are forced to work within the greater economy and the greater market. You can’t make your market. You have to make your response to the market.

And I think that that sort of drives a little more agility and flexibility in people who come from TA. I think sometimes when you’ve just been inside the company in a purely internal role, you have a tendency to maybe feel like you can reorganize the whole world around the way everybody agrees it will be. And, to some extent, talent retention is also about dealing with what’s going on outside the company, right?

The company down the street that’s expanding the brand that’s getting more play in media and your brand, and those things are just real factors that I think in talent acquisition, you just get very used to dealing with.

Jennifer Shappley

Yeah, there’s definitely an agility and a resiliency that comes from being on the TA side. Your job is never finished on the TA side. You know, you’re a recruiter. As soon as you fill one req there’s ten more. And so you build up this resilience around that.

In the same way, though, on the talent management development side, the internally focused HR groups, there are longer cycles to things that you have to get used to and how do you manage through those? There’s certainly a lot I learned from working with groups that had more of that, like a kind of longer tail to what they do. I think, in general, it’s just good for talent leaders and HR leaders to move around.

Dimitri Boylan

To move around. That’s what I was about to say.

Jennifer Shappley

I think that’s where it goes. It’s just good for all of us to learn more about the other pieces of the pie.

Dimitri Boylan

Yeah, absolutely. And so when you were doing talent development, was that driven partly because you were struggling to find the talent that you wanted or the capabilities that you needed in your organization at that particular time? And was it born out of a need? Like, ‘okay, we’re getting these types of people, but they don’t quite have the skill sets that we need,’ and you started to try and move the skill sets of the organization around?

Jennifer Shappley

I wouldn’t say there was a struggle there, I wouldn’t say there was a specific need to close the gap in that way. It was the knowledge that, because of how quickly things are changing, you got to invest in your own talent.

It’s not a healthy way to look at your organization and your talent to think you’re just going to pull one lever. You’re just going to buy talent. You’re also probably not just going to build talent. Because if you’re only developing and not looking at the external markets, you’re missing that outside influence and creativity that can come from bringing in new ideas.

So, I think it was just a place of wanting to make sure we’ve got a healthy balance and we’re looking at them as two different levers, all in pursuit of the same strategy. How are we continuing to grow, develop and invest in the talent we have, while also mirroring that with ‘how are we thinking about making sure that we continue to acquire best-in-class talent as well?’

Dimitri Boylan

How well did you sync those two worlds together? You have some organizations where talent management and talent acquisition are so fully separate from each other that one doesn’t really inform the other. And then the ideal state, of course, is you know exactly what you need and you know exactly what to do to make your internal workforce able to do it. And exactly what it costs to go out and find it somewhere else. And you’re making these decisions for each role: ‘okay, this role will develop. This role we’ll hire. This role will transition through mobility with a little bit of development. But if it doesn’t succeed within six months, then we’ll hire for it.’

Was that it? Did you have a unified top-down talent strategy or was that something you were working on?

Jennifer Shappley

So we had a unified talent strategy. But I will say, I think that ideal state is more of a guiding light than it is a realistic destination, if that makes sense. And I would imagine, I think a lot of organizations are in this place right now where the future is changing so quickly.

You and I, we were probably talking about this 10, 15 years ago, when I was at Express Scripts, Dimitri. The workforce plan: ‘once we get that multi-year workforce plan, then all of our dreams will come true. Then we’ll be able to have robust talent acquisition strategies and development, etc.’ And I think, ironically, over the years, instead, of it all getting to the place where that became a reality, it’s probably become even harder to have – especially in the last couple of years, because the landscape has been changing so much.

A few months can make a difference between, ‘oh yes, we need to hire these people over the next three years.’ And a question of, ‘oh, is technology going to replace that? Do we need to think totally differently?’

Jennifer Shappley

So, I would say this idea of a unified talent strategy was certainly something that we had in place. But the reality, I think, for most organizations these days is they’re still grappling with how much is technology going to impact where we need to develop, where we need to hire versus where maybe we bring in tools to help solve for some of that.

Dimitri Boylan

Now we’re getting into artificial intelligence. And it’s really hard at this very, very early stage to imagine the workforce of 2028, right? I don’t know, it’s probably smaller. Unless you found a way to leverage artificial intelligence to significantly expand your business and your market share, which you could do, because AI does allow you to possibly do those things, too.

It’s also going to require a skill set that’s not really been defined yet. Or at least to orchestrate it inside the organization, but also just a change in every individual employee skill set. Right across the whole board. So have you been thinking a lot about that? Was LinkedIn thinking about that over the last few years? Because ChatGPT caught a lot of people by surprise, even in the tech community, right?

Jennifer Shappley

What I can speak to is, how I’m thinking about it… Are our workforces smaller in the future? Possibly. But I’m kind of going down the path where you say ‘okay, unless organizations can expand their portfolios and what they’re offering…’,

I ultimately can’t predict the future. But I’m a big believer in humans and our ability to create. Every time there has been some kind of revolution, whether it be like industrial revolution, etc., there have been new ideas and new products that have come out of that.

We’re so deep in the middle of such a massive shift right now, I do think it’s hard to know what new ideas may ultimately come out of this ten, 15, 20 years down the road. But I believe they will.

I think a lot of the roles that we have today in our organizations are likely going to change. In the short term, that might mean or feel like some of these roles are going away. I think in the long term, it’s just they’re going to be different.

And so like what we ask of entry-level and early in career employees, what they are doing will look very different than maybe how folks started their careers even a few years ago. But I just actually think that humans are really adaptable, resilient, creative beings.

Dimitri Boylan

Yeah. We like to do something. We don’t sit idle.

Jennifer Shappley

We don’t sit idle.

Dimitri Boylan

But now, when you talk about AI and skills and the huge transition that’s going to occur right now, how are you thinking about it in terms of yourself? Like, how are you approaching it? Are you reading up a lot on artificial intelligence? We’re all doing that. We’re trying to keep up with what’s going on. Do you think that there’s going to be a fundamental rethinking of talent acquisition?

Jennifer Shappley

Yeah, absolutely. And I think there has to be. Now, that doesn’t mean that every idea and every use of AI is a good one. And we need to challenge and be thoughtful of not just chasing technology for technology’s sake, which I think can be a trap that a lot of us can fall into sometimes.

Dimitri Boylan

Yeah, especially with some organizations where some managers are under some high pressure to actually do something with AI. And it’s kind of a vague imperative.

Jennifer Shappley

Right. So, it can feel like, ‘okay, I just need to show that I’m doing something, something with AI, in order to look kind of…

Dimitri Boylan

Modern.

Jennifer Shappley

Leading that imperative. Modern. Exactly. ‘That I have something to talk about on stage’. But I don’t think this is a moment or a point where you can’t have a point of view. And so, certainly, like you said, educating myself, listening to podcasts, playing around… I think the most important thing is make sure you’re experimenting with new tools. So, I use some form of AI every day.

Understanding what’s possible, both with the silly and what it can do in the serious. I think, the most important thing I would say for folks is just make sure you are you’re playing around, you’re experimenting with tools, and you’re forming a point of view so that you don’t get trapped in this place of like, ‘oh, I’m being told I have to use it, so I just need to go pick something off the shelf.’

Jennifer Shappley

I think, as talent leader, I would never want to be in the place where I feel that imperative, where I feel the pressure to be using AI, and I don’t have a strong point of view on where we should be using it. And where we shouldn’t. Because then you’re in this place where you’re just feeling the pressure and like, ‘okay, I’ve got to go do something’.

But showing up to that conversation with some conviction, a point of view on ‘here’s where we need to use it.’ – whether it be replacing the administrative, getting out of the routine processes… ‘what are the things that add no unique value by having our employees, our most valuable resource, focused on it?’ Coming in with that point of view gives you a lot more control in that conversation versus just feeling like I’m being told I have to use it. So I’ll kind of stick it somewhere.

Dimitri Boylan

Well, I like that point about unique value. Because everybody is going to have AI, so it’s really going to come down to unique value in what is very specific that you can do with it that is not what everybody else has done with it. Certainly, there’s a certain number of things that everybody will do with it and that will form a benchmark of maybe efficiency, productivity at some level, but it won’t actually cause anybody to stand out. It’ll be a common denominator at some point.

Jennifer Shappley

Yeah.

Dimitri Boylan

Yeah, that we have a certain level of AI, there’ll probably be a little bit of a spectrum in terms of who deploys sooner. So there might be a little period where you have some competitive advantage just because you were a little quicker to use AI. But that will probably go away. That’ll be a short-term competitive advantage. And I imagine that the long-term competitive advantage will be basically how unique are the things that you do with AI that’s specific to what makes your company successful?

Jennifer Shappley

I agree. You can’t go into it, and this is true with any technology, this is true if you’re implementing any kind of technological solution: what is it you are trying to solve with it? And so I think for organizations, if you’re not clear on what are you trying to deliver through your candidate experience, how are you measuring that? Is that a differentiator for you that you want to have an incredible candidate experience?

Well, that’s probably going to drive you a certain way or not, as it relates to your use of AI and making sure that you’re using it in a way that’s improving it, not just in a way that’s driving efficiency. It’s being clear on that before you go and try to implement tools. I think it’s really important.

Dimitri Boylan

Right, Let’s just talk quickly about skills because skills are sort of part of the AI story. Companies have been struggling to make skills very useful inside their organization. And, you know, part of that is probably the fact that these roles are going to be changing a lot right now.

And if you get the skills right, it may help you with that. But it may also make it more difficult for you to really decide what it is that you need to do a job. And how do you quantify what is required for each role? I mean, have you spent a lot of time on the skills topic over the past few years?

Jennifer Shappley

Yeah, I have and I agree. I think a lot of organizations struggle with taking it from theory into…

Dimitri Boylan

Practice.

Jennifer Shappley

Reality, action and practice. Exactly. What I like right now, as far as how the skills movement is evolving, is it focusing more on the tasks of the job and getting into, ‘okay, what are actually the actual tasks and responsibilities that individuals are going to do in these roles?’

I think it is more tangible. It’s changing a lot too, so getting into an understanding of the job tasks, it’s just a smart place to be spending time at a point where more automation and AI are coming in, and it’s going to change the tasks that are needed. But I think it is more practical in reality.

Dimitri Boylan

Yeah, bring it down to earth.

Jennifer Shappley

Exactly. And so I like that migration of where it has gone, because what I find that people really struggle with skills is the skill language can sit really far up here and they aren’t getting enough into proficiency – and proficiency matters a ton when you’re talking about the roles and the level of the role, etc..

So, just saying that communication skills are needed doesn’t really get to the point of being able to actually do something with them. I think it has been really helpful in bringing some more structure to how we interview, what we need to focus on in the interview, and what we need to focus on developing. And so I think it was a good bridge, but I like where the focus is now on actually getting into the tasks.

Dimitri Boylan

Yeah, into the tasks. And also, I would add one thing that, if it’s something that you’re really not going to be evaluating, it’s probably not going to be useful. Project management skills are irrelevant if you’re not really measuring somebody’s project management skills. Otherwise, it’s just information that is not really useful. And it’s kind of hard to get it to be used.

Jennifer Shappley

Exactly.

Dimitri Boylan

Because you don’t actually measure it. And I think the harder skills… If you’re a customer service rep, customer communication becomes really important and you’re probably measuring it. If you are a programmer, you’re coding skills can be measured, they can be tested, they can be rated, they can go up and down over time. And so that becomes our proficiency of the job.

But I think you’re right. I think people sort of threw the skills ontology on the wall, like the spaghetti on the wall. And then you look at it and it’s too much information. And not enough of it is relevant and useful to what you’re actually doing every day, the decisions that you’re making every day: ‘who goes into this job, who comes out of this job in the interim? Who gets trained to be in that job or who doesn’t get trained to be in that job?’

Jennifer Shappley

Yeah. I think you’re right. I agree on the measuring piece, because certainly some skills matter more than others. And it’s: is this a core part of the role and something that you’re going to be held accountable to? And the skill piece, again, is ultimately about what are the skills that are required in order to do the tasks that are a part of the job.

And so it still comes back there. And so, I think we probably have gotten a little too sucked into the hype around skills without bringing it into the practicality.

Dimitri Boylan

There’s always a hype wave, and managers and leaders need to recognize the hype wave and then sort of understand how to pierce that haze and get to that point where you really doing tangible value-added things. And of course in AI this hype wave is a huge wave. It’s very hard to get through it because there are a lot of people contributing to the hype.

Skills was hyped in talent acquisition and and learning. But AI is being hyped across the globe by everybody, including countries, so it’s gonna be harder to cut through that.

Silicon Valley is rolling out new AI companies basically every week right now. Do you think there’s more pressure on to leaders in the valley to use AI than in the rest of the market? Because the valley is very aggressive about using technology – they don’t wait for, you know, the paint to dry.

Jennifer Shappley

Yeah. I think the pressure on AI is getting to a point of being fairly ubiquitous, but I do think the pressure is higher out here with any tech organization.

I think you’re in a position of wanting to be able to show others how to do this. And, it’s more at the forefront of every conversation. But I think it’s getting there in most industries.

Dimitri Boylan

Well, I have discussions with a lot of companies that say, ‘we don’t want to be on the bleeding edge of this. We decided as a brand – we decided as an organization – that we’re going to try and be a close second and see how things break with the EU law that’s coming up, coming into effect.’

And, if you’re a very large organization, sometimes it takes time for the organization to consume all of the knowledge and then actually move out the policies that then allow the people to do things. So, I definitely talk to some companies that say, ‘we want to be second or third, we want to be on the podium, but we don’t want to be…. We’re not going to try and be first.’

I think in the valley, it’s always we’re going to try and be number one. We’re going to be first. We’re going to, you know, our credibility here in the valley is always around who’s first.

Jennifer Shappley

Yeah, I think there’s that first mover benefit, advantage. I think it probably comes down to risk profile of the organizations too. So it’s just, as an industry, as an organization, what’s your risk profile?

Dimitri Boylan

Well, we’d like to have you back when you start your next thing and hear about that. It was great to see you again. It’s been a decade.

Jennifer Shappley

I know, we’ll catch up in ten years.

Dimitri Boylan

We should. We should maybe do it sooner than ten years.

Jennifer Shappley

I’ll call you from Mars. I’ll probably be living in a colony on Mars.

Dimitri Boylan

Fantastic. Listen, it’s so great to see you. Thanks a lot for coming on and sharing your experiences with us. And good luck in the next thing that you do.

Jennifer Shappley

Thank you, Dimitri.