Rob Hallman and the art of the ‘squiggly’ career

From a love of Byzantine art to a career as a lawyer now working for LinkedIn, alumnus Rob Hallman (’96) has not exactly followed a linear career path since his time as a history undergraduate at McMaster. 

“At Linkedin, we spend a lot of time with researchers studying career paths, and our CEO likes to say that paths are very rarely a straight line — he likes to call them a squiggle,” Hallman laughs. “A squiggle is not a bad thing at all — and my career was definitely a squiggle.” 

Following his history degree at Mac, Hallman, who grew up in Mississauga, knew he wanted to continue his studies — and chose to pursue graduate studies at NYU, where the museums and galleries of New York City would be on his doorstep. 

And, while he was working on his graduate degree, he ended up at one of the best: the Metropolitan Museum of Art, specializing in Byzantine art. (His favourite pieces of art are still the miniature Byzantine mosaics he remembers from an exhibit that he worked on.) 

But a class in art law and an opportunity to work on projects with the Metropolitan Museum’s legal department threw the squiggle into his career plans. 

“We were working with issues related to a large international exhibition, as well as acquisitions and new gallery planning, and I realized it was a really interesting job,” Hallman says. “I also recognized there weren’t a ton of job openings for people who wanted to be curators in Byzantine art — so I went to law school, thinking that maybe I’d end up back at a museum at some point.” 

Where he ended up was LinkedIn, as a VP on their Legal team. Along with working in regulatory compliance and product counselling, part of what his team does is support the groups within LinkedIn that focus on AI. 

So he’s got a lot of thoughts about AI. He’s also got thoughts about the value of a humanities education, and some great memories of being at Mac. 

We sat down with him to find out more. 

How does your background in museums and art filter into your work now?

I think a lot of the effective people in the work I’m in now have a lot of the skills that we develop in studying humanities — they’re effective communicators, they can write well, they can do more than a surface-level analysis of a text, or, in my case, a regulation. And you definitely learn to work well with others!  

And outside of direct work, it’s really important to recharge with those things that you’re passionate about, from classics, to history, to art, to music — all the things that enhance life. I mean, my office is right across the street from the San Francisco Museum of Modern Art! I still get something out of those areas that I studied at Mac — they may not be as much of a part of my day-to-day now, but museums, reading, having something outside of work that you look forward to each day is really important. 

What surprises you about your job? 

When I joined LinkedIn 11 years ago, I had some concern about what it would be like being an in-house lawyer rather than working at a law firm. Would it feel like it was routine, or would I be doing the same stuff every day? 

It’s not like that at all. I feel like I’m learning something new every day. We’re figuring out how to navigate a very complicated regulatory landscape, as well as looking beyond the regulations to see how the world perceives tech companies and their role in what AI is going to mean to the world of work. 

It’s really interesting, because it feels like what I read about in the news is what I’ll be working on at work as well.  

How do you see humanities grads fitting into a work landscape that’s been changed by AI? 

I think about this a lot, both because of my job and also because I have kids who are college age. 

I think AI is going to change what careers look like, but I’m not sure how. I think that everyone in humanities – and other areas – should develop a fluency in AI and actually put in effort to trying different AI tools to see what works and what doesn’t, what adds efficiencies and what seems like it’s not worth the effort. 

At LinkedIn, we’re studying a lot of job openings and skills that employers are looking for, and there’s a ton of hiring for people who have some AI skills and can bring AI into the types of jobs that didn’t have it before – but that’s not going to be the full story, and obviously we don’t want AI to be the only creative energy for the future. 

I’m still telling my kids to study what they’re passionate about, because that’s what’s going to keep you going through the twists and turns of your career.  

The skills that you learn in the humanities will be the ones that continue to be important, like the ability to lead a group, to communicate effectively, to do deep analysis and research. 

Readying yourself by bringing enthusiasm and energy and developing some AI skills that will help bring value to the place you’re working will be helpful, no matter what career you choose. 

As AI starts to become more and more mainstream, I’m reminded of the beginning of the internet – and now we’re in the middle of another huge revolution. What do you think? 

Microsoft leadership likes to compare AI to the printing press and electricity, and it feels like that to me in terms of the diffusion of AI tools – but it took a lot of years from when electricity was discovered to having the infrastructure to use it in factories and homes. With the internet, there was faster adoption, and the adoption of AI feels even quicker to me.    

I think there will be growing pains for sure, and technology might arrive faster than we figure out the best ways to deploy it, or what new types of jobs are going to emerge from it, so there will be challenges as we adopt it. 

But I think we’ll create opportunities as well, which is why I think it’s important for everyone to at least use it, and not just shy away from it. 

Is there anyone who kept you going as you followed the squiggle of your career? 

I’ve had really amazing mentors at each stage of my career journey. At Mac, in grad school, at the museum, and here at LinkediIn, too. Following their example has been inspiring throughout the journey. 

Another thing that keeps me going has been the people I work with – the early years at a law firm can be pretty painful, with long hours and stressful projects, but if you’re able to find the fun and have a good camaraderie with your colleagues, even the hard projects can be inspiring in their way. 

Finding a great group of people or some co-conspirators on a crummy project makes it much more manageable and fun.  

Speaking of fun professors, what are some of your favourite memories of Mac? 

I have very fun memories of history professors, like Professor Kaczynski and Professor Aksan. I had some great religious studies classes with professors Widdicombe and Mendelson. I had other great professors too, of course, but those are the ones that stand out. 

I lived in Whidden Hall for two years, and I have great memories of Whidden shenanigans — and the great friendships and roommates. 

I definitely overate at Village Pizza, which was in Westdale. I did intramural inner tube water polo — I mean, I lived with actual athletes, but that was the sport I could excel in. I also really liked running or doing bike rides on the escarpment in Dundas. 

Mac was a great experience. 

Do you have a personal motto that you’d like to share with humanities students and new grads? 

“You get out what you put in.” I think it’s almost always true that if you bring energy and curiosity to something, you get more out of it. I remember courses or tasks that didn’t seem like they were going to be interesting, but when I actually dug in and invested time and energy in them they turned out to present a new opportunity or create a new connection, or inspired me in some way. 

So rather than being passive, if you bring energy and curiosity to something, you get something back.