Five Things Friday: Jay Goldman, Managing Director at Klick Health; wearer of many hats | FreshGigs.ca

Five Things Friday: Jay Goldman, Managing Director at Klick Health; wearer of many hats

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Five Things Friday is a departure from the interviews and features we typically post. Part conversation, Part Proust Questionnaire – but with just five questions, Five Things Friday (hashtag alert! #5TF) shows the lighter (and sometimes sillier) side of our interviewees. We’ll be talking to everyone we can get our grubby little hands on; it’s our way of introducing you to the communications, marketing and creative cognoscenti who rock their respective industries. This week, Joanne M. Brathwaite talks to Jay Goldman, Managing Director of Sensei Labs at Klick Health – and wearer of many hats.

You describe yourself in multiple titles (technologist, designer, speaker, author…generally swell guy). How did each incarnation come to be? Which is your favorite one?

I feel like the list has slowly built out over the years, especially the middle bits. I’ve always tried to live up to the generally swell guy part (hopefully it’s working!) and the technologist in me has been there since a really young age when I used to sit and play Atari 2600 for hours on end. My dad was in computers from before I was born—somewhere we have one of his college textbooks with my mom’s contractions timed and noted on the inside cover as she gave birth to me.

My mom has been an artist since art school, so the technology and design parts came naturally. So did the authorship, which I would say is a direct outcome of having been raised by bookworms. The speaker part was something I fortunately discovered early in my career as a love of public speaking that has remained true to this day, whether an internal talk at Klick or on a major stage like TEDx.

Picking a favorite is tough, since they’re all part of me. There are parts that aren’t listed there too, of course, like husband, father, or friend. I think I’d have to say generally swell guy, since it informs everything else. It’s a constant reminder to try to live up to the old adage about treating others like you’d like to be treated. If we judge a person by the company they keep, I’d say that’s working out incredibly well for me ☺

Did you always know what you wanted to be(come)?

I think I’m extremely lucky to be able to say yes. I followed very much in my father’s footsteps, who was a technology entrepreneur before the Internet. I grew up around computers and learned to write code at a young age in Apple’s awesome HyperCard tool. I always knew I would do something related to computers, but the specifics weren’t clear. My love of technology continued through high school, including co-founding a software company in grade twelve, but it wasn’t until I was applying for university that I discovered the field of User Experience.

I fell in love with the idea of human computer interaction – of specializing in designing the experiences that people have when using software and hardware through an understanding of technology, psychology, and sociology. That led to a degree in Information Systems and Human Behavior, which led to a job at IBM on one of their User Centered Design teams, which eventually led to where I am today.

Are there any digital/marketing trends you’ve come to notice in your years in the industry? Which do you see as positive? Which give you pause?

There’s been a strong push toward design-rich technology or even design-led technology, which is a long way from the days of terrible interfaces that people just mutely suffered through (or not so mutely sometimes!). I think Apple has a lot to do with it, but so do companies like Airbnb, which was founded by a group of designers.

It also mimics, of course, the much larger trend toward the digitization of our lives. Websites were often an afterthought for marketers when I started my career. The digital agencies were given a print piece and asked to design a website around it, and now we’re leading the charge and producing print pieces as an afterthought. YouTube was largely ignored by brands when it appeared, then it was somewhere to upload your TV spots, and now it’s a place to build an entire campaign that may include airing the videos on TV.

Here’s a question not often asked of men, but with your busy schedule, travelling, and the wearing of multiple hats, how do you manage to juggle family and work?

It should be asked of men more often! Being away from your family is tough regardless of your parenting role. Technology helps a lot; FaceTime isn’t the same as being there in person, but it’s a whole lot better than a phone call. The key, though, is putting away the technology when you are together.

(Unplugging isn’t a prerequisite for me; I long ago accepted that my life would end up involving technology in pretty much every aspect, so I don’t feel the need to switch it off or hide it away. I love the feeling of a printed book in my hands, but I also love the convenience of my Kindle. Everything in moderation is key: there’s a time to be tweeting, emailing, surfing, and chatting and there’s a time to sit and read.)

I do try hard to leave my phone and laptop alone when we’re having family time. We go for walks or do projects together instead of vegging out in front of a screen. If we are in front of a screen, we’re all sitting on the couch together watching a movie. Making family a priority doesn’t mean it has to have the biggest slice of your time, but it does have to have the most important ones.

Have there ever been any opportunities that you’ve not taken and regretted?

If I look back at my life so far — personal and professional — the only thread I can really weave through it is of opportunities taken. I’ve always tried to say yes to new things that have come my way, which has led to the strange but awesome path behind me.

I have a theory about this that was inspired by Barry Schwartz’ excellent book The Paradox of Choice: although we think we want to have more choices available, we’re actually much happier when we have fewer choices to make. You can apply it all the time in your daily life. Think about looking over the menu at a restaurant, trying to choose something to order for dinner. You can either review every item, weigh the pros and cons, negotiate with your tablemates to share, and inevitably end up disappointed that you didn’t order a different item, or you can close your menu when you see the first thing that sounds appealing. It removes the ability to have post-decision regret because you don’t actually know what the other options are, which almost always leaves you to enjoy the choice you made more.

Do more of that.


Jay Goldman is a speaker, technologist and co-author of the New York Times bestselling business book  The Decoded Company (Portfolio/Penguin). He is currently the Managing Director of Sensei Labs, a Klick Health spin-off dedicated to helping companies evolve and execute faster using proprietary technologies and ideas from his book. Earlier this year, he was billed by Medical Marketing & Media (MM&M) magazine as one of the 40 inventors, strategists, advocates and wonks who are challenging, disrupting and otherwise transforming the healthcare business.


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