8 Product Designers share what’s most challenging about what they do.

Over the past two years we’ve interviewed over 100 creative professionals about how they do the work they love. Through that we’ve interviewed a number of designers who have shared how they got started in design, their process and tools for making things happen and what they find most challenging in their work.

We thought we’d round up a few of our favourite responses from the interviews we’ve done. Enjoy.

Geoff Teehan, Design Director at Facebook

“One is that this is a very large organization and as big as it is, it’s relatively flat in its architecture. There is a lot of autonomy given to the people doing the work, which is great. While there is process, there’s not so much that it gets in the way of doing the work. There are also a ton of different working styles here. Sometimes, those things can be difficult to work with. There are people who have worked here for a while that are very proficient and good at what they do. They know the ins and outs of this place and they like to work with a lot of autonomy and relative isolation; much like a lot of designers. Some of them are very successful at that. I think that’s okay, but I think as the company has grown, that becomes a little bit more challenging to work within. I really prefer and think we can do better work when we work in pairs or we collaborate a little bit more.

Figuring out ways to get people working in a more collaborative way has been a challenge. You can’t just put two people in a room and expect them to work together. There are certain dynamics and fit involved. There are also times in a project where you really do need to just sit, put your head down and do some work. There are also times when you need to come up for air and regroup with other people, get other opinions, and jam on ideas.”

Read the full interview.


Jessica Hische, Letterer & Illustrator

Photo by Helena Price

“My biggest challenge has just been pushing myself to ramp back up to the level that I know I will be best at. Rather than being overly cautious and just taking on a few projects here and there, if I push myself to take on more work, I will do more work and I’ll probably be happier. I’ll be more effective at my desk and not fiddling around with email for half the day.

Time management is a lifetime issue and once you feel like you’ve got it handled, something happens in your life that completely changes how everything is framed. I’m still in the stage of working out my current system. I want to feel like I’m really maxing out my career stuff, but also really maxing out family stuff too. I think I’d be able to forgive myself for a few years of not being the most productive designer, but I couldn’t forgive myself for a few years of not being the best parent.”

Read the full interview.


Alexander Mayes, Product Designer at Instagram

“At Instagram, everybody is just pushing for super amazing design all of the time. We have some of the best designers, like famous designers that work here. You get to sit next to the people who you’ve really looked up to all day. Then all of the sudden you’re showing your work in a design review with Kevin Systrom, and all that you can think about is the first Instagram post that you ever posted and how 5 years later you’re designing for an app that has been such a big part of your life with the people that literally created the first version, it’s all kind of unreal. For me, coming from a small town and then a start up it’s… I mean I didn’t go to Stanford, I didn’t do all this crazy shit that people out here are used to. Sometimes I stop and look back and think “this is intense.” It even makes me smile to this day.

So I love getting feedback from other designers here. Some designers that I’ve worked with in the past have been really egotistical about getting feedback, but I know the people at Instagram that are critiquing my work are just so good, so it’s great for me. I think what I’m trying to do now is to put myself at that level too, and realize that I don’t have to take all feedback and learning how to distil it better and be quicker on product thinking. Not really execution but getting to answers faster when it comes to the product. It’s really important because if you spend hours thinking of product solutions you’re never going to get anywhere. That’s probably one of the main things that I’m really focusing on right now is how to be a better holistic product thinker.”

Read the full interview.


Huda Idrees, Head of Product & Design at Wealthsimple

“For starters, we’re trying to do a lot with a very small team and growing quickly. We acquired a brokerage of our own, so now we’re this company that buys other companies, and we’re just a year and a half old. There’s a lot of priorities that all seem equally important. The toughest part has been looking at data trends, but also paying attention to our instincts, which have served us really well in the past. Figuring out what we should work on next and where we’re going to spend our limited resources has been a challenge.

Finding designers has also been a personal challenge for me. There are very few people who are excellent at all facets of design, who can come in and really take a project all the way ’til the end. It’s something that in theory, a lot of people feel like they should be able to do, but a lot of designers in action have difficulty with it. Toronto is a hotbed for designers, but they’re always employed, and it’s so hard to get them. Stuff like Heist shutting down, or Teehan+Lax closing down doesn’t help either. There’s this weird trait of Toronto that really gives rise to these creatives, but I think we lose most of them to other ecosystems, which is not so great.”

Read the full interview.


Sebastien Gabriel, Designer for Google Chrome

“The downside of what I’m doing is that I do a lot of things at the same time. Sometimes it’s hard for me to focus as much as I would like to on a specific thing or a specific project. It’s the other side of the coin when it comes to working on something so big, you have a lot of things going through your mind. You have a daily job to see the project as a whole and not as a little thing where I can spend a week on a very specific detail. Sometimes I find that frustrating because I’m sort of OCD with pixels. I can’t have this perfect attention to everything all the time. So I need to balance that and sometimes it’s tough for me, but I got better over the years.”

Read the full interview.


Verne Ho, Director of Design at Shopify

“When I reflect on all of the things that I spend my time and energy on, I think the thing that’s always going to be most challenging is working with people. I know I just told you that working with people is also one of the most rewarding aspects, but the truth is that it’s only rewarding because it’s such an inherently challenging thing to do. And in a team that is growing so quickly, it can sometimes be very challenging to align such a diverse set of talents to a core set of missions. As a result, in my role, I often have to wear many hats and play the role of a facilitator, an educator, a mentor, and a manager, among other things. Each of my relationships are unique in their own way, which takes a ton of energy to nurture over time. There are no shortcuts when it comes to this stuff, but it’s definitely a worthy investment.”

Read the full interview.


Darrin Henein, Design Lead for Firefox Mobile at Mozilla

“I think there’s kind of two tracks that I’m focused on right now. There’s the whole leadership and management side and it’s something I’ve done for a while but Mozilla is a distributed company and no one who actually reports to me is in Toronto. That adds another layer of challenge. Right now I’m actively focusing on my management skills and leadership skills and running a team and that whole aspect. I think I’m doing fine but that’s where I’m hoping to really grow.

You can never predict how something is going to go and things always turn out to be a little bit different than you thought and it’s just this on the fly adapting — maybe it’s me or maybe it’s something everyone feels but when I’m dealing with pixels and lines of code I’m much more willing to try things and make mistakes and break things and fix them later. I cannot allow myself to do that with people. When someone comes to me with an issue or they’re trying to work through something or they’re asking me how they should approach something, I can’t just say “try this and come back in two days, and if you totally screw up we’ll fix it.” I can’t do that. I have to give them the most sound and wise advice that I’m capable of. There’s just an extra layer of caution when you’re dealing with people than when you’re dealing with bits and bytes.”

Read the full interview.


Cap Watkins, VP of Design at BuzzFeed

“One thing that has been challenging for sure is managing all these different disciplines and areas that I haven’t tackled before. When I came to BuzzFeed we didn’t have a branding team. So I created one and found this designer on the team who was a really great illustrator, I grabbed him and the two of us formed the branding design team [laughs].

I wasn’t about to send an email to all BuzzFeed employees saying, “There is a branding team now and you need to go through us!” That’s completely bonkers. So instead we took a more “grass-rootsy” approach. I was in a lot of conversations so if I heard something we could help with I’d say, “cool, we could do that for you” or “we could help you with that.” We’d do great work for them (and by we I mean Shaun, the illustrator), we’d communicate well and the work would go out. Then someone else would see it and ask where it came from, and I’d get an email: “Hey I heard there’s this thing that exists, could we get something from you for this thing we’re doing?” That expanded much faster than I expected it to so we hired another guy, Chris Rushing, who is now the senior art director and helping me run all of that. That could have all blown up in my face. We could have tried it, it could have totally fell down and then I would have walked away and pretended like it never happened. That’s not what happened, and that’s pretty awesome.

The other hard thing is, we’ve grown so fast. The company doubled the size last year in 2015. Communication, it’s hard anyway, and it becomes more complicated, the larger you get. I’m still figuring out the best way to communicate across all of these different teams and trying to keep up with them and make sure that we’re talking regularly. It has already become more of a challenge. That’ll be a time and iteration thing where it’s just like we’ll try some stuff and see what works and what doesn’t work; figure out the best balance.”

Read the full interview.


Ways We Work is a digital publication focused on telling stories and first-hand accounts of how people do the work that’s meaningful to them. Find us online and say hello!

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