This is the transcript of Ask Me Anything Session with Emmet Connolly on Product Tribes community, September 19, 2019
Emmet is Director of Product Design at Intercom where he helps a growing, global design team to create and ship the best work they can.
Before joining Intercom Emmet worked for Google in Zurich and San Francisco. There he designed Google Flight Search, and co-founded and designed Android Wear.
He got an MA in Digital Art from the University of Plymouth mostly by accident. He lives in Dublin with his wife and two children very much on purpose.
Did you always want to become a designer or did your career plans change somehow?
I don’t think I even knew what a designer was until I was 20! But my dad was a programmer and so I was always noodling on computers as a kid. I thought I was going to be an animator, SFX person, filmmaker, comic book artist — and probably loads of other things — before I started on the path to design. In retrospect, I can connect all the dots, but there was definitely no master plan.
What are some skills or hobbies that you are looking to spend more time developing right now?
I’ve been working on reading books more… it’s kind of insane how a couple of decades of being online has affected my attention span. Right now I’m reading an amazing book called The Power Broker by Robert Caro. It’s about Robert Moses, who built much of NYC in the 20th century. It’s an incredible story and so well written. It’s long though, so taking me a while!
I’ve also been dabbling in woodwork for a couple of years now. I’m strictly an amateur, but I think that’s what I like about it. You get to hack away and solve problems creatively until you get something right. And in the end, you have an actual physical object, which is a nice contrast to my work.
Other than that… do kids count as a hobby?! They certainly take up a lot of my time!
How big is your current design team and what are the 3 main challenges you’re facing as a Director of Product Design?
About 22 Product Designers, Content Designers, and Design Managers. All working across our Dublin, London, and SF offices.
Hmm, three main challenges… first things that come to mind in no particular order:
1. Maintaining a cohesive design team and standard across these different offices. Even within an office, since our designers are embedded in product teams. So we have a lot of rituals like crits and Show & Tell in our shared Design Studio to compensate.
2. Connecting design work with company-level strategy and business needs. We’re growing up as a company, which means we need a more mature definition of design. Intercom was co-founded by designers, which bought us a lot of early understanding from leadership, but eventually, you need to connect with the business side of the design world too. That’s something we’re honestly still figuring out as a team at the moment because it’s important to not lose what’s special about your team along the way.
3. This might sound trite, but it’s really true: remembering to take a moment now and then to take stock, congratulate each other, recognise good work, etc. Everything moves at such a fast pace in our world, and there are lots of ambitious people at Intercom. But it’s important to savour the little wins and make this whole thing sustainable.
Hope that makes sense. I might have a different three tomorrow!
What are the most important qualities that a director of design needs?
I truthfully think there are many different styles and approaches that can be equally valid. I work with people who are literally the opposite to my personality, but once we understand that about each other it can totally work.
That said, it’s good to be able to flex between lots of different topics: product strategy, business strategy, people management, design execution, leadership, and so on. I’ve also had to get used to doing a LOT of context-switching throughout the day… which has been useful for this AMA!
Oh, one more thing. If you’re in a fast-growth environment, it’s important to get comfortable with change and embrace the ambiguity that comes with it. It’s the easiest thing in the world to fall back on your proven skills, but that’s not what’s going to help your team get to the next stage. Here’s an article about this that I really like.
Tell us about your current and previous team. What are your team members’ roles and how do they work together?
My current team has gradually grown from three designers when I joined Intercom almost five years ago, to ~22 globally today. Which is to say that there’s never been a moment where it’s felt like we have a static team. Change is a constant, which I love.
From my point of view that means that today I’m mostly managing managers, but within the team we have Product Designers (whose focus can range from hardcore system thinking to detailed UI work) and a small number of Content Designers, which is a newer role that I think is super important to how we work. You can learn more about their role in this recent podcast.
What has been your biggest f**k up? And what did you do about it?
Oh dear, am I allowed to weasel my way out by claiming that there are no mistakes, only learning opportunities? No?
OK, here’s my honest answer. Without getting too specific, I think by far the worst fuckups you can make are the ones that negatively affect people. Product mistakes can be iterated, business mistakes can be fixed. But it sucks to be responsible for people and to then fail them in some way. There have definitely been times that even with the best intentions I’ve ended up regretting decisions. For example, there have been cases where I’ve tried to convince people to stay when the right thing for them was to leave. Conversely, it’s really difficult to talk to someone about moving on if you know they don’t want to. In both these situations, it’s human nature to want to be optimistic or just avoid conflict, but of course, that’s never the right decision for the person or the company in the long run.
My question is about the inter-relationship between Product Managers and Product Designers. How do you work with Product Managers and distribute the responsibilities of figuring out ‘what we should build’?
We actually think about this a lot. First off, quite a few of our PMs are ex-Designers or otherwise quite “product-ey” people, so it’s not difficult to speak the same language.
PMs and Designers sit together on the same team (a typical Intercom product team consists of 1 PM, 1 Product Designer, 1 EM, and 4–5 Engineers) so sitting beside each other and collaborating all day helps. But also blurs the boundaries.
In general, though Intercom PMs are responsible for defining the problem, and Product Designers are responsible for defining the solution. Our process supports this, where some of our main artefacts are based on this division.
There’s obviously a lot of push and pull involved along the way, with particular individuals leaning into their strengths more. And in fact I think the best teams manage to do this: allow the lines to get a little blurry. I wrote about this topic a while back.
BTW, this approach requires the PM and Designer to click well. That doesn’t always happen, as is the case with any random pairing of humans. So sometimes it’s fine to switch it up a bit until you find a pairing with the right chemistry.
As a director, what is your approach to supporting and nurturing your teams from a professional development perspective? Essentially ensuring that they’re in a position to grow, and work towards goals, and continually feel challenged.
We’ve put a ton of work into this over the last couple of years. As you grow from being a scrappy product-oriented group whose main focus is to ship cool shit, it’s super important. Rather than attempt to summarise everything here, I’d point you to our team’s website, where we’ve open-sourced a bunch of our internal documentation like career ladder, a guide to having an impact, and more. It’s good stuff!
Other things that aren’t there are fairly standard: twice a year we do in-depth performance reviews, everyone has a career plan, we rely on goals a lot to set clear objectives, etc. Happy to talk about any of this in more detail!
I have a very precise question about your experience but it might turn out to be a generic one. How did you come up with the novel features you designed for Google Flights? Ergo, what inspires you?
That was a fun project. We actually had a lot of time to experiment with a new UI approach to flight search, which was lucky.
I’ll answer this question in a slightly different way. Marissa Mayer made what I thought was a really astute observation in an early Flights design review: all great Google products have two key elements:
1. Some fundamental Computer Science breakthrough.
2. A new UX paradigm, often enabled by #1.
So for example Maps had AJAX-style dynamic loading, which enabled you to drag the map. Or Gmail gave you effectively infinite storage, which enabled a new Archive + Search workflow.
So for Flights, we realised that a huge problem was that flight search was incredibly slow. Like 30 seconds reload to change one little parameter because every query had to hit this ancient 1970’s shared industry backend.
Anyway, long story short we pre-cached (almost) every single combination of flights in the world so that we could have sub-second queries (that was our Comp Sci breakthrough) which enabled us to do lots of innovative things in the UI, like search by map and independent leg selection. Plus, it was fast!
For teams that are inspired by and look to create something similar to what you and your team have done for intercom.design. What would be some advice or tips on getting started?
So I understand, do you mean specifically opening up a bunch of our internal resources to the world? Or something else?
I was thinking of simply getting started — how did Intercom go about creating something like this and/or what tips do you have for an organization that wants to do something similar?
Honestly, we were pretty scrappy about it. A handful of designers who felt passionate about it got together and did 90% of the work in a week. We have an occasional roadmap-free week called “wiggle week” that team can spend any way they want: prototyping new ideas, working on strategy together, or simply paying down some design or tech debt. So the designers used a wiggle week to get this done. I was actually on holidays when it happened, so it was a pleasant surprise to return to!
More generally we’ve had a culture of sharing in Intercom for a long time (blog, talks, podcasts) so it wasn’t a big deal for us to publish some of the internal material. Plus, it’s good karma to share!
I am really curious how you, and your team, cover a multiproduct platform like Intercom? Do you have teams dedicated to specific solutions or do you work as one team? How would you compare it with your previous experiences?
We’re broken into small Product teams, each consisting of 1 PM, 1 Product Designer, 1 EM, and 4–5 Engineers. These teams are designed to have a lot of responsibility for their own strategy, roadmap planning, and execution.
So the challenge is keeping all these independent teams pointed in the same direction, and working on things that add up to a coherent whole. As a Director, that’s a lot of what my job involves: providing the right context for teams, connecting the dots between different streams of work that might not be aware of each other, etc.
My most previous role was as on the Android team at Google, where the entire team of designers was centralised in a locked-away Studio; the Engineers I worked with didn’t even have access to the space where my desk was! So in that regard, it couldn’t be more different. There are obviously huge differences between a giant company like Google and a startup like Intercom, too.
Didn’t have access to the space. Wow.
So how the collaboration between designers and developers looked like? How designers pass the design, documentation, and what is even more important, the idea to developers?
I know. There were a lot of in-person meetings in other locations. There were valid reasons for it but IMO it was not a good way to encourage collaboration and I wouldn’t want to do it again.
Any advice for new designers coming up right now?
Yeah, as Jack Weinberg said, “Don’t trust anyone over 30”! This is kind of true for our industry since things change so fast. The things that got some senior person to where they are probably won’t get you there.
More seriously, I’m glad that I got to experience both big companies and small companies. There are pros and cons to each and you’ll probably find your own personal preference. But even having the context of where your company is coming from or going to is really useful. So give yourself the chance to explore without putting yourself under too much pressure.
I’m always impressed by super-ambitious young designers, but it’s also important to leave room for your career to meander into unexpected places. It’s different for everyone but IMO you don’t need to spend your twenties worrying about career progression. Learn, have fun, make mistakes. They are worth a ton in the long run. We’re all very lucky to be working in an industry that’s both interesting and lucrative, so in general, I’d say that good things will come to you in time.
Designing Android Wear seems to me like a project between technology and fashion. Can you tell us more about how such a process works?
You know when people draw nice neat diagrams of their design process? Well here was ours:
There was a TON of iterating on the basic interactions and purpose at the beginning. What was a device this size even for? In what situations was it better than a phone?
We did a lot of prototyping to answer these questions. Here’s what an early version looked like:
The whole project roughly broke down into a couple of years of hardcore R&D: getting the small devices working, figuring out the basics of how to interact with it, etc. And then another couple “productising” it into something that couple actually be shipped.
To answer your original question, it was only in the last 18 months or so that we truly began collaborating with Industrial Designers on the physical devices, so any consideration of fashion or style really only came in at that point. Hey, this is Google we’re talking about.
What book(s) on design would you put on your must-read list? Is there a bookclub at Intercom?
Oh! We have a mini library that ranges from personal faves to solid reference material. Let me think of a couple:
About Face by Alan Cooper. Great reference manual for interaction design.
How Buildings Learn by Steward Brand. An old personal fave, ostensibly about architecture, but highly relevant to software as something that evolves and changes over time.
Understanding Comics by Scott McCloud, which is obviously about comics but is really about flow, narrative, pacing. Brilliant.
Someone on our team today mentioned how they are revisiting Creativity Inc by Ed Catmull from Pixar. All about how to get work done in creative environments.
There are loads more. I should get a full list and share!
What are some design frameworks that you think is most valuable when trying to validate a new SaaS product / feature? What are some important metrics to measure or look for?
Super interesting question! Some of the obvious ones like MRR will give you a nice simple read on the health of your business. From a UX point of view, it’s important to understand your churn rate and the causes; maybe there are some super simple fixes there. NDR is important to understand how your business will grow over time; even if you’re getting a lot of new business, you want to avoid having a “leaky bathtub” where you lose more value over time than you accrete.
At a very basic level, know how your company makes money and what the factors are that move the needle. Not only will it help your company from going extinct, it’ll also drive your design work in a more mature direction than simply being intuition-driven.
Intercom has taught me a lot about all these things that I frankly didn’t have a clue about before, and I’ve found it surprisingly interesting!
So time for the last question. What would be the one thing you would like to share with our community on Product Tribes?
“I urge you to please notice when you are happy, and exclaim or murmur or think at some point, ‘If this isn’t nice, I don’t know what is.’”
— Kurt Vonnegut
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